Cationically curable polyurethane compositions having vinyl ether functionality

Claim 2

A cationically curable polyurethane composition comprising the reaction product of an organic polyisocyanate with a transvinylation polyhydric alcohol mixture containing hydroxy groups that is the transvinylation reaction product of (1) at least one vinyl ether and (2) at least one polyhydric alcohol having an average of more than 2 hydroxy groups per molecule, with the polyisocyanate consuming substantially all of the available hydroxy groups of the transvinylation mixture.

Claim 3

The composition in accordance with claim 1 wherein the polyhydric alcohol contains at least about 3 to about 90 percent by weight of unreacted polyhydric alcohol.

Claim 4

The composition in accordance with claim 1 wherein the polyhydric alcohol is transvinylated to react from 30 to 80 percent of the hydroxy groups thereon.

Claim 5

The composition in accordance with claim 1 wherein the polyisocyanate is a diisocyanate and the polyurethane has a vinyl ether functionality in excess of 2.1.

Claim 6

The composition in accordance with claim 2 wherein the diisocyanate is a bisphenylalkane diisocyanate in which the alkane group contains 1 to 8 carbon atoms.

Claim 7

The composition in accordance with claim 1 wherein the polyhydric alcohol has an average of 3 or more hydroxy groups per molecule.

Claim 8

The composition in accordance with claim 6 wherein the polyhydric alcohol has up to an average of about 10 hydroxy groups per molecule.

Claim 9

The composition in accordance with claim 1 wherein the polyhydric alcohol contains 2 to about 10 carbon atoms.

Claim 10

The composition in accordance with claim 1 wherein the polyhydric alcohol contains 3 to about 6 carbon atoms.

Claim 11

The composition in accordance to claim 1 wherein the vinyl ether has the formula: ##STR2## wherein R a , R b , R c , R d , and R e are each independently selected from the group of hydrogen and lower alkyl containing 1 to 4 carbon atoms and R a or R b and R c can be joined together to form part of a ring structure, R a or R b and R d or R e can be joined together to form part of a ring structure and R c and R d or R e can be joined together to form part of a ring structure, R f is an aromatic or aliphatic group that is only reactive at the site(s) where a vinyl ether containing radical is bound, x is equal to 0 or 1 and n is equal to 1 to 10 with the proviso that n is less than or equal to the number of reactive sites of R f .

Claim 12

The composition in accordance with claim 10 wherein R f contains 1 to about 20 atoms, contains at least one carbon atom, and can contain heteroatoms and n is equal to 1 to 4.

Claim 13

The composition in accordance with claim 11 wherein R f contains 1 to about 10 atoms.

Claim 14

The composition in accordance with claim 10 wherein R f is a straight or branched carbon containing group containing 1 to about 8 atoms and can contain at least one oxygen atom and n is 1 to about 4.

Claim 15

The composition in accordance with claim 13 wherein R f contains 1 to about 4 atoms.

Claim 16

The composition in accordance with claim 1 wherein the vinyl ether has the formula: (CH.sub.2═CH--O--CH.sub.2).sub.n R.sup.g wherein R g is an aliphatic group that is only reactive at the site(s) where a vinyl ether containing radical is bound and n is equal to 1 to 4 with the proviso that n is less than or equal to the number of reactive sites of R g .

Claim 17

The composition in accordance with claim 1 wherein the transvinylated mixture contains 3 to 25 weight percent of unreacted polyhydric alcohol, 30 to 94 weight percent of partially transvinylated alcohol and 3 to 25 weight percent of fully transvinylated alcohol.

Claim 18

The composition in accordance with claim 1 wherein the equivalent ratio of vinyl ether to polyhydric alcohol for the transvinylation reaction is in the range of about 0.5:1 to about 5:1.

Claim 19

The composition in accordance with claim 17 wherein the equivalent ratio is about 0.8:1 to about 2:1.

Claim 20

The composition in accordance with claim 1 can further include amine functionality and wherein the equivalent ratio of hydroxy, and/or amine functionality to isocyanate is up to about 1.2:1.

Claim 21

The composition in accordance with claim 1 wherein the transvinylation mixture is produced by subjecting an admixture of vinyl ether and polyhydric alcohol to ultrasonic energy for a time period effective to produce the transvinylation mixture.

Claim 22

A cationically curable polyurethane composition comprising the reaction product of an organic diisocyanate with a transvinylation polyhydric alcohol mixture containing hydroxy groups that is the transvinylation reaction product of (1) a vinyl ether having the formula: (CH.sub.2 ═CH--O--CH.sub.2).sub.n R.sup.g wherein R g is an aliphatic group that is only reactive at the site(s) where a vinyl ether containing radical is bound and n is equal to 1 to 4 with the proviso that n is less than or equal to the number of reactive sites of R g and (2) at least one aliphatic polyhydric alcohol containing 2 to about 10 carbon atoms and having an average of 3 or more hydroxy groups per molecule, wherein the diisocyanate consumes substantially all of the available hydroxy groups of the transvinylation mixture and the equivalent ratio of vinyl ether to polyhydric alcohol is in the range of about 0.5:1 to about 5:1.

Claim 23

A cationically curable polyurethane composition comprising the reaction product of an organic diisocyanate with a transvinylation polyhydric alcohol mixture containing hydroxy groups that is the transvinylation reaction product of (1) a vinyl ether having the formula: (CH.sub.2 ═CH--O--CH.sub.2).sub.n R.sup.g wherein R g is an aliphatic group that is only reactive at the site(s) where a vinyl ether containing radical is bound and n is equal to 1 to 4 with the proviso that n is less than or equal to the number of reactive sites of R g and (2) at least one aliphatic polyhydric alcohol containing 2 to about 10 carbon atoms and having an average of 3 or more hydroxy groups per molecule, wherein the diisocyanate consumes substantially all of the available hydroxy groups of the transvinylation mixture and the equivalent ratio of vinyl ether to polyhydric alcohol is in the range of about 0.5:1 to about 5:1.

Claim 24

The composition in accordance with claim 21 wherein the polyurethane has an average vinyl ether functionality in excess of 2 groups per polyurethane molecule.

Claim 25

The composition in accordance with claim 21 wherein the polyhydric alcohol contains 3 to about 6 carbon atoms.

Claim 26

The composition in accordance with claim 21 wherein R g contains 1 to about 4 atoms.

Claim 27

The composition in accordance with claim 21 wherein the equivalent ratio is about 0.8:1 to about 2:1.

Claim 28

The composition in accordance with claim 21 wherein the transvinylated mixture contains 3 to 25 weight percent of unreacted polyhydric alcohol, 30 to 94 weight percent of partially transvinylated alcohol and 3 to 25 weight percent of fully transvinylated alcohol.

Claim 31

The method in accordance to claim 27 wherein the ultrasonic energy has a frequency of about 10 to about 850 kHz.

Claim 32

The method in accordance with claim 27 wherein the transvinylated mixture contains 3 to 25 weight percent of unreacted polyhydric alcohol, 30 to 94 weight percent of partially transvinylated alcohol and 3 to 25 weight percent of fully transvinylated alcohol.

Claim 33

The method in accordance with claim 27 wherein the equivalent ratio of vinyl ether to polyhydric alcohol for the transvinylation reaction is in the range of about 0.5:1 to about 5:1.

Claim 34

The method in accordance with claim 30 wherein the equivalent ratio is about 0.8:1 to about 2:1.

Claim 35

The method in accordance with claim 27 wherein the equivalent ratio of hydroxy, and/or amine functionality, to isocyanate is up to about 1.2:1.

Claim 38

The method in accordance to claim 33 wherein the ultrasonic energy has a frequency of about 10 to about 850 kHz.

Claim 39

The method in accordance with claim 33 wherein the transvinylated mixture contains 3 to 25 weight percent of unreacted polyhydric alcohol, 30 to 94 weight percent of partially transvinylated alcohol and 3 to 25 weight percent of fully transvinylated alcohol.

Claim 40

The method in accordance with claim 33 wherein the equivalent ratio of vinyl ether to polyhydric alcohol for the transvinylation reaction is in the range of about 0.5:1 to about 5:1.

Claim 41

The method in accordance with claim 36 wherein the equivalent ratio is about 0.8:1 to about 2:1.

Claim 42

The method in accordance with claim 33 wherein the equivalent ratio of hydroxy, and/or amine functionality, to isocyanate is up to about 1.2:1.