US5162574A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Bis(4-cyanatophenyl)-1,1-ethane
Assignee: Huntsman Advanced Materials Americas LLC
•
Filing: 1990-09-13
•
Granted: 1992-11-10
•
Expires: 2010-09-13
Abstract
Abstract Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, is useful in wet filament winding, resin transfer molding and pultrusion processes.
Inventors
- 👤 Wallace M. Craig, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:10
CPC Classifications
C; C08; C08L; C08L79/00; C08L79/04; C07; C07C; C07C261/00; C07C261/02; C08G; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065; C08G73/0655
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
164 words
A process for preparing bis(4-cyanatophenyl)-1,1-ethane having a viscosity of less than 200 cps at 25° C., a reactivity at 110° C. of less than 0.3 percent trimerization per hour, and containing impurities of less than 50 ppm of tertiary amine and less than 1000 ppm of diethylcyanamide which comprises: a) reacting a solution of cyanogen halide selected from cyanogen chloride or bromide in a halocarbon solvent with a solution of bis(4-hydroxyphenyl)- 1,1-ethane, and a tertiary amine in a halocarbon solvent at a temperature below about -10° C. for a time sufficient to complete the esterification reaction; b) washing the resulting solution with aqueous acid, and c) recovering the cyanate ester product, wherein the cyanogen chloride and the dihydric phenol are present in the amount of about 1.05 to about 1.25 equivalents of cyanogen chloride to one equivalent of dihydric phenol and wherein the tertiary amine is present in the amount of about 1.005 to about 1.05 equivalents per each equivalent of the dihydric phenol.
Claim 2
Dependent Claim
164 words
A process for preparing bis(4-cyanatophenyl)-1,1-ethane having a viscosity of less than 200 cps at 25° C., a reactivity at 110° C. of less than 0.3 percent trimerization per hour, and containing impurities of less than 50 ppm of tertiary amine and less than 1000 ppm of diethylcyanamide which comprises: a) reacting a solution of cyanogen halide selected from cyanogen chloride or bromide in a halocarbon solvent with a solution of bis(4-hydroxyphenyl)- 1,1-ethane, and a tertiary amine in a halocarbon solvent at a temperature below about -10° C. for a time sufficient to complete the esterification reaction; b) washing the resulting solution with aqueous acid, and c) recovering the cyanate ester product, wherein the cyanogen chloride and the dihydric phenol are present in the amount of about 1.05 to about 1.25 equivalents of cyanogen chloride to one equivalent of dihydric phenol and wherein the tertiary amine is present in the amount of about 1.005 to about 1.05 equivalents per each equivalent of the dihydric phenol.
Claim 3
Dependent Claim
17 words
The process of claim 1 wherein the temperature is between about -10° C. and about -40° C.
Claim 4
Dependent Claim
17 words
The process of claim 2 wherein the temperature is between about -20° C. and about -30° C.
Claim 5
Dependent Claim
11 words
The process of claim 1 wherein the tertiary amine is triethylamine.
Claim 6
Dependent Claim
12 words
The process of claim 1 wherein the halocarbon solvent is methylene chloride.
Claim 7
Dependent Claim
12 words
The process of claim 1 wherein the cyanogen halide is cyanogen chloride.
Claim 8
Dependent Claim
26 words
The process of claim 1 wherein the tertiary amine is added to a slurry of the dihydric phenol in the halocarbon solvent to form a solution.
References Cited (Backward Citations)
US3107261A
Cited
US3553244A
Cited
US3740348A
Cited
US3755402A
Cited
US3448079A
Cited
US3994949A
Cited
US4046796A
Cited
US4028393A
Cited
US4060541A
Cited
US4026913A
Cited
US4748270A
Cited
US4709008A
Cited
US4839442A
Cited
US4940848A
Cited
US4831086A
Cited
US4981994A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-11-10 | 1996-05-11 | 1996-11-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-11-10 | 2000-05-11 | 2000-11-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-11-10 | 2004-05-11 | 2004-11-10 | $7700.00 | Window Closed / Lapsed |