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Publication numberUSRE31522 E
Publication typeGrant
Application numberUS 06/481,494
Publication dateFeb 14, 1984
Filing dateApr 1, 1983
Priority dateJul 21, 1981
Publication number06481494, 481494, US RE31522 E, US RE31522E, US-E-RE31522, USRE31522 E, USRE31522E
InventorsWalter E. Rieder
Original AssigneeCincinnati Milacron Inc.
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Salt of a polyamide and functional fluid containing same
US RE31522 E
Abstract
Polyoxyalkylene polyamide lubricants having a terminal carboxylic acid group and a terminal amine group in the same molecule and a degree of polymerization of from 2 to 10 and salts thereof are provided. Stable aqueous based compositions are prepared from the polyamide or its salt, that are useful metal working and hydraulic fluids.
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Claims(32)
What is claimed is:
1. A .Iadd.salt of a .Iaddend.polyamide derivative of a polyoxalkylene diamine wherein said polyamide has (a) a single terminal carboxylic acid group and a single terminal amine group in the same molecule, and (b) a degree of polymerization of from 2 to 10 .[.or the.]. salt of the polyamide .[.which.]. is the salt of (c) the terminal carboxylic acid group, (d) the terminal amine group, or (e) both the terminal carboxylic acid and terminal amine groups, wherein the polyamide has the following formula ##STR4## where R is a divalent aliphatic, aromatic, arylaliphatic, alkylaromatic, cycloaliphatic, heteroaliphatic having oxygen or sulfur heterochain atoms, heterocyclic having one to two oxygen, sulfur or nitrogen hetero ring atoms and from 5 to 6 ring atoms or bicyclic radical or the halogenated derivatives of said divalent radical,
R' is a divalent polyoxyaliylene homopolymer or copolymer radical and
n is 2 to 10,
said .[.polyamide and its salts.]. .Iadd.salt .Iaddend.having an average molecular weight not greater than about 50,000.
2. A .[.polyamide.]. .Iadd.salt .Iaddend.according to claim 1 .[.the salt of the polyamide.]. which is the salt of the terminal carboxylic acid group.
3. A .[.polyamide or.]. salt .[.thereof.]. according to claim 1 wherein R is a divalent aliphatic hydrocarbon radical having from 2 to 12 carbon atoms.
4. A .[.polyamide or.]. salt .[.thereof.]. according to claim 1 wherein R is a phenylene or naphthylene radical.
5. A .[.polyamide or.]. salt .[.thereof.]. according to claim 1 wherein R is a divalent C4 to C6 cycloaliphatic radical.
6. A .[.polyamide or.]. salt .[.thereof.]. according to claim 1 wherein R is a divalent heteroaliphatic radical having one to two oxygen or sulfur heterochain atoms and from 2 to 6 carbon atoms.
7. A .[.polyamide or.]. salt .[.thereof.]. according to claim 1 wherein R is a divalent heterocyclic radical having one to two oxygen, sulfur or nitrogen hetero ring atoms and from 5 to 6 ring atoms.
8. A .[.polyamide or.]. salt .[.thereof.]. according to claim 1 wherein R is a divalent radical residue obtained by the removal of both carboxylic acid groups from a dimerized ethylenically unsaturated C8 to C26 fatty acid.
9. A .[.polyamide or.]. salt .[.thereof.]. according to claim 3,4, 5,6,7 or 8 wherein R' is a divalent polyoxyalkylene homopolymer radical having an average molecular weight in the range from 72 to 4000.
10. A .[.polyamide or.]. salt .[.thereof.]. according to claim 3,4, 5,6,7 or 8 wherein R' is a divalent polyoxyalkylene copolymer radical having an average molecular weight in the range from 86 to 4000.
11. The alkali metal, ammonium or organic amine salt of the carboxylic acid group of the polyamide according to claim 8.
12. The organic amine salt according to claim 11 wherein the organic amine is an alkanol amine.
13. The salt according to claim 12 wherein the alkanolamine is a mono, di or ti (C2 to C4 alkanol) amine.
14. The salt formed by the terminal amine group of the polyamide according to claim 1.
15. An aqueous functional fluid composition comprising (a) water, and (b) a lubricant compound selected from the group consisting of .[.a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization from 2 to 10,.]. a water soluble or dispersible salt of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization of from 2 to 10 or a water soluble or dispersible salt of a water insoluble polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization of from 2 to 10, wherein the polyamide derivative has the formula ##STR5## where R is a divalent aliphatic, aromatic, arylaliphatic, alkylaromatic, cycloaliphatic, heteroaliphatic having oxygen or sulfur heterochain atoms, heterocyclic having one to two oxygen, sulfur or nitrogen hetero ring atoms and 5 to 6 ring atoms or bicyclic radical or the halogenated derivative of said radical,
R' is a divalent polyoxyalkylene homopolymer or copolymer radical and
n is 2 to 10,
said .[.polyamide and.]. water soluble or dispersible .[.salts thereof.]. .Iadd.salt .Iaddend.having an average molecular weight of not greater than 50,000, the water soluble or dispersible salt being formed by the terminal carboxylic acid group, terminal amine group or both the terminal carboxylic acid and terminal amine groups of the polyamide.
16. An aqueous functional fluid composition according to claim 15 wherein the water soluble or dispersible salt of the water soluble or dispersible polyamide is a salt of the terminal carboxylic acid group of the polyamide and the water soluble or dispersible salt of the water insoluble polyamide is the salt of the terminal carboxylic acid group of the polyamide.
17. An aqueous functional fluid composition according to claim 15 wherein R is a C2 to C12 alkylene, C2 to C10 alkenylene, phenylene, C4 to C6 cycloaliphatic, mono to di(C1 to C4 alkyl) substituted phenylene, phenyl substituted C2 to C10 alkylene, phenylene di(C1 to C3 alkylene), heteroaliphatic having one to two oxygen or sulfur heterochain atoms and 2 to 10 carbon atoms, heterocyclic having one to two oxygen, sulfur or nitrogen hetero ring atoms and from 5 to 6 atoms in the ring divalent radical or a divalent radical residue obtained by removal of both carboxylic acid groups from a dimerized ethylenically unsaturated C8 to C26 fatty acid. .[.18. An aqueous functional fluid composition according to claim 17 wherein the lubricant compound is the water soluble
or dispersible polyamide..]. 19. An aqueous functional fluid composition according to claim 17 wherein the lubricant compound is the water soluble
or dispersible salt of the water soluble or dispersible polyamide. 20. An aqueous functional fluid composition according to claim 17 wherein the lubricant compound is the water soluble or dispersible salt of the water
insoluble polyamide. 21. An aqueous functional fluid composition according to claim 19 or 20 wherein the .[.lubricant is the salt of the polyamide and said.]. salt is a salt of the terminal carboxylic acid group of the
polyamide. 22. An aqueous functional fluid composition according to claim 21 wherein the salt is an alkali metal, ammonium or organic amine salt.
An aqueous functional fluid composition according to claim 22 wherein the organic amine is a mono, di or tri(alkanol) amine having 2 to 4 carbon
atoms in the alkanol group. 24. An aqueous functional fluid composition according to claim 23 wherein the organic amine is the trialkanolamine.
An aqueous functional fluid composition in accordance with claim .[.18,.]. 19 or 20 wherein R' is a divalent polyoxyalkylene homopolymer radical having an average molecular weight in the range of from 72 to
4000. 26. An aqueous functional fluid composition according to claim .[.18,.]. 19 or 20 wherein R' is a divalent polyoxyalkylene copolymer
radical having an average molecular weight of from 86 to 4000. 27. An aqueous functional fluid composition according to claim 23 wherein R is a C2 to C10 alkylene or C2 to C10 alkenylene radical.
An aqueous functional fluid composition according to claim 23 wherein
R is a phenylene radical. 29. An aqueous functional fluid composition according to claim 23 wherein R is a divalent radical residue obtained by removal of both carboxylic acid groups from a dimerized ethylenically
unsaturated C8 to C26 fatty acid. 30. An aqueous functional fluid composition according to claim 19 or 20 wherein the salt is a salt
of the terminal amine group of the polyamide. 31. An aqueous functional fluid composition according to claim 17 wherein the lubricant compound is present in an amount in the range of from 0.01% to 99% by weight based on
the total weight of the composition. 32. An aqueous functional fluid composition according to claim 31 wherein the amount of lubricant compound
is in the range of from 0.01% to 20% by weight. 33. A metal working process comprising the step of working metal in the presence of the aqueous functional fluid composition according to claim 15.
Description

