EP2699727A1 - Procédé de teinture du polyester - Google Patents

Procédé de teinture du polyester

Info

Publication number
EP2699727A1
EP2699727A1 EP12707755.0A EP12707755A EP2699727A1 EP 2699727 A1 EP2699727 A1 EP 2699727A1 EP 12707755 A EP12707755 A EP 12707755A EP 2699727 A1 EP2699727 A1 EP 2699727A1
Authority
EP
European Patent Office
Prior art keywords
textile material
hydrogen
liquor
alkyl
treated
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.)
Granted
Application number
EP12707755.0A
Other languages
German (de)
English (en)
Other versions
EP2699727B1 (fr
Inventor
Peter Scheibli
Gilles SPERISSEN
Marisa BIANCO
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.)
Huntsman Advanced Materials Switzerland GmbH
Original Assignee
Huntsman Advanced Materials Switzerland GmbH
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 Huntsman Advanced Materials Switzerland GmbH filed Critical Huntsman Advanced Materials Switzerland GmbH
Priority to EP12707755.0A priority Critical patent/EP2699727B1/fr
Publication of EP2699727A1 publication Critical patent/EP2699727A1/fr
Application granted granted Critical
Publication of EP2699727B1 publication Critical patent/EP2699727B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters

Definitions

  • Gi and G 2 independently of one another, are C C 4 alkyl or together are pentamethylene, Zi and Z 2 are methyl, ⁇ ⁇ ⁇ and Z 2 together form a bridging member which is
  • E is oxyl or hydroxyl.
  • any disperse dye known for dyeing polyester can be used in the process according to the invention.
  • R 2 is hydrogen, bromo, chloro, cyano or nitro
  • R 4 is hydrogen, methyl or methoxy
  • R 5 and R 6 independently of one another, are ethyl, benzyl, 2-cyanoethyl, 2-hydroxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-(2-methoxyethoxy)-ethyl, 2-(2-ethoxyethoxy)-ethyl, 2-acetyloxyethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-methoxycarbonylethyl or 1-ethoxycarbonylethyl,
  • R 7 is hydrogen, bromo, chloro, cyano or nitro
  • R 8 is bromo, chloro, cyano or nitro
  • Rio is hydrogen, methyl, methoxy, acetylamino or propionylamino.
  • the disperse dyes of formulae (2), (3) and (4) are known or can be prepared according to known methods.
  • the following disperse dyes are preferFred: C.I. Disperse Yellow 114, C.I. Disperse Yellow 211 , C.I. Disperse Yellow 54, C.I. Disperse Orange 25, C.I. Disperse Orange 30,
  • C.I. Disperse Orange 31 C.I. Disperse Orange 44, C.I. Disperse Orange 61 , C.I. Disperse Red 50, C.I. Disperse Red 73, C.I. Disperse Red 82, C.I. Disperse Red 167, Disperse Red 167: 1 , C.I. Disperse Red 324, C.I. Disperse Red 356, C.I. Disperse Red 376, C.I. Disperse Red 382, C.I. Disperse Red 383, C.I. Disperse Violet 93:1 , C.I. Disperse Violet 107, C.I. Disperse Blue 56, C.I. Disperse Blue 60, C.I.
  • the component (b) to be used in the method according to the invention also includes the ammonium salts obtainable by reaction of the compound of formula (1) with acids.
  • Rii is hydrogen or methyl
  • n 1 or 2
  • Y is hydrogen, CrCi 8 alkyl, C 2 -Ci 0 alkenyl, propargyl, glycidyl or C 2 -C 50 alkyl which is unsubstituted or substituted by 1 - 10 hydroxyl groups and which may be interrupted by 1 - 20 oxygen atoms, or
  • Y is CrCi 2 alkylene, C 4 -Ci 2 alkenylene, xylylene or CrC 50 alkylene, which is
  • Suitable compounds of the formula (1a) are, for example,
  • the textile material is treated with a liquor containing as component (b) 1-oxyl- 2,2,6,6-tetramethyl-4-hydroxypiperidine of the formula
  • the dyes according to component (a) can be applied individually or in mixtures.
  • mixtures of two or three dyes may be used.
  • Mixtures of four or more dyes can also be used, especially in the production of combination shades.
  • the amounts in which the individual dyes are used in the dye liquors can vary within wide limits depending on the desired depth of shade. In general, amounts of from 0.01 to 35 % by weight, especially from 0.1 to 15 % by weight, based on the fibre material to be dyed have proved to be advantageous.
  • the liquor ratio can be selected from within a wide range, for example within a range of from 1 :2 to 1 :50, preferably from 1 :3 to 1 :15.
  • the liquor can comprise, in addition to components (a) and (b) as defined above, further customary additives, such as dispersing, levelling and wetting agents, penetration
  • Suitable dispersing agents can be nonionic or anionic.
  • Nonionic dispersing agents are, for example, reaction products of alkylene oxides, like ethylene oxide or propylene oxide, with fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersing agents are, for example, lignin sulfonates and salts thereof, alkyl- or alkylaryl-sulfonates, alkylaryl polyglycol ether sulfates, alkali metal salts of the condensation products of naphthalenesulfonic acids and formaldehyde, polyvinyl sulfonates and ethoxylated novolaks.
  • the textile material can be used in any form, e.g. in the form of fibres, yarn, woven fabric, knitted fabric or non-woven.
