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WO1992014763A1 - Procede de production d'un polymere aqueux emulsionne sechable par autoxydation utile de preference comme liant de laques - Google Patents

Procede de production d'un polymere aqueux emulsionne sechable par autoxydation utile de preference comme liant de laques Download PDF

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Publication number
WO1992014763A1
WO1992014763A1 PCT/DE1992/000107 DE9200107W WO9214763A1 WO 1992014763 A1 WO1992014763 A1 WO 1992014763A1 DE 9200107 W DE9200107 W DE 9200107W WO 9214763 A1 WO9214763 A1 WO 9214763A1
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WO
WIPO (PCT)
Prior art keywords
acid
polymer
solution polymer
solution
mass
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.)
Ceased
Application number
PCT/DE1992/000107
Other languages
German (de)
English (en)
Inventor
Karl-Heinz Weinert
Siegfried Müller
Hans-Joachim Lorkowski
Doris Zekai
Klaus Tauer
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.)
Lankwitzer Lackfabrik & Co KG GmbH
Original Assignee
Lankwitzer Lackfabrik & Co KG GmbH
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 Lankwitzer Lackfabrik & Co KG GmbH filed Critical Lankwitzer Lackfabrik & Co KG GmbH
Publication of WO1992014763A1 publication Critical patent/WO1992014763A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/02—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of acids, salts or anhydrides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
    • C08F267/02—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00 on to polymers of acids or salts

Definitions

  • the invention relates to a process for producing an aqueous, autoxidatively drying emulsion polymer, preferably as a binder for lacquers, in which "a solution polymer containing carboxyl groups is first prepared by polymerizing an addition product from unsaturated fatty acids and unsaturated monomers, and then an emulsion polymerization of unsaturated monomers is carried out together with this solution polymer.
  • binder dispersions disclosed in US Pat. No. 4,122,052 show poor results in terms of gloss and toughness. Furthermore, these polymers contain too much organic solvents. as well as ammonia or amine, so that when used as a coating material they still represent strong environmental hazards.
  • the emulsifier is a maleic acid adduct of an alkyd resin. Disadvantages of such systems are the deepening of the color of the products caused by the formation of maleic acid adduct and the inadequate compatibility between the emulsifier and the polymer formed with the vinyl monomers.
  • the object of the invention is to carry out the process mentioned at the outset in such a way that better products are obtained in comparison with the known solutions.
  • This object is achieved by a process for producing an aqueous, autoxidatively drying emulsion polymer
  • an unsaturated carboxylic acid selected from the group consisting of acrylic acid, methacrylic acid, crotonic acid, fumaric acid, itaconic acid and maleic anhydride, alone or in combination, where
  • the solution polymer has an acid number between 20 and 160 and a number average molecular weight M ,, of 1,500 to 80,000 and the unsaturated fatty acid (s) form 15-60% by mass of the solution polymer,
  • the solution polymer fulfills two functions:
  • the two functions of the solution polymer are influenced by the degree of neutralization of the carboxyl groups:
  • the solubility of the solution polymer is reduced, so that it can only act insufficiently as a dispersion stabilizer. If the degree of neutralization is too high, the solubility increases such that not only is the dynamic equilibrium of the distribution of the solution polymer between the interior of the solution and the phase boundary regions monomer / water or polymer / water shifted in favor of the interior of the solution, but also at the same time due to the increased degree of dissociation of the carboxyl group, the polymer molecules expand. The latter behavior can even increase the viscosity to such an extent that conventional emulsion polymerization is prevented or unsuitable cream-like products are formed.
  • the dispersed polymer particles surprisingly have a core-shell morphology, the unsaturated fatty acids introduced via the solution polymer being enriched in the shell region.
  • the polymer particles penetrate and bond mainly with their shell areas. These determine the properties of the overall film.
  • This morphology requires a degree of neutralization that is neither 0 nor 1. With one between these Accordingly, the two degrees of neutralization have particularly good properties.
  • the lacquers which are produced according to the teaching according to the invention are more weather-resistant, storage-stable, light-resistant, shear-stable, glossy and harder than the lacquers which are produced by the known processes.
  • the binders according to the invention contain less amines or ammonia.
  • the binders according to the invention are notable for high water, in particular salt water and solvent resistance.
  • the conversion to the addition product from unsaturated fatty acids and unsaturated monomers, preferably glycidyl methacrylate, is usually carried out at a temperature of 120 to 190 ° C., preferably at a temperature of 150 ° C., and with the catalyst tetraethylammonium bromide in a time of 1 to 6 hours, preferably 2 hours.
  • the acid number of the mixture drops below 3% of the initial value after the reaction.
  • the solution polymer is preferably synthesized by free-radical polymerization of the addition product with unsaturated carboxylic acids, preferably with methacrylic acid in cyclohexanone or butoxyethanol at 90 ° to 150 ° C., preferably at 120 ° C. in butoxyethanol, with the aid of azo initiators.
  • the content of carboxylic acid must not be too high, but also not too low. A minimum value must be reached in order for the solution polymer to be sufficiently water-soluble, and a maximum value must not be exceeded so that the finished coating remains sufficiently hydrophobic.
  • the proportion of methacrylic acid in the solution polymer is preferably 20% by mass.
  • the emulsion polymerization is carried out at temperatures from 60 ° to 80 ° C., preferably 70 ° C.
  • the monomers are reacted under nitrogen without first removing any inhibitor that may be present.
  • Ammonium peroxodisulfate is preferably used as the water-soluble radical initiator.
  • the use of an external emulsifier can be dispensed with, since its function is essentially carried out by the solution polymer.
  • the anionic emulsifier sodium alkyl sulfate is preferably used.
  • external emulsifiers are those which are incorporated in the course of the emulsion polymerization.
  • Monosodium sulfopropyl monododecyl maleate is preferably used.
  • tetraethylammonium bromide 0.25 g are dissolved in 131.5 g of glycidyl methacrylate (GMA), which contains 0.005% by mass of hydroquinone monoethyl ether, and then mixed with 250 g of soybean oil fatty acid. The mixture is melted under nitrogen in an ampoule and heated in an oil bath at 155 ° C. for 90 minutes. The conversion of the carboxyl groups is checked by gas chromatography by determining the acid number or that of the GMA. The monomer (1.1) obtained has an acid number below 3% of the initial value.
  • GMA glycidyl methacrylate
  • the product (1.3) is mixed with 4.4 g of sodium dodecyl sulfate, 68 g of methyl methacrylate and 250 g of n-butyl methacrylate, and an emulsion is prepared under vigorous stirring under nitrogen. After heating to 70 ° C., 0.86 g of ammonium peroxodisulfate, dissolved in 20 ml of water, are added to the emulsion and the reaction is ended after 7 hours.
  • the polymer particles have an average size of 220 nm.
  • Example 2 The polymer dispersions are prepared analogously to that of Example 1, except that instead of the 52.2 g of methacrylic acid in stage 1.2, 80.7 g of methacrylic acid and Example 3 67.5 g of acrylic acid are used in Example 2. Because of the increase in the acid content, the proportion of ammonia solution is increased from 9.3 to 13.4 ml in the neutralization stage.
  • the particle sizes reach an average value of 70 nm, in example 3 this is 280 nm.
  • the polymer dispersion is prepared analogously to that of Example 2, only 68 g of styrene are used instead of 68 g of methyl methacrylate in stage 1.4.
  • the particle sizes have an average value of 230 nm.
  • the polymer dispersion is prepared analogously to that of Example 4, except that 67.5 g of acrylic acid are used instead of methacrylic acid in stage 1.2 and 13.4 ml of ammonia solution in stage 1.3.
  • the particle sizes have an average value of 310 nm.
  • the polymer dispersion is prepared analogously to that of Example 2, except that the emulsifier instead of the 4.4 g Na dodecyl sulfate used the same amount of monosodium sulfopropyl monododecyl maleate.
  • the particle sizes have an average value of 85 nm.
  • emulsion polymers according to the invention can also be used in other cases and not only for lacquers, for example for floor care products.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Selon un procédé de production d'un polymère aqueux émulsionné séchable par autoxydation et utile de préférence comme liant pour laques, on produit premièrement un polymère en solution contenant des groupes carboxyle par polymérisation d'un produit d'addition d'acides gras insaturés et de monomères insaturés avec une autre substance, puis on polymèrise une émulsion de monomères insaturés avec ce polymère en solution. Selon l'invention, le polymère en solution est neutralisé avant la polymérisation de l'émulsion par adjonction d'une base, notamment d'amines ou d'ammoniac, en particulier d'ammoniac liquide, jusqu'à un degré de neutralisation compris entre 0,4 et 0,9, notamment égal à 0,7. Les revêtements produits avec une telle laque se caractérisent par des propriétés remarquables.
PCT/DE1992/000107 1991-02-15 1992-02-13 Procede de production d'un polymere aqueux emulsionne sechable par autoxydation utile de preference comme liant de laques Ceased WO1992014763A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4105134.3 1991-02-15
DE19914105134 DE4105134C1 (fr) 1991-02-15 1991-02-15

Publications (1)

Publication Number Publication Date
WO1992014763A1 true WO1992014763A1 (fr) 1992-09-03