This invention pertains to water soluble or dispersible polyamides having a terminal carboxylic acid group and a terminal amine group in the same molecule and salts thereof, their use in lubricants and aqueous functional fluid (e.g. metal working fluid) compositions containing such polyamides or their salts.

BACKGROUND

Aqueous based and non-aqueous functional fluids have been employed in such diverse uses as hydraulic fluids, metal working fluids, heat transfer fluids, electronic coolants, damping fluids and lubricants. To meet such diverse uses functional fluids are often tailored to have sets of properties and performance characteristics specific to the intended use of the fluid. Among the principle uses of functional fluids is their application as hydraulic fluids and metal working fluids. In metal working applications they find use in drilling, tapping, drawing, turning, milling, broaching, grinding, bending, rolling and the like metal working operations. The stability and lubricating characteristics of the functional fluid as a whole and the various components of the fluid play a major role in the performance and utility of the fluid in hydraulic and metal working applications. High stability for the fluid and its components during storage and use as well as high lubricity of the fluid are important and desirable characteristics in the use of the fluid as a hydraulic fluid or mwetal working fluid.

In recent years aqueous based functional fluids have gained in importance because of their safety, environmental, disposal, flammability, performance and economic advantages over non-aqueous functional fluids. These advantages are particularly significant in view of the strong emphasis currently being placed on safety and environmental considerations, especially in metal working operations. The economic advantages of aqueous functional fluids over non-aqueous functional fluids have become important in view of the supply problems and increasing price of non-aqueous functional fluids.

However, to derive the greatest benefit from these advantages of aqueous functional fluids, such fluids should exhibit high stability during storage and use, as well as provide a high degree of lubricity. Thus the aqueous functional fluid should be highly resistant to separation of one or more components from the mixture and resistant to undesirable breakdown (e.g. degradation) of the components of the fluid, especially undesirable degradation of a lubricant component of the fluid. Separation and undesirable degradation of components (especially a lubricant component) of an aqueous functional fluid reduces the effectiveness and useful life of the fluid leading to such undesirable effects as (1) excessive wear of metallic components of hydraulic systems (e.g. pumps and valves) and metal working equipment (e.g. cutting tools, rolls and dies) and (2) metal working products which have poor surface finish and incorrect dimensions. Although many aqueous functional fluids have been proposed by the art and a number of such fluids have been and are being used today in such applications as hydraulics and metal working those fluids have exhibited stability and/or lubricity problems which tend to limit or preclude their effective utilization. Improvements in aqueous functional fluids have therefore been continuously sought by persons skilled in the art.

It is therefore an object of this invention to overcome the disadvantages of prior art aqueous functional fluids and provide a stable, lubricating aqueous functional fluid.

Another object of this invention is to provide a novel lubricant for use in forming a stable, lubricating aqueous functional fluid.

It is a further object of this invention to provide a stable, lubricating aqueous functional fluid containing a novel polyamide lubricant.

SUMMARY OF THE INVENTION

It has now been discovered that the above objects and others, as will be apparent to those skilled in the art from the following disclosure and claims, can be achieved by (1) a polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has (a) a single terminal carboxylic acid group and a single terminal amine group in the same molecule and (b) a degree of polymerization of from 2 to 10 and the salts of the polyamide formed by the salt of the terminal carboxylic acid group, the terminal amine group or the terminal carboxylic acid and terminal amine groups of the polyamide and (2) an aqueous functional fluid composition comprising (a) water and (b) a lubricant compound selected from the group consisting of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization of from 2 to 10, a water soluble or dispersible salt of a water soluble of dispersible polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization of from 2 to 10 or a water soluble or dispersible salt of a water insoluble polyamide derivative of a polyoxyalkylene diamine wherein the polyamide has a single terminal carboxylic acid group and a single terminal amine group in the same molecule and a degree of polymerization of from 2 to 10.

DESCRIPTION OF THE INVENTION

There is now provided in accordance with this invention a polyamide advantageously exhibiting lubricity properties and having the formula ##STR1## wherein:

R is a divalent aliphatic, aromatic, arylaliphatic, alkylaromatic, cycloaliphatic, heteroaliphatic having oxygen or sulfur hetero chain atoms, heterocyclic having oxygen, sulfur or nitrogen hetero ring atoms or bicyclic radical or the halogenated derivatives thereof,

R' is a divalent polyoxyalkylene homopolymer or copolymer radical and n is 2 to 10

and the salts of said polyamide formed by the terminal carboxylic acid group, the terminal amine group or both the terminal carboxylic acid and terminal amine groups of the polyamide, said polyamide and its salts having an average molecular weight of not greater than about 50,000. Further there is provided in accordance with this invention an aqueous functional fluid composition comprising (a) water and (b) a lubricant compound selected from the group consisting of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine, a water soluble or dispersible salt of a water soluble or dispersible polyamide derivative of a polyoxyalkylene diamine or a water soluble or dispersible salt of a water insoluble polyamide derivative of a polyoxyalkylene diamine wherein the polyamide derivative of a polyoxyalkylene diamine has the following formula ##STR2## where

R is a divalent aliphatic, aromatic, arylaliphatic, alkylaromatic, cycloaliphatic, heteroaliphatic having oxygen or sulfur hetero chain atoms, heterocyclic having oxygen, sulfur or nitrogen hetero ring atoms or bicyclic radical or the halogenated derivatives thereof,

R' is a divalent polyoxyalkylene homopolymer or copolymer radical and n is 2 to 10,

said polyamide and the water soluble or dispersible salts thereof having an average molecular weight of not greater than about 50,000, the water soluble or dispersible salts being formed by the terminal carboxylic acid group, the terminal amine group or both the terminal carboxylic acid and terminal amine groups of the polyamide.

In a preferred practice of the polyamide, polyamide salt and the aqueous functional fluid composition of this invention, wherein the polyamide and the polyamide moiety of the salt thereof is given by formula (I) R is a C2 -C12 alkylene, C2 -C10 alkenylene, phenylene, C4 -C6 cycloaliphatic, mono to di (C1 to C4 alkyl) substituted phenylene, phenyl substituted C2 -C10 alkylene, phenylene di (C1 to C3 alkylene), heteroaliphatic having one to two oxygen or sulfur heterochain atoms and 2 to 10 carbon atoms, heterocyclic having one to two oxygen, sulfur or nitrogen hetero ring atoms and from 5 to 6 atoms in the ring divalent radical or a divalent radical residue obtained by removal of both carboxylic acid groups from a dimerized ethylenically unsaturated C8 to C26 fatty acid and R' is a divalent polyoxyalkylene homopolymer radical having 2 to 4 carbon atoms in the oxyalkylene group and an average molecular weight of from 72 to 2000 or a divalent polyoxyalkylene copolymer radical having 2 to 4 carbon atoms in the oxyalkylene groups and an average molecular weight of from 86 to 2000.

The salts of the terminal carboxylic acid group of the polyamide, more particularly the polyamide according to formula (I), of this invention are preferred in the practice of the polyamide and aqueous functional fluid composition of this invention.

The aqueous functional fluid composition of this invention exhibits advantageous lubricity, stability, safety, environmental and disposal characteristics.

Polyamides according to this invention are useful in metal working fluids and hydraulic fluids to provide or increase lubrication. Aqueous functional fluids in accordance with this invention are useful as metal working fluids in metal working processes such as for example milling, drilling, tapping, grinding, turning, drawing, reaming, punching, spinning and rolling.

Various embodiments of (a) the polyamide according to formula (I) and salts thereof, (b) the aqueous functional fluid comprising water and a lubricant that is a water soluble or dispersible polyamide according to formula (I), (c) the aqueous functional fluid comprising water and a lubricant that is a water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) and (d) the aqueous functional fluid comprising water and a water soluble or dispersible salt of a water insoluble polyamide according to formula (I) of this invention may be practiced by one skilled in the art. As examples of such embodiments there include polyamides, salts of polyamides, aqueous functional fluids comprising water and a water soluble or dispersible polyamide and aqueous functional fluids comprising water and a water soluble or dispersible salt of a water soluble or dispersible or insoluble polyamide, said polyamides and the polyamide moiety of said salts being according to formula (I) wherein 1 R is a divalent aliphatic radical, preferably a divalent aliphatic hydrocarbon radical and more preferably a C2 to C12 alkylene or C2 to C10 alkenylene radical, 2 R is a divalent aromatic radical, preferably a phenylene or naphthylene radical, 3 R is a divalent alkylaromatic radical, preferably a mono to di (C1 to C4 alkyl) substituted phenylene radical, 4 R is a divalent arylaliphatic radical, preferably a phenyl substituted C1 to C10 divalent aliphatic radical or phenylene dialkylene radical having 1 to 3 carbon atoms in the alkylene group ##STR3## 5 R is a divalent cycloaliphatic radical, preferably a C4 to C6 cycloaliphatic hydrocarbon radical, 6 R is a divalent heteroaliphatic radical having oxygen or sulfur hetero chain atoms, preferably a divalent heteroaliphatic radical having one to two oxygen or sulfur hetero chain atoms and 2 to 10 carbon atoms, 7 R is a divalent heterocyclic radical having oxygen, sulfur or nitrogen hetero ring atoms, preferably a divalent heterocyclic radical having one to two oxygen, sulfur or nitrogen hetero ring atoms and from 5 to 6 atoms in the ring, 8 R is a divalent bicycle radical, preferably a divalent bridged carbocyclic six membered ring radical, 9 R' is a divalent polyoxyalkylene homopolymer radical, preferably a divalent polyoxyalkylene homopolymer radical having 2 to 4 carbon atoms in the oxyalkylene group and an average molecular weight of from about 72 to about 2000, 10 R' is a divalent polyoxyalkylene copolymer radical, preferably a divalent polyoxyalkylene copolymer radical having 2 to 4 carbon atoms in the oxyalkylene group and an average molecular weight of from about 86 to about 2000, 11 the salt of the polyamide according to formula (I) is the salt, preferably the alkali metal, ammonium or organic amine salt, of the terminal carboxylic acid group of said polyamide, 12 the water soluble or dispersible salt of the water soluble or dispersible polyamide according to formula (I) is the salt, preferably the alkali metal, ammonium or organic amine salt, of the terminal carboxylic acid group of said water soluble or dispersible polyamide, 13 the water soluble or dispersible salt of the water insoluble polyamide according to formula (I) is the salt, preferably the alkali metal, ammonium or organic amine salt, of the terminal carboxylic acid group of said water insoluble polyamide, 14 the salt of the polyamide according to formula (I) is the salt of the terminal amine group of said polyamide, 15 the water soluble or dispersible salt of the water soluble or dispersible polyamide according to formula (I) is the salt of the terminal amine group of said polyamide, 16 the water soluble or dispersible salt of the water insoluble polyamide according to formula (I) is the salt of the terminal amine group of said polyamide, 17 the salt of the polyamide according to formula (I) is the salt of both the terminal carboxylic acid group and the terminal amine group of said polyamide, 18 the water soluble or dispersible salt of the water soluble or dispersible polyamide according to formula (I) is the salt of both the terminal carboxylic acid group and the terminal amine group of said polyamide and 19 the water soluble or dispersible salt of the water insoluble polyamide according to formula (I) is the salt of both the terminal carboxylic acid group and the terminal amine group of said polyamide.

