Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.


  1. Advanced Patent Search
Publication numberUS2787516 A
Publication typeGrant
Publication dateApr 2, 1957
Filing dateOct 23, 1953
Priority dateOct 23, 1953
Publication numberUS 2787516 A, US 2787516A, US-A-2787516, US2787516 A, US2787516A
InventorsCompton Jack, Barber Richard Paul
Original AssigneeInst Textile Tech
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Process for the treatment of cyanoethylated cotton textiles with amines
US 2787516 A
Abstract  available in
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)


Va., assignors to Institute of Textile Technology, Albemarie, Va., a corporation of Virginia No Drawing. Application october 2s, 1953, serial No. 338,053

This invention relates to cotton products in the form of yarn or fabrics, and has for its object the provision of an improved process of increasing the tensile strength, elongation and abrasion .resistance of such products. More particularly, the invention provides an improved process comprising the treatment of thecotton products with a Water-soluble amine in liquidphase, advantageously in aqueous solution, toefect a surprising increase in the tensile strength, elongation, and abrasion resistance. The cotton product may be under tension or zero tension during the treatment. By cotton products, we mean yarn, thread, cord, or fabrics formed of natural cotton or of partially cyanoethylated cotton.

The treatment of the cotton products under zero tension is also disclosed in our copending application Serial No. 388,054, filed October 23, 1953.

One of the important aspects of our invention is that we can treat thelcotton product with a liquid amine at normal pressures and temperatures, or with a water solution of an amine in lany suitable concentration, while under tension'or zero tens-ion, in a simple and practical operation in apparatus of the type commonly used to treat yarns and fabrics with liquids. The cotton product is treated with Ia water-soluble liquid `amine having the general structure for uselinA practicing the invention may be represented by the formula in which n is an integer from 1 to 6. n

The` partially icraathylate 90u91; Pradet?, .treated according to thev invention can be formed in any suitable Way to aproduct containing fromv 0.1 to around 2.5 Acyanoethyl cellulose units 'per anhydro-glucose unit. Cellulose which has been treated with an aqueous solution of alkali, su ch as sodium hydroxide, reacts with acrylonitrile to 1form the cyanoethyl cellulose ether. The degree of substitution depends` upon the concentration of the alkali solution, the period, and thel temperature of th treatment a@ ssnentratis'njef the .arylntfile BY controlling 'these variables aco'tton product 'can be'frmed containing an effective amount of cyanoethyl cellulose.

flid States Perm 2 It. is .an Object of 'the invention t0 combine only Such an amount of acrylonitrile with the cotton as will impart the improved propertiesdesired in the wayrof increased tensile strength, and also resistance to mold-causing microorganisms.

In accordance withrour invention, We may treat the cotton in any suitable way with acrylonitrile to eiect but a partial conversion to cyanoethyl cellulose, the major portion of the cotton preferably remaining in thel form of cellulose. We aim to avoid such an amount of sub- -stitution that the cotton fibers lose their fibrous character and to this end prefer not to combine more kthan 2 to 2.5 cyanoethyl celluloseunits per anhydro-glucose unit. We have found it advantageous and very practical to jimrnerse the cotton in a sodium hydroxide solution varying,

say, from 0.10% to 10%` of sodium hydroxide, preferably around 0.25% to 2.5% for around twenty minutes, and then to squeeze out the excess caustic solution to about a increase in weight. The cotton is then contacted with acrylonitrile, either as a vapor or as `an aqueous solution until the required amount of conversion has been effected. This can beldone by refluxing with acrylonitrile at 76 C. for about two minutes and` then washing with water. In such an operation, the nitrogen content varies from 1.6% to 1.8%. The amount of conversion may also be expressed in terms of percent nitro gen and to this end we prefer to use cotton containing from 0.5% to 4.8% N. The following table gives the cyanoethylation expressed in percent N and cyanoethyl cellulose per glucose unit onnative cotton:

In using our preferred range of cyanoethylation, We not only produce a cotton product which is particul-arly amenable to the process of this invention but aproduct which is especially resistant to heat and the attack of such micro-organisms as the spores of Chetomtmt globosum which cause mildew, las more fully described and claimed in the copending application of l ack Compton and Catesby P. Jones, Serial No. 201,063, filed December 1 5, 1950, now abandoned.

Any suitable kindl of tensioning apparatus may be used. such as that used for stretching yarns or fabrics while immersed in liquid. A practical apparatus for laboratory purposes may consist of a beam balance arranged so that the weights neededfor the desired tension can be attached kto one arm while the skein to be treated is hung Aon the other arm. While we may use varying amounts of Vtension or zero tension while applying the amine inliqiid phase as in aqueous solution, we prefer to use an Kappreciable tension, preferably just below .that which would injure the yarn or fabric. v l

While the invention is not predicated on any theory asv tothe improved properties imparted to the product,

0 `itrnay be explained asfbeingdue to the swellingaction crease in inter-ber friction, and a more perfect orientation of the brile and other organized elements of the fiber structure.

