Patent GB-892264-A (GB)
Title: Process of treating polymeric structures and product thereof
IPC: C08G18/00
Filed: 1960-08-26
Abstract: An organic polymeric structure having an active-hydrogen-containing surface is coated with a composition containing at least one organic compound having a plurality of isocyanate groups and at least one benzoyl compound having substituted therein at least one orthohydroxyl group and at least one additional active-hydrogen-containing group besides said hydroxyl group, the ratio of the number of gram equivalents of isocyanate groups in said organic compound to the number of gram equivalents of active hydrogen atoms in said additional active-hydrogen-containing group of said benzoyl compound being at least 1:20 and preferably 1:10 to 10:1, and the polymer of said structure, said isocyanate compound and said benzoyl compound are caused to inter-react, e.g. by heating to a temperature of at least 50 DEG C.  The benzoyl compound may have the formula <FORM:0892264/III/1> or <FORM:0892264/III/2> wherein Z is -NH2, -NHR, -R11OH or <FORM:0892264/III/3> ; Y1 is -OH, -NH2, -NHR -CO.NH2, -CO.NHR or -R1OH; Y is -Y1 -H, -NO2, -CO.OR, -CO.R, -R or -OR; Z1 is -Z, -R, -OR or <FORM:0892264/III/4> ; R is a pheny radical or an alkyl radical having 1 to 8 carbon atoms; R1 is a phenylene radical or an alkylene radical having 1 to 8 carbon atoms: R11 is an alkylene radical having 1 to 8 carbon atoms; n is an integer between 1 and 4 and n1 is an integer between 1 and 5.  The organic polymeric structure may not inherently have an active-hydrogen-containing surface and is treated to produce such a surface prior to coating the surface with said composition.  Such treatments include treatment with hot dilute caustic solution, concentrated sulphuric acid alone or with chromic acid or dichromates, or boron trifluoride, flame treatment, ozonization or chlorination.  The structure may take the form of a filament, fibre, rod, tube, sheet or as part of a laminate, and may be of a polyamide, e.g. polyhexamethylene adipamide (nylon), polyester, e.g. polyethylene terephthalate, polyester amide, cellulosic polymer, e.g. cellulose acetate or acetate-butyrate, polyvinyl butyral, partially hydrolysed polymers of vinyl esters, e.g. vinyl acetate, which contain active-hydrogen atoms, hydrocarbon polymers, e.g. polyethylene or polypropylene, polyacrylonitrile, or halogenated hydrocarbon polymers, e.g. polyvinyl chloride or fluoride, polyvinylidene fluoride, which are treated to produce a surface containing active hydrogen atoms.  The product of the invention an organic polymeric structure having a surface coating of a polymer having the basic structural formula <FORM:0892264/III/5> wherein P is the polymer forming said polymeric structure, Q is an alkylene or arylene radical or a group containing at least one alkylene or arylene radical; B is <FORM:0892264/III/6> <FORM:0892264/III/7> wherein Z11 is -NH-, -NR-, -R11O- or <FORM:0892264/III/8> ; Y11 is -O-, -NH-, -NR-, -CO.NH-, -CO.NR-, or -R1O-; Y is -OH, -NH2, -NHR, -CO.NH2, -CO.NHR, -R1OH, -H, -NO2, -CO.OR, -CO.R, -R or -OR; Z1 is -Z, -R, -OR, or <FORM:0892264/III/9> ; R is a phenyl radical or an alkyl radical having 1 to 8 carbon atoms; R1 is a phenylene radical or an alkylene radical having 1 to 8 carbon atoms; Z is -NH2, -NHR, -R11OH or <FORM:0892264/III/100> ; Y1 is -OH, -NH2, -NHR, -CO.NH2, -CO.NHR, or -R1OH; R11 is an alkylene radical having 1 to 8 carbon atoms; n is an integer between 1 and 4; n1 is an integer between 1 and 5; and A is <FORM:0892264/III/111> The surface coating is stated to protect the organic polymeric structure from degradation by ultra violet light.  The coated structure may be laminated to plywood using an adhesive containing for example, a polyester of ethylene glycol and dimethyl terephthalate/dimethyl sebacate, and the reaction product of 2,4 toluene diisocyanate and 2,6 toluene diisocyanate with trimethylolpropane.  Examples of the benzoyl compound (the ultra violet light absorber), organic isocyanates and organic solvents in which the coating composition may be applied, are given. Specifications 700,953 and 834,196 are referred to.ALSO:An organic polymeric structure having an active-hydrogen-containing surface is coated with a composition containing at least one organic compound having a plurality o[ isocyanate groups and at least one benzoyl compound having substituted therein at least one orthohydroxyl group and at least one additional active-hydrogen-containing group besides said hydroxyl group, the ratio of the number of gram equivalents of isocyanate groups in said organic compound to the number of gram equivalents of active hydrogen atoms in said additional active-hydrogen-containing group of said benzoyl compound being at least 1:20 and preferably 1:10 to 10:1, and the polymer of said structure, said isocyanate compound and said benzoyl compound are caused to inter-react, e.g. by heating to a temperature of at least 50 DEG C.  