US4831086A
Expired / Lapsed
US
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Cyanato group containing phenolic resins, phenolic triazines derived therefrom
Assignee: Honeywell International Inc
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Filing: 1987-10-05
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Granted: 1989-05-16
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Expires: 2007-10-05
Abstract
Abstract The present invention is a cyanato group containing phenolic resin of the formula: ##STR1## wherein n is 0 or an integer of one or more, and R is the same or different and is selected from the group consisting of hydrogen and methyl radicals. The advancement over the art is that the resin of the present invention is stable and has a long shelf life. This is indicated by the gel time of greater than 1 minute, preferably greater than 2 minutes, more preferably greater than 10 minutes, and most preferably greater than 20 minutes at 155° C. Alternately, the improved phenolic triazine resin of the present invention can be characterized as having a thermal stability indicated by thermal decomposition temperature of at least 400° C. and preferably of at least 450° C. as measured by Thermal Gravimetric Analysis (TGA).
Inventors
- 👤 Sajal Das
- 👤 Dusan C. Prevorsek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 14:04
CPC Classifications
C; C08; C08G; C08G8/00; C08G73/00; C08G73/06; C08G73/0622; C08G73/0638; C08G73/065; C08G73/0655
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
57 words
A cyanato group containing phenolic resin of the formula ##STR5## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin having a gel time of greater than 1 minute at 155° C., with no smoke generation during gel time measurement.
Claim 2
Dependent Claim
57 words
A cyanato group containing phenolic resin of the formula ##STR5## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin having a gel time of greater than 1 minute at 155° C., with no smoke generation during gel time measurement.
Claim 3
Dependent Claim
14 words
The resin of claim 1 wherein the gel time is greater than 2 minutes.
Claim 4
Dependent Claim
14 words
The resin of claim 2 wherein the gel time is greater than 10 minutes.
Claim 5
Dependent Claim
16 words
A phenolic triazine resin derived from the cyanato group containing phenolic resin recited in claim 1.
Claim 6
Dependent Claim
59 words
A cyanato group containing phenolic resin of the formula ##STR6## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin being capable of forming phenolic triazine resin having a thermal stability of at least 450° C. as measured by thermal gravimetric analysis.
Claim 7
Dependent Claim
59 words
A cyanato group containing phenolic resin of the formula ##STR6## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin being capable of forming phenolic triazine resin having a thermal stability of at least 450° C. as measured by thermal gravimetric analysis.
Claim 8
Dependent Claim
16 words
A phenolic triazine resin derived from the cyanato group containing phenolic resin recited in claim 5.
Claim 9
Dependent Claim
51 words
A cyanato group containing phenolic resin of the formula ##STR7## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin having a residual amount of dialkyl cyanamide of less than 1 percent by weight.
Claim 10
Dependent Claim
51 words
A cyanato group containing phenolic resin of the formula ##STR7## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin having a residual amount of dialkyl cyanamide of less than 1 percent by weight.
Claim 11
Dependent Claim
16 words
A phenolic triazine resin derived from the cyanato group containing phenolic resin recited in claim 7.
Claim 12
Dependent Claim
18 words
The resin of claim 1 having a residual amount of phenyl cyanate of less than 0.5% by weight.
Claim 13
Dependent Claim
16 words
A phenolic triazine resin derived from the cyanato group containing phenolic resin recited in claim 9.
Claim 14
Dependent Claim
58 words
A phenolic triazine resin derived from a cyanato group containing phenolic resin of the formula ##STR8## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin having a thermal stability of at least 450° C. as measured by thermal gravimetric analysis.
Claim 15
Dependent Claim
58 words
A phenolic triazine resin derived from a cyanato group containing phenolic resin of the formula ##STR8## wherein n is 0 or an integer of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, the resin having a thermal stability of at least 450° C. as measured by thermal gravimetric analysis.
Claim 16
Dependent Claim
22 words
the phenolic triazine resin as recited in claim 11 having a char yield of at least 50% by weight at 900° C.
Claim 17
Independent Claim
107 words
A method to make a cyanato group containing phenolic resin of the formula ##STR9## wherein n is 0 or an interger of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, comprising the steps of: reacting novolac resin and a trialkyl amine in a cyclic ether solvent to form the trialkylammonium salt of novolac, followed by reacting the trialkylammonium salt with cyanogen halide in the cyclic ether to form the cyanato group containing phenolic resin the reaction being conducted below -5° C.; and purifying the cyanato group containing phenolic resin at a temperature from 0° C. to -45° C.
