WO2006003088A1 - Colorants disperses pour fibres a base d'acide polylactique - Google Patents

Colorants disperses pour fibres a base d'acide polylactique Download PDF

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Publication number
WO2006003088A1
WO2006003088A1 PCT/EP2005/052835 EP2005052835W WO2006003088A1 WO 2006003088 A1 WO2006003088 A1 WO 2006003088A1 EP 2005052835 W EP2005052835 W EP 2005052835W WO 2006003088 A1 WO2006003088 A1 WO 2006003088A1
Authority
WO
WIPO (PCT)
Prior art keywords
fibers
acid
dyestuffs
dyestuff
use according
Prior art date
Application number
PCT/EP2005/052835
Other languages
English (en)
Inventor
Daisuke Hosada
Koichi Fujisaki
Toshio Hihara
Original Assignee
Dystar Textilfarben Gmbh & Co. Deutschland Kg
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 Dystar Textilfarben Gmbh & Co. Deutschland Kg filed Critical Dystar Textilfarben Gmbh & Co. Deutschland Kg
Priority to CA002571979A priority Critical patent/CA2571979A1/fr
Priority to US11/630,496 priority patent/US20070271710A1/en
Publication of WO2006003088A1 publication Critical patent/WO2006003088A1/fr

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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8276—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester 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
    • 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

Definitions

  • Disperse dyes for polydactic acid based fibers
  • the present invention relates to the use of disperse dyes for dyeing polydactic acid) fibers and polydactic acid) based fibers comprising fiber mixtures of polydactic acid) fibers and other fibers, for example aromatic polyester fibers.
  • Polydactic acid fibers are non-petroleum based fibers for which hydrocarbons of vegetable origin are used as the raw material and which can be recycled in the ecological system by being degraded to water and carbon dioxide in the natural environment. Consequently, they are excellent materials in the environment where there is a shift away from petroleum depletion and the reuse of the resources is facilitated. Furthermore, when compared with other biodegradable materials such as aliphatic polyesters it has a high fusion point and glass transition point and it is also as strong as general-purpose aromatic polyesters and so its widespread future use as practical fibers can be anticipated. Use as an industrial resource material, as an interior and living resource materia!
  • the present invention is based upon an understanding of the actual situation indicated above and is intended to provide disperse dyes with which the color fastness on polydactic acid) based fibers in particular is good and which have a good balance regarding light fastness among the three primary color dyestuffs, which form green and orange and also brown and grey, resembling the extents of fading of the respective dyestuffs.
  • the inventors have realized disperse dyes which meet the above mentioned requirements and which especially have good light fastness and dyeing properties by selecting and specifying from among the many dyestuffs which exist those dyestuffs which have comparatively good light fastness and build-up properties on poly(lactic acid) based fibers and combining these dyestuffs.
  • the present invention thus claims the use of a yellow component comprising at least one dyestuff of the group consisting of structural formulae (1 ), (2), (3), (4) and (5)
  • R 1 is (C 1 -C 3 ) alkyl and R 2 is (C 4 -C 7 ) alkyl;
  • n O or 1 ;
  • R 3 is (C 1 -C 3 ) alkyl or 2-hydroxyethyl
  • a red component comprising at least one dyestuff of the group consisting of structural formulae (6) and (7)
  • R 4 and R 5 are hydrogen and the other is hydroxyethoxyethyl, hydroxybutoxypropyi, acetoxyethoxyethyl or acetoxybutoxypropyl;
  • R e Is hydrogen or methyl; and/or a blue component comprising at least one dyestuff of the group consisting of structural formulae (8), (9) and (10)
  • R 7 and R 8 are nitro and the other hydoxyl and R 9 is hydrogen, chlorine or 2-hydroxyethyl;
  • R 10 is methoxypropyl, ethoxypropyl or methoxyethoxypropyl
  • the present invention thus provides disperse dyes and mixtures of disperse dyes with which dyeing with good light fastness can be carried out on poly(lactic acid) fibers.
  • dyestuffs of the formuiae (1 ) to ⁇ 10 given above (C 1 -C 3 ) alkyl groups can be straight-chain or branched and are preferably methyl, ethyl, n-propyl and iso. propyl.
  • (C 4 -C 7 ) alkyl groups can also be straight-chain or branched and are preferably n- butyl, i-butyl, sek. -butyl, tert. -butyl, pentyl, hexyl or heptyl.
  • R 9 is preferably hydrogen atom or 2-hydroxy- ethyl.
  • the present invention it is preferred to use only one of the dyestuffs of the formulae (1 ) to (10) for dyeing poly(lactic acid) fibers or polydactic acid) based fibers.
  • a mixture comprising a yellow component comprising at least one of the dyestuffs of the formulae (1 ), (3) and (4), a red component comprising at least one dyestuff of the formula (6) and a blue component comprising at least one dyestuff of the formula (8).
  • one ore more dyestuffs of the formulae (1 ) to (10) conjointly with an ultraviolet absorber are known to the skilled person, are described in literature and are available in the market place. Usually such ultraviolet absorbers are triazine- benzotriazole- or benzophenone-based. Examples are the products sold by Ciba Specialty Chemistry, Switzerland, under the tradename Cibafast.
  • the dyestuffs of the formulae (1 ) to (10) are insoluble or sparingly soluble in water and so for dyeing polydactic acid) based fibers using the dyestuff mixtures of this invention a dye bath or printing paste where they have been dispersed in the form of fine particles in an aqueous medium using a naphthalenesulfonic acid/formaldehyde condensate, higher alcohof fatty acid ester, higher alkylbenzenesulfonate or the like as a dispersant is prepared and the dyeing can then be carried out by the dip-dyeing method, the pad-dyeing method or by the dye-printing method.
  • the dip-dyeing method in particular is preferred.
  • polydactic acid fibers or fiber mixtures in which they are included are weak in respect of heat and alkaline conditions when compared with polyester fibers and so high temperature dyeing at from 1 10 to 12O°C for from 15 to 30 minutes with a dye liquid pH of from 4.0 to 5.0 with the conjoint use of triazine-based, benzotriazole-based or benzophenone-based ultraviolet absorber is especially desirable.
  • polydactic acid based fibers is understood to comprise mixtures of polydactic acid ⁇ fibers and other fibers.
  • Such other fibers are preferably aromatic polyester fibers such as polyethylene terephthalate, polypropylene terephthalate or polybutytene terephthalate fibers. Mixtures of propylene terephthalate fibers and polydactic acid ⁇ >,fibers are especially preferred.
  • Examples 1 to 19 The dyestuffs represented by the structural formulae (1-1 ), (1-2), (1-3), (2-1 ), (2-2), (3), (4-1 ), (4-2), (5), (6), (7-1 ), (8-1 ], (8-2), (8-3), (8-4), (9-1 ), (9-2), (9-3) and (10) indicated below were each mixed with twice the weight of naphthalenesulphonic acid/formaldehyde condensate and disperse dyes were obtained by finely grinding and drying in the usual way.
  • Polydactic acid) containing fibers (5 g) produced by the Toray Co., Japan were immersed in the dye bath which had been prepared by weighing out just the amount of disperse dye for about 1 /2N dyed material in the case of a single color and a total concentration of about 1/3N dyed material in the case of a compound color with respect to the standard dye concentration specified in JIS L 0808 for to 5 g of polydactic acid) fibers, adding the triazine based "C ⁇ bafast P" produced by the Ciba Specialty Chemical Co.
  • the light fastness test was carried out using a High Energy Xenon Fadometer produced by the Suga Testing Machine Co. for the testing apparatus under conditions of black panel temperature 73 ⁇ 3°C with irradiation using the 38 cycle (182 hour) illumination method with 3,8 hours illumination time/1 hour dark time per cycle.
  • the tests were carried out with a test cloth lined with urethane.
  • the JIS L 0804 fading gray scale was used for assessing the grade.
  • the dyeing of polydactic acid) based fibers was carried out in the same way as in the examples 1 to 19 using disperse dyes which had been prepared using the yellow dyestuffs (A-1 ) and (A-2), the red dyestuffs (B-1 ) and (B-2) and the blue dyestuffs (C- 1) and (C-2) of which the structural formulae are indicated below which have excellent light fastness on polyester fibers.
  • ⁇ B-1 is a 1 :1 mixture of the two dyestuffs below
  • Dyeing was carried out in accordance with the examples given below using mixtures of disperse dyes as indicated in Table 3, which had been prepared using the dyestuffs of the structural formulae [1 -11, [2-2], [3], [4-1 ], [4-2], [5], [6], [8-1 ], [8-3] r [9-1 ], [9-2] and [10] as described above.
  • the benzotriazole based Sunlife LP250 produced by the Hibana Chemical Co. was used for the ultraviolet absorber.
  • the numerical values indicated as amounts compounded in the table are in units of wt%. m
  • the dyeing of polydactic acid) based fibers was carried out in the same way as in the examples 20 to 31 , but using dyestuffs of examples 20 to 31 and dyestuffs (A-1 ⁇ , (A-2), (B-D, (B-2), (C-D and (C-2) as given in Table 4 below.
  • Dyeing was carried out in accordance with Example 20 except that the fibers used in Example 20 were replaced with a polydactic acid) fiber/poiypropylene terephthalate fiber (50/50wt%) mixture, the dyeing conditions were changed to 12O 0 C x 40 minutes and the ultraviolet absorber was changed to benzophenone based Sunh ' fe LPS855 produced by the Hibana Chemical Co. The results were such that the light fastness of the dyed material obtained was excellent at grade 4.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Artificial Filaments (AREA)

Abstract

La présente invention concerne l'utilisation d'un composé jaune et/ou rouge et/ou bleu de colorants dispersés destinés à la coloration de fibres d'acide polylactique ou de fibres à base d'acide polylactique.
PCT/EP2005/052835 2004-06-25 2005-06-17 Colorants disperses pour fibres a base d'acide polylactique WO2006003088A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002571979A CA2571979A1 (fr) 2004-06-25 2005-06-17 Colorants disperses pour fibres a base d'acide polylactique
US11/630,496 US20070271710A1 (en) 2004-06-25 2005-06-17 Disperse Dyes for Poly(Lactic Acid) Based Fibers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004188921A JP2006008871A (ja) 2004-06-25 2004-06-25 ポリ乳酸系繊維用分散染料
JP2004-188921 2004-06-25

Publications (1)

Publication Number Publication Date
WO2006003088A1 true WO2006003088A1 (fr) 2006-01-12

Family

ID=35033668

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/052835 WO2006003088A1 (fr) 2004-06-25 2005-06-17 Colorants disperses pour fibres a base d'acide polylactique

Country Status (7)

Country Link
US (1) US20070271710A1 (fr)
JP (1) JP2006008871A (fr)
KR (1) KR20070024516A (fr)
CN (1) CN100552130C (fr)
CA (1) CA2571979A1 (fr)
TW (1) TWI363080B (fr)
WO (1) WO2006003088A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109370257A (zh) * 2018-12-14 2019-02-22 苏州市吴江区绿洲染料有限公司 一种耐碱型分散灰染料混合物

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080289156A1 (en) * 2007-05-25 2008-11-27 Mitchell Lewis Zipper construction
JP2011063898A (ja) * 2009-09-16 2011-03-31 Mazda Motor Corp 車両内装部材用表皮材
JP5851417B2 (ja) * 2010-11-19 2016-02-03 日本化薬株式会社 分散染料及びそれを用いる疎水性繊維材料の染色方法
CN103228741B (zh) * 2010-11-30 2015-07-08 日本化药株式会社 分散染料及使用其对疏水性纤维材料进行染色的方法
US8506654B2 (en) 2011-03-29 2013-08-13 Dystar L.P. Disperse dye mixtures which have a high degree of light fastness and build-up
CN102604414B (zh) * 2012-01-16 2013-12-04 杭州吉华江东化工有限公司 一种含苯基吲哚的偶氮化合物及其制备方法与应用
CN102732056B (zh) * 2012-06-01 2013-09-11 浙江吉华集团股份有限公司 一种分散染料混合物及其应用
CN102775812B (zh) * 2012-06-13 2013-12-04 浙江吉华集团股份有限公司 一种分散染料混合物及其应用
CN103073922A (zh) * 2013-01-21 2013-05-01 江苏亚邦染料股份有限公司 一种橙色分散染料组合物
CN111535050A (zh) * 2020-05-28 2020-08-14 张家港扬子染整有限公司 一种pla毛条染色工艺
WO2023104610A1 (fr) 2021-12-07 2023-06-15 Arapaha B.V. Substrat coloré comprenant des fibres d'acide polylactique

