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US4526940A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydroxyl terminated polyfunctional epoxy curing agents

Assignee: Novartis Corp
•
Filing: 1984-07-05
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Granted: 1985-07-02
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Expires: 2004-07-05
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Abstract

Abstract A polyglycidyl derivative of an aromatic diamine, aminophenol, or polyphenol and a diglycidyl ether of a bisphenol are reacted with a bisphenol, in the presence of a catalyst at elevated temperature, to yield a reaction product wherein each glycidyl group is effectively endcapped with a moiety containing a free hydroxyl group. The ratio of equivalents of polyglycidyl compound to diglycidyl compound is 1 to 4 to 1 to 1, and of bisphenol to total glycidyl compounds is 1.8 to 1 to 2.4 to 1. Said product is useful for curing solid epoxy resins. The epoxy resins cured by said product have a dense crosslinked network resulting in concomitant superior coating properties especially chemical resistance while maintaining good flexibility.

Inventors

  • 👤 John P. Seymour
  • 👤 John A. Gannon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 11:55
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/182; C08G59/20; C08G59/32; C08G59/38

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 271 words
A polyfunctional phenolic hydroxyl terminated hardener product, useful in the curing of epoxy resins, which is the reaction product of (a) a polyglycidyl compound of the formula I, II, III or IV, ##STR20## wherein T 1 is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene or ##STR21## where Q is alkylene of 1 to 6 carbon atoms, alkylidene of 2 to 6 carbon atoms, --SO 2 --, --SO--, --S--, --S--S--, --O-- or --CO--, T 2 is 1,2-phenylene, 1,3-phenylene or 1,4-phenylene, T 3 is 1,2,3-benzenetriyl, 1,2,4-benzenetriyl, 1,3,5-benzenetriyl or ##STR22## T 4 is ##STR23## where G 1 and G 2 are independently alkyl of 1 to 6 carbon atoms or are together alkylene of 4 to 5 carbon atoms, and (b) a diglycidyl compound of the formula glycidyl--O--E--O--glycidyl where E is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene or ##STR24## where L is a direct bond, alkylene of 1 to 6 carbon atoms or alkylidene of 2 to 6 carbon atoms, wherein the ratio of equivalents of polyglycidyl compound (a) to diglycidyl compound (b) is from 1 to 4 to 1 to 1, with (c) a bisphenol of the formula HO--E.sub.1 --OH where E 1 has the same definitions as E, but is independent of E, wherein the ratio of equivalents of bisphenol component (c) to the total equivalents of glycidyl compounds (a) plus (b) is from 1.8 to 1 to 2.4 to 1, and where each glycidyl group is effectively endcapped with a moiety containing a free phenolic hydroxyl group by reaction of components (a) and (b) with (c) in the presence of an effective amount of a catalyst for promoting said reaction at a temperature between 120° and 300° C.
Claim 2
Dependent Claim 271 words
A polyfunctional phenolic hydroxyl terminated hardener product, useful in the curing of epoxy resins, which is the reaction product of (a) a polyglycidyl compound of the formula I, II, III or IV, ##STR20## wherein T 1 is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene or ##STR21## where Q is alkylene of 1 to 6 carbon atoms, alkylidene of 2 to 6 carbon atoms, --SO 2 --, --SO--, --S--, --S--S--, --O-- or --CO--, T 2 is 1,2-phenylene, 1,3-phenylene or 1,4-phenylene, T 3 is 1,2,3-benzenetriyl, 1,2,4-benzenetriyl, 1,3,5-benzenetriyl or ##STR22## T 4 is ##STR23## where G 1 and G 2 are independently alkyl of 1 to 6 carbon atoms or are together alkylene of 4 to 5 carbon atoms, and (b) a diglycidyl compound of the formula glycidyl--O--E--O--glycidyl where E is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene or ##STR24## where L is a direct bond, alkylene of 1 to 6 carbon atoms or alkylidene of 2 to 6 carbon atoms, wherein the ratio of equivalents of polyglycidyl compound (a) to diglycidyl compound (b) is from 1 to 4 to 1 to 1, with (c) a bisphenol of the formula HO--E.sub.1 --OH where E 1 has the same definitions as E, but is independent of E, wherein the ratio of equivalents of bisphenol component (c) to the total equivalents of glycidyl compounds (a) plus (b) is from 1.8 to 1 to 2.4 to 1, and where each glycidyl group is effectively endcapped with a moiety containing a free phenolic hydroxyl group by reaction of components (a) and (b) with (c) in the presence of an effective amount of a catalyst for promoting said reaction at a temperature between 120° and 300° C.
Claim 3
Dependent Claim 20 words
A product according to claim 1 wherein T 1 is 1,3-phenylene, 1,4-phenylene or ##STR25## where Q is methylene or --O--.
