Oxirane (ethylene oxide) polyurethane coatings
View Patent ↗The present invention relates to hydrophilic, i.e., water loving coatings (hereafter referred to as “WLC”). Polyurethane epoxy alkylene oxide coatings usable as coatings on for example, medical devices are a preferred WLC.
1. An epoxy urethane alkylene oxide coating comprising a reaction product of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment; and
e) glycidol.
2. The coating of claim 1 , wherein the reaction product further comprises glycidyl moieties as a reacted product of the glycidol.
3. The coating of claim 1 , wherein the poly[di(ethylene glycol) adipate] segment has a number average molecular weight in the range of about 400 to about 10,000.
4. The coating of claim 1 , wherein the reactants further comprise dimethylol propionic acid.
5. The coating of claim 4 , wherein the reaction product further comprises:
a) acid moieties that result from the dimethylol propionic acid;
b) glycidyl moieties as a reacted product of the glycidol; and
c) wherein the diisocyanate is 4,4′-methylene diphenyl diisocyanate.
6. The coating of claim 5 , wherein the reaction product further comprises an amide moiety as the reacted product of excess 4,4′-methylene diphenyl diisocyanate and the dimethylol propionic acid.
7. The coating of claim 6 , wherein the reaction product further comprises urea moieties.
8. The coating of claim 4 , wherein the reactants further comprise adipic acid dihydrazide.
9. The coating of claim 4 , wherein the reactants further comprise water.
10. The coating of claim 9 , wherein the reaction product further comprises:
a) acid moieties that result from the dimethylol propionic acid;
b) glycidyl moieties as a reacted product of the glycidol; and
c) urea moieties that result from reaction of the diisocyanate and adipic acid dihydrazide.
11. The coating of claim 9 , wherein the reaction product further comprises:
a) acid moieties that result from the dimethylol propionic acid;
b) glycidyl moieties as a reacted product of the glycidol; and
c) wherein the diisocyanate is 4,4′-methylene diphenyl diisocynate.
12. The coating of claim 11 , wherein the reaction product further comprises urea moieties that result from reaction of the diisocyanate and water.
13. An epoxy urethane alkylene oxide coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment; and
e) glycidol.
14. The coating of claim 13 , wherein the poly[di(ethylene glycol) adipate] segment has an number average molecular weight in the range of about 400 to about 10,000.
15. An epoxy urethane ester carboxylic acid alkylene oxide coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment;
e) dimethylol propionic acid; and
f) glycidol.
16. An epoxy urethane urea carboxylic acid alkylene oxide coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphtalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment;
e) dimethylol propionic acid;
f) adipic acid dihydrazide; and
g) glycidol.
17. A terminal oxirane polyurethane urea chain extender/water excess coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment;
e) dimethylol propionic acid;
f) water; and
g) glycidol.
18. An epoxy urethane alkylene oxide coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment;
e) glycidol, and
f) glycidyl moieties as a reacted product of the glycidol.
19. An epoxy urethane ester carboxylic acid alkylene oxide coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1, 4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment;
e) dimethylol propionic acid; and
f) glycidol,
g) wherein the reaction product further includes:
i) acid moeities that result from the dimethylol propionic acid;
ii) urea moieties; and
iii) glycidyl moieties as a reacted product of the glycidol.
20. An epoxy urethane urea carboxylic acid alkylene oxide coating comprising a reaction product consisting essentially of the following reactants:
a) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment;
e) dimethylol propionic acid;
f) adipic acid dihydrazide; and
g) glycidol,
h) wherein the reaction product further includes:
i) acid moeities that result from the dimethylol propionic acid;
ii) urea moieties; and
iii) glycidyl moieties as a reacted product of the glycidol.
21. A terminal oxirane polyurethane urea chain extender/water excess coating comprising a reaction product consisting essentially of the following reactants:
a) water;
b) a diisocyanate selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
c) a poly(ethylene oxide) segment having a number average molecular weight in the range of about 18,000 to about 2,000,000;
d) a poly[di(ethylene glycol) adipate] segment;
e) a poly(tetrahydrofuran) segment;
f) dimethylol propionic acid;
g) glycidol,
h) wherein the reaction product further includes:
i) acid moeities that result from the dimethylol propionic acid;
ii) urea moieties; and
iii) glycidyl moieties as a reacted product of the glycidol.
22. An epoxy urethane alkylene oxide coating comprising a reaction product of the following reactants:
a) a diisocyanate from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 3,3′-dimethyl-4,4′-biphenyl diisocyanate, 4,4′-methylene diphenyl diisocyanate, polymeric MDI, naphthalene diisocyanate, 4,4′-diisocyanatodicyclohexylmethane, 1,4-benzene diisocyanate, trans-cyclohexane-1,4-diisocyanate, 1,5-naphthalene diisocyanate, 1,6-hexamethylene diisocyanate, 4,6-xylene diisocyanate, and isophorone diisocyanate, with combinations and isomers thereof;
b) a dimethylol propionic acid;
c) a poly[di(ethylene glycol) adipate] segment;
d) a poly(tetrahydrofuran) segment; and
e) glycidol.
23. The coating of claim 22 , wherein the reaction product further comprises:
a) acid moieties that result from the dimethylol propionic acid;
b) glycidyl moieties as a reacted product of the glycidol; and
c) wherein the diisocyanate is 4,4′-methylene diphenyl diisocyanate.
24. The coating of claim 23 , wherein the reaction product further comprises an amide moiety as the reacted product of excess 4,4′-methylene diphenyl diisocyanate and the dimethylol propionic acid.
25. The coating of claim 24 wherein the reaction product further comprises urea moeities.
26. The coating of claim 22 , wherein the reactants further comprise adipic acid dihydrazide.
27. The coating of claim 26 , wherein the reactants further comprise water.
28. The coating of claim 27 , wherein the reaction product further comprises:
a) acid moieties that result from the dimethylol propionic acid;
b) glycidyl moieties as a reacted product of the glycidol; and
c) urea moieties that result from reaction of adipic acid dihydrazide and the diisocyanate.
29. The coating of claim 27 , wherein the reaction product further comprises:
a) acid moieties that result from the dimethylol propionic acid;
b) glycidyl moieties as a reacted product of the glycidol; and
c) wherein the diisocyanate is 4,4′-methylene diphenyl diisocyanate.
30. The coating of claim 29 wherein the reaction product further comprises urea moieties that result from reaction of the diisocyanate and water.