Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2000-09-27
2001-07-03
Shah, Mukund J. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C549S510000, C252S182130, C252S405000
Reexamination Certificate
active
06255484
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a cyanurate compound containing three oxetane ring groups and an organic hardening composition containing the same. More particularly, the present invention relates to a photosetting or thermosetting cyanurate compound containing three oxetane ring groups, and an organic hardening composition containing the same.
The compounds having oxetane ring groups are photosetting or thermosetting monomers. The resins derived from the oxetane ring group-containing compounds generally exhibit excellent heat resistance, mechanical properties and adhesiveness. Thus, the oxetane ring group-containing compounds are useful as materials for shaped articles such as, for example, parts of electric devices, heat-resistant resists, coating materials and adhesives and as cross-linking agents and modifying agents for powder coating materials.
2. Description of the Related Art
Compounds containing oxetane ring groups (which will be referred to as oxetane compounds hereinafter) currently draw attention as cationically polymerizable monomers. Thus, various types of mono-functional or poly-functional oxetane compounds, for example, shown below have been reported.
(a) Pure Appl. Chem., A30 (2 &3), pp.189-206 (1993) discloses methods of synthesizing various oxetane compounds.
(b) DE Patent No. 1,021,858 discloses an oxetane compound represented by the formula (a):
wherein R
2
represents an alkyl, aryl, aralkyl, cycloalkyl or di- or valent aromatic group; Et represents an ethyl group; and k represents an integer of 1 or 2.
(c) Japanese Unexamined Patent Publication No. 6-1.6804 discloses an oxetane compound of the formula (b):
wherein R
3
represents a hydrogen or fluorine atom, or an alkyl group with 1 to 6 carbon atoms, a fluoroalkyl group with 1 to 6 carbon atoms, an alkyl group, an aryl group, or a thienyl group; R
4
represents a multi-valent organic group selected from straight or branched chain poly (alkyleneoxy) groups, xylylene group, siloxane bond groups and ester bond groups; Z represents a oxygen or sulfur atom; and m represents an integer of 2 to 4.
(d) Japanese Unexamined Patent Publication No. 8-245,783 discloses a plurality of oxetane compounds, for example, di-functional oxetane compounds having a 2,2′-bitolylenediyl skeleton.
(e) Japanese Unexamined Patent Publication No. 9-309,950 and No. 10-212,343 disclose oxetane compounds of the formula (c):
wherein p represents an integer of 1 to 4;
R
5
represents a hydrogen or fluorine atom or an alkyl group with 1 to 6 carbon atoms, an alkyl group, an aralkyl group, an aryl group, a furyl group or a thienyl group; R
6
represents a hydrogen-atom when p is 1, or an organic group having a valence corresponding to the integer represented by p when p is 1 to 6; Z represents an oxygen or sulfur atom.
When the oxetane compounds are utilized as components of thermosetting resin compositions, the resultant thermoset resins are unsatisfactory in the heat resistance thereof. Particularly, in the field of the electronic materials, for example, resists, there is a strong demand for new type of oxetane compounds capable of forming thermosetting resin materials having excellent heat resistance.
In the prior art, no cyanuric acid derivatives having the oxetane ring groups and no synthetic methods for preparing the compounds were known.
Also, no organic hardening composition containing, as a hardening component, a cyanurate compound having the oxetane ring group was known before the present invention.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a cyanurate compound having three oxetane ring groups which can be produced from available starting materials, and an organic hardening composition comprising, as a hardening component, the above-mentioned cyanurate compound.
Another object of the present invention is to provide a cyanurate compound having three oxetane ring groups which can be converted to a hardened product having excellent heat resistance and useful as a material, for example, a resist, for the electronic material field, and an organic hardening composition comprising, as a hardening component, the above-mentioned cyanurate compound.
The above-mentioned objects can be attained by the cyanurate compound of the present invention, having three oxetane ring groups and represented by the general formula (1):
wherein R
1
represents a member selected from the group consisting of a hydrogen atom and alkyl groups having 1 to 6 carbon atoms.
In the oxetane ring group-containing cyanurate compound of the present invention, in the formula (1), R
1
preferably represents a member selected from the group consisting of methyl and ethyl group.
The oxetane ring group-containing cyanurate compound, of the present invention, may comprise a reaction product of a 3-hydroxymethyloxetane compound, represented by the formula (2):
wherein R
1
is as defined above, with cyanuric chloride of the formula (3):
in the presence of a basic substance.
The oxetane ring group-containing cyanurate compound of the present invention may comprising a reaction product of an alkali metal alcoholate of a 3-hydroxymethyloxetane compound of the formula (2):
wherein R
1
is as defined above, with cyanuric chloride of the formula (3):
Also, the above-mentioned objects can be attained by the organic hardening composition of the present invention comprising, as a hardening component (A), at least one cyanurate compound having three oxetane ring groups, as defined above.
In the organic hardening composition of the present invention, the component (A) consisting of the oxetane ring group-containing cyanurate compound may be mixed with a hardening agent component (B) consisting of at least one polycarboxylic anhydride and a catalyst component (C).
In the organic hardening composition of the present invention, the polycarboxylic anhydride for the hardening agent component (B) may be selected from the group consisting of cycloaliphatic polycarboxylic anhydrides, aromatic polycarboxylic anhydrides and aliphatic polycarboxylic anhydrides.
In the organic hardening composition of the present invention, the hardening agent component (B) may be present in an equivalent amount of 0.7 to 1.0 times the equivalent amount of the oxetane ring in the oxetane ring group-containing cyanurate compound in the hardening component (A).
In the organic hardening composition of the present invention, the catalyst component (C) may comprises at least one member selected from amine compounds, metal carboxylates, protonic acids and tetra-alkoxytitaniums.
In the organic hardening composition of the present invention, the catalyst component (C) may be present in an equivalent amount corresponding to 1.0 to 7.0% of the equivalent amount of the oxetane ring groups of the oxetane ring group-containing cyanurate compound contained in the hardening component (A).
The organic hardening composition of the present invention optionally comprises at least one additional component (D) selected from the group consisting of hydroxyl group-containing compounds and epoxy compounds.
In the organic hardening composition of the present invention, the hydroxyl group-containing compounds for the additional component (D) may be selected from the group consisting of water, aliphatic monohydric alcohols having 1 to 12 carbon atoms and aliphatic polyhydric alcohols having 2 to 10 carbon atoms.
The organic hardening composition of the present invention optionally comprises a further additional component (E) comprising at least one epoxy compound.
In the organic hardening composition of the present invention, the epoxy compounds for the further additional component (E) may be selected from the group consisting of aromatic epoxy compounds, and cycloaliphatic epoxy compounds.
The organic hardening composition as mentioned above can be hardened to provide a hardened product.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The cyanurate compound of the general formula (1) of the present invention has three oxetane ring groups, non-subst
Hoshino Harutoshi
Kashima Mikito
Machida Toshikazu
Noda Yumiki
Balasubramanian Venkataraman
Burgess, Ryan & Wayne
Moran William R.
Shah Mukund J.
Ube Industries Ltd.
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