US2004143041A1PendingUtilityA1
Polyester compositions
Priority: Jan 13, 2003Filed: Mar 5, 2003Published: Jul 22, 2004
Est. expiryJan 13, 2023(expired)· nominal 20-yr term from priority
C08K 5/34C08L 2205/02C08K 5/5393C08L 69/00C08L 67/02C08G 63/20C08K 5/5205C08K 5/524
49
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Claims
Abstract
Disclosed are polymer compositions comprising: (A) at least one polyester prepared by the reaction of at least one diol with at least one dicarboxylic acid or dialkyl ester thereof in the presence of a metallic catalyst; and (B) at least one salt prepared from the reaction of one or more acidic phosphorus-containing compounds and one or more basic organic compounds which contain nitrogen. The polyester compositions exhibit improved color, especially when used as a component of a polyester/polycarbonate blend. Also disclosed are polymer compositions comprising a polycarbonate in combination with components (A) and (B).
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A polymer composition comprising:
(A) at least one polyester prepared by the reaction of at least one diol with at least one dicarboxylic acid or dialkyl ester thereof in the presence of a metallic catalyst; and (B) at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds with one or more basic organic compounds which contain nitrogen.
2 . A polymer composition according to claim 1 wherein the acidic phosphorus compounds are selected from the compounds having the formulas:
wherein
R 1 and R 2 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl;
n is 2 to 500; and
X is selected from hydrogen and hydroxy; and wherein the basic organic compounds are selected from compounds having the formulas:
wherein
R 3 , R 4 , and R 5 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 , R 4 , and R 5 is a substituent other than hydrogen; R 3 and R 4 or R 4 and R 5 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;
R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl;
R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl;
R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula
R 12 is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl and may be located at the 2, 3 or 4 positions on the aromatic ring;
the —N(R 3 )(R 4 ) group may be located at the 2, 3 or 4 positions on the pyridine ring of nitrogen compound (5);
the —CO 2 R 3 and R 1 groups may be located at any of the 2, 3, 4, 5, 6 positions of the pyridine ring of nitrogen compound (6);
L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—;
L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene;
Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—;
Y 2 is selected from —O— or —N(R 1 )—;
R 13 and R 14 are independently selected from —O—R 2 , and —N(R 2 ) 2 ;
Z is a positive integer of up to about 20;
m1 is selected from 0 to about 10;
n1 is a positive integer selected from 2 to about 12;
R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures:
Radical A structures wherein * designates the position of attachment.
and wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
3 . A polymer composition according to claim 2 wherein the polyester of component (A) comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent.
4 . A polymer composition according to claim 2 wherein the polyester of component (A) comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains up to about 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent.
5 . A polymer composition comprising:
(A) at least one polyester comprising:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains about 10 to 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 0.01 to about 0.25 weight percent based on the total weight of the composition of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds selected from phosphorous acid, phosphoric acid and polyphosphoric acid with one or more basic organic compounds which contain nitrogen and have the formulas: wherein R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl; R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl; R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl; R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Y 2 is selected from —O— or —N(R 1 )—; Z is a positive integer of up to about 20; m1 is selected from 0 to about 10; n1 is a positive integer selected from 2 to about 12; R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures: Radical A structures wherein * designates the position of attachment. wherein at least one of R 15 and R 16 is an A radical; and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
6 . A composition according to claim 5 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 40 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 60 mole percent ethylene glycol residues;
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 5 wherein R 10 is hydrogen or alkyl and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
7 . The composition of claim 6 wherein the polyester of component (A) is has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 55 to 80 mole percent 1,4-cyclohexanedimethanol residues and 20 to about 45 mole percent ethylene glycol residues.
8 . A composition according to claim 5 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 65 to 83 mole percent terephthalic acid residues and about 35 to 17 mole percent isophthalic acid residues; and
(2) diol residues comprising about 80 to 100 mole percent 1,4-cyclohexanedimethanol residues and about 0 to about 20 mole percent ethylene glycol residues;
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 5 wherein R 10 is hydrogen or alkyl and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
9 . The composition of claim 8 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 70 to 80 mole percent terephthalic acid residues and about 30 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 90 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 10 mole percent ethylene glycol residues.
10 . A composition according to claim 5 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least about 80 mole percent 1,4-cyclohexanedicarboxylic acid residues; and
(2) diol residues comprising at least about 80 mole percent 1,4-cyclohexanedimethanol residues;
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 5 wherein R 10 is hydrogen or alkyl and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
11 . A composition according to claim 10 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 100 mole percent 1,4-cyclohexanedicarboxylic acid residues;
(2) diol residues comprising about 100 mole percent 1,4-cyclohexanedimethanol residues.
