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WO2013012365A1 - Dispersion d'homopolymère ou de copolymère à l'eau - Google Patents

Dispersion d'homopolymère ou de copolymère à l'eau Download PDF

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Publication number
WO2013012365A1
WO2013012365A1 PCT/SE2012/000100 SE2012000100W WO2013012365A1 WO 2013012365 A1 WO2013012365 A1 WO 2013012365A1 SE 2012000100 W SE2012000100 W SE 2012000100W WO 2013012365 A1 WO2013012365 A1 WO 2013012365A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer dispersion
dispersion according
crotonate
isocrotonate
waterborne polymer
Prior art date
Application number
PCT/SE2012/000100
Other languages
English (en)
Inventor
Håkan BJÖRNBERG
Bo HÅGGMAN
Eric Appelman
Original Assignee
Perstorp Ab
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 Perstorp Ab filed Critical Perstorp Ab
Publication of WO2013012365A1 publication Critical patent/WO2013012365A1/fr

Links

Classifications

    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/12—Polymerisation in non-solvents
    • C08F2/16—Aqueous medium
    • C08F2/22—Emulsion polymerisation
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate

Definitions

  • the present invention refers to a waterborne homo or copolymer dispersion obtained by homo or copolymerisation in an aqueous medium of at least one alkyl crotonate and/or at least one crotonic acid.
  • Emulsion polymerisation is well known in the art and frequently disclosed and discussed in the patent literature, in handbooks and encyclopaedias. Emulsion polymerisation is typically performed in an aqueous medium in the presence of a surfactant and a water-soluble initiator and is usually rapidly giving high molecular weight homo or copolymers at high solids content, typically 30-60%, and low dispersion viscosity.
  • a surfactant typically a surfactant and a water-soluble initiator
  • Traditional applications for these aqueous dispersions are mainly adhesives, binders for fibres, protective and decorative coatings, foam, paper coatings and thread and textile modifiers.
  • the present invention accordingly refers to a novel waterborne homo or preferably copolymer dispersion obtained by homo or preferably copolymerisation in an aqueous medium of at least one alkyl crotonate or isocrotonate, preferably a Ci-Cis alkyl crotonate or isocrotonate, such as methyl crotonate, ethyl crotonate, n-butyl crotonate, isobutyl crotonate, t-butyl crotonate, 2-ethylhexyl crotonate, 2-propylheptyl crotonate, neopentyl crotonate, glycidyl crotonate, vinyl
  • alkyl crotonates include alkyl dicrotonates and alkyl diisocrotonates of diols, such as ethylene glycol, 1 ,2-propanediol, 1,3-propanediol, butylene glycols, and 2-alkyl-l ,3-propanediols, 2,2-dialkyl-l,3-propanediols, such as neopentyl glycol and 2-ethyl-2-butyl- 1 ,3-propanediol.
  • diols such as ethylene glycol, 1 ,2-propanediol, 1,3-propanediol, butylene glycols, and 2-alkyl-l ,3-propanediols, 2,2-dialkyl-l,3-propanediols, such as neopentyl glycol and 2-ethyl-2-butyl- 1 ,
  • mono(iso)crotonates of diols mono, di and tri(iso)crotonates of triols and mono di, tri and higher (iso)crotonates of polyols can be included, such as trimethylolpropane mono, di or tricrotonate or isocrotonate.
  • alkyl acrylates and/or alkyl methacrylates preferably Ci-C 18 alkyl acrylates or methacrylates, such as methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, and/or acrylic acid and/or methacrylic acid, and/or polymerisable allyl, vinyl, maleic and/or diene monomers, such as, but not limited to, itaconic acid, cinnamic acid, maleic anhydride, fumaric acid, glycidyl acrylates, glycidyl methacrylates, acrylamides, methacrylamides, ethyl imidazolidon methacrylates, ethylene, propylene, styrene, divinylstyrene, vinylacetate, vinyl propionates, vinyl versatates, dibutyl
  • the homo or copolymer dispersion of the present invention is yielded in either a one stage or a multistage emulsion homo or copolymerisation.
  • Said emulsion polymerisation may for instance yield latex particles having a heterogeneous morphology, such as a core-shell morphology.
  • core-shell morphologies are possible.
  • spherical core-shell particles are made when a polymer made from a first monomer is more hydrophobic than a polymer made from a second monomer.
  • dispersion according to the present invention include species comprising at least one polymerisable surfactant, such as a surfactant comprising at least one alkenyl group, and/or a conventional surfactant.
  • a polymerisable surfactant such as a surfactant comprising at least one alkenyl group, and/or a conventional surfactant.
  • a copolymer according to the present invention is such that the crotonate based content of the total content, with water and/or other solvents excluded, is 0.1-99.9%, such as 5-60%, 5-30% or 10-25%), by weight.
  • Storage stability, glass transition temperature and particle size distribution are important parameters whose optima are to be found within the monomer content levels given above.
  • crotonic acid and crotonic acid derivatives can be used together with mercaptans in the so called thiol-ene reaction to produce a crosslinked system.
  • Thiol-enes can be part of hybrid systems that involve both thiol-enes and other types of systems, such as radical polymerised unsaturations. By this, the property range of the coatings can be expanded.
  • Thiol-ene networks due to their almost perfect network structure that is much more uniform than even epoxy networks, can be fabricated to exhibit a wide range of benchmark properties including rubber-like materials with resiliencies of greater than 95%o, glassy materials with properties resembling traditional rubbery materials (i.e.
  • cellulose can be modified, preferably covalently bonded, with crotonic acid and crotonic acid derivatives to obtain increased stability and/or a crosslinked structure.
  • the present invention refers to the use of said novel waterborne homo or copolymer dispersion, as disclosed above, in binders for coatings, such as decorative and/or protective paints and lacquers, adhesives and glues.
  • binders for coatings such as decorative and/or protective paints and lacquers, adhesives and glues.
  • Initiator solution 25% by weight of ammonium persulphate in water, room temperature.
  • Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
  • Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate, butyl acrylate and acrylic acid.
  • Ammonium persulphate 2 Yielded product exibited following properties:
  • Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
  • Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid. Material Parts by weig

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention porte sur une dispersion de polymère à l'eau obtenue par homopolymérisation ou de préférence copolymérisation, conjointement avec un ou plusieurs autres monomères polymérisables, dans un milieu aqueux d'au moins un crotonate d'alkyle, isocrotonate d'alkyle, acide crotonique et/ou acide isocrotonique.
PCT/SE2012/000100 2011-07-19 2012-06-29 Dispersion d'homopolymère ou de copolymère à l'eau WO2013012365A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161509304P 2011-07-19 2011-07-19
US61/509,304 2011-07-19

Publications (1)

Publication Number Publication Date
WO2013012365A1 true WO2013012365A1 (fr) 2013-01-24

Family

ID=47558348

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE2012/000100 WO2013012365A1 (fr) 2011-07-19 2012-06-29 Dispersion d'homopolymère ou de copolymère à l'eau

Country Status (1)

Country Link
WO (1) WO2013012365A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104387515A (zh) * 2014-11-13 2015-03-04 常熟市万象涂料有限公司 一种界面剂及其制备方法
CN105085777A (zh) * 2015-07-17 2015-11-25 中国石油天然气股份有限公司 一种聚苯乙烯2-丁烯酸乙酯及其制备方法与应用
CN109868094A (zh) * 2019-01-24 2019-06-11 东莞泰康聚合物科技有限公司 一种代替乙烯-醋酸乙烯酯乳液的新型防水乳液及制备方法

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB903675A (en) * 1959-09-11 1962-08-15 Leicester Lovell & Co Ltd Improvements in or relating to the temporary protection of surfaces
JPH04332779A (ja) * 1991-05-08 1992-11-19 Toagosei Chem Ind Co Ltd 水性樹脂分散体
WO1997026303A1 (fr) * 1996-01-18 1997-07-24 Akzo Nobel Industrial Coatings Ab Composition hybride aqueuse de liant et son utilisation
US5969030A (en) * 1995-07-24 1999-10-19 Basf Corporation Waterborne coating compositions containing hydrophobically modified emulsions
EP1044991A1 (fr) * 1999-04-13 2000-10-18 Rohm And Haas Company Procédé de préparation de compositions durcissables et compositions ainsi obtenues
EP1197502A2 (fr) * 2000-10-11 2002-04-17 Dainippon Ink And Chemicals, Inc. Emulsion aqueuse de résine et revêtement à base aqueuse
WO2004016701A1 (fr) * 2002-08-16 2004-02-26 Perstorp Specialty Chemicals Ab Dispersion d'homopolymere ou de copolymere hydrophile
US20050004272A1 (en) * 2003-06-23 2005-01-06 Thauming Kuo Small-particle latex compositions based on waterborne alkyd seeds
WO2005003186A1 (fr) * 2003-07-01 2005-01-13 Celanese Emulsions Norden Ab Procede de production d'une dispersion aqueuse de copolymere
WO2011056384A1 (fr) * 2009-11-06 2011-05-12 Columbia Insurance Company Compositions colorantes et peintures/revêtements au latex respectueux de l'environnement

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB903675A (en) * 1959-09-11 1962-08-15 Leicester Lovell & Co Ltd Improvements in or relating to the temporary protection of surfaces
JPH04332779A (ja) * 1991-05-08 1992-11-19 Toagosei Chem Ind Co Ltd 水性樹脂分散体
US5969030A (en) * 1995-07-24 1999-10-19 Basf Corporation Waterborne coating compositions containing hydrophobically modified emulsions
WO1997026303A1 (fr) * 1996-01-18 1997-07-24 Akzo Nobel Industrial Coatings Ab Composition hybride aqueuse de liant et son utilisation
EP1044991A1 (fr) * 1999-04-13 2000-10-18 Rohm And Haas Company Procédé de préparation de compositions durcissables et compositions ainsi obtenues
EP1197502A2 (fr) * 2000-10-11 2002-04-17 Dainippon Ink And Chemicals, Inc. Emulsion aqueuse de résine et revêtement à base aqueuse
WO2004016701A1 (fr) * 2002-08-16 2004-02-26 Perstorp Specialty Chemicals Ab Dispersion d'homopolymere ou de copolymere hydrophile
US20050004272A1 (en) * 2003-06-23 2005-01-06 Thauming Kuo Small-particle latex compositions based on waterborne alkyd seeds
WO2005003186A1 (fr) * 2003-07-01 2005-01-13 Celanese Emulsions Norden Ab Procede de production d'une dispersion aqueuse de copolymere
WO2011056384A1 (fr) * 2009-11-06 2011-05-12 Columbia Insurance Company Compositions colorantes et peintures/revêtements au latex respectueux de l'environnement

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104387515A (zh) * 2014-11-13 2015-03-04 常熟市万象涂料有限公司 一种界面剂及其制备方法
CN105085777A (zh) * 2015-07-17 2015-11-25 中国石油天然气股份有限公司 一种聚苯乙烯2-丁烯酸乙酯及其制备方法与应用
CN109868094A (zh) * 2019-01-24 2019-06-11 东莞泰康聚合物科技有限公司 一种代替乙烯-醋酸乙烯酯乳液的新型防水乳液及制备方法

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