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Publication numberUS3856711 A
Publication typeGrant
Publication dateDec 24, 1974
Filing dateNov 29, 1972
Priority dateNov 29, 1965
Also published asCA983806A1, DE1543970A1, DE1543970B2, DE2355402A1, DE2355402B2, DE2355402C3, US3709838
Publication numberUS 3856711 A, US 3856711A, US-A-3856711, US3856711 A, US3856711A
InventorsDater A, Mausner M
Original AssigneeWitco Chemical Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Liquid detergent compositions
US 3856711 A
Abstract  available in
Images(6)
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Claims  available in
Description  (OCR text may contain errors)

United States Patent [1 1 Mausner et al.

1*Dec. 24, 1974 LIQUID DETERGENT COMPOSITIONS [75] Inventors: Marvin L. Mausner, Teaneck;

Arnold H. Dater, Fair Lawn, both of NJ.

[73] Assignee: Witco Chemical Corporation, New

York, NY.

The portion of the term of this patent subsequent to Jan. 9, 1990, has been disclaimed.

221 Filed: Nov. 29, 1972 211 App]. No.: 310,293

Related US. Application Data [63] Continuation-impart of Ser. No. 91,153, Nov. 19, 1970, Pat. No. 3,709,838, which is a continuation-impart of Ser. No. 777,143, Nov. 19, 1968, abandoned, which is a continuation-in-part of Ser. No. 510,358, Nov. 29, 1965, abandoned,

[ Notice:

[52] US. Cl 252/545, 252/544, 252/548 [51] Int. Cl...... Clld 3/075, C1 1d 1/83, C1 1d 3/26 [58] Field of Search 252/545, 548, 529

[56] References Cited UNITED STATES PATENTS 2,859,182 11/1958 Carroll ..252/548 3 ,232,880 2/1966 Mausner 252/529 OTHER PUBLICATIONS Kastra, Def. Pub. of Serial No. 182,863 filed 9-22-71, Published in 903 0.0. 6 on 10-3-72, Defensive Publication N0. T 903,009.

Primary Examiner-Mayer Weinblatt Assistant Examiner-Edith L. Rollins Attorney, Agent, or Firm-Morton Friedman; Jordan ,1. Driks; Albert L. Gazzola [57] ABSTRACT 19 Claims, N0 Drawings LIQUIDv DETERGENT COMPOSITIONS This application is a continuation-in-part ofapplication Ser. No. 91,153, filed Nov. 19, 1970, issued as US. Pat. No. 3,709,838 which is a continuation-in-part of application Ser. No. 777,143, filed Nov. 19, 1968, now abandoned which is a continuation-in-part of application Ser. No. 510,358, filed Nov. 29, 1965, now abandoned.

This invention is directed to new and useful anhy drous or essentially anhydrous low foaming liquid surfactant compositions, and more particularly .to polyfunctional liquid detergent compositions that comprise essentially 100%.active organic surfactants and to a method of making them.

The productionand marketing of polyfunctional detergent compositions has-been known for a number of years and numerous formulations have been evolved. Various combinations of surfactant materials have been prepared in a wide range of concentrations to modify theproperties of the detergent compositions in a desired manner. These combinations are disclosed in numerous US. Patents, illustrative of which are Nos. 2,383,737; 2,733,213; 2,733,214; 2,746,931; 2,826,596; 2,831,815; 2,846,402; 3,075,922; .and 3,239,468.

it is known in the detergent art toprepare polyfunetional detergent compositions in powdered or flake form, suchas obtained by the spray-drying or drumdrying of a slurry of a detergent composition, that contain a high concentration of active organicsurfactant materials, i.e., as high as-90% of active surfactant material. lt has also been suggested, as disclosedyin the aforementionedULS. Pat. No. 3,239,468, to prepare detergent compositions comprising certain proportions of alkyl aryl'sulfonates, nonionic polyoxyethylene alkylphenol condensates and fatty acid-diethanolamine condensates without any added water or other vehicle, such as a liquid medium, and subsequently diluted to use concentrations, or subsequently admixed with a liquid medium. lnpoint of fact, in the actual working example disclosures of said Pat. No. 3,239,468, aqueous slurries of thealkyl aryl sulfonates are utilized and, in Example 1 of said patent, which describes a detergent composition produced in the absence of either a liquid medium or water as added diluent, a very considerable amount of water is actually present,.namely, about 16% of the total composition. Furthermore, as there disclosed, the alkyl aryl sulfonates, such as dodecylbenzene sulfonate, can be utilized in the form of their alkali metal, ammonium or alkanolamine salts. When the procedures .described'in said patent, utilizing the proportions of the various ingredients disclosed therein, are, however, sought to be appliedto the production of essentially 100% active stable liquid detergent compositions, such compositions are, in fact, characterized by poorclarity and substantially instability, separating into layers after even quite short periods of standing. So far as we are aware, the preparation'of polyfunctional organic detergent compositions in the form of stable, hmogeneous liquids, which advantageously are also lowfoaming, generally speaking, has been limited to solutions having a concentration of active organic surfactant materials of the order of 50, to 70%. While it is highly desirable from an economy standpoint .to prepare polyfunctional detergent compositions in liquid form which are stableover prolonged periods of time, and in which the content of the active organic surfactants approaches when attempts are made to produce such compositions, various problems arise.

