GB1111895A - Process for the mass coloration of polyesters - Google Patents

Process for the mass coloration of polyesters

Info

Publication number
GB1111895A
GB1111895A GB1176066A GB1176066A GB1111895A GB 1111895 A GB1111895 A GB 1111895A GB 1176066 A GB1176066 A GB 1176066A GB 1176066 A GB1176066 A GB 1176066A GB 1111895 A GB1111895 A GB 1111895A
Authority
GB
United Kingdom
Prior art keywords
carboxybenzoylamino
anthraquinone
bis
ester
anilinoanthraquinone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1176066A
Inventor
Albert Charles Cooper
Francis Irving
Alistair Livingston
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1176066A priority Critical patent/GB1111895A/en
Priority to BE683889D priority patent/BE683889A/xx
Priority to DE19661669449 priority patent/DE1669449A1/en
Priority to ES0329200A priority patent/ES329200A1/en
Priority to FR69981A priority patent/FR1487046A/en
Priority to NL6610128A priority patent/NL6610128A/xx
Priority to NL6610127A priority patent/NL6610127A/xx
Publication of GB1111895A publication Critical patent/GB1111895A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/36—Amino acridones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856—Dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/514—N-aryl derivatives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Abstract

Linear polyesters are dyed with a dyestuff of the formula D-(NHCO-X-COOR)n where D represents a polycyclic dyestuff radical containing at least 3 condensed rings and free from sulphonic acid groups, X represents an ethylene or 1:3- or 1:4-phenylene group, R represents H or an alkyl, hydroxyalkyl, dihydroxyalkyl, alkoxyalkyl or hydroxyalkoxyalkyl group. Preferred values of D are 11:91-anthrapyridone, 11:91-anthrapyrimidine, isothiazolanthrone, pyrazolanthrone, 31:41-phthaloylacridone, phthaloylperinone and, particularly, anthraquinone dyestuff radicals. Suitable polyesters contain residues of terephthalic acid and a C2- 10 n-alkylene glycol or dimethylolcyclohexane, of which a part may be replaced by other dicarboxylic or hydroxycarboxylic acid or different glycol residues. The dye may be incorporated by addition to the starting materials or to the partly polymerized reaction mixture, or by mixing in finely divided form or as a dispersion in a volatile liquid, e.g. water or alcohol with the solid polymer (e.g. as chips) then melting and spinning or shaping the mixture. In examples polyethylene terephthalate chips or granules are tumbled with the following dyes in powder form or in suspension in b -ethoxyethanol, then dried if necessary, and melt spun: 1:5-bis(p-carboxybenzoylamino) anthraquinone, 1 - (p-carboxybenzoylamino)anthraquinone, 6 - (p-carboxybenzoylamino) - 31:41 - phthaloylacridone, 1 - (p - carboxybenzoylamino) - 4-anilinoanthraquinone, 1 - (m - carboxybenzoylamino) - 4 - anilinoanthraquinone, 1 - (p-carboxybenzoylamino) - 4 - (21:41:61 - trimethylanilino)anthraquinone, 1 - (m - carboxybenzoylamino) - 5 - amino - 4:8 - dihydroxyanthraquinone, 1 - [p - (b - carboxypropionylamino)anilino] - 4 - hydroxyanthraquinone, 1:5 - bis[41 - (p - carboxybenzoylamino) anilino]-anthraquinone, bis - (b - ethoxyethyl) ester and bis - (b - hydroxyethyl) ester of 1:5 - bis - (p-carboxybenzoylamino)anthraquinone, b :g - dihydroxypropyl ester of 1-(p-carboxybenzoylamino) - 4 - mesidinoanthraquinone, b - hydroxyethyl ester of 1-(p-carboxybenzoylamino)-4 - anilinoanthraquinone, b - (b 1 - hydroxyethoxy) - ethyl ester of 1 - (p - carboxybenzoylamino)anthraquinone and 1-[41-(p-carboxybenzoylamino) - anilino] - 4 - hydroxyanthraquinone. In Example 18 1:5-bis(p-carbomethoxybenzoylamino)anthraquinone is added to the transesterification product of dimethyl terephthalate and ethylene glycol before this is polycondensed.ALSO:Anthraquinone and acridone dyestuffs containing 1 or 2 groups -NHCO-C6H4-COOR or -NHCO-C2H4-COOR, where R represents H or a b -hydroxy-ethyl, b -ethoxy-ethyl, b (b 1 - hydroxyethoxy)ethyl, or b ,g - dihydroxypropyl group, may be prepared by reacting 1:5 - or 1:8 - diaminoanthraquinone, 1-aminoanthraquinone, 6 - amino - 31:41-phthaloylacridone, 1 - amino - 4 - anilinoanthraquinone, 1 - amino - 4 - (21:41:61 - trimethylanilino) anthraquinone, 1:5 - diamino-4:8 - dihydroxyanthraquinone or 1 - hydroxy-4 - (p - aminoanilino) anthraquinone with isophthaloyl chloride, terephthaloyl chloride or succinic anhydride i.p.o. pyridine and hydrolysing the product or treating it with ethylene glycol, ethoxyethanol, diethylene glycol or glycerol.
GB1176066A 1965-07-19 1966-03-17 Process for the mass coloration of polyesters Expired GB1111895A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB1176066A GB1111895A (en) 1966-03-17 1966-03-17 Process for the mass coloration of polyesters
BE683889D BE683889A (en) 1966-03-17 1966-07-08
DE19661669449 DE1669449A1 (en) 1965-07-19 1966-07-13 Bulk dyeing process for synthetic linear polyesters
ES0329200A ES329200A1 (en) 1966-03-17 1966-07-16 Procedure for the coloration of synthetic linear polyesters. (Machine-translation by Google Translate, not legally binding)
FR69981A FR1487046A (en) 1966-03-17 1966-07-19 Synthetic linear polyesters coloring process
NL6610128A NL6610128A (en) 1966-03-17 1966-07-19
NL6610127A NL6610127A (en) 1965-07-19 1966-07-19

