Acrylic esters and use thereof

Details Acrylic esters and use thereof Acrylic esters and use thereof

2003-01-13

2004-12-28

Lambkin, Deborah C. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S039000, C526S259000

Reexamination Certificate

active

06835844

ABSTRACT:

TECHNICAL FIELD
The present invention relates to an acrylic ester compound, a polymerizable composition containing the acrylic ester compound, and a cured product and an optical component obtained by polymerizing the polymerizable composition. Furthermore, it also relates to a sulfur-containing compound useful as a starting material at the time of manufacture of the acrylic ester compound.
BACKGROUND ART
Inorganic glass has been widely used in various fields as a transparent optical material, because of its favorable properties such as high transparency and low optical anisotropy. However, it has disadvantages of being heavy, fragile and poor in productivity. Therefore, various organic optical materials (optical resins) have been extensively developed to replace the inorganic glass.
One of the basically most important characteristics for an optical resin is transparency. The highly transparent optical resins developed so far include polymethyl methacrylate (PMMA), bisphenol A polycarbonate (BPA-PC), polystyrene (PS), methyl methacrylate/styrene copolymer (MS), styrene/acrylonitrile copolymer (SAN), poly(4-methyl-pent-1-ene) (TPX), polycycloolefin (COP), polydiethylene glycol bisallyl carbonate (EGAC) and polythiourethane (PTU).
PMMA has excellent transparency and weather resistance as well as good moldability. However, it has disadvantages of low refractive index (nd) of 1.49 and high moisture absorptivity.
BPA-PC is excellent in transparency, heat resistance, impact resistance and refractive index. However, it has disadvantages of relatively high optical anisotropy (birefringence) and high aberration (low Abbe number), which have limited its applications.
PS and MS have high moldability, high transparency, low moisture absorptivity and high refractive index. However, they have been rarely used as optical resins, because of their disadvantages of insufficient resistance to impact, weather and heat.
SAN is relatively high in refractive index, and considered to have balanced mechanical properties. However, it is also rarely used as an optical resin, because of its relatively insufficient heat resistance (thermal deformation temperature: 80 to 90° C.).
TPX and COP, although having high transparency, low moisture absorptivity and high heat resistance, include disadvantages of low refractive index (nd: 1.47 to 1.53), and insufficient impact resistance, gas barrier characteristics and dye-affinity.
EGAC is a thermosetting optical resin produced by polymerization of diethylene glycol bisallyl carbonate as a monomer, and has been most widely used for common spectacles lenses. It has favorable characteristics of high transparency, high heat resistance and very low chromatic aberration, but disadvantages of low refractive index (nd: 1.50) and insufficient impact resistance.
PTU is a thermosetting resin obtained by a reaction between a diisocyanate compound and a polythiol compound, and most widely used for spectacles lenses of superhigh refractive index. PTU is a very excellent optical resin having, in particular, high transparency and impact resistance as well as a high refractive index and low chromatic aberration. However, it inconveniently needs a long time for molding by thermal polymerization (1 to 3 days), and hence involves productivity-related problems to be solved.
Some of the proposals for improved productivity by decreasing a polymerization/molding time include use of acrylates or thioacrylates containing a bromine atom or a sulfur atom for radical polymerization initiated by being irradiated with light to obtain optical lenses, as disclosed by Japanese Patent Laid-open Publication Nos. 63-248811, 1-266613 and 3-217412. Moreover, use of (meth)acrylate compounds having a sulfur-containing alicyclic structure as a radical-polymerizable compound is also suggested for production of the optical lenses by Japanese Patent Laid-open Publication Nos. 3-215801 and 4-161410.
However, the resins produced, by these methods, although being able to be polymerized in a shorter time, rarely satisfy characteristics sufficient for optical lenses, which include optical characteristics (e.g., transparency, refractive index and Abbe number), thermal characteristics (e.g., thermal deformation temperature) and mechanical characteristics (e.g., impact resistance and bending strength). More specifically, when these resins are used for spectacles lenses, they have various disadvantages of, e.g., insufficient refractive index, low Abbe number though being high in refractive index, being fragile and easily broken, and being heavy for the lenses, and in addition, the surfaces of the resins are roughened or attacked by a solvent which is used for treatment, e.g., for providing a hard coat. Therefore, developments of the materials which can solve these problems have been greatly demanded.
As described above, each of the conventional optical resins involves disadvantages and problems to be solved, though having excellent characteristics. Under these circumstances, there are keen demands for development of novel optical materials which are excellent in productivity because of being polymerizable and moldable in a short time, good in thermal and mechanical characteristics, and high in refractive index and Abbe number.
DISCLOSURE OF THE INVENTION
It is an object of the present invention to provide an optical resin, which can be polymerizable and moldable in a short time so that it is excellent in productivity, having good thermal and mechanical characteristics, and being high in refractive index by solving the problems involved in the conventional optical resin.
The present inventors have achieved the present invention after having extensively studied to solve the above-described problems. That is, the present invention provides:
[1] An acrylic ester compound represented by formula (1):
(wherein
“a”, is an integer of 0 to 4;
R
1
is a directly bonded single bond, an alkylene group which may have a substituent, an aralkylene group which may have a substituent, an arylene group which may have a substituent, or a —Y
3
—S—R
4
—S—Y
4
— group;
R
2
and R
3
are each a hydrogen atom or an alkyl group;
X
1
and X
2
are each an oxygen atom or a sulfur atom;
Y
1
and Y
2
are each an alkylene group which may contain an oxygen atom or a sulfur atom;
R
4
in the —Y
3
—S—R
4
—S—Y
4
— group is an alkylene group, an aralkylene group or an arylene group; and
Y
3
and Y
4
in the —Y
3
—S—R
4
—S—Y
4
— group are each independently an alkylene group.
[2] The acrylic ester compound according to [1], wherein in formula (1), “a” is 1; R
1
is a directly bonded single bond, an alkylene group which may have a substituent, an aralkylene group which may have a substituent, an arylene group which may have a substituent or a —Y
3
—S—R
4
—S—Y
4
— group (wherein Y
3
is a —(CH
2
)
m
— group and Y
4
is a —(CH
2
)
n
— group (“m” and “n” are each an integer of 1 to 4)); and Y
1
is a —(CH
2
)
k
— group and Y
2
is a —(CH
2
)
1
— group (“k” and “l” are each an integer of 1 to 4).
[3] The acrylic ester compound according to [1], wherein in formula (1), “a” is 0; and Y
1
is a —(CH
2
)
k
— group and Y
2
is a —(CH
2
)
1
— group (“k” and “l” are each an integer of 1 to 4).
[4] The acrylic ester compound according to [2], wherein the compound represented by formula (1) is represented by formula (1-a):
(wherein R
5
, which is similar to R
1
, is a directly bonded single bond, an alkylene group which may have a substituent, an aralkylene group which may have a substituent, or an arylene group which may have a substituent; and R
2
, R
3
, X
1
, X
2
, “k” and “l” are same meanings as described above).
[5] The acrylic ester compound according to [2], wherein the compound represented by formula (1) is a compound represented by formula (1-b):
(wherein R
2
, R
3
, R
4
, X
1
, X
2
, “k”, “l”, “m” and “n” are same meanings as described above).
[6] The acrylic ester compound according to [3], wherein the compound represented by formula (1) is a

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