Isp Investments Inc.

Gaf Chemicals Corporation

The Ohio State University

Exxon Research and Engineering Company

Exxon Chemical Patents, Inc.

Jeffrey S Plotkin

Kolazi S Narayanan

Paul D Taylor

James A Dougherty

Fulvio J Vara

Mark M Miller

Sheldon G Shore

Robert C Michaelson

Donna G Alway

Eugene E Fehskens

Charles H McMullen

This invention relates to the polyalk-1-enyl ethers having the formula ##STR1## which is the reaction product of a hydroxylated compound and an alk-1-enyloxy oxirane and to the process for preparing the polyalk-1-enyl ether product.

Polyalk-1-enyl ethers

This invention relates to alk-1-enyl etherurethanyl block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25; A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl; R.sub.1 is alkylene containing from 1 to 6 carbon atoms; R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy; R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl; R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene and R.sub.5 is hydrogen or C.sub.1 to C.sub.4 alkyl. The invention also relates to the method of preparing and curing the above prepolymer and to the use of the cured prepolymer as a hard, flexible protective coating possessing high density and superior resistance to abrasion and chemical attack.

Radiation curable alk-1-enyl urethanyl prepolymers

This invention relates to radiation curable alk-1-enyloxy carbonate reaction products of a hydroxylated compound having the formula A-ROH and a dialk-1-enyloxy carbonate having the formula ##STR1## wherein R is a polymeric radical selected from the group of polyester, polyacetal, polyurethane, polyether, and polycarbonate, said polymers containing from about 10 to 50 repeating monomer units;

Alk-1-enyloxy carbonates

This invention relates to alkenyl ether polycarbonates having the formula ##STR1## wherein A is selected from the group consisting of lower alkyl and R'HC.dbd.CHOR--, R and R' are each independently a divalent radical having from 2 to 20 carbon atoms and are selected from the group of alkylene, mono- or poly- alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, alkyl, cyano, nitro or alkoxy; R' is hydrogen or lower alkyl; (n) has a value of from 1 to 10 and (m) has a value of from 0 to 10; with the proviso that R' contains at least 3 carbon atoms when m is zero. The invention also concerns the preparation and use of said alkenyl ether polycarbonates.

Alkenyl ether polycarbonates

This invention relates to alk-1-enyl ether-polyester block prepolymers which are curable by cationically initiated radiation and which are defined by the formula ##STR1## wherein m has a value of from 1 to 25; A is C.sub.2 to C.sub.12 alkylene, C.sub.6 to C.sub.14 aryl, both groups optionally substituted with lower alkyl, halo lower alkyl, alkyleneoxy, halogen or aryl; R.sub.1 is alkylene containing from 1 to 6 carbon atoms; R.sub.2 is a saturated or unsaturated divalent radical containing from 1 to 14 carbon atoms and is selected from the group of alkylene, alkenylene and arylene, each group optionally substituted with oxygen, halogen, lower alkyl and/or hydroxy; R.sub.3 is hydrogen or C.sub.1 to C.sub.6 alkyl; R.sub.4 is C.sub.1 to C.sub.6 alkylene, C.sub.6 to C.sub.14 arylene, lower alkyl substituted phenylene or xylylene and R.sub.5 and R.sub.6 are independently hydrogen or C.sub.1 to C.sub.4 alkyl. The invention also relates to the method of preparing and curing the above prepolymer and to the use of the cured prepolymer as a hard, flexible protective coating possessing high density and superior resistance to abrasion and chemical attack.

Radiation curable alk-1-enyl ether polyester prepolymers

This invention relates to radiation curable alk-1-enyloxy carbonate reaction products of a polyhydroxylated compound having the formula ROH and a dialk-1-enyloxy carbonate having the formula ##STR1## wherein R is a C.sub.3 to C.sub.50 saturated or unsaturated, linear, branched or cyclic polyhydroxylated hydrocarbon radical optionally substituted with halo, alkoxy, lower alkyl, cyano or nitro;

This invention relates to a coating composition which can be cured by exposure to radiation energy in the presence of a cationic photoinitiator. The composition comprises a mixture of between about 1 and about 75 wt. % of a reactive vinyl or alk-1-enyl ether cyclocarbonate having the formula ##STR1## wherein R is hydrogen or lower alkyl; R' is C.sub.2 to C.sub.4 alkylene; n has a value of from 0 to 4 and n' has a value of from 1 to 4 and between about 99 and about 25 wt. % of a polymerizable compound containing an onium salt initiator which is normally insoluble in said polymerizable compound or a mixture thereof. The invention also relates to the use of the composition as a protective coating on a substrate.

Radiation curable coating compositions

This invention relates to alkenyl ether polycarbonates having the formula ##STR1## wherein A is selected from the group consisting of lower alkyl and R'HC.dbd.CHOR--; R and R' are each independently a divalent radical having from 2 to 20 carbon atoms and are selected from the group of alkylene, mono- or poly- alkoxylated alkylene, alkenylene, alkynylene, arylene, alkarylene and aralkylene radicals, which radicals are optionally substituted with halo, alkyl, cyano, nitro or alkoxy; R' is hydrogen or lower alkyl; (n) has a value of from 1 to 10 and (m) has a value of from 0 to 10; with the proviso that R' contains at least 3 carbon atoms when m is zero. The invention also concerns the preparation and use of said alkenyl ether polycarbonates.

This invention relates to an alk-1-enyl ether having the formula ##STR1## and to the process for its preparation.

Alk-1-enyl ethers

This invention relates to the alk-1-enyl ether having the formula ##STR1##

This invention relates to the alk-1-enyl ether reaction product of a hydroxylated compound and an alk-1-enyloxy oxirane containing from 0 to 95% alkyl epoxide.

This invention relates to coating compositions containing the alk-1-enyl ether reaction product of a hydroxylated compound, an alk-1-enyloxy oxirane and from 0 to 95% of an alkyl epoxide.

Coating compositions containing alk-1-enyl ethers

The invention relates to alk-1-enyloxy carbamates selected from the group having the formulae ##STR1## wherein R is a saturated or unsaturated, monovalent or divalent hydrocarbon radical having from 1 to 50 carbon atoms and is optionally substituted with halo, alkyleneoxy, hydroxy, or a combination of said radicals; Y is --O-- or --OCO--O--; X is hydrogen or methyl; R' and R' are each independently hydrogen, alkyl, aryl, aralkyl or alkaryl; m has a value of from 2 to 6 and n has a value of from 0 to 25. The invention also relates to the use of these alk-1-enyloxy carbamates as reactive diluents in cationically induced radiation curing of epoxy, vinyl ether, urethane monomers or oligomers and others.

Alk-1-enyloxy carbamates

This invention relates to a polypropenyl ether having the formula ##STR1## wherein m and s each independently have a value of from 1 to 6; R is alkyl or phenyl optionally substituted with lower alkyl or halogen; A is C.sub.1 to C.sub.12 alkylene, aryl or --R.sub.1 OR.sub.2 --, optionally substituted with lower alkyl, haloalkyl, halogen or phenyl; one of p and p' has a value of one and the other is zero; R.sub.3 is C.sub.1 to C.sub.20 alklylene substituted with expression indicated by n and n has a value of from 1 to 10.

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Monsey, NY, United States of America

Jeffrey S Plotkin