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Publication numberUS3178366 A
Publication typeGrant
Publication dateApr 13, 1965
Filing dateMay 28, 1962
Priority dateMay 28, 1962
Publication numberUS 3178366 A, US 3178366A, US-A-3178366, US3178366 A, US3178366A
InventorsBrandiff John S, Du Brow Paul L
Original AssigneeArmour & Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Treating compositions for softening fibers
US 3178366 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent 3,178,366 TREATING COMPOSITIONS FOR SOFTENING FIBERS Paul L. Du Brow, Chicago, 11]., and John S. Brandifi, Baltimore, Md, assignors to Armour and Company, Chicago, 111., a corporation of Delaware No Drawing. Filed May 28, 1962, Ser. No. 197,895

7 Claims. (Cl. 252-8.8)

This invention relates to surfactant compositions, and more particularly to fiber-treating compositions for softening fibers and conditioning them for rewetting, etc.

The present application is a continuation-in-part of our copending application Serial No. 787,344, filed January 19, 1959, now abandoned.

The quaternary ammonium salts, being cationic or cation-active agents, are not compatible with anionactive materials. Generally, quaternary ammonium salts are precipitated or rendered inactive by organic anionactive materials such as soaps, alkyl aryl sulfonates, other anionic synthetic detergents, and carboxy methyl cellulose. Also, the polyvalent inorganic anions, such as the phosphates and sulfates, act as precipitants of the quaternary ammonium salts.

This incompatibility is a serious problem, for the effective utilization of the quaternary ammonium salts for their functional benefits is restricted thereby. For example, the quaternary ammonium salts are very effective as softening agents for hair and cellulosic materials such as textiles and tissue paper. However, when the quaternaries are used as the active ingredients for imparting softness to the treated material, traces of any of the aforementioned precipitants, which are usually carried over with the base material from previous treatments, either precipitate or render the quaternary inactive. Consequently, the possible benefits which could be obtained from the ammonium salts are lost.

A second problem arises out of the fact that if a second material is added to the quaternary ammonium salt, it is found that the second material does not aid the quaternary ammonium salts in their function as softening agents but constitute in effect waste material as far as such softening function is concerned, and in addition it is found that such added material does not tend to overcome the waterproofing characteristic of the quaternary ammonium salt, etc.

We have discovered that a surface-active composition consisting of a quaternary ammonium salt in combination with an ethoxylated quaternary ammonium salt meets the above-described problems in that the ethoxylated quaternary ammonium salt adds a full quota of softening activity to that of the first-mentioned quaternary ammonium salt, while at the same time conditioning the textile, etc. material for rewetting. Instead of being an inert or Waste material as far as actively inducing softening is concerned, the ethoxylated quaternary ammonium salt contributes actively to the softening function of the complete composition. Finally, the composition comprising the quaternary ammonium salt and the ethoxylated quaternary ammonium salt is found to be highly compatible with anion-active materials.

Therefore, a principal object of the present invention is to provide surface-active compositions, containing quaternary ammonium salts, which are compatible with anion-active materials. A further object is to provide such compositions in which effective softening effects are produced through the added softening activity provided by the ethoxylated quaternary ammonium salt. A still further object is to provide such a composition which may be employed in the treating of textiles and other fibers for imparting softness thereto, while at the same time conditioning the material for rewetting. Other specific objects and advantages will appear as the details of the invention are set out.

The surface active compositions of the instant invention comprise a quaternary ammonium salt and an ethoX- ylated quaternary ammonium salt containing 15 to moles of ethylene oxide. The compositions may be in the form of free flowing powders or aqueous dispersions. Coloring and perfume may, if desired, be added to the aqueous dispersions.

