US2469407A - Treatment of textile materials - Google Patents

Treatment of textile materials Download PDF

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Publication number
US2469407A
US2469407A US632284A US63228445A US2469407A US 2469407 A US2469407 A US 2469407A US 632284 A US632284 A US 632284A US 63228445 A US63228445 A US 63228445A US 2469407 A US2469407 A US 2469407A
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Prior art keywords
fabric
salt
maleic anhydride
polyamine
fabrics
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US632284A
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Donald H Powers
Elmer H Rossin
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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Priority to BE469563D priority Critical patent/BE469563A/xx
Application filed by Monsanto Chemicals Ltd filed Critical Monsanto Chemicals Ltd
Priority to US632284A priority patent/US2469407A/en
Priority to GB33120/46A priority patent/GB629097A/en
Priority to FR936219D priority patent/FR936219A/en
Application granted granted Critical
Publication of US2469407A publication Critical patent/US2469407A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/332—Di- or polyamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • D06M15/233—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated aromatic, e.g. styrene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
    • Y10T442/277—Coated or impregnated cellulosic fiber fabric
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2861—Coated or impregnated synthetic organic fiber fabric
    • Y10T442/2893—Coated or impregnated polyamide fiber fabric
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2926—Coated or impregnated inorganic fiber fabric
    • Y10T442/2992—Coated or impregnated glass fiber fabric
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/30—Woven fabric [i.e., woven strand or strip material]
    • Y10T442/3049—Including strand precoated with other than free metal or alloy

