WO2009121856A1 - Compositions contenant une alcanolamine - Google Patents

Compositions contenant une alcanolamine Download PDF

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Publication number
WO2009121856A1
WO2009121856A1 PCT/EP2009/053769 EP2009053769W WO2009121856A1 WO 2009121856 A1 WO2009121856 A1 WO 2009121856A1 EP 2009053769 W EP2009053769 W EP 2009053769W WO 2009121856 A1 WO2009121856 A1 WO 2009121856A1
Authority
WO
WIPO (PCT)
Prior art keywords
compositions
alkanolamine
alkyl group
weight
compositions according
Prior art date
Application number
PCT/EP2009/053769
Other languages
German (de)
English (en)
Inventor
Michael Jahn
Stefan Lehner
Dag Wiebelhaus
Joachim-Thierry Anders
Manfred Dargatz
Original Assignee
Basf Se
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 Se filed Critical Basf Se
Publication of WO2009121856A1 publication Critical patent/WO2009121856A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds

Definitions

  • the invention relates to compositions which are suitable as a coating composition, sealant or adhesive and an alkanolamine of the formula I.
  • R 1 is a C 1 to C 4 alkyl group
  • R 2 is a hydrogen atom or a C 1 to C 4 alkyl group
  • R 3 is an H atom or a C 1 to C 4 alkyl group
  • R 4 and R 5 are independently a C 1 to C 4 alkyl group.
  • Alkanolamines are used in aqueous coating compositions, in particular as neutralizing agent and dispersant. Encyclopedia of Chemical Technology, Volume 2, 1992, pages 1 to 34 describes a variety of suitable alkanolamines. Of particular importance is 2-amino-2-methyl-1-propanol (AMP) or the corresponding dimethylated compound 2-dimethylamino-2-methyl-1-propanol (DMAMP), which is also described in G. N. Robinson, Proc. 3rd Intern. Congress on Paints, Vol. 1, 212 - 223, Sao Paulo 1993 and, moreover, have special significance as commercial products. Suitable alkanolamines are also described in EP-A-1 362 897. WO 2006/016991 and WO 2005/055720 disclose the use of alkanolamines as a biocide for aqueous systems.
  • the coatings, seals or bonds produced should have the best possible performance properties, in particular very good mechanical properties such as elasticity and hardness, but also the resistance to solvents and especially water are generally desired.
  • the resistance to water is often problematic, especially for aqueous coating compositions, sealants or adhesives, since the binders and / or pigments used are generally water-soluble or water-dispersible prior to their use. Inadequate water resistance often leads to clouding of the resulting coating, bonding or sealing, also called whitening.
  • Object of the present invention were therefore coating compositions, sealants or adhesives containing alkanolamines having a good neutralizing and / or dispersing action; the performance properties, the solvent and in particular the water resistance of the resulting coatings, seals or bonds should be as good as possible.
  • compositions defined above were found.
  • the compositions according to the invention contain an alkanolamine of the above formula I.
  • R 1 and R 2 are a C 1 to C 4 alkyl group.
  • the alkyl group is a methyl group, i. R1 and R2 represent a methyl group.
  • a most preferred compound is therefore N, N-dimethyl-1-amino-2-methyl-2-propanol (R1 and R2 methyl).
  • alkanolamines are obtainable in a known manner by reacting amines with epoxides of the formula
  • compositions contain the alkanolamine is preferably present in an amount of 0.05 to 10 wt .-%, based on the solids content of the composition, that is based on all components with the exception of solvents such as water or organic solvents having a boiling point less than 150 0 C, which are removed in the later use of the composition as volatile components.
  • the minimum amount of alkanolamine is at least 0.1 wt .-%, most preferably at least 0.2 wt .-%.
  • the maximum amount is preferably 7% by weight, in particular 5% by weight. All percentages are based on the above solids content.
  • compositions preferably contain a synthetic binder, which may be a polyadduct, a polycondensate or a polymer obtainable by free-radical polymerization (polymer for short).
  • a synthetic binder which may be a polyadduct, a polycondensate or a polymer obtainable by free-radical polymerization (polymer for short).
  • compositions contain a polymer as a binder.
  • the polymer consists of at least 40 wt .-%, preferably at least 60 wt .-%, more preferably at least 80 wt .-% of so-called main monomers.
  • the main monomers are selected from C 1 -C 20 -alkyl (meth) acrylates, vinyl esters of carboxylic acids containing up to 20 carbon atoms, vinyl aromatics with up to
  • (Meth) acrylic acid alkyl esters having a Ci-Cio-alkyl radical such as methyl methacrylate, methyl acrylate, n-butyl acrylate, ethyl acrylate and 2-ethylhexyl acrylate.
  • mixtures of (meth) acrylic acid alkyl esters are also suitable.
  • Vinyl esters of carboxylic acids having 1 to 20 carbon atoms are e.g. Vinyl laurate, stearate, vinyl propionate, vinyl versatate and vinyl acetate.
  • Suitable vinylaromatic compounds are vinyltoluene, ⁇ - and p-methylstyrene, ⁇ -butylstyrene, 4-n-butylstyrene, 4-n-decylstyrene and preferably styrene.
  • nitriles are acrylonitrile and methacrylonitrile.
  • the vinyl halides are chloro, fluoro or bromo substituted ethylenically unsaturated compounds, preferably vinyl chloride and vinylidene chloride.
  • vinyl ethers there are e.g. Vinyl methyl ether or vinyl isobutyl ether. Vinyl ether is preferably from 1 to 4 C-containing alcohols.
  • hydrocarbons having 4 to 8 carbon atoms and two olefinic double bonds may be mentioned butadiene, isoprene and chloroprene.
  • Preferred main monomers are preferably the C 1 to C 10 -alkyl acrylates and methacrylates, especially C 1 to C 8 -alkyl acrylates and methacrylates and vinylaromatics, in particular styrene and mixtures thereof.
  • the polymer is at least 60 wt .-%, more preferably at least 80 wt .-% and most preferably at least 95 wt .-% of Ci to C20 alkyl (meth) acrylates, vinylaromatics or mixtures thereof.
  • Suitable binders are also used as pure acrylate binders (d-to-di-alkyl acrylates and methacrylates as main monomers and no vinyl aromatics) or as styrene / acrylate binders (C 1 to C 10 alkyl acrylates and methacrylates and vinyl aromatics, in particular styrene as main monomers ) designated.
  • the polymer may contain other monomers, e.g. Monomers with carboxylic acid, sulfonic acid or phosphonic acid groups. Preferred are carboxylic acid groups. Called e.g. Acrylic acid, methacrylic acid, itaconic acid, maleic acid or fumaric acid.
  • hydroxyl-containing monomers in particular Ci-Cio-hydroxyalkyl (meth) acrylates, (meth) acrylamide.
  • Phenyloxyethylglycol mono- (meth) acrylate, glycidyl acrylate, glycidyl methacrylate, amino (meth) acrylates such as 2-aminoethyl (meth) acrylate may also be mentioned as further monomers.
  • the polymer contains hydrophilic groups, especially those selected from carboxyl groups, hydroxyl groups, amino groups and carboxamide groups.
  • the content of these hydrophilic groups is in particular 0.001 to 0.5 mol per 100 g of polymer.
  • the content is preferably at least 0.005 mol, particularly preferably at least 0.008 mol and not more than 0.2 mol, in particular not more than 0.1 mol, very particularly preferably not more than 0.05 or 0.03 mol per 100 g / polymer.
  • hydrophilic groups selected from carboxyl groups, hydroxyl groups and carboxamide groups.
  • At least 20 mole percent of the total moles of these groups are carboxyl groups.
  • Carboxyl groups are understood as meaning both carboxylic acid groups and their salts.
  • hydrophilic groups can be bound to the polymer by copolymerization of the corresponding monomers.
  • Preferred monomers having hydrophilic groups are the abovementioned monomers having carboxyl groups and hydroxyl groups, in particular, for example, acrylic acid or methacrylic acid.
  • the choice of monomers also determines the glass transition temperature of the polymer.
  • the glass transition temperature of the resulting polymer can be determined by conventional methods such as differential thermal analysis or differential scanning calorimetry (see, for example, ASTM 3418/82, so-called "midpoint temperature").
  • the glass transition temperature is preferably -60 to 0 0 C, more preferably -60 to -1 0 0 C and most preferably -60 to 0O 0 C. If it is for use as a paint, the glass transition temperature is preferably -20 to 100 0 C is, more preferably 0 to 8O 0 C.
  • compositions according to the invention are preferably aqueous compositions.
  • the binder is dissolved or dispersed in water.
  • the binder is generally obtained by a solution polymerization
  • the binder is generally obtained by an emulsion polymerization.
  • the preparation of the above polymers is carried out in a preferred embodiment by emulsion polymerization, it is therefore an emulsion polymer.
  • ionic and / or nonionic emulsifiers and / or protective colloids or stabilizers are used as surface-active compounds.
  • the surfactant is usually used in amounts of from 0.1 to 10 parts by weight, preferably from 0.2 to 5 parts by weight, based on 100 parts by weight of the monomers to be polymerized.
  • Water-soluble initiators for emulsion polymerization are e.g. Ammonium and alkali metal salts of peroxodisulfuric acid, e.g. Sodium peroxodisulfate, hydrogen peroxide or organic peroxides, e.g. tert-butyl hydroperoxide.
  • red-ox reduction-oxidation
  • the redox initiator systems consist of at least one mostly inorganic reducing agent and one inorganic or organic oxidizing agent.
  • the polymer thus prepared is preferably used in the form of its aqueous dispersion.
  • the compositions of the invention can be used in particular as a coating composition, sealant or adhesive.
  • the coating compositions, sealants or adhesives may contain, in addition to the alkanolamine and the binder, further constituents.
  • Adhesives in particular pressure-sensitive adhesives may e.g. Fillers, colorants, leveling agents, thickeners or tackifiers (tackifying resins)
  • Tackifiers are, for example, natural resins, such as rosin resins and their derivatives resulting from disproportionation or isomerization, polymerization, dimerization, hydrogenation, which can be used in their salt form (with, for example, mono- or polyhydric Alcohols used for esterification may be monohydric or polyhydric, for example, methanol, ethanediol, diethylene glycol, triethylene glycol, 1,2,3-propanethiol, pentaerythritol.
  • Sealants may in particular contain fillers. Furthermore, they contain aids to increase the stability, e.g. Thickener to increase the viscosity.
  • coating compositions e.g. Paints, varnishes, protective coatings, plasters, printing inks.
  • paints are mentioned paints for vehicles, industrial coatings, wood coatings. Often these are crosslinking paint systems which can be crosslinked thermally or by radiation during use.
  • printing inks e.g. Printing inks, especially aqueous inks, for ink-jet, but also for offset printing, called high or low pressure.
  • pigments and / or fillers containing coating compositions into consideration. Examples include in particular printing inks, plasters and paints, both for interior and for outdoor applications. Particularly preferred are coating compositions for outdoor applications.
  • pigments in particular inorganic, particulate pigments may be mentioned.
  • White pigments such as titanium dioxide, preferably in the rutile form, barium sulfate or zinc oxide, or color pigments such as iron oxides, carbon black, luminescent pigments, zinc yellow, zinc green or ultramarine.
  • Fillers which may be mentioned in particular inorganic, particulate fillers. Suitable examples are aluminosilicates, such as feldspars, silicates, such as kaolin, talc, mica, wollastonite, magnesite, alkaline earth carbonates, such as calcium carbonate, for example in the form of calcite or chalk, magnesium carbonate, dolomite, alkaline earth sulfates, such as calcium sulfate, silicon dioxide, Plastorit®, etc.
  • the fillers can be used individually or in a mixture.
  • the coating compositions preferably contain 10 to 1000 parts by weight of pigments, fillers or mixtures of pigments and fillers per 100 parts by weight of binder. When used as (highly filled) interior paint, they particularly preferably contain from 300 to 800 parts by weight and as gloss coating 10 to 100 parts by weight of pigments, fillers or mixtures of pigments and fillers per 100 parts by weight of binder.
  • compositions which may be contained in the coating compositions are e.g. Antifreeze, leveling agent and thickener.
  • compositions of the invention can be processed by conventional methods, or be used in the usual way as an adhesive sealant or coating mass.
  • the composition is applied to the desired substrate or surface to be coated, and then the solvent is removed, e.g. by drying at ambient temperature or at elevated temperatures.
  • the above alkanolamines of the formula I are very suitable as neutralizing and / or dispersing agents in the compositions according to the invention. They have a similar base strength as AMP (other amines have lower base strength and are therefore needed in larger amounts to adjust the pH).
  • the compositions according to the invention may be completely or partially neutralized with the alkanolamine;
  • the pH of the compositions may be in particular 5 to 9.
  • the performance properties, the solvents, chemicals and in particular the water resistance of the resulting coatings, seals or bonds are very good, also in comparison to the AMP or DMAMP. A blushing is not or hardly observed in the compositions of the invention.
  • the binder dispersion was stirred in at a slower speed. With further stirring (5-10 min), the other additives and auxiliaries were finally added.
  • the pigment volume concentration (PKV) is the quotient, multiplied by 100, of the volume fraction of the pigments and fillers relative to the total volume of the pigments, fillers and binders PH value
  • the rotational viscometer used was a HAAKE Viscotester 550 (Thermo Electron (Karlsruhe) GmbH, Düsseldorf). It was measured according to DIN 53019-1 (05/80) with the measuring device SV-DIN and a speed gradient of 1 to 500 S -1 (and back) The test temperature was (23 ⁇ 0.2) ° C.
  • the gloss was determined as a reflectance value according to DIN EN ISO 2813 (06/99) under measuring angles of 60 ° and 85 °. For this, the paints with a wet film thickness of 200 ⁇ m were applied to glass plates and dried for a minimum of one week at (23 ⁇ 2) 0 C and (50 ⁇ 5)% relative humidity before the measurement. The division of the gloss takes place according to DIN EN 1062-1 (08/04):
  • the numbers are parts by weight.
  • Tego Glide 482 Lubricant Solvenon DPM: Glycol ether
  • Tinuvin 1130 UV inhibitor
  • Acronal LR 9014 an aqueous polyacrylate dispersion from BASF, solids content 45%
  • Collacral PU 75 a polyurethane thickener from BASF Latekoll DS 6269: polyacrylate thickener
  • Test equipment and test equipment Pinewood 150 x 70 x 5 mm, Erichsen film applicator
  • the glaze to be tested (300 ⁇ m wet) is applied to the pine wood board with the Erichsen film applicator. After a drying time of 7 days at RT, the test surface is prepared by means of cross-cut tester and cutter (45 ° to the wood grain, 7 cuts, 2 mm cutting distance). Subsequently, approx. 2.5 ml of deionised water are pipetted into the Petri dish and this is centered on the previously installed cutting grid for a period of 2 hours (place board on Petri dish and turn by 180 °). The Petri dish is removed and the remaining deionised water is sucked up with a cloth.
  • Luhydran S937T® polyacrylate dispersion
  • Luwipal®069 (melamine resin) 4.8
  • the Delta 60 value indicates the pH change after 60 hours.
  • Composition A 479 parts by weight Acronal S 410 479 parts by weight Acronal S 533 16 parts by weight Alkanolamine P6 21 parts by weight Aerosil 200 5 parts by weight Coatosil 1770
  • Composition B (according to the invention)

Abstract

L’invention concerne des compositions appropriées en tant que matériau de revêtement, matériau d’étanchéité ou adhésif, caractérisées en ce qu’elles contiennent une alcanolamine de formule (I), dans laquelle R1 représente un groupe alkyle en C1 à C4 et R2 représente un atome d’hydrogène ou un groupe alkyle en C1 à C4, R3 représente un atome d’hydrogène ou un groupe alkyle en C1 à C4, et R4 et R5 représentent indépendamment l’un de l’autre un groupe alkyle en C1 à C4.
PCT/EP2009/053769 2008-04-03 2009-03-31 Compositions contenant une alcanolamine WO2009121856A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08153995.9 2008-04-03
EP08153995 2008-04-03

Publications (1)

Publication Number Publication Date
WO2009121856A1 true WO2009121856A1 (fr) 2009-10-08

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PCT/EP2009/053769 WO2009121856A1 (fr) 2008-04-03 2009-03-31 Compositions contenant une alcanolamine

Country Status (1)

Country Link
WO (1) WO2009121856A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1269843A1 (fr) * 2001-06-29 2003-01-02 Creavis Gesellschaft für Technologie und Innovation mbH Mousses polymériques antimicrobielles avec des aminoalcohols
WO2003008511A1 (fr) * 2001-07-17 2003-01-30 E.I. Du Pont De Nemours And Company Suspension de dioxyde de titane de rutile non fini pour peintures et revetements papier
WO2003048233A1 (fr) * 2001-12-04 2003-06-12 Crompton Vinyl Additives Gmbh Stabilisation de dispersions de polymeres renfermant des halogenes
WO2005121237A1 (fr) * 2004-06-02 2005-12-22 Arkema Inc. Antiskinning compound and compositions containing them
WO2008088632A2 (fr) * 2007-01-12 2008-07-24 Angus Chemical Company Compositions d'un aminoalcool et d'un biocide pour systèmes à base aqueuse

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1269843A1 (fr) * 2001-06-29 2003-01-02 Creavis Gesellschaft für Technologie und Innovation mbH Mousses polymériques antimicrobielles avec des aminoalcohols
WO2003008511A1 (fr) * 2001-07-17 2003-01-30 E.I. Du Pont De Nemours And Company Suspension de dioxyde de titane de rutile non fini pour peintures et revetements papier
WO2003048233A1 (fr) * 2001-12-04 2003-06-12 Crompton Vinyl Additives Gmbh Stabilisation de dispersions de polymeres renfermant des halogenes
WO2005121237A1 (fr) * 2004-06-02 2005-12-22 Arkema Inc. Antiskinning compound and compositions containing them
WO2008088632A2 (fr) * 2007-01-12 2008-07-24 Angus Chemical Company Compositions d'un aminoalcool et d'un biocide pour systèmes à base aqueuse

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