US3576592A - Process for permanently pressing textile articles made of keratinic fibers - Google Patents

Process for permanently pressing textile articles made of keratinic fibers Download PDF

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Publication number
US3576592A
US3576592A US528762A US3576592DA US3576592A US 3576592 A US3576592 A US 3576592A US 528762 A US528762 A US 528762A US 3576592D A US3576592D A US 3576592DA US 3576592 A US3576592 A US 3576592A
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United States
Prior art keywords
crease
polysulfhydrylated
solution
polymer
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US528762A
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English (en)
Inventor
Charles Zviak
Andre Viout
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from FR6590A external-priority patent/FR1458123A/fr
Priority claimed from FR27374A external-priority patent/FR1502624A/fr
Application filed by LOreal SA filed Critical LOreal SA
Application granted granted Critical
Publication of US3576592A publication Critical patent/US3576592A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5207Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/30Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/34Introducing sulfur atoms or sulfur-containing groups
    • 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
    • D06M15/273Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups
    • D06M15/2735Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having epoxy groups of unsaturated carboxylic esters having mercapto groups
    • 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
    • D06M15/285Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00Chemical modification of a polymer
    • C08F2810/50Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority

Definitions

  • the present invention relates to a new process for permanently pressing cloth or knitted materials made of wool, so that it will be resistant to wrinkles and permanently retain creases made therein at the time of treatment.
  • creases may be obtained according to the invention in a simple and durable manner without causing damage to or weakening of the physical properties of the textile articles.
  • One object of the present invention is to present a new process for making creases in textile articles made of keratinic fibers, this new process being characterized by the fact that the above-mentioned textile articles are impregnated with a basic solution of polysulfhydrylated polymers, then heated and pressed in the area in which a crease is desired, for example, by using an iron.
  • the solution to be applied to the textile article contains about 1 to and preferably from 2 to 6% by weight of polysulfhydrylated polymers.
  • the pH of this solution is between about 3.5 and 10 and is preferably between 9 and 9.5.
  • polysulfhydrylated polymers which can be used to carry out the process according to the invention, are the polysulfhydrylated polymers corresponding to the following formula:
  • Patented Apr. 27, 1971 ice or a --OCOCH radical, or a COOCH radical, or a CN radical, n is a whole number.
  • the polysulfhydrylated polymers are of the formula:
  • R is a hydrogen atom or a lower alkyl such as CH or C H or a lower hydroxy alkyl such as R is a hydrogen atom or a -CH radical
  • q is a whole number between 2 and 6, inclusive
  • p is a whole number equal to 0 or 1
  • R and R" are hydrogen atoms or lower alkyl radicals, or phenyl radicals, or lower alkyloxy radicals, R and R being the same or different,
  • R" is a hydrogen atom, or the -OCOCH radical, or the CEN radical, or the COOCH radical,
  • n is a whole number.
  • the polysulfhydrylated polymers are of the formula:
  • R and R" which may be the same or different are hydrogen atoms, or lower alkyl radicals, or phenyl radicals, or lower alkyloxy radicals,
  • R" is a hydrogen atom, or the OCOCH radical, or
  • n is a whole number
  • Q is a radical represented by the following formula:
  • R1 is H or CH3
  • R is H or COOH
  • q is a whole number from 1 to 5, inclusive
  • q is equal to 0 or 1
  • p is equal to 0 or 1
  • Q is a radical represented by the following formula:
  • R is a hydrogen atom or a lower alkyl
  • R is a lower alkyl, or a radical or formula r and r being the same or different lower alkyls, or being part of a heterocyclic ring such as that of morpholine or piperidine, m is a whole number equal to 2, 3 or 4.
  • the polysulfhydrylated polymers are constituted by an anhydride homopolymer on which at least one mercapto-amine is condensed.
  • the homopolymer may be a maleic polyanhydride polymer, an itaconic polyanhydride polymer, an acrylic polyanhydride polymer, a mixed acrylic-methacrylic polyanhydride polymer, or a methacrylic polymer, although this list is not exhaustive.
  • Aminothiols having the following formula may be used to sulfhydrylate these homopolymers:
  • R is an alkylene radical comprising preferably from 2 to 4 carbon atoms, which may be substituted by lower alkyls which may have up to 4 carbon atoms, or a carboxyl radical, or a carbalkyloxy group, and
