Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
2002-09-03
2004-05-18
Hightower, P. Hampton (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S125000, C528S126000, C528S128000, C528S172000, C528S173000, C528S174000, C528S176000, C528S179000, C528S183000, C528S185000, C528S188000, C528S220000, C528S229000, C528S351000
Reexamination Certificate
active
06737503
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a novel diamine and its polyimide. More particularly, the invention relates to a novel aromatic diamine and its polyimide which is suitable for low-temperature adhesive bonding.
BACKGROUND OF THE INVENTION
Polyimides are excellent in heat resistance, chemical resistance, mechanical strength, electric properties, etc., and by utilizing these excellent properties, they have been widely used in various technical fields such as aircraft field and electronic field.
As to polyimides for adhesive bonding, heat-resistant adhesive polyimides containing 3,3′-diaminobenzophenone or 1,3-bis(3-aminophenoxy)benzene (abbreviated to APB hereinafter) as a diamine component are disclosed in U.S. Pat. No. 4,065,345 and Japanese Patent Laid-Open Publication No. 143477/1986. Although these polyimides have excellent heat resistance and adhesion properties, they have a problem that their adhesion temperatures need to be set to high temperatures in order to exhibit favorable adhesion.
In Japanese Patent Laid-Open Publication No. 73338/1994 and Japanese Patent Laid-Open Publication No. 322928/1999, polyimides having a siloxane bond or aliphatic units in the polymer as a main chain are disclosed. Although these polyimides have a relatively low glass transition temperature (Tg) advantageous in the adhesion properties, they contain many aliphatic units, whereby not only heat resistance, a feature of polyimide, is lowered but also adhesion properties are deteriorated.
OBJECT OF THE INVENTION
It is an object of the present invention to provide a novel polyimide that exhibits excellent adhesion properties and adhesive strength at an adhesion temperature lower than that of the conventional polyimides.
It is another object of the invention to provide a diamine suitable as a starting material for the preparation of the polyimide.
SUMMARY OF THE INVENTION
The present inventors have earnestly studied to solve the above problems. As a result, they have found that an aromatic diamine can be prepared by allowing an aromatic dihalogen compound such as an aromatic difluoro compound represented by the formula (3) to react with an aminophenol derivative, and also have found a novel aromatic diamine represented by the formula (1) which has various substitution positions.
The present inventors have further found that a polyimide containing the above diamine as a constituent exhibits excellent adhesion properties and adhesive strength at a low adhesion temperature.
That is to say, the present invention relates to:
(1) an aromatic diamine compound represented by the formula (1):
wherein n is an integer of 3 to 7, each R is independently an atom or a group selected from the group consisting of a hydrogen atom, a halogen atom and a hydrocarbon group, the same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on at least one benzene ring, and when n is 3, the hetero atoms are at the ortho- or meta-positions to each other on all the benzene rings;
(2) an aromatic difluoro compound represented by the formula (3):
wherein n is an integer of 3 to 7, and each R is independently an atom or a group selected from the group consisting of a hydrogen atom, a halogen atom and a hydrocarbon group; and
(3) a polyimide having a repeating unit represented by the formula (4):
wherein Y is a tetravalent organic group, n is an integer of 3 to 7, each R is independently an atom or a group selected from the group consisting of a hydrogen atom, a halogen atom and a hydrocarbon group, the same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on at least one benzene ring, and when n is 3, the hetero atoms are at the ortho- or meta-positions to each other on all the benzene rings.
DETAILED DESCRIPTION OF THE INVENTION
Aromatic Diamine Compound
The aromatic diamine compound of the invention is represented by the following formula (1).
In the formula (1), n is an integer of 3 to 7, preferably an integer of 3 to 5. Each R is independently an atom or a group selected from the group consisting of a hydrogen atom, a halogen atom and a hydrocarbon group. The same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on at least one benzene ring. When n is 3, the hetero atoms are at the ortho- or meta-positions to each other on all the benzene rings.
Examples of the halogen atoms indicated by R in the formula (1) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the hydrocarbon groups indicated by R include a lower alkyl group, a lower alkenyl group, an aralkyl group and an aryl group.
