WO1991006586A1 - Resine soluble dans l'eau - Google Patents

Resine soluble dans l'eau Download PDF

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Publication number
WO1991006586A1
WO1991006586A1 PCT/NL1990/000163 NL9000163W WO9106586A1 WO 1991006586 A1 WO1991006586 A1 WO 1991006586A1 NL 9000163 W NL9000163 W NL 9000163W WO 9106586 A1 WO9106586 A1 WO 9106586A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
molar ratio
claimε
process according
water
Prior art date
Application number
PCT/NL1990/000163
Other languages
English (en)
Inventor
Adriaan Hofland
Dick Adriaan Pons
Original Assignee
Stamicarbon B.V.
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 Stamicarbon B.V. filed Critical Stamicarbon B.V.
Publication of WO1991006586A1 publication Critical patent/WO1991006586A1/fr
Priority to FI921927A priority Critical patent/FI921927A/fi
Priority to NO92921698A priority patent/NO921698L/no

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
    • 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
    • C08F220/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C08F220/68—Esters

Definitions

  • the invention relates to water-soluble resins that can be used as dispersants.
  • Water-soluble resins that can be used as dispersants are described in, for instance, 'Paint Flow and Pigment Dispersion' by T.C. Patton, pp 290-296 (1979).
  • Dispersants known in the art such as, for instance, ' polyphosphates, isobutylene maleic acid copolymer-sodium salt and polyacrylate ⁇ , cannot be sufficiently mixed with binders such as, for instance, alkyd resin dispersions, to obtain paints with good gloss properties. It is possible also, for instance ⁇ to use water-dilutable alkyd resins as dispersants for pigments.
  • the known resins u&ed as dispersants will, moreover, have to be combined with undesired compounds such as, for instance, amines or organic solvents.
  • the object of the invention is to provide a properly processable, air-drying and water-soluble resin suited as dispersant and resulting in paints with a good gloss.
  • A polyethylene glycol with (5-100) ethylene oxide units
  • B a compound containing one or more allyl and/or (meth)acrylate groups
  • C the reaction product of one or more unsaturated fatty acids or one or more polyalcohol(s) wholly or partly esterified with unsaturated fatty acids with an compound, where the A:C molar ratio is between 0.5:1 and 4:1 and the B:C molar ratio is between 0.5:1 and 4:1.
  • the A:B molar ratio is mostly between 4:1 and 1:4 and is preferably substantially 1:1.
  • This resin moreover, need not be combined with compounds such as, for instance, amines or organic solvents. Here it consequently also concerns solvent-free systems.
  • Another advantage of the use of the resin as dispersant is that in the preparation of the paint there is hardly any foaming of the dispersant, so that hardly any or no anti-foaming agents need be added.
  • the A:C molar ratio is between 0.8:1 and 2:1 and the B:C molar ratio between 0.8:1 and 2:1.
  • the polyethylene glycol has (8-20) ethylene oxide units.
  • the polyethylene glycol has (10-14) ethylene oxide units.
  • the chosen number of ethylene oxide units is such that the resin continues to be water-soluble.
  • the resin according to the invention can very well be used as a dispersant if it has the following characteristics: a number-average molecular weight M of between 1000 and 3000; a weight-average molecular weight M of between 2000 and
  • 6000 a polydispersity M /'M of between 1.5 and 3.5; a viscosity of between 10 and 100 dPas, preferably between 10 and 30 dPas; - an iodine value of between 50 and 150 g iodine/100 grammes resin.
  • the molecular weights have been determined via GPC (Ultra-styragel, Waters, 100A, lOOOA, 10,000A separating capacity M W 200- 300,000).
  • the viscosity has been determined at 23°C using a rotational viscosimeter (DIN 53019, Bohlin).
  • the iodine value has been determined via ASTM D 1959-85.
  • the polydispersity of the resin is between 1.5 and 3.5 hardly any preferential adsorption of high-molecular weight product takes place, so that no low-molecular weight product is left behind in the aqueous phase.
  • compound B may be used compounds containing allyl groups such as, for instance, allyl ethers with 3-20 carbon atoms, allyl alcohol, allylglycidyl ethers, diallyl ethers of glycerol, diallyl ether of trimethylolpropane or diallyl ethers of trimethylolethane and triallyl ether of pentaerythritol, as well as compounds containing acrylate groups such as, for instance, hydroxyethyl(meth)acrylate, hydroxylpropyl(meth)acrylate and hydroxybutyl(meth)acrylate.
  • the compound used as B is preferably a compound containing allyl groups, such as allyl alcohol.
  • polyalcohols wholly or partly esterified with unsaturated fatty acids are linseed oil, soybean oil, safflower oil, oiticica oil, caraway oil, rapeseed oil, wood oil and fish oil. Further can be used diesters and triesters of polyalcohols, such as glycerol, trimethylolpropane or pentaerythritol, and as unsaturated fatty acids the fatty acids of the above-mentioned unsaturated oils and tall oil fatty acid.
  • Suitable unsaturated carbonyl compounds are maleic anhydride, fumaric acid or a functional (with, in addition to the unsaturation, another reactive group not being an unsaturation) acrylate.
  • C is the reaction product of linseed oil and/or safflower oil with maleic anhydride.
  • the invention also comprises a process for the preparation of the present resin on the basis of A, B and C.
