EP0055694A2 - Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester - Google Patents

Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester Download PDF

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Publication number
EP0055694A2
EP0055694A2 EP81810513A EP81810513A EP0055694A2 EP 0055694 A2 EP0055694 A2 EP 0055694A2 EP 81810513 A EP81810513 A EP 81810513A EP 81810513 A EP81810513 A EP 81810513A EP 0055694 A2 EP0055694 A2 EP 0055694A2
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EP
European Patent Office
Prior art keywords
group
alkyl
hydrogen
formula
compounds
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
EP81810513A
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German (de)
English (en)
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EP0055694B1 (fr
EP0055694A3 (en
Inventor
Zdenek Koci
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0055694A2 publication Critical patent/EP0055694A2/fr
Publication of EP0055694A3 publication Critical patent/EP0055694A3/de
Application granted granted Critical
Publication of EP0055694B1 publication Critical patent/EP0055694B1/fr
Expired legal-status Critical Current

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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
    • 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
    • D06P1/22—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 vat dyestuffs including indigo
    • D06P1/221—Reducing systems; Reducing catalysts
    • 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
    • D06P1/30—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 sulfur dyes

Definitions

  • the invention relates to specific vatting accelerators, which are added to a vat or sulfur dye preparation or a dye bath or a printing paste containing such dyes, to improve the color yield on materials treated with it, especially cellulose-containing materials.
  • the object of the invention was therefore to find vatting accelerators which do not have the disadvantages mentioned above and which increase the rate of reduction of the dyes in the fast-working dyeing and printing processes with vat and sulfur dyes and at the same time increase the color yield of the dyeings from the dye liquor or Improve printing paste.
  • vatting accelerators or mixtures thereof are used as described below.
  • These specific vatting accelerators are known per se as antioxidants, have an excellent effectiveness, are inexpensive and do not have the disadvantages mentioned at the outset. They can either be present in a vat or sulfur dye preparation, or can be added to the dye bath or reduction bath or the printing paste.
  • R 1 , R 2 and R 3 in the meaning of a C 1 -C 12 alkyl group can be unbranched or branched. It is for example the methyl group, ethyl group, n-propyl group, iso-propyl group, the n-, sec- or tert-butyl group, the n-, sec- or tert-amyl group, the n-, sec. - or tert-hexyl group, the n-, sec- or tert-octyl group or the n-, sec- or tert-dodecyl group.
  • R 1 , R 2 and R 3 represent, for example, the methoxy, ethoxy, n- or iso-propoxy and n- or iso-butoxy group.
  • benzyl radical or phenethyl for example: halogen, such as Fl, Cl or Br, the OH group, C 1 -C 12 alkyl, preferably C 1 -C 4 alkyl (branched or unbranched) or C 1 -C 4 alkoxy (branched or unbranched).
  • the type (A) compounds mentioned are known and can be prepared by known methods.
  • a further class of compounds are the compounds of class (A) which are linked to an organic radical via a bridge member R 'instead of the substituent R 3 .
  • These are compounds of the formula organic radical, in which R and R 2 have the meaning given above, m is a number 1 or 2 and R ' 3 is any bridging element, for example the radical of an inorganic or organic acid or the radical of an aldehyde, a styrene or an olefin and preferably one Group represents wherein R 4 is independently hydrogen or C 1 -C 4 alkyl.
  • R 1 , R 2 and R ' 3 have the meanings given above and X is an aliphatic bridge member, preferably - (CH 2 ) 2 -COO-CH 2 , m is a number 1 or 2 and n is a number 1 to 4 and p is a Number 1 to 3 mean.
  • This group includes the partial or full esters of compounds of type (A) with inorganic and organic acids, such as with phosphorous acid, corresponding mono-, di- or trisphosphites, or with isocyanuric acid.
  • compounds of this type are, for example the tris (3, 5 - di-tert-butyl-4-hydroxyphenyl) phosphite.
  • Group B furthermore also includes those compounds which are formed by condensation of compounds of type A with, for example, aldehydes, such as formaldehyde or crotonaldehyde, or also reaction products of compounds (A) with e.g. Styrene and its derivatives or with olefins.
  • aldehydes such as formaldehyde or crotonaldehyde
  • reaction products of compounds (A) with e.g. Styrene and its derivatives or with olefins e.g. Styrene and its derivatives or with olefins.
  • Examples of further compounds of this type are: 2,2'-methylene-bis (4-methyl-6-tert-butyl-phenol), 2,2'-thio-bis (4-methyl-6-tert.- butyl-phenol), thio-bis (di-sec.-amyl-phenol), and especially 4,4'-methylene-bis (2,6-di-tert-butyl-phenol), and preferably tetrakis [methylene -3- (3 ', 5'-di-tert-butyl-4'-hydroxyphenyl) propio nat] methane of the formula
  • R 4 is a C 1 -C 4 alkyl group, it is, for example, the methyl, ethyl, n or isopropyl group or the n, sec or tert-butyl group.
  • R 5 and / or R 6 are a C 1 -C 12 alkyl group, it is, for example, an unbranched or branched alkyl group, such as the methyl, ethyl, n- or iso-propyl, n-, sec.- or tert-butyl, n- or iso-hexyl, n- or iso-octyl or around the n- or iso-dodecyl group.
  • R 5 and / or R 6 represents a C 3 -C 12 alkenyl group
  • the allyl is, for example called group.
  • R 5 and / or R 6 are halogen, it is fluorine, chlorine or bromine.
  • R and / or R 6 are a C 1 -C 4 alkoxy group, it is, for example, the methoxy, ethoxy, n or iso-propoxy and n or iso-butoxy group.
  • R 5 and / or R 6 is a substituted phenyl, the following may be used as substituents: halogen, such as fluorine, chlorine or bromine, the OH group, a C 1 -C 4 alkoxy group (branched or unbranched ) and a C 1 -C 12 alkyl group (branched or unbranched).
  • halogen such as fluorine, chlorine or bromine
  • the OH group a C 1 -C 4 alkoxy group (branched or unbranched ) and a C 1 -C 12 alkyl group (branched or unbranched).
  • Preferred from these classes of compounds (A) and (B) are those compounds which contain a sterically hindered phenol group, in particular those where the o position to the OH group is occupied by a tertiary alkyl radical.
  • R 11 denotes a C 1 -C 4 alkyl group or a C 1 -C 3 alkoxy group, this can be unbranched or branched.
  • R 12 is a C 1 -C 12 alkyl group, this can be unbranched or branched; Examples include the methyl, ethyl, n or iso-hexyl and n or iso-octyl group.
  • suitable substituents for phenyl are: halogen, such as fluorine, chlorine or bromine, the NH 2 group and the OH group.
  • R 16 represents an unbranched or branched C 1 -C 4 alkyl group, such as the methyl, ethyl, n or iso-propyl or n, sec or tert-butyl group. These compounds are known and can be prepared by known methods. A preferred compound from this class is 4-hydroxy-acetophenone.
  • thioamides these are known thioamides, the most interesting representatives in this context being thioacetamide, N, N'-dimethylthiourea and, above all, thiourea.
  • R 23 , R 24 ' R 25' R 26 and R 27 OH, halogen (F, Cl, Br), NH 2 and C 1 -C 4 alkyl.
  • K compounds of the formula wherein R 30 represents an unbranched or branched C 1 -C 12 alkyl group, such as the methyl, ethyl, n or iso-propyl, n or iso-hexyl or n or iso-octyl group.
  • gallic acid esters these are the known gallic acid esters, the most interesting representatives of which are n-propyl gallate and n-octyl gallate.
  • L compounds of the formula wherein R 31 is hydrogen, CH 2 OH or the C 1 -C 2 alkyl group.
  • R 31 is hydrogen, CH 2 OH or the C 1 -C 2 alkyl group.
  • examples of this class include propylene glycol sulfite.
  • All of the compounds mentioned under A) to L) are characterized by easy synthetic accessibility and good distributability in the dye preparations, dye baths and printing pastes.
  • the compounds mentioned should be water-soluble and / or soluble in an alkaline reductive bath (pH ⁇ 12). If they do not meet these solubility requirements, it is advisable to grind these compounds prior to their use, for example with an anionic dispersant, to a particle size of ⁇ 5 ⁇ , in particular about 1 / u.
  • vatting accelerator or a mixture thereof is mixed with a dispersant, for example a naphthalenesulfonic acid / formaldehyde condensation product, for example by wet grinding together in a corundum disk mill, ball mill, agitator mill, sand mill or other grinding units, optionally with a subsequent one Drying the mixture, for example in an atomizing dryer.
  • a dispersant for example a naphthalenesulfonic acid / formaldehyde condensation product
  • vatting accelerators mentioned are used in the dye preparations in amounts of 0.1 to 20 percent by weight, especially between 0.5 and 10 percent by weight, based on the dye.
  • Preferred compounds are compounds according to groups D, F to H, K and L and in particular phenols and amines according to groups A, B, C and I.
  • the dye preparations contain anionic dispersants or possibly nonionic ones Fillers, preferably in amounts of 0.5 to 80 percent by weight. Such dispersants are primarily used as described in DE-OS 28 16 539.
  • vat and sulfur dyes examples include: indanthrones, flavanthrones, pyranthrones, violanthrones, isoviolanthrones, benzanthrones, imides of perylene tetracarboxylic acid substituted on nitrogen, acridones, anthraquinone oxazoles, anthraquinone thiazoles and compounds which are derived primarily from anthraquinone.
  • Further additives which may be present in the dyeing preparations are those customary in dyeing preparations, such as humectants, antifoams, preservatives, wetting agents, leveling agents, thickeners, etc.
  • the vocation accelerators A to L or mixtures thereof mentioned can also be added directly to the dyebath, chemical bath or pressure batch.
  • the mentioned accelerator is used in quantities of 0.01 - 5 g / ltr.
  • the preferred quantity range is between 0.05 and 1 g / ltr.
  • the dyebaths and printing pastes also contain reducing agents, especially sodium dithionite, sodium formaldehyde sulfoxylate or thiourea dioxide, and the alkaline media range is adjusted primarily with NaOH or KOH.
  • Suitable dyeing and printing processes in which an improvement in the color yield of about 7% to 10% or more is achieved by the addition of the vatting accelerators according to the invention, are the usual for dyeing and printing with vat and sulfur dyes, especially for cotton, and cotton / polyester blends.
  • These linking accelerators can be used both in the pull-out process and in the printing process and in particular in the continuous process.
  • the addition of vatting accelerators means that less dye has to be used, which in turn is an economic factor.
  • a dyeing process e.g. called: pull-out process in the jigger, in the reel runner and in the jet dyeing machine, the pad-jig process, the standfast process, the semi-pigmentation process, the block fixing process, e.g. the one-bath block steam process, the pad roll process, the pad roll process with intermediate drying, the wet steam process and above all the pad steam process.
  • printing processes e.g. called: single-phase and two-phase development processes.
  • the cotton fabric is then steamed at 100 ° for 30 seconds in the steamer. Then rinsed as usual, with 3 ml / l H 2 0 2 30%, oxidized for 15 minutes at 50 °, rinsed and 15 minutes at the cooking temperature with 2 g / 1 of an anionic detergent and 1 g / 1 soda calc. soaped. A blue coloration is obtained which is more intense in color than a comparison coloration without the addition of 30% aqueous dispersion of tetrakis [methylene-3- (3 ', 5'-di-tert-butyl-4'-hydroxyphenyl) propionate ]-methane.
  • Example 2 Pre-cleaned cotton fabric is contained in the pad-steam process with a dyeing liquor
  • Example 3 A printing paste of the following composition: ..
  • Washed-out cotton fabric is padded with this dye liquor and treated as in Example 4 until the dyeing is finished.
  • Example 6 Cleaned cotton fabric is pad-steamed with a dyeing liquor containing 50 parts of the liquid commercial form of the dye Vat Blue 6 (Color Index No. 69825) and 950 parts of water
  • the fabric After steaming at 100 ° for approx. 30 seconds, the fabric is treated in the same way as in Example 1.
  • the fabric After steaming at 100 ° for about 30 seconds, the fabric is treated in the same way as in Example 1.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
EP81810513A 1980-12-30 1981-12-22 Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester Expired EP0055694B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH9644/80 1980-12-30
CH964480 1980-12-30

Publications (3)

Publication Number Publication Date
EP0055694A2 true EP0055694A2 (fr) 1982-07-07
EP0055694A3 EP0055694A3 (en) 1983-01-19
EP0055694B1 EP0055694B1 (fr) 1986-06-04

Family

ID=4354139

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81810513A Expired EP0055694B1 (fr) 1980-12-30 1981-12-22 Procédé de teinture et d'impression de matières à base de cellulose et de tissus à base de mélanges cellulose/polyester

Country Status (5)

Country Link
US (2) US4519805A (fr)
EP (1) EP0055694B1 (fr)
JP (2) JPS57133281A (fr)
DE (1) DE3174788D1 (fr)
ZA (1) ZA818967B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0310556A1 (fr) * 1987-10-01 1989-04-05 Ciba-Geigy Ag Procédé de teinture de fibres cellulosiques ayant une égalité de nuance entre les extrémités du tissu
EP0719621A1 (fr) * 1994-12-28 1996-07-03 ALPI S.p.A. Peinture des feuilles du bois avec des colorants appartenant aux colorants de cuve

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3704125A1 (de) * 1987-02-11 1988-08-25 Basf Ag Verwendung von cyclischen estern der schwefligen saeure beim faerben von textilmaterialien aus polyamid und verfahren zum faerben
JPS63271963A (ja) * 1987-04-28 1988-11-09 Nec Corp 半導体装置の製造方法
KR900012875A (ko) * 1989-02-08 1990-09-03 오스카 아끼히꼬 비페닐 유도체, 신경세포 변성수복 또는 보호제 및 여기에 사용되는 폐닐유도체의 제조방법
US5108505A (en) * 1990-05-16 1992-04-28 Hewlett-Packard Company Waterfast inks via cyclodextrin inclusion complex
US5961670A (en) * 1995-05-03 1999-10-05 Clariant Finance (Bvi) Limited Sulfur dyes
TR200003566T2 (tr) 1998-06-23 2001-06-21 Henkel Kommanditgesellschaft Auf Aktien Keratin dokuların boyanması için boyalar
CN104372685A (zh) * 2014-12-05 2015-02-25 江苏太子鳄服饰有限公司 布料的耐洗印染方法

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DE1163284B (de) * 1960-10-15 1964-02-20 Hoechst Ag Verwendung von Methylendiarylverbindungen als Dispergiermittel fuer in Wasser unloesliche oder schwer loesliche Farbstoffe
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CH429375A4 (fr) * 1975-04-04 1977-06-15
DE2525021A1 (de) * 1975-06-05 1976-12-23 Hoechst Ag Verfahren und mittel zur herstellung von direktdrucken und buntaetzen mit kuepen- oder schwefelfarbstoffen
DE2628903A1 (de) * 1976-06-28 1978-01-05 Boc Ltd Dithionit-stabilisator-zubereitung, verfahren zu ihrer herstellung und verwendung des stabilisators in der zubereitung
DE2657774C2 (de) * 1976-12-21 1982-06-16 Hoechst Ag, 6000 Frankfurt Verwendung eines wasserlöslichen nicht-ionogenen Polyglykoläthers als Mahlhilfsmittel und wäßrige Zubereitungen von in Wasser schwer- bis unlöslichen Farbstoffen
DE2901461A1 (de) * 1979-01-16 1980-07-24 Hoechst Ag Verwendung oxalkylierter novolakharze als praeparationsmittel fuer dispersionsfarbstoffe und damit hergestellte zubereitungen
GB2114166B (en) * 1982-02-03 1985-08-14 Sandoz Ltd Level dyeing of polyester materials

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0310556A1 (fr) * 1987-10-01 1989-04-05 Ciba-Geigy Ag Procédé de teinture de fibres cellulosiques ayant une égalité de nuance entre les extrémités du tissu
EP0719621A1 (fr) * 1994-12-28 1996-07-03 ALPI S.p.A. Peinture des feuilles du bois avec des colorants appartenant aux colorants de cuve

Also Published As

Publication number Publication date
EP0055694B1 (fr) 1986-06-04
US4886549A (en) 1989-12-12
JPH0376876A (ja) 1991-04-02
JPH0423031B2 (fr) 1992-04-21
EP0055694A3 (en) 1983-01-19
JPH0329827B2 (fr) 1991-04-25
US4519805A (en) 1985-05-28
ZA818967B (en) 1982-11-24
DE3174788D1 (en) 1986-07-10
JPS57133281A (en) 1982-08-17

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