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Publication numberUS3897208 A
Publication typeGrant
Publication dateJul 29, 1975
Filing dateJun 9, 1969
Priority dateJun 9, 1969
Also published asDE2028115A1, DE2028352A1, US3925009
Publication numberUS 3897208 A, US 3897208A, US-A-3897208, US3897208 A, US3897208A
InventorsBarry M Shay
Original AssigneeIci America Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Textile treating compositions, process of treating textiles, and textile articles
US 3897208 A
Abstract
Disclosed are textile treating compositions comprising (1) a methylolated carbamate which is an ester of N-methylol carbamic acid or N,N-dimethylol carbamic acid and an ethylene oxide adduct of a fatty acid, fatty alcohol, fatty acid ester of a polyol, fatty amine, or fatty acid amide and (2) a durable-press agent. The textile treating compositions may be applied to textile material to improve the physical characteristics thereof; for example, durable press properties, wrinkle-resistance, tear strength, hand and abrasion resistance.
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[451 July 29,1975

1 1 TEXTILE TREATING COMPOSITIONS,

PROCESS OF TREATING TEXTILES, AND TEXTILE ARTICLES [75} Inventor: Barry M. Shay, Wilmington, Del.

[73] Assignee: ICI United States lnc., Wilmington,

Del.

[22] Filed: June 9, 1969 [21] App1.No.: 831,770

[52] US. Cl. ..8/187;8/115.6;8/115.7; 8/D1G. 4; 8/D1G. 21; 260/29.4 R; 260/404; 260/404.5; 260/468 L; 260/482 B; 260/482 C [51] Int. Cl. D06m 15/54; D06m 15/58 [58] Field of Search 8/116.3, 115.6; 260/404,

260/404.5, 482 B, 482 C, 29.4 R

[56] References Cited UNITED STATES PATENTS 1,959,930 5/1934 Schmidt et a1 260/404 1,970,578 8/1934 Schoeller et a1 260/404 2,002,613 5/1935 Orthner et a1. 260/404 2,157,362 5/1939 Ulrich et a1... 260/482 C 2,184,008 12/1939 Dickey et al.. 260/482 C 2,197,479 4/1940 Meigs 260/482 C 2,218,939 10/1940 Steindorff 260/482 C 2,477,346 7/1949 Pikl 260/482 C 2,518,267 8/1950 Baird et a1. 260/404.5 2,585,826 2/1952 Olsen 260/482 B 2,998,445 8/1961 Stewart et a1. 260/482 C 3,427,332 2/1969 Allen et a1. 260/404.5 3,524,876 8/1970 Gregson 8/187 FORElGN PATENTS OR APPLICATIONS 697,315 9/1953 United Kingdom 1,123,677 8/1968 United Kingdom 1,128,812 10/1968 United Kingdom 610,393 12/1960 Canada Primary Examiner-George F. Lesmes Assistant Examiner-J. Cannon [57] ABSTRACT Disclosed are textile treating compositions comprising (1) a methylolated carbamate which is an ester of N- methylol carbamic acid or N,N-dimethy1ol carbamic acid and an ethylene oxide adduct of a fatty acid, fatty alcohol, fatty acid ester of a polyol, fatty amine, or fatty acid amide and (2) a durable-press agent. The textile treating compositions may be applied to textile material to improve the physical characteristics thereof; for example, durable press properties, wrinkle-resistance, tear strength, hand and abrasion resistance.

16 Claims, No Drawings TEXTILE TREATING COMPOSITIONS, PROCESS OF TREATING TEXTILES, AND TEXTILE ARTICLES This invention relates to novel textile treating com positions. More particularly, this invention relates to textile treating compositions comprising a methylolated carbamate and a durable-press agent. This invention further relates to a process of treating textile materials to improve the physical characteristics thereof, such as durable press, wrinkle resistance, tear strength, hand, and abrasion resistance, in such a way that the improvements are not destroyed by laundering, drycleaning, or similar operations. This invention further relates to textile materials having improved physical properties.

During the past several years, the textile industry has become involved in the durable press treatment of textile materials. The treatment is carried out by impregnating the textile material with an aqueous solution or dispersion of a textile-reactive, cross-linking, durablepress agent and then heating the impregnated material for curing. This treatment stabilizes the fibers in the configuration they had in the textile during the curing. Consequently, when a stress is applied to the treated textile and then released, the textile tends to return to the original configuration. This results in a textile material exhibiting durable press properties.

The cross-linking treatment, however, has an adverse effect on the tear strength, hand, and abrasion resistance properties of the textile material. Thus, the crosslinked textile material, although exhibiting the beneficial characteristics of durable press behavior, has poor abrasion resistance, poor hand, and poor tear strength.

It is, accordingly, an object of this invention to provide novel textile treating compositions for application to textile materials to impart thereto durable press properties, tear strength, hand, and abrasion resistance properties and which will adhere to the textile materials through numerous laundering and drycleaning cycles.

It is another object of this invention to provide a process for treating textile material in such a manner that it has durable press properties, excellent abrasion resistance, hand, and tear strength.

It is another object of this invention to provide textile materials having improved durable press properties, hand, tear strength, and abrasion resistance.

The foregoing objects and still further objects are accomplished in accordance with the present invention by providing a textile treating composition comprising a mixture or blend of a textile-reactive, cross-linking, durable-press agent and a methylolated carbamate.

The amounts of durable-press agent and methylolated carbamate present in the textile treating compositions of this invention may vary over a rather wide range and will depend somewhat on the particular durable-press agent and methylolated carbamate selected and on the particular textile material to be treated therewith. In general, the textile treating composition of this invention may contain from about 40 to 96 percent, preferably from about 55 to about 65 percent, by weight of the durable press agent and from about 60 to 4 percent, preferably from about 45 to about 35 percent, by weight of the methylolated carbamate, based on the total weight of durable press agent and methylol ated carbamate.

Durable-press agents useful in the preparation of textile treating compositions in accordance with the present invention include both monomer and polymers which when applied to a textile material and cured under conditions conventional in the art undergo reaction with the textile material and impart durable press and/or wrinkle resistant characteristics to the textile material.

Durable-press agents that are preferred when practicing the present invention are the aminoplast resins. These nitrogen containing resins, when applied to textile materials and heated at temperatures from C. to 200C. in the presence of a catalyst, react with the textile material and become chemically attached thereto. Exemplary of the aminoplast resins that may be employed according to the present invention are the ethylene ureas, for example, dimethylol dihydroxy ethylene urea, dimethylol ethylene urea, ethylene urea formaldehyde, and hydroxy ethylene urea formaldehyde; urea formaldehydes, for example, propylene urea formaldehyde and dimethylol urea formaldehyde; melamine formaldehyde, for example, tetramethylol melamines, and pentamethylol melamines; carbamates, for example, alkyl carbamate formaldehydes; formaldehyde-acrolein condensation products; alkylol amides, for example, methylol formamide and methylol acetamide; acrylamides, for example, N-methylol acrylamide, N-methylol methacrylamide, and N-methylol-N- methacrylamide; diureas, for example, trimcthylol acetylene diurea and tetramethylol-acetylene diurea; triazones, for example, dimethylol-N-ethyl traizone; haloacetamides', urons, for example, dimethylol uron and dihydroxy dimethylol uron. Mixtures of aminoplast resins may also be used.

Further illustrative examples of durable-press agents useful in the preparation of the textile treating compositions of this invention include aldehydes, for example, formaldehyde, glyoxyl, and B-hydroxy adipaldehyde; epoxides, for example, ethylene glycol diglycidyl ether and vinylcyclohexene dioxide; ethyleneimine derivatives, for example, bisaziridenylcarbonyl, and tris(laziridinyl) phosphine oxide; chlorohydrins; sulfone derivatives, for example, divinyl sulfone and bis(hydroxyethyl) sulfone; and sulfonium salts, for example, disodium tris(B-sulphatoethyl) sulfonium inner salt.

Methylolated carbamates useful in the preparation of textile treating compositions in accordance with the present invention are methylolated carbomates of an ethylene oxide adduct selected from the group consisting of I. an ethylene oxide adduct of a fatty acid containing from 12 to 28 carbon atoms,

2. an ethylene oxide adduct of a fatty alcohol containing from 12 to 28 carbon atoms,

3. an ethylene oxide adduct of a fatty amine containing from l2 to 28 carbon atoms,

4. an ethylene oxide adduct of an amide of a fatty acid containing from 12 to 28 carbon atoms,

5. an ethylene oxide adduct of an ester of a fatty acid containing from 12 to 28 carbon atoms and a polyhydric alcohol containing from 3 to 6 carbon atoms and from 2 to 6 hydroxyl groups, and

6. a partial ester of a fatty acid containing from 12 to 28 carbon atoms and an adduct of ethylene oxide and a polyhydric alcohol containing from 3 to 6 carbon atoms and from 2 to 6 hydroxyl groups.

The methylolated carbamates of this invention contain at least one oxyethylene group, at least one fatty group containing from 12 to 28 carbon atoms, and at least one O R, l 0 C H OH group wherein R is hydrogen or methylol. Accordingly, the carbamates of this invention may be described as esters of N-methylol carbamic acid and N,N- dimethylol carbamic acid and the above defined ethylene oxide adducts.

