EP0430143A2
Expired / Lapsed
EP
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Novel cured epoxy resins
Assignee: Dow Chemical Co
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Filing: 1990-11-26
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Granted: —
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Expires: 2010-11-26
Abstract
Abstract The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data processing. Nonlinear optical films produced from the polymeric material show a reduced tendency to reorient due to thermal motion.
Inventors
- 👤 John J. Kester
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-27 04:50
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/20; C08G59/40; C08G59/50; G; G02; G02F; G02F1/00; G02F1/35; G02F1/355; G02F1/361; G02F1/3615; G02F1/3616; C09; C09K; C09K2323/00; C09K2323/02; C09K2323/027; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
84 words
A composition comprising the reaction product of: (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one curing agent for compound (A) whereby at least a portion of said curing agent (B) is at least a first curing agent which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group.
Claim 2
Dependent Claim
93 words
A nonlinear optical composition comprising a product exhibiting nonlinear optical properties resulting from the reaction of: (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one curing agent for compound (A) whereby at least a portion of said curing agent (B) is at least a first curing agent which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group.
Claim 3
Dependent Claim
119 words
The composition of Claim 1 or 2 wherein the first curing agent is represented by the formula: A-Ar-X where A is a pendant monovalent electron-withdrawing group, Ar is a conjugating group and X is an electron-donating group, and where A is selected from the group consisting of -NO₂, -CN, -CHO, -CO₂R, -CO₂NHR, -P(O)(OR)₂, -PR₃ + , NR₃ + , -SR₂ + where each R is independently a hydrogen or an aliphatic, cycloaliphatic or aromatic hydrocarbyl group having from 1 to 12 carbon atoms; Ar is selected from the group consisting of X is selected from the group consisting of -NH₂ and -R'-NH₂ where R' is an aliphatic, cycloaliphatic or aromatic hydrocarbylene group having from 1 to 12 carbon atoms.
Claim 4
Dependent Claim
79 words
The composition of Claim 1 or 2 wherein the first curing agent is represented by the formula: or by the formula: where A is a pendant monovalent electron-withdrawing group selected from the group consisting of -NO₂, -CN, -CHO, -CO₂R, -CO₂NHR, -P(O)(OR)₂, -PR₃ + , -NR₃ + , -SR₂ + where each R is independently a hydrogen or an aliphatic, cycloaliphatic or aromatic hydrocarbyl group having from 1 to 12 carbon atoms and Z is an azo or olefinic moiety.
Claim 5
Dependent Claim
17 words
The composition of Claim 4 wherein A is NO₂ and Z is selected from -N=N- and -C=C-.
Claim 6
Dependent Claim
23 words
The composition of Claim 1 or 2 wherein electron-withdrawing group has a level of electron withdrawing capability (Hammett constant) of greater than 0.52.
Claim 7
Dependent Claim
76 words
The composition of Claim 1 or 2 wherein curing agent (B) includes a second curing agent selected from the group consisting of amines, amides, sulfides, anhydrides and combinations thereof; and wherein the amount of the first curing agent present in the product is from 0.1 percent to 100 percent and the amount of the second curing agent present in the product is from 99.9 percent to zero percent based on the total amount of component (B).
Claim 8
Dependent Claim
38 words
The composition of Claim 1 or 2 wherein the component (A) is an epoxy compound containing an average of more than one glycidyl group per molecule selected from the group comprising glycidyl ethers, glycidyl esters and glycidyl amines.
Claim 9
Dependent Claim
26 words
The composition of Claim 8 wherein the glycidyl ether is a glycidyl ether of bisphenol or substituted bisphenol, or is a glycidyl ether of bisphenol A.
Claim 10
Dependent Claim
28 words
The composition of Claim 1 or 2 including a catalyst selected from the group consisting of tertiary amines, imidazoles, phosphonium compounds, ammonium compounds, sulfonium compounds, and mixtures thereof.
Claim 11
Dependent Claim
86 words
A process for producing a polymeric composition comprising reacting: (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one curing agent for compound (A) whereby at least a portion of said curing agent (B) is at least a first curing agent which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group.
Claim 12
Dependent Claim
119 words
A process for producing a nonlinear optical material comprising applying a stress to the reaction product of: (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one curing agent for compound (A) whereby at least a portion of said curing agent (B) is at least a first curing agent which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group; whereby the stress applied to the reaction product is sufficient to induce a net orientation in moieties of the first curing agent in the product.