The benzoyl compound may have the formula <FORM:0892264/IV (a)/1> wherein Z is -NH2, -NHR, -R11OH or <FORM:0892264/IV (a)/2> ; Y1 is -OH, -NH2, -NHR, -CO.NH2, -CO.NHR or -R1OH; Y is -Y1, -H, -NO2, -CO.OR, -CO.R, -R or -OR; Z1 is -Z, -R, -OR or <FORM:0892264/IV (a)/3> ; R is a phenyl radical or an alkyl radical having 1 to 8 carbon atoms; R1 is a phenylene radical or an alkylene radical having 1 to 8 carbon atoms; R11 is an alkylene radical having 1 to 8 carbon atoms; n is an integer between 1 and 4 and n1 is an integer between 1 and 5.  The organic polymeric structure may not inherently have an active-hydrogen-containing surface and is treated to produce such a surface prior to coating the surface with said composition.  Such treatments include treatment with hot dilute caustic solution, concentrated sulphuric acid alone or with chromic acid or dichromates, or boron trifluoride, flame treatment, ozonization or chlorination.  The structure may take the form of a filament, fibre, rod, tube, sheet or as part of a laminate, and may be of a polyamide, e.g. polyhexamethylene adipamide (nylon), polyester, e.g. polyethylene terephthalate, polyester amide, cellulosic polymer, e.g. cellulose acetate or acetate-butyrate, polyvinyl butyral, partially hydrolysed polymers of vinyl esters, e.g. vinyl acetate, which contain active-hydrogen atoms, hydrocarbon polymers, e.g. polyethylene or polypropylene, polyacrylonitrile, or halogenated hydrocarbon polymers, e.g. polyvinyl chloride or fluoride, polyvinylidene fluoride, which are treated to produce a surface containing active-hydrogen atoms.  The product of the invention is an organic polymeric structure having a surface coating of a polymer having the basic structural formula <FORM:0892264/IV (a)/4> wherein P is the polymer forming said polymeric structure, Q is an alkylene or arylene radical or a group containing at least one alkylene or arylene radical; B is <FORM:0892264/IV (a)/5> wherein Z11 is -NH-, -NR-, -R11O- or <FORM:0892264/IV (a)/6> ; Y11 is -O-, -NH-, -NR-, -CO.NH-, -CO.NR-, or -R1O-; Y is -OH, -NH2, -NHR, -CO.NH2, -CO.NHR, -R1OH, -H, -NO2, -CO.OR, -CO.R, -R or -OR; Z1 is -Z, -R, -OR, or <FORM:0892264/IV (a)/7> ; R is a phenyl radical or an alkyl radical having 1 to 8 carbon atoms; R1 is a phenylene radical or an alkylene radical having 1 to 8 carbon atoms; Z is -NH2, -HNR, -R11OH or <FORM:0892264/IV (a)/8> ; Y1 is -OH, -NH2, -NHR, -CO.NH2, -CO.NHR, or -R1OH; R11 is an alkylene radical having 1 to 8 carbon atoms; p is an integer between 1 and 4; n1 is an integer between 1 and 5; and A is -O- or -N-.  The surface coating is stated to protect the organic polymeric structure from degradation by ultra-violet light.  The coated structure may be laminated to plywood using an adhesive containing for example, a polyester of ethylene glycol and dimethyl terephthalate/dimethyl sebacate, and the reaction product of 2,4 toluene diisocyanate and 2,6 toluene diisocyanate with trimethylolpropane.  Examples of the benzoyl compound (the ultra-violet light absorber), organicisocyanates and organic solvents in which the coating composition may be applied, are given. Specifications 700,953 and 834,196 are referred to.ALSO:An organic polymeric structure having an active-hydrogen-containing surface is coated with a composition containing at least one organic compound having a plurality of isocyanate groups and at least one benzoyl compound having substituted therein at least one orthohydroxyl group and at least one additional active-hydrogen-containing group besides said hydroxyl group, the ratio of the number of gram equivalents of isocyanate groups in said organic compound to the number of gram equivalents of active hydrogen atoms in said additional active-hydrogen-containing group of said benzoyl compound being at least 1 : 20 and preferably 1 : 10 to 10 : 1, and the polymer of said structure, said isocyanate compound and said benzoyl compound are caused to inter-react, e.g. by heating to a temperature of at least 50 DEG C.  The benzoyl compound may have the formula <FORM:0892264/IV (c)/1> wherein Z is -NH2, -NHR, -R11OH or <FORM:0892264/IV (c)/2> Y1 is -OH, -NH2, -NHR, -CO.NH2, -CO.NHR or -R1OH; Y is -Y1, -H -NO2, -CO.OR, -CO.R, -R or -OR; Z1 is -Z, -R, -OR or <FORM:0892264/IV (c)/3> R is a phenyl radical or an alkyl radical having 1 to 8 carbon atoms; R1 is a phenylene radical or an alkylene radical having 1 to 8 carbon atoms; R11 is an alkylene radical having 1 to 8 carbon atoms; n is an integer between 1 and 4 and n1 is an integer between 1 and 5. The organic polymeric structure may not inherently have an active-hydrogen-containing surface and is treated to produce such a surface prior to coating the surface with said composition.  Such treatments include treatment with hot dilute caustic solution, concentrated sulphuric acid alone or with chromic acid or dichromates, or boron trifluoride, flame treatment, ozonization or chlorination.  The structure may take the form of a filament or fibre and may be of a polyamide, e.g. polyhexamethylene adipam