Claim 4
Dependent Claim 10 words
A product according to claim 2 wherein Q is methylene.
Claim 5
Dependent Claim 11 words
A product according to claim 1 wherein T 2 is 1,4-phenylene.
Claim 6
Dependent Claim 11 words
A product according to claim 1 wherein T 3 is ##STR26##
Claim 7
Dependent Claim 11 words
A product according to claim 1 wherein T 4 is ##STR27##
Claim 8
Dependent Claim 14 words
A product according to claim 1 wherein E is ##STR28## where L is isopropylidene.
Claim 9
Dependent Claim 15 words
The product according to claim 1 wherein E 1 is ##STR29## where L is isopropylidene.
Claim 10
Dependent Claim 19 words
A product according to claim 1 wherein T 1 is ##STR30## and E and E 1 are both ##STR31##
Claim 11
Dependent Claim 19 words
A product according to claim 1 wherein T 2 is 1,4-phenylene, and E and E 1 are both ##STR32##
Claim 12
Dependent Claim 19 words
A product according to claim 1 wherein T 3 is ##STR33## and E and E 1 are both ##STR34##
Claim 13
Dependent Claim 11 words
A product according to claim 1 made using an imidazole catalyst.
Claim 14
Dependent Claim 11 words
A product according to claim 12 wherein the catalyst is 2-isopropylimidazole.
Claim 15
Dependent Claim 84 words
A curable composition comprising (A) a solid epoxy resin having more than one 1,2-epoxy group, (B) a polyfunctional phenolic hydroxyl terminated hardener product according to claim 1 or mixtures thereof, and (C) a catalytic amount of a catalyst effective in causing reaction between epoxy groups of (a) and the phenolic hydroxyl groups of (b) wherein the equivalent ratio of epoxy groups of the epoxy resin of component (A) to the phenolic hydroxyl groups of the hardener of component (b) is from 1:0.4 to 1:1.2.
Claim 16
Dependent Claim 13 words
A composition according to claim 14 wherein the ratio is 1:0.65 to 1:0.75.
Claim 17
Dependent Claim 254 words
A composition according to claim 14 wherein component (B) is the reaction product of (a) a polyglycidyl compound of the formula I, II, III or IV, ##STR35## wherein T 1 is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene or ##STR36## where Q is alkylene of 1 to 6 carbon atoms, alkylidene of 2 to 6 carbon atoms, --SO 2 --, --SO--, --S--, --S--S--, --O-- or --CO--, T 2 is 1,2-phenylene, 1,3-phenylene or 1,4-phenylene, T 3 is 1,2,3-benzenetriyl, 1,2,4-benzenetriyl, 1,3,5-benzenetriyl or ##STR37## T 4 is ##STR38## where G 1 and G 2 are independently alkyl of 1 to 6 carbon atoms or are together alkylene of 4 to 5 carbon atoms, and (b) a diglycidyl compound of the formula glycidyl--O--E--O--glycidyl where E is 1,2-phenylene, 1,3-phenylene, 1,4-phenylene or ##STR39## where L is a direct bond, alkylene of 1 to 6 carbon atoms or alkylidene of 2 to 6 carbon atoms, wherein the ratio of equivalents of polyglycidyl compound (b) is from 1 to 4 to 1 to 1, with (c) a bisphenol of the formula HO--E.sub.1 --OH where E 1 has the same definitions as E, but is independent of E, wherein the ratio of equivalents of bisphenol component (c) to the total equivalents of glycidyl compounds (a) plus (b) is from 1.8 to 1 to 2.4 to 1, and where each glycidyl group is effectively endcapped with a moiety containing a free phenolic hydroxyl group by reaction of components (a) and (b) with (c) in the presence of an effective amount of a temperature between 120° and 300° C.
Claim 18
Dependent Claim 41 words
A composition according to claim 16 wherein component (B) is the reaction product of a polyglycidyl compound of formula I where T 1 is ##STR40## of a diglycidyl compound, and of a bisphenol where E and E 1 are each ##STR41##
Claim 19
Dependent Claim 41 words
A composition according to claim 16 whrein component (b) is the reaction product of a polyglycidyl compound of formula II where T 2 is 1,4-phenylene, of a diglycidyl compound, and of a bisphenol where E and E 1 are both ##STR42##
Claim 20
Dependent Claim 40 words
A composition according to claim 16 wherein component (b) is the reaction product of a polyglycidyl compound of formula III where T 3 is ##STR43## of a diglycidyl compound, and of bisphenol where E and E 1 are both ##STR44##
Claim 21
Dependent Claim 13 words
A coating prepared by curing the curable composition according to claim 14. 7

References Cited (Backward Citations)

US2884406A Cited
US2951825A Cited
US3409497A Cited
US3477990A Cited
US3931109A Cited
US4322456A Cited
JPS4917900A Cited
US3914504A Cited
US4288565A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-07-01 1988-12-31 1989-07-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-07-01 1992-12-31 1993-07-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-07-01 1996-12-31 1997-07-02 $7700.00 Window Closed / Lapsed

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