Patent US4091000A successfully refreshed from Google Patents.
US4091000A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyurethane elastomers based on heterocyclic polyester diols
Assignee: Lim Holding SA
•
Filing: 1976-03-16
•
Granted: 1978-05-23
•
Expires: 1996-03-16
Abstract
Abstract A process for producing polyurethane elastomers in which a polyester diol is formed with a molecular weight between 3000 and 30,000 and is then reacted with a diisocyanate. ##STR1## wherein A is D, --(CH 2 ) m O-- n or ##STR2## B is --(CH 2 --or --CH= CH-- and D is a bivalent residue formed by removing the hydroxyl group from one of the following diols: Bis-[5,5-dimethyl-3- (2-hydroxyethyl)-hydantoinyl]-methane, Sebacinic acid-di-{1-methyl-2-[3-(2-hydroxyethyl]-4,4-dimethyl-hydantoinyl}-ethyl ester, 1,3-di-(2-hydroxyethyl)-5,5-dimethyl hydantoin 1,3-di-(2-hydroxyethyl)-benzimidazolone 1,3-di-(2-hydroxyethyl)-4,5,6,7-tetrabromo bezimidazolone 1,3-di-(2-hydroxyethyl-4,5,6,7-tetrahydro-bezimidazolone Bis-[5,5-dimethyl-3-(2-hydroxypropyl)-hydantoinyl]-methane 1,3-di-(2-hydroxypropyl)-5,5-dimethyl hydantoin or 1,3-di-(2-hydroxypropyl)-benzimidazolone e, m and n being whole numbers.
Inventors
- 👤 Oskar Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 15:42
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/46; C08G18/4615; C08G18/4205; C08G18/4208; C08G18/4222; C08G18/4244; C08G18/4247; C08G18/4255; C08G18/4638; C08G18/4653
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
61 words
A reaction product of a polyester diol having a molecular weight of about 5000 and diphenyl methane-4,4'-diisocyanate in an amount of about 2 moles of the diisocyanate to about 1 mole of the polyester diol, the polyester diol being formed by the reaction of 1.2 moles of ethylene glycol, 1.7 moles of adipic acid and 0.6 moles of BIS-[5,5-dimethyl-3-(2-hydroxy ethyl)-hydantoinyl] methane.
Claim 2
Dependent Claim
61 words
A reaction product of a polyester diol having a molecular weight of about 5000 and diphenyl methane-4,4'-diisocyanate in an amount of about 2 moles of the diisocyanate to about 1 mole of the polyester diol, the polyester diol being formed by the reaction of 1.2 moles of ethylene glycol, 1.7 moles of adipic acid and 0.6 moles of BIS-[5,5-dimethyl-3-(2-hydroxy ethyl)-hydantoinyl] methane.
Claim 3
Dependent Claim
77 words
A polyurethane elastomer comprising the reaction product of (a) a polyester diol having a molecular weight of 3000 to 30,000 of the formula: ##STR5## wherein A is D, --(CH 2 ) m O-- n or ##STR6## B is --(CH 2 ) 4 --, --(CH 2 ) 7 --, --(CH 2 ) 8 --, --CH═CH--, o-phenylene, m-phenylene or p-phenylene; D is a bivalent radical formed by removing the hydroxyl group from one of the following heterocyclic diols: Bis-[5,5-dimethyl-3-(2-hydroxyethyl)-hydantoinyl]-methane,
Claim 4
Dependent Claim
77 words
A polyurethane elastomer comprising the reaction product of (a) a polyester diol having a molecular weight of 3000 to 30,000 of the formula: ##STR5## wherein A is D, --(CH 2 ) m O-- n or ##STR6## B is --(CH 2 ) 4 --, --(CH 2 ) 7 --, --(CH 2 ) 8 --, --CH═CH--, o-phenylene, m-phenylene or p-phenylene; D is a bivalent radical formed by removing the hydroxyl group from one of the following heterocyclic diols: Bis-[5,5-dimethyl-3-(2-hydroxyethyl)-hydantoinyl]-methane,
Claim 5
Dependent Claim
3 words
3-di-(2-hydroxyethyl)-5,5-dimethyl hydantoin, 1,3-di-(2-hydroxyethyl)-benzimidazolone,
Claim 6
Dependent Claim
3 words
3-di-(2-hydroxyethyl)-5,5-dimethyl hydantoin, 1,3-di-(2-hydroxyethyl)-benzimidazolone,
Claim 7
Dependent Claim
102 words
3-di-(2-hydroxyethyl)-4,5,6,7-tetrabromo benzimidazolone, 1,3-di-(2-hydroxyethyl)-4,5,6,7-tetrahydro benzimidazolone, Bis-[5,5-dimethyl-3-(2-hydroxypropyl)-hydantoinyl]-methane, 1,3-di-(2-hydroxypropyl)-5,5-dimethyl hydantoin, or 1,3-di-(2-hydroxypropyl)-benzimidazolone; and e,m and n are whole numbers; and wherein the polyester diol is the reaction product of a dicarboxylic acid selected from the group consisting of adipic acid, azelaic acid, sebacic acid, maleic acid, phthalic acid, isophthalic acid, and terephthalic acid; and aliphatic diol selected from the group consisting of ethylene glycol, 1,4-butanediol, and 1,2-propanediol and the heterocyclic diol wherein the molar ratio of the dicarboxylic acid, the aliphatic diol and the heterocyclic diol is respectively about 2.8 to 2 to 1; and (b) maximally up to 20% by weight of a diisocyanate.
Claim 8
Dependent Claim
102 words
3-di-(2-hydroxyethyl)-4,5,6,7-tetrabromo benzimidazolone, 1,3-di-(2-hydroxyethyl)-4,5,6,7-tetrahydro benzimidazolone, Bis-[5,5-dimethyl-3-(2-hydroxypropyl)-hydantoinyl]-methane, 1,3-di-(2-hydroxypropyl)-5,5-dimethyl hydantoin, or 1,3-di-(2-hydroxypropyl)-benzimidazolone; and e,m and n are whole numbers; and wherein the polyester diol is the reaction product of a dicarboxylic acid selected from the group consisting of adipic acid, azelaic acid, sebacic acid, maleic acid, phthalic acid, isophthalic acid, and terephthalic acid; and aliphatic diol selected from the group consisting of ethylene glycol, 1,4-butanediol, and 1,2-propanediol and the heterocyclic diol wherein the molar ratio of the dicarboxylic acid, the aliphatic diol and the heterocyclic diol is respectively about 2.8 to 2 to 1; and (b) maximally up to 20% by weight of a diisocyanate.
Claim 9
Dependent Claim
20 words
A polyurethane elastomer defined in clain 2 wherein the polyester diol (a) has a molecular weight between 4000 and 16,000.
Claim 10
Dependent Claim
20 words
A polyurethane elastomer defined in clain 2 wherein the polyester diol (a) has a molecular weight between 4000 and 16,000.
References Cited (Backward Citations)
CA674296A
Cited
US2973339A
Cited
US2982754A
Cited
US2999851A
Cited
US3043807A
Cited
US3162616A
Cited
US3053805A
Cited
US3553172A
Cited
US3554951A
Cited
FR1486448A
Cited
US3716523A
Cited
US3919144A
Cited
US3824201A
Cited
US3935166A
Cited
US3928377A
Cited
US3954790A
Cited
US4038255A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |