Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
2000-02-28
2001-01-30
Acquah, Samuel A. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
C528S180000, C528S181000, C528S185000, C528S189000, C528S190000, C528S192000, C528S194000, C528S277000, C528S280000, C528S300000, C528S302000, C528S306000, C528S307000, C528S308000, C528S308600, C524S081000, C524S403000, C524S413000, C524S425000, C524S436000, C430S109500, C430S110100, C430S137170
Reexamination Certificate
active
06180747
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention is generally directed to polyester resin compositions and process thereof, and more specifically, a branched polyester, especially useful as a toner binder, and which resulting toner can be selected for imaging and printing processes. In embodiments, the polyester of the present invention is comprised of a branched polyester resin of the Formula
wherein n and m represent randomly repeating segments, for example the segments in ( ) are not in a particular sequence or pattern, and more specifically, represent repeating segments of the polymer backbone and randomly distributed such that the repetitive sequence of the segments n and m do not follow any algorithm, and the number of n and m segments in the polymer backbone are each, for example, of from about 10 to about 10,000 (from about to about as used throughout includes, for example, all numbers in between, such as 11, 12, 25, 100, 1,000, 5,000, 7,000), X is an aliphatic group of for example, from about 2 to about 20 carbon atoms, an olefinic group of, for example, a vinylidene group, or an aromatic group of, for example, from about 6 to about 18 carbon atoms, Y is selected from the alkoxylated bisphenol A units illustrated as groups or radicals I, II and/or III, and wherein I, II and/or III comprise, for example, a mixture of I from about 60 to 90 percent of the mixture, II from about 1 to 30 percent of the mixture, and III from about 0 to about 10 percent of the mixture; Z is selected from the branching units (p) illustrated as radicals or groups IV and V, and wherein R and R
1
are a hydrogen atom or aliphatic hydrocarbon, such as alkyl with from about 1 to about 20 carbon atoms, and (a) is preferably, for example, 0 or 1.
In a specific embodiment of the present invention, the branched polyester resin is derived from the polycondensation reaction of an equivalent of a diacid monomer, such as for example, fumaric acid or terephthalic acid, and an equivalent mixture of bis-alkoxylated bisphenol A with a hydroxyl number of from about 2 to about 4 illustrated herein by Formulas IX, X, XI, XII and XIII.
In another embodiment of the present invention, there is disclosed a process for the preparation of a mixture of bis-alkoxylated bisphenol A with a hydroxyl number of from about 2 to about 4 as illustrated by Formulas IX, X, XI, XII and XIII, involving the alkoxylation of bisphenol A with a cyclic alkylene carbonate in the presence of a catalyst, such as an alkali carbonate, and wherein the cyclic alkylene carbonate is, for example, an ethylene carbonate, propylene carbonate, butylene carbonate as illustrated by Formula VI, and a hydroxyl containing cyclic carbonate, such as glycerine carbonate and/or trimethylolpropane carbone, illustrated as VII and VIII, respectively.
wherein R
2
is a hydrogen, or an alkyl group.
PRIOR ART
Polyester resins are generally prepared by a polycondensation process involving the reaction of a diol monomer and a diacid or diester monomer, and producing water or an alcohol as byproduct, which is collected by distillation. Electrophotographic toners are generally comprised of a resin, such as a polyester, a pigment and optionally a charge control agent. Many various toner formulations are known, and more specifically, one known toner formulation is comprised of a crosslinked unsaturated polyester resin, such that desirable low fixing temperatures and offset properties are attained, reference, for example, U.S. Pat. No. 5,227,460, the disclosure of which is totally incorporated herein by reference, wherein there is disclosed as one preferred unsaturated polyester resin a poly(propoxylated bisphenol co-fumarate) which is crosslinked to a gel content of up to about 40 weight percent utilizing a peroxide to provide a toner useful for electrophotographic processes.