One such problems in the production of essentially 100% active, stable polyfunctional liquid low foaming detergentcompositions is the matter of instability. This instability may be evidenced by the formation of two or more immiscible phases either during the preparation of the detergent composition or on standing over short periods of time. Another of such problems is the production of such a detergent composition which will, upon dilution with water in certain concentrations, where such dilution may be desired, dissolve readily and operate to perform effectively its desired detergent functions.

In accordance with the present invention, it has been found that a 100% active, or essentially 100% active, of essentially anhydrous polyfunctional organic detergent composition in theform of a clear, homogeneous, stable liquid having low foaming properties can be prepared by a certain balancing of a number of essential ingredients, and advantageously employing a particular mixing or blending procedure.

The essentially anhydrous liquid polyfunctional organic detergent compositions of the present invention contain as essential ingredients, in the ranges of proportions set forth hereafter, (1) ethanolamine (i.e., monoethanolamine, diethanolamine and triethanolamine or mixtures of two or more thereof) salts of alkyl benzene sulfonic acids or alkyl toluene sulfonic acids, particularly the diethanolamine or triethanolamine salts of said sulfonic acids (2) certain ethanolamides or isopropanolamides, and (3) certain water-soluble nonionic organic surfactants which are normally liquid or, in other words, liquid at usual room temperatures.

The alkyl benzene sulfonic acids and the alkyl toluene sulfonic acids, which are utilized in the form of their ethanolamine salts as stated] above, are those in which the alkyl radical, which may be linear or branched chain, contains predominately from 8 to 16 carbon atoms and, better still, from 11 to 15 carbon atoms. Especially satisfactory are dodecyl benzene sulfonic acid and tridecyl benzene sulfonic acid, as well as mixtures thereof or mixtures in which one or the other or both predominate, in which the dodecyl and tridecyl radicalsare essentially normal or straight chain. The alkyl benzene or alkyl toluene sulfonic acids are well known in the art and are conventionally made by alkylating benzene or toluene with normal or straight chain chloroparaffins, polypropylene, or olefins, although other sources of alkyl raidcals can, of course, be utilized. The ethanolamine salts of the aforesaid sulfonic acids are formed and incorporated in the manner described below. lt may be noted that it is important to the achievement of the results of the present invention, taken in conjunction with the other essential aspects of the invention, not only to utilize ethanolamine salts of the aforesaid sulfonic acids, because the alkali metal salts are not operative, but, in addition, that said ethanolamine salts be formed in situ. it may also here be noted that many alkanolamines are unsatisfactory for the purposes of our present invention. Furthermore, to achievethe optimum advantages of the present invention, said in situ formation should be carried out in the manner hereafter described as a part of the overall method of blending the ingredients to form the final liquid detergent compositions of the present invention. It may be stated that, in itself, in situ formation, broadly;

of ethanolamine salts of alkyl benzene sulfonic acids as a part of a procedure for producing liquid detergent compositions is known to the art and no claim is made generally thereto. However, in such cases, the in situ formation of ethanolamine salts of alkyl benzene sulfonic acids has occured in connection with the production of liquid detergent compositions containing substantial quantities of water, for instance, about 35 to 50%, as an essential part ofthe liquid detergent compositions, as shown, for example, in US. Pat. No. 3,232,880 and in Australian Pat. No. 164,644. In any event, and as pointed out above, our present invention and our polyfunctional essentially 100% active stable liquid detergent compositions are sharply distinguishable therefrom.

The normally liquid water-soluble non-ionic surfactants which are utilized in the liquid detergent compositions of the present invention serve as primary surfactants and defoamers as well as liquid carriers. They are the normally liquid water-soluble polyoxyethylenepolyoxypropylene glycol condensation products described in US. Pat. No. 2,674,619, and sold by Wyandotte-BASF under the tradename PLURONlC. The normally liquid water-soluble PLURONICS generally have a molecular weight of less than about 7500, and are generally prepared by reacting ethylene oxide with a polyoxypropylene glycol having a molecular weight of 950, or higher, until a sufficient degree of water solubility has been attained. The preparation and charac teristics of this class of surfactants are well known and require no further discussion herein. These normally liquid water-soluble polyoxyethylene-polyoxypropylene glycol surfactants, besides being essential ingredients to produce the present stable 100% active essentially anhydrous polyfunctional organic detergent compositions, are advantageously effective as foam reducing agents.

The ethanolamides and/or isopropanolamides, which serve as viscosity builders in the liquid detergent compositions of the present invention, are the fatty acid monoethanolamides, diethanolamides and isopropanolamides in which the fatty acid acyl radical contains from to 16 carbon atoms. Said amides should be either normally liquid or have melting points not higher than about 60 C. Especially satisfactory are the diethanolamides derived from coconut oil mixed fatty acids or special fractions containing, for instance, very predominately C or C fatty acids, and wherein the mol ratio of the diethanolamine to the higher fatty acid is about 1:1.

The proportions of the ingredients, in terms of weight comprising the liquid detergent compositions of the present invention are (A) from 30 to 90%, better still 45 to 75%, of the aforementioned ethanolamine salts of the alkyl benzeneor alkyl toluene-sulfonic acids (B) from 5 to 35%, better still 15 to 30%, of the aforementioned non-ionic normally liquid, water-soluble polyoxyethylene-polyoxypropylene glycol surfactants, and (C) from 5 to 35%, better still 12 to of the aforementioned fatty acid amides of monoethanolamine, diethanolamine or isopropanolamine. Particularly desirable are liqud detergent compositions made pursuant to the present invention wherein the aforesaid ethanolamine salts of the alkyl benzeneor alkyl toluenesulfonic acid constitute from 52 to 64%, the aforesaid non-ionic surfactant constitutes from 22 to and the aforesaid fatty acid monoor diethanolamides or isopropanolamides constitute from 14 to 18% of the compositions.

1n the preparation of the polyfunctional essentially active stable liquid detergent compositions ofthe present invention, it is particularly advantageous first to form a substantially homogeneous solution of the non-ionic normally liquid water-soluble surfactant with an ethanolamine and then gradually add thereto, under conditions of agitation, the alkyl benzene sulfonic acid and/or alkyl toluene sulfonic acid in an amount essentially to be neutralized by said ethanolamine thereby to form the ethanolamine salt of said sulfonic acid. the temperature of the mixture being controlled so as not to exceed about 100C and preferably not to substan tially exceed 50C, and then add the ethanolamide and- /or isopropanolamide. under conditions of agitation, until a clear, homogeneous liquid is obtained. An alternative procedure is first to form a mixture of the nonionic surfactant and the sulfonic acid and then gradually add thereto the ethanolamine under conditions of agitation. Still other procedures can be used but the non-ionic surfactant must comprise the vehicle in which in situ formation of the ethanolamine salt of the sulfonic acid is effected. Thus, for instance, stable compositions cannot be formed if the ethanolamine salt of the sulfonic acid is sought to be formed in situ in the ethanolamide and/or isopropanolamide per se. As indi cated, nonionic surfactant must be present during the in situ formationof the ethanolamine salt of the sulfonic acid.

It may also be noted that the polyfunctional essentially 100% active stable liquid detergent compositions of the present invention cannot be made by initially preparing an aqueous solution of the active ingredients and then evaporating off the water because, among other things, at a concentration of about 60% of the active ingredients, breakdown of the composition occurs and instability results.

The following examples include illustrative or particularly preferred embodiments of the present invention, but they are not to be construed as in any way limitative of the invention since numerous other embodiments can readily be evolved in the light ofthe guiding principles and teachings provided herein. All parts recited are by weight.

