WO2006003088A1 - Colorants disperses pour fibres a base d'acide polylactique - Google Patents
Colorants disperses pour fibres a base d'acide polylactique 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
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
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)
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)
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)
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 |
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/ja active Pending
-
2005
- 2005-06-17 US US11/630,496 patent/US20070271710A1/en not_active Abandoned
- 2005-06-17 WO PCT/EP2005/052835 patent/WO2006003088A1/fr active Application Filing
- 2005-06-17 CN CNB2005800129473A patent/CN100552130C/zh not_active Expired - Fee Related
- 2005-06-17 CA CA002571979A patent/CA2571979A1/fr not_active Abandoned
- 2005-06-17 KR KR1020067021817A patent/KR20070024516A/ko not_active Application Discontinuation
- 2005-06-23 TW TW094121018A patent/TWI363080B/zh 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 (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)
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 (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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2006003088A1 (fr) | Colorants disperses pour fibres a base d'acide polylactique | |
KR20080053952A (ko) | 분산 염료, 분산 염료 조성물, 잉크젯 날염용 잉크, 이들을 이용한 염색 방법 및 염색물 | |
CA2531178C (fr) | Melanges de colorants en dispersion presentant un degre eleve de solidite a la lumiere | |
CN102585553B (zh) | 藏青色活性染料组合物及其在纤维上的染色应用 | |
CN101555360A (zh) | 一种活性三原色染料组合物 | |
TWI544038B (zh) | 纖維反應性染料混合物及其在用於雙或三色染色或印刷方法之用途 | |
CA1101154A (fr) | Traduction non-disponible | |
Sekar | Acid dyes | |
CN112876876B (zh) | 一种分散黄至橙色染料组合物及其染料制品 | |
CN112708287B (zh) | 一种分散黄染料组合物、其制品及应用 | |
CN112574594B (zh) | 一种分散黄至橙色染料组合物及其制品 | |
JP4629676B2 (ja) | 吸着性有機ハロゲン(aox)非含有ネービー色及びブラック色分散染料 | |
KR101865357B1 (ko) | 폴리에스터 섬유 전사날염용 환경친화형 고농도 분산 흑색 염료 조성물 | |
JP5773520B2 (ja) | 分散染料組成物およびそれを用いる疎水性繊維材料の染色法 | |
US5882359A (en) | Vat dye mixtures, processes for their preparation and their use for dyeing cellulosic fibre materials | |
US3821200A (en) | Nitrodiphenylamine dyestuffs | |
CN111484752A (zh) | 染料化合物、染料组合物及其制备方法和应用 | |
JP5917517B2 (ja) | 分散染料組成物およびそれを用いる疎水性繊維材料の染色法 | |
CN115368751B (zh) | 一种高耐晒双偶氮分散染料 | |
CN108795086A (zh) | 一种染料化合物及其染料组合物和应用 | |
JPH05271561A (ja) | モノアゾ染料およびそれを含む混合物 | |
CA2609780A1 (fr) | Colorants plastosolubles bleus grand teint a temperatures elevees | |
CN105733291B (zh) | 一种高移染红色分散染料单体化合物及其制备方法和应用 | |
US3496160A (en) | Monoazo dyestuffs containing a dihalophyridazone group | |
CN115975397A (zh) | 一种染料组合物及其应用和染色方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1020067021817 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 200580012947.3 Country of ref document: CN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2571979 Country of ref document: CA |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWW | Wipo information: withdrawn in national office |
Country of ref document: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11630496 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1020067021817 Country of ref document: KR |
|
122 | Ep: pct application non-entry in european phase | ||
NENP | Non-entry into the national phase |
Ref country code: JP |
|
WWP | Wipo information: published in national office |
Ref document number: 11630496 Country of ref document: US |