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US4014935A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Carbodiimides
Assignee: Imperial Chemical Industries Ltd
•
Filing: 1976-03-25
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Granted: 1977-03-29
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Expires: 1996-03-25
Abstract
Abstract A process for the conversion of isocyanate groups in a refined organic isocyanate into carbodiimide groups which comprises heating said organic isocyanate with a catalyst of the formula: <IMAGE> or <IMAGE> or the 2,3 or 3,4-mono-unsaturated analogues thereof, wherein R is an optionally substituted hydrocarbyl group, R1 to R8 which may be the same or different are hydrogen, chlorine or lower alkyl, X and Y may be chlorine or bromine or X and Y taken together may represent the divalent atoms =O or =S or the divalent radial =N aryl, followed by deactivation of the catalyst by adsorption on a substrate or by addition of one or more of the halides of hydrogen, phosphorus or tin or an oxyhalide of phosphorus or sulphur. When only partial conversion takes place the carbodiimides react with further isocyanate groups to give uretonimines. The products are useful for the manufacture of polymers especially microcellular polyurethanes.
Inventors
- 👤 Arthur Ibbotson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 12:08
CPC Classifications
C; C07; C07D; C07D229/00; C07C; C07C267/00; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/74; C08G18/76; C08G18/7657; C08G18/7664; C08G18/7671; C08G18/77; C08G18/78; C08G18/79; C08G18/797; Y; Y10; Y10S; Y10S521/00; Y10S521/901
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
146 words
A process for the conversion of from 3% to 35% of the isocyanate groups in a refined aromatic polyisocyanate having two or more isocyanate groups, into carbodiimide groups which comprises heating said isocyanate with a catalyst of the formula: ##STR12## wherein R is phenyl, benzyl or ethyl, R 1 , R 2 , R 5 , R 6 , R 7 and R 8 are hydrogen, R 4 is methyl, X and Y may be chlorine or bromine or X and Y taken together may represent the divalent atoms =O or =S or the divalent radical =N aryl, m and n represent 0 or 1 and are the same in any one compound, followed by deactivation of the catalyst by adsorption on a substrate or by addition of one or more of the halides of hydrogen, phosphorus or tin or an oxyhalide of phosphorus or sulphur.
Claim 2
Dependent Claim
146 words
A process for the conversion of from 3% to 35% of the isocyanate groups in a refined aromatic polyisocyanate having two or more isocyanate groups, into carbodiimide groups which comprises heating said isocyanate with a catalyst of the formula: ##STR12## wherein R is phenyl, benzyl or ethyl, R 1 , R 2 , R 5 , R 6 , R 7 and R 8 are hydrogen, R 4 is methyl, X and Y may be chlorine or bromine or X and Y taken together may represent the divalent atoms =O or =S or the divalent radical =N aryl, m and n represent 0 or 1 and are the same in any one compound, followed by deactivation of the catalyst by adsorption on a substrate or by addition of one or more of the halides of hydrogen, phosphorus or tin or an oxyhalide of phosphorus or sulphur.
Claim 3
Dependent Claim
34 words
A process as claimed in claim 1 wherein the catalyst is deactivated by the addition of one or more of the halides of hydrogen, phosphorus or tin or an oxyhalide of phosphorus or sulphur.
Claim 4
Dependent Claim
23 words
A process as claimed in claim 1 wherein the catalyst is deactivated by adsorption on a substrate followed by removal of the substrate.
Claim 5
Dependent Claim
18 words
A process as claimed in claim 1 wherein X and Y taken together represent a divalent oxygen atom.
Claim 6
Dependent Claim
14 words
A process as claimed in claim 4 wherein the catalyst is 1-phenyl-3-methyl phospholene oxide.
Claim 7
Dependent Claim
28 words
A process as claimed in claim 1 wherein the catalyst is used in an amount of from 1 ppm to 100 ppm on the weight of the isocyanate.
Claim 8
Dependent Claim
27 words
A process as claimed in claim 6 wherein the catalyst is used in an amount of from 1 to 25 ppm on the weight of the isocyanate.
Claim 9
Dependent Claim
18 words
A process as claimed in claim 7 wherein the amount of catalyst is from 1 to 10 ppm.
Claim 10
Dependent Claim
14 words
A process as claimed in claim 1 wherein the isocyanate is a diphenylmethane diisocyanate.
Claim 11
Dependent Claim
32 words
A process as claimed in claim 1 wherein at least a proportion of the carbodiimide groups react with further isocyanate groups in the refined organic isocyanate on standing to form uretonimine groups.
Claim 12
Dependent Claim
19 words
A process as claimed in claim 1 wherein the conversion is carried out at a temperature below 150° C.
Claim 13
Dependent Claim
17 words
A process as claimed in claim 11 wherein the temperature is from 80° C to 140° C.
Claim 14
Dependent Claim
33 words
A process as claimed in claim 2 wherein deactivation of the catalyst is carried out by the addition of from one to thirty moles of a deactivating agent as claimed in claim 2.
Claim 15
Dependent Claim
14 words
A process as claimed in claim 2 wherein the deactivating agent is thionyl chloride.
Claim 16
Dependent Claim
19 words
A process as claimed in claim 3 wherein the catalyst is deactivated by absorption on a siliceous earth substrate.
Claim 17
Dependent Claim
44 words
A process as claimed in claim 1 wherein conversion of isocyanate groups is carried out beyond the desired level of conversion and the product blended with a further amount of refined isocyanate to give a product having the desired number of unconverted isocyanate groups.
Claim 18
Dependent Claim
16 words
Process as claimed in claim 1 wherein an acid acceptor is incorporated in the reaction mixture.
Claim 19
Dependent Claim
13 words
Process as claimed in claim 17 wherein the acid acceptor is a 1,2-epoxide.
Claim 20
Dependent Claim
29 words
Process as claimed in claim 17 wherein the acid acceptor is used in an amount of at least one equivalent for each gram molecule of acidity in the isocyanate.
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) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |