US5102980A
Expired / Lapsed
US
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Colored polyester compositions
Assignee: Eastman Chemical Co
•
Filing: 1991-04-01
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Granted: 1992-04-07
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Expires: 2011-04-01
Abstract
Abstract Provided are novel polyester compositions containing copper phthalocyanine sulfonamide colorants copolymerized therein. Also provided are amorphous color concentrates, partially-crystalline color concentrates and semi-crystalline color concentrates. These polyester compositions are particularly useful for use as colored packaging materials and for colorants for personal, medical, and home care products where non-extractability of the colorant residue is important.
Inventors
- 👤 James J. Krutak
- 👤 Max A. Weaver
- 👤 Clarence A. Coates
- 👤 William W. Parham
- 👤 Terry A. Oldfield
- 👤 Wayne P. Pruett
- 👤 Samuel D. Hilbert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:53
CPC Classifications
C; C09; C09B; C09B69/00; C09B69/10; C08; C08G; C08G63/00; C08G63/68; C08G63/688
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
158 words
A polyester composition having copolymerized therein or reacted therewith at least 0.001 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α --Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue, optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 2
Dependent Claim
158 words
A polyester composition having copolymerized therein or reacted therewith at least 0.001 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α --Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue, optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 3
Dependent Claim
14 words
The polyester composition of claim 1 wherein Z is an unsubstituted copper phthalocyanine residue.
Claim 4
Dependent Claim
13 words
The polyester composition of claim 1 wherein M is an alkali metal cation.
Claim 5
Dependent Claim
12 words
The polyester composition of claim 3 wherein M is Na + .
Claim 6
Dependent Claim
17 words
The polyester composition of claim 1 wherein X is hydroxy, carboxy, or C 1- C 10 alkoxycarbonyl.
Claim 7
Dependent Claim
11 words
The polyester composition of claim 1 wherein R 1 is hydrogen.
Claim 8
Dependent Claim
130 words
The polyester composition of claim 1 wherein --R--X is selected from C 1- C 10 alkylene-CO 2 R 4 , C 2- C 10 alkylene-OH, C 1- C 10 alkylene-phenylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-CO 2 R 4 , arylene-C 2- C 10 alkylene-(CO 2 R 4 ) 2 , arylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene-CO 2 R 4 , C 1- C 10 alkylene -arylene-C 1- C 10 alkylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene-C 1- C 10 alkylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-O-arylene-C 1- C 10 alkylene-CO 2 R 4 , and C 1- C 10 alkylene cyclohexylene-C 1- C 10 alkylene-OH, wherein R 4 is hydrogen or C 1- C 6 alkyl.
Claim 9
Dependent Claim
23 words
The polyester composition of claim 1 wherein R 1 is hydrogen, C 1- C 10 alkyl, C 3- C 10 cycloalkyl, or phenyl.
Claim 10
Dependent Claim
27 words
The polyester composition of claim 1 wherein the residue of Formula (1) is present in a range of about 1 weight percent to about 30 weight percent.
Claim 11
Dependent Claim
27 words
The polyester composition of claim 9, wherein the residue of Formula (1) is present in a range of about 5 weight percent to about 20 weight percent.
Claim 12
Dependent Claim
21 words
The polyester composition of claim 1, wherein the value of β is in a range from about 2.0 to about 2.5.
Claim 13
Dependent Claim
164 words
An amorphous color concentrate comprising an amorphous polyester having copolymerized therein or reacted therewith at least about 5.0 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α-- Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue, optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 14
Dependent Claim
164 words
An amorphous color concentrate comprising an amorphous polyester having copolymerized therein or reacted therewith at least about 5.0 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α-- Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue, optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 15
Dependent Claim
14 words
The polyester composition of claim 12 wherein Z is an unsubstituted copper phthalocyanine residue.
Claim 16
Dependent Claim
13 words
The polyester composition of claim 12 wherein M is an alkali metal cation.
Claim 17
Dependent Claim
12 words
The polyester composition of claim 12 wherein M is Na + .
Claim 18
Dependent Claim
17 words
The polyester composition of claim 12 wherein X is hydroxy, carboxy, or C 1- C 6 alkoxycarbonyl.
Claim 19
Dependent Claim
11 words
The polyester composition of claim 12 wherein R 1 is hydrogen.
Claim 20
Dependent Claim
18 words
The polyester composition of claim 12 wherein the value of β is in a range from about 2.0-2.5.
Claim 21
Dependent Claim
132 words
The polyester composition of claim 13 wherein --R--X is selected from C 1- C 10 alkylene-CO 2 R 4 , C 2- C 10 alkylene-OH, C 1- C 10 alkylene-phenylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-CO 2 R 4 , arylene-C 2- C 10 alkylene-(CO 2 R 4 ) 2 , arylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene-CO 2 R 4 , C 1- C 10 alkylene-arylene -C 1- C 10 alkylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene -C 1- C 10 alkylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-O -arylene-C 1- C 10 alkylene-CO 2 R 4 , and C 1- C 10 alkylene cyclohexylene-C 1- C 10 alkylene-OH, wherein R 4 is hydrogen or C 1- C 6 alkyl.
Claim 22
Dependent Claim
23 words
The polyester composition of claim 12 wherein R 1 is hydrogen, C 1- C 10 alkyl, C 3- C 10 cycloalkyl, or phenyl.
Claim 23
Dependent Claim
165 words
A partially-crystalline polyester color concentrate composing a partially-crystalline polyester having copolymerized therein or reacted therewith at least about 5.0 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α-- Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 24
Dependent Claim
165 words
A partially-crystalline polyester color concentrate composing a partially-crystalline polyester having copolymerized therein or reacted therewith at least about 5.0 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α-- Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 25
Dependent Claim
14 words
The polyester composition of claim 21 wherein Z is an unsubstituted copper phthalocyanine residue.
Claim 26
Dependent Claim
13 words
The polyester composition of claim 21 wherein M is an alkali metal cation.
Claim 27
Dependent Claim
12 words
The polyester composition of claim 21 wherein M is Na + .
Claim 28
Dependent Claim
18 words
The polyester composition of claim 21 wherein X is hydroxy, carboxy, or C 1- C 6 alkoxy carbonyl.
Claim 29
Dependent Claim
11 words
The polyester composition of claim 21 wherein R 1 is hydrogen.
Claim 30
Dependent Claim
21 words
The polyester composition of claim 21 wherein the value of β is in a range from about 2.0 to about 2.5.
Claim 31
Dependent Claim
132 words
The polyester composition of claim 21 wherein --R--X is selected from C 1- C 10 alkylene-CO 2 R 4 , C 2- C 10 alkylene-OH, C 1- C 10 alkylene-phenylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-CO 2 R 4 , arylene-C 2- C 10 alkylene-(CO 2 R 4 ) 2 , arylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene-CO 2 R 4 , C 1- C 10 alkylene-arylene -C 1- C 10 alkylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene -C 1- C 10 alkylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-O -arylene-C 1- C 10 alkylene-CO 2 R 4 , and C 1- C 10 alkylene cyclohexylene-C 1- C 10 alkylene-OH, wherein R 4 is hydrogen or C 1- C 6 alkyl.
Claim 32
Dependent Claim
23 words
The polyester composition of claim 21 wherein R 1 is hydrogen, C 1- C 10 alkyl, C 3- C 10 cycloalkyl, or phenyl.
Claim 33
Dependent Claim
185 words
A colored semicrystalline powder having an average particle diameter of less than about 50 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization-precipitation to impart crystallinity thereto having copolymerized therein or reacted therewith at least about 5.0 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α-- Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue, optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 34
Dependent Claim
185 words
A colored semicrystalline powder having an average particle diameter of less than about 50 microns comprising a normally-amorphous polyester which has been modified by dissolution-crystallization-precipitation to impart crystallinity thereto having copolymerized therein or reacted therewith at least about 5.0 weight percent of a residue of Formula (I) (MO.sub.3 S).sub.α-- Z--[SO.sub.2 N(R.sub.1)R--X].sub.β(I) wherein Z is a copper phthalocyanine residue, optionally substituted with 1-12 groups selected from C 1- C 10 alkyl, C 1- C 10 alkoxy, C 1- C 10 alkylthio, arylthio, or halo; M is hydrogen, an alkali metal cation, an ammonium or substituted ammonium cation; R is a C 1- C 20 divalent organic residue; X is a group reactive with at least one of the functional groups of the monomers from which the polyester is prepared; R 1 is hydrogen, C 1- C 10 alkyl, C 1- C 10 substituted alkyl, C 3- C 10 cycloalkyl, aryl, or a group of the formula --R--X; α is 0, 1, or 2; and β is 1, 2, 3 or 4, provided that the sum of α plus β is equal to or less than 4.
Claim 35
Dependent Claim
14 words
The polyester composition of claim 30 wherein Z is an unsubstituted copper phthalocyanine residue.
Claim 36
Dependent Claim
13 words
The polyester composition of claim 30 wherein M is an alkali metal cation.
Claim 37
Dependent Claim
12 words
The polyester composition of claim 30 wherein M is Na + .
Claim 38
Dependent Claim
17 words
The polyester composition of claim 30 wherein X is hydroxy, carboxy, or C 1- C 6 alkoxycarbonyl.
Claim 39
Dependent Claim
11 words
The polyester composition of claim 30 wherein R 1 is hydrogen.
Claim 40
Dependent Claim
20 words
The polyester composition of claim 30 wherein the value of β is in a range about 2.0 to about 2.5.
Claim 41
Dependent Claim
130 words
The polyester composition of claim 34 wherein --R--X is selected from C 1- C 10 alkylene-CO 2 R 4 , C 2- C 10 alkylene-OH, C 1- C 10 alkylene-phenylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-CO 2 R 4 , arylene-C 2- C 10 alkylene-(CO 2 R 4 ) 2 , arylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene-CO 2 R 4 , C 1- C 10 alkylene -arlene-C 1- C 10 alkylene-CO 2 R 4 , C 1- C 10 alkylene-O-arylene-C 1- C 10 alkylene-CO 2 R 4 , arylene-C 1- C 10 alkylene-O-arylene-C 1- C 10 alkylene-CO 2 R 4 , and C 1- C 10 alkylene cyclohexylene-C 1- C 10 alkylene-OH, wherein R 4 is hydrogen or C 1- C 6 alkyl.
Claim 42
Dependent Claim
23 words
The polyester composition of claim 30 wherein R 1 is hydrogen, C 1- C 10 alkyl, C 3- C 10 cycloalkyl, or phenyl.
Claim 43
Dependent Claim
10 words
A formed article comprising the polyester composition of claim 1.
References Cited (Backward Citations)
US2219330A
Cited
GB784843A
Cited
GB883807A
Cited
US3053850A
Cited
US4039467A
Cited
US4330469A
Cited
US4267306A
Cited
US4359570A
Cited
US4403092A
Cited
US4732615A
Cited
JPS63307275A
Cited
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