  • Polyester-containing textile material in terms of the invention includes pure polyester as well as blends containing polyester and further synthetic, semi-synthetic or natural textile material, like polyester/cotton, polyester/wool or polyester/elastan blends.
  • the textile material is polyester or a polyester/cotton blend.
  • polyester fibre materials are dyed from an aqueous dispersion by the exhaust process in the presence of customary anionic or nonionic dispersants and in the presence or absence of customary swelling agents (carriers) at pH 3.5 - 5.5, in particular at pH 4.0 - 5.0, in the temperature range from 80 to 150 °C, preferably from 90 to 140 °C.
  • Special apparatus is not required.
  • customary dyeing apparatus e.g. open baths, winch becks, jigs, or paddle, jet or circulation apparatus, may be used.
  • an aftertreatment can be carried out at a pH value of e.g. from 7 to 12, especially from 7 to 9, and a temperature of e.g. from 30 to 100 °C, especially from 50 to 80 °C, to remove any unfixed dye.
  • unfixed dye can advantageously be removed reductively, by adding to the alkaline aftertreatment bath a reducing agent, for example a hydrosulfite, e.g. sodium hydrosulfite.
  • Dye that has been fixed in the fibre material is not attacked by the treatment.
  • the amount of reducing agent added is e.g. from 0.1 to 8.0 % by weight, especially from 0.5 to 5.0 % by weight, based on the weight of the aftertreatment bath.
  • 10 g knitted 100% polyester fabric is dyed in an autoclave by preparing a dye liquor of 100 ml total volume containing 45 mg of a commercial formulation of C.I. Disperse Blue 165: 1 , 50 mg of a compound of formula (101), 200 mg of a commercial dispersing agent (REAX 85A, lignin sulfonate, supplied by BASF), 50 mg of a commercial wetting and defoaming agent (ALBAFLOW ® UNI, supplied by Huntsman), 100 mg ammonium sulfate and about 0.1 ml of acetic acid 80% to get pH of 4.5.
  • a commercial dispersing agent RX 85A, lignin sulfonate, supplied by BASF
  • ABAFLOW ® UNI commercial wetting and defoaming agent
  • the fabric is put into the dye liquor and just before closing the autoclave it is thoroughly washed with nitrogen to simulate a fully flooded bulk dyeing machine, where all the air and the oxygen with it is removed completely.
  • the liquor is heated up with 2 °C per minute to 135 °C and is kept at 135 °C for 60 minutes.
  • the dyeing is treated in a reductive clearing: 20 min/70 °C in a liquor containing 5 ml/l caustic soda 36°Be, 2 g/l sodium hydrosulfite cone, and 1 g/l of a commercial nonionic washing agent (ERIOPON ® OL, supplied by Huntsman).
  • the dyeing is rinsed, neutralized and dried.
  • the depth of shade is determined by reflectance measurement and expressed in percentage in relation to the depth of shade which is obtained by a benchmark process carried out with same fabric, dye and auxiliaries but using UNIVADINE ® DP (dispersing agent, supplied by Huntsman) instead of the compound of formula (101), which is set as 100%.
  • UNIVADINE ® DP disersing agent, supplied by Huntsman
  • Example 1 and Comparative Example 2 are repeated with other dyes.
  • the resulting depth of shade values are summarized in Table 1.
  • Comparative Example 2 and Example 1 is made with a fabric blend of 65% cotton and 35% polyester instead of the 100% polyester fabric and without the 200 mg of commercial lignin sulfonate dispersing agent (REAX 85A) and without the washing with nitrogen.
  • the resulting depth of shade values are summarized in Table 3.
  • 5 g knitted 100% polyester fabric is dyed in an autoclave with a dye liquor of 50 ml total volume containing 75 mg of a commercial formulation of C.I. Disperse Red 277 (Solvent Red 197), 20 mg of a compound of formula (101), 100 mg of a commercial wetting and defoaming agent (ALBAFLOW ® UNI, supplied by Huntsman), 50 mg ammonium sulfate and about 0.05 ml of acetic acid 80% to get pH of 4.5.
  • the liquor is heated up with 2 °C per minute to 135 °C and is kept at 135 °C for 60 minutes.
  • Example 3 and 4 are repeated by replacing 75 mg Disperse Red 277 with 75 mg Disperse Red 362 (Solvent Red 196) providing the same positive effect on shade and fluorescence in the case of Example 5 (use of the compound of formula (101)) compared to Example 6.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne un procédé de teinture d'un matériau textile contenant du polyester, caractérisé en ce que le matériau textile est traité au moyen d'une liqueur contenant (a) au moins une teinture dispersée et (b) au moins un composé de formule (1), dans laquelle G1 et G2 sont, indépendamment l'un de l'autre, un alkyle en C1 à C4 ou, ensemble, un pentaméthylène, Z1 et Z2 sont un méthyle, ou Z1 et Z2 forment ensemble un chaînon de pontage qui est non substitué ou substitué par un radical ester, éther, hydroxyle, oxo, cyanohydrine, amido, amino, carboxyle ou uréthane, et E est un oxyle ou un hydroxyle.
EP12707755.0A 2011-04-20 2012-03-07 Procédé de teinture du polyester Active EP2699727B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12707755.0A EP2699727B1 (fr) 2011-04-20 2012-03-07 Procédé de teinture du polyester