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6284004B1 (en) * 1997-12-17 2001-09-04 Ciba Specialty Chemicals Corporation Process for ink-jet printing textile fibre materials
JP2001342375A (ja) * 2000-06-02 2001-12-14 Kiwa Kagaku Kogyo Kk 高耐光性染料組成物及びこれを用いた染色方法
US20020151235A1 (en) * 2000-11-27 2002-10-17 Heike Bartl Dyed and/or printed nonwoven fabric
JP2004168950A (ja) * 2002-11-21 2004-06-17 Dystar Japan Ltd 高耐光堅牢度を有する分散染料混合物
WO2005005552A1 (fr) * 2003-07-04 2005-01-20 Dystar Textilfarben Gmbh & Co. Deutschland Kg Melanges de colorants en dispersion presentant un degre eleve de solidite a la lumiere
JP2005036071A (ja) * 2003-07-18 2005-02-10 Dystar Japan Ltd ポリ乳酸系繊維の染色に適した分散染料混合物

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Publication number Priority date Publication date Assignee Title
US3826609A (en) * 1968-03-14 1974-07-30 Teijin Ltd Method of dyeing synthetic fibers and blends

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6284004B1 (en) * 1997-12-17 2001-09-04 Ciba Specialty Chemicals Corporation Process for ink-jet printing textile fibre materials
JP2001342375A (ja) * 2000-06-02 2001-12-14 Kiwa Kagaku Kogyo Kk 高耐光性染料組成物及びこれを用いた染色方法
US20020151235A1 (en) * 2000-11-27 2002-10-17 Heike Bartl Dyed and/or printed nonwoven fabric
JP2004168950A (ja) * 2002-11-21 2004-06-17 Dystar Japan Ltd 高耐光堅牢度を有する分散染料混合物
WO2005005552A1 (fr) * 2003-07-04 2005-01-20 Dystar Textilfarben Gmbh & Co. Deutschland Kg Melanges de colorants en dispersion presentant un degre eleve de solidite a la lumiere
JP2005036071A (ja) * 2003-07-18 2005-02-10 Dystar Japan Ltd ポリ乳酸系繊維の染色に適した分散染料混合物

Non-Patent Citations (3)

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Title
DATABASE WPI Section Ch Week 200450, Derwent World Patents Index; Class A23, AN 2004-520447, XP002348652 *
DATABASE WPI Section Ch Week 200517, Derwent World Patents Index; Class A23, AN 2005-156280, XP002348651 *
PATENT ABSTRACTS OF JAPAN vol. 2002, no. 04 4 August 2002 (2002-08-04) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109370257A (zh) * 2018-12-14 2019-02-22 苏州市吴江区绿洲染料有限公司 一种耐碱型分散灰染料混合物
CN109370257B (zh) * 2018-12-14 2020-05-19 苏州市吴江区绿洲染料有限公司 一种耐碱型分散灰染料混合物

Also Published As

Publication number Publication date
US20070271710A1 (en) 2007-11-29
CN101040080A (zh) 2007-09-19
JP2006008871A (ja) 2006-01-12
CA2571979A1 (fr) 2006-01-12
KR20070024516A (ko) 2007-03-02
CN100552130C (zh) 2009-10-21
TWI363080B (en) 2012-05-01
TW200606220A (en) 2006-02-16

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