US2651587A - Treatment of textile materials - Google Patents

Treatment of textile materials Download PDF

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US2651587A
US2651587A US751995A US75199547A US2651587A US 2651587 A US2651587 A US 2651587A US 751995 A US751995 A US 751995A US 75199547 A US75199547 A US 75199547A US 2651587 A US2651587 A US 2651587A
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yarn
salt
styrene
yarns
maleic acid
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US751995A
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Elmer H Rossin
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated 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
    • Y10T442/2402Coating or impregnation specified as a size
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated 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
    • Y10T442/2861Coated or impregnated synthetic organic fiber fabric
    • Y10T442/2893Coated or impregnated polyamide fiber fabric

Definitions

  • This invention relates to the sizin of nylon warp yarns and threads for the purpcse of improving their weaving characteristics.
  • a further objectofthe invention is to provide a relatively permanentsizingsolutioll WhiQh 92 n be applied to the yarn ,at .room te nperature if desired Without gelling or otherwise becoming unfit for use.
  • wa yarn or thread is treated, as for example the ze box of the con entio al s ashe wi an aqueous solution or dispersionof anammonium, quaternary ammonium, sgglium, potassium or other alkali salt of the copglymer oi styrene and an alkyl ester of maleic acid, aiter which the yarn is dried over dry cans qr by any other suitable method including air drying at roqm temperature.
  • the alkyl esters whieh rney b u dt make the copolymer include-those in which the alkyl group contains frgm l to fl: carbon atoms. including the methyhethyl, DrODy b ty and secondary butyl estersoi maleic acid.
  • The'concentration of thel styrene maleic ester salt in'the bath and the pick-up of. the size box rolls should be adjusted to deposit on the yarnirom 2 to 12% by weight of the salt on the weight" of the yarn, but preferably between about gland 7%.
  • the copolymer'pf styrene and esters of maleic acid used in accordance with this invention is a Well-established product which may be prepared in several ways.
  • One or ell-,known'methods is mass polymerization'w ch 'i'nvolvesheating styrene and an esterof inaleic aci'dat temperatures between about-100 and 300 F; for several hours or mere using tor-each incl of styrene varying amounts oithe jester ofinaleic acid, for example between 0.25 and 4 mols, but preferably in the neighborhood of e'quimolecular quantities.
  • the materials are heated cautibusly, as in a water bath.
  • Another method which may be used is known as the solvent process which involves reacting the styrene and the esters of maleic acid at slightly elevated temperatures in thepresence of 'a solventwhich is capable of dissolving both the starting materials and the Y finished'polymer, such as acetone. If desired, the copolyn' ierization' may be carried'outin' the presence ofa catalystsuch'as benzoylperoxide'.
  • Another method which may be used to prepare the copolymer of'styrene and the alkyl ester of maleic acid involves copolymerizing styreneand maleic anhydride by any of the'standard procedures describedabo've, after which thecopolymer is reacted in' alcohol by the regular chemical procedure for alcoholysis, thereby producing the ester ofthe copolyme'rL It is'also'possible, but not preferred, to mix simultaneously the styrene-maleic anhydride and alcohol and then'polymerize the mixtureby'any of the stand-' ard procedures.
  • Example I A'solution of an ammonium salt of styrenemaleic' acid ester resin was prepared by mixing together 150 parts of the secondary butyl ester of styrene-maleic acid, prepared by copolymerizing equimolecular quantities of styrene and the secondary butyl ester of maleic acid at about 200 F. in a water bath, 100 parts of 26% NHOH and 1750 parts of water. The resulting mixture was then heated from 200 to 212 F. with stirring, and maintained at this temperature until a uniform, somewhat viscous transparent solution resulted.
  • the resulting size was then poured in the size box of a 5 can silk slasher, after which a warp of 200/34/52 nylon yarn was passed at a speed of yards per minute through the size solution, which was maintained at 150 F., and dried on the dry cans at 180 F. By proceeding in this way, excellent weaving was obtained and the resulting fabric was substantially free of floats. The size was easily removed from the finished fabric by washing with warm water.
  • Example II A 7 solution of the sodium salt of the styrenemaleic acid ethyl ester was prepared by mixing together 140 parts of the ethyl ester of styrenemaleic acid, prepared by copolymerizing equimolecular quantities of styrene and the ethyl ester of maleic acid at about 200 F. in a water bath, 60 parts of 50% NaOH and 1800 parts of water. The resulting mixture was then heated from 200 to 212 F. with stirring, and maintained at this temperature until a uniform, somewhat viscous transparent solution resulted, which required about one hour.
  • Example III A solution of an ammonium salt of styrenemaleic acid ester resin was prepared as described in Example I.
