Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-07-29
2004-07-20
Trinh, Ba K. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C534S604000, C564S292000, C568S009000, C568S010000, C568S018000
Reexamination Certificate
active
06765102
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to novel compositions of matter. More particularly, it relates to cationic epoxy compounds that are water-soluble or water-dispersible and that contain both epoxy and organoonium functionalities. These compounds have utility in heat-sensitive compositions and imaging members such as lithographic printing plates.
BACKGROUND OF THE INVENTION
Epoxy resins represent a very broad class of organic materials that have been found useful in a variety of applications both as bulk materials in and of themselves, as components in composite materials, and as crosslinkers for various polymers. A complete discussion of this multi-billion dollar industry and the huge variety of the chemistry and products involving epoxy resins is provided in a very large amount of literature. See, for example, Flick, Ernest W.
Epoxy Resins, Curing Agents, Compounds, and Modifiers. An Industrial Guide
, Noyes Data Corp.: Park Ridge, N.J., 1987 and Bruins, Paul F.
Epoxy Resins Technology
, Interscience: New York, 1968.
Despite the large amount of available epoxy technology, the overwhelming majority of the uses of epoxy resins involve the preparation of an end product (a bulk material or a coating) that is mechanically tough, resistant to the elements, chemical resistant, and very hydrophobic. Thus, known epoxy resins have not found extensive use in hydrophilic environments in which a net hydrophilic, water-swellable, water-compatible, or readily wettable end product is required. Such uses include bio-compatible materials, aqueous separations media, coatings for lithographic printing plates, and photographic materials.
The current global trend of reducing the amounts of volatile organic compounds permitted in industrial emissions has fueled a continuing interest in the development of useful technology for aqueous-based formulations and coatings for many uses including lithography or computer-to-plate imaging members. Consequently, advances in epoxy resin chemistry have allowed for the use of epoxy resins material in aqueous formulations. The most common strategy for the use of such epoxy resins in aqueous formulations has involved the preparation of aqueous dispersions of hydrophobic, water-insoluble epoxy resins. These dispersions are typically stabilized either by a surfactant or a protective colloid such as poly(vinyl alcohol). Many of these dispersions are sold commercially and a representative example of this type of system is described in U.S. Pat. No. 5,602,193 (Stark). This class of epoxy resins, though formulated in water, are still largely hydrophobic in nature and are not suitable for the applications noted above wherein the target material or coating must be highly wettable or must have a very high water uptake or water compatibility. These resins are also largely incompatible with many water-soluble polymers and multi-phase formulations may result when they are used.
There are a large number of patents describing cationic epoxy resins of the type that are commonly used in electrophoretic coating processes (also knows as electrodeposition coating). Most of these resins, however, contain a mixture of primary, secondary, and tertiary amine groups and are designed such that they can be rendered water-soluble by neutralization with an acid. This property is crucial to their described use, as the production of hydroxide by water reduction at the cathode deprotonates the resin, and the resin is then deposited on a metal surface. This process results in the deposition of a tough, water-insoluble coating on a metal surface in which all of the net charge of the epoxy resin has been destroyed (or neutralized). Examples of cationic amine salt-containing epoxy resins of this type are described for example in U.S. Pat. No. 4,487,674 (Jan Al et al.), U.S. Pat. No. 5,483,012 (Midogohchi et al.), and U.S. Pat. No. 4,208,262 (Kubo et al.).
Epoxy resins used for electrodeposition coating are also broadly described in ACS Symposium Series # 114 (Epoxy Resin Chemistry), pp. 57-69, (Vol. Date 1978),
Journal of Coatings Technology
Vol. 54, No. 688, pp. 35-44 (1982), and
Journal of Coatings Technology
Vol. 54, No. 686, pp. 33-41 (1982).
The solubility of the known epoxy resins used for electrodeposition resins is responsive to pH. There is a desired to have cationic epoxy resins where the solubility is not responsive to pH so there is more latitude in formulation.
U.S. Pat. No. 4,035,275 (Sturni et al.), U.S. Pat. No. 3,839,252 (Bosso et al.), U.S. Pat. No. 3,619,398 (Bosso et al.), U.S. Pat. No. 4,001,156 (Bosso et al.), U.S. Pat. No. 4,110,287 (Bosso et al.), U.S. Pat. No. 4,144,159 (Bosso et al.), U.S. Pat. No. 4,038,166 (Bosso et al.), U.S. Pat. No. 4,081,341 (Christenson et al.), U.S. Pat. No. 3,894,922 (Bosso et al.), U.S. Pat. No. 3,936,405 (Sturni et al.), U.S. Pat. No. 3,962,165 (Bosso et al.), U.S. Pat. No. 3,937,679 (Bosso et al.), U.S. Pat. No. 3,959,106 (Bosso et al.), U.S. Pat. No. 3,928,156 (Wismer et al.), and U.S. Pat. No. 4,001,101 (Bosso et al.) broadly describe epoxy resins that contain both epoxy units and various cationic moieties. The resins preferably are phenolic-based and thus are highly aromatic in nature. This would increase their hydrophobic nature also. These resins, thus, tend to be more hydrophobic in character than is desired for a number of aqueous formulations.
Thus, there is a need for cationic epoxy compounds that are not pH sensitive, can be readily formulated and used in hydrophilic (or aqueous environments), and do not lose their ionic charge in coated form.
SUMMARY OF THE INVENTION
This invention provides a water-soluble or water-dispersible, branched or unbranched compound comprising a backbone having covalently attached two or more epoxy moieties and one or more of the same or different organoonium moieties.
In preferred embodiments, the organoonium moieties are the same or different organoammonium moieties, the same or different organophosphonium moieties, the same or different organosulfonium moieties, or the same or different N-alkylated, positively charged nitrogen-containing heterocyclic moieties, all of which are described in more detail below.
The cationic epoxy compounds of this invention comprise both epoxy units and organoonium moieties that are covalently bound to a backbone. Furthermore, the resins are derived from epoxy-containing backbone precursors that contain at least 25% by weight of oxygen with the remainder being aliphatic hydrocarbons and halogens. These precursor compounds are soluble in water or water-miscible solvents. These cationic epoxy compounds prepared therefrom are useful in the formulation of hydrophilic, water-compatible, water-swellable, or water-wettable coatings and materials and have unexpectedly good solution compatibility with oppositely charged polyelectrolytes. In contrast to the epoxy compounds known in the art, the cationic epoxy compounds of this invention have non-aromatic, oxygen-rich backbones.
DETAILED DESCRIPTION OF THE INVENTION
As most of the compounds of this invention are polydisperse materials having structures that will vary in degree of branching and the degree of functionalization (pendant moieties), it is implied that all descriptions of chemical compounds will apply to the mean, or average structure of each material. Thus, the compounds of this invention can be linear, partially branched to any degree, or fully branched in structure.
The compounds can be obtained from epoxy-containing “precursor compounds” that are branched or unbranched, monomeric, oligomeric, or polymeric compounds comprising at least 25% by weight of oxygen with the remainder of the weight comprising of aliphatic hydrocarbon and residual aliphatic haloalkyl groups (usually chloroalkyl groups). The oxygen atoms are covalently bound within the precursor compound as hydroxy, aliphatic ether, epoxy, or aliphatic ester moieties. Preferably, all non-epoxy moieties are either hydroxy or aliphatic ether groups. Preferably, the percentage of oxygen (by weight) in the precursor compounds is from about 30%
Leon Jeffrey W.
Mccovick Robert E.
West Paul R.
Eastman Kodak Company
Tucker J. Lanny
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