The quaternary ammonium salt component of the surface active compositions of the invention has the formula wherein R represents benzyl or an alkyl group containing 1 to 3 carbon atoms, R represents benzyl, or an alkyl group containing 1 to 3 carbon atoms, or an alkyl group containing 12 to 18 carbon atoms, R represents an alkyl group containing 12 to 18 carbon atoms, and X represents an anion, such as halogen, acetate, phosphate, nitrite, and methyl sulfate radicals. The carbon chain of the alkyl group containing 12 to 18 carbon atoms may be straight or branched, and saturated or unsaturated. In the preferred embodiments of the invention, this group is derived from long chain fatty acids. The preferred ammonium salt is an alkyl trimethyl ammonium chloride or a dialkyl dimethyl ammonium chloride wherein the alkyl group is derived from hydrogenated tallow.

The ethoxylated quaternary ammonium salts that have peculiar efficacy as the other active component of the compositions of the instant invention are derivatives of ethoxylated tertiary amines and diamines containing 15 to 60 moles of ethylene oxide.

The ethoxylated quaternary ammonium salt derivatives of the tertiary amines have the formula where R represents an alkyl group containing 8 to 18 carbon atoms, R represents methyl, or ethyl, or benzyl radicals, n is an integer from 15 to 60, and X represents an anion, such as halogen, acetate, phosphate, nitrite, and methyl sulfate radicals.

The ethoxylated quaternary ammonium salt derivatives of the ethoxylated diamines have the formula (CH2CH30) XE RIII(CH2) in N R1 R1 (CHzCHzO) where R is an alkyl group containing 8 to 18 carbon atoms, R represents methyl, or ethyl, or benzyl radicals, m is an integer from 2 to 3, the sum of x, y and z is an integer from 15 to 60, and X represents an anion, such as halogen, acetate, phosphate, nitrite, and methyl sulfate radicals.

In the preferred embodiments of the invention, the R groups of the ethoxylated quaternary ammonium salts are derived from long chain fatty acids. Also, the fatty acids can be derived from mixtures, such as are prepared from tallow, coconut oil, and soybean oil. The coco ethoxylated quaternary ammonium salts are preferred for use in the surface-active compositions of this invention.

The effective proportions of the active ingredients of the compositions were found to be that for every part by weight of the quaternary ammonium salt, there should be 0.1 to 2.0 parts by weight of the ethoxylated quaternary ammonium salt. In other words, the weight ratio of the quaternary ammonium salt to ethoxylated quaternary ammonium salt is within the range of from :1 to 1:2. When the components are present in these ratios, the re sulting compositions are stable and may be diluted with water for ease of handling and addition to other aqueous media containing the base materials to be treated therewith. When the compositions the so used, the presence of any of the aforementioned anionic precipitants does not render the quaternary ammonium salt ineffectual. As a consequence thereof, it is now possible to utilize quaternary ammonium salts under conditions that were considered heretofore adverse.

Specific tests on a comparative basis in which fabric is treated with the surfactant compositions described herein and like fabrics treated with quaternary ammonium salts which are not ethoxylated and which are non-ionic, have demonstrated that the former compositions are more effective from the standpoint of softening, while at the same time retaining the rewet characteristic of the treated material. It is believed that this is due to the active contribution in softening characteristics of the ethoxylated quaternary ammonium compound and to some property in the latter compound for retaining the rewet qualities of the textiles, etc.

Having described in detail each of the component compounds constituting the surface-active compositions of the present invention, it therefore becomes convenient to present a number of specific and illustrative completed compositions, the parts being given by weight.

