EP0828023A2 - 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
EP0828023A2
EP0828023A2 EP97114237A EP97114237A EP0828023A2 EP 0828023 A2 EP0828023 A2 EP 0828023A2 EP 97114237 A EP97114237 A EP 97114237A EP 97114237 A EP97114237 A EP 97114237A EP 0828023 A2 EP0828023 A2 EP 0828023A2
Authority
EP
European Patent Office
Prior art keywords
agents
dyeing
printing
agent
weight
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
EP97114237A
Other languages
German (de)
English (en)
Other versions
EP0828023A3 (fr
EP0828023B1 (fr
Inventor
Martin Dr. Riegels
Uwe Dr. Vogt
Klaus Dr. Walz
Fritz Lesszinsky
Bernd Könemund
Torsten Dr. Groth
Winfried Dr. Joentgen
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.)
Lanxess BV
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0828023A2 publication Critical patent/EP0828023A2/fr
Publication of EP0828023A3 publication Critical patent/EP0828023A3/fr
Application granted granted Critical
Publication of EP0828023B1 publication Critical patent/EP0828023B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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
    • 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 agents for dyeing or printing textile materials from natural or synthetic fibers or mixtures thereof, the by content of polyaspartic acid (PAS) or a derivative thereof Marked are.
  • the invention further relates to a method for dyeing or printing on these textile materials using the inventive Agents and the use of these agents for dyeing or printing the mentioned textile materials.
  • Examples of tools with poor biodegradability are sulfonated naphthalene-formaldehyde condensates, oxyethylated fatty amines, lignin sulfonates, polymers or copolymers the (meth) acrylic acid.
  • the invention accordingly relates to agents for dyeing or printing textile materials from natural or synthetic fibers or mixtures of the two Contain polyaspartic acid (PAS) or a derivative thereof and as another Component optionally wetting agents, emulsifiers, leveling agents, dispersing agents, Reducing agents, oxidizing agents, solubilizers, defoamers, Reserving agents, pH regulators, complexing agents or more thereof.
  • PAS Contain polyaspartic acid
  • the invention further relates to a method for dyeing or printing the mentioned textile materials by treating these textile materials with dyeing liquors or printing pastes containing dyeing or printing aids, the is characterized in that these aids PAS or a derivative thereof and as a further component optionally one or more of the above Contain components, the auxiliaries in an amount of 0.2 to 10 % By weight, based on the weight of the goods (weight of the textile materials), be used.
  • the invention also relates to the use of said agents as Aid for dyeing or printing the textile materials mentioned.
  • the agents according to the invention are characterized above all by their content of PAS or a derivative thereof.
  • the most suitable derivatives are salts of PAS, the cations Li ⁇ , Na ⁇ , K ⁇ , Mg ⁇ , Ca ⁇ , NH 4 ⁇ , H 3 N (CH 2 CH 2 OH) ⁇ , H 2 N (CH 2 CH 2 OH) 2 ⁇ or HN (CH 2 CH 2 OH) 3 ⁇ contain.
  • the production and use of PAS and its derivatives has long been the subject of numerous publications and patents. For this, reference is made to J. Org. Chem.
  • the said US '461 describes the production of PAS from maleic anhydride, Water and ammonia.
  • Maleic anhydride is in an aqueous medium with the addition of concentrated ammonia solution in the monoammonium salt transformed.
  • PAS prepared that maleic acid monoammonium salt preferably at 150 to 180 ° C in a reactor with a residence time of 5 to 300 minutes one thermal, optionally continuously carried out polymerization and the polysuccinimide obtained by hydrolysis to PAS or a salt implement it.
  • the PAS contains essentially recurring succinyl units of the following structure: prefers
  • the chemical structure is preferably analyzed using 13 C-NMR, FT-IR and, after total hydrolysis, using HPLC, GC and GC / MS.
  • the pure acids do not fall first the corresponding anhydrides, for example polysuccinimide.
  • Such Polymerization products can optionally be reacted with a base be converted into a PAA-containing salt in the presence of water.
  • This Conversion of PSI-containing to PAA-containing polymers then takes place in a suitable device by hydrolysis.
  • a pH value is preferred suitable between 5 and 14.
  • a pH value is in a particularly preferred form chosen from 7 to 12, in particular by adding a base.
  • Suitable bases are alkali and alkaline earth metal hydroxides or carbonates such as Sodium hydroxide solution, potassium hydroxide solution, soda or potassium carbonate, ammonia and amines such as Triethylamine, triethanolamine, diethylamine, diethanolamine, alkylamines etc. Especially In addition to free acids, preference is given to their Na, K or Ca salts.
  • the temperature in the hydrolysis is suitably in a range including 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.
  • Mw 500 to 10,000, preferably 700 to 5,000, particularly preferably 1,000 to 4,500.
  • PAS can be used as a derivative
  • Polysuccinimide can be used, which at elevated temperature, preferably at 100 to 240 ° C, optionally in the presence of a catalyst, such as in a Amount of 0.01 to 1% by weight, based on the PAS, of an acid catalyst, such as sulfuric acid, phosphoric acid, methanesulfonic acid and others.
  • a catalyst such as in a Amount of 0.01 to 1% by weight, based on the PAS
  • an acid catalyst such as sulfuric acid, phosphoric acid, methanesulfonic acid and others.
  • polysuccinimide also falls in a number of manufacturing processes immediately. In such a case, polysuccinimide can be reacted with a base, optionally in the presence of water, in a salt with one of the cations mentioned above are transferred.
  • Suitable bases for carrying out an alkaline hydrolysis are Alkali and alkaline earth metal hydroxides or carbonates, such as sodium hydroxide solution, Potash lye, soda, potassium carbonate, ammonia and amines, such as Triethylamine, triethanolamine, diethylamine, diethanolamine and ethanolamine.
  • PAS PAS
  • the preparation of such PAS amides can be carried out using the polysuccinimide mentioned 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 after The remaining succinimide structures remaining after the amide formation can subsequently be used through said hydrolytic opening in the presence of bases into free Carboxyl or carboxylate groups are converted.
  • In preferred derivatives contain 5 to 50 mol%, preferably 10 to 35 mol% of the aspartic acid units present such amide structures, while the remaining carboxyl groups are in the form of carboxylate groups.
  • the agents according to the invention contain 5 to 100% by weight, preferably 10 to 50% % By weight of PAS, its derivatives (preferably its salts and amides) or mixtures of these, based on the total weight of the agents according to the invention.
  • PAS its derivatives
  • the Amide groups of PAS derivatives contain saturated or saturated amide nitrogen unsaturated aliphatic radicals with 2 to 20 carbon atoms, which are replaced by hydroxyl groups may be substituted, or cycloaliphatic radicals having 6 to 12 carbon atoms.
  • residues in the amide groups are: hydroxyethyl, hydroxypropyl, Butyl, hexyl, octyl, dodecyl, tetradecyl, hexadecyl, octadecyl, octadecenyl or cyclohexyl.
  • the agents according to the invention can contain further components.
  • the other components include wetting agents, emulsifiers, dispersants or a mixture of several of them, which can be anionic or nonionic in a known manner.
  • Examples are reaction products of aliphatic, araliphatic or aromatic hydroxy compounds, carboxylic acids, carboxylic acid amides or amines with ethylene oxide, whose Schwefelklareschester or phosphoric acid partial esters, fatty acid ester of mono- or polysaccharides or fatty acid sorbitan ester and oxyethylation products thereof, C 10 -C 20 alkanesulfonates, C 8 -C 12 alkyl benzene sulfonates, C 8 -C 18 alkyl sulfates or phosphates or condensed aromatic sulfonic acids, such as naphthalene-formaldehyde sulfonates. Substances of the type mentioned can also serve as leveling agents. They are known to those skilled in the art for these uses.
  • Solubilizers as a further component 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 a further component are, for example, vegetable oils or Defoamers containing mineral oils, in particular propylene oxide-ethylene oxide block polymers.
  • At least one of the other components mentioned is preferably located in front. According to the invention, they are in an amount of 95 to 0% by weight, preferably 90 to 50% by weight, based on the total weight of the agents according to the invention, in front.
  • Textile materials dyed using the agents according to the invention or are printed are fiber materials made of loose fibers, ridges, weaving or Hosiery or nonwovens in the form of natural or synthetic Fibers or their mixtures.
  • natural fibers are wool, Silk, linen, cotton or regenerated cotton, as well as jute or sisal called.
  • synthetic fibers are those made of polyesters, polyamides, Polyurethanes, polyacrylonitrile or polypropylene called.
  • the dyeing or printing of the textile materials is carried out with the used ones Dyes suitable fibers carried out, which the person skilled in the art is known.
  • Suitable classes of dyes for this originate, for example, from Group of acid dyes, sulfo-free or sulfo-containing Metal complexes, reactive dyes, vat dyes, direct dyes, sulfur dyes, cationic dyes, disperse dyes and the pigments.
  • the agents according to the invention are preferably used when dyeing Cotton with direct dyes and reactive dyes when dyeing polyester fibers with disperse dyes or when dyeing cotton-polyester mixed articles used 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 block-cold residence (KKV) procedures and others, as well as within the framework of the Textile printing processes known to those skilled in the art.
  • the ones to be used in the individual procedures Amounts of textile auxiliaries, the temperatures to be used, the Fleet lengths and concentrations are known to the person skilled in the art.
  • the invention Agents are in an amount of 0.2 to 10 wt .-%, based on the Weight of the textile material to be dyed or printed.
  • dyebaths are outstandingly stable and in turn colorations with excellent levelness and brilliance receive.
  • formation of creases is reduced or completely avoided.
  • textile printing can be used as a thickener in dyeing or printing aids, non-environmentally friendly polyacrylate in whole or in part by the inventive Funds to be replaced.
  • the agents according to the invention have excellent biodegradability and therefore contribute to reducing the wastewater load of textile companies at. In the event of partial or total replacement of polyacrylate one continues to use less viscous dyeing liquors.
  • the auxiliary used consisted of an aqueous solution, the 12% of Sodium salt of PAS and 10% of the sodium salt of a sulfonated naphthalene-formaldehyde condensation product contained.
  • Cotton knitwear with a basis weight of 250 g / m 2 was dyed in the manner described in Example 1, using Reactive Blue 116 instead of the dye mentioned there.
  • the used Dyeing liquors had very good stability, which meant that there was no smearing in the dyeing machine and thus no stains appeared on the colored material.
  • Bleached cotton gabardine with a basis weight of 260 g / m 2 was dyed by the block-cold dwelling process with a liquor pick-up of 80%, using a liquor which contained 30 g of Reactive Green 021, 2.5 g of PAS, 2 g in liters a commercially available 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 at 38 ° Be.
  • the residence time of the material in the wet state was 48 hours. After washing out, a green color of excellent levelness was obtained, in which no so-called edge or end drain was observed.
  • a cotton / polyester fabric (80:20) was placed on a tree dyeing machine dyed in a liquor ratio of 1:14 using the two-bath process.
  • the first bath contained 0.385% (based on textile material) of Disperse Yellow 042 and 1.9% Disperse Blue 060 1 g / l of the PAS amide described below as Dispersant and 0.5 g / l of a commercial leveling agent (e.g. a 1: 1 mixture from stearic acid x6 EO and nonylphenol x10 EO).
  • the coloring was started at 80 ° C. With a heating rate of 1 ° C / min Heated 130 ° C and dyed at this temperature for 45 min.
  • the PAS amide used was prepared by mixing 48.4 parts of polysuccinimide and 40.5 parts oleylamine in 103 parts N-methylpyrrolidone to 130 heated to 135 ° C and stirred for 5 hours at this temperature. After this Cooling to 90 to 95 ° C was 295 parts of water and 28 parts of 50% Sodium hydroxide solution and stirred at 95 to 100 ° C for about 1 hour. There were receive approx. 500 parts of a 20% solution of the PAS amide as a slightly cloudy solution, which could be converted into a clear solution by clarification filtration.
  • the coloring could be carried out with the same success if you put in place of this PAS amide in the reactive dye bath used 2 g / l of an agent which consists of 12% a sulfonated naphthalene-formaldehyde condensation product, 10% polyaspartic acid Na salt and 78% water.

Landscapes

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

Publications (3)

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

Family

ID=7804100

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97114237A Expired - Lifetime EP0828023B1 (fr) 1996-08-30 1997-08-18 Agent pour teindre ou imprimer des matériaux textiles

Country Status (6)

Country Link
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
EA201591846A1 (ru) * 2013-05-17 2016-08-31 Ксилеко, Инк. Обработка биомассы

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
US5442038A (en) * 1993-10-06 1995-08-15 Srchem, Inc. Polymers of maleic acid with amines
US5408029A (en) * 1993-10-06 1995-04-18 Srchem, Inc. Amino acid copolymers of maleic acid
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

Also Published As

Publication number Publication date
US5902357A (en) 1999-05-11
JPH1088051A (ja) 1998-04-07
ES2281908T3 (es) 2007-10-01
DE19635061A1 (de) 1998-03-05
DE59712790D1 (de) 2007-02-15
EP0828023A3 (fr) 1998-07-15
EP0828023B1 (fr) 2007-01-03
PT828023E (pt) 2007-05-31

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