  • the resulting size solution was then poured in the size box of a 5 can silk slasher, after which a warp of 200/34/5Z nylon yarn was passed at a speed of 15 yards per minute through the size solution, which was maintained at 150 F., and dried on the dry cans at 180 F.
  • the weaving of the yarn was greatly facilitated and the resulting fabric was substantially free of floats.
  • the fabric was further heated on a tenter frame at 275 R, which produced a semi-permanent somewhat stiffened finish.
  • the fabric prepared from yarn sized in accordance with the present invention has a semi-permanent, genei' ally stifiened finish without further treatment, but if desired, it may be subjected to additional finishing operations.
  • softening agents including such materials as sulfonated oils, soaps, emulsified tallow, emulsified oils, glycerine and the like.
  • aqueous solutions it is to be understood that this is intended to include aqueous dispersions, as it is believed where ammonium salts are employed, the salt is actually present in the form of a colloidal dispersion.
  • the method of sizing nylon warp yarns which comprises treating said yarns with a composition consisting essentially of an aqueous solution of a salt of the copolymer of a substance selected from the group consisting of styrene and substituted styrenes and an alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt being selected from the group consisting of sodium and potassium salts, and then drying said yarns.
  • the method of sizing nylon warp yarns which comprises treating said yarns with a composition consisting essentially of an aqueous solution of a salt of the copolymer of styrene and an alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt being selected from the group consisting of sodium and potassium salts, and then drying the yarns.
  • the method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a salt of the copolymer of styrene and an alkyl ester of inaleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt being selected from the group consisting of sodium and potassium salts and being deposited on said yarn in amounts varying from 2 to 12% by weight, and then drying said yarn.
  • a woven nylon fabric containing nylon warp yarns which are impregnated With a salt of the copolymer of styrene and an 'alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt beingselected from the group consisting of sodium and potassium salts.
  • the method of sizing nylon warp yarns which comprises treating said yarns with a composition consisting essentially of an aqueous solution of the sodium salt of the copolymer of styrene and an alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, and then dryin the yarns.
  • the method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and the secondary butyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 12% by Weight, and then drying said yarn.
  • the method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and the ethyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 1 by weight, and then drying said yarn.
  • the method of sizing a nylonwarp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and the methyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 12% by weight, and then drying said yarn.
  • the method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and a propyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 12% by Weight, and then drying said yarn.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Patented Sept. 8, 1953 TREATMENT OF TEXTILE MATERIALS Ehner Ii. Bossin, Melrose, Mass assignor to Monsanto Chemical Compan poration of Delaware y, St. Louis, Mo., a cor- No Drawing. Application Julie 2,1947, Serial No. 751,995
This invention relates to the sizin of nylon warp yarns and threads for the purpcse of improving their weaving characteristics.
It has been commQn practice to apply starch size solutions to the warp yarn prior to weaving for the purpose of increasing the strength of the y reducin shedding durin passa t o g the loom or for other reasons. Iiqwever, ordinary starch sizes on drying have the disadvantage of dusting to a considerable xt both in the slasher and in the loom- Mor ver, hey do not reduce shedding s s-much as might be desired. Other sizes for nylon yarns that have been used include polyvinyl alcchohprotein sizes and modified starches, but when eUQhsizes are employed, excessive dustingin the loom is found as well as an excessive number of breaks in the warp yarns.
It is a primary object of the present invention to provide sizing o r slashing iormulations, which result in a markedlydecreased amount of dusting and shedding and at the sametime produce yarns of enhancedstrengthand resistance to breakage in the 100m.
A further objectofthe invention is to provide a relatively permanentsizingsolutioll WhiQh 92 n be applied to the yarn ,at .room te nperature if desired Without gelling or otherwise becoming unfit for use.
Still further objects. of the, inventieh Wjill become apparent from the following detailed description and appendedclaim In accomplishing. the above Ob Q 1. wa yarn or thread is treated, as for example the ze box of the con entio al s ashe wi an aqueous solution or dispersionof anammonium, quaternary ammonium, sgglium, potassium or other alkali salt of the copglymer oi styrene and an alkyl ester of maleic acid, aiter which the yarn is dried over dry cans qr by any other suitable method including air drying at roqm temperature. The alkyl esters whieh rney b u dt make the copolymer include-those in which the alkyl group contains frgm l to fl: carbon atoms. including the methyhethyl, DrODy b ty and secondary butyl estersoi maleic acid. The'concentration of thel styrene maleic ester salt in'the bath and the pick-up of. the size box rolls should be adjusted to deposit on the yarnirom 2 to 12% by weight of the salt on the weight" of the yarn, but preferably between about gland 7%. Although good results may be 'obtainedjinjsome instances, as when a heavy yarn is treated, by using the bath at room temperatures, it is usually desirable to have-the bath or solution at somewhat elevated temperatures, usually" between about Claims. (Cl. 117138. 8)
and F., to insure uniform penetration. In the eventthat a'semipermanent finish is desired on the warp threads, it is necessary, when ammonium salts are used, to dry the warp yarns, or the fabric prepared therefrom, at a sufficiently elevated temperature to setthe resinQj' Under such circumstances, the yarn is heated preferably at 250 to 300 F. during drying,but satisfactory results may be obtainedat temperatures as low as 200 F. When sodium or potassium salts are used, however, it is not essential to-dryat elevated temperatures, but when a semi-permanent finish is desired theyarns, or the fabric prepared therefroin'rnust be subjected to a dilute acid finishing bath in order to set the resin on the yarn or fabric.
The copolymer'pf styrene and esters of maleic acid used in accordance with this invention is a Well-established product which may be prepared in several ways. One or ell-,known'methods is mass polymerization'w ch 'i'nvolvesheating styrene and an esterof inaleic aci'dat temperatures between about-100 and 300 F; for several hours or mere using tor-each incl of styrene varying amounts oithe jester ofinaleic acid, for example between 0.25 and 4 mols, but preferably in the neighborhood of e'quimolecular quantities. Preferably, the materials are heated cautibusly, as in a water bath. Another method which may be used is known as the solvent process which involves reacting the styrene and the esters of maleic acid at slightly elevated temperatures in thepresence of 'a solventwhich is capable of dissolving both the starting materials and the Y finished'polymer, such as acetone. If desired, the copolyn' ierization' may be carried'outin' the presence ofa catalystsuch'as benzoylperoxide'.
Another method which may be used to prepare the copolymer of'styrene and the alkyl ester of maleic acid involves copolymerizing styreneand maleic anhydride by any of the'standard procedures describedabo've, after which thecopolymer is reacted in' alcohol by the regular chemical procedure for alcoholysis, thereby producing the ester ofthe copolyme'rL It is'also'possible, but not preferred, to mix simultaneously the styrene-maleic anhydride and alcohol and then'polymerize the mixtureby'any of the stand-' ard procedures.
A further understanding of the invention will be obtained iromthe'following examples, the parts being given by weight:
Example I A'solution of an ammonium salt of styrenemaleic' acid ester resin was prepared by mixing together 150 parts of the secondary butyl ester of styrene-maleic acid, prepared by copolymerizing equimolecular quantities of styrene and the secondary butyl ester of maleic acid at about 200 F. in a water bath, 100 parts of 26% NHOH and 1750 parts of water. The resulting mixture was then heated from 200 to 212 F. with stirring, and maintained at this temperature until a uniform, somewhat viscous transparent solution resulted. This required about one hour, The resulting size was then poured in the size box of a 5 can silk slasher, after which a warp of 200/34/52 nylon yarn was passed at a speed of yards per minute through the size solution, which was maintained at 150 F., and dried on the dry cans at 180 F. By proceeding in this way, excellent weaving was obtained and the resulting fabric was substantially free of floats. The size was easily removed from the finished fabric by washing with warm water.
Example II A 7 solution of the sodium salt of the styrenemaleic acid ethyl ester was prepared by mixing together 140 parts of the ethyl ester of styrenemaleic acid, prepared by copolymerizing equimolecular quantities of styrene and the ethyl ester of maleic acid at about 200 F. in a water bath, 60 parts of 50% NaOH and 1800 parts of water. The resulting mixture was then heated from 200 to 212 F. with stirring, and maintained at this temperature until a uniform, somewhat viscous transparent solution resulted, which required about one hour. After cooling the resulting solution to 125 F., it was poured into the size box of a 7 can Johnson slasher, after which a warp of 200/34/52 nylon was passed through the solution and dried on the dry cans in the usual manner. The treated yarn was then rolled up on a beam and woven. As a result of treating the yarn in the above manner prior to weaving, numerous improvements were noted in the weaving process and in the resulting fabric, including a smaller number of broken ends, fewer broken filaments, and a final fabric which is smoother and more uniform than fabrics woven in the customary way. The size was easily removed from the finished fabric by washing with warm water.
Example III A solution of an ammonium salt of styrenemaleic acid ester resin was prepared as described in Example I. The resulting size solution was then poured in the size box of a 5 can silk slasher, after which a warp of 200/34/5Z nylon yarn was passed at a speed of 15 yards per minute through the size solution, which was maintained at 150 F., and dried on the dry cans at 180 F. As a result of the above treatment, the weaving of the yarn was greatly facilitated and the resulting fabric was substantially free of floats. The fabric was further heated on a tenter frame at 275 R, which produced a semi-permanent somewhat stiffened finish.
By treating nylon warp yarns with the sizing agents described herein, it is possible to carry out the weaving with a minimum amount of dusting and shedding and with the atmosphere of the room at relatively low humidities. The treated yarn is exceptionally strong and pliable and resistant to abrasion with the result that the number of breaks occurring during weaving is reduced to a minimum. Moreover, the fabric prepared from yarn sized in accordance with the present invention has a semi-permanent, genei' ally stifiened finish without further treatment, but if desired, it may be subjected to additional finishing operations. When goods are sized in the conventional manner with starches, gums or the like, it is necessary to desize before dyeing or finishing, as these commonly used sizes retard or interfere with the absorption of dyestuffs or finishing agents. When salts of styrene-maleic ester resin are employed however, particularly the ammonium salts, it is possible to eliminate the expensive and cumbersome step of desizing and to dye and finish the fabric evenly and uniformly.
In some cases it is advantageous to add small amounts of softening agents to the size bath, including such materials as sulfonated oils, soaps, emulsified tallow, emulsified oils, glycerine and the like.
It is customary to apply the sizing materials described herein to yarns. 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 to obtain yarns of the desired weaving characteristics. Fabrics prepared from such yarns also have the desired semi-permanent finish hereinbefore mentioned.
Where reference is made in the appended claims to aqueous solutions, it is to be understood that this is intended to include aqueous dispersions, as it is believed where ammonium salts are employed, the salt is actually present in the form of a colloidal dispersion.
What is claimed is:
1. The method of sizing nylon warp yarns which comprises treating said yarns with a composition consisting essentially of an aqueous solution of a salt of the copolymer of a substance selected from the group consisting of styrene and substituted styrenes and an alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt being selected from the group consisting of sodium and potassium salts, and then drying said yarns.
2. The method of sizing nylon warp yarns which comprises treating said yarns with a composition consisting essentially of an aqueous solution of a salt of the copolymer of styrene and an alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt being selected from the group consisting of sodium and potassium salts, and then drying the yarns.
3. The method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a salt of the copolymer of styrene and an alkyl ester of inaleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt being selected from the group consisting of sodium and potassium salts and being deposited on said yarn in amounts varying from 2 to 12% by weight, and then drying said yarn.
4. A nylon warp yarn impregnated with a salt of the copolymer of styrene and an alkyl ester of maleic acid, in which the'alkyl group contains from 1 to 4. carbon atoms, said salt being selected from the group consisting of sodium and potassium salts.
5. A woven nylon fabric containing nylon warp yarns which are impregnated With a salt of the copolymer of styrene and an 'alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, said salt beingselected from the group consisting of sodium and potassium salts.
6. The method of sizing nylon warp yarns which comprises treating said yarns with a composition consisting essentially of an aqueous solution of the sodium salt of the copolymer of styrene and an alkyl ester of maleic acid, in which the alkyl group contains from 1 to 4 carbon atoms, and then dryin the yarns.
7. The method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and the secondary butyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 12% by Weight, and then drying said yarn.
8. The method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and the ethyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 1 by weight, and then drying said yarn.
9. The method of sizing a nylonwarp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and the methyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 12% by weight, and then drying said yarn.
10. The method of sizing a nylon warp yarn which comprises treating said yarn with a composition consisting essentially of an aqueous solution of a sodium salt of the copolymer of styrene and a propyl ester of maleic acid, said salt being deposited on said yarn in amounts varying from 2 to 12% by Weight, and then drying said yarn.
ELMER H. ROSSIN.
References Cited in the me of this patent UNITED STATES PATENTS Number Name Date 1,976,679 Fikentscher et al. Oct. 9, 1934 2,047,398 Voss et a1. July 14, 1936 2,300,566 Hahn et al. Nov. 3, 1942 2,324,601 Spanagel July 20, 1943 2,324,739 Stoops et a1. July 20, 1943 2,402,625 Martin June 25, 1946 2,469,407 Powers et a1 May 10, 1949 2,469,408 Powers et a1. May 10, 1949 2,469,409 Powers et a1. May 10, 1949 2,537,018 Barrett Jan. 9, 1951 2,586,477 Niles Feb. 19, 1952

