Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2000-08-02
2002-08-20
Pezzuto, Helen L. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S314000, C526S322000
Reexamination Certificate
active
06437069
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a curable resin composition for optical application which can provide an optical part such as a plastic lens (for example, for spectacles) and a camera lens, and optically related product such as an adhesive and a coating agent, having excellent optical properties such as refractive index, an Abbe number and transparency and various excellent mechanical properties.
RELATED ART
Because organic glass has lighter weight than inorganic glass, the organic glass is noteworthy as an lens material. Presently the organic glass made of a polymer derived from a monomer such as diethylene glycol bis(allyl carbonate) is used. The organic glass comprising diethylene glycol bis(allyl carbonate) has light weight and is excellent in impact resistance, dimensional stability, machinability, dyeability and hard coat property. The organic glass is frequently used as a spectacle lens instead of the inorganic glass.
The organic glass comprising diethylene glycol bis(allyl carbonate) has low refractive index of 1.50 so that the lens must have large thickness for practical uses whereby eliminating a merit of light weight and giving bad appearance. This trend is remarkable in particularly the lens having high power, and the organic glass comprising diethylene glycol bis(allyl carbonate) is not suitable for the spectacle lens material.
A plastic lens material having higher refractive index, which comprises a diallyl phthalate monomer or a derivative of bisphenol A, is proposed to eliminate such defects (for example, JP-A-53-7787). However, this lens material somewhat lacks in transparency, impact resistance, processability and the like. For example, because the diallyl phthalate monomer is useful as a non-volatile crosslinking agent having a high boiling point and has the high refractive index, it is an attractive optical material. The cured material of the diallyl phthalate monomer alone has the high refractive index and high cure degree. However, it is brittle and largely colored so that it cannot be used as the optical material, particularly the lens material.
In order to overcome the above defects, a high refractive index plastic lens comprising a copolymer of diallyl ester, diethylene glycol bis(allyl carbonate) and maleate diester has been recently proposed (JP-A-1-246501). This technology decreases the initial coloring after the polymerization and molding. However, the colorless transparency is important in view of the practicality of the lens, and cannot be achieved by this technology. This plastic lens has frequently cracks around the molded lens so that the brittleness of the resin can not be eliminated.
SUMMARY OF THE INVENTION
One of objects of the present invention is to provide a optical resin composition giving an optical material such as a plastic lens, having excellent optical properties, for example, a refractive index and an Abbe number, having excellent mechanical and thermal properties, for example, thermal resistance and impact resistance, and having colorless transparency and reduced brittleness of a cured material.
The present invention relates to a curable resin composition comprising:
(A) at least one aromatic diallyl compound,
(B) at least one maleate diester and/or fumarate diester represented by the general formula (1):
R
1
—OOCCH═CHCOO—R
2
(1)
wherein R
1
and R
2
is, same or different, an alkyl group, cycloalkyl group, aralkyl group, aryl group, alkenyl group or alkynyl group having 1 to 15 carbon atoms,
(C) at least one (meth)allyl carbonate compound represented by the general formula (2):
wherein R
3
and R
4
is, same or different, a hydrogen atom or a methyl group, R
5
is a divalent organic group optionally having an oxygen atom, and n is from 1 to 10, and
(D) at least one radical chain transfer agent.
DETAILED DESCRIPTION OF THE INVENTION
The aromatic diallyl compound (A) used in the present invention may be a polybasic acid ester of an ally alcohol which has an aromatic ring. Specific examples of the aromatic diallyl compound (A) include diallyl isophthalate, diallyl orthophthalate and diallyl terephthalate. These are used alone or in combination thereof Diallyl isophthalate is particularly preferable.
The amount of the aromatic diallyl compound (A) is preferably from 40 to 90% by weight, more preferably from 45 to 85% by weight, based on the total amount of the components (A)-(D).