When R is a divalent aliphatic group it may be straight or branched chain, saturated or unsaturated, preferably it is a divalent straight or branched chain, saturated or monoethylenically unsaturated aliphatic hydrocarbon radical having 2 to 12 carbon atoms. Examples of the divalent aliphatic group include ethylene, 1,3-propylene, 1,2-propylene, 1,4-butylene, 1,3-butylene, vinylene, 1,6-hexylene, 1,8-octylene, 1,10-decylene and 2-dodecenylene. Where R is a divalent aromatic radical, preferably a phenylene or naphthylene radical, examples include 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,2-naphthylene, 1,4-napthylene, 1,5-naphthylene, 1,6-naphthylene, 1,8-naphthylene, 2,3-naphthylene, 2,6-naphthylene and 2,7-naphthylene. R may be a divalent alkyl aromatic radical, preferably a divalent alkyl aromatic radical having one to two C1 to C4 alkyl groups bonded to a phenylene group (e.g. 2,6-dimethyl-1,3-phenylene). As R there may be used a divalent arylaliphatic group, preferably a divalent arylaliphatic group having a phenyl group bonded to an alkylene group or two alkylene groups bonded to a benzene ring, examples of which include 2-phenyl-1,3-propylene, 2-phenyl-1, 1-ethylene, phenylene-1,2-dimethylene, phenylene-1,3-dimethylene, phenylene-1,4-dimethylene and phenylene-1,4-diethylene. Where R is a divalent cycloaliphatic radical it may have from zero to two double bonds in the ring, preferably a C4 to C6 carbocyclic divalent cycloaliphatic radical having zero to two double bonds in the ring, examples of which include 1,2-cyclobutylene, 1,3-cyclopentylene, 1,4-cyclohexylene, 1,3-cyclobutylene, 3-cyclobuten-1,2-ylene, 1,2-cyclohexylene,2,5-cyclohexadien-1,4-ylene and 3-cyclohexen-1,2-ylene. When R is a divalent heteroaliphatic radical having oxygen or sulfur hetero chain atoms, preferably a divalent heteroaliphatic radical having one or two oxygen or sulfur hetero chain atoms and two to six carbon atoms, examples include --CH2 --O--CH2 --,--CH2 --S--CH2 --,--CH2 --CH2 --S--CH2 --CH2 --,--CH2 --CH2 --CH2 --S--CH2 --CH2 --CH2 -- and --CH2 --CH2 --CH2 -- S--S--CH2 --CH2 --CH2 --. R may be a divalent heterocyclic radical having one or two oxygen, sulfur or nitrogen hetero ring atoms, preferably a divalent heterocyclic radical having one oxygen, sulfur or nitrogen hetero ring atom and 5 to 6 atoms in the ring, examples of which include 2,3-thiophenediyl, 2,5-thiophenediyl, 2,3-pyrazolediyl, 2,4-furandiyl, 2,5-furandiyl, 3,4-furandiyl, 2,3-pyridinediyl, 2,5-pyridinediyl, 3,5-pyridinediyl, 2,4-pyrrolediyl, 2,3-pyrazinediyl and 2,6-pyrazinediyl. As R there may be used a divalent internally bridged carbocyclic radical examples of which include bicyclo (2,2,1) heptane-2,3-diyl and 5-norborene-2,3-diyl.

As examples of dicarboxylic acids usable in the preparation of the polyamide according to formula (I), in the practice of the polyamide and aqueous functional fluid composition of this invention, there includes, but not limited to, succinic, isosuccinic, chlorosuccinic, glutaric, pyrotartaric, adipic, chloroadipic, pimelic, suberic, chlorosuberic, azelaic, sebacic, brassylic, octadecanedioic, thapsic, eicosanedioic, maleic, fumaric, citriconic, mesaconic, aconitic, 1,2-benzene dicarboxylic, 1,3-benzene dicarboxylic, 1,4-benzene dicarboxylic, tetrachlorophthalic, tetrahydrophthalic, chlorendic, hexahydrophthalic, hexahydroisophthalic, hexahydroterephthalic, phenyl succinic, 2-phenyl pentanedioic, thiodipropionic acids, carboxylic acid products of the dimerization of C8 to C26 monomeric unsaturated fatty acids such as described in U.S. Pat. No. 2,482,760 (C. C. Goebel--Sept. 27, 1949), U.S. Pat. No. 2,482,761 (C. C. Goebel--Sept. 27, 1949), U.S. Pat. No. 2,731,481 (S. A. Harrison--Jan. 17, 1956), U.S. Pat. No. 2,793,219 (F. O. Barrett et al.--May 21, 1957), U.S. Pat. No. 2,964,545 (S. A. Harrison--Dec. 13, 1960), U.S. Pat. No. 2,978,468 (B. L. Hampton--Apr. 4, 1961), U.S. Pat. No. 3,157,681 (E. M. Fisher Nov. 17, 1964) and U.S. Pat. No. 3,256,304 (C. M. Fisher et al.--June 1966), the entire disclosures of which are incorporated herein by reference, the carboxylic acid products of the Diels-Alder type reaction of an unsaturated fatty acid with α,β-ethylenically unsaturated carboxy acid (e.g. acrylic, methacrylic, maleic or fumaric acids) such as are taught in U.S. Pat. No. 2,444,328 (C. M. Blair, Jr.--June 29, 1948) the disclosure of which is incorporated herein by reference, and the Diels-Alder adduct of a three to four carbon atom α,β-ethylenically unsaturated alkyl monocarboxylic or dicarboxylic acid (e.g. acrylic and fumaric acids respectively) and pimeric or abietic acids. Examples of the dimerized C8 to C26 monomeric unsaturated fatty acids include but are not limited to such products as Empol 1014 Dimer Acid and Empol 1016 Dimer Acid each available from Emery Industries, Inc. As examples of the carboxylic acid product of a Diels-Alder type reaction there may be cited the commercially available Westvaco Diacid 1525 and Westvaco Diacid 1550, both being available from the Westvaco Corporation. Additional examples of dicarboxylic acids usable in the preparation of the polyamide according to formula (I) for the practice of the polyamide and aqueous functional fluid composition of this invention include thiodiacetic, 4,4' dithiodibutyric, carboxyphenoxyacetic, 2,3-thiophene dicarboxylic, 2,4-thiophene dicarboxylic, 2,5-thiophene dicarboxylic, 2,3-pyrazoledicarboxylic, 2-imidazoline dicarboxylic, benzyl malonic, phenyl diacetic, phenyl dipropionic, 2,3-furandicarboxylic, 2,4-furandicarboxylic, 2,5-furandicarboxylic, 3,4-furandicarboxylic, 2,4-pyrroledicarboxylic, 2,3-pyridinedicarboxylic, 2,4-pyridinedicarboxylic, 2,5-pyridinedicarboxylic, 2,6-pyridinecarboxylic, 3,4-pyridinedicarboxylic, 3,5-pyridinedicarboxylic, 1,4-piperazinedicarboxylic, 2,3-pyrazinedicarboxylic, 2,5-pyrazinedicarboxylic, 2,6-pyrazinedicarboxylic, bicyclo (2,2,10 heptene-1,3-dicarboxylic and cis-5-norbornene-endo-2,3-dicarboxylic acids.

In place of the dicarboxylic acid there may be used the corresponding anhydride or acid halide, where the acid admits of the formation of the anhydride and acid halide, e.g. acid chloride. Where there is used the corresponding acid halide of the dicarboxylic acid to prepare the polyamide according to formula (I) it is, of course, necessary to convert the terminal acid halide groups of the polyamide product, resulting from the reaction of the acid halide with the amine group terminated polyoxyalkylene homopolymer or copolymer diamine, to the corresponding carboxylic acid group. Such conversion of the terminal acid halide groups to carboxylic acid groups may be accomplished by methods well known in the art.