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Application Number Title Priority Date Filing Date
PCT/DE1992/000107 Ceased WO1992014763A1 (fr) 1991-02-15 1992-02-13 Procede de production d'un polymere aqueux emulsionne sechable par autoxydation utile de preference comme liant de laques

Country Status (2)

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DE (1) DE4105134C1 (fr)
WO (1) WO1992014763A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0643080A3 (fr) * 1993-09-10 1995-06-28 Hoechst Ag Mélanges de polymères et de l'eau.
WO1997031044A1 (fr) * 1996-02-22 1997-08-28 The Dexter Corporation Polymere dispersible dans l'eau et composition de revetement contenant un tel polymere
WO2012028627A1 (fr) * 2010-09-01 2012-03-08 Basf Se Polymères en émulsion aqueuse, leur fabrication et leur utilisation
US8722756B2 (en) 2010-09-01 2014-05-13 Basf Se Aqueous emulsion polymers, their preparation and use
EP3088432A1 (fr) 2015-04-27 2016-11-02 ALLNEX AUSTRIA GmbH Dispersions aqueuses
WO2023057249A1 (fr) 2021-10-04 2023-04-13 Basf Se Utilisation de compositions polymères aqueuses en tant que teintures pour matériaux poreux

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1009254C2 (nl) * 1998-05-25 1999-11-26 Univ Eindhoven Tech Poederverf.
DE10015913A1 (de) * 1999-04-16 2000-10-19 Henkel Kgaa Fettchemische Addukte als Tackifier und Bindemittel
US7235603B2 (en) * 2003-04-07 2007-06-26 Rohm And Haas Company Ambient curable polymer
DE102007048192A1 (de) 2007-10-08 2009-04-09 Evonik Röhm Gmbh Emulsionspolymere, wässrige Dispersionen und Verfahren zu deren Herstellung
DE102007048189A1 (de) 2007-10-08 2009-04-09 Evonik Röhm Gmbh Wässrige Dispersionen aufweisend mindestens ein Alkyd-Harz und mindestens ein Polymerisat mit mindestens einem (Meth)acrylat-Segment
DE102008002254A1 (de) 2008-06-06 2010-01-21 Evonik Röhm Gmbh Monomermischungen, Polymere sowie Beschichtungszusammensetzungen
DE102008002257A1 (de) 2008-06-06 2010-01-28 Evonik Röhm Gmbh Wässrige Dispersionen aufweisend mindestens ein Alkyd-Harz
DE102009001217A1 (de) 2009-02-27 2010-09-02 Evonik Röhm Gmbh Monomermischungen, Polymere sowie Beschichtungszusammensetzungen
DE102008046075A1 (de) 2008-09-08 2010-03-11 Evonik Röhm Gmbh (Meth)acrylatmonomer, Polymer sowie Beschichtungsmittel
DE102009001966A1 (de) 2009-03-30 2010-10-07 Evonik Röhm Gmbh Beschichtungszusammensetzung,(Meth)acryl-Polymer und Monomermischung zur Herstellung des(Meth)acryl-Polymers
DE102009001964A1 (de) 2009-03-30 2010-10-07 Evonik Röhm Gmbh Multifunktionales(Meth)acryl-Polymer, Beschichtungszusammensetzung, Verfahren zur Herstellung einer Beschichtung und beschichteter Gegenstand
DE102009001965A1 (de) 2009-03-30 2010-10-07 Evonik Röhm Gmbh Beschichtungsmittel, Verfahren zur Herstellung einer Beschichtung und beschichteter Gegenstand
DE102009001970A1 (de) 2009-03-30 2010-10-14 Evonik Röhm Gmbh (Meth)acrylat-Polymer, Beschichtungsmittel, Verfahren zur Herstellung einer Beschichtung und beschichteter Gegenstand
DE102009002888A1 (de) 2009-05-07 2010-11-11 Evonik Röhm Gmbh Beschichtungsmittel, Verfahren zur Herstellung einer Beschichtung und beschichteter Gegenstand
DE102010029930A1 (de) 2010-06-10 2011-12-15 Evonik Röhm Gmbh Verfahren zur Herstellung von Acetoacetoxyalkyl(meth)acrylat
DE102010030970A1 (de) 2010-07-06 2012-01-12 Evonik Röhm Gmbh Zusammensetzung zur Herstellung von Polymeren, (Meth)acryl-Polymer, Beschichtungsmittel und Beschichtung
DE102010041272A1 (de) 2010-09-23 2012-03-29 Evonik Röhm Gmbh Beschichtungsmittel mit (Meth)acryl-Polymeren und Koaleszenzhilfsmitteln
DE102011088149A1 (de) 2011-12-09 2013-06-13 Evonik Industries Ag Beschichteter Verbundkörper, umfassend ein Verbundmaterial
DE102013223876A1 (de) 2013-11-22 2015-05-28 Evonik Industries Ag Emulsionspolymere, wässrige Dispersionen und Verfahren zu deren Herstellung

