US4731423A
Expired / Lapsed
US
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Meta-halo-phenolic alkylation products and epoxy systems
Assignee: Huntsman Advanced Materials Americas LLC
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Filing: 1986-08-13
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Granted: 1988-03-15
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Expires: 2006-08-13
Abstract
Abstract Titled materials and their preparation. The materials contain a moiety such as, for example, 4-oxy-3,5-dimethyl-2,6-dibromobenzyl which can impart a high degree of thermal and hydrolytic stability to the materials, for example, epoxy thermosets such as in electronic encapsulations. For example, when used in electronic encapsulation formulations, these materials can provide a substantial increase in electronic device reliability. Their preparation involves an alkylation of an aromatic ring, for example, such as a Friedel-Crafts alkylation with 4-bromomethyl-3,5-dibromo-2,6-dimethylphenol or with 4-hydroxymethyl-3,5-dibromo-2,6-dimethylphenol.
Inventors
- 👤 Abel Mendoza
- 👤 Chun S. Wang
- 👤 Eric E. Bancroft
- 👤 David B. Fritz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 04:22
CPC Classifications
C; C07; C07C; C07C39/00; C07C39/02; C07C39/06; C07C39/24; C07C39/42; C07C39/12; C07C39/367; C08; C08G; C08G59/00; C08G59/02; C08G59/04; C08G59/06; C08G59/08; C08G59/18; C08G59/20; C08G59/22; C08G59/30
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
86 words
A coupled aromatic compound represented by the formula Ar-Y wherein Ar is an aromatic moiety different from Y and Y is an aromatic moiety represented by one of the formulae: ##STR22## wherein A is an aliphatic ring system bonded to the aromatic ring; Q is separately at each occurrence hydrogen, alkyl or inertly-substituted alkyl provided that the carbon bonded to the aromatic ring is a primary or secondary carbon; X is separately at each occurrence a halogen moiety; and Z is a nitrogen- or chalcogen-containing moiety.
Claim 2
Dependent Claim
86 words
A coupled aromatic compound represented by the formula Ar-Y wherein Ar is an aromatic moiety different from Y and Y is an aromatic moiety represented by one of the formulae: ##STR22## wherein A is an aliphatic ring system bonded to the aromatic ring; Q is separately at each occurrence hydrogen, alkyl or inertly-substituted alkyl provided that the carbon bonded to the aromatic ring is a primary or secondary carbon; X is separately at each occurrence a halogen moiety; and Z is a nitrogen- or chalcogen-containing moiety.
Claim 3
Dependent Claim
34 words
The compound of claim 1 wherein X is Br or Cl and Z is NH 2 , NHR, NR 2 , OH, OR, ##STR23## wherein R is hydrocarbyl having from 1 to 12 carbons.
Claim 4
Dependent Claim
21 words
The compound of claim 2 wherein Q is alkyl having 1 to 12 carbons, Z is OH and X is Br.
Claim 5
Dependent Claim
23 words
The composition of claim 1 which is a novolac resin containing at least 1/2 percent by weight of the moiety represented by Y.
Claim 6
Dependent Claim
15 words
The composition of claim 4 wherein the Y moiety is a 2,6-dihalo-4-hydroxy-3,5-di(C 1-10 alkyl)benzyl moiety.
Claim 7
Dependent Claim
13 words
The composition of claim 5 wherein the 2,6-dihalo-4-hydroxy-3,5-di(C 1-10 alkyl)benzyl moiety is 2,6-dibromo-4-hydroxy-3,5-dimethylbenzyl.
Claim 8
Dependent Claim
22 words
The composition of claim 6 wherein the weight percent of bromine attributable to 2,6-dibromo-4-hydroxy-3,5-dimethylbenzyl moieties is from about one to 20 percent.
Claim 9
Dependent Claim
19 words
The composition of claim 7 wherein the weight percent of bromine is from about 5 to about 15 percent.
Claim 10
Dependent Claim
24 words
The composition of claim 1 which is a cured epoxy thermoset containing at least 1/2 percent by weight of the moiety represented by Y.
Claim 11
Dependent Claim
22 words
The composition of claim 9 which contains from about 1/2 to about 20 percent by weight of halogen attributable to Y moieties.
Claim 12
Dependent Claim
14 words
The composition of claim 10 wherein the Y moieties are 2,6-dihalo-4-hydroxy-3,5-di(C 1-10 alkyl)benzyl moieties.
Claim 13
Dependent Claim
14 words
The composition of claim 9 which is an encapsulation formulation suitable for electronic use.
Claim 14
Dependent Claim
62 words
The composition of claim 12 wherein the Y moieties contain 2,6-dibromo-4-substituted oxy-3,5-dimethylbenzyl moieties with the 2,6-dibromo moieties present from about 1/2 to about 3 weight percent of the encapsulation formulation which has as the cured epoxy thermoset resin a cured epoxy thermoset prepared from at least, an epoxidized cresol formaldehyde novolac or an epoxidized dicyclopentadiene phenol novolac, each containing said Y moieties.
Claim 15
Dependent Claim
25 words
The composition of claim 1 which is an aromatic-containing polymeric resin which contains at least 1/2 percent by weight of the moiety represented by Y.
Claim 16
Dependent Claim
57 words
A process for the preparation of the coupled aromatic compound of claim 1 which process comprises contacting an aromatic compound with an alkylating aromatic agent represented by the formula (hm)-Y wherein hm is Br, Cl, OH or C 1-4 alkoxy and Y is represented by the formulae: ##STR24## under conditions sufficient to form the coupled aromatic compound.
Claim 17
Dependent Claim
67 words
The process of claim 15 wherein the alkylating agent is represented by the formula: ##STR25## wherein X is separately at each occurrence a halogen moiety selected from the group consisting of fluoro, chloro and bromo; Q is separately at each occurrence hydrogen, or C 1-12 alkyl or inertly-substituted alkyl, each with at most a secondary carbon attached to the six-membered ring; and Q"' is H or organic.
Claim 18
Dependent Claim
31 words
The process of claim 16 wherein X is separately at each occurrence a halogen moiety selected from the group consisting of chloro and bromo; Q is methyl; and Q"' is H.
Claim 19
Dependent Claim
10 words
The process of claim 17 wherein the agent is 4-bromomethyl-3,5-dibromo-2,6-dimethylphenol.
Claim 20
Dependent Claim
10 words
The process of claim 17 wherein the agent is 3,5-dibromo-4-hydroxymethyl-2,6-dimethylphenol.
Claim 21
Dependent Claim
20 words
The process of claim 16 wherein the aromatic compound is selected from the group consisting of alkyl phenols and novolacs.
Claim 22
Dependent Claim
13 words
The process of claim 19 wherein the aromatic compound is a hydroxy-containing aromatic.
Claim 23
Dependent Claim
13 words
The process of claim 21 wherein the hydroxy-containing aromatic is a novolac resin.
Claim 24
Dependent Claim
12 words
The process of claim 18 wherein the aromatic compound is alkyl phenol.
Claim 25
Dependent Claim
32 words
The process of claim 16 wherein the aromatic compound is a hydroxy-containing aromatic and further wherein etherification with an epichlorohydrin is carried out to prepare a vicinal halohydrin organo-oxy containing meta-halo-phenoxy-coupled aromatic.
Claim 26
Dependent Claim
22 words
The process of claim 24 further wherein epoxidation of the vicinal halohydrin organo-oxy moiety is carried out to prepare a meta-halo-phenoxyepoxy-coupled aromatic.
Claim 27
Dependent Claim
18 words
The process of claim 25 wherein the epihalohydrin is epichlorohydrin, and the meta-halo-phenoxyepoxy-coupled aromatic contains a 2,3-epoxypropoxy moiety.
Claim 28
Dependent Claim
18 words
The process of claim 25 further wherein the meta-halo-phenoxyepoxy-coupled aromatic is cured to prepare a cured epoxy system.
Claim 29
Dependent Claim
21 words
The process of claim 27 wherein the cured epoxy system contains 4-oxy-3,5-dimethyl-2,6-dibromobenzyl which is coupled at the 4-oxy and benzylic positions.
Claim 30
Dependent Claim
26 words
The process of claim 27 wherein a meta-halo-phenoxy-coupled aromatic is used as the curing agent to prepare a cured epoxy system containing a coupled oxyhalomesitylic moiety.
References Cited (Backward Citations)
US3402169A
Cited
GB1356508A
Cited
US3929908A
Cited
US3956403A
Cited
US4058570A
Cited
US4377712A
Cited
US4266054A
Cited
US4447660A
Cited
US4499255A
Cited
US4499255B1
Cited
JPS60210615A
Cited
US4684752A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-03-15 | 1991-09-14 | 1992-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-15 | 1995-09-14 | 1996-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-15 | 1999-09-14 | 2000-03-15 | $7700.00 | Window Closed / Lapsed |