The lower alkyl group is a straight-chain, branched or cyclic alkyl group of 1 to 8 carbon atoms, and examples of such alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
The lower alkenyl group is a straight-chain or branched alkenyl group of 2 to 6 carbon atoms, and examples of such alkenyl groups include vinyl, allyl, isopropenyl, 4-pentenyl and 5-hexenyl.
The aralkyl group is an aralkyl group of 7 to 15 carbon atoms, and examples of such aralkyl groups include benzyl, phenethyl, benzhydryl and phenylpropyl.
The aryl group is an aryl group of 6 to 15 carbon atoms, and examples of such aryl groups include phenyl, tolyl, xylyl and naphthyl.
The aromatic diamine compound is preferably one wherein R in the formula (1) is a hydrogen atom. More specifically, an aromatic diamine compound represented by the following formula (7) or (8) is preferable.
In the formula (7), the same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on all the benzene rings.
In the formula (8), the same or different two hetero atoms selected from nitrogen atoms and oxygen atoms bonded to each benzene ring are at the ortho- or meta-positions to each other on at least one benzene ring.
The compound represented by the formula (1) is also preferably an aromatic diamine compound represented by the formula (2).
wherein R and n are as defined in the formula (1).
Examples of the aromatic diamine compounds represented by the formula (1) are given below.
That is to say, there can be mentioned the following compounds without limiting thereto;
1,3-bis(3-(3-aminophenoxy)phenoxy)benzene,
1,3-bis(3-(2-aminophenoxy)phenoxy)benzene,
1,3-bis(2-(2-aminophenoxy)phenoxy)benzene,
1,3-bis(2-(3-aminophenoxy)phenoxy)benzene,
1,2-bis(3-(3-aminophenoxy)phenoxy)benzene,
1,2-bis(3-(2-aminophenoxy)phenoxy)benzene,
1,2-bis(2-(2-aminophenoxy)phenoxy)benzene,
1,2-bis(2-(3-aminophenoxy)phenoxy)benzene,
1,3-bis(3-(3-aminophenoxy)phenoxy)-2-methylbenzene,
1,3-bis(3-(2-aminophenoxy)phenoxy)-5-sec-butylbenzene,
1,3-bis(2-(2-amino-6-ethylphenoxy)phenoxy)benzene,
1,3-bis(2-(3-aminophenoxy)-4-methylphenoxy)benzene,
1,2-bis(3-(3-aminophenoxy)phenoxy)-4-methylbenzene,
1,2-bis(3-(2-amino-3-propylphenoxy)phenoxy)benzene,
1,3-bis(3-(3-aminophenoxy)phenoxy)-2-chlorobenzene,
1,3-bis(3-(2-aminophenoxy)phenoxy)-5-bromobenzene,
1,3-bis(2-(2-amino-6-chlorophenoxy)phenoxy)benzene,
bis(3-(3-(3-aminophenoxy)phenoxy)phenyl) ether,
bis(3-(3-(2-aminophenoxy)phenoxy)phenyl) ether,
bis(3-(3-(4-aminophenoxy)phenoxy)phenyl) ether,
bis(4-(3-(3-aminophenoxy)phenoxy)phenyl) ether,
bis(2-(3-(3-aminophenoxy)phenoxy)phenyl) ether,
bis(4-(3-(2-aminophenoxy)phenoxy)phenyl) ether,
bis(4-(2-(2-aminophenoxy)phenoxy)phenyl) ether,
bis(2-(2-(3-aminophenoxy)phenoxy)phenyl) ether,
bis(2-(4-(3-aminophenoxy)phenoxy)phenyl) ether,
bis(2-(2-(4-aminophenoxy)phenoxy)phenyl) ether,
bis(2-(2-(2-aminophenoxy)phenoxy)phenyl) ether,
bis(2-(4-(2-aminophenoxy)phenoxy)phenyl) ether,
bis(4-(2-(3-aminophenoxy)phenoxy)p
Kawaguchi Masaru
Kodama Yoichi
Mori Minehiro
Nagai Naoshi
Burns Doane , Swecker, Mathis LLP
Hampton Hightower P.
Mitsui Chemicals Inc.
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