Claim 13
Dependent Claim
119 words
The process of Claim 11 or 12 wherein the first curing agent is represented by the formula: A-Ar-X where A is a pendant monovalent electron-withdrawing group, Ar is a conjugating group and X is an electron-donating group, and where A is selected from the group consisting of -NO₂, -CN, -CHO, -CO₂R, -CO₂NHR, -P(O)(OR)₂, -PR₃ + , -NR₃ + , -SR₂ + where each R is independently a hydrogen or an aliphatic, cycloaliphatic or aromatic hydrocarbyl group having from 1 to 12 carbon atoms; Ar is selected from the group consisting of X is selected from the group consisting of -NH₂ and -R'-NH₂ where R' is an aliphatic, cycloaliphatic or aromatic hydrocarbylene group having from 1 to 12 carbon atoms.
Claim 14
Dependent Claim
81 words
The process of Claim 11 or 12 wherein the first curing agent is represented by the formula: or is represented by the formula: where A is a pendant monovalent electron-withdrawing group selected from the group consisting of -NO₂, -CN, -CHO, -CO₂R, -CO₂NHR, -P(O)(OR)₂, -PR₃ + , -NR₃ + , -SR₂ + where each R is independently a hydrogen or an aliphatic, cycloaliphatic or aromatic hydrocarbyl group having from 1 to 12 carbon atoms and Z is an azo or olefinic moiety.
Claim 15
Dependent Claim
17 words
The process of Claim 13 wherein A is NO₂ and Z is selected from -N=N- and -C=C-.
Claim 16
Dependent Claim
23 words
The process of Claim 11 or 12 wherein electron-withdrawing group has a level of electron withdrawing capability (Hammett constant) of greater than 0.52.
Claim 17
Dependent Claim
75 words
The process of Claim 11 or 12 wherein curing agent (B) includes a second curing agent selected from the group comprising amines, amides, sulfides, anhydrides and combinations thereof; and wherein the amount of the first curing agent present in the product is from 0.1 percent to 100 percent and the amount of the second curing agent present in the product is from 99.9 percent to zero percent based on the total amount of component (B).
Claim 18
Dependent Claim
38 words
The process of Claim 11 or 12 wherein the component (A) is an epoxy compound containing an average of more than one glycidyl group per molecule selected from the group comprising glycidyl ethers, glycidyl esters and glycidyl amines.
Claim 19
Dependent Claim
26 words
The process of Claim 18 wherein the glycidyl ether is a glycidyl ether of bisphenol or substituted bisphenol, or is a glycidyl ether of bisphenol A.
Claim 20
Dependent Claim
36 words
The process of Claim 11 or 12 wherein the reaction is carried out in the presence of a catalyst selected from the group comprising tertiary amines, imidazoles, phosphonium compounds, ammonium compounds, sulfonium compounds, and mixtures thereof.
Claim 21
Dependent Claim
11 words
The process of Claim 20 wherein the catalyst is 2-methyl imidazole.
Claim 22
Dependent Claim
25 words
The process of Claim 12 wherein the stress applied is through an external field selected from the group comprising electric, magnetic and mechanical stress fields.
Claim 23
Dependent Claim
110 words
A process for preparing a nonlinear optical material comprising substantially simultaneously (i) polymerizing a mixture of: (A) at least one compound containing an average of more than one epoxide group per molecule; and (B) at least one curing agent for compound (A) whereby at least a portion of said curing agent (B) is at least a first curing agent which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group; and (ii) applying an electric field to the mixture to form a material having nonlinear optical properties.
Claim 24
Dependent Claim
13 words
The process of Claim 23 wherein component (B) includes a second curing agent.
Claim 25
Dependent Claim
113 words
A process for preparing a nonlinear optical material comprising substantially simultaneously (i) applying an electric field to the reaction product of: (A) at least one compound containing an average of more than one epoxide group per molecule, and (B) at least one curing agent therefor; the improvement which comprises replacing at least a portion of said curing agent with a compound which contains an average of more than one active amine hydrogen atom per molecule and an average of at least one aromatic ring which contains at least one pendant monovalent electron-withdrawing group; and (ii) thermally annealing the reaction product for a period of time to form a material having nonlinear optical properties.
Claim 26
Dependent Claim
19 words
An article having nonlinear optical properties comprising a substrate coated with the polymeric material of Claim 1 or 2.
Claim 27
Dependent Claim
14 words
A particle, film, fiber or sheet of the material of Claim 1 or 2.
Claim 28
Dependent Claim
12 words
A device having the nonlinear optical material of Claim 2 incorporated therein.
Claim 29
Dependent Claim
13 words
A waveguide having as one component a nonlinear optical material of Claim 2.
References Cited (Backward Citations)
No citation records indexed.
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