Exxon Chemical Patents, Inc.

Exxon Research and Engineering Company

Other

William E Wellman

Albert Ilya Yezrielev

Michael G Romanelli

Ralph Martin Kowalik

George A Knudsen

Richard Henry Schlosberg

Ramzi Yanni Saleh

Paul E Burton

Albet I Yezrielev

Robert N Sachs

Non liquid-crystalline esterphenol-capped liquid polymer and polyol compositions in combination with an amino crosslinking agent endow coating compositions containing them with the ability of providing films having superior properties. The esterphenol-capped polymers and polyols can be prepared by direct esterification of hydroxybenzoic acid without its decarboxylation.

Process for preparing phenol-functional polymer

The present invention provides for amino-crosslinkable coating formulations based on a mixture of a di or polyhydroxy functional polymeric component selected from the group consisting of diesters, polyesters, alkyd polymers, acrylic polymers and polycarbonate polymers, a methylol (alkoxymethyl) amino crosslinking agent and a bis-aromatic polyhydric phenol component having the structure of formula I: ##STR1## wherein X is selected from the group consisting of carbon to carbon covalent bond, oxygen, sulfur, --S--S--, --CO--, --SO--, --SO.sub.2 -- and a divalent organic radical having a molecular weight less than about 400, and wherein Y is independently selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 alkoxy.

Thermoset coating compositions having improved hardness

The invention relates to the use of polybasic acids as gloss reduction agents in the preparation of paint or coating compositions based on hydroxy or phenolic functional resins and also containing an amino crosslinking agent and a pigment. Cured coatings exhibiting good flexibility, hardness and solvent resistance, as well as reduced or controllable gloss are obtained.

Gloss reduction agent for solvent based pigmented coating formulations

Liquid polymer and polyol compositions, and process for preparing

The present invention is directed towards a mixture of phenol terminated diesters and an amino crosslinking agent. The diesters are characterized by a structure consisting of ##STR1## wherein R is an aliphatic divalent hydrocarbon radical containing 2 to 40 carbon atoms or a mixture of such radicals, provided however that R contains at least about 8 carbon atoms when n is 0 and p is 0, R.sub.1 is an aliphatic or cycloaliphatic hydrocarbon radical containing 2 to 40 carbon atoms or a mixture of such radicals, R.sub.2 is a aliphatic, aromatic or a mixture of aliphatic and aromatic hydrocarbon radicals having from 2 to 40 carbon atoms, A is divalent aromatic radical selected from the group consisting of phenylene, naphthylene or bis phenylene, p is 0 or 1, n is 0 or an integer ranging from 1 to about 40, provided however, that p is 0 when n is 0 and p is 1 when n is an integer and ##STR2## wherein q is an integer ranging from 1 to about 40, n is 0 or an integer ranging from 1 to about 40 and A, R.sub.1 and R.sub.2 are as defined above.

Phenol terminated diester compositions derived from dicarboxylic acids,

The present invention is directed towards liquid coating formulations containing a mixture of a curable polyester or diester resin, an amino crosslinking agent and a pigment wherein the pigment is dispersed in the coating solution at a weight loading level such that the pigment to binder ratio falls within the range of from 1.25 to 1 up to about 5.0 to 1. The polyester or diester resins employed in the coating formulations are such that when formulated with an appropriate crosslinking agent, acid catalyst and pigment within the ranges stated above and properly applied to a substrate and cured, produce coatings having a minimum Knoop hardness of at least about 4 and a flexibility (T-bend test) of less than 6, generally less than about 5, and a MEK rub value of greater than 5, more preferably at least about 15 and most preferably greater than 50. Cured coating compositions prepared in accordance with this invention exhibit all of the attributes considered essential for coil coatings, i.e., good adhesion to the substrate and good gloss, and in addition provide an excellent balance of flexibility and hardness qualities despite high pigment loadings, and good to excellent weatherability when exposed to outdoor conditions.

Polyester-based coating compositions having high pigment-to-binder ratios

The present invention is directed towards a process for preparing non-liquid crystalline phenol-terminated diester compositions characterized by the structure of formula 1: ##STR1## wherein R is an aliphatic divalent hydrocarbon radical containing 2 to 40 carbon atoms or a mixture of such radicals, provided however that R contains at least about 8 carbon atoms when n is 0 and p is 0, R.sub.1 is an aliphatic or cycloaliphatic hydrocarbon radical containing 2 to 40 carbon atoms or a mixture of such radicals, R.sub.2 is an aliphatic, aromatic or a mixture of aliphatic and aromatic hydrocarbon radicals having from 2 to 40 carbon atoms, A is divalent aromatic radical selected from the group consisting of phenylene, naphthylene or his phenylene, p is 0 or 1, n is 0 or an integer ranging from 1 to about 40, provided however, that p is 0 when n is 0 and p is 1 when n is an integer. The invention is also directed to a single stage direct esterification or multi stage esterification processes for producing the aforementioned diesters of formula 1 either with or without the use of esterification catalysts, and is particularly directed to such processes for preparing diesters of reduced color using a low temperature process in combination with catalyst systems containing a phosphorous acid or derivative thereof.

Phenol terminated diester compositions derived from discarboxylic acids,

The present invention relates to a process for reactively separating hydrolyzable polymers, such as PET, in mixtures of the polymer and certain non-hydrolyzable polymers, specifically polyolefins by converting the hydrolyzable polymers to their corresponding water soluble components (e.g., PET to ethylene glycol and terephthalic acid) in the presence of liquid water at temperatures from about 200.degree. C. up to the critical temperature of water and autogenous pressure. The process has utility in recycling and waste material separation processes.

Process for separation of hydrolyzable from non-hydrolyzable waste

The present invention is directed towards liquid coating formulations containing a mixture of a curable polyester or diester resin, an amino crosslinking agent and a pigment wherein the pigment is dispersed in the coating solution at a weight loading .level such that the pigment to binder ratio falls within the range of from greater than 2.0 to 1 up to about 5.0 to 1. The polyester or diester resins employed in the coating formulations are such that when formulated with an appropriate crosslinking agent, acid catalyst and pigment within the ranges stated above and properly applied to a substrate and cured, produce coatings having a minimum Knoop hardness of at least about 4 and a flexibility (T-bend test) of less than 6, generally less than about 5, and a MEK rub value of greater than 5, more preferably at least about 15 and most preferably greater than 50.

The present invention is directed towards non-liquid crystalline phenol-terminated diester compositions which may be liquids or solids and crosslinkable formulations containing a mixture of the phenol terminated diesters and an amino crosslinking agent. These diesters are characterized by the structure of formula 1: ##STR1## wherein R is an aliphatic divalent hydrocarbon radical containing 2 to 40 carbon atoms or a mixture of such radicals, provided however that R contains at least about 8 carbon atoms when n is 0 and p is 0, R.sub.1 is an aliphatic or cycloaliphatic hydrocarbon radical containing 2 to 40 carbon atoms or a mixture of such radicals, R.sub.2 is an aliphatic, aromatic or a mixture of aliphatic and aromatic hydrocarbon radicals having from 2 to 40 carbon atoms, A is divalent aromatic radical selected from the group consisting of phenylene, naphthylene or bis phenylene, p is 0 or 1, n is 0 or an integer ranging from 1 to about 40, provided however, that p is 0 when n is 0 and p is 1 when n is an integer.

The present invention provides for amino-crosslinkable coating formulations based on a mixture of a di or polyhydroxy functional polymeric component selected from the group consisting of diesters, polyesters, alkyd polymers, acrylic polymers and polycarbonate polymers, a methylol (alkoxymethyl) amino crosslinking agent and a bis-aromatic polyhydric phenol component having the structure of formula I: ##STR1## wherein X is selected from the group consisting of carbon to carbon covalent bond, oxygen, sulfur, --S--S--, --CO--, --SO--, --SO.sub.2 -- and a divalent organic radical having a molecular weight less than about 400, and wherein Y is independently selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 alkoxy. The crosslinkable compositions of this invention may be used to prepare curable coating and paint formulations, and also may contain other ingredients such as a crosslinking catalyst, fillers, pigments and the like. When cured, the coatings of this invention exhibit improved hardness properties when compared with cured coatings which do not contain the aromatic polyhydric phenol additive. The presence of the additive also serves to eliminate the problem of coating softening when the coated substrate is baked for a prolonged period of time. These cured coatings also have good weatherability, good corrosion resistance and hydrolytic stability, enhanced oxidative and radiation stability, good solvent resistance and good adhesion properties.

Thermoset coating composition having improved hardness

According to one aspect of the present invention, an improved method for preparing acrylic copolymer resins is provided in which the polymerization solvent includes an internal olefin. The monomers comprise hydroxy-substituted alkyl (meth)acrylates, and non-hydroxy substituted alky (meth)acrylates, and the process provides an improved method for forming low molecular weight acrylic resins useful as components in high solids acrylic coatings suitable for electrostatic spraying. The polymerization solvent can remain in the resin to become the solvent employed in the higher solids coating containing the thus-forming acrylic resins and provides surprisingly improved electrical resistivity and color decreased over previously used polymerization solvents, and has good compatibility with the acrylic monomer/resin system.

Solvent mixture for production of high solids acrylic coating resins

According to one aspect of the present invention, improved acrylic copolymer resins are provided which are formed by co-polymerization of a monomer mixture comprising hydroxy-substituted alkyl (meth)acrylates, alkyl methacrylates or vinyl aromatics, and higher alpha-olefins. The invention provides improved low molecular weight acrylic resins useful as components in high solids acrylic coatings suitable for electrostatic spraying.

High solids acrylic-based coatings

According to one aspect of the present invention, improved acrylic copolymer resins are provided which are formed by co-polymerization of a monomer mixture comprising hydroxy-substituted alkyl (meth)acrylates, alkyl methlacrylates or vinyl aromatics, and higher alpha-olefins. The invention provides improved low molecular weight acrylic resins useful as components in high solids acrylic coatings suitable for electrostatic spraying.

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Edison, NJ, United States of America

William E Wellman