GB935018A - Aqueous dispersions of monoepoxycyclic acrylates for treating textile materials - Google Patents

Aqueous dispersions of monoepoxycyclic acrylates for treating textile materials

Info

Publication number
GB935018A
GB935018A GB3985559A GB3985559A GB935018A GB 935018 A GB935018 A GB 935018A GB 3985559 A GB3985559 A GB 3985559A GB 3985559 A GB3985559 A GB 3985559A GB 935018 A GB935018 A GB 935018A
Authority
GB
United Kingdom
Prior art keywords
methyl
vinyl
methacrylate
formula
butyl
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
Application number
GB3985559A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB935018A publication Critical patent/GB935018A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • D06M15/267—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 amino or quaternary ammonium groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Relates to an aqueous dispersion of a water-insoluble, linear polymer containing at least 3% by weight of units derived from one or more monoethylenically unsaturated monomeric cyclic epoxides of the formula <FORM:0935018/IV(a)/1> by polymerization through the terminal <FORM:0935018/IV(a)/2> group, where, in the formula, R represents hydrogen or methyl and M represents hydrogen or one or more methyl substituents which may or may not be bonded to the same carbon of the ring. The cyclic epoxide units may be derived from 1,2-, 2,3- or 3,4-epoxyhexahydrobenzyl acrylate or methacrylate, 6-methyl-3,4-, 2,3-dimethyl-1,2- or 2,3-dimethyl-2,3-hexahydrobenzyl methacrylate or 5-methyl-2,3-epoxyhexahydrobenzyl acrylate. Polymerization is preferably effected in aqueous dispersion in the presence of a non-ionic dispersing agent and a peroxide catalyst or a redox catalyst system, preferably in the presence of polymerizable monoethylenically unsaturated compounds such as vinyl ethyl, butyl, octyl, dodecyl or stearyl ether, allyl butyl, vinyl, octyl or decyl ether, methyl, ethyl, butyl, octyl or stearyl acrylate or methacrylate, methyl or butyl acrylamide or methacrylamide, vinyl acetate, butyrate or stearate, allyl butyrate, palmitate or stearate, butyl, octyl or dodecyl maleate, octyl, dodecyl or octadecyl itaconate, vinyl toluene, maleic anhydride, acrylonitrile, N-vinyl-pyrrolidone, N-vinyl-caprolactam, N-vinyl-N,N1-ethylene urea, and styrene. An example describes the copolymerization of various acrylates and methacrylates with 1,2-, 2,3- and 3,4-epoxyhexahydrobenzyl methacrylates using, as non-ionic dispersing agent, a tert.-octylphenoxypolyethoxyethanol and as catalyst a mixture of ammonium persulphate and sodium hydrosulphite. The aqueous dispersions of the invention may be used for stablizing textile materials comprising or consisting of protein fibres, particularly wool, against shrinking and felting, by impregnating the textile material with the dispersion and then curing by heating. The curing reaction may be accelerated by adding to the dispersion with which the textile is treated an acid such as formic, oxalic, sulphuric or phosphoric acid.ALSO:Cyclic epoxides of the formula <FORM:0935018/IV(a)/1> where R represents hydrogen or methyl and M represents hydrogen or one or more methyl substituents which may or may not be bonded to the same carbon of the ring, may be prepared by introducing an epoxy group into the ring of a compound represented by the formula <FORM:0935018/IV(a)/2> e.g. by treatment with perbenzoic or peracetic acid or with a mixture of hydrogen peroxide and acetic or formic acid. The preparation of 3,4-epoxyhexahydrobenzyl methacrylate from 1,2,5,6-tetrahydrobenzyl methacrylate is described. Other compounds are mentioned.ALSO:Textile materials comprising or consisting of scale-surfaced protein fibres are stabilized against shrinking and felting by treating the materials with an aqueous dispersion of a water-insoluble linear polymer containing at least 3% by weight of units derived from one or more monoethyleni cally unsaturated monomeric cyclic epoxides of the formula <FORM:0935018/IV(a)/1> by polymerization through the terminal <FORM:0935018/IV(a)/2> group, where, in the formula, R represents hydrogen or methyl and M represents hydrogen or one or more methyl substituents which may or may not be bonded to the same carbon of the ring, drying the material to deposit the dispersed polymer thereon and then heating the treated material to cure the deposited polymer. The textile materials may contain wool, silk, mohair, or synthetic fibres produced e.g., from casein or collagen, either alone or in admixture with other fibres such as cotton, linen, rayon, nylon or an acrylonitrile polymer. In a typical example pieces of flannel are treated with an aqueous dispersion of a copolymer of 3,4-epoxyhexahydrobenzyl methacrylate and n-butyl acrylate. Curing may be effected at a temperature from 212 DEG to 700 DEG F. for from five seconds to 30 minutes, the higher the temperature the shorter the period required. The curing reaction may be accelerated by adding to the dispersion with which the textile is treated an acid such as formic, oxalic, sulphuric or phosphoric acid.
GB3985559A 1958-12-05 1959-11-24 Aqueous dispersions of monoepoxycyclic acrylates for treating textile materials Expired GB935018A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US77828858A 1958-12-05 1958-12-05

Publications (1)

Publication Number Publication Date
GB935018A true GB935018A (en) 1963-08-28

Family

ID=25112839

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3985459A Expired GB935756A (en) 1958-12-05 1959-11-24 Monoepoxybicyclic acrylates and methacrylates and their polymers
GB3985559A Expired GB935018A (en) 1958-12-05 1959-11-24 Aqueous dispersions of monoepoxycyclic acrylates for treating textile materials

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3985459A Expired GB935756A (en) 1958-12-05 1959-11-24 Monoepoxybicyclic acrylates and methacrylates and their polymers

Country Status (3)

Country Link
BE (1) BE585307A (en)
FR (2) FR1243106A (en)
GB (2) GB935756A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1297575B (en) * 1960-04-15 1969-06-19 Little Inc A Process for the production of shrink-resistant wool
BE632547A (en) * 1962-05-18 Laederich Ets
US4440850A (en) * 1981-07-23 1984-04-03 Ciba-Geigy Corporation Photopolymerisation process with two exposures of a single layer
FR2664272B3 (en) * 1990-07-06 1992-11-27 Norsolor PROCESS FOR THE SELECTIVE EPOXIDATION OF UNSATURATED (METH) ACRYLATES, NEW FUNCTIONAL (METH) ACRYLATES OBTAINED AND THEIR APPLICATION TO THE SYNTHESIS OF NEW POLYMERS.
TWI614239B (en) * 2012-11-28 2018-02-11 捷恩智股份有限公司 Norbornene derivative and manufacturing method of norbornene derivative

Also Published As

Publication number Publication date
FR1244610A (en) 1960-10-28
BE585307A (en)
FR1243106A (en) 1960-10-07
GB935756A (en) 1963-09-04

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