Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From sulfur-containing reactant
Reexamination Certificate
1999-09-03
2001-11-20
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From sulfur-containing reactant
C528S106000, C528S109000, C525S115000, C525S135000, C525S150000, C525S328500
Reexamination Certificate
active
06320020
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a novel sulfur-containing (thio)ether (co)polymer and an optical element therewith. The sulfur-containing (thio)ether (co)polymer of this invention is a thermoplastic optical resin with excellent optical, mechanical and thermal properties, which can be prepared in a good productivity and is useful for optical elements such as an optical disk substrate; a liquid-crystal plastic substrate; various optical lenses including an eye-glass; and an LED sealing coat.
2. Description of the Prior Art
An essential property is transparency for an optical material. To date, various industrial resins with good transparency are known; for example, polymethyl methacrylate(PMMA), bisphenol-A-polycarbonate (Bis-A-PC), polystyrene (PS), methyl methacrylate-styrene copolymer (MS), styrene-acrylonitrile copolymer (SAN), poly(4-methylpentene-1) (TPX), polycycloolefin (COP), poly(diethyleneglycol bisallylcarbonate) (EGAC) and polythiourethane (PTU).
PMMA exhibits good transparency, weather resistance and moldability, but has drawbacks such as a lower refractive index (n
d
) of 1.49 and a higher water absorbency.
Bis-A-PC exhibits good transparency, heat resistance and impact resistance and a higher refractive index, but also exhibits a larger chromatic aberration, which limits its application.
PS and MS exhibit good moldability and transparency as well as a lower water absorbency and a higher refractive index, but exhibit lower impact resistance, weather resistance and heat resistance. They have been, therefore, rarely used as an optical resin in practice.
SAN is believed to have a relatively higher refractive index and well-balanced mechanical properties, but it is inadequately heat resistant (heat-distortion temperature: 80 to 90° C.) to be used as an optical resin.
TPX and COP exhibit good transparency, lower water absorbency and good heat resistance, but have drawbacks such as a lower refractive index (n
d
=1.47 to 1.53), lower impact resistance and lower gas barrier property.
EGAC is a thermosetting resin from diethyleneglycol bisallylcarbonate monomer, which is most frequently used for a general-purpose eyeglass. It exhibits good transparency, good heat resistance and a minimal chromatic aberration, but has drawbacks such as a lower refractive index (n
d
=1.50) and lower impact resistance.
PTU is a thermosetting resin prepared by reaction of a diisocyanate with a polythiol, which is most frequently used for a superhigh refractive index eyeglass. It is an excellent material with good transparency, good impact resistance, a higher refractive index and a lower chromatic aberration, but has only one drawback of a longer duration for thermal-polymerization molding (1 to 3 days); i.e., there is a problem in productivity.
As described above, optical resins of the prior art have good properties, but they have their specific problems to be solved. Thus, it has been earnestly desired to develop a thermoplastic optical resin with good optical, mechanical and thermal properties as well as a good productivity and a higher refractive index.
SUMMARY OF THE INVENTION
An objective of this invention is to provide a thermoplastic optical resin with good optical, mechanical and thermal properties as well as a good productivity and a higher refractive index.
We have intensely attempted to solve the problems, and thus have obtained a thermoplastic optical resin with good optical, mechanical and thermal properties as well as a good productivity and a higher refractive index.
This invention provides (1) a sulfur-containing (thio)ether (co)polymer comprising repetitive structural units represented by general formulas 1 and 2:
where A and B, which may be the same or different, are bivalent organic group; R
1
and R
2
are independently hydrogen or alkyl; X
1
to X
4
, which may be the same or different, are independently oxygen or sulfur; Y
1
and Y
2
, which may be the same or different, are independently halogen, hydroxy, —OR
3
or —SR
4
, in which R
3
is sulfur-containing alkyl, aryl, heterocycle or acyl optionally having a substituent other than SH; and R
4
is non-substituted or substituted alkyl, aryl, heterocycle or acyl although when at least one of X
1
to X
4
is sulfur, R
3
may not contain a sulfur atom; provided that —OR
3
and/or —SR
4
constitute 10 to 100% of the total of Y
1
+Y
2
.
