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Publication numberUS2060568 A
Publication typeGrant
Publication dateNov 10, 1936
Filing dateJun 20, 1935
Priority dateJun 23, 1934
Also published asDE670813C
Publication numberUS 2060568 A, US 2060568A, US-A-2060568, US2060568 A, US2060568A
InventorsGraenacher Charles, Sallmann Richard
Original AssigneeSoc Of Chemical Ind
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Assisting agents for the textile industry
US 2060568 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

Patented Nov. 10, 1936 iED STATES ASSISTING AGENTS FOR THE TEXTILE INDUSTRY Charles Graenacher and Richard Sallmann, Basel, Switzerland, assignors to firm Society of Chemical Industry in Basic, Basel, Switzerland No Drawing.

Application June 20, 1935, Serial No. 27,609. In Switzerland June 23, 1934 15 Claims. (Ci. 8-20) 'It is known that when tertiary amines are treated with suitable oxidizing agents they may be converted into so-cal1ed tertiary amine-oxides.

Hitherto these products have only been described in scientific literature and there has been no 5 reason to suppose that they could be applied as assistants in the textile industry.

It has now been found that certain of these tertiary amine-oxides, i. e. those which, due to their molar magnitude, are not soluble in mercerizing baths, or only sparingly soluble, but which can be dissolved in mercerizing baths with aid of so-called solubility-promoting agents, may be used for the production of excellent wetting agents for mercerizing liquors. In order to produce such wetting agents for mercerizing baths,

it is only necessary to mix these amine oxides with, the so-called solubility-promoting agents.

To the compositions of matter thus obtained there may be added further substances, such as, for example ether alcohols, for instance, glycolmonobutylether, glycerine-monoalkylether and glycerine-dialkylether.

As amine-oxides which come into consideration for carrying out the present invention there may i be named amine-oxides derived from tertiary amines which contain at least one radical comprising 3 carbon atoms, such as, for example, the propyldimethylamine-oxide oi the formula- CHPGHPCHPI1I=O the propyldiethylamine-oxide of the formula- CHI YOHr-CHz-OHr-N=O I 13' 40 the butyldimethylamine-oxide oi the formula- CH: CH:-'CHr-CHr-CHr-I T=O I (3B4 the dipropylmethylamine-oxide of the formula-- CHr-CHr-CH:

, OHr-CHr-CHg-N=O 1 HI the butyldiethylamine-oxide of the formula- CHrCHr-CH:CH:N- O

the li-butylpiperidine -oxide oi the formula- CHr-C cnroar-cnrcnrn OKs-CH,

the dimethylcyclohexylamine-oxide of the formu- 1a W V CH:

CIiCH: CH1

the diethylcyclohexylamine-oxide of the formu- 1a- CHr-OHi CHz I 10 the methylhydroxyethylcyclohexylamine-oxide of CHP-CHI III Hr-CHr-OH 20 the phenyldimethylamine-oxide of the formulathe benzylpiperidine-oxide of the formula QHr-CH:

CHz-CH: 30

etc. All these compounds are oxides derived from such tertiary amines which contain not more than 12 carbon atoms and which contain at least one radical which comprises at least 3 carbon atoms. Of these amine-oxides, those are particu- 35 larly valuable which are derived from non-aromatic tertiary amines; further those non-aromatic tertiary amines which contain at least one radical comprising 4 to 6 carbon atoms, But if use is made of amine-oxides which are derived 40 from tertiary amines'containing higher aliphatic radicals, such as, for example, the dodecyldimethylamine oxide, no compositions of matter are obtained which are useful as wetting agents, for mercerizing baths, since the solubility-promot- 45 ing agent is no longer capable of keeping such highly molecular amine-oxides in solution in mercerizing baths. The low molecular amineoxides, such as trimethylamine-oxide or triethylamine-oxide are useless, since as such they are too easily soluble in the mercerizing baths.

Solubility-promoting agents. 1. e. products which have been selected from a group of com-'- pounds consisting of phenols, or highly suli'onated 55 oils. and which have the property of increasing the solubility of organic compounds in mercerizing baths, are for example, phenol itself, the various cresols, crude cresol, phenols substituted in the aromatic nucleus by alkyl radicals commercerization.

prising more than one carbon atom such as the alkylor propyl-phenols, highly sulionated castor oil and the like. The following examples illustrate the invention, the parts being by weight:-

Example 1 25 parts of butyldimethylamine-oxide are mixed with 75 parts of crude cresol. The mixture may be used forthwith as an assistant in tained, if instead of '75 parts of crude cresol a mixture of 65 parts of crude cresol, and 10 parts of glacial acetic acid is used.

Example 2 To a memorization liquor '"(sodium hydroxide solution of 30 B.) there is added, per litre,

Li uor Liquor Seconds wit out with I addition addition The liquor to which the addition has been made remains quite clear even on long standing and after 72 hours has the same shrinkage values as those recorded with the liquor immediately after addition has been made.

Example 3 To the mercerizing liquor there is added, per litre, 5 grams of a mixture consisting of 38.5 parts of dimethylaniline-oxide and 61.5 parts of crude cresol. solved in the mercerizing liquor. The tests made in the same manner as described in Example 2 'gave the following shrinkage values:-

- Li 1101' Liquor Seconds wit out wit addition addition A like mixture, which contains dimethylaniline instead of dimethylaniline-oxide is completely useless on account of the immediate separation of the base.

