Fluorescent poly(alkylene terephthalate) compositions

Abstract

Fluorescent poly(alkylene terephthalate) compositions are provided. The fluorescent poly(alkylene terephthalate) compositions contain fluorescent poly(alkylene terephthalate)s and are made from fluorescent compounds and poly(alkylene terephthalate) oligomers, or by polymerizing amine and acid monomers in the presence of fluorescent compounds.

1 . A fluorescent poly(trimethylene terephthalate) composition comprising: at least one fluorescent compound, and a poly(trimethylene terephthalate) oligomer or polymer.  
   
   
       2 . The composition of  claim 1 , wherein said composition comprises a blend comprising at least one of poly(trimethylene terephthalate) and at least one other polymer.  
   
   
       3 . The composition of  claim 2  wherein said other polymer is a polyester.  
   
   
       4 . The composition of  claim 2  wherein said other polymer is selected from poly(ethylene terephthalate), nylon 6, nylon 6,6, and poly(tetramethylene terephthalate).  
   
   
       5 . The composition of  claim 2  wherein said blend contains 70 mole % or more of the poly(trimethylene terephthalate).  
   
   
       6 . The composition of  claim 1 , wherein said oligomer comprises, as a monomer unit thereof, said fluorescent compound.  
   
   
       7 . The composition of  claim 1 , wherein said fluorescent compound is a monomer and is copolymerized with one or more other monomers to form a fluorescent oligomer.  
   
   
       8 . The composition of  claim 4 , wherein said poly(trimethylene terephthalate) comprises, as a polymerized unit, said fluorescent monomer.  
   
   
       9 . The composition of  claim 1 , comprising the poly(trimethylene terephthalate) polymer, the poly(trimethylene terephthalate) polymer having an inherent viscosity of about 0.85 to about 1.2 dL/g.  
   
   
       10 . The composition of  claim 1  wherein said fluorescent compound is selected from coumarins, flavones, and derivatives thereof.  
   
   
       11 . The composition of  claim 1  wherein said fluorescent compound is selected from: 1,2-disubstituted benzopyrones, 7-hydroxybenzopyrones, 10-carboxybenzopyrones, and trihydroxybenzopyrones.  
   
   
       12 . The composition of  claim 11  wherein said fluorescent compound is selected from: 6-hydroxy-flavone [6-hydroxy-2-phenyl-4-benzopyrone]; 7-hydroxy-4-methylcoumarin [2H-1-benzopyran-2-one, 7-hydroxy-4-methyl-]; 3-hydroxyflavone [4H-1-benzopyran-4-one, 3-hydroxy-2-phenyl-]; 3,5,7-trihydroxyflavone [3,5,7-trihydroxy-2-phenyl-4-benzopyrone, 4H-1-benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-]; 4′,5,7-trihydroxyflavone [5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone, 4H-1-benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)]; 5,7,4′-trihydroxy-4′-methoxyflavone [5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone]; coumarin 314 [1H,5H,11H-[1]-benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid, 2,3,6,7-tetrahydro-11-oxo-, ethyl ester]; coumarin 343 [1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid, 2,3,6,7-tetrahydro-11-oxo-]; 4-methylesculetin [2H-1-benzopyran-2-one, 6,7-dihydroxy-4-methyl-]; 4-methyl-7-aminocoumarin [2H-1-benzopyran-2-one, 7-amino-4-methyl]; and 7-hydroxy-4-(trifluoromethyl)coumarin [2H-1-benzopyran-2-one, 7-hydroxy-4-(trifluoromethyl)-].  
   
   
       13 . A fiber comprising the composition of  claim 1 .  
   
   
       14 . An oriented fiber according to  claim 13 .  
   
   
       15 . A bicomponent fiber according to  claim 13 .  
   
   
       16 . A multicomponent fiber according to  claim 13 .  
   
   
       17 . A fabric comprising a fiber according to  claim 13 .  
   
   
       18 . A carpet fiber according to  claim 13 .  
   
   
       19 . A textile fiber according to  claim 13 .  
   
   
       20 . A monofilament fiber according to  claim 13 .  
   
   
       21 . A nonwoven fiber article comprising a fiber according to  claim 13 .  
   
   
       22 . A molded article comprising the composition of  claim 1 .  
   
   
       23 . A film comprising the composition of  claim 1 .  
   
   
       24 . An engineering plastic comprising the composition of  claim 1 .  
   
   
       25 . A powder coating comprising the composition of  claim 1 .  
   
   
       26 . A process for making a fluorescent composition comprising a fluorescent oligomer comprising: 
 providing 1,3-propanediol and diacids, esters or diesters; and combining said one or more 1,3-propanediol and diacids, esters or diesters and a fluorescent compound, under conditions to form an oligomer, to form said fluorescent oligomer.    
   
   
       27 . The process of  claim 26  wherein said diacids, esters or diesters is said diacids, and said diacids are selected from isophthalic acid; 1,4-cylohexanedicarboxylic acid; 2,6-naphthalenedicarboxylic acid; 1,3-cyclohexanedicarboxylic acid; succinic acid; glutaric acid; adipic acid; sebacic acid; 1,12-dodecanedioic acid; and derivatives thereof.  
   
   
       28 . (canceled)  
   
   
       29 . The process of  claim 26 , further comprising melt blending said fluorescent oligomer with a poly(alkylene terephthalate) to provide a fluorescent poly(alkylene terephthalate).  
   
   
       30 . The process of  claim 29  wherein said poly(alkylene terephthalate) comprises poly(trimethylene terephthalate).  
   
   
       31 . The process of  claim 30  wherein the amount of said fluorescent compound is at least about 5 mg/kg of poly(alkylene terephthalate).  
   
   
       32 . The process of  claim 30  wherein the amount of said fluorescent compound is at least about 10 mg/kg of poly(alkylene terephthalate).  
   
   
       33 . The process of  claim 30  wherein the amount of said fluorescent compound is at least about 50 mg/kg of poly(alkylene terephthalate).  
   
   
       34 . The process of  claim 30  wherein the amount of said fluorescent compound is at least about 60 mg/kg of poly(alkylene terephthalate).  
   
   
       35 . The process of  claim 30  wherein the amount of said fluorescent compound is about 20,000 mg/kg of poly(alkylene terephthalate) or less.  
   
   
       36 . The process of  claim 30  wherein the amount of said fluorescent compound is about 10,000 mg/kg of poly(alkylene terephthalate) or less.  
   
   
       37 . The process of  claim 30  wherein the amount of said fluorescent compound is about 5,000 mg/kg of poly(alkylene terephthalate).  
   
   
       38 . The process of  claim 30  wherein the amount of fluorescent compound is from about 0.6% to about 20% by weight, based on the total combined weight of fluorescent oligomer and poly(alkylene terephthalate).  
   
   
       39 . The process of  claim 30  wherein the amount of fluorescent compound is from about 0.6% to about 15% by weight, based on the total combined weight of fluorescent oligomer and polyester.  
   
   
       40 . The process of  claim 30  wherein the amount of fluorescent compound is from about 0.6% to about 10% by weight, based on the total combined weight of fluorescent oligomer and polyester.  
   
   
       41 . The process of  claim 30  wherein the fluorescent compound is selected from coumarins, flavones and derivatives thereof.  
   
   
       42 . The process of  claim 26 , wherein said process is carried out in the presence of an inorganic acid.  
   
   
       43 . The process of  claim 26 , wherein said process is carried out at a temperature of about 200° C. or less.  
   
   
       44 . The process of  claim 26  wherein the fluorescent compound is selected from: 1,2-disubstituted benzopyrones, 7-hydroxybenzopyrones, 10-carboxybenzopyrones, and trihydroxybenzopyrones.  
   
   
       45 . The process of  claim 26  wherein said fluorescent compound is selected from: 1,2-disubstituted benzopyrones, 7-hydroxybenzopyrones, 10-carboxybenzopyrones, and trihydroxybenzopyrones. Preferred fluorescent compounds are 6-hydroxy-flavone [6-hydroxy-2-phenyl-4-benzopyrone]; 7-hydroxy-4-methylcoumarin [2H-1-benzopyran-2-one, 7-hydroxy-4-methyl-]; 3-hydroxyflavone [4H-1-benzopyran-4-one, hydroxy-2-phenyl-1; 3,5,7-trihydroxyflavone [3,5,7-trihydroxy-2-phenyl-4-benzopyrone, 4H-1-benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-]; 4′,5,7-trihydroxyflavone [5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone, 4H-1-benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl]; 5,7,4′-trihydroxy-3′-methoxyflavone (5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone]; coumarin 314 [1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carboxylic acid, 2,3,6,7-tetrahydro-11-oxo-, ethyl ester]; coumarin 343 [1H,5H,11H-[1]benzopyrano[6,7,8-ij]-quinolizine-10-carboxylic acid, 2,3,6,7-tetrahydro-11-oxo-]; 4-methylesculetin [2H-1-benzopyran-2-one, 6,7-dihydroxy-4-methyl-]; 4-methyl-7-aminocoumarin [2H-1-benzopyran-2-one, 7-amino-4-methyl-]; and 7-hydroxy-4-(trifluoromethyl)coumarin [2H-1-benzopyran-2-one, 7-hydroxy-4-(trifluoromethyl)-].  
   
   
       46 . A process for making a fluorescent poly(trimethylene terephthalate) composition comprising: providing a fluorescent compound and a poly(trimethylene terephthalate) oligomer; and contacting said fluorescent compound with said poly(trimethylene terephthalate) oligomer in an inert environment at a temperature of about 240° C. to about 255° C., to form a mixture, and allowing said mixture to polymerize, forming said fluorescent poly(trimethylene terephthalate).  
   
   
       47 . The process of  claim 46 , further comprising applying vacuum to said mixture.  
   
   
       48 . The process of  claim 46  wherein the amount of said fluorescent compound is at least about 5 mg/kg of poly(trimethylene terephthalate).  
   
   
       49 . The process of  claim 46  wherein the amount of said fluorescent compound is at least about 10 mg/kg of poly(trimethylene terephthalate).  
   
   
       50 . The process of  claim 46  wherein the amount of said fluorescent compound Is at least about 50 mg/kg of poly(trimethylene terephthalate).  
   
   
       51 . The process of  claim 46  wherein the amount of said fluorescent compound is at least about 60 mg/kg of poly(trimethylene terephthalate).  
   
   
       52 . The process of  claim 46  wherein the amount of said fluorescent compound is about 20,000 mg/kg of poly(trimethylene terephthalate) or less.  
   
   
       53 . The process of  claim 46  wherein the amount of said fluorescent compound is about 10,000 mg/kg of poly(trimethylene terephthalate) or less.  
   
   
       54 . The process of  claim 46  wherein the amount of said fluorescent compound is about 5,000 mg/kg of poly(trimethylene terephthalate).