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US 6,787,589 B2Granted
Amber polyester compositions and container articles produced therefrom
AssigneeEastman Chemical Company
InventorsMax Allen Weaver, Marc Alan Strand, Crystal Leigh Kendrick, Gerry Foust Rhodes, Gertrude Williams, Jason Clay Pearson, Timothy Alan Upshaw
Life of this patent
Estimating the term…
Abstract
This application discloses amber colored polyesters suitable for packaging food and beverages. The amber polyester compositions provide excellent blockage of UV and visible light over the wavelength ranges of from about 320-550 nm, rendering them suitable for packaging materials sensitive to ultraviolet and visible light over this wavelength range, particularly beer.
Claims24
An amber polyester composition comprising a thermoplastic, molding grade polyester containing at least one compound, or the reacted residue of at least one compound, of each of Components I, II, III and, optionally, IV wherein Components I, II and III have the formulas:
- and the Component IV Compound(s) are one or more phthalocyanine compounds;
- wherein
- R is hydrogen, C1-C8-alkyl, or —(CH2CH2—O[Parenclosest]n1—CH2CH2—X wherein n1 is 1-3 and X is a polyester reactive group selected from hydroxy, carboxy, C2-C6-alkanoyloxy and C2-C6-alkoxycarbonyl;
- R1 is hydrogen or 1-2 groups selected from C1-C6-alkyl, C1-C6-alkoxy or halogen;
- R2 and R3 each is C1-C8-alkyl, C3-C8-alkenyl, C3-C8-alkynyl, C3-C8-cycloalkyl or aryl;
- R2 and R3 in combination may represent a divalent group such as pentamethylene, ethyleneoxyethylene or ethylenesulfonylethylene;
- or R2 in combination with R1 may form an N-substituted 1,2,3,4-tetrahydroquinolin-6-yl ring;
- R4 is C1-C8-alkyl;
- R5 and R6 each is hydrogen or one to two groups selected from C1-C6-alkyl, C1-C6-alkoxy and halogen;
- R7 is hydrogen, —(—CH2CH2O—)—n1—CH2CH2—X wherein n1 and X are defined above and C1-C6-alkyl;
- R8 is hydrogen or one or two groups selected from C1-C6-alkyl, C1-C6-alkoxy and halogen;
- R9 and R10 each is hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl or aryl;
- P is cyano, C1-C6-alkylsulfonyl, arylsulfonyl, aryl, heteroaryl, —CO2R11 and —CO2N(R12)R13, wherein R11 is C1-C6-alkyl, C3-C8-alkenyl, C3-C8-cycloalkyl and aryl:
- R12 and R13 each is independently selected from hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl and aryl;
- Q is one of the groups in the preceding definition of P;
- L is an organic di-, tri- or tetravalent linking group;
- L1 is an organic divalent linking group;
- L2 is an organic divalent linking group;
- n is an integer from 1 to 4;
- m is an integer from 2 to about 50;
- and
- m2 is 0, 1 or 2.
19 more elements
A thermoplastic, amber, molding composition comprising a polyester having an inherent viscosity of about 0.6 to 0.9 dL/g comprising:
- (1) diacid residues comprised of at least about 85 mole percent terephthalic acid residues, 2,6-naphthalenedicarboxylic acid residues, or a mixture of terephthalic acid and 2,6-naphthalenedicarboxylic acid residues;
- and
- (2) diol residues comprising at least about 50 mole percent, preferably at least 85 mole percent, ethylene glycol residues;
- wherein the polyester contains at least one compound, or the reacted residue of at least one compound, of each of Components I, II and III wherein Components I, II and III have the formulas:
- Component I Compounds:
- wherein R is hydrogen, methyl, 2-hydroxyethyl, 2-acetoxyethyl or 4-(methoxycarbonyl)benzyl;
- R1 is hydrogen or methoxy;
- and P is cyano, methoxycarbonyl, methylsulfonyl or arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R is hydrogen, methyl, 2-hydroxyethyl, 2-acetoxyethyl, or 4-(methoxycarbonyl)benzyl;
- R1 is hydrogen or methoxy;
- and P is cyano, methoxycarbonyl, methylsulfonyl or arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R is hydrogen, methyl, 2-hydroxyethyl, 2-acetoxyethyl, or 4-(methoxycarbonyl)benzyl;
- R1 is hydrogen or methoxy;
- and L is ethylene, tetramethylene, or 1,4-cyclohexylenedimethylene and n is 2 or L is C—(CH2)— and n is 4;
- wherein R1 is hydrogen or methoxy;
- and L1 and L2 are each ethylene, tetramethylene or 1,4-cyclohexylenedimethylene;
- and m is about 3 to 25;
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and P and Q are independently selected from cyano, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and L is ethylene, tetramethylene or 1,4-cyclohexylenedimethylene and n is 2 or L is C—(CH2)— and n is 4;
- wherein R1 is hydrogen, methyl or methoxy;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- Component II Compounds:
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 1-(methoxycarbonyl)benzyl;
- and P and Q are independently selected from cyano, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R1 is hydrogen, methyl or methoxy;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and L is ethylene, tetramethylene or 1,4-cyclohexylenedimethylene and n is 2 or L is C—(CH2)— and n is 4;
- wherein R4 is C1-C4-alkyl, 2-hydroxyethyl or 2-acetoxyethyl;
- R5 and R6 are each hydrogen;
- and P is C2-C7-alkoxycarbonyl;
- wherein R4 is C1-C4 alkyl, 2-hydroxyethyl or 2-acetoxyethyl;
- R5 and R6 are each hydrogen;
- L2 is ethylene, tetramethylene or 1,4-cyclohexylenedimethylene;
- and m is about 3 to 25;
- wherein R4 is C1-C4 alkyl, 2-hydroxyethyl or 2-acetoxyethyl;
- R5 and R6 are each hydrogen;
- and m is about 3 to 25;
- wherein each R1 is hydrogen, R7 is hydrogen, methyl or 2-hydroxyethyl and m1 is 1 or 2;
- wherein each R1 is hydrogen, R7 is methyl, ethyl or 2-hydroxyethyl;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)-benzyl;
- Component III Compounds:
- wherein R8 is hydrogen, methyl or chloro and R7 is hydrogen, methyl or 2-hydroxyethyl;
- wherein R9 and R10 are independently selected from hydrogen and methyl and X is hydroxy, acetoxy, carboxyl, methoxycarbonyl or ethoxycarbonyl.
47 more elements
A thermoplastic, amber, molding composition comprising a polyester having an inherent viscosity of about 0.6 to 0.9 dL/g comprising:
- (1) diacid residues comprised of at least about 85 mole percent terephthalic acid residues, 2,6-naphthalenedicarboxylic acid residues, or a mixture of terephthalic acid and 2,6-naphthalenedicarboxylic acid residues;
- and
- (2) diol residues comprising at least about 50 mole percent, preferably at least 85 mole percent, ethylene glycol residues;
- wherein the polyester contains 500 to 6000 ppm of a compound, or the reacted residue of a compound, having the formula:
- wherein R1 is hydrogen, methyl or methoxy;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and 50 to 300 ppm copper phthalocyanine.
