US3872183A
Expired / Lapsed
US
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Copolyester resin containing anion attractive groups
Assignee: Goodyear Tire and Rubber Co
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Filing: 1973-07-02
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Granted: 1975-03-18
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Expires: 1993-07-02
Abstract
Abstract Copolyesters containing monohydroxyamine salts of oxalic acid or dihydroxyamine salts of organic aliphatic dicarboxylic acids in which the carboxyl groups are separated by at least two carbon atoms can be formed into fibers that dye to deep shades with acid type dyes. From about 1 to about 15 mol percent of the amine salt is used based on the total mols of acid units in the polyester exclusive of the acid in the amine salt itself. The invention encompasses random copolyesters as well as block copolyesters, both of which have improved anionic dyeability. Fibers of such copolyesters can be dyed to deep shades in solvents such as chlorobenzene or in strong acetic acid solutions. Dyeing can also be accomplished in aqueous dye solutions with or without the use of pressure. Dyeing in acidic medium gives excellent results.
Inventors
- 👤 Max H Keck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:40
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/68; C08G63/685; C08G63/6854; C08G63/6856; Y; Y10; Y10S; Y10S8/00; Y10S8/04
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
145 words
A THERMOPLASTIC POLYMERIC FIBER FORMING POLYESTER RESIN HAVING THE CAPABILITY OF BEING DYED BY ANIONIC DYES WHICH COMPRISES A FIBER FORMING POLYESTER RESIN DERIVED FROM DICARBOYLIC ACIDS OR ESTER FORMING DERIVATIVES THEREOF AND GLYCOLS AND CONTAINING AS A PART OF THE POLYMERIC POLYESTER MOLECULES AN ANION ATTRACTIVE GROUP THAT HAS ASSOCIATIVE PROPERTIES SUFFICIENTYL STRONG THAT INTERACTION OCCURS BETWEEN ANION ATTRACTIVE GROUPS OF THE POLYMER MOLECULES, SAID ANION ATTRACTIVE GROUP IS DERIVED FROM COMPOUNDS SELECTED FROM THE GROUP CONSISTING OF MONOHYDROXYAMINE SALTS OF OXALIC ACID AND DIHYDROXYAMINE SALTS OF ORGANIC DICARBOXYLIC ACIDS IN WHICH THE CARBOXYL GROUPS ARE SEPARATED BY AT LEAST TWO CARBON ATOMS AND, SAID AMINE SALTS ARE USED IN AMOUNTS TO PROVIDE FROM ABOUT 1 TO ABOUT 15 MOL PERCENT OF AMINE UNITS BASED ON THE TOTAL MOLS OF ACID UNITS IN THE POLYESTER EXCLUSIVE OF THE ACID UNITS IN THE AMINE SALT.
Claim 2
Dependent Claim
145 words
A THERMOPLASTIC POLYMERIC FIBER FORMING POLYESTER RESIN HAVING THE CAPABILITY OF BEING DYED BY ANIONIC DYES WHICH COMPRISES A FIBER FORMING POLYESTER RESIN DERIVED FROM DICARBOYLIC ACIDS OR ESTER FORMING DERIVATIVES THEREOF AND GLYCOLS AND CONTAINING AS A PART OF THE POLYMERIC POLYESTER MOLECULES AN ANION ATTRACTIVE GROUP THAT HAS ASSOCIATIVE PROPERTIES SUFFICIENTYL STRONG THAT INTERACTION OCCURS BETWEEN ANION ATTRACTIVE GROUPS OF THE POLYMER MOLECULES, SAID ANION ATTRACTIVE GROUP IS DERIVED FROM COMPOUNDS SELECTED FROM THE GROUP CONSISTING OF MONOHYDROXYAMINE SALTS OF OXALIC ACID AND DIHYDROXYAMINE SALTS OF ORGANIC DICARBOXYLIC ACIDS IN WHICH THE CARBOXYL GROUPS ARE SEPARATED BY AT LEAST TWO CARBON ATOMS AND, SAID AMINE SALTS ARE USED IN AMOUNTS TO PROVIDE FROM ABOUT 1 TO ABOUT 15 MOL PERCENT OF AMINE UNITS BASED ON THE TOTAL MOLS OF ACID UNITS IN THE POLYESTER EXCLUSIVE OF THE ACID UNITS IN THE AMINE SALT.