Citations (4)

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Publication number Priority date Publication date Assignee Title
FR2265833A1 (fr) * 1974-03-28 1975-10-24 Kansai Paint Co Ltd
JPS52102390A (en) * 1976-02-25 1977-08-27 Kansai Paint Co Ltd Preparation of colloidal emulsions
US4122052A (en) * 1976-03-09 1978-10-24 Kansai Paint Company, Limited Emulsion composition
EP0305795A2 (fr) * 1987-09-03 1989-03-08 Vianova Kunstharz Aktiengesellschaft Procédé de préparation d'émulsion aqueuse de copolymères greffés et l'utilisation d'émulsion comme liant pour les revêtements séchant à l'air

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2265833A1 (fr) * 1974-03-28 1975-10-24 Kansai Paint Co Ltd
JPS52102390A (en) * 1976-02-25 1977-08-27 Kansai Paint Co Ltd Preparation of colloidal emulsions
US4122052A (en) * 1976-03-09 1978-10-24 Kansai Paint Company, Limited Emulsion composition
EP0305795A2 (fr) * 1987-09-03 1989-03-08 Vianova Kunstharz Aktiengesellschaft Procédé de préparation d'émulsion aqueuse de copolymères greffés et l'utilisation d'émulsion comme liant pour les revêtements séchant à l'air

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Title
WORLD PATENTS INDEX LATEST, Woche 7740, Derwent Publications Ltd. , Londen, GB; AN-77-71802Y, & JP, A, 52102390 (KANSAI PAINT K.K.) 27. August 1977, siehe Zusammenfassung (in der Anmeldung erwähnt) *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0643080A3 (fr) * 1993-09-10 1995-06-28 Hoechst Ag Mélanges de polymères et de l'eau.
US5521267A (en) * 1993-09-10 1996-05-28 Hoechst Aktiengesellschaft Mixtures of polymers with water
WO1997031044A1 (fr) * 1996-02-22 1997-08-28 The Dexter Corporation Polymere dispersible dans l'eau et composition de revetement contenant un tel polymere
US5830952A (en) * 1996-02-22 1998-11-03 The Dexter Corporation Water-dispersible polymer and coating composition containing the same
US5869552A (en) * 1996-02-22 1999-02-09 The Dexter Corporation Water-dispersible polymer and coating composition containing the same
US5922817A (en) * 1996-02-22 1999-07-13 The Dexter Corporation Water-dispersible polymer and coating composition containing the same
AU715870B2 (en) * 1996-02-22 2000-02-10 Dexter Corporation, The Water-dispersible polymer and coating composition containing the same
WO2012028627A1 (fr) * 2010-09-01 2012-03-08 Basf Se Polymères en émulsion aqueuse, leur fabrication et leur utilisation
US8722756B2 (en) 2010-09-01 2014-05-13 Basf Se Aqueous emulsion polymers, their preparation and use
US9150732B2 (en) 2010-09-01 2015-10-06 Basf Se Aqueous emulsion polymers, their preparation and use
EP3088432A1 (fr) 2015-04-27 2016-11-02 ALLNEX AUSTRIA GmbH Dispersions aqueuses
WO2016173821A1 (fr) 2015-04-27 2016-11-03 Allnex Austria Gmbh Dispersions aqueuses
CN107428889A (zh) * 2015-04-27 2017-12-01 湛新奥地利有限公司 含水分散体
KR20170141201A (ko) * 2015-04-27 2017-12-22 알넥스 오스트리아 게엠베하 수성 분산물
US20180086936A1 (en) * 2015-04-27 2018-03-29 Allnex Austria Gmbh Aqueous dispersions
JP2018521145A (ja) * 2015-04-27 2018-08-02 オールネックス オーストリア ゲーエムベーハー 水性分散体
US10494541B2 (en) 2015-04-27 2019-12-03 Allnex Austria Gmbh Aqueous dispersions
AU2016254105B2 (en) * 2015-04-27 2020-01-23 Allnex Austria Gmbh Aqueous dispersions
TWI685551B (zh) * 2015-04-27 2020-02-21 奧地利商湛新奧地利有限公司 水性分散液、其製備方法、摻合物及製備塗布的基材或物件之方法
KR102382413B1 (ko) 2015-04-27 2022-04-01 알넥스 오스트리아 게엠베하 수성 분산물
WO2023057249A1 (fr) 2021-10-04 2023-04-13 Basf Se Utilisation de compositions polymères aqueuses en tant que teintures pour matériaux poreux

Also Published As

Publication number Publication date
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