Description

Patented May 10, 1949 2,469,407 ICE 2,409,407 TREATMENT OF TEXTILE MATERIALS Donald H. Powers, Winchester, and Elmer H.
Rossin, Melrose, M
asa, assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application December 1, 1945, Serial No. 632,284
14 Claims. (Cl. 117-161) This invention relates to improved textile finishing materials, and methods of treating yarns and fabrics therewith.
It is common practice to treat yarns and fabrics with starch solutions in order to impart a relatively stiffened finish thereto. Starched fabrics however lose their stiffened character and appearance after a single washing, and also tend to dust out. In the case of yarns the starch is applied primarily as a size for assisting in the weaving operation, but here also the effect of the starch is markedly diminished by the unstable character of the coating.
It is a primary object of the present invention to provide a substantially permanent stiffened finish on fabrics which cannot be appreciably removed by ordinary washing operations and is substantially free of dusting. A further object of the invention is to provide a method of finishing fabrics which involves applying the finishing agent to the warp yarns prior to weaving, whereby the weaving operation is facilitated and a suitably finished fabric is obtained without further treatment.
In accomplishing the above objects the yarn or fabric is treated with an aqueous solution or dispersion of an ammonium or amine salt of copolymerized styrene maleic anhydride and a polyamine, after which the yarn or fabric is heated. This causes the styrene maleic anhydride copolymer to react with the polyamine, thereby insolubilizing the resin so that most of it remains on the fabric after washing and provides a substantially permanent finish. The polyamines which may be used for the purposes of this invention include ethylene diamine, diethylene triamine, tetraethylene pentaamine, and the like. Suitable ammonium or amine salts of the copolymer include the salts of ammonia, 'guanidine, alkylamines, such as methyl, butyl and amyl amine, and quaternary ammonium hydroxides, such as phenyl trimethyl ammonium hydroxide.
In treating the fabric in the mannerdescribed above, it is preferable to keep the solution or bath below 110 F. to avoid appreciable reaction taking place during the impregnation ofthe" fabric. However, the bath may be kept at somewhat higher temperatures for short periods without harmful effect. Upon removal from the bath, the fabric is heated at an elevated temperature until it is dry. Preferably, the fabric is heated at 250 to 300 F., but satisfactory results may be obtained at temperatures as low as 200 F. The concentration of the styrene maleic salt in the bath and the pick-up should be adjusted to 55 deposit on the fabric from 2 to 15% by weight of the styrene maleic salt, but preferably between about 4'and 7%. The polyamine is ordinarily added in amounts varying between and 30% on the weight of the styrene maleic salt,
Instead of using solutions containing both the anhydride salt and the polyamine, separate solutions of the two ingredients may be prepared, after which the yarn or fabric may be treated in any order or simultaneously therewith. It is desirable to have the bath or solution at slightly elevated temperatures to insure uniform penetration, but good results may also be obtained with the bath at room temperatures.
The copolymer of styrene and maleic anhydride used in accordance with this invention is a wellestablished product which may be prepared in several ways. One of the well-known methods is mass polymerization, which involves heating styrene and maleic anhydride at temperatures between about and 300 F. for several hours or more. Preferably, the materials are heated cautiously, as in a water bath. Another method which may be used is known as the solvent process which involves reacting the styrene and maleic anhydride at slightly elevated temperatures in the presence of a solvent which is capable of dissolving both the starting materials and the finished polymer, such as acetone. If desired, the copolymerization may be carried out in the presence of a catalyst, such as benzoyl peroxide.
The copolymer of styrene and maleic anhydride produced by either of the above or by any other well-known method of manufacture is soluble in acetone, but insoluble in alcohol or benzene, and forms water-soluble salts of ammonia or alkali metals. styrenes, such as methyl or butyl styrene, chlorstyrene or the like, may be used to prepare copolymers which are soluble in dilute aqueous solutions of alkali or ammonia. Instead of maleic anhydride, partially esterifled maleic anhydride, such as the half ester of isopropyl maleate may be used. It is also possible to prepare and use in accordance with this invention copolymers of styrene. and maleic anhydride which have have been copolymerized with relatively small amounts of other unsaturated compounds, such as vinyl acetate, vinyl chloride, vinyl ethyl ether, indene, vinyl methyl ketone, acrylic esters and the like.
A further understanding of the invention will be obtained from the following examples, the parts being given by weight:
Example I A solution of an ammonium salt of styrene maleic anhydride resin was prepared by mixing together 600 parts of styrene maleic anhydride, prepared by copolymerizing equimolecular quantitles of styrene and maleic anhydride at about 200 F. in a water bath, 400 parts of 26% NHiOH and 9000 parts of water. The resulting mixture was then heated to 200 to 212 F. with stirring, and maintained at this temperature until a uni- Instead of styrene, substituted form, somewhat viscous transparent solution resulted. This required about one hour. After cooling thesolution to about 100 F., ethylene diamine was added to the extent of about on the weight of the styrene maleic anhydride used.
Heavy cotton sheeting was dipped in the bath prepared as described above, after which it was passed through a padder adjusted for 100% pickup. The bath was maintained at about 100 1''. during the treatment of the fabric to insure uniform penetration. The treated sheeting was then heated for about two and a half minutes on a tenter frame using hot air at 300 F.. at which time it was substantially dry. The dry sheeting was washed for one hour at the boil in a running suds, and was found to retain 82% of the deposited resin.
Example II A solution of an ammonium salt of styrene maleic anhydride resin, containing 10% ethylene diamine was prepared as described in Example 1.
The resulting solution was then poured into the size box of a slasher, after which. a warp of 18/single cotton yarn was passed through the solution and dried on dry cans in the usual manner, using 12 pounds of steam. The treated yarn was then rolled up on a beam and woven. Excellent weaving was obtained and the resulting fabric possessed a desirably stiffened finish which retained its stiffened character even after washing. Moreover, the fabric had an unusually smooth feel and did not dust out.
Emmpie III Heavy cotton sheeting was dipped in the bath prepared as described above, after which it was passed through a padder adjusted for 100% pickup. The bath was maintained at about 100 F. during the treatment of the fabric to insure uniform penetration. The treated sheeting was then heated for about two and a half minutes on a tenter frame using hot air at 300 F., at the end of which time it was substantially dry. The dry sheeting was washed for one hour at the boil in a running suds, and was found to retain 85% of the deposited resin.
Example IV A solution of an ammonium salt of styrene maleic anhydride resin was prepared as described in Example I, and diluted with an equal amount of water. To this was then added diethylene triamine in an amount sufficient to provide about 10% on the weight of the styrene maleic anhydride used. Spun viscose rayon was dipped in the resulting bath, after which it was passed through a padder adjusted for 100% pickup. The bath was maintained at about 100 F. during the treatment of the fabric to insure uniform penetration. The treated rayon was then heated for about two and a half minutes on dry cans maintained at about 240 1"., at the end of which time it was substantially dry. The resulting fabric was smooth and full and somewhat stiffened, and retained these characteristics after several washings.
Example V I full and somewhat stiflened and retained these characteristics after washing.
Although the examples refer to the treatment of cotton, viscose rayon, acetate rayon, nylon and glass, equally good results, can be obtained with linen, flax, hemp, jute. ramie, wool, silk, cuprammonium rayon, various other synthetic textile materials, such as Vinyon and Aralac, and mixtures or blends of any of the above materials.
By treating fabrics with the finishing agents described herein, a substantially permanent, stiffened finish is obtained, due to the fact that only relatively small amounts of the dried and reacted resin are lost on washing, 1. e. of the order of 5 to 20%. The finished fabric is also smooth and substantially free of dusting in contrast to the well-known starch treated fabrics. 'When the resin is applied to the warp yarn and insolubilized thereon, there is the further advantage that the weaving operation is improved owing to the higher tensile strength of the yarn, its increased resistance to abrasion, and its generally stiffened character. The fabric prepared from treated yarn may have the desired finish characteristics without further treatment. but if desired it may be subjected to additional finishing operations.
It is customary to apply the sizing or finishing materials described herein to yarns or fabrics. However, it is possible to obtain similar results by treating fibers, either initially or at any stage of their processing prior to spinning, after which the fibers may be spun and woven to obtain fabrics of the desired finish characteristics. Yarns prepared from such treated fibers may also be readily woven. It is also possible'to treat in accordance with this invention fibers which are to be used as such, as for example in cotton batting, or in the preparation of non-woven fabrics.
It is believed that the reaction between the polymerized styrene maleic anhydride salt and the polyamine involves or consists of a cross linking between the polymer and the polyamine. It should be understood, however, that the invention is not predicated on this or any other similar theory, and regardless of the type of reaction which takes place the polymeric resin salt becomes insolubilized on the yarn or fabr'ic with the formation of a relatively'permanent size or finish. It should also be understood that the aqueous solutions referred to in the appended claims are intended to include aqueous dispersions, as it is possible that the ammonium or amine salts in the solution are actually present in the form of a colloidal dispersion.