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11163130 2011-04-20
EP12707755.0A EP2699727B1 (fr) 2011-04-20 2012-03-07 Procédé de teinture du polyester
PCT/EP2012/053882 WO2012143167A1 (fr) 2011-04-20 2012-03-07 Procédé de teinture du polyester

Publications (2)

Publication Number Publication Date
EP2699727A1 true EP2699727A1 (fr) 2014-02-26
EP2699727B1 EP2699727B1 (fr) 2014-11-19

Family

ID=44544002

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12707755.0A Active EP2699727B1 (fr) 2011-04-20 2012-03-07 Procédé de teinture du polyester

Country Status (9)

Country Link
US (1) US20140041134A1 (fr)
EP (1) EP2699727B1 (fr)
JP (1) JP5913566B2 (fr)
KR (1) KR101902752B1 (fr)
CN (1) CN103502528B (fr)
BR (1) BR112013026857B8 (fr)
ES (1) ES2528911T3 (fr)
TW (1) TWI540236B (fr)
WO (1) WO2012143167A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2943652T3 (es) * 2017-06-28 2023-06-15 Huntsman Textile Effects Switzerland Gmbh Colorantes azo dispersados
CN114437564B (zh) * 2022-02-28 2024-04-02 浙江万丰化工股份有限公司 一种高牢度分散染料组合物及其应用
CN116082857A (zh) * 2022-12-27 2023-05-09 浙江闰土股份有限公司 蓝色分散染料组合物、蓝色分散染料及其制备方法和用途
CN115850997B (zh) * 2022-12-27 2024-04-12 浙江闰土股份有限公司 蓝色分散染料组合物、蓝色分散染料及其制备方法和用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE788960A (fr) * 1971-09-18 1973-03-19 Hoechst Ag Procede de realisation de teintures et impressions solides a lalumiere sur des fibres synthetiques
JPS5423783A (en) * 1977-07-15 1979-02-22 Sanyo Chemical Ind Ltd High temperature dyeing of polyester fiber
JPS5936035B2 (ja) * 1980-05-13 1984-08-31 住友化学工業株式会社 疎水性繊維材料の染色方法
JPS60252785A (ja) * 1984-05-29 1985-12-13 共同薬品株式会社 光堅牢度の優れたポリエステル系染色糸又は染色織布
EP0409771A3 (en) * 1989-06-27 1991-06-12 Ciba-Geigy Ag Process of photochemical and thermal stabilization of polyamide fibres, dyeable by acid and basic dyes, and of their mixtures amongst themselves and with other fibres
KR100849438B1 (ko) 2000-05-11 2008-07-31 시바 홀딩 인크 수성 목재 착료를 사용하는 목재의 착색방법
ATE329973T1 (de) * 2001-01-16 2006-07-15 Ciba Sc Holding Ag Tintenstrahldrucktinte und -aufzeichnungsmaterial
ES2342594T3 (es) * 2002-05-02 2010-07-09 Basf Se Productos estabilizados para el cuidado personal y productos para el hogar.
EP1680541B1 (fr) * 2003-11-03 2012-12-19 Basf Se Produits pour soins corporels, produits menagers, textiles et tissus stabilises
JP2009526921A (ja) * 2006-02-17 2009-07-23 ハンツマン アドバンスト マテリアルズ （スイッツァランド） ゲーエムベーハー ポリエステルを染色するための方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2012143167A1 *

Also Published As

Publication number Publication date
ES2528911T3 (es) 2015-02-13
KR20140025476A (ko) 2014-03-04
KR101902752B1 (ko) 2018-10-02
US20140041134A1 (en) 2014-02-13
CN103502528A (zh) 2014-01-08
BR112013026857B8 (pt) 2023-05-16
TW201303112A (zh) 2013-01-16
TWI540236B (zh) 2016-07-01
WO2012143167A1 (fr) 2012-10-26
BR112013026857B1 (pt) 2020-09-29
CN103502528B (zh) 2017-10-20
EP2699727B1 (fr) 2014-11-19
JP2014516390A (ja) 2014-07-10
JP5913566B2 (ja) 2016-04-27

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