This invention also provides (2) a sulfur-containing (thio)ether (co)polymer as described in the above (1) wherein A and/or B is non-substituted or substituted bivalent aromatic group.
This invention also provides (3) a sulfur-containing (thio)ether (co)polymer as described in the above (2) wherein A and B are bivalent aromatic groups represented by formulas 3 and 4, respectively:
where R, which may be the same or different, is hydrogen, halogen or alkyl; and Z
1
and Z
2
, which may be the same or different, are a single bond, —C(CH
3
)
2
—, —S— or —SO
2
— linking the two aromatic groups together.
This invention also provides (4) a sulfur-containing (thio)ether (co)polymer as described in the above (3) wherein R
3
is sulfur-containing alkyl, aryl, heterocycle or acyl containing at least two sulfur atoms or one sulfur atom when at least one of X
1
to X
4
is a sulfur atom; and R
4
is alkyl, aryl, heterocycle or acyl containing at least one sulfur atom.
This invention also provides (5) a sulfur-containing (thio)ether (co)polymer as described in the above (3) or (4) wherein Z
1
is —C(CH
3
)
2
—.
This invention also provides (6) a sulfur-containing (thio)ether (co)polymer as described in the above (5) wherein X
1
and X
2
are oxygen.
This invention also provides (7) a sulfur-containing (thio)ether (co)polymer as described in the above (5) wherein Z
1
is —C(CH
3
)
2
— and Z
2
is a single bond or —C(CH
3
)
2
—.
This invention also provides (8) a sulfur-containing (thio)ether (co)polymer as described in the above (7) wherein all of X
1
to X
4
are oxygen.
This invention also provides (9) a sulfur-containing (thio)ether (co)polymer as described in the above (3) or (4) wherein Z
1
is —S—.
This invention also provides (10) a sulfur-containing (thio)ether (co)polymer as described in the above (9) wherein X
1
and X
2
are sulfur.
This invention also provides (11) an optical element manufactured using a sulfur-containing (thio)ether (co)polymer as described in any of the above (1) to (3).
This invention also provides (12) a plastic lens manufactured using a sulfur-containing (thio)ether (co)polymer as described in any of the above (1) to (3).
A sulfur-containing (thio)ether (co)polymer herein refers to a polymer or copolymer essentially containing a sulfur atom whose principal backbone comprises ether and/or thioether bonds. Therefore, when the principal chain comprises an ether bond, a sulfur atom must be contained in the remaining part other than the ether-bond moiety in the principal backbone; for example, in a pendant group. On the contrary, when the principal backbone comprises a thioether bond, the remaining part other than the thioether-bond moiety in the principal backbone may not necessarily contain a sulfur atom.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The sulfur-containing (thio)ether (co)polymer of this invention is a novel (co)polymer comprising repetitive structural units represented by general formulas 1 and 2. It is a thermoplastic optical resin with good optical, mechanical and thermal properties as well as a good productivity and a higher refractive index, which is useful for optical elements such as an optical disk substrate; a liquid-crystal plastic substrate; various optical lenses including an eye-glass; and an LED sealing coat.
In the general formulas (1) and (2), A and B, which may be the same or different, are a bivalent organic group. A bivalent organic group herein is a bivalent aliphatic or aromatic group or a combination thereof. The organic group may have a substituent and a hetero atom such as nitrogen and sulfur. It preferably contains a sulfur atom for improving a refractive index.
A bivalent
Fujii Ken-ichi
Imai Masao
Otsuji Atsuo
Sugimoto Kenichi
Suzuki Rihoko
Burns Doane Swecker & Mathis L.L.P.
Mitsui Chemicals Inc.
Truong Duc
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