12 . A polymer composition comprising:
(A) at least one polyester having an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof; and contains about 10 to 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 0.01 to about 0.25 weight percent based on the total weight of the composition of at least one salt prepared by the reaction of phosphorous acid, with one or more basic organic compounds which contain nitrogen and have the formulas: wherein R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl; R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl; R 10 is selected from hydrogen and C 1 -C 22 -alkyl; L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Y 2 is selected from —O— or —N(R 1 )—; Z is a positive integer of up to about 6; m1 is selected from 0 to about 10; n1 is a positive integer selected from 2 to about 12; R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures: Radical A structures wherein * designates the position of attachment. wherein at least one of R 15 and R 16 represents an A radical; and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
13 . A composition according to claim 12 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 55 to 80 mole percent 1,4-cyclohexanedimethanol residues and 20 to about 45 mole percent ethylene glycol residues.
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 12 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
14 . A composition according to claim 12 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 70 to 80 mole percent terephthalic acid residues and about 30 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 90 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 10 mole percent ethylene glycol residues.
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 12 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
15 . A composition according to claim 12 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least about 90 mole percent 1,4-cyclohexanedicarboxylic acid residues; and
(2) diol residues comprising at least about 90 mole percent 1,4-cyclohexanedimethanol residues;
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 12 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
16 . A polymer composition comprising:
(A) at least one polyester having an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains about 10 to 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 0.01 to about 0.25 weight percent based on the total weight of the composition of at least one salt prepared by the reaction of phosphorous acid with a basic organic compound having the formula: wherein R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl; R 10 is selected from hydrogen and C 1 -C 22 -alkyl; L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; and L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Z is a positive integer of up to about 6.
17 . A composition according to claim 16 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 55 to 80 mole percent 1,4-cyclohexanedimethanol residues and 20 to about 45 mole percent ethylene glycol residues.
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of the salt defined in claim 16 wherein R 6 ═R 7 ═R 8 ═R 9 ═R 10 =methyl; L 1 is hexamethylene; and (R 3 )(R 4 )N— collectively represent a morpholino group and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
18 . A composition according to claim 16 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 70 to 80 mole percent terephthalic acid residues and about 30 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 90 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 10 mole percent ethylene glycol residues.
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of the salt defined in claim 16 wherein R 6 ═R 7 ═R 8 ═R 9 ═R 10 =methyl; L 1 is hexamethylene; and (R 3 )(R 4 )N— collectively represent a morpholino group and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
19 . A composition according to claim 16 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least about 90 mole percent 1,4-cyclohexanedicarboxylic acid residues; and
(2) diol residues comprising at least about 90 mole percent 1,4-cyclohexanedimethanol residues;
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 16 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
20 . A polymer composition comprising:
(A) at least one polyester prepared by the reaction of at least one diol with at least one dicarboxylic acid or dialkyl ester thereof in the presence of a metallic catalyst; (B) at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds with one or more basic organic compounds which contain nitrogen; and (C) a polycarbonate.
21 . A polymer composition according to claim 20 wherein the acidic phosphorus compounds are selected from the compounds having the formulas:
wherein
R 1 and R 2 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl;
n is 2 to 500; and
X is selected from hydrogen and hydroxy; and wherein the basic organic compounds are selected from compounds having the formulas:
wherein
R 3 , R 4 , and R 5 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 , R 4 , and R 5 is a substituent other than hydrogen; R 3 and R 4 or R 4 and R 5 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;
R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl;
R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl;
R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula
R 12 is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl and may be located at the 2, 3 or 4 positions on the aromatic ring;
the —N(R 3 )(R 4 ) group may be located at the 2, 3 or 4 positions on the pyridine ring of nitrogen compound (5);
the —CO 2 R 3 and R 1 groups may be located at any of the 2, 3, 4, 5, 6 positions of the pyridine ring of nitrogen compound (6);
L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—;
L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene;
Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—;
Y 2 is selected from —O— or —N(R 1 )—;
R 13 and R 14 are independently selected from —O—R 2 , and —N(R 2 ) 2 ;
Z is a positive integer of up to about 20;
m1 is selected from 0 to about 10;
n1 is a positive integer selected from 2 to about 12;
R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures:
Radical A structures wherein * designates the position of attachment.
and wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
22 . A polymer composition according to claim 21 wherein the polyester of component (A) comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent.
23 . A polymer composition according to claim 21 wherein the polyester of component (A) comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains up to about 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and component (C) comprises a bisphenol A polycarbonate, wherein the weight ratio of polyester component (A) to polycarbonate component (C) is about 75:25 to about 25:75.
