EP0828023B1 - Agent pour teindre ou imprimer des matériaux textiles - Google Patents

Agent pour teindre ou imprimer des matériaux textiles Download PDF

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Publication number
EP0828023B1
EP0828023B1 EP97114237A EP97114237A EP0828023B1 EP 0828023 B1 EP0828023 B1 EP 0828023B1 EP 97114237 A EP97114237 A EP 97114237A EP 97114237 A EP97114237 A EP 97114237A EP 0828023 B1 EP0828023 B1 EP 0828023B1
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EP
European Patent Office
Prior art keywords
agents
acid
process according
dyestuffs
dyeing
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.)
Expired - Lifetime
Application number
EP97114237A
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German (de)
English (en)
Other versions
EP0828023A2 (fr
EP0828023A3 (fr
Inventor
Martin Dr. Riegels
Uwe Dr. Vogt
Klaus Dr. Walz
Fritz Lesszinsky
Bernd Könemund
Torsten Dr. Groth
Winfried Dr. Joentgen
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Lanxess BV
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Lanxess BV
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Publication of EP0828023B1 publication Critical patent/EP0828023B1/fr
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Expired - Lifetime 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5278—Polyamides; Polyimides; Polylactames; Polyalkyleneimines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/926—Polyurethane fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/927—Polyacrylonitrile fiber
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/928—Polyolefin fiber

