Patent GB-1094926-A (GB)
Title: N-substituted-2-aminomethyl-3,4-dihydro-2h-pyrans and polymers thereof
Inventor: GAZZARD EDWARD GEORGE
IPC: C08F20/58
Filed: 1964-08-05
Abstract: The invention comprises homo- and copolymers of pyran derivatives of the formula <FORM:1094926/C3/1> wherein R0 and R represent hydrogen, halogen or a hydrocarbon radical, R1 represents hydrogen, a hydrocarbon radical or the group R4CO where R4 is hydrogen or a hydrocarbon radical, R2 represents hydrogen, halogen or a cyano or hydrocarbon radical R3 represents hydrogen or an alkoxy or hydrocarbon radical, "hydrocarbon" being defined as alkyl, cycloalkyl, aralkyl, aryl and alkaryl.  Polymers resulting from reaction of the acrylic moiety of the above monomers are prepared by treating the monomers, optionally in the presence of comonomers, with free radical initiators, e.g., peroxides and azo compounds. Specified comonomers are methyl acrylate and methacrylate; ethyl-, butyl-, 2-ethylhexyl- and octylacrylates, b -ethoxyethylmethacrylate, vinylchloride, vinylidene chloride, acrylonitrile, styrene, vinyltoluene, acrylamide, methacrylamide and acrylic and methacrylic acids. The resulting polymers may be cross-linked through the heterocyclic double bond using acid and Friedel-Crafts catalysts capable of polymerizing vinyl ether groups.  Cross-linking may be effected in the presence of cross-linking agents, e.g., polyhydric alcohols, polyphenols, polycarboxylic acids, polyamines, urea or melamine/formaldehyde resins or polyepoxides. A second class of polymers is obtained from the monomers by polymerization of the vinyl ether group in the pyran ring, optionally in the presence of comonomers, using known catalysts for the polymerization of vinyl ethers, e.g., strong proton-donating acids and Lewis acids. Specified comonomers are methyl-, ethyl- and butylvinyl ethers, styrene, a -methyl styrene, indene, coumarone, b -pinene, dipentene, isobutene and maleic anhydride.  The polymers can be cross-linked through the pendant acrylic groups using free-radical initiators.  The polymers are used as surface coatings which may include pigments. Examples are provided.ALSO:The invention comprises compounds of the formula <FORM:1094926/C2/1> wherein R0 and R represent hydrogen, halogen or a hydrocarbon radical, R1 represents hydrogen or a hydrocarbon radical or the group R4.CO, where R4 represents hydrogen or a hydrocarbon radical, R2 represents hydrogen, halogen, cyano or a hydrocarbon radical and R3 represents hydrogen or a hydrocarbon or alkoxy radical.  The term hydrocarbon radical is defined as designating alkyl, cycloalkyl, aralkyl, aryl or alkaryl radicals.  The compounds are made by reacting a pyran derivative of the formula <FORM:1094926/C2/2> with either (a) an ester of an acid of the formula R3CH = CR2COOH or (b) an acid halide of said acid reaction with the acid halide being effected in the presence of an acid binding agent. Numerous starting materials and products are specified. The compounds can be polymerized, alone or with a comonomer for subsequent use in coating compositions (see Divisions B2 and C3).ALSO:Coating compositions comprise homo- and co-polymers of furan derivatives of the formula <FORM:1094926/B1-B2/1> wherein R0 and R represent hydrogen, halogen, or a hydrocarbon radical, R1 represents hydrogen, a hydrocarbon radical or the group R4CO where R4 is hydrogen or a hydrocarbon radical, R2 represents hydrogen, halogen or a cyano or hydrocarbon radical, and R3 represents hydrogen or an alkoxy or hydrocarbon radical.  The polymers may be (a) those obtained by polymerisation through the acrylamide group or (b) those obtained by polymerisation through the vinyl ether group in the furan ring.  Coating compositions based on polymers (a) include cross-linking agents and/or catalysts, e.g. strong acid catalysts or Friedel Crafts catalysts; numerous polyfunctional cross-linking agents are specified.  Coating compositions based on polymers (b) include free-radical initiators to promote cross-linking.  The coating compositions may include pigments. Examples 3, 13 and 14 describe compositions used to coat tin plate.  The compositions are also stated to be useful as textile finishes.