Example I Distearyl dimethyl ammonium chloride 50 Dilauryl methyl polyoxyethylene ammonium chloride containing moles ethylene oxide 50 Example II Dilauryl diethyl ammonium acetate 85 Dimyristyl methyl polyoxyethylene ammonium methyl sulfate containing 40 moles ethylene oxide 15 Example III Dipalmityl dibenzyl ammonium chloride 33 Distearyl benzyl polyoxyethylene ammonium chloride containing 60 moles ethylene oxide 67 Example IV Distearyl dipropyl ammonium phosphate 9O N-capryl, NN-dimethyl polyoxyethylene propylene diammonium chloride containing 45 moles ethylene oxide 10 Example V Stearyl trimethyl ammonium chloride 35 Dicapryl methyl polyoxyethylene ammonium chloride containing 15 moles ethylene oxide 65 Example VI Distearyl dimethyl ammonium methyl sulfate 50 Dilauryl benzyl polyoxyethlene ammonium chloride containing 30 moles ethylene oxide 50 4 Example VII Lauryl trimethyl ammonium methyl sulfate 70 N-lauryl, NN'-diethyl polyoxyethylene ethylene diammonium ethyl sulfate containing 45 moles ethylene oxide 30 Example VIII Palmityl trimethyl ammonium acetate 40 N-stearyl, NN'-dibenzyl polyoxyethylene propylene diammonium chloride containing 60 moles ethylene oxide 60 Example IX Stearyl dimethyl benzyl ammonium nitn'te 50 Dimyristyl methyl polyoxyethylene ammonium methyl sulfate containing 15 moles ethylene oxide 50 Example X Myristyl dimethyl benzyl ammonium chloride Disoya benzyl polyoxyethylene ammonium chloride containing 30 moles ethylene oxide 15 Example XI Stearyl trimethyl ammonium chloride Dicoco ethyl polyoxyethylene ammonium chloride containing 35 moles ethylene oxide 10 Example XII Distearyl dimethyl ammonium methyl sulfate 75 N-soya, NN'-dimethyl polyoxyethylene propylene diammonium methyl sulfate containing 25 moles ethylene oxide 25 Example XIII Palmityl trimethyl ammonium chloride 6O N-tallow, NN-dibenzyl polyoxyethylene propylene diammonium chloride containing 40 moles ethylene oxide 40 Example XIV Distearyl dimethyl ammonium methyl sulfate 5O N-coco, NN'-dimethyl polyoxyethylene ethylene diammonium chloride containing 50 moles ethylene oxide 50 Example XV Comparative tests were carried on to determine the effect of our surfactant composition as to softening and rewet results, using as comparisons the same quaternary compounds with and without non-ionic substitution materials. These tests comprise the present example and the following Examples XVI, XVII and XVIII.

Three parts of Arquad 2HT (dimethyl dihydrogenated tallow quaternary ammonium compound) were combined with one part of Ethoquad 2C/ 25 (quaternary ammonium salt derived from ethylene oxide addition product of dicocoamine containing 15 moles of ethylene oxide). The above compositions based on the weight of the material treated and were added to the final rinse in the treatment for textiles.

A similar test was made employing Arquad 2HT alone. It was found that the composition containing Arquad 2HT and Ethomeen not only provided increased softening but substantially retained the wettability property of the textiles.

Example XVI The test was carried on as described in Example XV above except that the following compositions were compared:

#B. Arquad 2HT (3 parts)-Ethoquad 2C/25 (1 part).

#4. Arquad 2HT (5 parts)Atlas 6-1256 (1 part)- polyoxyethylene sorbital esters of fatty acid)--nonionic.

The test results showed #B to have increased softening and rewet effect.

Example XVII Comparative tests were made as described in Example XV except that the following materials were compared: #1. Arquad 2HT (3 parts)-Ethoquad 2HT/ 25 (1 part). #2. A-rquad 2HT (3 parts)-Ethoquad 2HT/25 /3 part)nony1 phenol plus 9 moles ethylene oxide part) (non-ionic).

Ethoquad 2HT/ 25 has the following formula:

in which R is hydrogenated tallow.

In the above test, #1 was found to provide greater softening than composition #2, the addition of the nonionic in #2 reducing softening. The rewet qualities were about equal.

Example XVIII Tests were carried on as described in Example XV except that the following compositions were tested:

#1. Arquad 2HT (3 parts)Ethoquad 2C/50 (1 part). #2. Arquad ZHT (3 parts)--Ethomid HT/ 15 (1 part).

