Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
1999-11-09
2001-10-23
Hampton-Hightower, P. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S125000, C528S126000, C528S128000, C528S171000, C528S172000, C528S173000, C528S174000, C528S176000, C528S183000, C528S190000, C528S191000, C528S220000, C052S222000, C052S222000, C052S350000, C052S353000, C525S420000, C525S422000, C522S164000
Reexamination Certificate
active
06307002
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel polymide compositions and to processes for producing thereof. Particularly, the present invention relates to polyimide compositions having photosensitive groups such as cinnamoyl groups and chalcone groups and having both photoreactivity and thermoreactivity specific to a cinnamoyl group.
2. Description of Related Art
Polyimides have been widely used, for example, in the field of electronic communication and OA, appliances as well as in the field of aerospace because they have excellent heat resistance among a variety of organic polymers. In particular, the polyimides have recently been desired to have not only excellent heat resistance but also a variety of performance depending upon their purposes.
Photosensitive polymers can be obtained by a reaction of existing polymers and photosensitive groups functioning as pendant groups. The representative example of the photosensitive polymers prepared by this method is polyvinyl cinnamate invented by Minsk et al., Eastman Kodak Company, which is disclosed in J. Appl. Polymer Sci., 2, 302 (1959). Polyvinyl cinnamate is prepared by the esterification of polyvinyl alcohol using cinnanmic acid chloride. This polymer is irradiated with light to form cyclobutane rings to be crosslinked and cured.
Few polyimides have been known in which photosensitive groups such as cinnamoyl groups, coumarin groups and chalcone groups are directly jointed to their side chains. Furthermore, although such polyimides may be used as thermosetting resins because those photosensitive groups have double bonds, there have been few cases where polyimides are used as thermosetting resins by introducing a cinnamoyl group thereto.
SUMMARY OF THE INVENTION
The object of the present invention is to provide novel polyimide compositions having photosensitive groups and to provide processes for their preparation.
The present inventors have studied intensively and found that their intended objects can be achieved by compositions containing novel polyimides having specific structures, and as a result, they have accomplished the present invention.
A polyimide of the present invention is a polyimide represented by the following general formula (1):
wherein l, m, and n represent not the order of each repeating unit, but the numbers of each repeating unit existing in the molecule, and E
1
is a photosensitive group, E
2
is a group containing an alkyl group having 2 to 20 carbon atoms, —A(—E
1
)—, —A(—E
2
)— and B each represent a divalent organic group, X and Y each are a tetravalent organic group, X, Y, A, B, E
1
and E
2
may be identical or different among the repeating units when any one of l, m and n is 2 or more, l is an integer of 1 or more, m and n each are an integer of 0 or more.
In the general formula (1), E
1
may be at least one kind of photosensitive groups selected from the group consisting of cinnamic acid derivatives, cinnamylideneacetyl derivatives, chalcone derivatives, stilpyridine derivatives, furylacroyl derivatives, coumarin derivatives, pyrone derivatives and stilbene derivatives.
In the general formula (1), E
1
may be at least one kind of photosensitive groups selected from the following group (I):
wherein J represents H, CH
3
, CH
3
O, F, Cl, Br and I.
A polyimide composition of the present invention may contain 20 wt % or more of polyimide(s) selected from any one of polyimides described above.
A process of producing polyimide of the present invention is a process in which the polyimide of the general formula (1) is obtained by: synthesizing a copolymer represented by the following general formula (2)
wherein m and n represent not the order of each repeating unit, but the numbers of each repeating unit existing in the molecule, and X and Y each are a tetravalent organic group, A′ is a divalent organic group containing at least one hydroxyl group, B is a divalent organic group, X and Y may be identical or different among the repeating units when m is 2 or more, m is an integer of 1 or more, n is an integer of 0 or more; and subsequently introducing photosensitive groups and/or groups containing an alkyl group having 2 to 20 carbon atoms.