What we claim is:
1. The method of finishing textile fabrics which comprises treating the fabric with an aqueous solution of alkylene polyamlne and a salt of copolymerized styrene maleic anhydride selected from the group consisting of ammonium salts and amine salts, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin on the fabric.
2. The method of finishing textile fabricswhich comprises treating the fabric with an aqueous solution of an amine salt of copolymerized styrene maleic anhydride and an alkylene polyamine, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin thereon.
3. The method of finishing textile fabrics which comprises treating the fabric with an aqueous solution of an ammonium salt of copolymerized styrene maleic anhydride and an alkylene polyamine, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin thereon.
4. The method of finishing textile fabrics which comprises treating the fabric with an aqueous solution of an ammonium salt of copolymerized styrene maleic anhydride and ethylene diamine, said diamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin thereon.
5. The method of finishing textile fabrics which comprises treating the fabric with an aqueous solution of an ammonium salt of copolymerized styrene maleic anhydride and diethylene triamine, said triamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin thereon.
6. The method of finishing textile fabrics which comprises treating the fabric with an aqueous solution of an ammonium salt of copolymerized styrene maleic anhydride and tetraethylene pentaamine, said pentaamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin thereon.
7. The method of finishing textile fabrics which comprises treating the fabric with an aqueous solution of an ammonium salt of copolymerized styrene maleic anhydride and an alkylene polyamine, said salt being deposited on the fabric in amounts varying from 2 to by weight, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fabric, whereby said treating agents react to form an insoluble resin thereon.
8. The method substantially as described in claim 7, but further characterized in that the fabric is impregnated with the solution at a temperature below 110 F. and is dried by heating for a short period of time at temperatures between 200 and 300 1".
9. The method of preparing and finishing textile fabrics which comprises treating warp yarn with an aqueous solution of an alkylene polyamine and a salt of polymerized styrene maleic anhydride selected from the group consisting of ammonium salts and amine salts, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, then drying the yarn, whereby said treating agents react to form an insoluble resin thereon, and weaving the resulting yarn into a fabric.
10. The method of sizing textile warp yarns which comprises treating said yarns with an aqueous solution of an alkylene polyamine and a salt of polymerized styrene maleic anhydride selected from the group consisting of ammonium salts and amine salts, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the yarn, whereby said treating agents react to form an insoluble resin thereon.
11. In the manufacture 'of textile yarns and fabrics from fibrous materials, the steps of treating said fibrous materials at some stage of their processing prior to spinning with an aqueous solution of an alkylene polyamine and a salt of copolymerized styrene maleic anhydride selected from the group consisting of ammonium salts and amine salts, said polyamine being added in amounts varying between 5 and 30% on the weight of said salt, and then drying the fibers thus treated, whereby said treating agents react to form an insoluble resin thereon.
12. The method of finishing textile materials, such as fibers, yarns and fabrics, which comprises treating said material with an aqueous solution of an alkylene polyamine and a salt of a copolymer prepared by copolymerizing a substance selected from the group consisting of styrene and substituted styrenes with a substance selected from the group consisting of maleic anhydride and partial esters of maleic anhydride, said polyamine being added inamounts varying between 5 and 30% on the weight of said salt, said salt being selected from the group consisting of ammonium salts and amine salts, and then drying the treated material, whereby said treating agents react to form an insoluble resin thereon.
13. A finishing composition for textile fibers.
I yarns or fabrics which comprises an aqueous solution consisting of an alkylene polyamine and a salt of polymerized styrene maleic anhydride in water, said salt being selected from the group consisting of ammonium salts and amine salts, said polyamine being present in amounts varying between 5 and 30% on the weight of said salt.
14. A textile fabric impregnated with a salt of polymerized styrene maleic anhydride selected from the group consisting of ammonium salts and amine salts, which salt has been cross linked with from 5 to 30% of an alkylene polyamine 0n the weight of said salt.
j DONALD H. POWERS.
ELMER H. ROSSIN.
REFERENCES CITED The following references are of record in the file of this patent:
UNI'I'ED s'm'rns PATENTS mm rub. 27, mt
US632284A 1945-12-01 1945-12-01 Treatment of textile materials Expired - Lifetime US2469407A (en)

