Polyurethane compositions containing both radiation and moisture curable groups
View Patent ↗The invention provides a reaction product derived from an epoxy-functional acrylic monomer and an alkylaminoalkylene polyalkoxysilane or from a reaction product derived from acrylic acid and an epoxidized polyalkoxysilane.
1. A radiation and moisture curable composition comprising:
(a) a compound within structural formula I:
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q is S, O or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage; and
R 4 and R 5 may each independently be a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical; a is 0 or 1; and
(b) a diisocyanate.
2. The composition of claim 1 , wherein R 1 is methylene or a methylenoxy alkylene C 1-6 linkage.
3. The composition of claim 1 , further comprising a cure system.
4. The composition of claim 1 wherein the diisocyanate is an isocyanate end-capped prepolymer having the structural formula IV:
wherein R 9 and R 10 may be the same or different, and may be a divalent substituted or unsubstituted aliphatic, cycloaliphatic or aromatic radical or a polyol, polyester, or a polyalkylidene radical; Y is O or NH; and n is an integer from 1 to 100.
5. The composition of claim 4 , wherein R 10 is polymeric backbone is selected from a group consisting of polyester polyols, polyether polyols and polyhydroxy polycarbonates.
6. The composition of claim 1 , wherein R 1 is methyl, Q is oxygen, R 3 is propylene, and R 4 is methyl.
7. The composition of claim 1 , wherein R 1 is methyl, Q is NR 2 , R 2 is ethyl, R 3 is propylene and R 4 is methyl.
8. The composition of claim 4 , wherein
R 9 is a diradical formed from isophorone diisocyanate, and
R 10 is a diradical formed from hydroxy terminated polypropyleneoxide diol.
9. The composition of claim 4 , wherein R 9 is a diradical formed from isophorone diisocyanate and R 10 is a diradical formed from hydroxy terminated polypropyleneoxidepolyol.
10. The composition of claim 3 , where the curing system is selected from the group consisting of 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl1]-2-morpholino propan-1-one, 2-benzyl-2-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone, the combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone, 2,2-dimethoxy-2-phenyl acetophenone, the combination of bis(2,6-dimethoxybenzoyl-2,4,4-trimethyl pentyl) phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and [bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide], 2-hydroxy-2-methyl-1-phenyl-1-propan-1-one, the combination of 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one, dl-camphorquinone, alkyl pyruvates, 2,2-dimethoxy-2-phenyl acetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propane, bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide, bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl)phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(n 5 -2,4-cyclopentadien-1-yl)-bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl]titanium, diethoxyacetophenone and combinations thereof.
11. The composition of claim 3 , where the curing system includes a moisture curing catalyst.
12. A composition comprising the reaction product of:
(a) a compound within the structural formula I:
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q comprises S, O or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage; and
R 4 and R 5 may each independently be a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical; a is 0 or 1; and
(b) a diisocyanate.
13. The composition of claim 12 , further comprising a curing system.
14. The composition of claim 13 , where the curing system is selected from the group consisting of 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl1]-2-morpholino propan-1-one, 2-benzyl-2-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone, the combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone, 2,2-dimethoxy-2-phenyl acetophenone, the combination of bis(2,6-dimethoxybenzoyl-2,4,4-trimethyl pentyl) phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one, and [bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide], 2-hydroxy-2-methyl-1-phenyl-1-propan-1-one, the combination of 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one, dl-camphorquinone, alkyl pyruvates, 2,2-dimethoxy-2-phenyl acetophenone, 2-hydroxy-2-methyl-1-phenyl-1-propane, bis(2,4,6-trimethyl benzoyl)phenyl phosphine oxide, bis(2,6-dimethoxybenzoyl-2,4,4-trimethylpentyl)phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(n 5 -2,4-cyclopentadien-1-yl)-bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyl]titanium, diethoxyacetophenone and combinations thereof.
15. The composition of claim 13 , where the curing system comprises a moisture curing catalyst.
16. A composition comprising the reaction product of:
(i) the reaction product of an epoxidized (meth)acrylate and an alkylaminoalkylene polyalkoxysilane; and
(ii) a diisocyanate-containing compound or prepolymer.
17. A composition comprising the reaction product of:
(i) the reaction product of (meth)acrylic acid and epoxidized polyalkoxysilane; and
(ii) a diisocyanate-containing compound or prepolymer.
18. A method of producing a radiation and moisture curable composition comprising:
(a) providing a compound with the structural formula I:
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q is S, O or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage; and
R 4 and R 5 may each independently be a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical; a is 0 or 1; and
(b) reacting the compound with a diisocyanate compound.
19. The method of claim 18 , wherein in Compound I, R is H or CH 3 ;
R 1 is a methylene linkage;
Q is O;
R 3 is propylene; and
R 4 is methyl.
20. The method of claim 18 , wherein R is H or CH 3 ;
R 1 is a methylene linkage;
Q is N(R 2 );
R 2 is H;
R 3 is propylene; and
R 4 is methyl.
21. The method of claim 18 , wherein the diisocyanate compound is an end-capped prepolymer having the structural formula IV:
wherein R 9 and R 10 may be the same or different, and may be a divalent substituted or unsubstituted aliphatic, cycloaliphatic or aromatic radical or a polyol, polyester, or a polyalkylidene radical; Y is O or NH; and n is an integer from 1 to 100.
22. A method of using a composition having a reaction product of
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q is S, O or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical1;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 4 is a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical and a diisocyanante, said method comprising the steps of:
a) applying the composition onto a surface of a substrate; and
b) subjecting the composition-applied substrate to a curing mechanism to produce the reaction product.
23. A method of forming a bond comprising the steps of
a) applying a composition having the reaction product of
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q is S, or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 4 is a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical and a diisocyanate onto a surface of a substrate; and
b) subjecting said composition to conditions suitable to effectuate cure.
24. A bond comprising a cured composition, wherein said cured composition comprises the reaction product of
a)
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q is S, O or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical which may be interrupted with a heteroatom containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or, aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 4 is a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical and
b) a diisocyanate.
25. An assembly comprising:
a) a composition comprising the reaction product of
a)
where R is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
Q is S, O or N(R 2 );
R 1 comprises a divalent substituted or unsubstituted C 1-12 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 2 is H or a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical;
R 3 comprises a divalent substituted or unsubstituted C 1-20 aliphatic, cycloaliphatic or aromatic hydrocarbon radical, which may be interrupted with a heteroatom-containing linkage;
R 4 is a monovalent substituted or unsubstituted C 1-6 hydrocarbon radical, and
b) a diisocyanate, said composition being disposed between two substrates to form a mated assembly; and
c) a second substrate mated to said first substrate, thus forming an assembly.