Claim 18
Independent Claim
107 words
A method to make a cyanato group containing phenolic resin of the formula ##STR9## wherein n is 0 or an interger of 1 or more, R is the same or different and is selected from hydrogen and methyl groups, comprising the steps of: reacting novolac resin and a trialkyl amine in a cyclic ether solvent to form the trialkylammonium salt of novolac, followed by reacting the trialkylammonium salt with cyanogen halide in the cyclic ether to form the cyanato group containing phenolic resin the reaction being conducted below -5° C.; and purifying the cyanato group containing phenolic resin at a temperature from 0° C. to -45° C.
Claim 19
Dependent Claim
22 words
The method as recited in claim 13 wherein the cyanato group containing resin has a gel time of greater than 1.0 minute.
Claim 20
Dependent Claim
22 words
The method as recited in claim 13 wherein the cyanato group containing resin has less than 0.5% by weight of phenyl cyanate.
Claim 21
Dependent Claim
24 words
The method as recited in claim 13 wherein the cyanato group containing resin has a number average molecular weight of from 320 to 1500.
Claim 22
Dependent Claim
24 words
The method as recited in claim 16 wherein the cyanato groups containing resin has a number average molecular weight of from 500 to 1000.
Claim 23
Dependent Claim
24 words
The method as recited in claim 13 wherein the step of reacting the trialkylammonium salt with the cyanogen halide at below about -5° C.
Claim 24
Dependent Claim
27 words
The method as recited in claim 18 wherein the step of reacting the trialkylammonium salt with the cyanogen halide at below about -5° C. to -45° C.
Claim 25
Dependent Claim
27 words
The method as recited in claim 19 wherein the step of reacting the trialkylammonium salt with the cyanogen halide at below about -5° C. to -30° C.
Claim 26
Dependent Claim
26 words
The method as recited in claim 20 wherein the step of reacting the trialkylammonium salt with cyanogen halide at below about -15° C. to -30° C.
Claim 27
Dependent Claim
24 words
The method as recited in claim 13 wherein the cyclic ether solvent is selected from the group consisting of tetrahyrofuran, 1,4 dioxan, and furan.
Claim 28
Dependent Claim
27 words
The method as recited in claim 13 wherein the step of reacting the trialkylammonium salt with the cyanogen halide is conducted in the presence of a base.
Claim 29
Dependent Claim
14 words
The method as recited in claim 13 wherein the cyanogen halide is cyanogen bromide.
Claim 30
Dependent Claim
13 words
The method as recited in claim 13 wherein the trialkylamine is triethyl amine.
Claim 31
Dependent Claim
22 words
The method as recited in claim 13 wherein the trialkylammonium salt of novolac concentration is from 5 to 35 percent by weight.
Claim 32
Dependent Claim
19 words
The method as recited in claim 26 wherein the salt concentration is from 10 to 20 percent by weight.
Claim 33
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 1 having a number averge molecular weight of from about 700 to 1500.
Claim 34
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 28 having a number average molecular weight of from about 700 to 1000.
Claim 35
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 5 having a number average molecular weight of from about 700 to 1500.
Claim 36
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 30 having a number average molecular weight of from about 700 to 1000.
Claim 37
Dependent Claim
24 words
The cyanato group containing phenolic resin as recited in claim 7 having a number average molecular weight of from about 700 to about 1500.
Claim 38
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 32 having a number average molecular weight of from about 700 to 1000.
Claim 39
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 9 having a number average molecular weight of from about 700 to 1500.
Claim 40
Dependent Claim
23 words
The cyanato group containing phenolic resin as recited in claim 34 having a number average molecular weight of from about 700 to 1000.
Claim 41
Dependent Claim
28 words
The phenolic triazine resin as recited in claim 11 wherein the cyanato group containing resin has a number average molecular weight of from about 700 to about 1500.
Claim 42
Dependent Claim
27 words
The phenolic triazine resin as recited in claim 36 wherein the group containing resin has a number average molecular weight of from about 700 to about 1000.
Claim 43
Dependent Claim
26 words
The method as recited in claim 13 wherein the step of purifying further comprises precipitation of the cyanato group containing resin into a non solvent vehicle.
Claim 44
Dependent Claim
14 words
The method as recited in claim 38 wherein the non solvent is an alcohol.
Claim 45
Dependent Claim
12 words
The method as recited in claim 39 wherein the nonsolvent is isopropanol.
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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) | 1992-05-15 | 1992-11-14 | 1993-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-05-15 | 1996-11-14 | 1997-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-05-15 | 2000-11-14 | 2001-05-16 | $7700.00 | Window Closed / Lapsed |