4 more elements
A polyester concentrate of light absorbing compounds comprising a polyester having an inherent viscosity of about 0.6 to 0.9 dL/g comprising:
- (1) diacid residues comprised of at least about 85 mole percent terephthalic acid residues, 2,6-naphthalenedicarboxylic acid residues, or a mixture of terephthalic acid and 2,6-naphthalenedicarboxylic acid residues;
- and
- (2) diol residues comprising at least about 50 mole percent, preferably at least 85 mole percent, ethylene glycol residues;
- wherein the polyester contains at least one compound, or the reacted residue of at least one compound, of each of Components I, II and III wherein Components I, II and III have the formulas:
- wherein R is hydrogen, methyl, 2-hydroxyethyl, 2-acetoxyethyl or 4-(methoxycarbonyl)benzyl;
- R1 is hydrogen or methoxy;
- and P is cyano, methoxycarbonyl, methylsulfonyl or arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R is hydrogen, methyl, 2-hydroxyethyl, 2-acetoxyethyl, or 4-(methoxycarbonyl)benzyl;
- R1 is hydrogen or methoxy;
- and P is cyano, methoxycarbonyl, methylsulfonyl or arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R is hydrogen, methyl, 2-hydroxyethyl, 2-acetoxyethyl, or 4-(methoxycarbonyl)benzyl;
- R1 is hydrogen or methoxy;
- and L is ethylene, tetramethylene, or 1,4-cyclohexylenedimethylene and n is 2 or L is C—(CH2)— and n is 4;
- wherein R1 is hydrogen or methoxy;
- and L1 and L2 are each ethylene, tetramethylene or 1,4-cyclohexylenedimethylene;
- and m is about 3 to 25;
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and P and Q are independently selected from cyano, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and L is ethylene, tetramethylene or 1,4-cyclohexylenedimethylene and n is 2 or L is C—(CH2)— and n is 4;
- wherein R1 is hydrogen, methyl or methoxy;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- Component II Compounds:
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and P and Q are independently selected from cyano, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl and arylsulfonyl wherein aryl is phenyl or tolyl;
- wherein R1 is hydrogen, methyl or methoxy;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- wherein R1 is hydrogen, methyl or methoxy;
- R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl;
- and L is ethylene, tetramethylene or 1,4-cyclohexylenedimethylene and n is 2 or L is C—(CH2)— and n is 4;
- wherein R4 is C1-C4 alkyl, 2-hydroxyethyl or 2-acetoxyethyl;
- R5 and R6 are each hydrogen;
- and P is C2-C7-alkoxycarbonyl;
- wherein R4 is C1-C4 alkyl, 2-hydroxyethyl or 2-acetoxyethyl;
- R5 and R6 are each hydrogen;
- L2 is ethylene, tetramethylene or 1,4-cyclohexylenedimethylene;
- and m is about 3 to 25;
- wherein R4 is C1-C4 alkyl, 2-hydroxyethyl or 2-acetoxyethyl;
- R5 and R6 are each hydrogen;
- and m is about 3 to 25;
- wherein each R1 is hydrogen, R7 is hydrogen, methyl or 2-hydroxyethyl and m1 is 1 or 2;
- wherein each R1 is hydrogen, R7 is methyl, ethyl or 2-hydroxyethyl;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)-benzyl;
- Component III Compounds:
- wherein R8 is hydrogen, methyl or chloro and R7 is hydrogen, methyl or 2-hydroxyethyl;
- wherein R9 and R10 are independently selected from hydrogen and methyl and X is hydroxy, acetoxy, carboxyl, methoxycarbonyl or ethoxycarbonyl, wherein the concentration of the individual light-absorbing compounds of Components I, II, and III present in the polyester is in the range of about 0.5 to 30 weight percent and the maximum total concentration of all light-absorbing compounds of Components I, II, and III is about 50 weight percent, based on the total weight of the polyester concentrate.
46 more elements
A polyester concentrate comprising a polyester having an inherent viscosity of about 0.6 to 0.9 dL/g comprising:
- (1) diacid residues comprised of at least about 85 mole percent terephthalic acid residues, 2,6-naphthalenedicarboxylic acid residues, or a mixture of terephthalic acid and 2,6-naphthalenedicarboxylic acid residues;
- and
- (2) diol residues comprising at least about 50 mole percent, preferably at least 85 mole percent, ethylene glycol residues;
- wherein the polyester contains 0.5 to 30 weight percent, based on the total weight of the polyester concentrate, of at least one compound, or the reacted residue of at least one compound, of having formula II-B:
- wherein R1 is hydrogen, methyl or methoxy;
- and R2 and R3 are independently selected from methyl, ethyl, 2-hydroxyethyl, 2-acetoxyethyl, 2-chloroethyl, 2-cyanoethyl, cyclohexyl, phenyl, benzyl, and 4-(methoxycarbonyl)benzyl.
3 more elements
Dependencies are inferred from the claim text.