US5019636A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyester chain-extended vinyl ether urethane oligomers
Assignee: Honeywell International Inc
•
Filing: 1989-05-10
•
Granted: 1991-05-28
•
Expires: 2009-05-10
Abstract
Abstract A vinyl ether oligomer especially useful for coatings is prepared by reacting an hydroxyl-terminated polyester, a diisocyanate, and a hydroxy monovinyl ether having formulas as defined herein.
Inventors
- 👤 Stephen C. Lapin
- 👤 James R. Snyder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 18:16
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/70; C08G18/81; C08G18/8141; C08G18/815; C08G18/8158; C08G18/8166; C08G18/40; C08G18/42; C08G18/671; C08G18/6715
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
179 words
A vinyl ether urethane oligomer consisting essentially of the reaction product of (a) an hydroxyl-terminated polyester having the formula ##STR3## where X is a divalent radical selected from the group consisting of ##STR4## where n is an integer from 2 to 6 Y is a divalent radical selected from the group consisting of --(CH 2 ) n -- where n is 2,3,4 and 1,2, 1,3, or 1,4 phenylene groups m has an average value of 1 to about 100 and (b) a diisocyanate having the formula OCN--Q--NCO where Q is selected from the group consisting of divalent radicals derived from toluene, 4,4'-diphenylmethane, tetramethyl xylene, isophorone, and 4,4'-dicyclohexylmethane and n-hexane or a polyisocyanate having a functionality of 2 or more and (c) a hydroxy monovinyl ether having the formula R'CH"═CR"O--Z--OH where R' and R" are monovalent radicals selected from the group consisting of H and alkyl groups having 1-10 carbon atoms Z is selected from the group consisting of divalent radicals derived from butane diol, 1,4-bis(methyl)cyclohexane diol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, and tripropylene glycol.
Claim 2
Dependent Claim
179 words
A vinyl ether urethane oligomer consisting essentially of the reaction product of (a) an hydroxyl-terminated polyester having the formula ##STR3## where X is a divalent radical selected from the group consisting of ##STR4## where n is an integer from 2 to 6 Y is a divalent radical selected from the group consisting of --(CH 2 ) n -- where n is 2,3,4 and 1,2, 1,3, or 1,4 phenylene groups m has an average value of 1 to about 100 and (b) a diisocyanate having the formula OCN--Q--NCO where Q is selected from the group consisting of divalent radicals derived from toluene, 4,4'-diphenylmethane, tetramethyl xylene, isophorone, and 4,4'-dicyclohexylmethane and n-hexane or a polyisocyanate having a functionality of 2 or more and (c) a hydroxy monovinyl ether having the formula R'CH"═CR"O--Z--OH where R' and R" are monovalent radicals selected from the group consisting of H and alkyl groups having 1-10 carbon atoms Z is selected from the group consisting of divalent radicals derived from butane diol, 1,4-bis(methyl)cyclohexane diol, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, and tripropylene glycol.
Claim 3
Dependent Claim
27 words
The oligomer of claim 1 where polyester (a) is first reacted with diisocyanate (b) and thereafter the first reaction product is reacted with the monovinyl ether (c).
Claim 4
Dependent Claim
27 words
The oligomer of claim 1 where diisocyanate (b) and monovinyl ether (c) are first reacted and thereafter the first reaction product is reacted with the polyester (a).
Claim 5
Dependent Claim
12 words
The oligomer of claim 1 wherein (a), (b) and (c) are co-reacted.
Claim 6
Dependent Claim
44 words
The oligomer of claim 1 wherein the ratio of the hydroxyl groups of (a) to the hydroxyl groups of (c) is about 0.5 to 5 and the ratio of the hydroxyl groups (a) and (c) to the isocyanate groups of (b) is about 1:1.
Claim 7
Dependent Claim
18 words
The oligomer of claim 1 wherein (a), (b), and (c) are reacted in the absence of a solvent.
Claim 8
Dependent Claim
26 words
The oligomer of claim 1 wherein (a), (b), and (c) are reacted in the presence of a divinyl ether monomer which is retained with the oligomer.
Claim 9
Dependent Claim
24 words
The oligomer of claim 1 wherein (a), (b), and (c) are reacted in the presence of a solvent which is removed from the oligomer.
Claim 10
Dependent Claim
20 words
The oligomer of claim 1 wherein the excess hydroxyl groups are less than 10 mol percent of those initially present.
Claim 11
Dependent Claim
20 words
The oligomer of claim 9 wherein the excess hydroxyl groups are less than 1 mol percent of those initially present.
Claim 12
Dependent Claim
20 words
The oligomer of claim 1 wherein the excess isocyanate groups are less than 1 mol percent of those initially present.
Claim 13
Dependent Claim
27 words
The oligomer of claim 1 wherein polyester (a) is hydroxyl-terminated poly(neopentyl adipate), diisocyanate (b) is 4,4'-diphenyl methane diisocyanate, and monovinyl ether (c) is 4-hydroxymethyl cyclohexylmethyl vinyl ether.
Claim 14
Dependent Claim
25 words
The oligomer of claim wherein polyester (a) is hydroxyl-terminated poly(propylene adipate), diisocyanate (b) is 4,4'-diphenylmethane diisocyanate, and monovinyl ether (c) is 4-hydroxymethyl cyclohexylmethyl vinyl ether.
Claim 15
Dependent Claim
25 words
The oligomer of claim 1 where polyester (a) is hydroxyl-terminated poly(propylene adipate), diisocyanate (b) is 4,4'-diphenylmethane diisocyanate, and monovinyl ether (c) is 4-hydroxybutyl vinyl ether.
Claim 16
Dependent Claim
27 words
The oligomer of claim 1 wherein polyester (a) is hydroxy-terminated poly (propylene adipate), diisocyanate (b) is isophorone diisocyanate, and monovinyl ether (c) is 4-hydroxy butyl vinyl ether.
Claim 17
Dependent Claim
21 words
The oligomer of claim 1 wherein in polyester (a) X and/or Y are mixtures of two or more different divalent radicals.
Claim 18
Dependent Claim
13 words
The oligomer of claim 1 wherein the polyester (a) is hydroxyl-terminated poly(propylene adipate).
Claim 19
Dependent Claim
13 words
The oligomer of claim 1 wherein the polyester (a) is hydroxyl-terminated poly(neopentyl adipate).
Claim 20
Dependent Claim
13 words
The oligomer of claim 1 wherein the polyester (a) is hydroxyl-terminated poly(1,4-butane adipate).
Claim 21
Dependent Claim
13 words
The oligomer of claim 1 wherein the polyester (a) is hydroxyl-terminated poly(1,6-hexane adipate).
Claim 22
Dependent Claim
13 words
The oligomer of claim 1 wherein the polyester (a) is hydroxyl-terminated poly(neopentyl isophthalate).
Claim 23
Dependent Claim
13 words
The oligomer of claim 1 wherein the polyester (a) is hydroxyl-terminated poly(1,6-hexane isophthalate).
Claim 24
Dependent Claim
13 words
The oligomer of claim 1 wherein the diisocyanate (b) is 4,4'-diphenyl methane diisocyanate.
Claim 25
Dependent Claim
12 words
The oligomer of claim 1 wherein the diisocyanate (b) is toluene diisocyanate.
Claim 26
Dependent Claim
12 words
The oligomer of claim 1 wherein the diisocyanate (b) is isophorone diisocyanate.
Claim 27
Dependent Claim
13 words
The oligomer of claim 1 wherein the diisocyanate (b) is m-tetramethyl xylene diisocyanate.
Claim 28
Dependent Claim
13 words
The oligomer of claim 1 wherein the diisocyanate (b) is 4,4'-dicyclohexyl methane diisocyanate.
Claim 29
Dependent Claim
12 words
The oligomer of claim 1 wherein the diisocyanate (b) is 1,6-hexamethylene diisocyanate.
Claim 30
Dependent Claim
15 words
The oligomer of claim 1 wherein the monovinyl ether (c) is 4-hydroxy butyl vinyl ether.
Claim 31
Dependent Claim
15 words
The oligomer of claim 1 wherein the monovinyl ether (c) is 4-hydroxymethyl cyclohexylmethyl vinyl ether.
Claim 32
Dependent Claim
15 words
The oligomer of claim 1 wherein the monovinyl ether (c) is 2-hydroxy ethyl vinyl ether.
Claim 33
Dependent Claim
15 words
The oligomer of claim 1 wherein the monovinyl ether (c) is triethylene glycol monovinyl ether.
Claim 34
Dependent Claim
15 words
The oligomer of claim 1 wherein the monovinyl ether (c) is diethylene glycol monovinyl ether.
Claim 35
Dependent Claim
10 words
The polymer resulting from curing the oligomer of claim 1.
Claim 36
Dependent Claim
24 words
The polymer of claim 34 wherein said oligomer is cured by electron beam with a dosage of from about 0.1 to about 10 Mrads.
Claim 37
Dependent Claim
13 words
The polymer of claim 34 wherein said oligomer is cured by ultraviolet radiation.
Claim 38
Dependent Claim
12 words
The polymer of claim 34 wherein said oligomer is cured by heating.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-05-27 | 1994-11-26 | 1995-05-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-05-27 | 1998-11-26 | 1999-05-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-05-27 | 2002-11-26 | 2003-05-28 | $7700.00 | Window Closed / Lapsed |