Arco Chemical Technology, L.p.

Gangfeng Cai

Lau S Yang

Robert G Gastinger

Jeffrey A Klang

Shau-Hua Guo

Andrew P Kahn

Carl J Sullivan

Diandre Armstead

Jeffrey M McFarland

Daniel M Trauth

Miscible blends of epoxy-extended polyetherester resins and commercial polymer resins are disclosed. Thermosets from the resin blends offer high-performance physical properties at a reduced cost compared with that of commercial high-performance resins. The thermosets have improved physical properties, including excellent water resistance, compared with many commercial systems. Resin blends of the invention are readily thickened, and are thus useful for SMC applications.

Miscible blends of epoxy-extended polyetherester resins and commercial polymer resins

A general approach to making water-resistant polyetherester resins and thermosets is disclosed. In one aspect, an unsaturated polyetherester resin prepared by inserting a carboxylic acid derivative into a polyether is co-cured with a vinyl monomer and a di- or polyisocyanate to give a water-resistant, thermoset that has excellent dimensional stability, flexibility, and strength properties. Processes for making low-viscosity resins that give thermosets with good water resistance are also described. In one process, an unsaturated polyetherester resin intermediate reacts with a mono-functional isocyanate or fatty alcohol to produce an easy-to-formulate, low-viscosity, low-molecular-weight capped resin.

Process for making water-resistant polyetherester resins and thermosets

A process for making polyetherester resins is disclosed. A glycol ester of an aromatic diacid such as terephthalic acid is reacted with a polyether and a source of a dicarboxylic acid such as maleic anhydride to produce a polyetherester resin, wherein the aromatic diester content may be conveniently adjusted as desired. The process permits the preparation of unsaturated polyetherester resins with relatively high levels of terephthalate repeating units while avoiding the difficulties associated with the direct use of terephthalic acid in previously known procedures. Such unsaturated polyetheresters are useful for making thermoset resins with excellent mechanical and physical properties. New glycol esters based on 2-methyl-1,3-propanediol, and polyester resins and thermosets made from the glycol esters, are also disclosed.

Process for making polyetherester resins having high aromatic diester

Processes for making poly(thioether ether)s and hydroxy-terminated poly(thioether ether)s are disclosed. The poly(thioether ether)s are made by bulk free-radical polymerization of diallyl ether and an aliphatic C.sub.2 -C.sub.10 dithiol. Liquid polymers are obtained when mixtures of two or more dithiols are used. Hydroxy-terminated products are obtained by reacting the poly(thioether ether)s with allyl alcohol under free-radical conditions.

Process for making poly(thioether ether)s from diallyl ether and dithiols

Processes for making storage-stable epoxy-capped polyetherester resins are disclosed. In one process, a polyetherester resin is first made by inserting a carboxylic acid derivative into a polyether. Reacting the resin with a capping agent gives an intermediate resin with a reduced content of free carboxylic acid groups. Finally, the intermediate resin reacts with an epoxy compound in the presence of a finishing catalyst under conditions effective to give an epoxy-capped resin. The resins have low weight average molecular weights (less than about 8000), narrow molecular weight distributions (less than 6), and low viscosities, making them an excellent choice for low-VOC formulations. The finishing catalyst helps to minimize resin viscosity drift and improves shelf stability. Curing the resins with a vinyl monomer gives thermosets with an excellent balance of physical properties, including excellent water resistance.

Process for making storage-stable epoxy-capped polyetherester resins

Esterification of an ultra-low unsaturation polyoxy(higher)alkylene polyol with a dicarboxylic acid or reactive derivative thereof to form a poly(half ester) followed by capping the poly(half ester) with a capping agent capable of forming an amide linkage or ester linkage while retaining primary hydroxyl functionality, generates high primary hydroxyl content polyols with substantially retained hydrophile/lipophile balance and low polydispersity. Low color products having primary hydroxyl contents in excess of 80 equivalent percent may be routinely achieved.

Low monol polyoxy (higher) alkylene polyols with primary hydroxyl content

A process for making high-performance polyetherester resins and thermosets is disclosed. A polyether polyol reacts with a dicarboxylic acid or anhydride in the presence of an insertion catalyst to produce an acid-terminated polyetherester resin. Reaction of this resin reacts with a primary diol or a diepoxy compound gives a chain-extended polyetherester resin that can be cured with a vinyl monomer to produce a high-performance polyetherester thermoset. Properties of the thermosets rival or exceed those of more expensive high-performance iso and vinyl ester resins.

Process for making high-performance polyetherester resins and thermosets

A process for making poly(2-methyl-1,3-propanediol) is disclosed. The process comprises heating 2-methyl-1,3-propanediol in the presence of an etherification catalyst at a temperature within the range of about 100.degree. C. to about 210.degree. C. The resulting poly(2-methyl-1,3-propanediol) has a degree of polymerization within the range of about 2 to about 20, and a number average molecular weight within the range of about 150 to about 2000. The process enables the synthesis of dimers and trimers of 2-methyl-1,3-propanediol, which are useful as reactive diluents or chain extenders for polyurethanes and as diol components for unsaturated polyester resins and thermoplastic polyesters.

Process for making poly(2-methyl-1,3-propanediol)

Stable emulsions based on unsaturated polyetherester resins are disclosed. The emulsions have high stability compared with conventional emulsions that are based on unsaturated polyester resins. The invention includes base-stabilized emulsions, as well as emulsions containing fillers or functional additives. The emulsions, which are storage stable for weeks or months, are useful for making water-extended polyetherester thermosets having excellent physical properties, even at high water contents.

Thermosets from water-extended polyetherester emulsions

A two-step process for making polyetherester resins is disclosed. A low molecular weight polyol reacts with an aromatic dicarboxylic acid in step one to produce a polyester intermediate. In step two, the polyester intermediate reacts with an anhydride or an aliphatic dicarboxylic acid in the presence of an insertion catalyst to produce a polyetherester resin that contains greater than about 10 wt. % of recurring units derived from the aromatic dicarboxylic acid. The polyetheresters are useful for making thermoset resins with excellent mechanical properties and chemical resistance.

Process for making polyetheresters with high aromatic ester content

Stable water-extended polyetherester emulsions

Tetrahydrofuran is polymerized in the presence of a carboxylic acid anhydride and a solid acid catalyst that has been calcined at a temperature greater than about 600.degree. C. Calcined bleaching earth catalysts give THF polymer products having a narrow molecular weight distribution; calcining amorphous silica-aluminas improves their activity toward THF polymerization.

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West Chester, PA, United States of America

Gangfeng Cai