In accordance with formula (I) R' is a divalent polyoxyalkylene homopolymer or copolymer radical. Such divalent radicals are derived from polyoxyalkylene homopolymer and copolymer diamines by removal of both terminal amine groups from said homopolymer and copolymer diamines. As examples of divalent polyoxyalkylene homopolymer and copolymer radicals there include said divalent radicals resulting from the removal of both terminal amine groups from polyoxyalkylene homopolymer and copolymer diamines such as for example polyoxyethylene diamine, polyoxypropylene diamine, polyoxybutylene diamine, polyoxypropylene/polyoxyethylene block and random copolymer diamine, polyoxypropylene/polyoxyethylene/polyoxypropylene block copolymer diamine, polyoxybutylene/polyoxyethylene/polyoxybutylene block copolymer diamine, polyoxybutylene/polyoxypropylene/polyoxybutylene block copolymer diamine, polyoxypropylene/polyoxybutylene/polyoxypropylene block copolymer diamine, polyoxyethylene/polyoxybutylene block or random copolymer diamine and polyoxypropylene/polyoxybutylene block or random copolymer diamine. The polyoxybutylene may contain 1,2-oxybutylene, 2,3-oxybutylene or 1,4-oxybutylene units. The length of the polyoxyalkylene blocks, i.e. the number of oxyalkylene groups in the block, may vary widely. Where the divalent polyoxyalkylene copolymer radicals are block terpolymer radicals (e.g. polyoxypropylene/polyoxyethylene/polyoxypropylene block terpolymer prepared by oxpropylating both ends of a polyoxyethylene chain) the terminal polyoxyalkylene blocks may be polyoxyethylene, polyoxypropylene or polyoxybutylene blocks containing as few as 2 oxyethylene, oxypropylene or oxybutylene units respectively or there may be present in the terminal block from 3 and up to 20 oxyalkylene units. Although the molecular weight of the polyoxyalkylene homopolymer or copolymer diamine that (1) is the source of the R' divalent radical of the polyamide according to formula (I) and (2) may be used to prepare the polyamide according to formula (I) may vary over a wide range it is preferred to use polyoxyalkylene homopolymer and copolymer diamines having an average molecular weight in the range of from about 72 to about 4000, more preferably in the range of from about 72 to 2000. Preferably the polyamide according to formula (I) has the terminal amine group or salt thereof bonded to a terminal secondary carbon atom (i.e. carbon atom having one hydrogen bonded thereto) of the divalent R' radical.

As organic amines usable in the practice of this invention for forming the amine salt of the terminal carboxylic acid group of the polyamide according to formula (I) there may be used an alkyl primary amine, alkyl secondary amine, alkyl tertiary amine and preferably a monoalkanol amine, dialkanol amine or trialkanol amine. Alkyl primary, secondary and tertiary amine salts of the carboxylic acid group having from 2 to 8 carbon atoms in the alkyl group of the amine, may be used in the practice of this invention. It is, however, preferred to use the monoalkanol amine, dialkanol amine and trialkanol amine salts of the carboxylic acid group, wherein the alkanol group contains from 2 to 8 carbon atoms and may be branched or unbranched in the practice of this invention. The use of the monoalkanol amine and trialkanol amine salts of the carboxylic acid group, wherein the alkanol group has from 2 to 8 carbon atoms, is still more preferred in the practice of this invention. Organic amines which may also be used to form the amine salts of the terminal carboxylic acid group also include C2 to C6 alkylene diamines, poly(C2 to C4 oxyalkylene) diamines having a molecular weight of from about 200 to about 900, N-C1 to C.sub. 8 alkyl C2 to C6 alkylene diamine, N,N'-di C1 to C8 alkyl C2 to C6 alkylene diamine, N,N,N'-tri C1 to C8 alkyl C2 to C6 alkylene diamine, N,N,N',N'-tetra C1 to C8 alkyl C2 to C6 alkylene diamine, N-alkanol C2 to C6 alkylene diamine, N,N'-dialkanol C2 to C6 alkylene diamine, N,N,N',N'-tetraalkanol C2 to C6 alkylene diamine and CH3 CH2 O(CH2 CH2 O)n CH2 CH2 CH2 NH2 wherein n is 1 or 2. Alkyl alkanol amines having from 2 to 8 carbon atoms in the alkyl and alkanol groups may also be used as the organic amine in the practice of this invention.

Examples of alkyl amines, which may be used to form the alkyl amine salts of the terminal carboxylic acid group of the polyamide according to formula (I), in the practice of this invention, include but are not limited to ethyl amine, butyl amine, propyl amine, isopropyl amine, secondary butyl amine, tertiary butyl amine, hexyl amine, isohexyl amine, n-octyl amine, 2-ethyl hexyl amine, diethyl amine, dipropyl amine, diisopropyl amine, dibutyl amine, ditertiary butyl amine, dihexyl amine, di n-octyl amine, di 2-ethyl hexyl amine, triethyl amine, tripropyl amine, triisopropyl amine, tributyl amine, tri-secondary butyl amine, triisopropyl amine, trihexyl amine, tri n-octyl amine and tri-2-ethyl hexyl amine. As examples of alkanol amines, which may be used to make the alkanol amine salts of the terminal carboxyl group in the practice of this invention, there include, but not limited to, monoethanol amine, monobutanol amine, monopropanol amine, monoisopropanol amine, monoisobutanol amine, monohexanol amine, monooctanol amine, diethanol amine, dipropanol amine, diisopropanol amine, dibutanol amine, dihexanol amine, diisohexanol amine, dioctanol amine, triethanol amine, tripropanol amine, triisopropanol amine, tributanol amine, triisobutanol amine, trihexanol amine, triisohexanol amine, trioctanol amine and triisooctanol amine. There may also be used in the practice of this invention amines such as methoxypropylamine, dimethyl aminopropyl amine, 1,3-propylene diamine, ethylene diamine, 3(2-ethoxyethoxy)propyl amine, N,N,N',N'-tetramethyl-1,3-butane diamine, monoethanol ethylene diamine, N,N'-diethanol ethylene diamine, N,N,N'N'-tetra hydroxymethyl ethylene diamine, N,N-diethyl ethanol amine and N-ethyl diethanol amine for preparing the organic amine salt of the terminal carboxylic acid group of the polyamide according to formula (I).

The organic amine salt of the terminal carboxylic acid group of the polyamide according to formula (I) may be prepared by methods well known in the art, such as, for example, by adding the organic amine to the polyamide according to formula (I) in the presence of an aqueous medium or conversely adding the polyamide according to formula (I) to the organic amine in the presence of an aqueous medium. In alternative methods the aqueous medium may be omitted or the aqueous medium may be replaced by an inert organic solvent medium.

Alkali metal salts of the terminal carboxylic acid group of the polyamide according to formula (I), in the practice of the polyamide and aqueous functional fluid composition of this invention include for example the lithium, sodium, potassium, rubidium and cesium salts. The lithium, sodium and potassium salts are however preferred among the alkali metal salts of the terminal carboxylic acid group of the polyamide according to formula (I). Formation of the alkali metal salts of the terminal carboxylic acid group of the polyamide according to formula (I) may be accomplished by methods well known in the art such as, for example, by adding the polyamide according to formula (I) to the hydroxide of the alkali metal in the presence of an aqueous medium.

