Chloral copolymers

Claim 2

An addition copolymer of chloral and at least one comonomer selected from the group consisting of R.sup.3 --N=C=X and X=C=N--R.sup.4 --N=C=X wherein

Claim 3

X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of nonsubstituted alkyl and cylcoalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, substitution being selected from the group consisting of nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU11## in which Y is lower alkyl or phenyl; and R 4 is selected from the group consisting of nonsubstituted and substituted alkylene, alkarylene, aralkylene, cycloalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being selected from the group consisting of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU12## in which Y is lower alkyl or phenyl, the copolymer containing from 1 to 99.9 mole percent of chloral.

Claim 4

X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of nonsubstituted alkyl and cylcoalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, substitution being selected from the group consisting of nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU11## in which Y is lower alkyl or phenyl; and R 4 is selected from the group consisting of nonsubstituted and substituted alkylene, alkarylene, aralkylene, cycloalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being selected from the group consisting of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU12## in which Y is lower alkyl or phenyl, the copolymer containing from 1 to 99.9 mole percent of chloral.

Claim 5

A copolymer of claim 1 in which the comonomer is an isocyanate.

Claim 6

A copolymer of claim 1 in which the comonomer is a diisocyanate.

Claim 7

A copolymer of claim 1 in which the comonomer is an isothiocyanate,

Claim 8

A copolymer of claim 1 in which the comonomer is a diisothiocyanate.

Claim 9

A copolymer of claim 1 in the form of an article of manufacture.

Claim 10

A copolymer of claim 1 in the form of a film.

Claim 11

A copolymer of claim 1 in the form of a foam.

Claim 12

A copolymer of claim 1 in the form of a fiber.

Claim 13

A copolymer of claim 1 in the form of a sheet.

Claim 14

A copolymer of claim 1 in the form of pipe.

Claim 15

A copolymer of claim 1 containing an inorganic filler.

Claim 16

A copolymer of claim 12 in which the filler is fiber glass.

Claim 17

A copolymer of claim 1 stabilized against weight loss from heat.

Claim 18

A copolymer of claim 1 containing from about 50 to 99.9 mol percent of chloral.

Claim 19

A copolymer of claim 1 containing from about 80 to 99.9 mol percent of chloral.

Claim 20

A copolymer of claim 16 wherein the comonomer is hexamethylene diisocyanate.

Claim 21

A copolymer of claim 16 wherein the comonomer is toluene diisocyanate.

Claim 22

A copolymer of claim 16 wherein the comonomer is p,p'diisocyanatodiphenylmethane.

Claim 23

A copolymer of claim 16 wherein the monomers are chloral, butyl isocyanate, phenyl isocyanate and 2,4-diisocyanatotoluene.

Claim 24

The cryotachensic polymerization process of making a copolymer of chloral and at least one comonomer selected from the group consisting of R.sup.3 --N=C=X and X=C=N--R.sup.4 --N=C=X wherein X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of substituted alkyl and cycloalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, substitution being selected from the group consisting of nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU13## in which Y is lower alkyl and phenyl; and R 4 is selected from the group consisting of nonsubstituted and substituted alkylene, alkarylene, aralkylene, cycloalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being selected from the group consisting of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU14## in which Y is lower alkyl or phenyl, comprising forming, at a temperature above its threshold polymerization temperature, a quiescent homogeneous mixture of the monomers and an effective amount of an anionic polymerization initiator, cooling the quiescent mixture below its threshold polymerization temperature to effect polymerization of the monomers, and maintaining the mixture quiescent during the polymerization process.

Claim 25

The cryotachensic polymerization process of making a copolymer of chloral and at least one comonomer selected from the group consisting of R.sup.3 --N=C=X and X=C=N--R.sup.4 --N=C=X wherein X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of substituted alkyl and cycloalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, substitution being selected from the group consisting of nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU13## in which Y is lower alkyl and phenyl; and R 4 is selected from the group consisting of nonsubstituted and substituted alkylene, alkarylene, aralkylene, cycloalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being selected from the group consisting of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU14## in which Y is lower alkyl or phenyl, comprising forming, at a temperature above its threshold polymerization temperature, a quiescent homogeneous mixture of the monomers and an effective amount of an anionic polymerization initiator, cooling the quiescent mixture below its threshold polymerization temperature to effect polymerization of the monomers, and maintaining the mixture quiescent during the polymerization process.