Claim 3
Dependent Claim
78 words
A composition comprising a fiber forming copolyester of (A) units selected from the group consisting of polyalkylene terephthalate, polycycloalkylene terephthalate, polyalkylene naphthalate, polycycloalkylene naphthalate, polyalkylene terephthalate copolyesters containing at least 80 mol percent of polyalkylene terephthalate and polyalkylene naphthalate copolyesters containing at least 80 mol percent of polyalkylene naphthalate and (B) units selected from the group consisting of (I) an amine salt of oxalic acid wherein the amine is a member of the class having the general formula
Claim 4
Dependent Claim
78 words
A composition comprising a fiber forming copolyester of (A) units selected from the group consisting of polyalkylene terephthalate, polycycloalkylene terephthalate, polyalkylene naphthalate, polycycloalkylene naphthalate, polyalkylene terephthalate copolyesters containing at least 80 mol percent of polyalkylene terephthalate and polyalkylene naphthalate copolyesters containing at least 80 mol percent of polyalkylene naphthalate and (B) units selected from the group consisting of (I) an amine salt of oxalic acid wherein the amine is a member of the class having the general formula
Claim 5
Dependent Claim
117 words
A random copolymer comprising (A) units of a polymer selected from the group consisting of polyalkylene terephthalate, polycycloalkylene terephthalate, polyalkylene naphthalate, polycycloalkylene terephthalate, polyalkylene terephthalate copolyesters containing at least 80 mol percent of polyalkylene terephthalate and polyalkylene naphthalate copolyesters containing at least 80 mol percent of polyalkylene naphthalate and (B) units derived from an N-substituted dialkanolamine salt of an aliphatic dicarboxylic acid, said aliphatic dicarboxylic acid having at least two carbon atoms in the chain between the carboxyl groups, in which the (A) units in the copolyester comprise from 99 to 85 percent of the sum of the (A) units and the (B) units, and the (B) units comprise from 1 to 15 percent of said sum.
Claim 6
Dependent Claim
117 words
A random copolymer comprising (A) units of a polymer selected from the group consisting of polyalkylene terephthalate, polycycloalkylene terephthalate, polyalkylene naphthalate, polycycloalkylene terephthalate, polyalkylene terephthalate copolyesters containing at least 80 mol percent of polyalkylene terephthalate and polyalkylene naphthalate copolyesters containing at least 80 mol percent of polyalkylene naphthalate and (B) units derived from an N-substituted dialkanolamine salt of an aliphatic dicarboxylic acid, said aliphatic dicarboxylic acid having at least two carbon atoms in the chain between the carboxyl groups, in which the (A) units in the copolyester comprise from 99 to 85 percent of the sum of the (A) units and the (B) units, and the (B) units comprise from 1 to 15 percent of said sum.
Claim 7
Dependent Claim
14 words
The copolymer of claim 3 in which the (A) units are ethylene terephthalate units.
Claim 8
Dependent Claim
45 words
The copolymer of claim 3 in which the (B) units are units derived from an N-substituted dialkanolamine and an aliphatic dicarboxylic acid selected from the group consisting of aliphatic dicarboxylic acids containing from two to 10 carbon atoms between the carboxyl groups of said acids.
Claim 9
Dependent Claim
34 words
The copolymer of claim 3 modified with from 0.1 to 1.5 mol percent of a modifying agent selected from the group consisting of ethylene glycol, propylene glycol, tetramethylene glycol, neopentyl glycol and polyglycol ethers.
Claim 10
Dependent Claim
33 words
A copolymer of claim 3 in which the copolyester is a random copolyester containing from 1 to 15 mol percent of the amine based on the total mols of acid in the copolyester.
Claim 11
Dependent Claim
49 words
A copolymer according to claim 3 in which the units of amine salts are selected from the group consisting of glutaric acid salt of tertiary butyl diethanolamine, succinic acid salt of tertiary butyl diethanolamine, pimelic acid salt of tertiary butyl diethanolamine and azelaic acid salt of tertiary butyl diethanolamine.
Claim 12
Dependent Claim
23 words
A composition according to claim 2 wherein the (A) units are ethylene terephthalate and the (B) units are oxalate salt of N-2-(hydroxyethyl) cyclohexylamine.
Claim 13
Dependent Claim
24 words
A copolymer according to claim 3 wherein the (A) units are ethylene terephthalate and the (B) units are derived from tertiary butyl diethanolamine glutarate.
Claim 14
Dependent Claim
24 words
A copolymer according to claim 3 wherein the (A) units are ethylene terephthalate and the (B) units are derived from tertiary butyl diethanolamine pimelate.
Claim 15
Dependent Claim
24 words
A composition according to claim 2 wherein the (A) units are ethylene terephthalate and the (B) units are derived from tertiary butyl diethanolamine azelate.
Claim 16
Dependent Claim
123 words
A composition comprising a fiber forming block copolyester in which the blocks are (A) linear crystallizable polyalkylene terephthalate, polycycloalkylene terephthalate, polyalkylene naphthalate, polycycloalkylene naphthalate, a polyalkylene terephthalate or naphthalate copolymer containing at least 80 mol percent of polyalkylene terephthalate or naphthalate, said units having a melting point of at least 200* C. and (B) a copolyester of a glycol and 5 to 95 mol percent of a difunctional tertiary amine salt of an aliphatic organic dicarboxylic acid in which the carboxyl groups are separated by at least two carbon atoms and an aromatic dicarboxylic acid or mixture of said aromatic dicarboxylic acid with up to 65 mol percent of an aliphatic dicarboxylic acid, the amine being selected from amines having the general formula
Claim 17
Dependent Claim
123 words
A composition comprising a fiber forming block copolyester in which the blocks are (A) linear crystallizable polyalkylene terephthalate, polycycloalkylene terephthalate, polyalkylene naphthalate, polycycloalkylene naphthalate, a polyalkylene terephthalate or naphthalate copolymer containing at least 80 mol percent of polyalkylene terephthalate or naphthalate, said units having a melting point of at least 200* C. and (B) a copolyester of a glycol and 5 to 95 mol percent of a difunctional tertiary amine salt of an aliphatic organic dicarboxylic acid in which the carboxyl groups are separated by at least two carbon atoms and an aromatic dicarboxylic acid or mixture of said aromatic dicarboxylic acid with up to 65 mol percent of an aliphatic dicarboxylic acid, the amine being selected from amines having the general formula
Claim 18
Dependent Claim
28 words
A block copolyester according to claim 13 in which the (A) units are ethylene terephthalate units and the (B) units are units derived from tertiary butyl diethanolamine glutarate.
Claim 19
Dependent Claim
28 words
A block copolyester according to claim 13 in which the (A) units are ethylene terephthalate units and the (B) units are units derived from tertiary butyl diethanolamine pimelate.
Claim 20
Dependent Claim
28 words
A block copolyester according to claim 13 in which the (A) units are ethylene terephthalate units and the (B) units are units derived from tertiary butyl diethanolamine azelate.
Claim 21
Dependent Claim
36 words
A block copolyester according to claim 13 in which the blocks of the (A) units comprise ethylene terephthalate units and the (B) units comprise blocks of units derived from a glycol, azelaic and tertiary butyl diethanolamine.
Claim 22
Dependent Claim
42 words
A block copolyester in which the blocks of (A) units comprise ethylene terephthalate units and the blocks of (B) units comprise blocks of units derived from a glycol and the pimelate salt of a monoether derivative of triethanolamine and a dicarboxylic acid.
Claim 23
Dependent Claim
42 words
A block copolyester in which the blocks of (A) units comprise ethylene terephthalate units and the blocks of (B) units comprise blocks of units derived from a glycol and the pimelate salt of a monoether derivative of triethanolamine and a dicarboxylic acid.
Claim 24
Dependent Claim
52 words
A block copolyester in which the blocks of (A) units comprise ethylene terephthalate units and the blocks of (B) units comprise blocks of units derived from a glycol and an acid selected from terephthalic acid and isophthalic acid and the azelate salt of a monoether derivative of triethanolamine and a dicarboxylic acid.
Claim 25
Dependent Claim
52 words
A block copolyester in which the blocks of (A) units comprise ethylene terephthalate units and the blocks of (B) units comprise blocks of units derived from a glycol and an acid selected from terephthalic acid and isophthalic acid and the azelate salt of a monoether derivative of triethanolamine and a dicarboxylic acid.
Claim 26
Dependent Claim
33 words
A composition of claim 9 in which the copolyester is a block copolyester containing from 1 to 15 mol percent of the amine based on the total mols of acid in the copolyester.
Claim 27
Dependent Claim
104 words
The process which comprises forming glycol esters of an acid selected from the group consisting of (A) terephthalic acid and naphthalic acid and mixtures of these acids with another acid selected from the group consisting of (B) isophthalic acid and an aliphatic dicarboxylic acid containing from two to 12 carbon atoms, said mixtures comprising at least 80 mol percent of the (A) acid and condensing said glycol esters with an oxalic acid salt of an N-substituted monoalkanolamine, with the elimination of glycol, to form a polymer having an intrinsic viscosity of at least 0.4 measured in a 60/40 tetrAchloroethane mixed solvent at 30.0* C.
Claim 28
Dependent Claim
104 words
The process which comprises forming glycol esters of an acid selected from the group consisting of (A) terephthalic acid and naphthalic acid and mixtures of these acids with another acid selected from the group consisting of (B) isophthalic acid and an aliphatic dicarboxylic acid containing from two to 12 carbon atoms, said mixtures comprising at least 80 mol percent of the (A) acid and condensing said glycol esters with an oxalic acid salt of an N-substituted monoalkanolamine, with the elimination of glycol, to form a polymer having an intrinsic viscosity of at least 0.4 measured in a 60/40 tetrAchloroethane mixed solvent at 30.0* C.