EXAMPLE 1 To 26 parts ofliquid water soluble polyoxyethylenepolyoxypropylene glycol sold under the trade name of PLURONIC L-64, by Wyandotte BASF, there was added 20 parts of diethanolamine. Then 40 parts of dodecyl benzene sulfonic acid (88% minimum activity) was slowly added, under conditions of agitation, the temperature of the reactants and the reaction mixture being maintained below 50C and, better still, between about 20 and 30C. The aforementioned amount of diethanolamine is the stoichiometric quantity required to neutralize the dodecyl benzene sulfonic acid. When the neutralization was complete, 14 parts of a superamide (made from 1 mol of coconut oil fatty acids and 1 mol of diethanolamine) was added, under conditions of agitation, until a clear, homogeneous low foaming liquid was obtained The properties of said low foaming liquid detergent composition, hereinabove prepared, were as follows:

Appearance Clear amber liquid Water content Less than 2% Cloud point Less than 0C Clear point Less than 0C pH 7.9

The stability of said liquid detergent compositions was excellent, no separation of ingredients occurring after several months of aging at ambient temperatures and also at 0C.

The above procedure, when conducted at temperatures of as high as 100C, or even higher, results in detergent compositions which are progressively slightly darker as the temperature of the reaction increases. The darker compositions, prepared according to the present invention, are utilized when the end use thereof is not affected by the darker colors or wherein darker colored compositions are preferred. The efficacy and utility of the detergent compositions is, however, not affected by such color considerations.

The following table illustrates the slight degree of darkening of the final liquid detergent compositions as the temperature is increased. Readings were made on a Klett-Summerson Photoelectric Colorimeter. Readings were made immediately after neutralization and one hour after neutralization at the temperature indicated, to simulate conditions in the processing of large batches which would be difficult to coolrapidly.

it is apparent from the above table that the temperature of the reaction may be increased considerably over 95C. if it is desired to produce a darker product.

The final liquid detergent composition is pourable. However, when diluted to up to about 50 percent with water, gelling occurs. This pourable" characteristic of the substantially anhydrous final liquid detergent, which gells when water is added illustrates the importance and criticality of excluding water during the preparation of the compositions of the present invention, and the unexpectedness of our invention since it would have been assumed that any effort by those skilled in the art to make compositions such as ours would have resulted in gels. We found, however, surprisingly, that polyfunctional essentially 100% active liquid detergent compositions of the type here involved could be made which are stable and readily pourable.

EXAMPLE la In sharp contrast to the results obtained in Example 1, when a detergent composition was sought to be made by simply mixing together 26 parts of the same PLURONIC L -64 used in Example l, 14 parts of the same superamide used in Example I, and 60parts of the sodium salt ofdodecyl benzene sulfonic acid 100% active, or in the form of an aqueous slurry as in the aforesaid Pat. No. 3,239,468), the resulting composition was unclear and unstable andquickly formed separate layers, including undissolved material.

EXAMPLE lb Again, when an essentially anhydrous detergent coinposition was sought to be made by simply admixing-together 26 parts of the same PLURONlC L-64 used in Example 1, l4 parts of the same superamide used in Example I, and parts of a preformed diethanolamine salt of dodecyl benzene sulfonic acid made by admixing 20 parts of diethanolamine with 40 parts of dodecyl benzene sulfonic acid (88% minimum activity), an extremely non-homogeneous. unclear composition resulted in which solids readily separated out. In deed, a usable preformed diethanolamine salt of dodecyl benzene sulfonic acid could not be made because an unmanageable gel resulted on mixing diethanolamine with dodecyl benzene sulfonic acid.

EXAMPLE lc A detergent composition was sought to be made by simply admixing together 30 parts of a PLURONIC L-44, a liquid water soluble polyoxyethylene-polyoxypropylene glycol condensation product, 50 parts of a coconut fatty acid-diethanolamine condensate (mol ratio of coconut fatty acids: diethanolamine being l:l and 20 parts of the sodium salt of dodecyl benzene sulfonic acid (I007: active or in the form of an aqueous slurry as in the aforesaid Pat. No. 3,239,648). The resulting composition was unclear and unstable, readily separating out into layers.

EXAMPLEId A detergent composition was sought to be made by simply admixing together 30 parts of PLURONlC L-44, a liquid water soluble polyoxyethylene-polyoxypropylene glycol condensation product, 50 parts ofa coconut fatty acid-diethanolamine condensate (mol ratio of coconut fatty acids: diethanolamine being l:l and 20 parts of a preformed diethanolamine salt of dodecyl benzene sulfonic acid. The resulting composition was extremely non-homogeneous and unclear from which solids readily separated out. (Note the observations made in Example l(b) regarding the matter of seeking to prepare the preformed diethanolamine salt of dodecyl benzene sulfonic acid).