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1176066A GB1111895A (en) 1966-03-17 1966-03-17 Process for the mass coloration of polyesters

Publications (1)

Publication Number Publication Date
GB1111895A true GB1111895A (en) 1968-05-01

Family

ID=9992202

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1176066A Expired GB1111895A (en) 1965-07-19 1966-03-17 Process for the mass coloration of polyesters

Country Status (4)

Country Link
BE (1) BE683889A (en)
ES (1) ES329200A1 (en)
GB (1) GB1111895A (en)
NL (1) NL6610128A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049376A (en) * 1975-10-23 1977-09-20 Produits Chimiques Ugine Kuhlmann Dyed copolyesters and method of making
EP1343840A1 (en) * 2000-12-22 2003-09-17 Ciba SC Holding AG Preparation of dyed plastics or polymeric dye particles
CN117659643A (en) * 2023-11-28 2024-03-08 扬州君禾薄膜科技有限公司 Polyester material resistant to wet heat aging and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049376A (en) * 1975-10-23 1977-09-20 Produits Chimiques Ugine Kuhlmann Dyed copolyesters and method of making
EP1343840A1 (en) * 2000-12-22 2003-09-17 Ciba SC Holding AG Preparation of dyed plastics or polymeric dye particles
CN117659643A (en) * 2023-11-28 2024-03-08 扬州君禾薄膜科技有限公司 Polyester material resistant to wet heat aging and preparation method thereof
CN117659643B (en) * 2023-11-28 2024-05-24 扬州君禾薄膜科技有限公司 Polyester material resistant to wet heat aging and preparation method thereof

Also Published As

Publication number Publication date
BE683889A (en) 1967-01-09
ES329200A1 (en) 1967-09-01
NL6610128A (en) 1967-09-18

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