The present invention may be a process for producing a polyimide of the foregoing general formula (2), wherein —A′— represents
wherein
M represents H, CH
3
, CH
3
O, F, Cl, Br, and I;
D represents a single bond, —C(CF
3
)
2
—, —C(CH
3
)
2
—, —O—, —S—, —SO
2
—, —CH
2
—, and —CO—;
L represents —C
n
H
2n−2
(—OH)
2
—, —O—C
n
H
2n−2
(—OH)
2
—O—, —C
n
H
2n−1
(—OH)—, —O—C
n
H
2n−1
(—OH)—O—, and
p is an integer of 1 to 3; and
n is an integer of 1 to 20.
The present invention may be a process for producing a polyimide in which the polyimide of the general formula (1) is synthesized by reacting a diamine, to which a photosensitive group is introduced, with an acid dianhydride.
Furthermore, the present invention may be a process for producing a polyimide in which the polyimide of the general formula (1) is synthesized by reacting a diamine, to which a photosensitive group is introduced, and a diamine, to which a group containing an alkyl group having 2 to 20 carbon atoms is introduced, with an acid dianhydride.
As mentioned above, the polyimide compositions having photosensitive groups with photoreactivity specific to the photosensitive groups can be provided.
DESCRIPTION OF THE PREFERRED EMBODIMENT
A polyimide composition of the present invention contains a novel polyimide having photosensitive groups such as cinnamic acid, coumarin and chalcone, and having both photoreactivity and thermoreactivity specific to the photosensitive groups. Particularly, the polyimide of the present invention is represented by the general formula (1):
herein , m, and n represent not the order of each repeating unit, but the numbers of each repeating unit existing in the molecule, and E
1
is a photosensitive group, E
2
is a group containing an alkyl group having 2 to 20 carbon atoms, —A(—E
1
)—, —A(—E
2
)—, and B each represent a divalent organic group, X and Y each are a tetravalent organic group, X, Y, A, B, E
1
, and E
2
may be identical or different among the repeating units when any one of 1, m and n is 2 or more, l is an integer of 1 or more, m and Ii each are an integer of 0 or more.
A process of producing a novel polyimide and a polyimide composition of the present invention are described in detail below.
The polyimide of the general formula (1) of the present invention can be obtained by the following process.
{circle around (1)} There is formed first a polyamic acid, which is a precursor of the polyimide, represented by the general formula (3):
wherein m and n represent not the order of each repeating unit, but the numbers of each repeating unit existing in the molecule, and X and Y each are a tetravalent organic group, A′ is a divalent organic group containing at least one hydroxyl group, B is a divalent organic group, X and Y may be identical or different among the repeating units when m is 2 or more, m is an integer of 1 or more, n is an integer of 0 or more, wherein —A′— may be
wherein
M represents H, CH
3
, CH
3
O, F, Cl, Br and I;
D represents a single bond, —C(CF
3
)
2
—, —C(CH
3
)
2
—, —O—, —S—, —SO
2
—, —CH
2
— and —CO—;
L represents —C
n
H
2n−2
(—OH)
2
—, —O—C
n
H
2n−2
(—OH)
2
—O—, —C
n
H
2n−1
(—OH)—, —O—C
n
H
2n−1
(—OH)—O—, and
p is an integer of 1 to 3; and n is an integer of 1 to 20.
{circle around (2)} Subsequently, a polyimide represented by the general formula (2)
herein m and n represent not the order of each repeating unit, but the numbers of each repeating unit existing in the molecule, and X and Y each are a tetravalent organic groups, A′ is a divalent organic group containing at least one hydroxyl group, B is a divalent organic group, X and Y may be identical or different among the repeating units when m is 2 or more, m is an integer of 1 or more, n is an integer of 0 or more, is prepared by dehydration ring-closure of the polyamic acid
Nojiri Hitoshi
Okada Kohji
Hampton-Hightower P.
Kaneka Corporation
Pillsbury & Winthrop LLP
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