Definitions

  • the present invention relates to a process for dyeing or printing textile materials from wool, cotton, regenerated cotton, jute, sisal, polyester, polyamides, polyurethanes, polyacrylonitrile or polypropylene fibers or mixtures thereof using agents which contain polyaspartic acid (PAS). or a derivative thereof.
  • PAS polyaspartic acid
  • the invention further relates to the use of these agents for dyeing or printing said textile materials.
  • aids with poor biodegradability are sulfonated naphthalene-formaldehyde condensates, ethoxylated fatty amines, lignosulfonates, polymers or copolymers of (meth) acrylic acid.
  • DE-A 4 439 990 discloses leather tanning agents and colorants for dyes which contain, inter alia, polyaspartic acid, its salts and anhydrides.
  • DE-A-2 253 190 discloses polyamino acid derivatives, processes for their preparation and their use as surfactants, as well as detergents and cosmetics containing these compounds.
  • the invention relates to a process for dyeing or printing the textile materials mentioned by treating these textile materials with dyeing liquors or printing pastes which contain dyeing or printing auxiliaries, which is characterized in that these auxiliaries PAS or a derivative thereof and as further component optionally one or more contain the above-mentioned components, wherein the aids in an amount of 0.2 to 10 wt .-%, based on the weight of the goods (weight of the textile materials) are used.
  • the invention also relates to the use of said agents as auxiliaries for dyeing or printing said textile materials.
  • the agents to be used in the process according to the invention are characterized above all by their content of PAS or a derivative thereof.
  • As derivatives of the PAS in question as cations Li ⁇ , Na ⁇ , K ⁇ , Mg ⁇ , Ca ⁇ , NH 4 ⁇ , H 3 N come above all salts (CH 2 CH 2 OH) ⁇ , H 2 N (CH 2 CH 2 OH) 2 ⁇ or HN (CH 2 CH 2 OH) 3 ⁇ included.
  • the manufacture and use of PAS and its derivatives has long been the subject of numerous publications and patents. Reference may be made to J. Org. Chem.
  • Said US '461 describes the preparation of PAS from maleic anhydride, water and ammonia.
  • Maleic anhydride is converted to the monoammonium salt in an aqueous medium with the addition of concentrated ammonia solution.
  • PAS is prepared by subjecting maleic ammonium salt to a thermal, optionally continuous, polymerization at 150 to 180 ° C. in a reactor at a residence time of 5 to 300 minutes, and to obtain the obtained polysuccinimide by hydrolysis to give PAS or a salt implemented.
  • the analysis of the chemical structure is preferably carried out with 13 C-NMR, FT-IR and after total hydrolysis with HPLC, GC and GC / MS.
  • Suitable bases are alkali metal hydroxides and alkaline earth metal hydroxides or carbonates such as, for example, sodium hydroxide solution, potassium hydroxide solution, soda or potassium carbonate, ammonia and amines such as triethylamine, triethanolamine, diethylamine, diethanolamine, alkylamines, etc. Particular preference is given to free acids in addition to their Na, K or Ca. salts.
  • the temperature in the hydrolysis is suitably in a range up to the boiling point of the PSI suspension and preferably at 20 to 150 ° C.
  • the hydrolysis is optionally carried out under pressure.
  • the finished product is obtained by drying, preferably spray drying.
  • the proportion of the beta-form is more than 50%, preferably more than 70%.
  • Polysuccinimide which can be used at elevated temperature, preferably at 100 to 240 ° C., if appropriate in the presence of a catalyst, such as in an amount of 0.01 to 1% by weight, can be used as a derivative of PAS in addition to the salts with the abovementioned cations.
  • a catalyst such as in an amount of 0.01 to 1% by weight
  • an acid catalyst such as sulfuric acid, phosphoric acid, methanesulfonic acid and others occur.
  • polysuccinimide is also directly involved in a number of manufacturing processes. In such a case, polysuccinimide may be converted to a salt having one of the above-mentioned cations by reaction with a base, optionally in the presence of water.
  • Suitable bases for carrying out an alkaline hydrolysis are alkali metal and alkaline earth metal hydroxides or carbonates, for example sodium hydroxide solution, potassium hydroxide solution, soda, potassium carbonate, furthermore ammonia and amines, such as triethylamine, triethanolamine, diethylamine, diethanolamine and ethanolamine.
  • PAS PAS
  • the preparation of such PAS amides can be carried out from said polysuccinimide with primary or secondary amines (DE-A 22 53 190, EP 274 127, EP 406 623, EP 519 119, US 3,846,380, US 3,927,204, US 4,363. 797).
  • the residual succinimide structures remaining after amide formation can then be converted to free carboxyl or carboxylate groups by the said hydrolytic opening in the presence of bases.
  • from 5 to 50 mol%, preferably from 10 to 35 mol%, of the aspartic acid units present contain such amide structures, while the remaining carboxyl groups are present in the form of carboxylate groups.
  • the agents to be used in the process according to the invention contain from 5 to 100% by weight, preferably from 10 to 50% by weight of PAS, their derivatives (preferably their salts and amides) or mixtures thereof, based on the total weight of the compositions.
  • the amide groups of PAS derivatives contain at the amide nitrogen saturated or unsaturated aliphatic radicals having 2 to 20 carbon atoms, which may be substituted by hydroxyl groups, or cycloaliphatic radicals having 6 to 12 carbon atoms.
  • radicals in the amide groups are: hydroxyethyl, hydroxypropyl, butyl, hexyl, octyl, dodecyl, tetradecyl, hexadecyl, octadecyl, octadecenyl or cyclohexyl.
  • the agents to be used in the process according to the invention may contain, in addition to their content of PAS or a derivative thereof, further components.
  • further components are wetting agents, emulsifiers, dispersants or a mixture of several of them, which may be anionic or non-ionic in a known manner.
  • Solubilizers as further components are, for example, glycols, mono- to tetraalkylene glycols, their ethers or esters with C 1 -C 4 -alcohols or C 1 -C 4 -carboxylic acids.
  • Defoamers as further components are, for example, defoamers containing vegetable oils or mineral oils, in particular propylene oxide-ethylene oxide block polymers.
  • reducing agents oxidizing agents, reserving agents, pH regulators, complexing agents or more of them may be present in an amount of from 0 to 10% by weight, based on the total weight of the agents to be employed in the process according to the invention, which amounts to the amount PAS and the surfactants mentioned above.
  • the use of such agents is familiar to the skilled worker and described, for example, in Chwala / Anger, Handbuch der Textilosstoff, Verlag Chemie, Weinheim 1977.
  • At least one of said other components is present. According to the invention, they are present in an amount of 95 to 0% by weight, preferably 90 to 50% by weight, based on the total weight of the compositions according to the invention.
  • Textile materials which are dyed or printed using the agents to be used in the process according to the invention are wool, cotton or regenerated cotton, as well as jute or sisal.
  • polyesters such as polyesters, polyamides, polyurethanes, polyacrylonitrile or polypropylene may be mentioned.
  • the dyeing or printing of the textile materials is carried out with the dyes suitable for the fibers used, which is basically known to the person skilled in the art.
  • Suitable classes of dyes for this purpose are derived, for example, from the group of acid dyes, sulfo groups-free or sulfo-containing metal complexing agents, reactive dyes, vat dyes, direct dyes, sulfur dyes, cationic dyes, disperse dyes and pigments.
  • the agents to be used in the process according to the invention are preferably used for dyeing cotton with direct dyes and reactive dyes, dyeing polyester fibers with disperse dyes or dyeing cotton-polyester blends with direct or reactive dyes and disperse dyes.
  • the dyeing or printing of the textile materials mentioned takes place in known processes, such as in the exhaust process, in the continuous process, in the cold pad-stay (KKV) process and others, as well as in the textile printing process known to the person skilled in the art.
  • the amounts of textile auxiliaries to be used in the individual processes, the temperatures to be used, the liquor lengths and concentrations are known to the person skilled in the art.
  • the agents to be used in the process according to the invention are used in an amount of from 0.2 to 10% by weight, based on the weight of the textile material to be dyed or printed.
  • the agents to be used in the process according to the invention have excellent biodegradability and therefore contribute to a reduction in the wastewater load of textile factories. In the case of the partial or complete replacement of polyacrylate obtained further low viscose dyeing liquors.
  • 100 g of bleached cotton yarn were dyed in a cross-dyeing apparatus at a liquor ratio of 1:10 at 80 ° C using a dyeing liquor containing per liter 4 g Reactive Green 021 and 2 g of the adjuvant described below. After a dyeing time of 10 minutes, 80 g of sodium chloride were added, after a further 30 minutes 5 g of sodium bicarbonate and, after 30 minutes, finally 10 g of sodium carbonate. The staining was completed in another 60 minutes. A dyeing of excellent levelness was obtained and there were no filtrations visible on the bobbin.
  • the auxiliary used consisted of an aqueous solution containing 12% of the sodium salt of PAS and 10% of the sodium salt of a sulfonated naphthalene-formaldehyde condensation product.
  • Cotton knit fabric having a basis weight of 250 g / m 2 was dyed in the manner described in Example 1 using Reactive Blue 116 instead of the dyestuff mentioned therein.
  • the dyeing liquors used had a very good stability, as a result of which no smears were produced in the dyeing apparatus and thus no stains on the dyed material.
  • Bleached cotton gabardine having a basis weight of 260 g / m 2 was dyed by the pad cold pad process at a liquor pick-up of 80% using a liquor which was 30 g in Reactive Green 021, 2.5 g PAS, 2 g a commercial wetting agent (eg a reaction product of isotridecanol with 6 moles of ethylene oxide), 20 g of sodium carbonate and 3 g of sodium hydroxide solution of 38 ° Be contained.
  • the residence time of the material in the wet state was 48 hours. After washing, a green color of excellent levelness was obtained, in addition, no so-called edge or end effluent was observed.
  • a fabric of cotton / polyester (80:20) was dyed on a Baumfärbeapparat in the liquor ratio 1:14 by the two-bath method.
  • the first bath contained besides 0.385% (based on textile material) Disperse Yellow 042 and 1.9% Disperse Blue 060 1 g / l of the PAS amide described below as dispersing agent and 0.5 g / l of a commercially available leveling agent (eg a 1 : 1-mixture of stearic acid x6 EO and nonylphenol x10 EO).
  • the staining was started at 80 ° C. With a heating rate of 1 ° C / min was heated to 130 ° C and dyed at this temperature for 45 min.
  • the PAS amide used was prepared by heating 48.4 parts of polysuccinimide and 40.5 parts of oleylamine in 103 parts of N-methylpyrrolidone at 130 to 135 ° C and stirred for 5 hours at this temperature. After cooling to 90 to 95 ° C were set to 295 parts of water and 28 parts of 50% sodium hydroxide solution and stirred for about 1 hour at 95 to 100 ° C after. About 500 parts of a 20% strength solution of the PAS amide were obtained as a slightly turbid solution, which could be converted into a clear solution by a clarification filtration.
  • the dyeing could be carried out with equal success if 2 g / l of an agent consisting of 12% of a sulfonated naphthalene-formaldehyde condensation product, 10% polyaspartic acid sodium salt and 78% water were used instead of this PAS amide in the reactive dyebath duration.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Claims (11)

  1. Procédé pour la teinture ou l'impression de matériaux textiles à base de laine, coton, coton régénéré, jute, sisal, fibres de polyester, de polyamide, de polyuréthanne, de polyacrylonitrile, de polypropylène ou de mélanges de ceux-ci, caractérisé en ce qu'on traite ces matériaux textiles par des bains de teinture ou des pâtes à imprimer qui contiennent en tant qu'adjuvants du poly(acide aspartique) ou un dérivé de celui-ci et un ou plusieurs composants tels que des agents mouillants, des agents d'unisson, des dispersants, des réducteurs, des oxydants, des tiers-solvants, des antimousses, des agents de réserve, des régulateurs du pH, des complexants et les adjuvants sont utilisés en une quantité de 0,2 à 10 % en poids, par rapport au poids des matériaux textiles à imprimer ou à teindre.
  2. Procédé selon la revendication 1, caractérisé en ce qu'on utilise comme dérivés du poly(acide aspartique) des sels qui contiennent en tant que cations Li⊕, Na⊕, K⊕, Mg⊕⊕, Ca⊕⊕, NH4 ⊕, H3N(CH2CH2OH)⊕ , H2N(CH2CH2OH)2 ⊕ ou HN(CH2CH2OH)3 ⊕ ou du polysuccinimide.
  3. Procédé selon la revendication 1, caractérisé en ce que le poly(acide aspartique) contient des motifs répétitifs succinyle de formule
    Figure imgb0016
     de préférence
    Figure imgb0017
    Figure imgb0018
  4. Procédé selon la revendication 1, caractérisé en ce que le poly(acide aspartique), au moyen d'une conduite de réaction appropriée et d'un choix convenable des produits de départ, contient d'autres motifs répétitifs tels que
    a) des motifs acide malique de formule
    Figure imgb0019
     ou
    b) des motifs acide maléique et acide fumarique de formule
    Figure imgb0020
  5. Procédé selon la revendication 1, caractérisé en ce que les autres composants sont présents en une quantité de 90 à 50 % en poids, par rapport au poids total des compositions selon l'invention.
  6. Procédé selon la revendication 1, caractérisé en ce que le matériau textile est un fil de coton blanchi et le bain de teinture contient le colorant vert Reactive Green 021 ou le colorant bleu Reactive Blue 116, le sel sodique du poly(acide aspartique) et le sel sodique d'un produit de condensation de naphtalène et formaldéhyde sulfoné.
  7. Procédé selon la revendication 1, caractérisé en ce qu'on utilise comme poly(acide aspartique) essentiellement un poly(acide aspartique) β ayant une masse moléculaire de 500 à 10 000, entendue en tant que moyenne en poids.
  8. Procédé selon la revendication 1, caractérisé en ce qu'on utilise comme dérivés de poly(acide aspartique) ceux dans lesquels une partie des groupes carboxy présents dans le poly(acide aspartique) se trouvent sous forme d'amides.
  9. Procédé selon la revendication 1, caractérisé en ce qu'on utilise comme agents mouillants, émulsifiants ou dispersants des produits de réaction de composés hydroxylés, d'acides carboxyliques, de carboxamides ou d'amines, aliphatiques, araliphatiques ou aromatiques, avec l'oxyde d'éthylène, leurs hémiesters avec l'acide sulfurique ou esters partiels avec l'acide phosphorique, des esters d'acides gras et de mono-ou polysaccharides ou des esters d'acides gras et de sorbitanne et leurs produits d'oxyéthylation, des alcane(C10-C20) sulfonates, des alkyl(C8-C12)-benzènesulfonates, des alkyl(C8-C18)sulfates ou -phosphates ou des acides sulfoniques aromatiques condensés, tels que des naphtalène-formaldéhyde-sulfonates.
  10. Procédé selon la revendication 1, caractérisé en ce que les bains de teinture ou les pâtes à imprimer contiennent des colorants choisis dans le groupe des colorants acides, des colorants à complexes métallifères exempts de groupes sulfo ou contenant des groupes sulfo, des colorants réactifs, des colorants de cuve, des colorants directs, des colorants soufrés, des colorants cationiques, des colorants en dispersion et des pigments.
  11. Utilisation de poly(acide aspartique) ou d'un dérivé de celui-ci et d'un ou plusieurs composants tels que des agents mouillants, des agents d'unisson, des dispersants, des réducteurs, des oxydants, des tiers-solvants, des antimousses, des agents de réserve, des régulateurs du pH, des complexants en une quantité de 0,2 à 10 % en poids, par rapport au poids des matériaux textiles à imprimer ou à teindre, caractérisée en ce que ceux-ci sont utilisés dans des bains de teinture ou des pâtes à imprimer pour la teinture ou l'impression de matériaux textiles à base de laine, coton, coton régénéré, jute, sisal, polyesters, polyamides, polyuréthannes ou fibres de polypropylène ou de mélanges de ceux-ci.
EP97114237A 1996-08-30 1997-08-18 Agent pour teindre ou imprimer des matériaux textiles Expired - Lifetime EP0828023B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19635061A DE19635061A1 (de) 1996-08-30 1996-08-30 Mittel zum Färben oder Bedrucken von Textilmaterialien
DE19635061 1996-08-30