The methylolated carbamates of this invention may be prepared by reacting one or more of the ethylene oxide adducts described herein with urea or with an alkyl carbamate such as ethyl or methyl carbamate and then reacting the resulting carbamate with formaldehyde. The reactions are illustrated by the following equations:

organic OH H,,C -O NH2 HHC OH organic -OiNl-l,

organic OH HgNiNHg NH organic i NH organic O i- NH HCHO v E /CH,OH organic C N\ organic O (I NH ZHCHO" 0 organic O l MCI-L0H) These two well-known methods of forming carbamates are described in detail in the article by Adams et al. published in Chemical Reviews, Volume 65, pages 567-602, 1965. The disclosure of this article is hereby incorporated into this appliction by reference. Briefly, the reaction may be carried out by heating a mixture of urea or alkyl carbamate and an ethylene oxide adduct to a temperature in the range of from about ll0C. to about 200C. Catalysts, such as heavy metal salts of weak organic acids, zinc chloride, cobalt chloride, lead acetate, cupric acetate, boron trifluoride, aluminum isopropoxide, dibutyltin dilaurate, and dibutyltin oxide may be used to shorten the reaction time and increase the yield. The degree of carbamylation may be controlled by varying the amounts of ethylene oxide adduct and carbamylating agent used. For example, the reaction of three mols of urea with one mol of an ethylene oxide adduct containing six hydroxyl groups will result in the formation of a carbamate containing an average of three carbamate groups. Methylol groups are then introduced by reacting the carbamate with formaldehyde, paraformaldehyde, or other convenient source of formaldehyde.

The ethylene oxide adducts which may be used to prepare the carbamates of this invention are known compounds. US. Pat. Nos. 1,959,930; l,970,578; and 2,002,6l3, the disclosures of which are hereby incorporated hereinto by reference, disclose the preparation of ethylene oxide adducts which may be used to prepare the carbamates of this invention. Briefly, the ethylene oxide adducts may be prepared by reacting ethylene oxide with the appropriate fatty alcohol, fatty acid, fatty amine, fatty amide, or ester of fatty acid and a polyol or by reacting a fatty acid with an ether of ethylene oxide and a polyol.

Fatty alcohols which may be used to prepare the ethylene oxide adducts include saturated or unsaturated, straight or branched chain fatty alcohols having from 12 to 28 carbon atoms. A preferred group of fatty alcohols may be represented by the formula ROH wherein R is an alkyl group or an alkenyl group containing from l2 to 28 carbon atoms. illustrative exmaples of such fatty alcohols include dodeeanol, dodecenol, tetradecanol, tetradecenol, hexadecanol, hexadecenol, octadecanol, octadecenol, eicosanol, eicosenol, docosanol, docosenol, tetracosanol, tetracosenol, hexacosanol, hexaeosenol, octacosanol, and octacosenol.

Fatty acids which may be used to prepare the ethylene oxide adducts include saturated and unsaturated fatty acids having from 12 to 28 carbon atoms. A preferred group of fatty acids may be represented by the formula ROH wherein R is an acyl group containing from l2 to 28 carbon atoms. Illustrative examples of such fatty acids include lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, oleic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid, lauroleic acid myristoleic acid, palmitoleic acid, oleic acid, linolenic acid, ricinoleic acid, eicosenoic acid, docosenoic acid, and tetracosenoic acid.

Fatty amines which may be used to prepare the ethylene oxide adducts include primary or secondary, saturated or unsaturated amines containing at least one fatty group having from 12 to 28 carbon atoms. A preferred group of fatty amines may be represented by the formula R R NH wherein R is an alkyl or alkenyl group containing from 12 to 28 carbon atoms and R is hydrogen or an alkyl or alkenyl group containing from 1 to 28 carbon atoms. Illustrative examples of such fatty amines include dodecylamine, hexadecylamine, octadecylamine, eicosylamine, pentacosylamine, didodecylamine, dioctadecylamine, N- mcthyldodecylamine, N-ethyloctadecylamine, AR-

MEEN TD, ARMEED SD eocoamine, oleyl amine.

Fatty amides which may be used to prepare the ehtylene oxide adducts include fatty amides having at least one fatty group containing from 12 to 28 carbon atoms. A preferred group of fatty amides may be represented by the formula RNR'H wherein R is an acyl group containing from 12 to 28 carbon atoms and R'is hydrogen or an alkyl or alkenyl group containing from I to 28 carbon atoms. Illustrative examples of such fatty amides include dodecanamide, hexadecanamidc, octadecanamide, octadecenarnide, eicosanamide, pentacosanamide, N-methyl-octadecanamide, N-stearylhydroxystearamide, dodecenamide, N-oleyloctadecanamide, N-oleyl-pentadecenamide, and N- lauryl-stearamide.

Polyols which may be used to prepare the ethylene oxide adducts include polyols having from 3 to 6 carbon atoms and from 2 to 6 hydroxyl groups. A preferred group of polyols may be represented by the formula R(Ol-l) wherein R is an aliphatic group having from 3 to 6 carbon atoms and m is from 2 to 6. lllustra tive examples of these polyols include propylene glycol, hexamethylene glycol, butanediol, isosorbide, isomannide, glycerine, hexanetriol, pentaerythritol, erythritol, sorbitan, mannitan, sorbitol, mannitol, dulcitol, quercitol, inositol, and arabitol.

