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

Info

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
Authority
US
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
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/en
Priority claimed from FR27374A external-priority patent/FR1502624A/en
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

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General 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
    • D06P1/44—General 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
    • D06P1/52—General 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
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/525—Polymers of unsaturated carboxylic acids or functional derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—Compositions 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)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
    • 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
    • D06M15/273—Macromolecular 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
    • D06M15/2735—Macromolecular 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
    • 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
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/50—Chemical 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Cosmetics (AREA)

Abstract

THE METHOD OF PERMANENTLY PRESSING TEXTILE ARTICLES CONTAINING KERATINIC FIBER, WHICH COMPRISES THE STEPS OF IMPREGANTING THE TEXTILE ARTICLE WITH A SOLUTION CONTAINING EFFECTIVE AMOUNTS OF A WATER SOLUBLE POLYMER HAVING BRANCHED CHAINS HAVING TERMINAL-SH FUNCTIONAL GROUPS, PLACING THE IMPREGNATED TEXTILE ARTICLE IN THE CONFIGURATION CORRESPONDING TO THE SHAPE DESIRED, AND THEN PRESSING THE AREA IN WHICH A CREASE IS DESIRED AT AN ELEVATED TEMPERATURE.

Description

United States Patent 3,576,592 PROCESS FOR PERMANENTLY PRESSING TEXTILE ARTICLES MADE OF KERATINIC FIBERS Charles Zviak, Franconville, and Andre Viout, Paris, France, assignors to Societe Anonyme dite: LOreal No Drawing. Filed Feb. 21, 1966, Ser. No. 528,762 Claims priority, application France, Feb. 23, 1965,
90; Aug. 5, 1965, 27,374 Int. Cl. C09k 3/30; D06m /12 US. Cl. 8-1276 2 Claims ABSTRACT OF THE DISCLOSURE The method of permanently pressing textile articles containing keratinic fibers, which comprises the steps of impregnating the textile article with a solution containing effective amounts of a water soluble polymer having branched chains having terminal SH functional groups, placing the impregnated textile article in the configuration corresponding to the shape desired, and then pressing the area in which a crease is desired at an elevated temperature.
It is known that it is desirable to impress creases in the most durable manner possible on textile articles, for example, creases in pants or in pleated skirts.
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.
These 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.
According to the invention, 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.
Among the polysulfhydrylated polymers which can be used to carry out the process according to the invention, are the polysulfhydrylated polymers corresponding to the following formula:
R!!! CH-(J CH-CH- 611 int in which:
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:
in which:
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:
IIZII RI! CH-(IJ(IZH---CH-CH(IJCH-CH R R COOH o0 R R COOH ([30 Q. Q, n
in which:
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
the COOCH radical, or the --CEN radical,
n is a whole number,
Q is a radical represented by the following formula:
in which:
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:
in which:
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:
fi-mercaptoethylamine, cysteine, and ethyl cysteinate.
Mercapto-amide amines of the following formula may also be used to sulfhydrylate the homopolymers:
in which:
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.
Among the 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.
It is equally possible to condense amines not made up of SH groups on the anhydride homopolymers, with simultaneous condensation of the mercapto-amines.
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.
In a preferred method of treating with aforementioned composition 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.
In order that the invention may be better understood, several embodiments thereof will now be described, purely by way of example, without limiting the scope of the invention to the specific details thereof.
mercaptoethylamine with the styrene/maleic anhydride copolymer sold by the Texas Butadiene Chemical Corp.
under the trademark Res l SMA 1000A having the formula:
CHCHzCH-CH- OOOH I00 1'; (1H,
CH2 SIH n De-ionized water--959 g.
Monethanol to bring the pH of the solution to 9.5 about 11 g.
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
When the cloth has dried and cooled off, it has a permanent crease which remains even after several washings.
EXAMPLE 2 A composition to obtain permanent creases in textile articles of keratinic fibers is prepared as follows:
First solution A having the following composition is prepared:
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 To use the composition, which is in the form of an aerosol, 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.
EXAMPLE 3 To prepare a composition according to the invention in the form of a transient lather spread by an aerosol bomb, the following process is used:
First solution B having the following composition is prepared:
A polysulfhydrylated polymer as in Example 1 above g 30 De-ionized Water g 920 Ammonia at 20 B. to bring the pH to 9.5,
about cc 45 Silicone anti-foaming agent g 4 Polyethoxyether of a fatty alcohol g 1 After this a mixture consisting of the following is placed in a special container:
G. Solution B Dichlorodifluoromethane 15 EXAMPLE 4 A composition according to the invention is obtained by mixing:
A polysulfhydrylated polymer obtained by condensation of a mol of fi-mercaptoethylamine on a mol of maleic anhydride/ ethylene copolymer sold by the Monsanto Corp. under the trademark Resin DX 840.11 having the formula:
Ammonia at 20 B. q.s.p. pH=9.3. Distilled water q.s.p. 100 cc.
20 A crease 1s made 1n a woolen cloth 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 placed in boiling water for an hour.
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:
G. Solution C 85 Butane The contents of the areosol bomb are sprayed onto the cloth to be treated in the area where pressing is desired. A crease is formed using a hot iron and a damp cloth.
Good quality pressing is obtained.
EXAMPLE 7 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:
A polysulfhydrylated polymer obtained by condensing fi-mercaptoethylamine and N,N-diethyl-propylene diamine on an ethylene/maleic anhydride copolymer having the formula:
EXAMPLE 5 A solution having the following composition is placed in a roll-on-applicator:
A polysulfhydrylated polymer obtained by condensing a N-(fi-aminoethyl) thioglycolamide on a ethylene/maleic anhydride copolymer sold under the trademark Resin DX.840.11 by the Monsanto Chemical Co., this polymer having the formula:
Ammonia at B. q.s.p. pH=9.3. Distilled water q.s.p. 100 cc.
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.
Thus a crease with excellent holding power is obtained.
EXAMPLE 6 A composition according to the invention is made in the form of an aerosol by first preparing a solution C having the following composition:
Ammonia at 20 B. q.s.p. pH 9.3.
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:
G. Solution D Dichlorodifluoromethane 15 The aerosol bomb has an atomizing valve which permits a ribbon of lather to be placed on the textile article to be treated, in the area of pressing. The lather disappears rapidly, impregnating the cloth below it with liquid.
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:
A polysulfliydrylated polymer obtained by condensing B-mercaptoethylamine and n-butylamine on a vinyl acetate/maleic anhydride copolymer having the formula:
COOH CO OCOCHa 1|IH OCOCHs NH 3g.
CH2 0 H; 2 (EH: SH :1
Ammonia at 20 B. q.s.p. pH=9.3
75 Distilled water, q.s.p. cc.
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.
EXAMPLE 9 Ammonia at 20 B. q.s.p. pH=9.3 Distilled water, q.s.p. 100 cc.
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.
EXAMPLE 10 A composition according to the invention is prepared by mixing:
A polysulfhydrylated polymer obtained by condensing fi-mercaptoethylamine on a maleic anhydride/vinyl acetate copolymer having the formula:
Ammonia at 20 B q.s.p. pH=9.3 Distilled water, q.s.p. 100 cc.
Using the same method as in the preceding examples, a permanent crease is obtained which holds up very well during several washings with very hot water.
EXAMPLE 11 I S H n De-ionized water 959 g. Monoethanolamine to bring the pH of the solution to 9.5 about 11 g.
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.
8 EXAMPLE 12 A composition to make permanent creases in textile articles made of keratinic' fibers is prepared as follows:
First a solution E having the following composition is prepared:
The polysulfhydrylated homopolymer mentioned in Example 11 g 40 Ammonia at 22 B. to bring the pH to 9.5,
about cc 65 De-ionized water, q.s.p g 1000 The following mixture is then placed in an aerosol bomb:
G. The aforementioned solution E 70 Dichlorodifiuoromethane 15 Trichloromonofluorornethane 15 To use the composition which is in the form of an aerosol, the solution contained in the bomb is sprayed onto the textile article at the place at which a crease is desired; then the crease is formed using a hot iron and a damp cloth.
EXAMPLE 13 To make a permanent crease in a textile article made of keratinic fibers, a solution having the following composition is placed in a roll-on applicator:
A polysulfhydrylated homopolymer having the formula:
CH CH CH--CH 30 OH 70 00 OH O O I IH NH 12 C|4HP 2 CH2 S H n Ammonia at 20 B. q.s.p. pH:9.3. Distilled water, q.s.p. cc.
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.
A crease with excellent holding power is thus obtained. v t
It is clear that the process according to the invention permits the easy and efficient formation of creases in textile articles made of keratinic fibers such as wool.
It should be understood that the above-described embodiments of the invention may be modified as to detail without thereby going outside the scope of the invention.
In particular, it goes without saying that 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.
It goes equally without saying that the process according to the invention permits the formation of all sorts of creases in textile articles other than woven cloths. In particular, 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.
Finally, it is obvious that 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.
What is claimed is:
1. 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:
(a) water-soluble polysulfhydrylated polymer having recurring units of the formula (0) a water-soluble polysulfhydrylated polymer having recurring units of the formula RI! RI! CH( J-CHCH-CH( J-CHOH f wherein R is selected from the group consisting of --CH-C OHCH hydrogen and lower alkyl, R is selected from the 0:9 group consisting of lower alkyl and 611 its I!L N I s11 wherein R is selected from the group consisting of Wherem alkylene having 2 to 4 carbon atoms, lower alkyl 15 T substituted lower alkylene, carboxy substituted lower alkylene and carbalkoxy substituted lower alkylene, I R is selected from the group consisting of hydrogen 7 and lower alkyl, R is selected from the group conis selected from the group consisting of lower alkyl i ti f hydrogen, lower lk l, h l d lower amines and a heterocyclic ring selected from the alkoxy, R" is selected from the group consisting of group Consisting of morpholino and Pipefidino rings hydrogen lower alkyl, phenyl and lower alkoxy and and m is anintegef of and R'" is selected from the group Consisting of (d) a water-soluble polysulfhydrylated polymer con- MOCOCHS, .COOCH3 and densed from (1) an anhydride polymer selected from (b) a water-soluble polysulfhydrylated polymer havthe group Consisting of P l/( y anhydride), P y ing r rrin it f th for l (itaconic anhydride) poly(mixed acrylic-methacrylic anhydride), poly(methacrylic anhydride) and poly (maleic anhydride), and (2) a member selected from the group consisting of Z (i) an aminothiol of the formula f= HS-RNRR' 0H N-R1 wherein R is selected from the group consisting of QQ lower alkylene having 2-4 carbon atoms, lower alkyl substituted lower alkylene, carboxy substituted lower 13:0 alkylene and carbalkoxy substituted lower alkylene and R is lower alkyl and E 2 (ii) a mercapto-amide amine of the formula R1 R2 sH 40 HN-oH- oHz)q[NH-oo-on(o1r2)p1q's1r wherein R is selected from the group consisting of wherein R is selected from the group consisting of hydrogen, CH -C H and --CH CH OH, R hydrogen, lower alkyl and hydroxy low r alkyl, R2 is selected from the group consisting of hydrogen and 1s selected from the group consisting of hydrogen -COOH, q is an integer of 1-5, q is equal to 0 or and s q is an integer of P is equal to 0 0r 1 and p is equal to 0 or 1, said solution having a 1, R and R" are selected from the group consisting H ranging from 35-10, placing the impregnated of hydrogen, lower alkyl, P y and lower Ys textile article in the configuration corresponding to and R i Selected from the g p consisting of ythe shape desired and pressing said textile article at a, and a an elevated temperature.
2. The process of claim 1 wherein the water-soluble polysulfhydrylated polymer defined in (d) is additionally condensed from (3) a lower alkyl amine.
References Cited 1 I l R 000E UNITED STATES PATENTS Q 2,238,672 4/1941 Arthur et al. s-12s wherein R and R" are selected from the group con- 2,933,409 4/ 1960 Binkley 6t 8 sisting of hydrogen, lower alkyl, phenyl and lower 3,148,127 9/1964 Marsh 252--305X alkoxy, R' is selected from the group consisting of 7 9 M s e et a1 167-87.1 hydrogen, OCOCH -COOCH and -CEN, Q is a radical of the formula O E N PATENTS R1 1,349,140 12/1963 France 26079 N Z)QIN O 0c 0H2 .,1q- RICHARD D. LOVERING, Primary Examiner wherein R is selected from the group consisting of US. Cl. X.R.
hydrogen and -CH R is selected from the group consisting of hydrogen and -COOH, q is an integer
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 (en) 1965-02-23 1965-02-23 New process for making permanent folds on textile articles based on keratin fibers and new products for implementing this process
FR27374A FR1502624A (en) 1965-08-05 1965-08-05 Polysulfhydryl homopolymers, preparation process and applications of these polymers