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EP0828023A2 EP0828023A2 (fr) 1998-03-11
EP0828023A3 EP0828023A3 (fr) 1998-07-15
EP0828023B1 true EP0828023B1 (fr) 2007-01-03

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US (1) US5902357A (fr)
EP (1) EP0828023B1 (fr)
JP (1) JPH1088051A (fr)
DE (2) DE19635061A1 (fr)
ES (1) ES2281908T3 (fr)
PT (1) PT828023E (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19822603A1 (de) * 1998-05-20 1999-11-25 Goldschmidt Ag Th Pigmentpasten enthaltend hydrophob modifizierte Polyasparaginsäurederivate
US6365706B1 (en) 2000-06-21 2002-04-02 Mississippi Chemical Corporation Process for production of polyasparagine and the high nitrogen content polymer formed thereby
US6495658B2 (en) 2001-02-06 2002-12-17 Folia, Inc. Comonomer compositions for production of imide-containing polyamino acids
US7294672B2 (en) * 2003-03-31 2007-11-13 Polymer Chemistry Innovations, Inc. Method to form polymeric materials by reverse suspension/emulsion polymerization and compositions formed using that method
MY180366A (en) * 2013-05-17 2020-11-28 Xyleco Inc Processing biomass

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3927204A (en) * 1969-07-03 1975-12-16 Sclavo Inst Sieroterapeut Use of {60 ,{62 -poly-(aspartic acid)-hydroxyalkylamides as a plasma expander
JPS4851995A (fr) * 1971-11-01 1973-07-21
US3846380A (en) * 1972-10-31 1974-11-05 M Teranishi Polyamino acid derivatives and compositions containing same
US4363797A (en) * 1977-09-14 1982-12-14 Societe Anonyme Dite: L'oreal Polyaspartic acid derivatives, their preparation and their use in cosmetic composition
FR2457306A1 (fr) * 1979-05-25 1980-12-19 Oreal Nouveaux produits colorants, leur preparation et leur utilisation dans des compositions colorantes
DE3626672A1 (de) * 1986-08-07 1988-02-11 Bayer Ag Polyasparaginamidsaeure
DE3700128A1 (de) * 1987-01-03 1988-07-14 Hoechst Ag Biologisch abbaubare poly- (hydroxyalkyl)- aminodicarbonsaeure-derivate, verfahren zu ihrer herstellung und verwendung derselben fuer depotzubereitungen mit kontrollierter wirkstoffabgabe
US5131768A (en) * 1988-02-18 1992-07-21 Seiko Epson Corporation Replenishing an ink transfer sheet
DE3921912A1 (de) * 1989-07-04 1991-01-17 Roehm Gmbh Polyasparaginsaeurederivate als ueberzugsmittel fuer arzneiformen und lebensmittel
CA2056035A1 (fr) * 1991-06-18 1992-12-19 Walton B. Caldwell Polyamides portant des chaines laterales fonctionnalisees, utiles comme agents hypolipidemiques hydrosolubles
US5288783A (en) * 1992-05-14 1994-02-22 Srchem Incorporated Preparation of salt of polyaspartic acid by high temperature reaction
DE4221875A1 (de) * 1992-07-03 1994-01-05 Basf Ag Modifizierte Polyasparaginsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung
US5296578A (en) * 1992-09-18 1994-03-22 Donlar Corporation Production of polysuccinimide and polyaspartic acid from maleic anhydride and ammonia
US5393868A (en) * 1992-10-13 1995-02-28 Rohm And Haas Company Production of polysuccinimide by thermal polymerization of maleamic acid
DE4307114A1 (de) * 1993-03-06 1994-09-08 Basf Ag Verfahren zur Herstellung von Umsetzungsprodukten aus Polyasparaginsäureamid und Aminosäuren und ihre Verwendung
US5408029A (en) * 1993-10-06 1995-04-18 Srchem, Inc. Amino acid copolymers of maleic acid
US5442038A (en) * 1993-10-06 1995-08-15 Srchem, Inc. Polymers of maleic acid with amines
DE4439990A1 (de) * 1994-11-09 1996-05-15 Bayer Ag Ledergerbstoffe und Stellmittel für Farstoffe
DE19545678A1 (de) * 1995-12-07 1997-06-12 Goldschmidt Ag Th Copolymere Polyaminosäureester
JPH09207427A (ja) * 1996-01-31 1997-08-12 Mitsubishi Chem Corp インクジェット記録用紙

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US5902357A (en) 1999-05-11
EP0828023A2 (fr) 1998-03-11
DE19635061A1 (de) 1998-03-05
PT828023E (pt) 2007-05-31
ES2281908T3 (es) 2007-10-01
EP0828023A3 (fr) 1998-07-15
DE59712790D1 (de) 2007-02-15
JPH1088051A (ja) 1998-04-07

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