For the foregoing amine-oxides there may be substituted n-butyl-piperidine-oxide, benzylpiperidine oxide, dimethyl-cyclo-hexylamine-oxide, diethylcyclohexyiamine oxide, methyloxyethylcyclohexylamine-oxide or these, or the like.-

What we claim is:-

A stable, clear solution is oh This addition remains fully disaooasoa 1. A composition of matter comprising a solubility-promoting agent and a tertiary amine oxide which is sparingly soluble in mercerizing baths, but which is soluble in mercerizing baths with the aid of a solubility-promoting agent selected from the group consisting of phenols and highly sulfonated oils.

2. A composition of matter comprising crude cresol and an amine-oxide which is sparingly soluble in mercerizing baths, but which is soluble in mercerizing baths with the aid of crude cresol.

3. A'composition of matter comprising a solubility-promoting agent selected from the group consistingof phenols and highly sulfonated oils and a tertiary amine-oxide derived from a nonaromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.

4. A composition of matter comprising a phenol and a tertiary amine-oxide derived from a nonaromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.

5. A composition of matter comprising crude cresol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.

6. A composition of matter comprising a solubility-promoting agent selected from the group consisting of phenols and highly sulfonated oils and a tertiary amine-oxide derived from a nonarornatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.

'7. A composition 01 matter comprising a phenol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.

8. A composition of matter comprising crude cresol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.

9. A composition of matter comprising a phenol and butyldimethylamine-oxide.

10. A composition of matter comprising crude cresol and butyldimethylamine-oxide.

11. A composition of matter consisting of a mixture of 70 to 95 parts of a phenol and 5 to 30 parts of butyldimethylamine-oxide.

12. A composition of matter consisting of a mixture of 70 to 95 parts of crude cresol and 5 to 30 parts of butyldimethylamine-oxide.

13. A composition oi matter comprising a solubility-promoting agent selected from the group consisting of phenols. and highly sulfonated oils and dimethylcyclohexylamine-oxide.

14. A composition oi matter comprising a phenol and dimethylcyclohexylamine-oxide.

15. A composition of matter consisting of a mixture of about 85 to 95 parts of crude cresol 41.21% 5' to 15 parts of dimethylcyclohewlamineo e.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2999068 *Apr 27, 1959Sep 5, 1961Procter & GamblePersonal use detergent lotion
US3001945 *Apr 29, 1959Sep 26, 1961Procter & GambleLiquid detergent composition
US3085982 *Apr 22, 1959Apr 16, 1963Procter & GambleLiquid detergent composition
US3086943 *Jun 10, 1959Apr 23, 1963Procter & GambleShampoo containing amine oxide
US3179598 *Jul 3, 1961Apr 20, 1965Procter & GambleDetergent composition
US3179599 *Jul 3, 1961Apr 20, 1965Procter & GambleDetergent composition
US3194840 *Dec 18, 1961Jul 13, 1965Procter & GambleN, n-diloweralkyl, 1, 1-dihydrogen perfluoroalkyl amine oxides
US3197509 *Dec 21, 1961Jul 27, 1965Procter & GambleDiamine dioxide compounds
US3202714 *Dec 4, 1961Aug 24, 1965Procter & GambleOxy containing tertiary amine oxides
US3223647 *Apr 20, 1959Dec 14, 1965Procter & GambleMild detergent compositions
US3249587 *Sep 29, 1961May 3, 1966Gen ElectricMixture of epoxy resin and a tertiary amine oxide
US3317430 *May 5, 1960May 2, 1967Lever Brothers LtdDetergent compositions
US3441611 *Dec 4, 1961Apr 29, 1969Procter & GambleHydroxyalkylamine oxide detergent compounds
US3447956 *Sep 2, 1966Jun 3, 1969Eastman Kodak CoProcess for strengthening swellable fibrous material with an amine oxide and the resulting material
US3449430 *Jun 20, 1961Jun 10, 1969Henkel & Cie GmbhAmino oxides
US3508941 *Jan 13, 1969Apr 28, 1970Eastman Kodak CoMethod of preparing polymers from a mixture of cyclic amine oxides and polymers
US4325821 *Feb 4, 1981Apr 20, 1982Sherex Chemical Company, Inc.Amine oxide promoters for froth flotation of mineral ores
US5824115 *Apr 5, 1996Oct 20, 1998Kao CorporationMethod for improving cellulose fiber
US6500215Jul 11, 2000Dec 31, 2002Sybron Chemicals, Inc.Utility of selected amine oxides in textile technology
WO1981000527A1 *Jul 3, 1980Mar 5, 1981Sherex ChemAmine oxide promoters for froth flotation of mineral ores
Classifications
U.S. Classification8/127, 516/203, 546/192, 564/297, 564/299, 564/298, 546/184, 516/DIG.700
International ClassificationD06M13/152, D06M13/388, D06M11/38
Cooperative ClassificationD06M13/152, Y10S516/07, D06M13/388, D06M11/38
European ClassificationD06M11/38, D06M13/152, D06M13/388