Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions

Definitions

• the present invention relates to a composition comprising a nickel complex pigment and a disperse dye and to the use of such a composition in the dyeing or printing of hydrophobic fibre materials and in the production of coloured plastics or polymeric colour particles.
• nickel complex pigments as disperse dyes in the dyeing of polyester fibres is known, for example, from WO 02/057537 and WO 02/055786.
• the dyeings thereby obtained are distinguished by good general fastness properties, especially a high level of fastness to light and to wetting.
• the present invention relates to a composition
• a composition comprising
• R is hydrogen, hydroxy or a radical -NHCO-Re wherein R ⁇ is Cj-Cealkyl or unsubstituted or C ⁇ -C 4 alkyl- or halo-substituted phenyl,
• R 2 is hydrogen, hydroxy or a radical W-R 7 wherein W is -NHCO- or -S- and R 7 is
• R 3 is hydrogen
• Rt is hydrogen or hydroxy
• R 5 is hydrogen, or
• rings A and B independently of one another, may carry
• Rs is hydrogen or -CO-C 2 -C 6 alkyl wherein the C 2 -C 6 alkyl radical may be substituted
• Rn is hydrogen, C C alkyl, hydroxy, carboxy or halogen
• R 12 is hydrogen, C,-C 4 alkyl or halogen
• R, 3 is hydrogen or C ⁇ -C ⁇ alkyl or, when R 10 is halogen
• R 13 may be methyl
• R° is hydrogen or halogen
• R 10 is hydrogen or halogen, and n is a number 0, 1 or 2, with the proviso that R 9 , Rio. Rn, R12 and R1 3 are not all simultaneously hydrogen
• compositions according to the invention preferably comprise as nickel complex pigment (A) a compound of formula (3)
• R 1 and R 15 are each independently of the other CN or halogen or together with the carbon atoms to which they are bonded form an aromatic ring that is unsubstituted or substituted by one or more nitro, cyano, hydroxy, C,-C ⁇ alkyl, ammo or Ci-C ⁇ alkylamino groups or halogen atoms and
• Ri ⁇ to R2 3 are each independently of the others hydrogen, halogen, -NO 2 , -CN, -OH, - COOH, -CH 3 , -NH 2 or -NHCH 3
• An alkyl group as a substrtuent R ⁇ , R7, Rn, R12, R13, as part of a -CO-alkyl group R ⁇ or as a substituent of any aromatic rings which may be present is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, amyl, tert-amyl (1,1-dimethylpropyl), 1 ,1,3,3-tetramethylbutyl, hexyl, 2-methylpentyl, neopentyl, cyclopentyl, cyclohexyl, or a corresponding isomer.
• Halogen is iodine, bromine or especially chlorine.
• Preferred nickel complex pigments of formula (3) are the compounds of formulae (3a) and
• R ⁇ 6 to R 23 are as defined in claim 2 and R 2 to R 27 are each independently of the others hydrogen, halogen, -N0 2 , -CN, -OH, -COOH, -CH 3 , -NH 2 or -NHCH 3 .
• disperse dyes of formula (2) are the compounds of formulae (2a) - (2k)
• Especially preferred disperse dyes (B) are the compounds of formulae (1a) and (2a).
• the anthraquinone dye of formula (2a) is preferably used in the form of a mixture of the isomeric compounds (2a1), (2a2) and (2a3):
• isome ⁇ c compounds (2a1), (2a2) and (2a3) are preferably present in approximately equal amounts
• the nickel complex pigments (A) used according to the invention are known and are desc ⁇ bed, for example, in WO 02/057537 and WO 02/055786
• the disperse dyes (B) are also known, for example from WO 02/051924 and WO 02/051942
• compositions according to the invention comprise additionally (c) a pigment of formula (4) or (5)
• the disperse dyes of formulae (1 ) and (2) are suitable also for the production of mixed shades together with other dyes and especially together with a suitable yellow dye for trichromatic dyeing
• Trichromatic dyeing is to be understood as being the additive colour mixing of suitably selected yellow- or orange-dyeing, red-dyeing and blue-dyeing dyes with which any desired shade of the visible colour spectrum can be achieved by an appropriate choice of the relative proportions of the dye components Since the compositions according to the invention can be used both in mass colouring and in the exhaust process or thermosol process, metamensm effects can be avoided
• compositions comprising as disperse dye (B) a trichromatic mixture comprising at least one blue-dyeing dye of the above formulae (1a) - (1e), at least one red-dyeing dye of the above formulae (2a) - (2k) and the yellow- dyeing dye of formula (6)
• the dye of formula (6) has been known for a long time (C I Solvent Yellow 163) and is commercially available
• the dye mixtures according to the invention can be used in the dyeing and printing of semi- synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials Textile materials composed of blends compnsmg such semi -synthetic and/or synthetic hydrophobic textile materials can likewise be dyed or pnnted using the dye mixtures according to the invention
• Semi-synthetic textile materials that come into consideration are especially cellulose 2 1 / 2 acetate and cellulose t ⁇ acetate
• Synthetic hydrophobic textile mate ⁇ als consist especially of linear, aromatic polyesters, for example those of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-b ⁇ s(hydroxymethyl)cyclohexane, of polycarbonates, e g those of ⁇ , ⁇ -d ⁇ methyl-4,4-d ⁇ hydroxy-d ⁇ phenylmethane and phosgene, and of fibres based on polyvinyl chloride and on polyamide
• polyester fibre materials are dyed in the exhaust process from an aqueous dispersion in the presence of customary anionic or non-ionic dispersants and optionally customary swelling agents (earners) at temperatures of from 80 to 140°C
• Cellulose 2 1 / 2 acetate is dyed preferably at about from 65 to 85°C and cellulose triacetate at temperatures of up to 115°C
• the dye mixtures according to the invention can also be used satisfactorily in the dyeing of polyester blends, for example polyester/cellulosic fibre blends
• the dye mixtures according to the invention are suitable for dyeing in accordance with the thermosol process, in the exhaust and continuous process and for printing processes
• the exhaust process is preferred
• the liquor ratio is dependent upon the nature of the apparatus, the substrate and the form of make-up It may, however, be selected within a wide range, e g from 1 4 to 1 100, but is preferably from 1 6 to 1 25
• the said textile material can be in a variety of processing forms, e g in the form of fibres, yarns or non-wovens, in the form of woven fabrics or knitted fabrics
• the dyes are ground so that their particle size is on average from 0 1 to 10 microns
• the grinding can be carried out in the presence of dispersants
• the dried dye is ground with a dispersa ⁇ t or is kneaded into paste form with a dispersant and then dried in vacuo or by atomisation.
• the preparations so obtained can be used, after the addition of water, to prepare printing pastes and dyebaths.
• the customary thickeners will be used, e.g. modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethylcellulose, hydroxyethylcellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
• modified or unmodified natural products for example alginates, British gum, gum arabic, crystal gum, locust bean flour, tragacanth, carboxymethylcellulose, hydroxyethylcellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
• the dye mixtures according to the invention impart to the mentioned materials, especially to polyester material, level colour shades having very good in-use fastness properties, such as, especially, good fastness to light, more especially very good high-temperature light fastness, as well as a high level of fastness to wetting, such as fastness to water, perspiration and washing.
• the dye mixtures according to the invention additionally comprise UV absorbers.
• the present invention relates also to the use of the compositions according to the invention in the production of coloured plastics or polymeric colour particles.
• the process for the production of coloured plastics or polymeric colour particles comprises mixing together a high molecular weight organic material and a tinctorially effective amount of a dye composition according to the invention.
• the colouring of high molecular weight organic substances with the dye composition is carried out, for example, by mixing the dye composition into those substrates using roll mills, mixing apparatus or grinding apparatus, with the result that the dye composition is dissolved or finely dispersed in the high molecular weight material.
• the high molecular weight organic material with the admixed dye composition is then processed using methods known per s ⁇ , for example calendering, compression moulding, extrusion, coating, spinning, casting or injection moulding, whereby the coloured material acquires its final form. It is also possible for the admixing of the dye composition to be carried out immediately prior to the actual processing step, e.g.
• a dye composition in powder form by continuously feeding a dye composition in powder form and, at the same time, a granulated or pulverulent high molecular weight organic material, and optionally also additional ingredients, e.g. additives, directly into the intake zone of an extruder, where mixing takes place just before processing.
• additional ingredients e.g. additives
• the dye composition it is preferable for the dye composition to be mixed into the high molecular weight organic material beforehand, because more even colouration of the substrates can be obtained
• plasticisers for example, esters of phosphoric acid, phthalic acid or sebacic acid
• plasticisers may be incorporated into the polymers before or after the incorporation of the colorant
• the plasticisers may be incorporated into the polymers before or after the incorporation of the colorant
• further dyes or other colorants in any desired amounts, optionally together with further additives, e g fillers or siccatives
• thermoplastic plastics especially in the form of fibres
• Preferred high molecular weight organic materials suitable for being coloured in accordance with the invention are very generally polymers having a dielectric constant of ⁇ 2 5, especially polyester, polycarbonate (PC), polystyrene (PS), polymethyl methacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene/acrylonit ⁇ le (SAN) and acrylonitrile / butadiene / styrene (ABS)
• Polyester and polyamide are especially preferred
• Very special preference is given to linear aromatic polyesters obtainable by polycondensation of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-b ⁇ s(hydroxymethyl)cyclohexane, for example polyethylene terephthalate (PET), polyt ⁇ methylene terephthalate (PTT) or polybutylene terephthalate (PBTP), also polycarbonates, e
• the resulting mid-grey dyeing has excellent light fastness and very good dry and wet fast-