24 . A polymer composition comprising:
(A) at least one polyester comprising:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains about 10 to 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 0.01 to about 0.25 weight percent based on the total weight of the composition of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds selected from phosphorous acid, phosphoric acid and polyphosphoric acid with one or more basic organic compounds which contain nitrogen and have the formulas: wherein R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl; R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl; R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl; R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Y 2 is selected from —O— or —N(R 1 )—; Z is a positive integer of up to about 20; m1 is selected from 0 to about 10; n1 is a positive integer selected from 2 to about 12; R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures: Radical A structures wherein * designates the position of attachment wherein at least one of R 15 and R 16 is an A radical; and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2; and (C) a polycarbonate, wherein the weight ratio of polyester component (A) to polycarbonate component (C) is about 75:25 to about 25:75.
25 . A composition according to claim 24 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 40 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 60 mole percent ethylene glycol residues;
component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 24 wherein R 10 is hydrogen or alkyl and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1; and component (C) comprises a bisphenol A polycarbonate.
26 . The composition of claim 25 wherein the polyester of component (A) is has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 55 to 80 mole percent 1,4-cyclohexanedimethanol residues and 20 to about 45 mole percent ethylene glycol residues.
27 . A composition according to claim 24 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 65 to 83 mole percent terephthalic acid residues and about 35 to 17 mole percent isophthalic acid residues; and
(2) diol residues comprising about 80 to 100 mole percent 1,4-cyclohexanedimethanol residues and about 0 to about 20 mole percent ethylene glycol residues;
component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 24 wherein R 10 is hydrogen or alkyl and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1; and component (C) comprises a bisphenol A polycarbonate.
28 . The composition of claim 27 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 70 to 80 mole percent terephthalic acid residues and about 30 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 90 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 10 mole percent ethylene glycol residues.
29 . A composition according to claim 24 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least about 80 mole percent 1,4-cyclohexanedicarboxylic acid residues; and
(2) diol residues comprising at least about 80 mole percent 1,4-cyclohexanedimethanol residues;
component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 24 wherein R 10 is hydrogen or alkyl and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1; and component (C) comprises a bisphenol A polycarbonate.
30 . A composition according to claim 29 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising 100 mole percent 1,4-cyclohexanedicarboxylic acid residues;
(2) diol residues comprising 100 mole percent 1,4-cyclohexanedimethanol residues.
31 . A polymer composition comprising:
(A) at least one polyester having an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains about 10 to 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 0.01 to about 0.25 weight percent based on the total weight of the composition of at least one salt prepared by the reaction of phosphorous acid with one or more basic organic compounds which contain nitrogen and have the formulas: wherein R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl; R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, R 10 is selected from hydrogen and C 1 -C 22 -alkyl; L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Y 2 is selected from —O— or —N(R 1 )—; Z is a positive integer of up to about 6; m1 is selected from 0 to about 10; n1 is a positive integer selected from 2 to about 12; R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures: Radical A structures wherein * designates the position of attachment. wherein at least one of R 15 and R 16 represents an A radical and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2; and (C) a polycarbonate, wherein the weight ratio of polyester component (A) to polycarbonate component (C) is about 75:25 to about 25:75.
32 . A composition according to claim 31 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 55 to 80 mole percent 1,4-cyclohexanedimethanol residues and 20 to about 45 mole percent ethylene glycol residues.
component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 31 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1; and component (C) comprises a bisphenol A polycarbonate.
33 . A composition according to claim 31 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 70 to 80 mole percent terephthalic acid residues and about 30 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 90 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 10 mole percent ethylene glycol residues.
component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 12 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1; and component (C) comprises a bisphenol A polycarbonate.
34 . A composition according to claim 31 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least about 90 mole percent 1,4-cyclohexanedicarboxylic acid residues; and
(2) diol residues comprising at least about 90 mole percent 1,4-cyclohexanedimethanol residues;
component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 31 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1; and component (C) comprises a bisphenol A polycarbonate.
35 . A polymer composition comprising:
(A) at least one polyester having an inherent viscosity of about 0.4 to 1.2 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and contains about 10 to 200 ppmw Ti, Co and/or Mn residues, wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 0.01 to about 0.25 weight percent based on the total weight of the composition of at least one salt prepared by the reaction of phosphorous acid with a basic organic compound having the formula: wherein R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl; R 10 is selected from hydrogen and alkyl; L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; and L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Z is a positive integer of up to about 6; and (C) a bisphenol A polycarbonate, wherein the weight ratio of polyester component (A) to polycarbonate component (C) is about 75:25 to about 25:75.
