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US5372864A Expired / Lapsed US ⏱️ 0.0 years remaining

Toners for polyesters

Assignee: Eastman Chemical Co
•
Filing: 1993-09-03
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Granted: 1994-12-13
•
Expires: 2013-09-03
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Abstract

Abstract This invention provides certain blue substituted 1,4-bis(2,6-dialkylanilino) anthraquinones in combination with selected red anthraquinone and anthrapyridone (3H-dibenz[f,ij] isoquinoline-2,7-dione) compounds which provide a toner system useful in imparting a desirable neutral to slightly blue hue to polyesters having a yellow appearance. The thermally stable colored compounds can have polyester reactive groups and are preferably incorporated into the polyester polymer structure during polymerization.

Inventors

  • 👤 Max A. Weaver
  • 👤 Wayne P. Pruett
  • 👤 Gerry Rhodes
  • 👤 Samuel D. Hilbert
  • 👤 William W. Parham

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 19:57
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/68; C08G63/685; C08G63/6854; C08G63/6856; C08G63/688; C08G63/6884; C08G63/6886; C09; C09B; C09B67/00; C09B67/0033; C09B67/0034; C09B67/0038; Y; Y10; Y10T; Y10T428/00; Y10T428/13; Y10T428/1352; Y10T428/1397

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 603 words
A molding or fiber grade polyester having copolymerized therein, in an amount sufficient to improve the apparent whiteness of the polyester, at least one blue 1,4-bis(2,6-dialkylanilino) anthraquinone compound of Formula (I) ##STR52## wherein: R is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, halogen, carboxy, and C 1 -C 6 ##STR53## R 1 and R 2 are independently C 1 -C 6 -alkyl; R 3 is selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 alkyl, hydroxy, C 1 -C 6 -alkoxy, substituted C 1 -C 6 -alkoxy, cyano, thiocyano, C 1 -C 6 -alkylthio, substituted C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfonyl, substituted C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkoxycarbonyl, carboxy, aryloxy, arylthio, arylsulfonyl, and SO 2 N(R 4 )R 5 X when m and/or n are zero; R 4 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 7 -cycloalkyl and aryl; R 5 is a linking group selected from the group consisting of C 1 -C 8 -alkylene, C 1 -C 6 -alkylene-Z--C 1 -C 6 -alkylene, arylene-C 1 -C 6 -alkylene, arylene-Z--C 1 -C 6 alkylene, C 3 -C 7 -cycloalkylene, C 1 -C 6 -alkylene-cycloalkylene-C 1 -C 6 -alkylene, C 1 -C 6 -alkylene-arylene-C 1 -C 6 -alkylene, and C 1 -C 6 -alkylene-Z-arylene-Z--C 1 -C 6 -alkylene, wherein Z is selected from --O--, --S-- and SO 2 ; X is hydrogen or a polyester reactive group; and m and n are independently 0 or 1; with the proviso that at least one polyester reactive group is present; along with at least one red anthraquinone or anthrapyridone compound selected from formulae (II)-(X) below: ##STR54## wherein: R 6 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 7 is hydrogen or one to three groups selected from C 1 -C 6 -alkyl, C 1 -C 6 -substituted alkyl, C 1 -C 6 -alkanoylamino, halogen, C 1 -C 6 -alkyl C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio; R 8 and R 9 are the same or different and are selected from the group consisting of C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 10 is selected from the group consisting of C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 11 is selected from the group consisting of hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 12 is hydrogen or one to three groups selected from the group consisting of C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, substituted C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, substituted C 1 -C 6 -alkylthio, halogen, hydroxy, C 1 -C 6 -alkanoylamino, aroylamino, C 1 -C 6 -alkylsulfonylamino and arylsulfonylamino; R 13 and R 14 are selected from hydrogen, cyano and CO 2 R 10 ; R 15 is R 4 or R 5 X as previously defined; L is --CO-- or --SO 2 --; X is as previously defined; m is 0 or 1; and p is 1 or 2; with the provisos that R 13 is hydrogen when m is 0 and at least one polyester reactive group is present.
Claim 2
Dependent Claim 603 words
A molding or fiber grade polyester having copolymerized therein, in an amount sufficient to improve the apparent whiteness of the polyester, at least one blue 1,4-bis(2,6-dialkylanilino) anthraquinone compound of Formula (I) ##STR52## wherein: R is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, halogen, carboxy, and C 1 -C 6 ##STR53## R 1 and R 2 are independently C 1 -C 6 -alkyl; R 3 is selected from the group consisting of hydrogen, halogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 alkyl, hydroxy, C 1 -C 6 -alkoxy, substituted C 1 -C 6 -alkoxy, cyano, thiocyano, C 1 -C 6 -alkylthio, substituted C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfonyl, substituted C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkoxycarbonyl, carboxy, aryloxy, arylthio, arylsulfonyl, and SO 2 N(R 4 )R 5 X when m and/or n are zero; R 4 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 7 -cycloalkyl and aryl; R 5 is a linking group selected from the group consisting of C 1 -C 8 -alkylene, C 1 -C 6 -alkylene-Z--C 1 -C 6 -alkylene, arylene-C 1 -C 6 -alkylene, arylene-Z--C 1 -C 6 alkylene, C 3 -C 7 -cycloalkylene, C 1 -C 6 -alkylene-cycloalkylene-C 1 -C 6 -alkylene, C 1 -C 6 -alkylene-arylene-C 1 -C 6 -alkylene, and C 1 -C 6 -alkylene-Z-arylene-Z--C 1 -C 6 -alkylene, wherein Z is selected from --O--, --S-- and SO 2 ; X is hydrogen or a polyester reactive group; and m and n are independently 0 or 1; with the proviso that at least one polyester reactive group is present; along with at least one red anthraquinone or anthrapyridone compound selected from formulae (II)-(X) below: ##STR54## wherein: R 6 is selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 7 is hydrogen or one to three groups selected from C 1 -C 6 -alkyl, C 1 -C 6 -substituted alkyl, C 1 -C 6 -alkanoylamino, halogen, C 1 -C 6 -alkyl C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio; R 8 and R 9 are the same or different and are selected from the group consisting of C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 10 is selected from the group consisting of C 1 -C 6 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 11 is selected from the group consisting of hydrogen, C 1 -C 12 -alkyl, substituted C 1 -C 12 -alkyl, C 3 -C 7 -cycloalkyl and aryl; R 12 is hydrogen or one to three groups selected from the group consisting of C 1 -C 6 -alkyl, substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, substituted C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, substituted C 1 -C 6 -alkylthio, halogen, hydroxy, C 1 -C 6 -alkanoylamino, aroylamino, C 1 -C 6 -alkylsulfonylamino and arylsulfonylamino; R 13 and R 14 are selected from hydrogen, cyano and CO 2 R 10 ; R 15 is R 4 or R 5 X as previously defined; L is --CO-- or --SO 2 --; X is as previously defined; m is 0 or 1; and p is 1 or 2; with the provisos that R 13 is hydrogen when m is 0 and at least one polyester reactive group is present.
Claim 3
Dependent Claim 115 words
The polyester of claim 1, wherein the blue anthraquinone compound(s) correspond to structure (I) above, wherein R is hydrogen; R 1 and R 2 are independently selected from methyl and ethyl; R 3 is hydrogen, methyl, or bromo; R 4 is hydrogen, C 1 -C 4 -alkyl and aryl; R 5 is selected from the group consisting of C 1 -C 6 -alkylene, C 1 -C 4 -alkylene-O--C 1 -C 4 -alkylene, --CH 2 C 6 H 10 CH 2 --, arylene, or --CH 2 -arylene- and the red component corresponds to formulae (V), wherein R 7 is C 1 -C 6 -alkoxy and R 4 and R 5 are as defined in claim 1.
Claim 4
Dependent Claim 24 words
The polyester of claim 1, wherein the concentration of blue and red compounds taken together is from about 0.5 ppm to about 10 ppm.
Claim 5
Dependent Claim 30 words
The polyester of claim 1, wherein the total concentration of blue compound(s) is about 1 to 7 ppm and the concentration of red compound(s) is about 0.5 to 3 ppm.
Claim 6
Dependent Claim 13 words
The polyester of claim 1, wherein the compound of formula (I) is ##STR55##
Claim 7
Dependent Claim 13 words
The polyester of claim 1, wherein the compound of formula (I) is ##STR56##
Claim 8
Dependent Claim 14 words
The polyester of claim 1, wherein the red compound of formula (V) is ##STR57##
Claim 9
Dependent Claim 14 words
The polyester of claim 1, wherein the red compound of formula (V) is ##STR58##
Claim 10
Dependent Claim 24 words
The polyester of claim 1, wherein the blue compound of formula (I) is ##STR59## and wherein the red compound of formula (V) is ##STR60##
Claim 11
Dependent Claim 14 words
The polyester of claim 1, wherein the red compound of formula (II) is ##STR61##
Claim 12
Dependent Claim 14 words
The polyester of claim 1, wherein the red compound of formula (III) is ##STR62##
Claim 13
Dependent Claim 14 words
The polyester of claim 1, wherein the red compound of formula (VI) is ##STR63##
Claim 14
Dependent Claim 14 words
The polyester of claim 1, wherein the red compound of formula (VIII) is ##STR64##
Claim 15
Dependent Claim 12 words
A shaped or formed article comprised of the polyester of claim 1.
Claim 16
Dependent Claim 9 words
A container comprised of the polyester of claim 1.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-12-12 1998-06-13 1998-12-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-12-12 2002-06-13 2002-12-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-12-12 2006-06-13 2006-12-13 $7700.00 Window Closed / Lapsed

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