Patent US4983672A successfully refreshed from Google Patents.
US4983672A
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US
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Epoxide resin compositions and method
Assignee: 3M Co
•
Filing: 1987-12-23
•
Granted: 1991-01-08
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Expires: 2007-12-23
Abstract
Abstract A method of improving epoxy resin compositions to provide a cured resin having improved glass transition temperature and toughness characteristics is provided. The method includes providing in an epoxy resin composition an effective amount of a 9,9-bis(hydroxphenyl)fluorene composition. The fluorene component acts as a chain extension agent and provides for increased glass transition temperature and less cross-link density. As a result, improved toughness occurs. In preferred applications a toughening agent is provided in the resin composition, to further enhance toughness. Preferred resin compositions, cured resins and methods of providing improved cured resins are also provided.
Inventors
- 👤 Carl J. Almer
- 👤 William J. Schultz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:23
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/62; C08L; C08L63/00; C08G59/02; C08G59/04; C08G59/06; C08G59/066; C08G59/20; C08G59/22; C08G59/24; C08G59/245; C08G59/621; C09; C09J; C09J163/00
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
76 words
A method of improving a glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the step of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; said 9,9 bis(hydroxyphenyl)fluorene composition being provided in an amount of between about 0.09 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group in a polyepoxide component from which said resin composition is formed.
Claim 2
Independent Claim
76 words
A method of improving a glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the step of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; said 9,9 bis(hydroxyphenyl)fluorene composition being provided in an amount of between about 0.09 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group in a polyepoxide component from which said resin composition is formed.
Claim 3
Dependent Claim
48 words
The method according to claim 1 including: (a) providing in said epoxy resin composition an amount of curative effective to generate cross-linking by means of reacting a substantial amount of those reactive epoxide groups in said polyepoxide component in excess of the amount of hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene.
Claim 4
Dependent Claim
31 words
The method according to claim 2 wherein: (a) said curative includes an epoxide curing agent having at least 3 reactive sites for reaction with reactive oxirane groups in said polyepoxide component.
Claim 5
Dependent Claim
62 words
The method according to claim 1 wherein said 9,9-bis(hydroxyphenyl)fluorene composition includes at least one compound according to the formula: ##STR5## wherein: each R 0 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds; and, each R 1 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds.
Claim 6
Dependent Claim
53 words
The method according to claim 4 wherein: each R 0 is independently selected from the group comprising: hydrogen; the halogens; alkyl groups having 1-6 carbon atoms; phenyl; nitro; acetyl; and, trimethylsilyl; and, each R 1 is independently selected from the group comprising: hydrogen; phenyl; the halogens; and, alkyl groups having 1-6 carbon atoms.
Claim 7
Independent Claim
75 words
A method of improving a glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the steps of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; and, (b) providing a toughening agent in said epoxy resin composition; said toughening agent being selected from the group consisting of: acrylic core/shell polymers; styrene-butadiene/methacrylate core/shell polymers; polyether polymers; carboxylated acrylonitrile/butadienes; carboxylated butadienes; and mixtures thereof.
Claim 8
Independent Claim
75 words
A method of improving a glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the steps of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; and, (b) providing a toughening agent in said epoxy resin composition; said toughening agent being selected from the group consisting of: acrylic core/shell polymers; styrene-butadiene/methacrylate core/shell polymers; polyether polymers; carboxylated acrylonitrile/butadienes; carboxylated butadienes; and mixtures thereof.
Claim 9
Dependent Claim
21 words
A resin composition comprising: (a) a polyepoxide resin; and (b) between about 0.09 and 0.7 hydroxy equivalents of a 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 10
Dependent Claim
21 words
A resin composition comprising: (a) a polyepoxide resin; and (b) between about 0.09 and 0.7 hydroxy equivalents of a 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 11
Dependent Claim
40 words
A resin composition according to claim 7 including a curative effective to generate cross-linking by means of reacting a substantial amount of those reactive epoxide groups in said polyepoxide component in excess of the amount of hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene.
Claim 12
Dependent Claim
31 words
The resin composition according to claim 7 including a curative comprising an epoxide curing agent having at least 3 reactive sites for reaction with reactive oxirane groups in said polyepoxide component.
Claim 13
Dependent Claim
15 words
A resin composition according to claim 7 including: (a) at least one elastomer toughening agent.
