Patent GB-935756-A (GB)
Title: Monoepoxybicyclic acrylates and methacrylates and their polymers
IPC: C08F20/32
Filed: 1959-11-24
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.