Publications (1)

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

Family

ID=26162201

Family Applications (1)

Application Number Title Priority Date Filing Date
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 (en)
DE (1) DE1619132A1 (en)
GB (1) GB1101628A (en)
NL (1) NL6602090A (en)

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 (en) * 2000-03-14 2001-09-21 Oreal BALLOIL APPLICATOR CONTAINING CAPILAR 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
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
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
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 (en) * 2001-09-26 2005-02-03 スミス　アンド　ネフュー　ピーエルシー Polymers with functions characterized by structure
CN110655609A (en) * 2019-04-30 2020-01-07 杭州肄康新材料有限公司 Textile dye fixing agent and application thereof

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 (en) * 2000-03-14 2001-09-21 Oreal BALLOIL APPLICATOR CONTAINING CAPILAR COMPOSITION
EP1138315A1 (en) * 2000-03-14 2001-10-04 L'oreal Roll-on applicator containing a hair-treating composition
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
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
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
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
JP2005503474A (en) * 2001-09-26 2005-02-03 スミス　アンド　ネフュー　ピーエルシー Polymers with functions characterized by structure
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 (en) * 2019-04-30 2020-01-07 杭州肄康新材料有限公司 Textile dye fixing agent and application thereof
CN110655609B (en) * 2019-04-30 2021-11-02 浙江新海天生物科技有限公司 Textile dye fixing agent and application thereof

Also Published As

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

Similar Documents

Publication Publication Date Title
US3576592A (en) Process for permanently pressing textile articles made of keratinic fibers
AU739160B2 (en) Hydrophilic finish for textiles
US3674688A (en) Wrinkle removing product and process
US20100035791A1 (en) Treatment composition for textile products
ES436660A1 (en) Fabric treatment compositions
US4101272A (en) Process for the treatment of wool with polyorganosiloxanes
US3597145A (en) Treatment of a cellulosic-containing textile with a fluorocarbon,an aminoplast,and a synthetic acid copolymer,and textile obtained therefrom
US3220869A (en) Process for improving textile fabrics
US2804402A (en) Treatment of cellulose containing textile materials and compositions therefor
AU602117B2 (en) Graft polymers which are water-soluble or dispersible in water, their preparation and use
TW406148B (en) Crosslinkable fabric care compositions
CA2390106A1 (en) Improving the crease recovery of fabrics
US3674418A (en) Textile spray composition
Reeves et al. Lightweight, durable-press cotton and polyester/cotton with ignition resistance
US3219478A (en) Flameproofing of cellulosic material
EP1246963B1 (en) Wrinkle removing composition and process
CN111479855A (en) Copolymers of polyalkyleneimines and polysiloxanes and compositions containing the same
US3059990A (en) Method of setting wool textiles with ethanolamine
US3100159A (en) Textile fabric processing
US2282701A (en) Process of waterproofing
US3476583A (en) Method for rendering fibrous material oil and water repellent
US3624046A (en) Polysulphydryl homopolymers, and methods of preparing and applying same
US3703351A (en) Two step modification of textile materials
US3508960A (en) Process for binding nonwoven textiles
US3232697A (en) Textile treatment