Particular types of amines which have been used very effectively in the process of our invention include -the following: the alkyl mono, di, tertiary, 3-substituted propyl, and polyalkylenepoly-amines. VSpecific amines include: methylamine, ethylamine, dimethylamine, trimethylamine, triethylamine, triethanolamine, ethylenediamine, diethylenetriamine,l 3-isoproxypropylamine, 3- methoxypropylamine, 3,3'-iminobispropylamine, 3-dimethylaminepropylarnine, 3-isopropylaminopropylamine. In determining the tensile strength on yarns, single end breaking tests were carried out on all samples. The procedure employed involved treating two 17 yard skeins under the same condi-tions, testing l ends from each skein, the average of which (20 single ends) gave the breaking strength of the yarns treated. The percent increase in strength was based on the difference in the number lof grams tension required to break the treated yarns in comparison with the original breaking strength of the yarns before the treatment. In some cases the breaking strength is expressed as grams/grex.

In treating the cotton products with an amine, the product is preferably immersed in the liquid amine to effect complete penetration and while wet with the amine the product may be subjected to tension. Thereafter, the product is rinsed in water and dried.

The amine treatment used in the following tests was carried out as follows: (a) the yarn skein was placed on the tensioning apparatus and tension applied, (b) a container was filled with the amine solution and by means of a crank the skeins were passed continuously through the annue solution and (c) after the required time in the amine solution, the amine was removed from container by means of suction, water wats added and the skeins washed several times to remove the amine. After several washings, the skeins were placed in running water for neutralization.

Two skeins were treated under the same conditions. The physical testing on the yarn was carried out on an IP-Z Incline Tester. Ten single ends were tested from each skein. The average of the data obtained on the two skeins gave the breaking strength of the yarns. The two skein procedure was used to minimize experimental errors.

In a series of tests carried out using several primary alkylamines, the yarns were impregnated with the primary alkylamines under normal conditions of pressure and temperature. (Hereinafter, for convenience, acry lonitrile will sometimes be referred .to simply as AN.) The results of these experiments are shown in Table I.

TABLE I Effect of the treatment of native and partially cyano-4 4 TABLE II 4 Eects of various skein tensions on the .single end breaking strength of cyanoethylated 80/2 cotton yarns containing 1.8% nitrogen treated with alkylamines for 10 minutes Single End Breaking Strength, Gms.

Tension, gms.

Trlethan- Ethyl- Dimethylolamine amino amine Original breaking strength ol cyanoethylated yarns=358 gms.

The effect of varying the skein :tension during the treatment with trimethylamine on the single end breaking strength of the yarns is shown in Table III.

TABLE III The eects of various skein tensions on the single end breaking strength` of native and cyanoethylated 40/2 cotton yarns, containing 1.6% nitrogen treated for 10 minutes at room temperature with trimethylamine Single End Breaking Strength, Grams Tension, gms.

Native yarns AN yarns 628 719 608 671 582 053 588 070 614 076 m4 676 616 686 Skein broke-.- 707 Original breaking strength of native yarns=595 grams. Original breaking strength of AN yarns=547 grams.

TABLE IV The effects of skein immersion time on the single end ethylated 80/2 cotton yarns containing 1.8% nitrogen, 55 breaking? strength Cyal0ehylated,40/2 Cotto" yafns nnder 2000 grams skein tension for l0 minutes at room contamin 16% mirage reared with mmethylamm?, I temperature with various alkylamines on the single end Undef Zero tension breaking strength Ti Min Silslgle llreaktugI me TCD [ams- Single End Breaking 6o Cyanoethylated Strength, Gms. (AN) Yarns Animes Concentra tion Native AN 5 712 Treated 10 709 15 694 20 v6 Triethanelaminc 373 388 an Ethylamine. 416 422 an 666 Triethylamlne 422 449 Choline 451 Dimethylamme..-

384 402 original breaking strength of` cyanoethylated yarn8=547 Original breaking strength oi native yarns=341 gms. Original breaking strength oi An yarns=366 gms.


The 3-substituted propylamines are especially effective amines for the purpose of the invention. The effects of 3-propylamines on the breaking strength of partially cyanoethylated yarns are shown in Tablel V, and particularly by a significant increase in breaking strength.

5 TABLE v The effect of skein treatment of 40/2 native and partially cyanoethylated cotton yarns containing 1.6% nitrogen with various S-snbstitnted propylamines under zero tension for 10 minutes on the breaking strength and elongation Original breaking strength of native yarns=595 gms.; elongation=5.0%. Original breaking strength of AN yarns=545 gms.; elongat1on=5.10%.

