GB935756A - Monoepoxybicyclic acrylates and methacrylates and their polymers - Google Patents

Monoepoxybicyclic acrylates and methacrylates and their polymers

Info

Publication number
GB935756A
GB935756A GB3985459A GB3985459A GB935756A GB 935756 A GB935756 A GB 935756A GB 3985459 A GB3985459 A GB 3985459A GB 3985459 A GB3985459 A GB 3985459A GB 935756 A GB935756 A GB 935756A
Authority
GB
United Kingdom
Prior art keywords
emulsion
group
methyl
textile material
range
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
GB3985459A
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 GB935756A publication Critical patent/GB935756A/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

The invention comprises homopolymers, or copolymers with at least one other monoethylenically unsaturated compound, of an epoxy compound of the formula <FORM:0935756/IV(a)/1> where M represents hydrogen or one or more methyl groups which may or may not be bonded to the same cyclic carbon atom, R represents a hydrogen atom or a methyl group, n is an integer of 1 or 2, and A represents a methylene group. The comonomers include vinyl ethers, allyl ethers, acrylamides or methacrylamides, vinyl esters, allyl esters, maleates, itaconates, styrene, vinyl toluene maleic anhydride or acrylonitrile. C1-C18 alkyl acrylates or methacrylates are preferred. Terpolymers comprising acrylic or methacrylic acids, methyl methacrylate or methyl acrylate and at least one monomer of the above formula in the range of proportions 1 to 10, 98 to 80, and 1 to 10, respectively are of special interest. For polymerization at the vinyl group, a catalyst of the redox type may be used. A list of suitable oxidizing and reducing agents is given, and suitable peroxides are mentioned. Catalysts for inducing polymerization primarily through the epoxide group are specified. Polymerization through the vinyl group is conducted in the temperature range of 0 DEG to 125 DEG C. to form a linear homopolymer or copolymer which is then heated in the range 60 DEG to 180 DEG C., preferably with one or more catalysts to form a three-dimensional homopolymer or copolymer. Surfaces may be coated by applying a film of the linear polymer and then heating in the range 175 DEG to 300 DEG C. to form the cross-linked polymer. Textiles may be stabilized by impregnating them with an emulsion made by agitating a mixture of at least one epoxy monomer of the above formula and preferably one or more C1-C18 alkyl esters of acrylic, methacrylic or itaconic acid in an aqueous solution of an emulsifying agent, e.g. a cationic, anionic, or non-ionic surface active agent, at 0 DEG to 100 DEG C. in the presence of a redox catalyst until the emulsion contains 1 to 60%, preferably 15 to 35% resin solids, and then heating the impregnated textile at 110 DEG to 180 DEG C. to effect a cure. Detailed examples are given of the preparation of homopolymers, copolymers and an aqueous emulsion of a copolymer, and of the stabilization of woollen material. Specification 935,018 is referred to.ALSO:The invention comprises epoxy compounds of the formula <FORM:0935756/IV(a)/1> where M represents hydrogen or one or more methyl groups which may or may not be bonded to the same cyclic carbon atom, R represents a hydrogen atom or a methyl group n is an integer of 1 or 2, and A represents a methylene group. The novel compounds are made by epoxidising the corresponding compound with an ethylenic double bond in the 5 position on the ring using a peracid such as perbenzoic, monoperphthalic or peracetic acid. Preferably the epoxidation is carried out at a temperature in the range of 20 DEG to 50 DEG C. using 1,0 to 1,5 moles of peracid per mole of bicyclic compound. There may be present a basic agent such that when dissolved in water in a 0,1 N concentration it imparts to the solution a pH of at least 8 at 25 DEG C., e.g. sodium acetate. Polymerization inhibitors may be added, if desired. Specification 935,018 is referred to.ALSO:Textiles, e.g. wool, are shrink-proofed, softened and proofed against ultra-violet light by impregnating them with an aqueous emulsion made by agitating a mixture of at least one epoxy monomer of the formula <FORM:0935756/IV(a)/1> where M represents hydrogen or one or more methyl groups which may or may not be bonded to the same cyclic carbon atom, R represents a hydrogen atom or a methyl group, n is an integer of 1 or 2, and A represents a methylene group, and preferably one or more C1-C18 alkyl esters of acrylic, methacrylic or itaconic acid in an aqueous solution of an emulsifying agent, e.g. a cationic, anionic or non-ionic surface active agent, at 0 DEG to 100\s2. in the presence of a redox catalyst until the emulsion contains 1 to 60%, preferably 15 to 35%, resin solids, and then heating the impregnated textile at 100 DEG to 180\s2. to effect a cure. The emulsion is deposited on the textile material by such means as exhausting, spraying or dipping. Ordinarily, the textile material is padded at room temperature with an emulsion which has been adjusted to a resin content of about 1 to 20%. Drying of the emulsion-treated textile material and the heat treatment can be carried out in one step, or the textile material can be dried at a lower temperature and then heated later at the higher temperature. Preferably the textile material is in the form of a knitted or woven fabric. Specification 935,018 is referred to.
GB3985459A 1958-12-05 1959-11-24 Monoepoxybicyclic acrylates and methacrylates and their polymers Expired GB935756A (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
GB935756A true GB935756A (en) 1963-09-04

Family

ID=25112839

Family Applications (2)

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

Family Applications Before (1)

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

Country Status (3)

Country Link
BE (1) BE585307A (en)
FR (2) FR1243106A (en)
GB (2) GB935018A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440850A (en) * 1981-07-23 1984-04-03 Ciba-Geigy Corporation Photopolymerisation process with two exposures of a single layer
WO2014084297A1 (en) * 2012-11-28 2014-06-05 Jnc株式会社 Novel norbornene derivative

Families Citing this family (3)

* 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
NL292382A (en) * 1962-05-18 Laederich Ets
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.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440850A (en) * 1981-07-23 1984-04-03 Ciba-Geigy Corporation Photopolymerisation process with two exposures of a single layer
WO2014084297A1 (en) * 2012-11-28 2014-06-05 Jnc株式会社 Novel norbornene derivative

Also Published As

Publication number Publication date
FR1244610A (en) 1960-10-28
FR1243106A (en) 1960-10-07
GB935018A (en) 1963-08-28
BE585307A (en)

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