Browse Prior Art Database

Utility of 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (TMCD) in Coating Applications

IP.com Disclosure Number: IPCOM000198694D
Publication Date: 2010-Aug-12

Publishing Venue

The IP.com Prior Art Database

Related People

Eastman Chemical Company: OWNER

Abstract

Utility of 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (TMCD) in Coating Applications

This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 18% of the total text.

Page 1 of 13

Utility of 2,2,4,4-Tetramethyl-1,3-cyclobutanediol (TMCD) in Coating Applications

EASTMAN CHEMICAL COMPANY

ABSTRACT

2,2,4,4-Tetramethyl-1,3-cyclobutanediol (TMCD) is a cycloaliphatic polyester monomer known in the art for its ability to increase the glass transition temperature (Tg), chemical resistance and hydrolytic stability of amorphous terephthalate based co-polyesters. This communication describes the extension of these beneficial properties of TMCD into several coating application areas. In general, coatings containing TMCD combine excellent solubility in organic solvents with improved hardness, stain resistance, chemical resistance, humidity resistance, hydrolytic stability and outdoor durability. Relative to the gain in hardness, these coatings still exhibit excellent flexibility. This combination of properties is useful in application areas as diverse as powder coatings, polyurethane dispersions, thermoplastic polyurethanes, water soluble and water reducible polyester coatings, waterborne alkyds, solventborne alkyds, container coatings, UV curable coatings and bio-based or renewable coatings.

BACKGROUND

The hardness of a polyester based coating is positively correlated with the Tg of the polyester contained therein. In general, coatings that exhibit high hardness are desirable. Coatings with high hardness typically exhibit high gloss, good distinctness of image (DOI), fast dry-times, scratch resistance, stain resistance, chemical resistance, humidity resistance and outdoor durability.

Coatings exhibiting high hardness can be prepared using resins containing a high amount of 2,2-dimethyl- 1,3-propanediol (NPG) and isophthalic acid (PIA). However, polyester resins of this type typically exhibit poor solubility in organic solvents and produce coatings with poor flexibility.

Solubility can be improved by incorporating aliphatic monomers such as 1,6-hexanediol (HD), 2,2,4- trimethyl-1,3-pentanediol (TMPD), 2-butyl-2-ethyl-1,3-propanediol (BEPD), adipic acid (AD), 1,4- cyclohexanedicarboxylic acid (CHDA) or hexahydrophthalic anhydride (HHPA). Unfortunately, these monomers simultaneously lower coating hardness and adversely affect the desirable properties associated with higher hardness.

A cycloaliphatic diol often used in a coatings to increase hardness and improve related properties is 1,4- cyclohexanedimethanol (CHDM). Unfortunately, as CHDM content is increased in the resin formulation, poor solubility results. This is particularly observed when high amounts of aromatic dicarboxylic acid, such as PIA, are used in the resin formulation.

Page 2 of 13

DETAILED DESCRIPTION

TMCD IN COATING APPLICATIONS

2,2,4,4-Tetramethyl-1,3-cyclobutanediol (TMCD) is a cycloaliphatic polyester monomer known in the art for its ability to increase the Tg, chemical resistance and hydrolytic stability of amorphous terephthalate based co-polyesters. This communication describes the extension of these beneficial properties of TMCD into several coati...