← Back to Patent Explorer
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
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

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.

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

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag