US4707534A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Glycidylethers of fluorene-containing bisphenols
Assignee: 3M Co
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Filing: 1986-12-09
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Granted: 1987-11-17
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Expires: 2006-12-09
Abstract
Abstract Diglycidyl ethers of ortho-substituted-4-hydroxyphenylfluorenes, curable compositions comprising the diglycidyl ethers, and cured resins thereof have a high glass transition and an improved modulus of elasticity. The diglycidyl ethers of the invention for use in the curable composition of the invention can be mixtures obtained by the reaction of epihalohydrin with mixtures of fluorenebisphenols obtained by the reaction of one mole of one or more fluorenones with two or more moles or mixtures of two or more ortho-substituted phenols. The compositions are useful in molding and coating applications and in composite articles where the operating temperature of the article or material is elevated.
Inventors
- 👤 William J. Schultz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:47
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/02; C08G59/04; C08G59/06; C08G59/063; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/24; C08G59/20; C08G59/22; C08G59/24; C08G59/245
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
4 words
Glycidyl ethers of ortho-substituted-4-hydroxyphenylfluorenes.
Claim 2
Dependent Claim
4 words
Glycidyl ethers of ortho-substituted-4-hydroxyphenylfluorenes.
Claim 3
Dependent Claim
139 words
Glycidyl ethers of claim 1 having the formula ##STR10## wherein n is a number having a value of 0 to 3, and R is divalent organic group having the formula ##STR11## in which each R 0 is independently selected from hydrogen and groups that are inert in the polymerization of epoxide group-containing compounds, and each of R 1 , R 2 , R 3 , and R 4 is independently selected from hydrogen, linear and branched alkyl groups having 1 to 6 carbon atoms, phenyl and halogen; with the privisos that at least one of R 1 , R 2 , R 3 , and R 4 is a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, or halogen and the epoxy equivalent weight of the diglycidyl ether is at most about 500.
Claim 4
Dependent Claim
29 words
The glycidyl ether according to claim 2 wherein R 0 is halogen, a linear or branched alkyl group having 1 to 6 carbon atoms, phenyl, nitro, acetyl, or trimethylsilyl.
Claim 5
Dependent Claim
9 words
The glycidyl ether according to claim 2 wherein n=0.
Claim 6
Dependent Claim
21 words
The glycidyl ether according to claim 2 wherein R is derived from at least one of fluorenone or a substituted fluorenone.
Claim 7
Dependent Claim
22 words
The glycidyl ether according to claim 2 selected from the group consisting of 9,9-bis[3-methyl -4-(2,3-epoxypropoxy)phenyl]fluorene, 9,9-bis[-3,5dimethyl-4-(2,3-epoxypropoxy)phenyl]fluorene, 9,9-bis[3-chloro-4-(2,3-epoxypropoxy)phenyl)fluorene, 9-[4-(2,3-epoxypropoxy)phenyl]-9-[3-methyl-4-(2,3-epoxypropoxy)phenyl]fluorene, 9-[3-methyl -4-(2,3-epoxypropoxy)phenyl]-9-[3,5-dimethyl-4-(2-3-epoxypropoxy)phenyl]fluorene, and 9,9-bis[3,5-dibromo-4-(2,3-epoxypropoxy)phenyl]fluorene.
Claim 8
Dependent Claim
34 words
Glycidyl ethers of claim 1 prepared by the reaction of epihalohydrin with the condensation product of a mixture of two or more phenols with a fluorenone, at least one of the phenols being ortho-substituted.
Claim 9
Dependent Claim
33 words
A curable epoxy resin composition comprising (a) at least one curable epoxy resin of which at least 25 percent by weight is a glycidyl ether of an ortho-substituted-4-hydroxyphenylfluorene; and (b) epoxy resin curatives.
Claim 10
Dependent Claim
33 words
A curable epoxy resin composition comprising (a) at least one curable epoxy resin of which at least 25 percent by weight is a glycidyl ether of an ortho-substituted-4-hydroxyphenylfluorene; and (b) epoxy resin curatives.
Claim 11
Dependent Claim
18 words
The composition according to claim 8 further comprising up to 75 percent by weight of other aromatic polyepoxides.
Claim 12
Dependent Claim
35 words
The composition according to claim 9 wherein said aromatic polyepoxide is at least one of a polyglycidyl ether of a polyhydric phenol, a glycidyl ester of an aromatic carboxylic acid, a glycidylaminobenzene, and a glycidylamino-glycidyloxy-benzene.
Claim 13
Dependent Claim
27 words
The composition according to claim 10 wherein said polyglycidyl ether of a polyhydric phenol is a diglycidyl ether of bisphenol having at least one pendent carbocyclic group.
Claim 14
Independent Claim
64 words
A method comprising the steps: (a) condensing at least one ortho-substituted phenol and optionally an unsubstituted phenol with fluorenone or a substituted fluorenone to provide at least one ortho-substituted bisphenol, (b) reacting the resulting ortho-substituted bisphenol with an excess of epichlorohydrin to provide at least one diglycidyl ether of 9,9-bis (ortho-substituted-4-hydroxy-phenyl)fluorene, and (c) isolating the resulting at least one diglycidyl ether of 9,9-bis (ortho-substituted-4-hydroxyphenyl)fluorene.
Claim 15
Independent Claim
64 words
A method comprising the steps: (a) condensing at least one ortho-substituted phenol and optionally an unsubstituted phenol with fluorenone or a substituted fluorenone to provide at least one ortho-substituted bisphenol, (b) reacting the resulting ortho-substituted bisphenol with an excess of epichlorohydrin to provide at least one diglycidyl ether of 9,9-bis (ortho-substituted-4-hydroxy-phenyl)fluorene, and (c) isolating the resulting at least one diglycidyl ether of 9,9-bis (ortho-substituted-4-hydroxyphenyl)fluorene.
Claim 16
Dependent Claim
11 words
Cured resins of the curable resin composition according to claim 8.
Claim 17
Dependent Claim
15 words
Substrates impregnated or bearing a layer of the curable epoxy resin composition of claim 8.
References Cited (Backward Citations)
US2902471A
Cited
US3298998A
Cited
US3332908A
Cited
US3355511A
Cited
US3410825A
Cited
US3635843A
Cited
US3795658A
Cited
US4331582A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-11-16 | 1991-05-18 | 1991-11-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-16 | 1995-05-18 | 1995-11-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-16 | 1999-05-18 | 1999-11-17 | $7700.00 | Window Closed / Lapsed |