The methylolated carbamates of this invention may be characterized by a formula selected from the group consisting of the following generalized formulae wherein identical symbols have identical signification:

and 4. (R O),,D wherein R is an alkyl group containing from 12 to 28 carbon atoms, an alkenyl group containing from l2 to 28 carbon atoms, an acyl group containing from l2 to 28 carbon atoms, or the group resulting from removing a hydroxyl group from lanolin,

R, is hydrogen or CH OH,

n is an integer from I to 150,

R is the group remaining after removing all the hydroxyl groups from a saturated, aliphatic alcohol having from 3 to 6 carbon atoms and from 2 to 6 hydroxyl groups,

at is an integer from 2 to 6,

each

A is independently selected from the group consisting of hydrogen, alkyl groups containing from l2 to 28 carbon atoms, alkenyl groups containing from 12 to 28 carbon atoms, acyl groups containing from 12 to 28 carbon atoms,

and +CHg'CH-g'O+nRu wherein R is hydrogen, an acyl group containing from l2 to 28 carbon atoms, or

with the proviso that at least one A contains an alkyl, alkenyl, or acyl group containing from [2 to 28 carbon atoms, at least one A contains a +CH CH2O-l-R6 group. and at least one A contains group,

with the proviso that at least one B contains a group, R is H or with the proviso that at least one R is y is a number from l to 5, and

D is the group remaining after removing all the hydroxyl groups from an adduct of ethylene oxide and an ester of a fatty acid having from 12 to 28 carbon atoms and a polyol having from 2 to 6 hydroxyl groups and from 3 to 6 carbon atoms.

In order that those skilled in the art may better undcrstand the nature and preparation of the methylolated carbamates, the following examples are given. These examples are set forth solely for the purpose of illustration and any specific enumeration of details contained therein should not be interpreted as expressing limitations of this invention. All parts and percentages are by weight, unless otherwise stated.

The following procedure is employed in Examples 1 using other durable press agents and methylolated carbamates for those recited. The textile treating composition of Example 32 is a preferred embodiment of this invention.

to '27. The indicated amounts of urea and eth lene EXAMPLE 32 oxide adduct are charged to a three-necked flask and the contents of the flask heated to the indicated temperaturetor the indicated length of time. The reaction Cmbamale of Example 24 product is filtered to remove any unreacted urea. The Dimethylol dihydroxy ethylene urea (10% filtrate is the carbamate of the starting ethylene oxide l0 adduct. The recovered carbamate is then mixed with a EXAMPLE 33 37 percent aqueous solution of formaldehyde and a heated to about 50 C. for 10 to 12 hours to form the Ca'bamate of Example I methylolated carbamate. l.3-Dimethylol hexahydro-pyrimidinonei 55% Temper- Example Grams of Grams of ature Time Carbamate" Methylol Number Ethylene Oxide Adduct Adduct Urea C. Hours Hydroxy Carbamate l Po1yoxyethylcne(4) lauryl alcohol 200 35.6 l55 l3 0.67 1.2 2 Dioleate of polyoxyethylene(20)sorbitol 60 5.8 I 9 0.62 [.2 3 Polyoxyethylene( I5 )castor oil 500 5.8 I60 6 0.66 1.2 4 Polyoxyethylene(20)tall oil 200 l3.4 160 9 0.6 1.2 5 Polyoxyethylene(20)ether of glycerol dioleate 106 5.3 ISO-I60 5% 0.69 1.2 6 Polyoxyethylene( 20)ether of lanolin 200 7.8 I60 7 027 L2 7 Polyoxyethylene(20)ether of glycerol monopalmitate 200 1 -160 7% 0.83 I .2 8 Polyoxyethylene( 40 )-N-stearyl- I 2- hydroxystearamide 200 3.5 160 6% 0.42 I .2 9 Polyoxyethylene(20)ether of sorbitan monooleate 200 I7 1 55-160 6% 0.64 I .2 l0 Polyoxyethylenet30)stearic acid 200 10.4 160 4 0.51 I2 I l Polyoxyethylene(5)ARMBEN BS 100 26 I55-I65 6% 0.33 1.2 12 Polyoxyethylene( l4lcocoamine I00 16.6 150 5% 1 L2 13 Polyoxyethylenet20)sorbitan monolaurate I00 33 I50 7 1 L2 14 Polyoxyethylenet 20lsorbitan monostearate 100 27.6 [50 5 0.95 l.2 l5 Dioleate of polyoxyethylene(20)sorbitol I00 I5 I50 7 9.8 1.2 I6 Polyoxyethylene( 5 )octadecylamine 100 24 l50l 12 0.6 12 I7 Polyoxyethylene(20)ARMEEN TD 100 19.8 155 a 0.6 1.2 18 Polyoxyethylene(25)hydrogenated castor oil 100 8.4 155 6 0.5 1.2 19 Polyoxyethylenet 54)castor oil 100 6.6 I55 7% 0.9 L2 20 Polyoxyethyleneflfl )castor oil [00 4.5 150-165 10 0.6 1.2 21 Polyoxyethylene( l50)hydrogenated castor oil I00 32 I55 6% 0.75 1.2 22 Polyoxyethylene( S0 )octadecylamine I 00 6 I 50 12 0.77 I .2 23 Dioleate ol' polyoxyethylene(3 lsorbitol 100 24 l-l 6% 0.8 1.2 24 Polyoxyethylcne(25 )hydrogenated castor oil 5.6 155 7 0.53 1.7 25 Polyoxyethylene(25)hydrogenated castor oil I00 10. 1 I55 7 1 L5 26 PolyoxyethylenetZS )hydrogenatcd castor oil 600 100.1 155 6% l 27 Polyoxyethylene(25)hydrogenated castor oil 600 332 I55 7 1,6

"'Numbcr of carbamate groups introduced per hydroxy group in ethylene oxide adduct charged lhy analysis for nnmurea nitrogen]. Number of N-methylol groups per carbamatc group.

The procedure of Examples 1 to 27 is followed in Ex- 45 EXAMPLE 34 amples 28 to 3l except that the indicated amount of ethyl carbamate is used instead of urea and a toluene azetrope is used to remove the liberated ethanol. 100 grams of the indlcated ethylene oxide adduct are em- Curbamme of EXampe 8 35% ployed m each example. 50 Dimethylol-S-hydroxy propylene urea 65% Grams of Example Ethyl- Temperature Time- Carbamate" methylol Number Ethylene Oxide Adduct Carbamate C. Hours Hydroxy Carbamate 28 Polyoxyethylene( 5 )octadecylamine 44.5 140 9% 0.8 L2 29 Polyoxyethylene(25)hydrogenated castor oil 13.3 I30 6 0.9 L2 30 Polyoxyethylene(20lsorbitan monolaurate 48.5 I056 I L2 31 Polyoxyethylene(S)octadecylamlne 44.5 12% 0.8 1.2

"Number of carhamntc groupm introduced per hydroxy group in ethylene oxide adduct charged. Number of N-methylol groups per carbamate group.

The following are illustrative examples of the textile EXAMPLE 35 treating compositions of this invention. All percentages 65 are by we ght. lt s understood, of course, that addi- Melhylolmed carhumule 9f Example 2 60% tional textile treating compositions may be prepared by Dimethylol-5.5-dimethyl propylene urea 40% EXAMPLE 36 Methylolated carbamate of Example l 4% Dimethylol methoxy ethyl carbamate 96% EXAMPLE 37 Methylolated carbamate of Example 26 20% Methylolated carbamate of Example 9 20% Dimethylol dihydroxy ethylene urea 60% EXAMPLE 38 Methylolated carbamate of Example 16 42% Disodium tris (B-sulphatoethyl) sulfonium inner salt 38% Dimethylol hexahydropyrimidinone-Z 20% In accordance with the present invention, the above described textile treating compositions containing a durable press agent and a methylolated carbamate may be used to treat textile materials to impart thereto improved physical characteristics such as durable press, wrinkle resistance, tear strength, hand, and abrasion resistance. It has been found that if the textile treating compositions of this invention are applied to textile material along with a textile resin catalyst and the treated textile material heated to an elevated temperature, the durable press agent and the methylolated carbamate will be attached to the textile material so that the improved properties imparted to the textile material will not be removed by subsequent washing or drycleaning.

The textile resin catalyst may be any of the acid or latent acid catalysts which are conventionally used in the art to facilitate reaction of durable press agents with textile material. By latent acid catalysts is meant substances which develop acidity during the curing step. Particularly suitable catalyst include metal salts of 4 strong acids such as magnesium chloride, magnesium sulfate, and zinc nitrate; ammonium salts such as ammonium chloride and ammonium dihydrogen phosphate; amine salts such as triethylamine hydrochloride, and triethanolamine hydrochloride. The amount of Curing catalyst used will depend on the nature of the durable agent, the particular carbamate used, and on the curing temperature and curing time. In general, satisfactory results may be obtained by using from about percent to about 40 percent, preferably from about l0 percent to about 25 percent by weight of the catalyst based on the total weight of durable press agent and methylolated carbamate.

The textile treating compositions of this invention may be applied to textile materials from an aqueous medium. The pad bath may contain a surfactant or emulsifier. Illustrative examples of surfactants which may be used include polyoxyethylene( IZJtridecyl alcohol, polyoxyethylene(9)octylphenol, and polyoxye- IhyIene(9.2)nonyl phenol.

The textile materials may be treated with the bath containing the textile treating compositions of this invention by immersion therein or by spraying. In the immersion method of application, the textile material may either be run through a padding machine wherein the textile material is first dipped into the bath and then squeezed, or the textile materials may be dipped into the bath and the excess liquid extracted by centrifugation. In the spraying method of application, the textile materials are simply sprayed with the bath and then dried by any suitable means. The carbamate and durable press agent may be applied simultaneously or from separate baths. The catalyst for the durable press agent may be applied with the durable press agent and/or carbamate or from a separate bath.

The amount ofa textile treating compositions of this invention which is applied to the textile material may vary from about 1 percent to about percent, preferably from about 4% to about 10%, by weight based on the dry weight of the textile material.

It is necessary to subject the textile material having a textile treating composition of this invention thereon to an elevated temperature in order to initiate a curing reaction between the said composition and the textile material. The particular temperature used and the duration of the heating step depends on the nature of the textile material used and on the the particular methylolated carbamate and durable-press resin used. In each situation, however, the temperature and heating time is that necessary to sufficiently cause reaction of the methylolated carbamate anddurable-press resin with the textile material. Generally, the heat cure may be effective at temperatures from about 100F. to about 350F. and in periods of time ranging from about to minutes at the lower temperature to about 2 to 3 minutes at the higher temperature. The preferred temperature is from about 300350F.

Textile materials which may be treated with the textile compositions of this invention include any textile material containing active hydrogen atoms; for exam ple, textile material comprising cellulose or modified cellulose such as cotton, rayon, linen, and mixtures thereof; textile material containing noncellulosics such as nylon, acrylics, polyesters, and mixtures thereof; and textile materials comprising a blend of cellulosic materials and non-cellulosic materials. The textile materials may be in the form of filaments, fibers, threads and yarns or in the form of woven, nonwoven, knit, or otherwise formed fabrics, sheets, and cloths. The preferred textile material is woven cotten fabric and cotton/- polyester blends.

The following examples are illustrative of the application of textile treating compositions of this invention to textile materials. The physical properties of the treated textile materials are determined according to the following test procedures.

Monsanto crease angle recovery ASTM D1295- GOT Elmendorf tear strength ASTM Dl424-59 Stoll'FIex abrasion resistance ASTM Dll75-61T In examples 39 to 52, scoured swatches of Testfabrics Style No. 4l3 bleached, mercerized cotton twill are padded at 70 percent wet pickup on the Butterworth Pad with an aqueous bath containing 3.6 percent of the indicated carbamate, 5.4 percent of dimethylol dihydroxy ethylene urea durablepress agent, l.2 percent of zinc nitrate catalyst, and 0.25% of polyoxyethylene (9.2) nonyl phenol wetting agent. The bath is prepared by mixing the carbamate with the durablepress agent, adding the wetting agent, diluting with warm water, and adding an aqueous solution of the catalyst. The padded fabrics are dried 5 minutes at 225F.,

cured at 325F. for 10 minutes, and conditioned at 70F. and percent R. H. for sixteen hours. Half of the swatches from each treatment are washed ten times in an automatic washing machine with TIDE and hot water. The properties of the treated fabrics are shown in Table l.

EXAMPLE 59 Scoured swatches of Testfahrics Style No. 407 cotton fabric are padded at 73% wet pickup in the Butter- 5 TABLE I Carba Example mate of Monsanto Crease Angle Elmendorf Warpwise Stoll-Flex Abrasion Number Example Recovery W+F (Degrees) Tear Strength (1h.) Resistance (W-I'F) (cycles) Wash 10 Washes 0 Wash Ill Washes 0 Wash 10 Washes 39 3 282 264 2.6 2.4 1423 I385 40 l 247 232 2.4 1.8 1744 III] 4| 4 243 249 2.1 1.5 1956 1231 42 257 246 2.3 1.6 1262 1446 43 e 261] 242 2.0 1.8 1162 1239 44 7 271 247 2.2 1.7 1393 929 45 8 258 239 2.3 1.6 906 11145 46 9 267 239 2.2 1.4 1152 912 47 260 239 2.2 1.3 1097 1983 48 II 228 232 2.8 3.2 1636 1813 49 12 238 236 2.0 2.2 1244 1579 50 30 240 252 L7 L6 1035 1148 51 13 256 257 2.1 1.8 1039 891 52 14 268 245 2.5 2.2 1473 1409 In Examples 53 to 56, swatches of cotton poplin fahworth Pad with an aqueous bath containing 1% of the ric are padded at 70% wet pickup on the Butterworth methylolated carbamate of Example 24, 9 percent of Pad with an aqueous bath containing 4.95% dimethylol dimethylol dihydroxy ethylene urea, 1.4 percent of zinc dihydroxy ethylene urea, 4% of the indicated carhamnitrate, and 0.25 percent of polyoxyethylene (9.2) ate, 1.4% of zinc nitrate, and 0.25% of polyoxylethynonyl phenol. The padded fabrics are dried for five lenc (9.2) nonyl phenol. The treated fabrics are dried minutes at 210F. and cured for ten minutes at 325F. for 5 minutes at 210F., cured at 325F. for 10 minutes, The treated fabric has a Monsanto Crease Angle Reand conditioned at 70F. and 65% R. H. for twelve covery in the warp plus fill directions of 298 prior to hours. The properties of the treated fabrics, prior to washing and 274 after ten washings, a Stoll-Flex abra- Washlng and after 10 washings are shown n Ta l 11. sion resistance in the warp plus fill directions of 689 cy- TABLE 11 Carba Example mate of Monsanto Crease Angle Elmendorf Warpwise Stoll-Flex Abrasion Number Example Recovery W+F (Degrees) Tear Strength (1b.) Resistance (W+F) (cycles) 0 Wash 10 Washes 0 Wash 10 Washes 0 Wash 10 Washes In Examples 57 and 58, scoured swatches of Testfabrics Style No. 7402M fabric comprising a blend of 65 percent DACRON S4 polyester and 35% cotton poplin are padded at 57 percent wet pickup on the Butterworth Pad with an aqueous bath containing 6.2 percent dimethylol dihydroxy ethylene urea, 5.1 percent of the indicated carbamate, 1.7 percent of zinc nitrate, and 0.25% of polyoxyethylene (9.2) nonyl phenol. The padded fabric swatches are dried at 200F. for three minutes, cured at 325F. for 10 minutes. and condi tioned at 70F. and 65 percent R. H. for twelve hours. The physical characteristics of the swatches, prior to washing and after ten washings in hot TIDE solution, are shown in Table III.

