Thermosetting coatings based on ketoxime-blocked isocyanates and oxazolidines

Claim 2

A low temperature curing, one-component thermosetting coating composition comprising an oxime-blocked polyisocyanate and an oxazolidine, said oxazolidine being hydrolyzable by moisture at a temperature of between about 125° F. and 325° F. the hydrolysis product of which can react with a polyisocyanate, to produce a polymeric product.

Claim 3

A composition according to claim 1 wherein the oxazolidine has the formula ##STR13## wherein R 1 is a hydrogen atom, a phenyl group, a benzyl group, or a (C 1 - C 12 )alkyl group, and R 2 is a hydrogen atom or a (C 1 - C 4 ) alkyl group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five- or six-membered saturated carbon ring, and Y is the radical ##STR14## ps wherein n is 2 or 3, and R 3 and R 4 are, individually, hydrogen atoms, (C 1 - C 12 ) alkyl groups, (C 6 - C 10 ) aryl groups, or (C 7 - C 12 ) aralkyl or alkaryl groups, R 8 is a saturated or unsaturated alkyl or polyvalent alkylene radical having up to 38 carbon atoms, and aralkyl, alkaryl, polyvalent aralkylene, or polyvalent alkarylene radical having up to 25 cabon atoms, or an aryl or polyvalent arylene radical having up to 18 carbon atoms, and z is an integer equal to the valence of R 8 .

Claim 4

A composition according to claim 1 wherein the oxazolidine has the formula ##STR15## wherein R 1 is a hydrogen atom, a phenyl group, a benzyl group, or a (C 1 - C 12 ) alkyl group, and R 2 is a hydrogen atom or a (C 1 - C 4 ) alkyl group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five-or six-membered saturated carbon ring, and Y is the radical ##STR16## wherein n is 2 or 3, and R 3 and R 4 are individually, hydrogen atoms. (C 1 - C 12 ) alkyl groups, (C 6 - C 10 ) aryl groups, or (C 7 - C 12 ) aralkyl or alkaryl groups, Z is a divalent alkylene, a tri- or tetravalent hydrocarbon radical, or a monovalent (C 1 - C 18 ) alkyl group, a (C 3 - C 18 ) alkyl group, a (C 3 - C 14 ) cycloalkyl group, a (C 6 - C 14 ) aryl group, or a (C 7 - C 12 ) aryl group, or a (C 7 - C 15 ) aralkyl or alkaryl group, X is the radical ##STR17## wherein q is an integer of 2 to 4, and R 5 and R 6 are individually selected from hydrogen or unsubstituted or substituted (C 1 - C 6 ) alkyl groups, and m is an integer of one to four, and is equal to the valence of Z.

Claim 5

A composition according to claim 1 wherein the oxazolidine has the formula ##STR18## wherein R 1 is a hydrogen atom, a phenyl group, a benzyl group, or a (C 1 - C 12 ) alkyl group, and R 2 is a hydrogen atom or a (C 1 - C 4 ) alkyl group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five or six-membered saturated carbon ring, and Y is the radical ##STR19## wherein n is 2 or 3, and R 3 and R 4 are, individually, hydrogen atoms, (C 1 - C 12 ) alkyl groups, (C 6 - C 10 ) aryl group, or (C 7 - C 12 ) aralkyl or alkaryl groups. X is the radical ##STR20## wherein q is an integer of 2 to 4, and R 5 and R 6 are, individually, hydrogen or unsubstituted or substituted (C 1 - C 6 ) alkyl groups, Z' is a saturated, polyvalent alkylene radical having up to 38 carbon atoms, a polyvalent phenylene group, a polyvalent halo-substituted phenylene group, a (C 1 - C 8 ) alkyl-substituted phenylene group, the divalent hydrocarbon residue of 1,1,3-trimethyl-5-carboxyl-3-(p-carboxyphenyl)indane, an unsaturated divalent alkenyl radical having 2 to 3 carbon atoms, or a O=C<group, A is ##STR21## (the left valence being connected to the Z' radical) or --O--, when Z' is O=C<, and m' is an integer of at least two, and is equal to the valence of Z'.

Claim 6

A composition according to claim 1 wherein the oxazolidine is a polymer of an unsaturated oxazolidine of the formula ##STR22## wherein R 1 is a hydrogen atom, a phenyl group, a benzyl group, or a (C 1 - C 12 ) alkyl group, and R 2 is a hydrogen atom or a (C 1 - C 4 ) alkyl group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five- of six-membered saturated carbon ring, and Y is the radical ##STR23## whrein n is 2 or 3, and R 3 and R 4 are, individually, hydrogen atoms, (C 1 - C 12 ) alkyl groups, (C 6 - C 10 ) aryl groups, or (C 7 - C 12 ) aralkyl or alkaryl groups, n' is 1 or 2, and n" is 2 or 3.

Claim 7

A composition according to claim 1 wherein the oxazolidine has at least one substituent of the formula ##STR24## wherein R 1 is a hydrogen atom, a phenyl group, a benzyl group, or a (C 1 - C 12 ) alkyl group, and R 2 is a hydrogen atom or a (C 1 - C 4 ) alkyl group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five- or six-membered saturated carbon ring, and Y is the radical ##STR25## wherein n is 2 or 3, and R 3 and R 4 are, individually, hydrogen atoms, (C 1 - C 12 ) alkyl groups, (C 6 - C 10 ) aryl groups, or (C 7 - C 12 ) aralkyl or alkaryl groups.

Claim 8

Composition according to claim 6 wherein n is 2, R 3 is a hydrogen atom, and R 4 is a hydrogen atom.

Claim 9

A composition according to claim 7 wherein the ratio of molar equivalents of ketoxime-blocked polyisocyanate to oxazolidine is about 1:10 to 2.5:1.

Claim 10

A composition according to claim 8 wherein the ratio is about 1:1.1 to 2.5:1. 45

Claim 11

A process for forming a polymeric material which comprises contacting with water a composition comprising a ketoxime-blocked polyisocyanate and an oxazolidine having at least one substitutent of the formula: ##STR26## wherein R 1 is a hydrogen atom, a phenyl group, benzyl group, or a (C 1 -C 12 ) alkyl group, and R 2 is a hydrogen atom or a (C 1 -C 4 ) group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five- or six-membered saturated carbon ring, and Y is the radical ##STR27## wherein n is 2 or 3, and R 3 and R 4 are, individually, hydrogen atoms, (C 1 -C 12 ) alkyl groups, (C 6 -C 10 ) aryl groups, or (C 7 -C 12 ) aralkyl or alkaryl groups, and heating the composition, in the presence of said water, to a temperature at which the isocyanate is unblocked and said polymeric material is formed.

Claim 12

A process for forming a polymeric material which comprises contacting with water a composition comprising a ketoxime-blocked polyisocyanate and an oxazolidine having at least one substitutent of the formula: ##STR26## wherein R 1 is a hydrogen atom, a phenyl group, benzyl group, or a (C 1 -C 12 ) alkyl group, and R 2 is a hydrogen atom or a (C 1 -C 4 ) group, or R 1 and R 2 are taken together with the attached carbon atom to form a saturated five- or six-membered saturated carbon ring, and Y is the radical ##STR27## wherein n is 2 or 3, and R 3 and R 4 are, individually, hydrogen atoms, (C 1 -C 12 ) alkyl groups, (C 6 -C 10 ) aryl groups, or (C 7 -C 12 ) aralkyl or alkaryl groups, and heating the composition, in the presence of said water, to a temperature at which the isocyanate is unblocked and said polymeric material is formed.

Claim 13

A coating composition according to claim 1 wherein the ketoxime-blocked polyisocyanate is a 2-butanone oxime-blocked isocyanate.

Claim 14

A coating composition according to claim 5 wherein the ketoxime-blocked polyisocyanate is 2-butanone oxime-blocked 2-isocyanatoethyl-6-isocyanatocaproate.

Claim 15

A coating composition according to claim 1 which also comprises an organosoluble zinc salt.

Claim 16

A coating composition according to claim 7 wherein the zinc salt is zinc octoate.

Claim 17

The process of claim 10 in which the material is applied to a substrate prior to heating the composition.

Claim 18

The process of claim 15 in which the substrate is wood, metal, plastic, paper of leather.

Claim 19

A process of claim 16 in which the substrate if plastic, and the temperature is between about 125° F. and 325° F.

Claim 20

The process of claim 17 in which the material is heated to a temperature between about 225° and 300° F.