Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2002-01-09
2004-04-06
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S126000, C528S220000, C528S488000, C528S492000, C528S501000, C528S503000, C525S310000, C525S471000, C525S534000
Reexamination Certificate
active
06716956
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention is directed to improved processes for making polyarylene ether compounds. More specifically, the present invention is directed to a process for preparing polyarylene ether compounds wherein the molecular weight of the product is well controlled. One embodiment of the present invention is directed to a process for preparing a polymer of the formula
wherein x is an integer of 0 or 1, a is an integer of from 1 to 5, R′ is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, or a mixture thereof, A is
wherein R is a hydrogen atom, an alkyl group, an aryl group, or mixtures thereof,
or mixtures thereof, B is
&Parenopenst;CH
2
&Parenclosest;
v
wherein v is an integer of from 1 to about 20,
—(CH
2
O)
t
—
wherein t is an integer of from 1 to about 20,
wherein z is an integer of from 2 to about 20,
wherein u is an integer of from 1 to about 20,
wherein w is an integer of from 1 to about 20,
wherein R
1
and R
2
each, independently of the other, are hydrogen atoms, alkyl groups, aryl groups, or mixtures thereof, and p is an integer of 0 or 1,
wherein b is an integer of 0 or 1,
wherein (1) Z is
—Ar-(X)
c
-Ar—
wherein c is 0 or 1; (2) Ar is
(3) G is an alkyl group selected from alkyl or isoalkyl groups containing from about 2 to about 10 carbon atoms; (4) Ar′ is
(5) X is
wherein s is 0, 1, or 2,
and (6) q is 0 or 1; or mixtures thereof, and n is an integer representing the number of repeating monomer units, said process comprising (A) providing a reaction mixture which comprises (i) a solvent, (ii) a compound of the formula
(iii) a compound of the formula
(iv) a compound of the formula
wherein a is an integer of from 1 to 5 and R′ is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, or a mixture thereof, and (v) a carbonate base; and (B) heating the reaction mixture and removing generated water from the reaction mixture, thereby effecting a polymerization reaction.
Polyarylene ethers are known polymers for use as high performance engineering thermoplastics. They exhibit outstanding physical properties and high chemical resistance. The use of these materials as photoresists when substituted with photoactive substituents is also known.
While polyarylene ethers are well known compounds, only a few examples of these materials are commercially available. Commercially available materials tend to be polymers of high molecular weight. Some applications for polyarylene ethers, however, such as ultra-thin films, photoresists, and the like, can be better carried out with polymers of lower molecular weight and/or lower solution viscosity.
U.S. Pat. No. 5,994,425 (Narang et al.), U.S. Pat. No. 6,022,095 (Narang et al.), EP 827027, and JP 10120743, the disclosures of each of which are totally incorporated herein by reference, disclose an improved composition comprising a photopatternable polymer containing at least some monomer repeat units with photosensitivity-imparting substituents, said photopatternable polymer being of the general formula
wherein x is an integer of 0 or 1, A is one of several specified groups, such as
B is one of several specified groups, such as
or mixtures thereof, and n is an integer representing the number of repeating monomer units. Also disclosed is a process for preparing a thermal ink jet printhead with the aforementioned polymer and a thermal ink jet printhead containing therein a layer of a crosslinked or chain extended polymer of the above formula.
U.S. Pat. No. 5,849,809 (Narang et al.), U.S. Pat. No. 6,203,143 (Narang et al.), EP 827028, and JP 10090895, the disclosures of each of which are totally incorporated herein by reference, disclose a composition which comprises (a) a polymer containing at least some monomer repeat units with photosensitivity-imparting substituents which enable crosslinking or chain extension of the polymer upon exposure to actinic radiation, said polymer being of the formula
wherein x is an integer of 0 or 1, A is one of several specified groups, such as
B is one of several specified groups, such as
or mixtures thereof, and n is an integer representing the number of repeating monomer units, wherein said photosensitivity-imparting substituents are hydroxyalkyl groups; (b) at least one member selected from the group consisting of photoinitiators and sensitizers; and (c) an optional solvent. Also disclosed are processes for preparing the above polymers and methods of preparing thermal ink jet printheads containing the above polymers.
U.S. Pat. No. 6,124,372 (Smith et al.), U.S. Pat. No. 6,151,042 (Smith et al.), U.S. Pat. No. 6,323,301 (Smith et al.), EP 827029, and JP 10097073, the disclosures of each of which are totally incorporated herein by reference, disclose a composition comprising a polymer with a weight average molecular weight of from about 1,000 to about 100,000, said polymer containing at least some monomer repeat units with a first, photosensitivity-imparting substituent which enables crosslinking or chain extension of the polymer upon exposure to actinic radiation, said polymer also containing a second, thermal sensitivity-imparting substituent which enables further crosslinking or chain extension of the polymer upon exposure to temperatures of about 140° C. and higher, wherein the first substituent is not the same as the second substituent, said polymer being selected from the group consisting of polysulfones, polyphenylenes, polyether sulfones, polyimides, polyamide imides, polyarylene ethers, polyphenylene sulfides, polyarylene ether ketones, phenoxy resins, polycarbonates, polyether imides, polyquinoxalines, polyquinolines, polybenzimidazoles, polybenzoxazoles, polybenzothiazoles, polyoxadiazoles, copolymers thereof, and mixtures thereof.
U.S. Pat. No. 5,889,077 (Fuller et al.), U.S. Pat. No. 6,087,414 (Fuller et al.), EP 827030, and JP 10090894, the disclosures of each of which are totally incorporated herein by reference, disclose a process which comprises reacting a polymer of the general formula
wherein x is an integer of 0 or 1, A is one of several specified groups, such as
B is one of several specified groups, such as
or mixtures thereof, and n is an integer representing the number of repeating monomer units, with (i) a formaldehyde source, and (ii) an unsaturated acid in the presence of an acid catalyst, thereby forming a curable polymer with unsaturated ester groups. Also disclosed is a process for preparing an ink jet printhead with the above polymer.
U.S. Pat. No. 5,739,254 (Fuller et al.), U.S. Pat. No. 5,753,783 (Fuller et al.), EP 826700, and JP 10087817, the disclosures of each of which are totally incorporated herein by reference, disclose a process which comprises reacting a polymer of the general formula
wherein x is an integer of 0 or 1, A is one of several specified groups, such as
B is one of several specified groups, such as
or mixtures thereof, and n is an integer representing the number of repeating monomer units, with an acetyl halide and dimethoxymethane in the presence of a halogen-containing Lewis acid catalyst and methanol, thereby forming a haloalkylated polymer. In a specific embodiment, the haloalkylated polymer is then reacted further to replace at least some of the haloalkyl groups with photosensitivity-imparting groups. Also disclosed is a process for preparing a thermal ink jet printhead with the aforementioned polymer.
U.S. Pat. No. 5,761,809 (Fuller et al.), EP 827026, and JP 10090896, the disclosures of each of which are totally incorporated herein by reference, disclose a process which comprises reacting a haloalkylated aromatic polymer with a material selected from the group consisting of unsaturated ester salts, alkoxide salts, alkylcarboxylate salts, and mixtures thereof, thereby forming a curable polymer h
Bender Timothy P.
Burt Richard A.
DeVisser Christine J.
Saban Marko D.
Smith Paul F.
Byorick Judith L.
Truong Duc
Xerox Corporation
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