Ethomid HT/ 15 has the following formula:

in which R is hydrogenated tallow and x plus y equals 5.

Ethornid is completely non-ionic. Its substitution reduced softening. #2 composition had poor softening and no rewet, while #1 composition had excellent softening and good rewet.

The surface active compositions of the instant invention are particularly useful in the manufacture of textiles and tissue paper for improving surface softness. Each of the above compositions was tested at concentrations of from 0.1% to 0.3% based on the weight of the material treated. For textiles, the surface active composition was added to the final rinse. In the manufacture of tissue paper, the compositions were dissolved in hot water and then added to the pulp in the beater with other paper ingredients. The mixture was digested for about one-half hour prior to felting. In all cases, the presence of trace precipitants, hereinbefore set forth, in the aqueous media did not affect adversely the quaternary ammonium salt. Surface smoothness was obtained with all compositions. When the same quaternary salts were used alone, the material was insufficiently treated and the desired degree of surface softness was not obtained.

Additional tests were made to determine the efficacy of the surface active compositions of the instant invention for effecting softening of hair and clothes after washing with conventional soaps and/or detergents with or without water softening agents being present during the washing and intermediate rinsing steps. The fabric or hair softener is usually added to the final rinse. However, the intermediate rinses usually do not remove all of the washing of clean ng agents or Water softeners prior to the final rinse. Consequently, traces of anionic materials are usually present during the final rinse. Heretofore, the use of quaternary ammonium salts under these conditions has not been satisfactory. The cationic quaternary ammonium salts reacted with anionic materials to form insoluble products. The tests of each of the above compositions in laundry equipment showed that the presence of trace amounts of the cleaning agents with or without water softening materials, such as the polyphosphates, was not detrimental to the effectiveness of the quaternary ammonium salt. Here again, the desired degree of softness was only obtainable when the ethoxylated quaternary ammonium salt was present.

' will be apparent to those skilled in the art that this in- Aqueous dispersions were prepared from the compositions hereinbefore set forth so that the active components were present at a 0.15% concentration. These dispersions were used as hair rinses and found to be satisfactory without precipitation of the quaternary salt which did occur when the ammonium salt was used as the sole softening agent.

While in the foregoing specification various embodiments of this invention have been set forth and many details thereof elaborated for the purpose of illustration, it

vention is susceptible to other embodiments and that many of these details can be varied widely without departing from the basic concept and spirit of this invention.

We claim:

1. A treating composition for softening fibers and conditioning them for rewetting, consisting essentially of a quaternary ammonium salt having the formula wherein R is selected from the group consisting of an alkyl group containing 1 to 3 carbon atoms and benzyl, R is selected from the group consisting of an alkyl group containing 1 to 3 carbon atoms, an alkyl group containing 12 to 18 carbon atoms, and benzyl, R is an alkyl group containing 12 to 18 carbon atoms, and X is an anion; and an ethoxylated quaternary ammonium salt selected from the group consisting of compounds having the formula wherein R is an alkyl group containing 8 to 18 carbon atoms, R, is selected from the group consisting of methyl, ethyl and benzyl, n is an integer from 15 to 60, m is an integer from 2 to 3, the sum of x+y+z is an integer from 15 to 60, and X is an anion; the weight ratio of the first mentioned salt to the second mentioned salt being from 10:1 to 1:2.

2. The composition of claim 1 in which the first-mentioned ammonium salt is selected from the group consisting of an alkyl trimethyl ammonium chloride and a dialkyl dimethyl ammonium chloride, in both of which the alkyl group is derived from hydrogenated tallow.

3. A treating composition for softening fibers and conditioning them for rewetting, consisting essentially of distearyl dimethyl ammonium methyl sulfate and dilauryl benzyl polyoxyethylene ammonium chloride containing 15 to 60 moles ethylene oxide, the weight ratio of said sulfate to said chloride being from 10:1 to 1:2.

