US4415728A
Expired / Lapsed
US
⏱️ 0.0 years remaining
ε-Caprolactone co-polyesters useful for the preparation of polyurethane
Assignee: Department of National Defence
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Filing: 1980-02-25
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Granted: 1983-11-15
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Expires: 2000-02-25
Abstract
Abstract The invention disclosed relates to novel epsilon -caprolactone co-polyesters which when combined with diisocyanates are useful as binders in solid urethane-type propellant formulations. Said co-polyesters are prepared by the reaction, in the presence of a catalyst, of epsilon-caprolactone, a diol (as a co-catalyst for the reaction) and a dicarboxylic acid.
Inventors
- 👤 Meude Tremblay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 01:05
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/60; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/4266; C08G18/4286
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
134 words
A process for the preparation of block or sequenced co-polyester diols of the structural formula I H(OR.sub.3 COOR.sub.4 CO).sub.x OCH.sub.2 CH.sub.2 O[CO(CH.sub.2).sub.5 O].sub.y H I which comprises simultaneously reacting ε-caprolactone in the presence of a catalyst with (i) a diol of structural formula II HO--R--OH II as co-catalyst for the reaction wherein R is an alkyl group containing 1 to 8 carbon atoms or an alkyl group containing 1-12 carbon atoms having a nitrogen atom in its backbone; and (ii) a di-carboxylic acid of structural formula III HOOC(CH.sub.2).sub.m COOH III wherein m is an integer from 1 to 36, R 3 is the residual structure of a diol of structural formula II, R 4 is the residual structure of a diacid of structural formula III, and x and y are integers of about 1-10.
Claim 2
Dependent Claim
134 words
A process for the preparation of block or sequenced co-polyester diols of the structural formula I H(OR.sub.3 COOR.sub.4 CO).sub.x OCH.sub.2 CH.sub.2 O[CO(CH.sub.2).sub.5 O].sub.y H I which comprises simultaneously reacting ε-caprolactone in the presence of a catalyst with (i) a diol of structural formula II HO--R--OH II as co-catalyst for the reaction wherein R is an alkyl group containing 1 to 8 carbon atoms or an alkyl group containing 1-12 carbon atoms having a nitrogen atom in its backbone; and (ii) a di-carboxylic acid of structural formula III HOOC(CH.sub.2).sub.m COOH III wherein m is an integer from 1 to 36, R 3 is the residual structure of a diol of structural formula II, R 4 is the residual structure of a diacid of structural formula III, and x and y are integers of about 1-10.
Claim 3
Dependent Claim
18 words
A process according to claim 1, wherein ε-caprolactone is reacted with (i) N-methyl-diethanol amine and (ii) sebacic acid.
Claim 4
Dependent Claim
16 words
A process according to claim 1, wherein the catalyst is selected from lead-2-ethylhexanoate and tetraoctyleneglycol titanate.
Claim 5
Dependent Claim
19 words
A process according to claim 1 wherein a polycaprolactone is reacted with (i) 1,2-propane diol and (ii) adipic acid,
Claim 6
Dependent Claim
19 words
A process according to claim 1 wherein a polycaprolactone is reacted with (i) 1,2-propane diol and (ii) sebacic acid.
Claim 7
Dependent Claim
21 words
A process according to claim 4 or 5, wherein the reaction is effected in the presence of tetraoctyleneglycol titanate as catalyst.
Claim 8
Dependent Claim
18 words
A process according to claim 1, wherein ε-caprolactone is reacted with (i) propylene glycol and (ii) adipic acid.
Claim 9
Dependent Claim
18 words
A process according to claim 1, wherein ε-caprolactone is reacted with (i) propylene glycol and (ii) sebacic acid.
Claim 10
Dependent Claim
17 words
A process according to claim 1, wherein ε-caprolactone is reacted with (i) 1,3-butanediol and (ii) sebacic acid.
Claim 11
Dependent Claim
118 words
Co-polyester diols produced by the process of claim 1 and having the structural formula H(OR.sub.3 COOR.sub.4 CO).sub.x OCH.sub.2 CH.sub.2 O[CO(CH.sub.2).sub.5 O].sub.y H I wherein R 3 is the residual structure of a diol of structural formula II HO--R--OH II wherein R is an alkyl group containing 1 to 8 carbon atoms or an alkyl group containing 1-12 carbon atoms having a nitrogen atom in its backbone; wherein R 4 is the residual structure of a diacid of structural formula III or a dehydrated derivative thereof HOOC(CH.sub.2).sub.m COOH III wherein m is an integer from 1 to 36; wherein x is an integer from about 1 to 10; and wherein y is an integer from about 1 to 10.
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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) | 1986-11-14 | 1987-05-16 | 1987-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-14 | 1991-05-16 | 1991-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-14 | 1995-05-16 | 1995-11-15 | $7700.00 | Window Closed / Lapsed |