The salts of the terminal amine group of the polyamide according to formula (I), i.e. the salt of the polyamide according to formula (I) formed by making the salt of the terminal amine group of said polyamide, in the practice of the polyamide and aqueous functional fluid composition of this invention may be the (a) quaternary ammonium salt of the terminal amine, formed by displacement of both of the amine hydrogens by organic (e.g. alkyl) groups, (b) inorganic acid salts (e.g. hydrogen chloride salt) (c) organic acid salts or (d) alkyl halide (e.g. methyl chloride) salt of the terminal amine group. Water soluble or dispersible intermolecular salts formed by the interaction of the terminal amine group of one polyamide molecule, according to this invention, with the terminal carboxylic acid group of another polyamide molecule, according to this invention, are also contemplated in the practice of the polyamide and aqueous functional fluid composition of this invention.

In the preparation of the polyamide according to formula (I), for the practice of this invention, there may be used a dicarboxylic acid or its corresponding anhydride or its corresponding acid halide.

Methods well known in the art may be employed to prepare the polyamide according to formula (I) in the practice of the polyamide and aqueous functional fluid composition of this invention. For example, an appropriate dicarboxylic acid may be reacted with a suitable polyoxyalkylene diamine under polymerizing conditions at 1:1 mole ratio in an inert organic medium with the continuous removal of the water formed during the reaction. The resulting polymer may then be isolated from the inert organic reaction medium by a method such as filtration or by evaporation of the organic medium. The reaction may be carried out (a) at room or elevated temperatures, (b) at atmospheric pressure or at pressures above or below atmospheric pressure, (c) with or without the use of a catalyst, (d) with or without the use of an inert atmosphere (e.g. nitrogen) and (e) in the absence of an inert reaction medium.

Conventional methods and apparatus well known in the art may be used to prepare the aqueous functional fluid composition of this invention. As one example of such methods the water soluble or dispersible polyamide according to formula (I) may be added to water. Another method would be to add a water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) to water. In a further method the water soluble or dispersible salt of the water insoluble polyamide according to formula (I) would be added to water. In a still further example of a method for preparing the aqueous functional fluid composition, water could be added to the water soluble or dispersible polyamide according to formula (I), the water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) or the water soluble or dispersible salt of a water insoluble polyamide according to formula (I). In an even further example of a method for preparing an aqueous functional fluid composition of this invention a salt forming compound (e.g. organic amine) may be added to water and then the water soluble or dispersible polyamide according to formula (I) added to the resulting aqueous solution. The water soluble or dispersible polyamide according to formula (I) may be added to water followed by the addition thereto of a salt forming compound (e.g. organic amine) in the preparation of the aqueous functional fluid composition of this invention.

The concentration of the (a) water soluble or dispersible polyamide according to formula (I), (b) water soluble or dispersible salt of a water soluble or dispersible polyamide according to formula (I) or (c) water soluble or dispersible salt of a water insoluble polyamide according to formula (I) in the aqueous functional fluid composition of this invention may vary over a wide range, e.g. 0.01 to 99%, preferably 0.01 to 20%, more preferably 0.03 to 10%, by weight based on the total weight of the aqueous functional fluid composition. There may be present in the aqueous functional fluid composition of this invention from about 1% to about 99.99% by weight of water based on the total weight of said composition.

Various additives well known in the art, including for example corrosion inhibitors, anti-foam agents, bacteriocides, fungicides, surfactants, extreme pressure agents, antioxidants and adjunct water soluble or dispersible lubricants, may be added to the aqueous functional fluid composition of this invention in conventional amounts.

In the preferred practice of the aqueous functional fluid composition of this invention there is provided a composition comprising water and as a lubricant a water soluble or dispersible alkanol amine salt of a water soluble or dispersible polyamide according to formula (I) wherein R is a divalent radical residue derived by the removal of the carboxylic acid groups from a dimerized C18 unsaturated fatty acid and R' is a divalent polyoxyalkylene chain having a terminal secondary carbon atom bonded to the terminal amine group of the polyamide.

This invention is further described with respect to more specific embodiments thereof in the following non-limiting examples. In the examples below all amounts and percentages are by weight and all temperatures are in degrees Centigrade unless otherwise specified.

EXAMPLES 1 to 43

These examples teach various polyamides according to this invention. The polyamides are identified in the table below by means of the dicarboxylic acid and diamine reactants used in their preparation and by their molecular weight. The polyamides were prepared by conventional methods, two examples of which are as follows.

Method I

34.43 grams (0.2 moles) of cyclohexane-1,4-dicarboxylic acid, 125.46 grams (0.2 moles) of Jeffamine ED-600 (a diamine, having an average molecular weight of about 600, that is a primary amine terminated propylene oxide capped polyoxyethylene available from the Texaco Chemical Company) and 150 milliliters of xylene were placed in a reaction flask equipped with an agitator and a trap. The reaction mixture was stirred and heated to reflux. Refluxing and stirring were maintained for 73 hours resulting (1) the collection of 6.7 milliliters of water (100% of theoretical) and (2) a viscous, turbid, amber reaction mixture. The xylene was removed from the reaction mixture on a rotary evaporator to produce 153.9 grams of a glassy amber solid having an acid value of 14.2 and neutralization value of 12.8.

Method II

93.4 grams (0.16 moles) of Dimer Acid 3680 (see (a) below) and 154.7 grams (0.16 moles) of Jeffamine ED 900 (see (k) below) were placed in a reaction flask. The contents of the flask were heated to 230 to 255 C. and stirred for 37 hours while applying a vacuum of 5 to 7 mm, with a slight nitrogen bleed, to remove the water produced by the reaction. The water was collected in a dry ice trap. At the end of the reaction period the contents of the flask were cooled to room temperature under a nitrogen blanket. A product was obtained which exhibited an acid value of 1.3 and a neutralization value of 0.5.

The dicarboxylic acid and diamine reactants listed in the table below are described as follows.

(a) Dimer Acid 3680-Hystrene 3680-80% Dimer Acid, acid value 190-197, saponification value 191-199, neutral equivalent 285-295, monomer acid 1% max., viscosity at 25 C. (cSt) 8,000, unsaponifiable 1.0, monomer Tr., Dimer 83, Trimer 17, available from the Humko Sheffield Chemical Inc. Hystrene is a registered trademark of Humko Sheffield Chemical Inc.

(b) Dimer Acid 3675 CS-Hystrene 3675CS-75% Dimer Acid, 3% monomer, acid value 194-201, saponification value 196-203, neutral equivalent 279-289, monomer acid 3-4 max, viscosity at 25 C. (cSt) 12000, unsaponifiable 1.0, Monomer 3, Dimer 85, Trimer 12 available from the Humko Sheffield Chemical Inc. Hystrene is a registered trademark of Humko Sheffield Chemical Inc.

(c) Empol 1014 Dimer acid: A polymerized fatty acid having a typical composition of 95% dimer acid (C36 dibasic acid) approx. mol. wt. 565, 4% trimer acid (C54 tribasic acid) approx. mol. wt. 845 and 1% monobasic acid (C18 fatty acid) approx. mol. wt. 282 available from Emery industries, Inc.

(d) Westvaco Diacid 1525: The Diels-Alder reaction product of tall oil and acrylic acid available from Westvaco Corp.

(e) Westvaco Diacid 1550: The Diels-Alder reaction product of tall oil and acrylic acid, said product refined to contain about 10% monoacids, available from the Westvaco Corp.

(f) DBD-DuPont DBD-dibasic acid mixture of high molecular weight dibasic acids, primarily C12 and C11, typical composition dodecanedioic acid 34% by wt., undecanedioic acid 50% by wt., sebacic acid 7% by wt., other dibasic acids 8.5% by wt., monobasic acids 1% by wt., nitro dibasic acids 7.2% by wt., other organic nitro compounds 0.9% by wt., inorganic nitrogen compounds 0.9% by wt., water 0.5% by wt., total nitrogen 0.9% by wt., off white flaked solid, softening point 85-95 C. and average molecular weight 215 available from E. I. DuPont de Nemours & Company Inc.

(g) Jeffamine D230 is a primary amine terminated polyoxypropylene diamine having an average molecular weight of about 230 and available from the Texaco Chemical Company.

(h) Jeffamine D400 is a primary amine terminated polyoxypropylene diamine having an average molecular weight of about 400 and available from the Texaco Chemical Company.

(i) Jeffamine D2000 is a primary amine terminated polyoxypropylene diamine having an average molecular weight of about 2000 and available from the Texaco Chemical Company.

(j) Jeffamine ED 600 is a diamine having an average molecular weight of about 600 available from the Texaco Chemical Company and being a primary amine terminated propylene oxide capped polyoxyethylene.

(k) Jeffamine ED900 is a diamine having an average molecular weight of about 900 available from the Texaco Chemical Company and being a primary amine terminated propylene oxide capped polyoxyethylene.

(l) Jeffamine ED 2001 is a diamine having an average molecular weight of about 2000 available from the Texaco Chemical Company and being a primary amine terminated propylene oxide capped polyoxyethylene.

(m) Dow XA 1332 is a diamine obtained from the Dow Chemical Company and is a primary amine terminated propylene oxide capped 400 molecular weight polyoxyethylene.

(n) Dow XA 1333 is a diamine obtained from the Dow Chemical Company and is a primary amine terminated propylene oxide capped 600 molecular weight polyoxyethylene.

Jeffamine is a registered trademark of the Texaco Chemical Company and Dow is a registered trademark of the Dow Chemical Company.

______________________________________Ex-                                Averageam-                                Molecularple                                weight ofNo.  Dicarboxylic Acid                Diamine       polyamide______________________________________1    Dimer Acid 3680 Jeffamine ED-900                              1,6002    Dimer Acid 3680 Jeffamine ED-900                              2,7003    Dimer Acid 3680 Jeffamine ED-900                              4,0004    Dimer Acid 3680 Jeffamine ED-900                              5,4005    Dimer Acid 3680 Jeffamine ED-900                              18,0006    Dimer Acid 3680 Jeffamine D-230                              2,6007    Dimer Acid 3680 Jeffamine D-400                              2,8008    Dimer Acid 3680 Jeffamine D-2000                              12,0009    Dimer Acid 3680 Jeffamine ED-600                              3,90010   Dimer Acid 3680 Jeffamine ED-2001                              9,30011   Dimer Acid 1014 Jeffamine ED-900                              8,20012   Dimer Acid 1014 Jeffamine ED-2001                              19,00013   Dimer Acid 1014 Jeffamine D-400                              9,00014   Dimer Acid 1014 Dow XA 1332   6,50015   Dimer Acid 3675 CS                Dow XA 1333   10,40016   Diacid 1550     Jeffamine ED-900                              3,60017   Diacid 1550     Jeffamine ED-2001                              5,70018   Diacid 1550     Dow XA 1332   4,40019   Diacid 1550     Dow XA 1333   3,90020   Diacid 1525     Jeffamine ED-900                              4,60021   Diacid 1525     Jeffamine ED-2001                              5,90022   Diacid 1525     Jeffamine ED-600                              3,70023   Diacid 1525     Jeffamine D-400                              2,80024   Diacid 1525     Dow XA 1333   8,00025   Dodecanedioic acid                Jeffamine ED-900                              5,70026   DBD             Jeffamine ED-600                              2,60027   Adipic Acid     Jeffamine ED-600                              4,30028   Azelaic Acid    Jeffamine ED-600                              7,10029   Azelaic Acid    Jeffamine ED-900                              4,60030   Azelaic Acid    Dow XA 1332   7,30031   p-phenylene diacetic                Jeffamine ED-600                              3,600Acid32   2,5-pyridinedi- Jeffamine ED-2001                              3,100carboxylic Acid33   Terephthalic Acid                Jeffamine ED-900                              5,00034   Cyclohexane-1,4-                Jeffamine ED-600                              4,200dicarboxylic Acid35   Hexachloronorbornene                Jeffamine ED-600                              14,000dicarboxylic Acid36   Maleic Anhydride                Jeffamine D-400                              1,40037   Fumaric Acid    Jeffamine D-400                              1,40038   Fumaric Acid    Jeffamine ED-900                              3,20039   Diglycolic Acid Jeffamine D-2000                              5,10040   Terephthalic Acid                Jeffamine ED-600                              2,10041   Terephthalic Acid                Jeffamine ED-400                              2,80042   Mesaconic Acid  Jeffamine ED-900                              8,300______________________________________
EXAMPLES 43 to 113

These examples, as shown in the table below, demonstrate aqueous functional fluid compositions in accordance with this invention.