Claim 14
Dependent Claim
63 words
The resin composition according to claim 7 wherein said 9,9-bis(hydroxyphenyl)fluorene composition includes at least one compound according to the formula: ##STR6## wherein: each R 0 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds; and each R 1 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds.
Claim 15
Dependent Claim
54 words
The resin composition according to claim 11 wherein: each R 0 is independently selected from the group comprising: hydrogen; the halogens; alkyl groups having 1-6 carbon atoms; phenyl; nitro; acetyl; and, trimethylsilyl; and, each R 1 is independently selected from the group comprising: hydrogen; phenyl; the halogens; and, alkyl groups having 1-6 carbon atoms.
Claim 16
Dependent Claim
48 words
A resin composition comprising: (a) a polyepoxide resin; (b) between about 0.05 and 0.9 hydroxy equivalents of a 9,9-bis(hydroxyphenyl)fluorene composition; and (c) at least one toughening agent selected from the group consisting of: acrylic core/shell polymers; styrene-butadiene/methacrylate core/shell polymers; polyether polymers; carboxylated acrylonitrile/butadienes; carboxylated butadienes; and, mixtures thereof.
Claim 17
Dependent Claim
48 words
A resin composition comprising: (a) a polyepoxide resin; (b) between about 0.05 and 0.9 hydroxy equivalents of a 9,9-bis(hydroxyphenyl)fluorene composition; and (c) at least one toughening agent selected from the group consisting of: acrylic core/shell polymers; styrene-butadiene/methacrylate core/shell polymers; polyether polymers; carboxylated acrylonitrile/butadienes; carboxylated butadienes; and, mixtures thereof.
Claim 18
Dependent Claim
17 words
A composition according to claim 13 including between about 0.09 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 19
Independent Claim
59 words
A method of providing an improved cured resin; said method including steps of: (a) providing an epoxy resin composition including: (i) a curable polyepoxide resin; (ii) between 0.09 and 0.7 hydroxy equivalents of a 9,9-bis(hydroxyphenyl) fluorene composition per equivalent of reactive epoxide group in the polyepoxide resin; and (iii) a curing agent; and (b) curing said epoxy resin composition.
Claim 20
Independent Claim
59 words
A method of providing an improved cured resin; said method including steps of: (a) providing an epoxy resin composition including: (i) a curable polyepoxide resin; (ii) between 0.09 and 0.7 hydroxy equivalents of a 9,9-bis(hydroxyphenyl) fluorene composition per equivalent of reactive epoxide group in the polyepoxide resin; and (iii) a curing agent; and (b) curing said epoxy resin composition.
Claim 21
Dependent Claim
63 words
The method according to claim 15 wherein: (a) said 9,9-bis(hydroxyphenyl)fluorene composition includes at least one compound according to the formula: ##STR7## wherein: each R 0 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds; and each R 1 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds.
Claim 22
Dependent Claim
53 words
The method according to claim 16 wherein: each R 0 is independently selected from the group comprising: hydrogen; the halogens; alkyl groups having 1-6 carbon atoms; phenyl; nitro; acetyl; and, trimethylsilyl; and, each R 1 is independently selected from the group comprising: hydrogen; phenyl; the halogens; and, alkyl groups having 1-6 carbon atoms.
Claim 23
Dependent Claim
16 words
The method according to claim 15 wherein: (a) said epoxy resin includes an elastomer toughening agent.
Claim 24
Dependent Claim
12 words
An improved cured resin formed according to the method of claim 16.
Claim 25
Dependent Claim
12 words
An improved cured resin formed according to the method of claim 17.
Claim 26
Dependent Claim
12 words
An improved cured resin formed according to the method of claim 18.
Claim 27
Dependent Claim
12 words
An improved cured resin formed according to the method of claim 15.
Claim 28
Independent Claim
74 words
A method of improving glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the step of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; said 9,9-bis(hydroxyphenyl)fluorene composition being provided in an amount of between about 0.05 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group in a polyepoxide component from which said resin composition is formed.
Claim 29
Independent Claim
74 words
A method of improving glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the step of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; said 9,9-bis(hydroxyphenyl)fluorene composition being provided in an amount of between about 0.05 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group in a polyepoxide component from which said resin composition is formed.
Claim 30
Independent Claim
75 words
A method of improving glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the step of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; said 9,9-bis(hydroxyphenyl)fluorene composition being provided in an amount of about 0.05 to less than 0.9 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group in a polyepoxide component from which said resin composition is formed.
Claim 31
Independent Claim
75 words
A method of improving glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the step of: (a) providing in said epoxy resin composition an effective amount of a 9,9-bis(hydroxyphenyl)fluorene composition; said 9,9-bis(hydroxyphenyl)fluorene composition being provided in an amount of about 0.05 to less than 0.9 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group in a polyepoxide component from which said resin composition is formed.
Claim 32
Independent Claim
50 words
A method of improving a glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the steps of: (a) providing in said epoxy resin composition an effective amount of 9,9-bis(hydroxyphenyl)fluorene composition; and, (b) providing an elastomer toughening agent in said epoxy resin composition.
Claim 33
Independent Claim
50 words
A method of improving a glass transition temperature and ductility of a cured product from an epoxy resin composition; said method including the steps of: (a) providing in said epoxy resin composition an effective amount of 9,9-bis(hydroxyphenyl)fluorene composition; and, (b) providing an elastomer toughening agent in said epoxy resin composition.
Claim 34
Dependent Claim
28 words
The method according to claim 24 wherein said epoxy resin composition includes between about 0.09 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition per equivalent of reactive epoxide group.
Claim 35
Dependent Claim
62 words
The method according to claim 24 wherein said 9,9-bis(hydroxyphenyl)fluorene composition includes at least one compound according to the formula: ##STR8## wherein: each R 0 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds; and, each R 1 is independently selected from hydrogen and other groups substantially inert to the polymerization of epoxide group-containing compounds.
Claim 36
Dependent Claim
21 words
A resin composition comprising: (a) a polyepoxide resin; and, (b) about 0.05 to less than 0.9 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 37
Dependent Claim
21 words
A resin composition comprising: (a) a polyepoxide resin; and, (b) about 0.05 to less than 0.9 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 38
Dependent Claim
18 words
A resin composition according to claim 28 including about 0.05 to 0.7 hydroxy equivalents of the 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 39
Dependent Claim
25 words
A resin composition comprising: (a) a polyepoxide resin; (b) between about 0.05 and 0.9 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition; and, (c) an elastomer toughening agent.
Claim 40
Dependent Claim
25 words
A resin composition comprising: (a) a polyepoxide resin; (b) between about 0.05 and 0.9 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition; and, (c) an elastomer toughening agent.
Claim 41
Dependent Claim
17 words
A composition according to claim 30 including between about 0.09 and 0.7 hydroxy equivalents of 9,9-bis(hydroxyphenyl)fluorene composition.
Claim 42
Independent Claim
77 words
A method of providing a cured product, from an epoxy resin composition, having improved glass transition temperature and ductility; said method including steps of: (a) providing in said epoxy resin composition an effective amount of units according to the general formula: ##STR9## wherein: each R 0 and R 1 is independently selected from hydrogen and other groups substantially inert to polymerization of epoxide group-containing compounds; and, (b) providing in said epoxy resin composition an elastomer toughening agent.
Claim 43
Independent Claim
77 words
A method of providing a cured product, from an epoxy resin composition, having improved glass transition temperature and ductility; said method including steps of: (a) providing in said epoxy resin composition an effective amount of units according to the general formula: ##STR9## wherein: each R 0 and R 1 is independently selected from hydrogen and other groups substantially inert to polymerization of epoxide group-containing compounds; and, (b) providing in said epoxy resin composition an elastomer toughening agent.
Claim 44
Dependent Claim
65 words
The method according to claim 32 wherein: (a) each R 0 is independently selected from the group comprising: H; the halogens; linear and branched alkyl groups having 1-6 carbon atoms; phenyl groups; nitro groups; acetyl groups; and, trimethylsilyl groups; and, (b) each R 1 is independently selected from the group comprising: H; phenyl; the halogens; and linear and branched alkyl groups having 1-6 carbon atoms.
Claim 45
Dependent Claim
34 words
The method according to claim 32 wherein the provided elastomer toughening agent is selected from the group consisting of: acrylic core/shell polymers; styrenebutadiene/methacrylate core/shell polymers; polyether polymers; carboxylated acrylonitrile/butadienes; carboxylated butadienes; and, mixtures thereof.
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