WO2006000359A1 - Derives de melamine, leur production et leur utilisation - Google Patents

Derives de melamine, leur production et leur utilisation Download PDF

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Publication number
WO2006000359A1
WO2006000359A1 PCT/EP2005/006599 EP2005006599W WO2006000359A1 WO 2006000359 A1 WO2006000359 A1 WO 2006000359A1 EP 2005006599 W EP2005006599 W EP 2005006599W WO 2006000359 A1 WO2006000359 A1 WO 2006000359A1
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WO
WIPO (PCT)
Prior art keywords
melamine
melamine derivatives
textile
present
reaction
Prior art date
Application number
PCT/EP2005/006599
Other languages
German (de)
English (en)
Inventor
Eva RÜBA
Günter Scherr
Jürgen Reichert
Wolfram Badura
Manfred Blauth
Martin Reif
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO2006000359A1 publication Critical patent/WO2006000359A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
    • C08G12/36—Ureas; Thioureas
    • C08G12/38—Ureas; Thioureas and melamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32—Melamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/40—Chemically modified polycondensates
    • C08G12/42—Chemically modified polycondensates by etherifying
    • C08G12/424—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds
    • C08G12/425—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds based on triazines
    • C08G12/427—Melamine

Definitions

  • the present invention relates to melamine derivatives obtainable by reacting melamine with 1 to less than 3 equivalents of at least one aliphatic aldehyde and subsequent etherification with 4.5 to 15 equivalents of at least one polyhydric aliphatic alcohol. Furthermore, the present invention relates to a process for the preparation of melamine derivatives according to the invention and their use.
  • Polystyrene resin in particular reaction products of melamine with aliphatic aldehydes, are used in textile chemistry, for example as crosslinkers.
  • Crosslinkers are used, for example, for fixing prints and dyeings, but also for crease-resistant finishing and for improving the washing permanence of other finishes, such as hydrophobing, oleophobization, embossing, gloss and flameproof finishing.
  • the effectiveness of such reagents is still to be improved.
  • DE-A 20 05 166 discloses that melamine can be reacted with 2 to 6 mol of formaldehyde in the presence of 0.4 to 1.2 mol of a di- or trihydric alcohol and thereby be etherified, for example in the form of a one-pot reaction (US Pat. Example 5), preferably in the presence of alkali. Subsequently, the 2- or 3-tigen alcohol is exchanged for a monohydric alcohol, for example against propanol or especially ethanol or methanol. It is proposed that the reaction products prepared in which the 2-or 3-hydric alcohol has been replaced by a monohydric alcohol are used for wrinkle-free finishing of textiles.
  • No. 3,351,615 discloses condensation products of melamine and formaldehyde with a polyhydric alcohol in a molar ratio of melamine: formaldehyde: polyhydric alcohol such as 1: (3 to 6): (0.1 to 0.5).
  • the derivatives according to the invention are obtainable by reacting melamine with one to less than three, preferably from 1.4 to 2.8, more preferably from 2.4 to 2.6, equivalents of at least one aliphatic aldehyde selected from aliphatic monoaldehydes, for example propionaldehyde , Acetaldehyde and in particular formaldehyde, and from aliphatic dialdehydes such as, for example, glyoxal and glutaraldehyde. Then etherified with 4.5 to 15 equivalents, preferably to 8 and more preferably to 6 equivalents of at least one polyhydric aliphatic see alcohol.
  • Aliphatic polyhydric alcohols are selected from alcohols having two or more hydroxyl groups per molecule, preferably two or three and more preferably two.
  • aliphatic polyhydric alcohols are sorbitol, pentaerythritol, diglycerol, triglycerol;
  • Another object of the present invention is a process for the preparation of melamine derivatives according to the invention.
  • the inventive method is characterized in that first melamine with 1 to less than 3 equivalents, preferably 1.4 to 2.8, more preferably reacted with 2.4 to 2.6 equivalents of at least one aliphatic aldehyde and the reaction product then with 4 , 5 to 15 equivalents, preferably etherified to 8 and more preferably to 6 equivalents least one polyhydric aliphatic alcohol.
  • the reaction of melamine with at least one aliphatic aldehyde is carried out in aqueous solution, preferably at pH values in the range from 7 to 10, particularly preferably at pH values in the range from 8 to 9.
  • aqueous solution preferably at pH values in the range from 7 to 10
  • use of water is dispensed with and melamine and at least one aldehyde, in particular melamine and paraformaldehyde, are mixed together, and the two reactants react with one another.
  • the reaction of melamine is carried out with at least one aliphatic aldehyde, at temperatures ranging from 50 to 13O 0 C, preferably 0 to 90 C in the range of 70th
