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US4668780A
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Isocyanate-uretdiones and a method for their production
Assignee: Evonik Operations GmbH
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Filing: 1986-01-28
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Granted: 1987-05-26
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Expires: 2006-01-28
Abstract
Abstract Isocyanate-uretdiones having the formula: ##STR1## wherein the R groups are identical or different and are hydrocarbon groups having the formulas: ##STR2## and n is an integral or fractional number from 1 to 5. Production of the isocyanate-uretdiones, which can be dissociated by heat up to an extent of greater than 70%, is accomplished through dimerization of aliphatic diisocyanates having the formula: ##STR3## with a phosphine catalyst having the formula: X.sub.m P(NR.sub.2).sub.3-m wherein: m is 0, 1 or 2; x is a --Cl, --OR or --R group, wherein R is identical or different alkyl-, arylalkyl-, cycloalkyl, or alkyl-substituted cycloalkyl groups. The reaction temperatures are 0°-80° C. The reaction product is subjected to thin-layer distillation after a conversion of 5-70%, by weight, without deactivation of the catalyst. The compounds of the present invention are useful as intermediates in the production of starting materials for the production of polyurethanes.
Inventors
- 👤 Josef Disteldorf
- 👤 Werner Hubel
- 👤 Elmar Wolf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 10:17
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/798; C07; C07D; C07D229/00; C08G18/80; C08G18/8061; C08G18/807; C08G2150/00; C08G2150/20
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
155 words
A method for preparing an isocyanate-uretdione having a uretdione content of at least about 85% having the formula: ##STR9## wherein the R groups are identical to or different from each other and consist essentially of hydrocarbon groups having the formula: ##STR10## wherein n is an integral or fractional number from 1 to 5, which comprises: (a) dimerizing some of the isocyanate groups of an aliphatic diisocyanate compound having the formula: ##STR11## or a mixture thereof, in the presence of a catalyst compound having the formula: X.sub.m P(NR.sub.2).sub.3-m wherein m is 0, 1 or 2; x is a --Cl, --OR or R group, wherein R is identical or different alkyl, aralkyl or alkyl-substituted cycloalkyl groups, at a temperature in the range of 0°-80° C., such that said aliphatic diisocyanate or diisocyanate mixture is converted to 5-70% by weight of said isocyanate-uretdione; and (b) isolating said isocyanate-uretdione from the reaction mixture without prior deactivation of said catalyst.
Claim 2
Independent Claim
155 words
A method for preparing an isocyanate-uretdione having a uretdione content of at least about 85% having the formula: ##STR9## wherein the R groups are identical to or different from each other and consist essentially of hydrocarbon groups having the formula: ##STR10## wherein n is an integral or fractional number from 1 to 5, which comprises: (a) dimerizing some of the isocyanate groups of an aliphatic diisocyanate compound having the formula: ##STR11## or a mixture thereof, in the presence of a catalyst compound having the formula: X.sub.m P(NR.sub.2).sub.3-m wherein m is 0, 1 or 2; x is a --Cl, --OR or R group, wherein R is identical or different alkyl, aralkyl or alkyl-substituted cycloalkyl groups, at a temperature in the range of 0°-80° C., such that said aliphatic diisocyanate or diisocyanate mixture is converted to 5-70% by weight of said isocyanate-uretdione; and (b) isolating said isocyanate-uretdione from the reaction mixture without prior deactivation of said catalyst.
Claim 3
Dependent Claim
20 words
A method according to claim 1, wherein said dimerization is effected at a temperature in the range of 10°-30° C.
Claim 4
Dependent Claim
16 words
The method according to claim 1, wherein R of said catalyst is a lower alkyl group.
Claim 5
Dependent Claim
28 words
The method according to claim 1, wherein said isocyanate-uretdione is capable of readily dissociating to an extent of greater than 70% into said aliphatic diisocyanate compound or compounds.
Claim 6
Dependent Claim
31 words
The method according to claim 1, wherein said diisocyanate or diisocyanate mixture is dimerized such that about 30-60%, by weight, of said diisocyanate or diisocyanate mixture is converted to said isocyanate-uretdione.
Claim 7
Dependent Claim
20 words
The method according to claim 1, wherein said catalyst is used in the amount of 0.1 to 5% by weight.
Claim 8
Dependent Claim
11 words
The method according to claim 1, wherein said catalyst is tris-phosphine.
Claim 9
Dependent Claim
25 words
The method according to claim 1, wherein said isocyanate-uretdione is isolated from the reaction mixture by thin-layer distillation at 100°-120° C. and 0.01-0.5 mm Hg.
Claim 10
Dependent Claim
25 words
The method according to claim 1, wherein the dimerization with the aid of said catalyst is conducted at a temperature of 10° to 30° C.
Claim 11
Dependent Claim
18 words
The method according to claim 6, wherein said catalyst is used in the amount of 0.5-2% by weight.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-05-25 | 1990-11-24 | 1991-05-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-05-25 | 1994-11-24 | 1995-05-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-05-25 | 1998-11-24 | 1999-05-26 | $7700.00 | Window Closed / Lapsed |