cles prior to washing and 584 cycles after ten washings, and an Elmendorf tear strength in the warp direction of 1.27 pounds prior to washing and 1.34 pounds after ten washings. The treated fabric has a subjective hand rating of 2.2 prior to washing and 2.2 after ten washings. The subjective hand rating is a measure of softness, and the numerical rating increases as the softness decreases. Cotton fabric treated in accordance with the above described process, except that the pad bath does not contain the mcthylolated carbamate, shows a subjective hand rating of 3.8 prior to washing and 3.2 after ten washings.

It will be understood that the compositions of the present invention as described herein and defined in TABLE 111 Carba- StollFlex Abrasion Example mate of Monsanto Crease Angle Elmendorf Warpwise Resistance Warp Only Number Example Recovery W-l-F (Degrees) Tear Strength (1b.) (cycles) 0 Wash 10 Washes 0 Wash 10 Washes l0 Washes the claims include those compositions containing the named ingredients and any other ingredients which do not destroy the effectiveness of the compositions for the purpose stated in the specification and, although this invention has been described with reference to specific reactant materials, including specific methylolated carbamates, ethylene oxide adducts, methylolating agents, and catalysts. it will be apparent that still other different and equivalent materials may be substituted for those described. Moreover, application processes and reaction steps thereof may be modified. reversed, or even in some cases eliminated, all within the spirit and scope of this invention.

Having described the invention. what is desired to be secured by Letters Patent is:

l. A textile treating composition comprising a durable press agent and an N methylol or N.N-dimethyll carbamate of an ethylene oxide adduct selected from the group consisting of( l an ethylene oxide adduct of a fatty acid containing from l2 to 28 carbon atoms, (2) an ethylene oxide adduct of a secondary fatty amine containing from 12 to 28 carbon atoms, (3) an ethylene oxide adduct of an ester of a fatty acid having from 12 to 8 carbon atoms and a polyol having from 2 to 6 hydroxyl groups and from 3 to 6 carbon atoms, and (4) a partial ester of a fatty acid having from 12 to 28 carbon atoms and an oxyethylene adduct of a polyol having from 2 to 6 hydroxyl groups and from 3 to 6 carbon atoms.

2. A textile treating composition of claim 1 wherein the carbamate is a carbamate of an ethylene oxide adduct of a fatty acid containing from 12 to 28 carbon atoms.

3. A textile treating composition of claim 1 wherein the carbamate is a carbamate of an ethylene oxide adduct of a secondary fatty amine containing from 12 to 28 carbon atoms.

4. A textile treating composition of claim 1 wherein the carbamate is a carbamate of an ethylene oxide adduct of an ester of a fatty acid having from l2 to 28 carbon atoms and a polyol having from 2 to 6 hydroxyl groups and from 3 to 6 carbon atoms.

5. A textile treating composition of claim 4 wherein the ester is castor oil.

6. A textile treating composition of claim 4 wherein the ester is hydrogenated castor oil.

7. A testile treating composition of claim 4 wherein the ethylene oxide adduct is polyoxyethylene (2S) hydrogenated castor oil.

8. A textile treating composition of claim 1 wherein 14 the carbamate is a carbamate ofa partial ester of a fatty acid having from 12 to 28 carbon atoms and an oxyethylene adduct of a polyol having from 2 to 6 hydroxyl groups and from 3 to 6 carbon atoms.

9. A textile treating composition of claim 8 wherein the fatty acid is oleic acid and the polyol is sorbitol.

10. A textile treating composition comprising dimethylol dihydroxy ethylene urea and an N-methylol or N,N-dimethylol carbamate of an ethylene oxide adduct selected from the group consisting of 1. an ethylene oxide adduct ofa fatty acid containing from l2 to 28 carbon atoms,

2. an ethylene oxide adduct of a fatty alcohol containing from l2 to 28 carbon atoms,

3. an ethylene oxide adduct ofa fatty amine containing from l2 to 28 carbon atoms,

4. an ethylene oxide adduct of an ester of a fatty acid containing from l2 to 28 carbon atoms and a polyhydric alcohol containing from 3 to 6 carbon atoms and from 2 to 6 hydroxyl groups, and

5. a partial ester of a fatty acid containing from 12 to 28 carbon atoms and an adduct of ethylene oxide and a polyhydric alcohol containing from 3 to 6 carbon atoms and from 2 to 6 hydroxyl groups.

11. A textile treating composition of claim 10 wherein the carbamate is a carbamate of an ethylene oxide adduct of a fatty alcohol containing from l2 to 28 carbon atoms.

12. A textile treating composition of claim 10 wherein the carbamate is a carbamate of an ethylene oxide adduct of a fatty amine containing from 12 to 28 carbon atoms.

13. A process of treating textile material containing cotton which comprises applying to the textile material, a textile treating composition of claim 1 and an acidic curing catalyst and thereafter curing by heating the textile material to an elevated temperature.

14. A process of treating textile material containing coton which comprises applying to the textile material, a textile treating composition of claim 10 and an acidic textile resin curing catalyst and thereafter curing by heating the textile material to an elevated temperature.

15. An article of manufacture which comprises a textile material treated in accordance with the process of claim l3.

16. An article of manufacture which comprises a textile material treated in accordance with the process of claim 14.

I I l l' UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,897,208 DATED July 29 1975 INVENTOR(S) Barry M. Shay It is certified that error appears in the above-identrfied patent and that said Letters Patent are hereby corrected as shown below:

Column 7,

IColumn I Column r Column 13,

line 30, exmaples" should read examples line 61, ARMEED" should read ARMEEN line 48, "Ch OH" should read CH OH Example ll, "ARMBEN" should read ARMEEN Example 15, "9.8" should read 0.8

lines 18 & 54,"Carbamate (1) "should read-Carbamate Hydroxy Hydroxy lines 18 & 54,"Methylol "should read-Methylol Carbamate Carbamate line 24, "to 8 carbon" should read to 28 carbon Signed and Scaled this Tlu'rreenrb Day Of September 1977 [SEAL] A nest:

RUTH C. MASON Arresting Oflicer LUTRELLE F. PARKER Acting Commissioner of Patents and Trademarks

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US1959930 *May 13, 1931May 22, 1934Ig Farbenindustrie AgHydroxy-alkyl ethers of polyhydric alcohols and their production
US1970578 *Nov 24, 1931Aug 21, 1934Ig Farbenindustrie AgAssistants for the textile and related industries
US2002613 *Feb 23, 1933May 28, 1935Gen Aniline Works IncReaction product of an organic acid amide and an alkylene oxide
US2157362 *Nov 3, 1936May 9, 1939Ig Farbenindustrie AgProcess of producing urethane substances containing carboxyl or sulphonic acid groups
US2184008 *Nov 26, 1937Dec 19, 1939Eastman Kodak CoConditioning of yarns to adapt them for textile operations
US2197479 *Jan 4, 1936Apr 16, 1940Du PontCarbamic acid esters of monoalkyl ethers of polyalkylene glycols
US2218939 *Jun 3, 1937Oct 22, 1940Gen Aniline & Film CorpUrethane-like compounds
US2477346 *Jun 28, 1946Jul 26, 1949Du PontMethylol-behenamide and related compounds
US2518267 *Oct 5, 1948Aug 8, 1950Ici LtdQuaternary compounds and manufacture and use thereof as textile treating agents
US2585826 *Nov 5, 1948Feb 12, 1952Gen Aniline & Film CorpCarbamate-quaternary ammonium compounds and their preparation
US2998445 *Jun 22, 1959Aug 29, 1961California Research CorpPolyglycol carbamates
US3427332 *Sep 5, 1967Feb 11, 1969Pennsalt Chemicals CorpPerfluoroalkyl amide derivatives of polyoxyalkylene carbamates
US3524876 *Jul 27, 1965Aug 18, 1970Dan River Mills IncN,n-dimethylolcarbamates of ether alcohols
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4245110 *Mar 10, 1975Jan 13, 1981Bayer AktiengesellschaftPolyalkylene oxide-containing urethane polyols with sulphonic acid groups
US4353707 *Sep 15, 1981Oct 12, 1982The United States Of America As Represented By The Secretary Of AgricultureTextile finishing agents from reaction products of carbamates and glutaraldehyde
US6872424Mar 6, 2002Mar 29, 2005Nano-Tex, LlcDurable finishes for textiles
US20020160675 *Mar 6, 2002Oct 31, 2002Nano-Tex, LlcDurable finishes for textiles
Classifications
U.S. Classification8/187, 8/115.7, 8/DIG.210, 8/DIG.400, 8/115.6, 560/166, 554/110
International ClassificationC08G65/28, D06M13/425
Cooperative ClassificationD06M13/425, Y10S8/04, Y10S8/21
European ClassificationD06M13/425