Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2001-08-10
2003-05-27
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S150000, C522S151000, C522S173000, C428S208000, C106S287300, C106S287320, C264S494000, C264S001100, C264S001270, C264S001320, C264S001340, C264S001310
Reexamination Certificate
active
06569916
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a triazine type monomer, and more particularly, to a 1,3,5-triazine type monomer expressed in the following formula (I) characterized by having at least one amine group and at least two sulfur atoms. The triazine monomers can be used in manufacturing transparent optical resin having excellent refractive index, surface hardness and light transparency as well as an improved workability and the ability to control a wide range of refractive index by adjusting composition by the monomer itself at room temperature or by polymerizing the monomer with a comonomer in the presence of an organic solvent or an initiator.
BACKGROUND OF THE INVENTION
Plastic transparent optical materials have been welcomed as matrices for manufacturing optical lenses, optical filters and transparent panels because they are light-weighted, less fragile and also more easily dyeable as compared to inorganic materials. In particular, the importance of developing plastics having high surface hardness and high refractive index has been much emphasized lately since the massive introduction of diethylene glycol biscarbonate allyl(CR-39) compounds in production of optical lens. However, CR-39 has a relatively low refractive index of below 1.50 even after curing process and thus the central region of the lens to be manufactured has to be thick in case of a convex lens while the periphery has to be thick in a concave lens thus resulting in production of heavy lenses.
Many lines of studies to develop monomers with high refractive index have been initiated since 1986. Various types of monomers including an alkyl- and meta-alkyl group were developed in 1990s, thus improving the refractive index of lenses to some extent. Nevertheless, the refractive index of those monomers were n
b
20
: 1.526-1.519 and the refractive index of the resulting lenses produced accordingly was approximately n
D
25
: 1.549. Therefore, the development of monomers having refractive index of higher than 1.55 still remains as a long-felt need.
Monomers having high refractive index can shorten the focal distance of given lenses and thus produce thin lenses; hence, they can be widely used in manufacturing optical lenses, transparent panels, optical heads and other light-weighted optical products. Polycarbonates, being a transparent optical resin, have rather high refractive index of 1.59, however, they have a few drawbacks that they are deficient in optical homogeneity and have poor anti-solvent and abrasion resistance properties thus not being suitable for manufacturing optical products requiring high transparency and high surface hardness.
To resolve the above problems, compounds with high refractive index containing an aromatic ring, thiol or a halogen group in the molecule have been developed. Recently, polyurethanes were developed to increase both the refractive index and the Abbe number. However, these polyurethanes are also not recommended because they would impede hard coating and multi-coating and also result in relatively low lens production yield due to their poor thermal stability and low surface hardness.
Japanese Patent Publication 11-263811 discloses a method of preparing a curing composition with good workability to give a cured product, consisting of a cyanuric acid or an isocyanuric acid, with excellent optical properties and impact resistance. However, the cured product has refractive index of about 1.575, which is lower than the refractive index of lenses manufactured using polyurethanes. Therefore the development of monomers with excellent thermal stability, surface hardness and high refractive index as well as processability with other monomers is still highly required.
SUMMARY OF THE INVENTION
The inventors of the present invention developed a method to prepare a triazine-containing monomer as expressed in the formula (I) with refractive index higher than 1.6 and the optical products manufactured from the monomer were shown to have excellent physical properties with respect to transparency, refractive index, surface hardness and thermal stability. Therefore, the object of this invention is to provide a monomer and a composition containing this monomer which can be effectively used in optical industry such as manufacturing functional optical lenses, optical filters, optical displayers, optical discs or optical heads and other optical devices.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a triazine type monomer, and more particularly, to a 1,3,5-triazine type monomer expressed in the following formula I characterized by having at least one amine group and at least two sulfur atoms
wherein R
1
is a secondary or a tertiary amine group selected from the group consisting of R
4
NH—, R
4
R
5
N— or
R
4
and R
5
are independently C
1
-C
22
alkyl or cycloalkyl; R
6
is a C
1
-C
15
alkylene or aromatic ring forming alkenes such as —CH═CH—CH═CH— or —CH═CH—CH
2
—CH═CH—; R
2
is C
1
-C
22
linear alkylene, branched alkylene, or a 1,3-,1,4-benzene ring; R
3
is R
1
or —S—( R
2
—S)
n
—X; X is an acryl-, methacryl or C
2
-C
10
alkene group; and n is an integer of 1-10.
The method of preparing the above triazine type monomer used in the present comprises the following steps of:
(a) preparing triazine expressed in the following formula (IV) by reacting 2,4,6-trichloro-1,3,5-triazine with secondary- or tertiary amine;
(b) preparing triazine expressed in the following formula (V) by reacting said triazine obtained in the above step (a) with NaSH;
(c) preparing triazine expressed in the following formula (VI) by reacting said triazine obtained in the above step (b) with a thiol derivative expressed as Y—(R
2
—S)
n
—H in the presence of a mixed catalyst; and
(d) preparing triazine expressed in the above formula (I) by reacting said triazine obtained in the above step (c) with;
(i) a compound selected from a group consisting of acryloyl chloride, methacryloyl chloride, and allyl bromide in the presence of a mixed catalyst; or
(ii) propionyl chloride and then treat with a base,
wherein R
1
is a secondary or a tertiary amine group selected from the group consisting of R
4
NH—, R
4
R
5
N— or
R
4
and R
5
are independents C
1
-C
22
alkyl or cycloalkyl; R
6
is C
1
-C
15
alkylene or an aromatic ring forming alkenes such as —CH═CH—CH═CH— or —CH═CH—CH
2
—CH═CH—; R
7
is the same as R
1
or Cl; R
8
is the same as R
1
or SH; R
9
is the same as R
1
or S—(R
2
—S)
n
—H; R
2
is C
1
-C
22
linear alkylene, branched alkylene, or a 1,3-,1,4-benzene ring; R
3
is R
1
or —S—( R
2
—S)
n
—X; X is an acryl-, methacryl or C
2
-C
10
alkene group; n is an integer of 1-10; and Y is a leaving group selected from Cl, Br and OH. Thus obtained triazine monomers of the present invention can be used to manufacture transparent optical products via self-polymerization of these monomers or copolymerization in the presence of comonomer(s). The overall physical properties of the optical products such as refractive index can be adjusted by preparing the polymerizable resin composition so that it comprises 1-98 wt % of the monomer of the present invention; 1-98 wt % of either an aromatic radical polymerizable monomer or a comonomer with an unsaturated group; and 0.5-5 wt % of an initiator.
The methods of manufacturing of plastic products using the above composition can include various procedural methods such as thermosetting of the resin composition at 10-130° C., radiation curing of the resin composition at 10-130° C., or first radiation curing the resin composition at 10-130° C. followed by thermo setting of the resin composition at 10-130° C.
The present invention is explained in greater detail by means of the methods of manufacturing a triazine type monomer with high refractive index.
The novel triazine type monomers are manufactured by the reactions shown below, wherein polymerizable triazine type monomers with high refractive index expressed in the formula I are manufactured by the method comprising steps of substitution of at le
Korea Research Institute of Chemical Technology
McClendon Sanza L.
Seidleck James J.
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