Novel Compositions Comprising Structural Isomers Of 1,4-Cyclohexanedimethanol Dibenzoate and Polymer Compositions Containing Same

Abstract

Novel solid benzoate ester compositions are mixtures comprising the trans- and cis-structural isomers of 1,4-cyclohexanedimethanol dibenzoate wherein the trans isomer constitutes from 1 to 66 or from 72 to 99 weight percent of the mixture. The properties imparted to a variety of polymer compositions, including hot melt adhesives, cannot be achieved using the commercially available mixture of these isomers.

1 . A composition comprising trans and cis isomers of 1,4-cyclohexane-dimethanol dibenzoate wherein the trans isomer constitutes from 72 to 99 weight percent of said composition. 
     
     
         2 . A composition according to  claim 1  wherein the trans isomer is from 90 to 94 weight percent of said composition, and the composition has a melting point of 120 to 128° C. 
     
     
         3 . A composition comprising trans and cis isomers of 1,4-cyclohexane-dimethanol dibenzoate, wherein the trans isomer is from 1 to 66 weight percent of said composition. 
     
     
         4 . A composition according to  claim 3  wherein the trans isomer is from 48 to 52 weight percent of said composition and the melting point of said composition is from 80 to 84° C. 
     
     
         5 . A method for preparing a solid composition comprising cis- and trans-isomers of 1,4-cyclohexanedimethanol dibenzoate and containing more than 72 weight percent of said trans isomer, said method comprising
 1) heating to above its melting point a composition comprising 68-70 weight percent of the trans isomer and 30 to 32 weight percent of said cis isomer for a time interval sufficient to form a molten material;   2) allowing said molten material to cool to 100° C. and maintaining this temperature for a period of time effective to crystallize and isolate a solidified composition containing said trans isomer, and   3) allowing the remaining portion of said molten composition to solidify.   
     
     
         6 . A method according to  claim 5  wherein the concentration of said trans isomer is increased by increasing the time period for crystallization. 
     
     
         7 . A hot melt adhesive composition comprising a a) at least one polymer selected from the group consisting of ethylene/vinyl acetate copolymers, polyolefins, block copolymers based on styrene, acrylates and olefins, olefins based on metallocene catalysts, amorphous polyalphaolefins, acrylic rubber including acrylic triblocks, ethylene/ethyl acrylate copolymers, polyurethanes of the reactive and non-reactive types, polyesters, sulfopolyesters and polyamides; b) a tackifying resin selected form the group consisting of aliphatic resins, aromatic resins, pure monomer resins, cycloaliphatic resins, rosin, resin esters, terpene and mixed monomer resins, c) an antioxidant and d) a modifier composition selected from the group consisting of (1) mixtures of trans and cis isomers of 1,4-cyclohexane-dimethanol dibenzoate wherein the trans isomer constitutes from 72 to 99 weight percent of said composition, and (2) mixtures of trans and cis isomers of 1,4-cyclohexane-dimethanol dibenzoate wherein the trans isomer constitutes from 1 to 66 weight percent of said solid composition. 
     
     
         8 . A method for accelerating a set time and crystallization rate of a hot melt adhesive composition comprising a thermoplastic polymer, a resin and a modifier, said method comprising selecting as said modifier a blend of structural isomers of 1,4-dimethyl-cyclohexyl dibenzoate containing at least 72 weight percent trans isomer. 
     
     
         9 . A method according to  claim 8  wherein said thermoplastic polymer is selected form the group consisting of ethylene/vinyl acetate copolymers, polyolefins, metallocene-catalyzed olefin polymers, amorphous polyolefins, block copolymers based on styrene acrylates and olefins, ethylene/ethyl acrylate copolymers, polyurethanes of the reactive and non-reactive types, polyesters, sulfopolyesters, acrylic block and triblock copolymers, acrylic elastomers and polyamides, and the tackifying resin is selected from the group consisting of aliphatic, cycloaliphatic and aromatic resins, pure monomer resins, functional resins, and terpene resins, and said blend contains 90 to 94 weight percent of said trans isomer. 
     
     
         10 . A composite article comprising two bonded layers of materials selected from the group consisting of woven and non-woven fabrics, and solid films and sheets formed from natural and synthetic polymers, wherein the bonding has been achieved using a molten adhesive composition comprising an organic polymer, a resin and a modifier selected from the group consisting of a first mixture containing more than 72 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate. 
     
     
         11 . A composite article according to  claim 10  wherein said article is selected from the group consisting of non-woven fabrics, packaging materials, glue sticks, construction materials, book bindings and labels. 
     
     
         12 . A composite article according to  claim 11  wherein said non-woven fabric is a diaper or a feminine hygiene article. 
     
     
         13 . A composition comprising an organic polymer and a modifier for said polymer, wherein said modifier is selected from the group consisting of
 (1) mixtures comprising the trans and cis isomers of 1,4-cyclohexane-dimethanol dibenzoate wherein the trans isomer constitutes from 72 to 99 weight percent of said composition; and   (2) mixtures comprising the said isomers wherein the trans isomer constitutes from 1 to 66 weight percent of said coating composition.   
     
     
         14 . A composition according to  claim 13  wherein said composition is a plastisol. 
     
     
         15 . A composition according to  claim 13  wherein said polymer is selected from the group consisting of engineering plastics for the fabrication of articles by extrusion or injection molding. 
     
     
         16 . A composition according to  claim 13  wherein said composition further comprises an organic or aqueous vehicle. 
     
     
         17 . A composition according to  claim 13  wherein said composition is selected from the group consisting of coatings, inks, varnishes, and room temperature activated adhesives. 
     
     
         18 . A composition according to  claim 17  wherein said coating is a powder coating and said ink is a hot melt jet ink and said varnish is an overprint varnish. 
     
     
         19 . A composition according to  claim 13  wherein said modifier is a process aid for said polymer. 
     
     
         20 . A method according to  claim 8  wherein said thermoplastic polymer is selected form the group consisting of ethylene/vinyl acetate copolymers, polyolefins, metallocene-catalyzed olefin polymers, amorphous polyolefins, block copolymers based on styrene acrylates and olefins, ethylene/ethyl acrylate copolymers, polyurethanes of the reactive and non-reactive types, polyesters, sulfopolyesters, acrylic block and triblock copolymers, acrylic elastomers and polyamides, and the tackifying resin is selected from the group consisting of aliphatic, cycloaliphatic and aromatic resins, pure monomer resins, functional resins, and terpene resins, and said blend contains 48-52 weight percent of said trans isomer. 
     
     
         21 . A composite article comprising two bonded layers of materials selected from the group consisting of woven and non-woven fabrics, and solid films and sheets formed from natural and synthetic polymers, wherein the bonding has been achieved using a molten adhesive composition comprising an organic polymer, a resin and a modifier selected from the group consisting of a first mixture containing less than 66 weight percent of the trans isomer of 1,4-cyclohexanedimethanol dibenzoate 
     
     
         22 . A composite article according to  claim 19  wherein said article is selected from the group consisting of non-woven fabrics, packaging materials, glue sticks, construction materials, book bindings and labels. 
     
     
         23 . A composite article according to  claim 20  wherein said non-woven fabric is a diaper or a feminine hygiene article.