In the general formula (1) representing the maleate diester/fumarate diester (B) used in the present invention, R
1
or R
2
is preferably a saturated hydrocarbon group (that is, a C
1-15
alkyl group and C
4-15
cycloalkyl group), a C
7-15
aralkyl group, a C
6-15
aryl group, a C
2-15
alkenyl group or a C
2-15
alkynyl group. The carbon number in R
1
and R
2
is preferably from 1 to 8, particularly from 4 to 6. R
1
and R
2
is preferably saturated.
Specific examples of the maleate diester include diphenyl maleate, benzyl phenyl maleate, dibenzyl maleate, dimethyl maleate, ethyl benzyl maleate, diethyl maleate, di-n-butyl maleate, di(2-ethylhexyl) maleate, dinonyl maleate, cyclohexyl phenyl maleate, allyl benzyl maleate, diallyl maleate and methallyl benzyl maleate.
Specific examples of the fumarate diester include diphenyl fumarate, benzyl phenyl fumarate, dibenzyl fumarate, dimethyl fumarate, ethyl benzyl fumarate, diethyl fumarate, di-n-butyl fumarate, di(2-ethylhexyl) fumarate, dinonyl fumarate, cyclohenyl phenyl fumarate, allyl benzyl fumarate, diallyl fumarate and methallyl benzyl fumarate.
Di-n-butyl maleate, dibenzyl maleate, diethyl maleate, di-n-butyl fumarate, dibenzyl fumarate and diethyl fumarate are preferable. The diester (B) may be the maleate diester, the fumarate diester or a combination of thereof, and is preferably the maleate diester.
The amount of the maleate diester/fumarate diester (B) is preferably from 1 to 30% by weight, more preferably from 3 to 20% by weight, based on the total amount of the components (A) to (D).
In the (meth)allyl carbonate compound (C), both of R
3
and R
4
are preferably a hydrogen atom.
R
5
is a divalent organic group optionally having an oxygen atom, and may be, for example, an organic group of the formula:
—A
1
—,
or
—A
2
—O—A
3
—
wherein A
1
, A
2
and A
3
each is a linear or branched alkylene group having 1 to 6 carbon atoms.
Specific examples of A
1
, A
2
and A
3
include an ethylene group, a 1-methylethylene group, a trimethylene group, a tetramethylene group, a 1-methylpropylene group and a 2,2-dimethylpropylene group.
n is from 1 to 10, for example, from 1 to 5.
Specific examples of the (meth)allyl carbonate compound (C) include ethylene glycol bis(allyl carbonate), propylene glycol bis(allyl carbonate), 1,3-propanediol bis(allyl carbonate), 1,4-butanediol bis(allyl carbonate), 1,3-butanediol bis(allyl carbonate), neopentyl glycol bis(allyl carbonate), diethylene glycol bis(allyl carbonate) and dipropylene glycol bis(allyl carbonate). Diethylene glycol bis(allyl carbonate) is preferable.
Dimers and trimers may be used in addition to the (meth)allyl carbonate compound (C) in the form of monomer.
Diethylene glycol bisallyl carbonate, diethylene glycol bisallyl carbonate dimer and diethylene glycol bisallyl carbonate trimer are particularly preferable as the (meth)allyl carbonate compound (C).
The amount of the (meth)allyl carbonate compound (C) is preferably from 5 to 50% by weight, more preferably from 10 to 40% by weight, based on the total amount of components (A) to (D).
Specific examples of the radical chain transfer agent (D) used in the present invention include mercaptans, halogenated hydrocarbons and phenyl-containing monoolefins.
The mercaptans may be a compound having one mercapto group. Specific examples of the mercaptans include octyl mercaptan, lauryl mercaptan, t-dodecyl mercaptan, n-hexadecyl mercaptan, n-tetradecyl mercaptan, m-thiocresol, thiophenol, thioglycol (2-mercaptoethanol), 2-ethylhexyl thioglycolate and &bgr;-naphthalene thiol.
The halogenated hydrocarbons are hydrocarbons substituted with at least one halogen atom, for exa
Daiso Co. Ltd.
Pezzuto Helen L.
Wenderoth , Lind & Ponack, L.L.P.
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