Examples l(c) and l(d) are illustrative of compositions falling within the ranges of proportions of the stated ingredients disclosed in the aforesaid Pat. No. 3,239,468 sought to be made simply by mixing together said ingredients. These examples, as well as Examples 1(a) and l(b), show that our polyfunctional essentially active stable liquid detergent compositions are not obtainable by following the procedures described in said Examples 1(a), l(b), l(c) and l(d).

Diethanolamide (l:l Mol Ratio) EXAMPLE 3 Parts Triethanolamine 25 Linear Dodecyl Benzene 35 Sulfonic Acid (88% Active) PLURONIC L-44 22 Laurie Acid Diethanolamide l8 (lzl Mol Ratio) EXAMPLE 4 Parts Diethanolamine l4 Alkyl Benzene Sulfonic Acid 4| (98% Active Branched Chain Alkyl Radical Containing Predominately ll Carbon Atoms) PLURONlC L-64 30 Coconut Oil Fatty Acid Diethanolamide (lzl Mol Ratio) 15 EXAMPLE 5 Parts Diethanolamine 20 Linear Tridecyl Benzene 40 Sulfonic Acid PLURONlC L-64 24 Laurie Acid Diethanolamide 16 (1:1 Mol Ratio) The compositions of Examples 25 are made in the manner described in Example 1. They are all clear stable low foaming liquids under ambient conditions as well as at C.

The liquid detergent compositions of the present invention, as pointed out above, are 100% active or essentially 100% active. In the preparation of said compositions, it is advisable, for optimum results, that no water be deliberately added during such preparation. However, some water may enter into the final liquid detergent compositions by reason of its presence in small proportions in one or more of the ingredients utilized in the preparation of said compositions. In any event, the method of preparation and the selection of ingredients should so be controlled that the water content of the final liquid detergent compositions does not exceed 2% of the total weight of said liquid detergent composi tions. Where reference is made in the claims to essentially 100% active stable liquid detergent composition, it will be understood that said compositions may contain up to 2% water.

The liquid detergent compositions of the present invention, in addition to exhibiting excellent cleaning power for many commercial and consumer requirements including hard surface cleaning, have the important advantages of providing essentially 100% organic surfactant activity with the accompanying economic advantages in shipping and storing, and outstanding stability over prolonged periods of time over a wide temperature range. Said liquid detergent compositions are readily pourable or pumpable, and they can be diluted with water to various commerically acceptable concentrations, forming aqueous solutions which are A. An ethanolamine salt of a member selected from the group consisting of alkyl benzene and alkyl toluene-sulfonic acids in which the alkyl radical contains from 8 to [8 carbon atoms.

B. A non-ionic normally liquid.

water soluble surfactant comprising a polyoxyethylene-polyoxypropylene glycol condensation product C. Fatty acid amides selected from the group consisting of monoethanolamide, diethanolamide and isopropanolamide in which the fatty acid acyl radical contains from l0 to 16 carbon atoms.

the steps which comprise forming a substantially homogeneous solution of the B ingredient with an ethanolamine, then gradually adding thereto, under conditions of agitation, a member selected from the group consisting of alkyl benzene and alkyl toluene-sulfonic acids in which the alkyl radical contains from 8 to l8 carbon atoms, said sulfonic acid being added in an amount essentially to be neutralized by said ethanolamine thereby to form the ethanolamine salt of said sulfonic acid, the temperature of the above mixture being maintained so as not to exceed about C, and then adding under conditions of agitation, said C ingredient until a clear, homogeneous liquid is obtained.

2. In a method of making a polyfunctional essentially 100% active stable liquid detergent composition consisting essentially of the following ingredients in the following percentages by weight:

A. An ethanolamine salt of a member selected front the group consisting of alkyl benzeneand alkyl toluenesulfonic acids in which the alkyl radical contains from 8 to 18 carbon atoms.

B. A non-ionic normally liquid,

water soluble surfactant comprising polyoxyethylene-polyoxypropylene glycol condensation product C, Fatty acid amides selected from the group consisting of monoethanolamide. diethanolamide and isopropanolamide in which the fatty acid acyl radical contains from l0 to 16 carbon atoms.

9 ing, under conditions of agitation, said C ingredient until a clear homogeneous liquid is obtained.

3. A method according to claim 1, wherein the temperature is maintained at below 50C.

4. A method according to claim 1, wherein the alkyl radical of said sulfonic acid contains predominantely from 11 to 15 carbon atoms.

5. A method according to claim 1, wherein the sulfonic acid is a member selected from the group consisting of dodecyland tridecyl-benzene sulfonic acid.