In U.S. Pat. No. 3,590,000, an unsaturated polyester for use as a toner binder is prepared from fumaric acid and a diphenol. Similarly, in U.S. Pat. No. 4,331,755, there is disclosed an unsaturated polyester resin derived from fumaric acid and a polyol blend of propoxylated bisphenol. Furthermore, in U.S. Pat. No. 4,314,049, a polyester resin composition is generated by the reaction of a dicarboxylic acid and a polylol comprising an etherified diphenol. Additionally, U.S. Pat. No. 4,525,445 discloses an unsaturated polyester resin derived from fumaric acid, isophthalic acid and a polyol blend of propoxylated bisphenol. These aforementioned unsaturated polyester resins can be utilized, for instance, as a toner binder, especially for xerographic copiers and printers.
In U.S. Pat. No. 4,960,664 there is disclosed a polyester resin derived from an unsaturated dicarboxylic acid, a polybasic carboxylic acid having not less than three carboxylic acid group and a diol component, in particular, an etherified bisphenol. In U.S. Pat. No. 4,804,622, there is disclosed a polyester resin formed by co-condensation of a diol component represented by an bis-alkoxylated bisphenol A structure, a dibasic carboxylic acid, and a tribasic or polybasic carboxylic acid, or trihydroxyl or polyhydroxylic alcohol. Furthermore, in U.S. Pat. No. 5,057,596 there is disclosed a crosslinked polyester resin comprised of a trihydric or higher alcohol or trivalent carboxylic acid, an alicyclic diol and an aromatic diacid. Additionally, in U.S. Pat. No. 5,015,724 there is disclosed a modified polyester produced by co-condensation of a dihydric alcohol, with a tri or higher valent carboxylic acid, and a tri or higher valent alcohol.
Other patents that may be of interest are U.S. Pat. Nos. 4,981,939; 4,049,477; 4,980,448; 4,217,440; 4,788,122; 5,466,554, 5,686,218; 4,988,794; 4,727,011; 4,533,614 and 5,366,841.
Although a number of the aforementioned polyester resins derived from alkoxylated bisphenol A, or etherified diphenol with fumaric acid are known, these resins are typically derived from an alkoxylated bisphenol A, which is derived, for example, from a mixture of monomers prepared by the anionic alkoxylation of bisphenol A with alkylene oxide in the presence of an alkali hydroxide catalyst in a pressurized vessel, and wherein the mixtures obtained, for example, are the alkali, such as sodium, potassium, salts of 4-(2-hydroxyalkyl)-bisphenol A, bis 4,4′-(2-hydroxyalkyl)-bisphenol A, and 4-(2′-hydroxyalkyl-2-oxyalkyl)-4′-(2-hydroxyalkyl)-bisphenol A.
SUMMARY OF THE INVENTION
It is a feature of the present invention to provide branched polyester resins.
Moreover, it is a feature of the present invention to provide a branched unsaturated polyester resin, especially useful as a xerographic toner binder.
It is another feature to provide a branched unsaturated resin derived from a diacid monomer, and a mixture of bis-alkoxylated bisphenol A with a hydroxyl number of from about 2 to about 4, illustrated herein as Formulas IX, X, XI, XII and XIII.
In yet another feature of the present invention there is provided a branched polyester resin useful as a toner binder, and which toner displays a glass transition of, for example, from about 52° C. to about 65° C., and a gel content of, for example, from about 1 to about 40 percent by weight of resin insoluble in toluene.
Moreover, it is a feature of the present invention to provide a branched unsaturated polyester resin derived from fumaric acid and a mixture of alkoxylated bisphenol A with a hydroxyl number of from about 2 to about 4, illustrated herein as IX, X, XI, XII and XII.
Furthermore, it is a feature of the present invention to provide a mixture of alkoxylated bisphenol A with a hydroxyl number of from about 2 to about 4 derived from bisphenol A and a mixture of alkylene carbonate and hydroxyalkylene carbonate, and polyesters wherein the branching component is a glycerine carbonate.
It is another feature of this invention to provide an economical process for the preparation of branched polyester resins, such as an unsaturated polyester resin, and which process comprises the alkoxylation of a diol, such as bisphenol A with an alkylene carbonate and hydroxyalkylene
Saban Marko D.
Sacripante Guerino G.
Toth Alan E. J.
Acquah Samuel A.
Palazzo E. O.
Xerox Corporation
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