  • the reaction of melamine with at least one aliphatic aldehyde is carried out at atmospheric pressure. In another embodiment of the present invention, the reaction of melamine with at least one aliphatic aldehyde is carried out at pressures in the range from 1:01 to 50 bar, preferably up to 6 bar.
  • the reaction of melamine with at least one aliphatic aldehyde is carried out in the presence of at least one catalyst, for example sodium hydroxide, potassium hydroxide, calcium hydroxide (lime) or ammonium hydroxide.
  • at least one catalyst for example sodium hydroxide, potassium hydroxide, calcium hydroxide (lime) or ammonium hydroxide.
  • the etherification is carried out with at least one polyhydric aliphatic alcohol in the aqueous phase at pH values in the range from 1 to 6, preferably in the range from 4 to 5.5.
  • the desired pH values can be set by adding acid such as, for example, trifluoroacetic acid, methylsulfonic acid, para-toluenesulfonic acid, benzenesulfonic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the etherification is carried out with at least one polyhydric aliphatic alcohol at atmospheric pressure. In another embodiment of the present invention, the etherification is carried out with a polyhydric aliphatic alcohol at pressures in the range of 1, 01 to 50 bar.
  • etherification After completion of the etherification can be distilled unreacted aliphatic aldehyde. It is also possible to dispense with distilling off and unreacted aliphatic aldehyde by suitable reagents, such as oxidizing agents such. As nitric acid or chemically bind by so-called formaldehyde scavenger and thus remove from the reaction mixture, preferably z.
  • suitable reagents such as oxidizing agents such.
  • formaldehyde scavenger As nitric acid or chemically bind by so-called formaldehyde scavenger and thus remove from the reaction mixture, preferably z.
  • urea N 1 N'-di- methylurea, ethylene urea, 1 H-benzotriazole.
  • the process according to the invention is carried out by at least partially distilling off between the reaction of melamine with at least one aldehyde and the etherification, if appropriate, of solvent and unreacted aldehyde used.
  • the process according to the invention is carried out by eliminating distillations between the reaction of melamine with at least one aldehyde and etherification with at least one polyhydric aliphatic alcohol.
  • aqueous solution of basic alkyl metal salts such as aqueous sodium carbonate solution, aqueous potassium carbonate solution, aqueous sodium hydroxide solution or aqueous potassium hydroxide solution.
  • Meiaminderivate for example by evaporation of any solvents used, in particular water.
  • a particularly suitable method for the isolation of melamine derivatives according to the invention is spray-drying.
  • dispersions according to the invention and, in particular, aqueous dispersions according to the invention contain in the range from 0.1 to 70% by weight melamine derivative according to the invention, preferably from 30 to 60% by weight.
  • salts of mono- or divalent metals or ammonium salts to dispersions of the invention and, in particular, aqueous dispersions according to the invention.
  • suitable salts are ZnCl 2 , Zn (NO 3 ) 2 , in each case also in the form of their hydrates, NH 4 Cl, (NH 4 J 2 SO 4 and very particularly preferably MgCl 2 , for example in the form of its hexahydrate dispersions according to the invention and in particular aqueous dispersions according to the invention, it is generally sufficient to add up to 30% by weight, based on the melamine derivative according to the invention, preferably from 1 to 20% by weight of one or more salts of monovalent or divalent metals or ammonium salts .-%.
  • one or more acids to dispersions according to the invention and in particular to aqueous dispersions of the invention preferably organic acids such as, for example, formic acid, acetic acid, C 12 -C 20 fatty acids such as, for example, stearic acid, oxalic acid, citric acid or tartaric acid. If one wishes to add one or more acids to dispersions according to the invention and particular aqueous dispersions of the invention, it is generally sufficient to contain up to 5% by weight, based on the melamine derivative according to the invention, preferably from 0.1 to 2% by weight.
  • dispersions of the invention have a pH in the range from 5.5 to 10, preferably 6 to 8.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne des dérivés de mélamine. Ces dérivés sont obtenus par la réaction de la mélamine avec 1 à moins de 3 équivalents d'au moins un aldéhyde aliphatique puis par éthérification avec de 4,5 à 15 équivalents d'au moins un alcool aliphatique polyvalent.
PCT/EP2005/006599 2004-06-25 2005-06-18 Derives de melamine, leur production et leur utilisation WO2006000359A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200410030926 DE102004030926A1 (de) 2004-06-25 2004-06-25 Melaminderivate, ihre Herstellung und Verwendung
DE102004030926.4 2004-06-25