TABLE VI The eect of skein treatment of 40/2 native and partially cyanoethylated cotton yarns containing 1.6% nitrogen with 3-isopropoxypropylamine under various tensions for 5-minates on the breaking strength and elongation Single End Breaking Elongation, Strength, gms. Percent Tension, gms.

Native AN Native AN Original breaking strength of native yams=595 gms.; elongation= 5.0%.

Original breaking strength of .AN yarns=545 gms.; elongation=5.10%.

In these tests the designated tensions were applied to the yarns in the presence of the amine for minutes after which the elongation was held constant for 5 additional minutes. At zero tension the time of treatment was minutes. it will be noted that the increase in strength of both native and AN yarns resulting from treatment with 3-isopropoxypropylarnine under tension is less than when no tension was employed. However, the elongation of the yarn in the case of the AN yarn was materially decreased while considerable increases in strength over the control was eiected. AN yarns thus lend themselves to engineering for specic end uses more readily than native yarns.

These .3l-substituted propylamines not only are very eiective when used alone but they are very effective when used with other amines. The 3substituted propylamines possess comparatively high swelling power for cellulose and are good solvents for tats and waxes found on the surface of the cotton fibers. It can be seen that the cyanoethylated yarns treated with the 3substituted propyl- 55 amines result in a greater increase in tensile strength than the increase in strength imparted to native cotton given the same treatment.

Many of the amines as described herein are available in liquid form as commercial products, i. e., they are liquid at normal room temperatures. However, such liquid amines may also be dissolved in water. Other amines are preferably dissolved in water. While the amount of Water is not critical, we prefer to use less than 50% by volume of water.

We claim:

1. The process for the treatment of a cyanoethylated cotton textile product containing from 0.1 to 2.5 cyanocthyl cellulose units per anhydroglucose unit which cornprises impregnating said product with an amine of the group consisting of methylamine, ethylamine, dimethylamine, trimethylamine, triethylamine, triethanolaminc, ethylenediarnine, diethylenetriamine, choline, 11i-isopropoxypropylamine, S-methoxypropylamine, 3,3iminobis propylamine, 3dirncthylaminepropylamine and 3-isopropylaminopropylamine, said amine being in liquid phase containing less than 50% by Volume of water, said product being impregnated with the amine at normal room temperatures and pressures and maintained in contact with the amine for at least tive minutes and until the tensile strength and elongation has been materially increased, washing and drying the product.

2. The process of claim 1 wherein the cyanoetliylated cotton textile product, while being impregnated with the amine, is under tension.

3. The process of claim l wherein the amine is a 3- substituted propylamine.

4. The process according to claim 1 wherein the amine is 3-isopropoxypropylamine.

5. The process of claim 1 wherein the amine is 3- methoxypropylamine.

6. The process of claim 1 wherein the amine is 3,3- iminooispropylamine.

7. The process of claim 1 wherein the amine is 3- dimethylaminopropylarnine.

8. The process of claim 1 wherein the amine is 3-is0- propylarninopropylamine.

9. The process of claim 1 wherein the cyanoethylated cotton textile product is impregnated with an amine in aqueous solution.

References Cited in the tile of this patent UNITED STATES PATENTS 1,986,881 Dreyfus lan. 8, 1935 2,050,196 Sebrell Aug. 4, 1936 2,189,918 Moncrief Feb. 13, 1940 2,580,491 Ward lan. 1, 1952 FOREIGN PATENTS 279,801 Great Britain Dec. 13, 1928 479,341 Great Britain Feb. 3, 1938 OTHER REFERENCES British Rayon and Silk Journal, May 1950, pp. 62, 63 and 88.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US1986881 *Nov 18, 1930Jan 8, 1935Henry DreyfusNew cellulose derivatives and their manufacture
US2050196 *Mar 1, 1932Aug 4, 1936Wingfoot CorpPrevention of deterioration of cotton cord by heat
US2189918 *May 5, 1937Feb 13, 1940Celanese CorpTreatment of materials of natural or artificial origin
US2580491 *Aug 8, 1950Jan 1, 1952Conrad Carl MReducing the crystallinity of native fibrous cellulosic material
GB279801A * Title not available
GB479341A * Title not available
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3316178 *Nov 12, 1964Apr 25, 1967Allis Chalmers Mfg CoThermostable dielectric material
US3419498 *Jul 13, 1966Dec 31, 1968Westinghouse Electric CorpThermally stable cellulose products
US4855139 *Jan 20, 1987Aug 8, 1989Med. Fab (Lafayette), Inc.Phenolic fungicide chemically bonded to textile through bisoxirane compound
U.S. Classification8/129, 536/30, 8/196, 8/120, 536/43, 8/DIG.130
International ClassificationD06M13/345, D06M13/368, D06M13/332, D06M13/325
Cooperative ClassificationD06M13/368, D06M13/325, Y10S8/13, D06M13/332, D06M13/345
European ClassificationD06M13/368, D06M13/325, D06M13/332, D06M13/345