Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2002-01-29
2002-07-02
Ford, John M. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
active
06414146
ABSTRACT:
The present invention relates to a compound useful as a crosslinking agent for reactive molecules or reactive high polymer molecules, or an additive, and particularly the present invention relates to an isocyanurate compound having three 1,3-oxathiolane-2-thione rings in a molecule, which is suitably usable as an optical material having a high refractive index such as a plastic lens, an optical fiber or a functional film, and a starting material for a vulcanizing agent of rubber, an ink, a building sealing agent, a sealer or an adhesive agent, and also relates to a method for producing the same, and the present invention further relates to a trithiol isocyanurate compound obtained from the isocyanurate compound and a method for producing the same.
An organic high molecular material is light and easily processible, and therefore has been recently widely used as an optical material such as a plastic lens, an optical fiber or a functional film. However, as compared with an inorganic high molecular material, it has a low refractive index, which is one of important optical properties, and has a large chromatic aberration expressed by an Abbe number, and therefore it has a disadvantage that its use is limited.
On the other hand, an inorganic high molecular material has satisfactory performances in respect of heat resistance, mechanical property or chemical resistance and has a high refractive index, as compared with an organic high molecular material, but it has disadvantages that it is heavy and is not easily processible.
In the production of a conventional organic material having a high refractive index, it has been widely studied to introduce an aromatic ring, a halogen and sulfur in order to obtain a high refractive index. However, in case of introducing an aromatic ring into a structure, it is known that a double refraction is easily caused due to a high orientation property of an aromatic ring and that a transparency is degraded, and since an absorption wavelength of an aromatic ring resides relatively in the vicinity of a visible light part, an Abbe number becomes small and consequently there was a problem of providing a large chromatic aberration. This is caused by maximization of a refractive index in the vicinity of absorption wavelength, which is called as “abnormal dispersion”, and this is generally well known. Accordingly, it is necessary to produce a molecule containing no aromatic ring, but there have been not so many organic materials having a high refractive index but containing no aromatic ring.
Also, an inorganic high molecular material generally has a refractive index of from 1.46 to 1.92 and an Abbe number of from 25 to 80 in a wide range, but there is not known an organic high refractive index material having a refractive index of around 1.65 and having a large Abbe number of exceeding 40. An organic high refractive index material is desired to be designed so as to provide satisfactory properties by an appropriate combination in respect of an Abbe number and a refractive index, but there is a problem that a material having wide various optical properties is not available at present. Under the circumstances, it is desired to provide an organic high refractive index material having various optical properties in respect of a refractive index and an Abbe number, and it is therefore demanded by a market to provide a novel organic high refractive index material or its starting material.
In order to satisfy the above market's demand, the present invention provides a starting material for an organic high refractive index material having a high Abbe number without degrading a transparency, and a compound useful as a curing agent or a high molecular modifier. Particularly, the present invention provides a novel isocyanurate compound having three 1,3-oxathiolane-2-thione rings in a molecule and its production method as a first invention, and also provides a trithiol isocyanurate compound obtained from the isocyanurate compound and its production method as a second invention.
As the first invention, the first embodiment resides in an isocyanurate compound of the formula (1),
wherein R is a hydrogen atom or a methyl group.
The second embodiment resides in tris(l,3-oxathiolane-2-thion-5-ylmethyl)isocyanurate according to the first embodiment, wherein R in the formula (1) is a hydrogen atom.
The third embodiment resides in tris(5-methyl-1,3-oxathiolane-2-thion-5-ylmethyl)isocyanurate according to the first embodiment, wherein R in the formula (1) is a methyl group.
The fourth embodiment resides in a method for producing an isocyanurate compound of the formula (1),
wherein R is a hydrogen atom or a methyl group, which comprises reacting carbon disulfide with a triglycidyl isocyanurate compound of the formula (2),
wherein R is a hydrogen atom or a methyl group.
The fifth embodiment resides in the method for producing an isocyanurate compound according to the fourth embodiment, wherein the reaction of carbon disulfide with a triglycidyl isocyanurate compound is carried out in the presence of a catalyst of at least one compound selected from the group consisting of an alkali metal halide, an alkali earth metal halide, an organic base, an alkali metal hydroxide and an onium salt.
The sixth embodiment resides in the method for producing an isocyanurate compound according to the fourth or fifth embodiment, wherein the reaction of carbon disulfide with a triglycidyl isocyanurate compound is carried out by previously mixing carbon disulfide with a catalyst of at least one compound selected from the group consisting of an alkali metal halide, an alkali earth metal halide, an organic base, an alkali metal hydroxide and an onium salt and then adding the triglycidyl isocyanurate compound thereto.
As the second invention, the seventh embodiment resides in a trithiol isocyanurate compound obtained by reacting an isocyanurate compound of the formula (1),
wherein R is a hydrogen atom or a methyl group, with a compound having at least one functional group selected from the group consisting of an amino group, an imino group, a hydroxyl group and a thiol group.
The eighth embodiment resides in the trithiol isocyanurate compound according to the seventh embodiment, which is obtained by reacting an isocyanurate compound with a compound having at least one amino group.
The ninth embodiment resides in the trithiol isocyanurate compound according to the seventh or eighth embodiment, which is obtained by reacting an isocyanurate compound with a primary amine having a C
1
-C
6
alkyl group wherein the alkyl group may be substituted optionally with at least one different or same substituent selected from the group consisting of a C
1
-C
4
alkoxy group and a C
2
-C
8
dialkylamino group.
The tenth embodiment resides in the trithiol isocyanurate compound according to the seventh or eighth embodiment, which is obtained by reacting an isocyanurate compound with a benzylamine.
The eleventh embodiment resides in the trithiol isocyanurate compound according to the seventh or eighth embodiment, which is obtained by reacting an isocyanurate compound with a secondary benzylamine having a C
1
-C
6
alkyl group.
The twelfth embodiment resides in the trithiol isocyanurate compound according to the seventh or eighth embodiment, which is obtained by reacting an isocyanurate compound with a primary amine having a C
1
-C
6
alkenyl group.
The thirteenth embodiment resides in a method for producing a trithiol isocyanurate compound, which comprises reacting an isocyanurate compound of the formula (1),
wherein R is a hydrogen atom or a methyl group, with a compound having at least one functional group selected from the group consisting of an amino group, an imino group, a hydroxyl group and a thiol group.
The fourteenth embodiment resides in the method for producing a trithiol isocyanurate compound according to the thirteenth embodiment, which comprises reacting an isocyanurate compound with a compound having at least one amino group.
The fifteenth embodiment resides in the method for producing a trithiol isocy
Akimoto Kazuhiko
Hidaka Motohiko
Takeyama Toshiaki
Ford John M.
Nissan Chemical Industries Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
LandOfFree
Isocyanurate compound and method for producing the same does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Isocyanurate compound and method for producing the same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Isocyanurate compound and method for producing the same will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2867849