4. A treating composition for softening fibers and conditioning them for rewetting, consisting essentially of distearyl dimethyl ammonium chloride and dilauryl methyl polyoxyethylene ammonium chloride containing 15 to 60 moles ethylene oxide, the weight ratio of said distearyl compound to said dilauryl compound being from 10:1 to 1:2.

5. A treating composition for softening fibers and conditioning them for rewetting, consisting essentially of stearyl trimethyl ammonium chloride and dicoco ethyl polyoxyethylene ammonium chloride containing 15 to 60 moles ethylene oxide, the weight ratio of said stearyl compound to said dicoco compound being from 10:1 to 1:2.

6. A treating composition for softening fibers and conditioning them for rewetting, consisting essentially of palmityl trimethyl ammonium chloride and N-tallow,

7 NN'-dibenzyl polyoxyethylene propylene diammonium chloride containing 15 to 60 moles ethylene oxide, the weight ratio of said palmityl compound to said N-tallow compound being from 10:1 to 1:2.

7. A treating composition for softening fibers and conditioning them for rewetting, consisting essentially of distearyl dimethyl ammonium methyl sulfate and N-soya, NN'-dimetl1yl polyoxyethylene propylene diammonium chloride containing 15 to 60 moles ethylene oxide, the weight ratio of said sulfate to said chloride being from 10:1 to 1:2.

References Cited by the Examiner UNITED STATES PATENTS Schoeller et a1. 260-404.4 XR

Lambert 1252-152 Welles et al. 2528.8

Hall 252-818 Mark 252357 Brown et al 2528.8

10 JULIUS GREENWALD, Primary Examiner.

ALBERT T. MEYERS, Examiner.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3325404 *Sep 19, 1963Jun 13, 1967Millmaster Onyx CorpComposition for simultaneously laundering and softening fabrics
US3498816 *Aug 29, 1967Mar 3, 1970Du PontFlock coating composition
US3501335 *Nov 26, 1965Mar 17, 1970Lever Brothers LtdFabric conditioner
US3850818 *Sep 19, 1972Nov 26, 1974Kao CorpAntistatic softening composition containing a quaternary ammonium salt and a ethenoxy quaternary ammonium salt
US3915867 *Apr 24, 1973Oct 28, 1975Stepan Chemical CoDomestic laundry fabric softener
US3959157 *Jun 4, 1973May 25, 1976Colgate-Palmolive CompanyNon-phosphate detergent-softening compositions
US4239634 *May 14, 1979Dec 16, 1980Exxon Research & Engineering Co.Lubricating oil containing a surface active agent
US4548744 *Jul 22, 1983Oct 22, 1985Connor Daniel SEthoxylated amine oxides having clay soil removal/anti-redeposition properties useful in detergent compositions
US4551506 *Dec 23, 1982Nov 5, 1985The Procter & Gamble CompanyCationic polymers having clay soil removal/anti-redeposition properties useful in detergent compositions
US4636330 *Jan 25, 1985Jan 13, 1987Lever Brothers CompanyPerfume depositing detergents containing perfume in a particulate matrix of a cationic compound
US4659802 *Nov 22, 1983Apr 21, 1987The Procter & Gamble CompanyCationic compounds having clay soil removal/anti-redeposition properties useful in detergent compositions
US4661288 *Mar 8, 1985Apr 28, 1987The Procter & Gamble CompanyZwitterionic compounds having clay soil removal/anti/redeposition properties useful in detergent compositions
US4664848 *Nov 22, 1983May 12, 1987The Procter & Gamble CompanyDetergent compositions containing cationic compounds having clay soil removal/anti-redeposition properties
US4676921 *Dec 23, 1982Jun 30, 1987The Procter & Gamble CompanyDetergent compositions containing ethoxylated amine polymers having clay soil removal/anti-redeposition properties
Classifications
U.S. Classification510/521
International ClassificationD06M13/00, D06M13/432
Cooperative ClassificationD06M13/432
European ClassificationD06M13/432