Publications (1)

Publication Number Publication Date
WO2006000359A1 true WO2006000359A1 (fr) 2006-01-05

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ID=34970674

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Application Number Title Priority Date Filing Date
PCT/EP2005/006599 WO2006000359A1 (fr) 2004-06-25 2005-06-18 Derives de melamine, leur production et leur utilisation

Country Status (2)

Country Link
DE (1) DE102004030926A1 (fr)
WO (1) WO2006000359A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008148842A1 (fr) * 2007-06-06 2008-12-11 Basf Se Méthylol triaminotriazine éther hautement ramifié et non réticulé

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB640203A (en) * 1941-08-27 1950-07-12 Beck Koller And Company Englan A process for producing dihydric alcohol modified melamine formaldehyde condensation products
DE2609696A1 (de) * 1975-03-12 1976-09-23 Serlachius Oy Verfahren zur verbesserung der mechanischen eigenschaften von kunststoff, wie melaminharz
EP0052211A1 (fr) * 1980-11-19 1982-05-26 BASF Aktiengesellschaft Agent pour la modification de résines aminoplastes et procédé pour sa préparation
EP0262518A1 (fr) * 1986-09-25 1988-04-06 CASSELLA Aktiengesellschaft Procédé de préparation de résines mélamine-formaldéhyde
EP1065227A2 (fr) * 1999-06-22 2001-01-03 Clariant (France) S.A. Amélioration de la couleur des résines diméthoxyéthanal-mélamine

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB640203A (en) * 1941-08-27 1950-07-12 Beck Koller And Company Englan A process for producing dihydric alcohol modified melamine formaldehyde condensation products
DE2609696A1 (de) * 1975-03-12 1976-09-23 Serlachius Oy Verfahren zur verbesserung der mechanischen eigenschaften von kunststoff, wie melaminharz
EP0052211A1 (fr) * 1980-11-19 1982-05-26 BASF Aktiengesellschaft Agent pour la modification de résines aminoplastes et procédé pour sa préparation
EP0262518A1 (fr) * 1986-09-25 1988-04-06 CASSELLA Aktiengesellschaft Procédé de préparation de résines mélamine-formaldéhyde
EP1065227A2 (fr) * 1999-06-22 2001-01-03 Clariant (France) S.A. Amélioration de la couleur des résines diméthoxyéthanal-mélamine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008148842A1 (fr) * 2007-06-06 2008-12-11 Basf Se Méthylol triaminotriazine éther hautement ramifié et non réticulé

Also Published As

Publication number Publication date
DE102004030926A1 (de) 2006-01-12

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