36 . A composition according to claim 35 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 80 to 100 mole percent terephthalic acid residues and about 0 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 55 to 80 mole percent 1,4-cyclohexanedimethanol residues and 20 to about 45 mole percent ethylene glycol residues.
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of the salt defined in claim 35 wherein R 6 ═R 7 ═R 8 ═R 9 ═R 10 =methyl; L, is hexamethylene; and (R 3 )(R 4 )N— collectively represent a morpholino group and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
37 . A composition according to claim 35 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising about 70 to 80 mole percent terephthalic acid residues and about 30 to 20 mole percent isophthalic acid residues; and
(2) diol residues comprising about 90 to 100 mole percent 1,4-cyclohexanedimethanol residues and 0 to about 10 mole percent ethylene glycol residues.
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of the salt defined in claim 16 wherein R 6 ═R 7 ═R 8 ═R 9 ═R 10 =methyl; L 1 is hexamethylene; and (R 3 )(R 4 )N— collectively represent a morpholino group and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
38 . A composition according to claim 35 wherein the polyester of component (A) has an inherent viscosity of about 0.4 to 0.8 dL/g measured at 25° C. in a 60/40 ratio by weight of phenol/tetrachloroethane and comprises:
(1) diacid residues comprising at least about 90 mole percent 1,4-cyclohexanedicarboxylic acid residues; and
(2) diol residues comprising at least about 90 mole percent 1,4-cyclohexanedimethanol residues;
and component (B) comprises about 0.05 to about 0.15 weight percent based on the total weight of the composition of at least one salt defined in claim 35 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.25 to about 1.1.
39 . A polymer concentrate comprising:
(A) at least one polyester prepared by the reaction of at least one diol with at least one dicarboxylic acid or dialkyl ester thereof in the presence of a metallic catalyst; and (B) up to about 10 weight percent, based on the total weight of the polyester, of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds and one or more basic organic compounds which contain nitrogen.
40 . A polymer concentrate according to claim 39 comprising:
(A) a polyester comprising:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and up to about 200 ppmw Ti, Co and/or Mn residues;
wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 5 to about 10 weight percent, based on the total weight of the polyester, of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds with one or more basic organic compounds which contain nitrogen;
wherein
the acidic phosphorus compounds are selected from the compounds having the formula:
wherein
R 1 and R 2 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl;
n is 2 to 500; and
X is selected from hydrogen and hydroxy;
and wherein the basic organic compounds are selected from compounds having the formulas:
wherein
R 3 , R 4 , and R 5 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 , R 4 , and R 5 is a substituent other than hydrogen; R 3 and R 4 or R 4 and R 5 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;
R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl;
R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl;
R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula
R 12 is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl and may be located at the 2, 3 or 4 positions on the aromatic ring;
the —N(R 3 )(R 4 ) group may be located at the 2, 3 or 4 positions on the pyridine ring of nitrogen compound (5);
the —CO 2 R 3 and R 1 groups may be located at any of the 2, 3, 4, 5, 6 positions of the pyridine ring of nitrogen compound (6);
L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—;
L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene;
Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—;
Y 2 is selected from —O— or —N(R 1 )—;
R 13 and R 14 are independently selected from —O—R 2 , and —N(R 2 ) 2 ;
Z is a positive integer of up to about 20;
m1 is selected from 0 to about 10;
n1 is a positive integer selected from 2 to about 12;
R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures:
Radical A structures wherein * designates the position of attachment.
and wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
41 . A polymer concentrate according to claim 39 comprising:
(A) a polyester comprising:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and up to about 200 ppmw Ti, Co and/or Mn residues; wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 5 to about 10 weight percent, based on the total weight of the polyester, of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds with one or more basic organic compounds which contain nitrogen;
wherein
the acidic phosphorus compounds are selected from phosphorous acid, phosphoric acid and polyphosphoric acid; and
the basic organic compounds which contain nitrogen are selected from compounds having the formulas:
wherein
R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl;
R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;
R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl;
R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl;
R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula
L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—;
L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene;
Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—;
Y 2 is selected from —O— or —N(R 1 )—;
Z is a positive integer of up to about 20;
m1 is selected from 0 to about 10;
n1 is a positive integer selected from 2 to about 12;
R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures:
Radical A structures wherein * designates the position of attachment.
wherein at least one of R 15 and R 16 is an A radical; and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
42 . A polymer concentrate according to claim 39 comprising:
(A) a polyester comprising:
(1) diacid residues comprising at least 50 mole percent terephthalic acid residues, 1,4-cyclohexanedicarboxylic acid residues or a mixture thereof; and
(2) diol residues comprising at least 50 mole percent of ethylene glycol residues, cyclohexanedimethanol residues, or a mixture thereof;
and up to about 200 ppmw Ti, Co and/or Mn residues;
wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 5 to about 10 weight percent, based on the total weight of the polyester, of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds with one or more basic organic compounds which contain nitrogen;
wherein
the acidic phosphorus compounds is phosphorous acid; and
the basic organic compounds which contain nitrogen are selected from compounds having the formulas:
wherein
R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl;
R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;
R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl;
R 10 is selected from hydrogen and alkyl;
L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—;
L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene;
Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—;
Y 2 is selected from —O— or —N(R 1 )—;
Z is a positive integer of up to about 6;
m1 is selected from 0 to about 10;
n1 is a positive integer selected from 2 to about 12;
R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures:
Radical A structures wherein * designates the position of attachment.
wherein at least one of R 15 and R 16 represents an A radical and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
43 . A polymer composition comprising:
(A) at least one polyester comprising:
(1) diacid residues comprising at least 40 mole percent terephthalic acid residues; and
(2) diol residues comprising from 52 to 75 mole percent of 1,4-cyclohexanedimethanol residues and 25 to 48 mole percent of ethylene glycol;
wherein the total mole percent of the diacid residues is equal to 100 mole percent and the total mole percent of the diol residues is also equal to 100 mole percent;
(B) at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds selected from phosphorous acid, phosphoric acid and polyphosphoric acid with one or more basic organic compounds which contain nitrogen and have the formulas: wherein R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl; R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached; R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl; R 10 is selected from hydrogen, —OR 6 , C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl; R 11 is selected from hydrogen; C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, —Y 1 —R 3 or a succinimido group having the formula L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—; L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene; Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—; Y 2 is selected from —O— or —N(R 1 )—; Z is a positive integer of up to about 20; m1 is selected from 0 to about 10; n1 is a positive integer selected from 2 to about 12; R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures: Radical A structures wherein * designates the position of attachment wherein at least one of R 15 and R 16 is an A radical; and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.
44 . The polymer composition of claim 43 further comprising a polycarbonate.
45 . The polymer compositon of claim 44 wherein the weight ratio of polyester component (A) to the polycarbonate component is about 75:25 to about 25:75.
46 . A polymer concentrate according to claim 44 comprising:
(A) a polyester comprising:
(1) diacid residues comprising from 80 to 100 mole percent terephthalic acid residues,; and
(2) diol residues comprising from 52 to 65 mole percent of 1,4-cyclohexanedimethanol residues, and 35 to 48 mole percent of ethylene glycol;
wherein the total of the diacid residues is equal to 100 mole percent and the total of the diol residues also is equal to 100 mole percent; and
(B) about 5 to about 10 weight percent, based on the total weight of the polyester, of at least one salt prepared by the reaction of one or more acidic phosphorus-containing compounds with one or more basic organic compounds which contain nitrogen;
wherein
the acidic phosphorus compounds is phosphorous acid; and
the basic organic compounds which contain nitrogen are selected from compounds having the formulas:
wherein
R 1 and R 2 are independently is selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, and aryl;
R 3 and R 4 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, and substituted C 3 -C 8 -cycloalkyl wherein at least one of R 3 and R 4 is a substituent other than hydrogen; R 3 and R 4 collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;
R 6 , R 7 , R 8 , and R 9 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl;
R 10 is selected from hydrogen and alkyl;
L 1 is a divalent linking group selected from C 2 -C 22 -alkylene; —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 —; C 3 -C 8 -cycloalkylene; arylene; or —CO—L 2 —OC—;
L 2 is selected from C 1 -C 22 -alkylene, arylene, —(CH 2 CH 2 —Y 1 ) 1-3 —CH 2 CH 2 — and C 3 -C 8 -cycloalkylene;
Y 1 is selected from —OC(O)—, —NHC(O)—, —O—, —S—, —N(R 1 )—;
Y 2 is selected from —O— or —N(R 1 )—;
Z is a positive integer of up to about 6;
m1 is selected from 0 to about 10;
n1 is a positive integer selected from 2 to about 12;
R 15 and R 16 are independently selected from hydrogen, C 1 -C 22 -alkyl, substituted C 1 -C 22 -alkyl, C 3 -C 8 -cycloalkyl, substituted C 3 -C 8 -cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures:
Radical A structures wherein * designates the position of attachment.
wherein at least one of R 15 and R 16 represents an A radical and the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to number of basic nitrogen atoms in the basic organic compound is about 0.05 to about 2.Join the waitlist — get patent alerts
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