__________________________________________________________________________      Wt. of                          Wt. ofExamplePolyamide      Polyamide Wt. (gm) of           WaterNo.  of Ex. No.      (gm)  NaOH                KOH NH4 OH                        TEA.sup.○1                            MIPA.sup.○2                                 DEA.sup.○3                                      (gm)__________________________________________________________________________43   1     15                15            47044   1     15                         10.6 474.445   2     15                15            47046   2     15                    7.5       477.547   3     15                    15        47048   3     15        5.6                   479.449   4     15                15            47050   4     15        5.6                   479.451   5     15                15            47052   6     15                15            47053   6     15    4.0                       48154   7     15                15            47055   7     15        5.6                   479.456   8     15                15            47057   8     15                    7.5       477.558   9     0.6               0.6           498.859   9     1.5               1.5           49760   9     6                 6             48861   9     15                15            47062   9     60                60            38063   10    15                15            47064   10    15            3.5               481.565   11    15                15            47066   12    15                15            47067   13    15                15            47068   14    15                15            47069   15    15                15            47070   16    15                15            47071   16    15        5.6                   479.472   17    15                15            47073   17    15                              48574   17    15    4.0                       48175   18    15                15            47076   19    15                15            47077   20    15                15            47078   20    15                              48579   21    15                15            47080   21    15            3.5               481.581   22    15                15            47082   22    15    4.0                       48183   23    15                15            47084   23    15                    7.5       477.585   24    15                15            47086   25    15                15            47087   25    15        5.6                   479.488   26    15                15            47089   26    15                    7.5       477.590   26    15                         10.6 474.491   27    15                15            47092   27    15                              48593   27    15        5.6                   479.494   28    15                15            47095   28    15                         10.6 474.496   29    15                15            47097   29    15            3.5               481.598   30    15                15            47099   31    15                15            470100  31    15                         10.6 474.4101  32    15                15            470102  32    15    4.0                       481103  33    15                15            470104  33    15    4.0                       481105  34    15                15            470106  35    15                15            470107  36    15                15            470108  37    15                15            470109  38    15                15            470110  39    15                15            470111  40    15                15            470112  41    15                15            470113  42    15                15            470__________________________________________________________________________ .sup.○1 triethanol amine .sup.○2 monoisopropanol amine .sup.○3 diethanol amine
EXAMPLES 114 to 184

500 grams of each of the formulations of Examples 43 to 113 were diluted to 3000 grams with water and the resulting diluted formulations then evaluated for lubricity in accordance with the following test procedure.

Test Procedure

A wedge-shaped high-speed tool is forced against the end of a rotating (88 surface feet per minute) SAE 1020 steel tube of 1/4 inch wall thickness. The feed force of the tool is sufficient to cut a V-groove in the tubing wall, and the chips flow out of the cutting area in two pieces (one piece from each face of the wedge-shaped tool). The forces on the tool as a result of workpiece rotation and of tool feed are measured by a tool post dynamometer connected to a Sanborn recorder. Any welding of chips to tool build-up is reflected in the interruption of chip-flow (visual) and in increased resistance to workpiece rotation. The cutting test is performed with the tool-chip interface flooded throughout the operation with circulating test fluid. Tool and workpiece are in constant dynamic contact during this time, and the test is not begun until full contact is achieved all along each cutting edge. The duration of the test is three minutes.

The results obtained in accordance with the above test procedure are given in the following table.

______________________________________          Formulation of                      ForceExample No.    Example No. (lbs.)______________________________________114            43          454115            44          458116            45          368117            46          411118            47          358119            48          490120            49          308121            50          472122            51          318123            52          408124            53          498125            54          400126            55          503127            56          415128            57          389129            58          480130            59          426131            60          306132            61          307133            62          319134            63          394135            64          457136            65          316137            66          390138            67          373139            68          308140            69          307141            70          406142            71          481143            72          433144            73          392145            74          523146            75          385147            76          406148            77          431149            78          419150            79          464151            80          468152            81          458153            82          487154            83          471155            84          487156            85          460157            86          394158            87          459159            88          381160            89          437161            90          334162            91          487163            92          501164            93          488165            94          473166            95          487167            96          459168            97          498169            98          445170            99          415171            100         483172            101         503173            102         524174            103         446175            104         491176            105         473177            106         443178            107         448179            108         419180            109         480181            110         388182            111         483183            112         385184            113         471______________________________________
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5128441 *May 4, 1990Jul 7, 1992Texaco Chemical CompanyPolyoxyalkylene diamines reacted with diacid and diamine, curing agents for epoxy resins
US5133889 *Dec 2, 1988Jul 28, 1992Institut Francais Du PetroleReaction of sulfur mono- or dichloride with a monoolefin and reaction with a mercaptate and mercaptate polysulfide for gears and metal working
US5239048 *May 4, 1990Aug 24, 1993Texaco Chemical CompanyAromatic polyoxyalkylene amidoamines
US5260268 *Mar 29, 1993Nov 9, 1993The Lubrizol CorporationMethods of drilling well boreholes and compositions used therein
US5286395 *May 14, 1992Feb 15, 1994Institut Francais Du PetroleOil additive
US5378798 *Jul 10, 1992Jan 3, 1995Shell Oil CompanyComposition and process for coating metallic substrates
US5599777 *Oct 6, 1993Feb 4, 1997The Lubrizol CorporationMethods of using acidizing fluids in wells, and compositions used therein
US8476204 *Nov 23, 2005Jul 2, 2013Ab SkfLubricant and use of a lubricant
US20100152076 *Nov 23, 2005Jun 17, 2010Ab SkfLubricant and use of a lubricant
Classifications
U.S. Classification508/260, 528/347, 72/42, 528/335, 528/337, 528/341, 525/420, 528/346
International ClassificationC10M107/44, C10M173/02
Cooperative ClassificationC10M173/02, C10M107/44
European ClassificationC10M173/02, C10M107/44
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Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILACRON INDUSTRIAL PRODUCTS, INC.;REEL/FRAME:013221/0848
Effective date: 20020808
Owner name: DEUTSCHEBANK TRUST COMPANY AMERICAS 130 LIBERTY ST
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILACRON INDUSTRIAL PRODUCTS, INC. /AR;REEL/FRAME:013221/0848
Aug 19, 2002ASAssignment
Owner name: MILACRON INDUSTRIAL PRODUCTS, INC., MICHIGAN
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILACRON INC.;REEL/FRAME:013211/0001
Effective date: 20020808
Owner name: MILACRON INDUSTRIAL PRODUCTS, INC. 31003 INDUSTRIA
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILACRON INC. /AR;REEL/FRAME:013211/0001
May 1, 2002ASAssignment
Owner name: BANKERS TRUST COMPANY, AS ADMINISTRATIVE AGENT, NE
Free format text: SECURITY AGREEMENT;ASSIGNORS:VALENITE U.S.A. INC.;MILACRON INC.;TALBOT HOLDINGS, LTD.;AND OTHERS;REEL/FRAME:013110/0122
Effective date: 20011210
Owner name: BANKERS TRUST COMPANY, AS ADMINISTRATIVE AGENT 130
Free format text: SECURITY AGREEMENT;ASSIGNORS:VALENITE U.S.A. INC. /AR;REEL/FRAME:013110/0122
Jun 8, 2001ASAssignment
Owner name: VALENITE INC., MICHIGAN
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILACRON INC.;REEL/FRAME:012002/0248
Effective date: 19991105
Owner name: VALENITE USA INC., MICHIGAN
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:VALENITE INC.;REEL/FRAME:011898/0942
Owner name: VALENITE INC. 31700 RESEARCH PARK DR. MADISON HTS.
Owner name: VALENITE INC. 31700 RESEARCH PARK DR.MADISON HTS.,
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILACRON INC. /AR;REEL/FRAME:012002/0248
Owner name: VALENITE USA INC. 31700 RESEARCH PARK MADISON HTS.
Owner name: VALENITE USA INC. 31700 RESEARCH PARKMADISON HTS.,
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:VALENITE INC. /AR;REEL/FRAME:011898/0942