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Chemistry (AREA)
• Coloring (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Processes Of Treating Macromolecular Substances (AREA)
• Dental Preparations (AREA)
• Pigments, Carbon Blacks, Or Wood Stains (AREA)

Priority Applications (5)

Applications Claiming Priority (2)

Publications (1)

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Cited By (4)

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Citations (5)

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• 2004
  • 2004-04-14 DE DE602004016644T patent/DE602004016644D1/de not_active Expired - Fee Related
  • 2004-04-14 ES ES04727293T patent/ES2315655T3/es not_active Expired - Lifetime
  • 2004-04-14 AT AT04727293T patent/ATE408652T1/de not_active IP Right Cessation
  • 2004-04-14 US US10/553,543 patent/US7435270B2/en not_active Expired - Fee Related
  • 2004-04-14 WO PCT/EP2004/050515 patent/WO2004094532A1/en not_active Ceased
  • 2004-04-14 CN CNB2004800105455A patent/CN100513490C/zh not_active Expired - Fee Related
  • 2004-04-14 DK DK04727293T patent/DK1618154T3/da active
  • 2004-04-14 EP EP04727293A patent/EP1618154B1/en not_active Expired - Lifetime
  • 2004-04-14 JP JP2006505555A patent/JP2006524282A/ja not_active Withdrawn

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