Claim 26

The process of claim 21 in which a comonomer is an isocyanate.

Claim 27

The process of claim 21 in which the comonomers are butyl isocyanate, phenyl isocyanate and 2,4-diisocyanatotoluene.

Claim 28

The process of claim 21 carried out in the presence of an aprotic solvent which is inert to the monomers and initiator and is liquid at the polymerization temperature.

Claim 29

The process of claim 21 wherein the aprotic solvent is a hydrocarbon.

Claim 30

The process of claim 21 wherein the aprotic solvent is halogenated hydrocarbon.

Claim 31

The process of claim 21 wherein the process is carried out in a mold to produce a shaped copolymer.

Claim 32

The cryotachensic polymerization process of making a copolymer of chloral and at least one comonomer selected from the group consisting of R 3 --N=C=X and X=C=N--R 4 --N=C=X wherein X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of substituted alkyl and cycloalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, substitution being selected from the group consisting of nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU15## in which Y is lower alkyl and phenyl; and R 4 is selected from the group consisting of nonsubstituted and substitsuted alkylene, alkarylene, aralkylene, cylcoalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being selected from the group consisting of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU16## in which Y is lower alkyl or phenyl, comprising forming, at a temperature above its threshold polymerization temperature, a quiescent homogeneous mixture of chloral and an effective amount of anionic polymerization initiator, cooling the quiescent mixture below its threshold polymerization temperature to effect homopolymerization of part of the chloral under quiescent conditions, and then adding the at least one comonomer as set out above and causing it to copolymerize with at least the remaining free chloral.

Claim 33

The cryotachensic polymerization process of making a copolymer of chloral and at least one comonomer selected from the group consisting of R 3 --N=C=X and X=C=N--R 4 --N=C=X wherein X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of substituted alkyl and cycloalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, substitution being selected from the group consisting of nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU15## in which Y is lower alkyl and phenyl; and R 4 is selected from the group consisting of nonsubstituted and substitsuted alkylene, alkarylene, aralkylene, cylcoalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being selected from the group consisting of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU16## in which Y is lower alkyl or phenyl, comprising forming, at a temperature above its threshold polymerization temperature, a quiescent homogeneous mixture of chloral and an effective amount of anionic polymerization initiator, cooling the quiescent mixture below its threshold polymerization temperature to effect homopolymerization of part of the chloral under quiescent conditions, and then adding the at least one comonomer as set out above and causing it to copolymerize with at least the remaining free chloral.

Claim 34

The process of claim 28 in which about 60 percent of the original quantity of chloral or polymerized to homopolymer under quiescent conditions.

Claim 35

An unpolymerized liquid mixture of chloral and at least one compound selected from the group consisting of R.sup.3 --N=C=X, and X=C=N--R.sup.4 --N=C=X, wherein X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of substituted alkyl and cycloalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, nitro, cyano, phenylazo, --NY 2 , --OY, --SY, ##EQU17## in which Y is lower alkyl or phenyl; and R 4 is selected from the group consisting of nonsubstituted and substituted alkylene, alkarylene, aralkylene, cycloalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU18## in which Y is lower alkyl or phenyl; said unpolymerized mixture containing from 1 to 99.9 mol percent of chloral.

Claim 36

An unpolymerized liquid mixture of chloral and at least one compound selected from the group consisting of R.sup.3 --N=C=X, and X=C=N--R.sup.4 --N=C=X, wherein X is selected from the group consisting of oxygen and sulfur; R 3 is selected from the group consisting of substituted alkyl and cycloalkyl of up to 18 carbons, aryl of 6-18 carbons, and alkaryl and aralkyl of 7-24 carbons, nitro, cyano, phenylazo, --NY 2 , --OY, --SY, ##EQU17## in which Y is lower alkyl or phenyl; and R 4 is selected from the group consisting of nonsubstituted and substituted alkylene, alkarylene, aralkylene, cycloalkylene, alkylenebis(cycloalkylene), alkylenebis(arylene), arylene, arylenebis(alkylene) of up to 18 carbons and anthraquinonylene, any substitution being of fluorine, chlorine, bromine, iodine, nitro, cyano, phenylazo, and --NY 2 , --OY, --SY, ##EQU18## in which Y is lower alkyl or phenyl; said unpolymerized mixture containing from 1 to 99.9 mol percent of chloral.

Claim 37

A liquid mixture of claim 30 containing from about 50 to 99.9 mol percent of chloral.