WO2006003088A1 - Disperse dyes for poly(lactic acid) based fibers - Google Patents
Disperse dyes for poly(lactic acid) based fibers Download PDFInfo
- 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
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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.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002571979A CA2571979A1 (en) | 2004-06-25 | 2005-06-17 | Disperse dyes for poly(lactic acid) based fibers |
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 |
---|---|---|---|
JP2004-188921 | 2004-06-25 | ||
JP2004188921A JP2006008871A (en) | 2004-06-25 | 2004-06-25 | Disperse dye for polylactic acid fiber |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006003088A1 true WO2006003088A1 (en) | 2006-01-12 |
Family
ID=35033668
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/052835 WO2006003088A1 (en) | 2004-06-25 | 2005-06-17 | Disperse dyes for poly(lactic acid) based fibers |
Country Status (7)
Country | Link |
---|---|
US (1) | US20070271710A1 (en) |
JP (1) | JP2006008871A (en) |
KR (1) | KR20070024516A (en) |
CN (1) | CN100552130C (en) |
CA (1) | CA2571979A1 (en) |
TW (1) | TWI363080B (en) |
WO (1) | WO2006003088A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109370257A (en) * | 2018-12-14 | 2019-02-22 | 苏州市吴江区绿洲染料有限公司 | A kind of alkali resistant dispersion gray dye mixture |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080289156A1 (en) * | 2007-05-25 | 2008-11-27 | Mitchell Lewis | Zipper construction |
JP2011063898A (en) * | 2009-09-16 | 2011-03-31 | Mazda Motor Corp | Skin material for vehicle interior member |
WO2012067027A1 (en) * | 2010-11-19 | 2012-05-24 | 日本化薬株式会社 | Disperse dye and method for dyeing hydrophobic fiber material using same |
CN103228741B (en) * | 2010-11-30 | 2015-07-08 | 日本化药株式会社 | Disperse dyes and method for dyeing hydrophobic fiber material using same |
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 (en) * | 2012-01-16 | 2013-12-04 | 杭州吉华江东化工有限公司 | Azo compound containing phenylindole, preparation method and application thereof |
CN102732056B (en) * | 2012-06-01 | 2013-09-11 | 浙江吉华集团股份有限公司 | Disperse dye mixture and application thereof |
CN102775812B (en) * | 2012-06-13 | 2013-12-04 | 浙江吉华集团股份有限公司 | Disperse dye mixture and application thereof |
CN103073922A (en) * | 2013-01-21 | 2013-05-01 | 江苏亚邦染料股份有限公司 | Orange disperse dye composition |
CN111535050A (en) * | 2020-05-28 | 2020-08-14 | 张家港扬子染整有限公司 | PLA wool top dyeing process |
WO2023104610A1 (en) | 2021-12-07 | 2023-06-15 | Arapaha B.V. | Dyed substrate comprising poly(lactic acid) fibres |
Citations (6)
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 (en) * | 2000-06-02 | 2001-12-14 | Kiwa Kagaku Kogyo Kk | Highly light resistant dye composition and dying method using the same |
US20020151235A1 (en) * | 2000-11-27 | 2002-10-17 | Heike Bartl | Dyed and/or printed nonwoven fabric |
JP2004168950A (en) * | 2002-11-21 | 2004-06-17 | Dystar Japan Ltd | Disperse dye mixture having high color fastness to light |
WO2005005552A1 (en) * | 2003-07-04 | 2005-01-20 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Disperse dye mixtures which have a high degree of light fastness |
JP2005036071A (en) * | 2003-07-18 | 2005-02-10 | Dystar Japan Ltd | Disperse dye mixture suitable for dyeing polylactic acid fiber |
Family Cites Families (1)
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 |
-
2004
- 2004-06-25 JP JP2004188921A patent/JP2006008871A/en active Pending
-
2005
- 2005-06-17 CN CNB2005800129473A patent/CN100552130C/en not_active Expired - Fee Related
- 2005-06-17 WO PCT/EP2005/052835 patent/WO2006003088A1/en active Application Filing
- 2005-06-17 CA CA002571979A patent/CA2571979A1/en not_active Abandoned
- 2005-06-17 US US11/630,496 patent/US20070271710A1/en not_active Abandoned
- 2005-06-17 KR KR1020067021817A patent/KR20070024516A/en not_active Application Discontinuation
- 2005-06-23 TW TW094121018A patent/TWI363080B/en not_active IP Right Cessation
Patent Citations (6)
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 (en) * | 2000-06-02 | 2001-12-14 | Kiwa Kagaku Kogyo Kk | Highly light resistant dye composition and dying method using the same |
US20020151235A1 (en) * | 2000-11-27 | 2002-10-17 | Heike Bartl | Dyed and/or printed nonwoven fabric |
JP2004168950A (en) * | 2002-11-21 | 2004-06-17 | Dystar Japan Ltd | Disperse dye mixture having high color fastness to light |
WO2005005552A1 (en) * | 2003-07-04 | 2005-01-20 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Disperse dye mixtures which have a high degree of light fastness |
JP2005036071A (en) * | 2003-07-18 | 2005-02-10 | Dystar Japan Ltd | Disperse dye mixture suitable for dyeing polylactic acid fiber |
Non-Patent Citations (3)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109370257A (en) * | 2018-12-14 | 2019-02-22 | 苏州市吴江区绿洲染料有限公司 | A kind of alkali resistant dispersion gray dye mixture |
CN109370257B (en) * | 2018-12-14 | 2020-05-19 | 苏州市吴江区绿洲染料有限公司 | Alkali-resistant disperse grey dye mixture |
Also Published As
Publication number | Publication date |
---|---|
JP2006008871A (en) | 2006-01-12 |
CN100552130C (en) | 2009-10-21 |
TWI363080B (en) | 2012-05-01 |
CA2571979A1 (en) | 2006-01-12 |
CN101040080A (en) | 2007-09-19 |
KR20070024516A (en) | 2007-03-02 |
US20070271710A1 (en) | 2007-11-29 |
TW200606220A (en) | 2006-02-16 |
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