  • R is a hydrogen atom or a lower alkyl such as CH Among the aminothiols corresponding to the above formula, these may be cited as examples:
  • R is H, --CH C H or CH CH OH, R is H or -COOH, q is a whole number between 1 and 5, inclusive, q is equal to 0 or 1, p is equal to O or 1.
  • mercapto-amide amines corresponding to this last formula may be cited those which are obtained from esters of thioglycolic acid, thiolactic acid or ,B-mercaptopropionic acid and from diamines such as ethylene diamine, hexamethylene diamine, N-hydroxyethyl ethylene diamine.
  • Another object of the present invention is to provide a new article of manufacture which consists of a composition for permanently creasing textile articles made from keratinic fibers.
  • This composition is essentially characterized by the fact that it contains at least one polysulfhydrylated polymer and a base, the pH of this composition being between about 3.5 and and being preferably between 9 and 9.5.
  • this last is placed in an aerosol bomb with a liquified gas propellant under pressure, from which it is permitted to escape as a lather or a jet of liquid which may be atomized.
  • Res l SMA 1000A having the formula:
  • the woolen cloth in which a permanent crease is desired is dampened with this solution; then the cloth is ironed to impress the crease using a hot iron and a damp cloth. 7
  • EXAMPLE 2 A composition to obtain permanent creases in textile articles of keratinic fibers is prepared as follows:
  • a polysulfhydrylated polymer as in Example 1 above 40 Ammonia at 20 B. to bring the pH of the solution to 9.5, about cc 60 De-ionized water g 900
  • the following mixture is then placed in an aerosol container:
  • Solution A 70 Dichlorodifluoromethane 15 Trichloromonofluoromethane 15
  • the solution contained in the bomb is sprayed onto the textile article to be creased, then a crease is formed using a hot iron and a damp cloth.
  • the permanent press thus obtained holds up well even when the cloth is placed in boiling water for an hour.
  • Example 6 A polysulfhydrylated polymer as in Example 5 g 1.5 Ammonia at 20 B. q.s.p. pH 9.3. Silicone anti-foaming agent g 0.4 Water, q.s.p cc 100 The following mixture is then put in an aerosol container:
  • a composition according to the invention which is in the form of a transient aerosol lather is made by first preparing a solution D having the following composition:
  • the cloth to be treated is dampened by rolling the ball of the applicator over the area where pressing is desired, then ironing it with a hot iron.
  • a composition according to the invention is made in the form of an aerosol by first preparing a solution C having the following composition:
  • Silicone anti-foaming agent g 0.4 Polyethoxyether of alkylphenol g 0.2. Water, q.s.p cc 100 A mixture of the following is then placed in an aerosol bomb:
  • Pressing is then done as in the preceding example, using a hot iron and a damp cloth and equally good results are obtained.
  • EXAMPLE 8 A composition is prepared by mixing:
  • Woolen cloth is pressed as in the preceding examples, using a hot iron and a damp cloth.
  • the permanent press thus obtained holds up well, even when the cloth is immersed in hot water for an hour.
  • a crease is made in a woolen cloth as in the preceding examples using a hot iron and a damp cloth; the crease thus obtained holds up well even when immersed in hot 'water for an hour, and remains after several washings.
  • a composition according to the invention is prepared by mixing:
  • the woolen cloth in which a permanent crease is desired is dampened with this solution.
  • the cloth is ironed with a hot iron and a damp cloth to impress the crease nd a permanent crease is obtained which remains even ter several washings.
  • the cloth to be treated is dampened by rolling the ball of the applicator over the area in which a crease is desired, then ironing with a hot iron.
  • the crease may be formed in the textile article without using a hand iron by using another method such as a pressing machine which permits the simultaneous application of heat and pressure.
  • the process according to the invention permits the formation of all sorts of creases in textile articles other than woven cloths.
  • the process according to the invention permits the formation of creases in knitted materials, laces, felts and generally in keratinic textile fibers assembled in any manner whatever.
  • the process according to the invention is not limited to textile processes carried out using exclusively keratinic fibers such as wool, alpaca, camels hair or mohair, for treatment according to the invention may be possible even if these keratinic fibers are mixed with other natural, artificial or synthetic textile fibers.
  • a process for permanently pressing textile articles containing wool fibers which comprises impregnating the textile with an aqueous solution containing 1-20 weight of I-S, q is equal to or 1 and p is equal to O or I, O is a radical of the formula percent of a polysulfhydrylated polymer selected from the group consisting of:
  • hydrogen and -CH R is selected from the group consisting of hydrogen and -COOH, q is an integer

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Textile Engineering (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Cosmetics (AREA)
US528762A 1965-02-23 1966-02-21 Process for permanently pressing textile articles made of keratinic fibers Expired - Lifetime US3576592A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR6590A FR1458123A (fr) 1965-02-23 1965-02-23 Nouveau procédé pour réaliser des plis permanents sur des articles textiles à base de fibres kératiniques et nouveaux produits pour la mise en oeuvre de ce procédé
FR27374A FR1502624A (fr) 1965-08-05 1965-08-05 Homopolymères polysulfhydrylés, procédé de préparation et applications de ces polymères

Publications (1)

Publication Number Publication Date
US3576592A true US3576592A (en) 1971-04-27

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US528762A Expired - Lifetime US3576592A (en) 1965-02-23 1966-02-21 Process for permanently pressing textile articles made of keratinic fibers

Country Status (4)

Country Link
US (1) US3576592A (de)
DE (1) DE1619132A1 (de)
GB (1) GB1101628A (de)
NL (1) NL6602090A (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3753649A (en) * 1970-02-26 1973-08-21 Ciba Geigy Ag Treatment of keratinous fibres and fabrics
FR2806274A1 (fr) * 2000-03-14 2001-09-21 Oreal Applicateur a bille contenant une composition capilaire
US20030064043A1 (en) * 2000-04-01 2003-04-03 Beate Dannecker Method and agents on the basis of 2-mercaptopropionic acid amides for durable hair forming adn a method for producing same
US20030103929A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US20030103927A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US20030103926A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a dimethicone, a nacreous agent and a cationic polymer, and uses thereof
US20030108503A1 (en) * 2001-09-11 2003-06-12 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US20030108578A1 (en) * 2001-09-11 2003-06-12 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof
JP2005503474A (ja) * 2001-09-26 2005-02-03 スミス アンド ネフュー ピーエルシー 構造により特徴付けられている機能をもつ重合体
CN110655609A (zh) * 2019-04-30 2020-01-07 杭州肄康新材料有限公司 一种纺织染料固色剂及其应用

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8598279B2 (en) * 2007-07-23 2013-12-03 Henkel IP US LLC Adducts useful as cure components for anaerobic curable compositions

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3753649A (en) * 1970-02-26 1973-08-21 Ciba Geigy Ag Treatment of keratinous fibres and fabrics
FR2806274A1 (fr) * 2000-03-14 2001-09-21 Oreal Applicateur a bille contenant une composition capilaire
EP1138315A1 (de) * 2000-03-14 2001-10-04 L'oreal Kugelauftragvorrichtung die ein Haarbehandlungsmittel enthalt
US6635262B2 (en) 2000-03-14 2003-10-21 L'oreal S.A. Roll-on applicator comprising a hair composition
US20030064043A1 (en) * 2000-04-01 2003-04-03 Beate Dannecker Method and agents on the basis of 2-mercaptopropionic acid amides for durable hair forming adn a method for producing same
US7341715B2 (en) 2000-04-01 2008-03-11 Wella Ag Method and agents on the basis of 2-mercaptopropionic acid amides for durable hair forming and a method for producing same
US20030108578A1 (en) * 2001-09-11 2003-06-12 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof
US20030108503A1 (en) * 2001-09-11 2003-06-12 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US20030103926A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a dimethicone, a nacreous agent and a cationic polymer, and uses thereof
US20030103927A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
US20040001796A9 (en) * 2001-09-11 2004-01-01 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a dimethicone, a nacreous agent and a cationic polymer, and uses thereof
US7258852B2 (en) 2001-09-11 2007-08-21 L'oreal S.A. Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof
US20030103929A1 (en) * 2001-09-11 2003-06-05 Mireille Maubru Cosmetic compositions containing a methacrylic acid copolymer, a silicone and a cationic polymer, and uses thereof
JP2005503474A (ja) * 2001-09-26 2005-02-03 スミス アンド ネフュー ピーエルシー 構造により特徴付けられている機能をもつ重合体
US20050032929A1 (en) * 2001-09-26 2005-02-10 Bryan Greener Polymers with structure-defined functions
US7955594B2 (en) 2001-09-26 2011-06-07 Smith & Nephew, Plc Polymers with structure-defined functions
US8506945B2 (en) 2001-09-26 2013-08-13 Smith & Nephew, Plc. Polymers with structure-defined functions
CN110655609A (zh) * 2019-04-30 2020-01-07 杭州肄康新材料有限公司 一种纺织染料固色剂及其应用
CN110655609B (zh) * 2019-04-30 2021-11-02 浙江新海天生物科技有限公司 一种纺织染料固色剂及其应用

Also Published As

Publication number Publication date
DE1619132A1 (de) 1971-03-11
GB1101628A (en) 1968-01-31
NL6602090A (de) 1966-08-24

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