Claims (1)

1. THE METHOD OF SIZING NYLON WARP YARNS WHICH COMPRISES TREATING SAID YARNS WITH A COMPOSITION CONSISTING ESSENTIALLY OF AN AQUEOUS SOLUTION OF A SALT OF THE COPOLYMER OF A SUBSTANCE SELECTED FROM THE GROUP CONSISTING OF STYRENE AND SUBSTITUTED STYRENES AND AN ALKYL ESTER OF MALEIC ACID, IN WHICH THE ALKYL GROUP CONTAINS FROM 1 TO 4 CARBON ATOMS, SAID SALT BEING SELECTED FROM THE GROUP CONSISTING OF SODIUM AND POTASSIUM SALTS, AND THEN DRYING SAID YARNS.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2807865A (en) * 1954-06-14 1957-10-01 Rohm & Haas Sized textile and method of fabricating yarn into fabric
US2854357A (en) * 1955-09-06 1958-09-30 Monsanto Chemicals Sized nylon yarns and method for producing same
US2874069A (en) * 1954-03-12 1959-02-17 Deering Milliken Res Corp Method for reducing the pilling tendencies of fabrics
US2899341A (en) * 1959-08-11 Textile finishing process
US3084070A (en) * 1958-09-02 1963-04-02 Dow Chemical Co Warp size comprising high molecular weight styrene/maleic anhydride copolymer
US3161538A (en) * 1962-06-15 1964-12-15 Gen Aniline & Film Corp Method of treating textile materials
US3854990A (en) * 1970-12-16 1974-12-17 Monsanto Co Process for sizing textile materials
US3983271A (en) * 1964-10-29 1976-09-28 Dan River Inc. Yarn sizes, sizing treatments and resulting sized yarns

Citations (11)

* 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
US2300566A (en) * 1939-03-10 1942-11-03 Gen Aniline & Film Corp Process of preparing polymerization products
US2324739A (en) * 1939-09-22 1943-07-20 Carbide & Carbon Chem Corp Enamel coating
US2324601A (en) * 1940-09-21 1943-07-20 Du Pont Sizing
US2402625A (en) * 1941-11-12 1946-06-25 Standard Telephones Cables Ltd Antenna switching device
US2469408A (en) * 1945-12-01 1949-05-10 Monsanto Chemicals Treatment of textile material
US2469409A (en) * 1945-12-01 1949-05-10 Monsanto Chemicals Treatment of textile materials
US2469407A (en) * 1945-12-01 1949-05-10 Monsanto Chemicals Treatment of textile materials
US2537018A (en) * 1948-05-29 1951-01-09 Monsanto Chemicals Copolymer and coating composition
US2586477A (en) * 1947-08-27 1952-02-19 Monsanto Chemicals Treatment of textile materials

Patent Citations (11)

* 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
US2300566A (en) * 1939-03-10 1942-11-03 Gen Aniline & Film Corp Process of preparing polymerization products
US2324739A (en) * 1939-09-22 1943-07-20 Carbide & Carbon Chem Corp Enamel coating
US2324601A (en) * 1940-09-21 1943-07-20 Du Pont Sizing
US2402625A (en) * 1941-11-12 1946-06-25 Standard Telephones Cables Ltd Antenna switching device
US2469408A (en) * 1945-12-01 1949-05-10 Monsanto Chemicals Treatment of textile material
US2469409A (en) * 1945-12-01 1949-05-10 Monsanto Chemicals Treatment of textile materials
US2469407A (en) * 1945-12-01 1949-05-10 Monsanto Chemicals Treatment of textile materials
US2586477A (en) * 1947-08-27 1952-02-19 Monsanto Chemicals Treatment of textile materials
US2537018A (en) * 1948-05-29 1951-01-09 Monsanto Chemicals Copolymer and coating composition

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2899341A (en) * 1959-08-11 Textile finishing process
US2874069A (en) * 1954-03-12 1959-02-17 Deering Milliken Res Corp Method for reducing the pilling tendencies of fabrics
US2807865A (en) * 1954-06-14 1957-10-01 Rohm & Haas Sized textile and method of fabricating yarn into fabric
US2854357A (en) * 1955-09-06 1958-09-30 Monsanto Chemicals Sized nylon yarns and method for producing same
US3084070A (en) * 1958-09-02 1963-04-02 Dow Chemical Co Warp size comprising high molecular weight styrene/maleic anhydride copolymer
US3161538A (en) * 1962-06-15 1964-12-15 Gen Aniline & Film Corp Method of treating textile materials
US3983271A (en) * 1964-10-29 1976-09-28 Dan River Inc. Yarn sizes, sizing treatments and resulting sized yarns
US3854990A (en) * 1970-12-16 1974-12-17 Monsanto Co Process for sizing textile materials

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