Claim 29
Dependent Claim
133 words
The process which comprises forming glycol esters of an acid selected from the group consisting of (A) terephthalic acid and naphthalic acid and mixtures of these acids with another acid selected from the group consisting of (B) isophthalic acid and an aliphatic dicarboxylic acid containing from two to 12 carbon atoms, said mixtures comprising at least 80 mol percent of the (A) acid and condensing said glycol esters with an amine salt of an acid selected from the group consisting of aliphatic dicarboxylic acids having from 2 to 10 carbon atoms between carboxyl groups, HCl and H2SO4, the amine of said salt being an N-substituted dialkanolamine, with the elimination of glycol to form a polymer having an intrinsic viscosity of at least 0.4 measured in a 60/40 phenoltetrachloroethane mixed solvent at 30.0* C.
Claim 30
Dependent Claim
133 words
The process which comprises forming glycol esters of an acid selected from the group consisting of (A) terephthalic acid and naphthalic acid and mixtures of these acids with another acid selected from the group consisting of (B) isophthalic acid and an aliphatic dicarboxylic acid containing from two to 12 carbon atoms, said mixtures comprising at least 80 mol percent of the (A) acid and condensing said glycol esters with an amine salt of an acid selected from the group consisting of aliphatic dicarboxylic acids having from 2 to 10 carbon atoms between carboxyl groups, HCl and H2SO4, the amine of said salt being an N-substituted dialkanolamine, with the elimination of glycol to form a polymer having an intrinsic viscosity of at least 0.4 measured in a 60/40 phenoltetrachloroethane mixed solvent at 30.0* C.
Claim 31
Dependent Claim
89 words
The process which comprises forming bis hydroxyethyl terephthalate, adding from about 1 to about 15 mol percent based on the terephthalate present of (I) an amine salt of an organic dicarboxylic acid selected from the group consisting of salts of a monohydroxyamine with oxalic acid and (II) salts of a difunctional amine with an aliphatic organic dicarboxylic acid in which the carboxyl groups of said dicarboxylic acid are separated by at least two carbon atoms, the amine of (I) being selected from amines having a general formula selected from
Claim 32
Dependent Claim
89 words
The process which comprises forming bis hydroxyethyl terephthalate, adding from about 1 to about 15 mol percent based on the terephthalate present of (I) an amine salt of an organic dicarboxylic acid selected from the group consisting of salts of a monohydroxyamine with oxalic acid and (II) salts of a difunctional amine with an aliphatic organic dicarboxylic acid in which the carboxyl groups of said dicarboxylic acid are separated by at least two carbon atoms, the amine of (I) being selected from amines having a general formula selected from
Claim 33
Dependent Claim
21 words
The process of claim 21 wherein the succinic acid salt of tertiary butyl diethanolamine is used as the anion attractive group.
Claim 34
Dependent Claim
21 words
The process of claim 21 wherein the pimelic acid salt of tertiary butyl diethanolamine is used as the anion attractive group.
Claim 35
Dependent Claim
30 words
The process of claim 22 in which the bis hydroxyethyl terephthalate is formed from dimethyl terephthalate and ethylene glycol by ester interchange in the presence of zinc acetate as catalyst.
Claim 36
Dependent Claim
19 words
The process of claim 21 wherein (A) a salt of the monoether derivative of triethanolamine of the general type.
Claim 37
Dependent Claim
23 words
The process of claim 22 in which said glycol esters are prepared by ester interchange in the presence of a zinc containing catalyst.
Claim 38
Dependent Claim
42 words
The process which comprises forming bis hydroxyethyl terephthalate, adding from about 1 to about 15 mol percent based on the terephthalate units present of an anion attractive group comprising an amine salt of oxalic acid wherein the amine of the general type
Claim 39
Dependent Claim
42 words
The process which comprises forming bis hydroxyethyl terephthalate, adding from about 1 to about 15 mol percent based on the terephthalate units present of an anion attractive group comprising an amine salt of oxalic acid wherein the amine of the general type
Claim 40
Dependent Claim
61 words
The process of claim 29 wherein the anion attractive groups is a salt of an acid selected from the group consisting of HCL, H2SO4, and an aliphatic organic dicarboxylic acid containing from two to 10 carbon atoms, separating the carboxyl groups with an N-substituted dialkanolamine including dipropanolamines, dibutanolamines and dihexanolamines which are N-substituted with groups selected from alkyl or cycloalkyl radicals.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-03-17 | 1978-09-16 | 1979-03-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-03-17 | 1982-09-16 | 1983-03-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-03-17 | 1986-09-16 | 1987-03-18 | $7700.00 | Window Closed / Lapsed |