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Application Number Priority Date Filing Date Title
BE469563D BE469563A (en) 1945-12-01
US632284A US2469407A (en) 1945-12-01 1945-12-01 Treatment of textile materials
GB33120/46A GB629097A (en) 1945-12-01 1946-11-07 Improvements in or relating to method of sizing or finishing textile materials, yarns and fabrics, and the finishing composition therefor
FR936219D FR936219A (en) 1945-12-01 1946-11-20 Improvements in sizing or finishing processes for textile materials or yarns; improved textile materials, fabrics, or yarns obtained by the foregoing processes and trimmings used with the improved process

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2576915A (en) * 1948-04-29 1951-12-04 Monsanto Chemicals Method of sizing yarns and composition therefor
US2616867A (en) * 1950-08-30 1952-11-04 Monsanto Chemicals Composition for and method of sizing yarns
US2650172A (en) * 1949-01-21 1953-08-25 American Viscose Corp Moistureproofing of nonfibrous cellulosic material
US2651587A (en) * 1947-06-02 1953-09-08 Monsanto Chemicals Treatment of textile materials
US2848357A (en) * 1954-12-15 1958-08-19 Monsanto Chemicals Aqueous terpolymer sized nylon yarns
US2953477A (en) * 1956-08-07 1960-09-20 Exeter Mfg Company Bias-cut woven glass fabric sized with a resinous material
US3062686A (en) * 1955-04-30 1962-11-06 Bayer Ag Process of treating textile with a copolymer and a cross-linking agent
US3111425A (en) * 1963-11-19 Coating regenerated cellulose
US3404979A (en) * 1963-11-13 1968-10-08 Lumiere Soc Electrophotographic layers with polyamide binders and a process for their manufacture
US3410720A (en) * 1965-07-12 1968-11-12 Monsanto Co Modified textile material resistant to penetration by aqueous media
US3981836A (en) * 1964-10-29 1976-09-21 Dan River Inc. Yarn sizes, sizing treatments and resulting sized yarns
US4189416A (en) * 1968-08-27 1980-02-19 Monsanto Company Composition containing an aqueous solution of a mixed salt of an interpolymer of styrene/maleic anhydride/vinyl acetate
US4248755A (en) * 1979-09-14 1981-02-03 Monsanto Company Composition and method for sizing textiles
US4508787A (en) * 1980-12-17 1985-04-02 The Standard Oil Company Imidized surface protection for maleic anhydride interpolymer articles
US5290849A (en) * 1992-11-06 1994-03-01 Monsanto Company Polymer solution for sizing paper
CN103243430A (en) * 2013-05-21 2013-08-14 海安县鑫荣纺织有限责任公司 Blended yarn of cotton fiber, ramie fiber and copper ammonia fiber

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1155437B (en) * 1982-12-22 1987-01-28 Montedison Spa FUNCTIONALIZED OLEFINIC POLYMER TEXTILE FIBERS AND PROCEDURE FOR THEIR PREPARATION

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US1976679A (en) * 1930-05-26 1934-10-09 Ig Farbenindustrie Ag Production of dispersions
US2047398A (en) * 1930-06-26 1936-07-14 Ig Farbenindustrie Ag Artificial resins and process of making them
US2275951A (en) * 1938-10-12 1942-03-10 British Rubber Prod Res Treatment of rubber
US2294651A (en) * 1936-10-26 1942-09-01 Hercules Powder Co Ltd High-gloss coated material
US2370362A (en) * 1943-01-01 1945-02-27 American Cyanamid Co Finishing of cloth

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1976679A (en) * 1930-05-26 1934-10-09 Ig Farbenindustrie Ag Production of dispersions
US2047398A (en) * 1930-06-26 1936-07-14 Ig Farbenindustrie Ag Artificial resins and process of making them
US2294651A (en) * 1936-10-26 1942-09-01 Hercules Powder Co Ltd High-gloss coated material
US2275951A (en) * 1938-10-12 1942-03-10 British Rubber Prod Res Treatment of rubber
US2370362A (en) * 1943-01-01 1945-02-27 American Cyanamid Co Finishing of cloth

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3111425A (en) * 1963-11-19 Coating regenerated cellulose
US2651587A (en) * 1947-06-02 1953-09-08 Monsanto Chemicals Treatment of textile materials
US2576915A (en) * 1948-04-29 1951-12-04 Monsanto Chemicals Method of sizing yarns and composition therefor
US2650172A (en) * 1949-01-21 1953-08-25 American Viscose Corp Moistureproofing of nonfibrous cellulosic material
US2616867A (en) * 1950-08-30 1952-11-04 Monsanto Chemicals Composition for and method of sizing yarns
US2848357A (en) * 1954-12-15 1958-08-19 Monsanto Chemicals Aqueous terpolymer sized nylon yarns
US3062686A (en) * 1955-04-30 1962-11-06 Bayer Ag Process of treating textile with a copolymer and a cross-linking agent
US2953477A (en) * 1956-08-07 1960-09-20 Exeter Mfg Company Bias-cut woven glass fabric sized with a resinous material
US3404979A (en) * 1963-11-13 1968-10-08 Lumiere Soc Electrophotographic layers with polyamide binders and a process for their manufacture
US3981836A (en) * 1964-10-29 1976-09-21 Dan River Inc. Yarn sizes, sizing treatments and resulting sized yarns
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FR936219A (en) 1948-07-13
BE469563A (en) 1900-01-01
GB629097A (en) 1949-09-12

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