Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
1997-06-30
2002-10-22
Mullis, Jeffrey (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S508000, C528S087000, C528S088000, C528S102000, C528S128000, C528S155000, C528S161000
Reexamination Certificate
active
06469109
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to an aryl ester compound which can be used mainly as a curing agent for an epoxy resin and can give a cured product having a low dielectric constant and a low dielectric loss tangent; an epoxy resin composition using the same, and a laminate prepared using the epoxy resin composition. These are suitable for a molding material, a paint and varnish, a coating material, a civil engineering material, a constructional material and in particular, in the electric or electronic uses which work at high-frequency region, for example, a resin for laminate or an IC-sealing resin.
2. Description of the Prior Art
Among the epoxy resins used in the electric and electronic uses, the resin for a printed wiring board has heretofore been mainly a combination of a bisphenol type epoxy resin with a dicyandiamide. In recent years, the resin has been required to have a low dielectric constant for the purpose of the improvement of signal velocity and the impedance-matching of circuit as the printed wiring board has been made thinner and more multiple in layer and also required to have a low dielectric loss tangent for the purpose of diminishing the signal transmission loss as a high-frequency signal is used. For these purposes, a method of combining a conventional epoxy resin with a thermoplastic resin having a low dielectric constant and a low dielectric loss tangent has been devised. For example, a method of modifying the epoxy resin with a reactive polybutadiene resin and a method of dispersing a polytetrafluoroethylene resin powder have been proposed.
However, in these prior techniques, the epoxy resin which is the basic material has a high dielectric constant, and hence, the proportion of the thermoplastic resin to be combined becomes large in order to achieve the desired dielectric constant, and hence, the heat resistance, adhesiveness, dimension stability, chemical resistance and the like which are characteristic features of the epoxy resin are damaged. Therefore, there have been earnestly desired such an epoxy resin curing agent that a cured product having a low dielectric constant and a low dielectric loss tangent can be obtained without damaging the heat resistance, adhesiveness and processibility of an epoxy resin and an epoxy resin composition containing the curing agent.
The present inventors have made extensive research on the functional group structure and skeletal structure of a compound capable of thermal cure reaction with an epoxy resin, and have consequently found that an epoxy resin composition comprising a compound having a specific functional group structure and a specific skeletal structure can meet the above-mentioned purposes.
SUMMARY OF THE INVENTION
According to this invention, there are provided an aryl ester compound composed of a polyhydric phenol in which at least one OH group has been esterified with an organic acid or its derivatives having 1 to 20 carbon atoms, said polyhydric phenol being the condensation product of a substituted or unsubstituted resorcinol represented by the general formula (1):
wherein each P represents independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms and i represents an integer of 0 to 2, with a carbonyl compound represented by the general formula (2):
wherein each of X and X′ represents independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, provided that X and X′ may form a ring together with the carbon atom to which X and X′ are attached;
a process for producing said aryl ester compound which comprises condensing the substituted or unsubstituted resorcinol represented by the general formula (1) with the carbonyl compound represented by the general formula (2) in the presence of an acid catalyst and then esterified the condensation product thus obtained with an organic acid or its derivatives having 1 to 20 carbon atoms in the presence of a basic compound; an epoxy resin composition which comprises as the essential components:
(A) an epoxy resin,
(B) an aryl ester compound composed of a polyhydric phenol in which at least one OH group has been esterified with an organic acid or its derivatives having 1 to 20 carbon atoms, said polyhydric phenol being a condensation product of a phenolic compound represented by the general formula (4):
wherein P and i are the same as defined above and Q represents a hydrogen atom or a hydroxyl group, with the carbonyl compound represented by the general formula (2), and
(C) a cure accelerator; and
a copper-clad laminate obtained by thermoforming a copper foil and a prepreg obtained by impregnating a substrate with the above epoxy resin composition or a solution of the above epoxy resin composition in an organic solvent.
DETAILED DESCRIPTION OF THE INVENTION
The aryl ester compound of this invention and the component (B) of the epoxy resin composition of this invention are preferably aryl ester compounds represented by the general formula (3):
wherein n represents the average number of the repeated units and is a value of 1 to 20; each P represents independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms; i represents an integer of 0 to 2; each of R
1
, R
2
, R
3
, R
4
and R
5
represents independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, provided that R
1
and R
2
may form a ring together with the carbon atom to which R
1
and R
2
are attached or R
4
and R
5
may form a ring together with the carbon atoms to which R
4
and R
5
are attached; each Z represents independently a hydrogen atom or an acyl group having 1 to 20 carbon atoms, provided that the case where all Z groups are hydrogen atoms is excluded.
In the general formula (3), Z's may be acyl groups in (n+2) places on average per one molecule (in this case, the esterification percentage is taken as 100%); however, Z's are such that the esterification percentage may be any value in other cases than where all Z groups are hydrogen atoms (in this case, the esterification percentage is 0%). In order to achieve the purpose of low dielectric constant and low dielectric loss tangent, the esterification percentage is preferably at least 30%, more preferably at least 50%.
In the general formula (3), n represents the average number of the repeated units and may be a value of 1 to 20. However, in view of operability, the average number is preferably a value of 1 to 10.
The polyhydric phenol compound which is used as the starting material for the aryl ester compound can be obtained in such a known manner that resorcinols are condensed with a carbonyl compound in the presence of an acid. The resorcinols are substituted or unsubstituted resorcinols represented by the above general formula (1).
Here, the resorcinols are such as not to have substituents at the 4- and 6-positions and includes resorcinol; alkyl resorcinols, representatives of which are 2-methylresorcinol, 5-methylresorcinol, 2-propylresorcinol, 2-n-butylresorcinol, 5-isobutylresorcinol, 5-t-butylresorcinol, 5-octylresorcinol, 5-nonylresorcinol, 2,5-dimethylresorcinol, 2,5-diethylresorcinol, 2,5-diisopropylresorcinol, 2-methyl-5-butylresorcinol, 2-methyl-5-nonylresorcinol and the like; cycloalkylresorcinols, representatives of which are 2-cyclopentylresorcinol, 2-cyclohexylresorcinol, 2-cycloheptylresorcinol and the like; arylresorcinols such as 5-phenylresorcinol, 5-naphthylresorcinol and the like; aralkylresorcinols such
Endo Yasuhiro
Shibata Mitsuhiro
Ueda Youichi
Yamasaki Kaori
Fitch Even Tabin & Flannery
Mullis Jeffrey
Sumitomo Chemical Company Limited
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