6. A method according to claim 5, wherein the B in gredient constitutes from 22 to 30%, the C ingredient constitutes from 14 to 18%, and the ethanolamine salt of the sulfonic acid constitutes from 52 to 64% of the finished liquid detergent composition.

7. A method according to claim 1, wherein the A ingredient constitutes 45 to 75%, the B ingredient constitutes 15 to 30%, and the C ingredient constitutes 12 to 25%.

8. A method according to claim 4, wherein the A ingredient constitutes 45 to 75%, the B ingredient constitutes 15 to and the C ingredient constitutes 12 to 25%.

9. A method according to claim 1, wherein the A ingredient is an ethanolamine salt of a member selected from the group consisting of dodecyland tridecylbenzene sulfonic acid, and the C ingredient is a C -C fatty acid diethanolamide.

10. A method according to claim 9, wherein the A ingredient constitutes from 52-64%, the B ingredient constitutes from 22 to 30%, and the C ingredient constitutes from 14 to 18%.

11. A method according to claim 9, wherein the A ingredient is a diethanolamine salt of a linear tridecyl benzene sulfonic acid.

12. A method according to claim 9, wherein the A ingredient is a diethanolamine salt of a linear dodecyl benzene sulfonic acid.

13. A method according to claim 2, wherein the ternperature is maintained at below 50C.

14. A method according to claim 2, wherein the alkyl radical of said sulfonic acid contains predominately from I 1 to 15 carbon atoms.

15. A method according to claim 14, wherein the B ingredient constitutes from 22 to 30%, the C ingredient constitutes from 14 to 18%, and the ethanolamine salt of the sulfonic acid constitutes from 52 to 64% of the finished liquid detergent composition.

16. A method according to claim 2, wherein the A ingredient constitutes 45 to the B ingredient constitutes 15 to 30%, and the C ingredient constitutes l2 to 25%.

17. A method according to claim 14, wherein the A ingredient constitutes 45 to 75%, the B ingredient constitutes 15 to 30%, and the C ingredient constitutes 12 to 25%.

18. The product by the method of claim 1.

19. The product by the method of claim 2.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2859182 *Nov 2, 1956Nov 4, 1958Lever Brothers LtdHeavy duty liquid detergent composition
US3232880 *Apr 10, 1961Feb 1, 1966Ultra Chemical Works IncLiquid detergent composition
Non-Patent Citations
Reference
1 *Kastra, Def. Pub. of Serial No. 182,863 filed 9 22 71, Published in 903 O.G. 6 on 10 3 72, Defensive Publication No. T 903,009.
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3984356 *Aug 20, 1975Oct 5, 1976Morton-Norwich Products, Inc.Disodium salt of 8-(4-hexyl-5-carboxycyclohex-2,3-en-1-yl)octanoic acid
US4230605 *Dec 13, 1978Oct 28, 1980Armstrong Cork CompanyAcrylic acid-butyl acrylate-methyl methacrylate terpolymer, monobutyl ether of ethylene glycol, ammonia, reaction product of coconut oil and diethanolamine
US4486329 *Oct 17, 1983Dec 4, 1984Colgate-Palmolive CompanyLiquid all-purpose cleaner
US5167872 *Oct 20, 1986Dec 1, 1992The Procter & Gamble CompanyDetergents having superior grease cutting action
US5789252 *Oct 17, 1996Aug 4, 1998Hitachi, Ltd.Cleaning using detergent, surfactant mixture
US6172035Feb 22, 2000Jan 9, 2001Goldschmidt Rewo Gmbh & Co. KgMixing with surfactants; liquid detergents
US7198351 *Sep 12, 2003Apr 3, 2007Brother Kogyo Kabushiki KaishaInk jet recording apparatus
EP0574277A1 *Apr 30, 1993Dec 15, 1993WitcoUse of an amide as thickening agent, corresponding thickening agent and composition containing the same
Classifications
U.S. Classification510/413, 510/423, 510/496
International ClassificationC11D1/831, C11D11/04, C11D1/38, C11D1/655, C11D1/02, C11D1/72, C11D17/00, C11D1/22, C11D1/52
Cooperative ClassificationC11D1/72, C11D17/0004, C11D1/523, C11D1/22, C11D11/04, C11D1/831, C11D1/655
European ClassificationC11D1/655, C11D1/831, C11D1/52D, C11D11/04, C11D17/00A, C11D1/72, C11D1/22