  • an unsaturated compound preferably maleic anhydride
  • an unsaturated vegetable oil such as linseed oil or safflower oil
  • alcohol-anhydride reactions can be carried out. These reactions usually take place in the presence of an appropriate catalyst such as, for instance, triethyl amine at temperatures lower than 150°C.
  • the A:B molar ratio is mostly between 4:1 and 1:4 and is preferably substantially 1:1.
  • the A:C molar ratio is preferably between 0.5:1 and 4:1 and the B:C molar ratio preferably between 0.5:1 and 4:1. According to a further preferred embodiment of the invention the said ratios are between 0.8:1 and 2:1.
  • A:B:C molar ratio is substantially 1:1:1.
  • the invention also comprises a modified resin obtained in that the resin described above, built up from A, B and C at temperatures lower than 150°C, is modified with one or more monofunctional epoxy compounds, preferably with a terminal copolymerizable double bond, such as for instance glycidyl(meth)-acrylate or glycidylallyl ether.
  • the catalysts may be, for instance, triethyl amine or N,N-dimethylaniline.
  • the molar ratio of the reactants is preferably substantially 1:1. This modification is preferably applied if the resin has free acid groups, because the epoxy compounds can then react with the acid groups present.
  • This modified reaction product can subsequently react with acids or anhydrides such as, for instance, maleic acid(anhydride) .
  • the resin according to the invention can be used as dispersant or grinding agent and/or wetting agent for pigments.
  • a suitable pigment paste contains, for instance, 50-70% (wt) pigment, 3-7% (wt) resin according to the invention and 20-45% (wt) water.
  • the dispersant can be used in water-based air-drying paint systems. In order to reach any desired pigment-volume concentration (PVC), alkyd dispersions, acrylate dispersions or mixtures of these can be added to the medium also.
  • PVC pigment-volume concentration
  • alkyd dispersions, acrylate dispersions or mixtures of these can be added to the medium also.
  • the effect of using the resin according to the invention as air-drying water-soluble dispersant is that the solubility and compatibility with, for instance, alkyd emulsions is substantially improved, so that good glossy systems are obtained.
  • the resin according to the invention can be used also as water-soluble air-drying binder, or as water-soluble wood preservative in the form of copper or zinc salts of the resin.
  • the resin according to the invention can further be used as air-drying plasticizer in, for instance, acrylate dispersions.
  • Traditional plasticizers for acrylate dispersions are, for instance, (ethers of) ethylene and propylene glycols. These compounds, however, evaporate during the drying of the film, which is undesirable for, inter alia, environmental reasons.
  • the resin according to the invention does not have this disadvantage.
  • Another use of the resin is its use as drying emulsifier for the preparation of alkyd emulsions, and in acrylate dispersions.
  • the resin according to the invention can be mixed with the customary additives for obtaining paint compositions.
  • these additives are pigments, colourants, fillers, thickeners, flow-promoting agents, thixotropic agents, flatting agents, stabilizers and/or siccatives.
  • the invention is elucidated by means of the following non-restrictive examples.
  • a pigment paste based on a dispersant, titanium dioxide, thickener and demin water was prepared at 3000 rpm for 30 minutes according to Table I below. Subsequently, to 1 part by weight of this paste 2 parts by weight alkyd emulsion were added. Finally, sicactivtion took place using a cobalt (I ⁇ )-acetate solution.
  • Pigment-volume concentration % 20 20 Solids content, % 60 60 Viscosity 23°C,
  • Orotan 731 SD dispersant, isobutylenemaleic acid copolymer- ⁇ odium salt
  • Example II was repeated, the amounts by weight being altered as indicated in Table II.
  • Serad FX1010 polyurethane-based thickener Agitan 295: anti-foaming agent Serad FX508: pigment wetting agent Serad FA607: pigment wetting agent -10-
  • Orotan 731 dispersant, isobutylmaleic acid copolymer-sodium salt
  • a paint composition based on the resin according to the invention resulted in a good glo ⁇ s and good pigment wetting properties.

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)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Paper (AREA)
  • Absorbent Articles And Supports Therefor (AREA)

Abstract

On décrit une résine soluble dans l'eau qui peut servir de dispersant. La résine est sensiblement constituée d'unités de: A) polyéthylène-glycol possédant de 5 à 100 unités d'oxyde d'éthylène; B) un composé contenant un ou plusieurs groupes allyles et/ou (méth)acrylates; et C) le produit réactionnel d'un ou plusieurs acides gras non saturés ou d'un ou plusieurs polyalcool(s) entièrement ou partiellement estérifiés avec des acides gras non saturés avec un composé, où le rapport molaire A:C est entre 0,5:1 et 4:1, et où le rapport molaire B:C est entre 0,5:1 et 4:1.
PCT/NL1990/000163 1989-10-31 1990-10-30 Resine soluble dans l'eau WO1991006586A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FI921927A FI921927A (fi) 1989-10-31 1992-04-29 Vattenloesligt harts.
NO92921698A NO921698L (no) 1989-10-31 1992-04-30 Vannopploeslig harpiks

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US42937489A 1989-10-31 1989-10-31
US429,374 1989-10-31

Publications (1)

Publication Number Publication Date
WO1991006586A1 true WO1991006586A1 (fr) 1991-05-16

Family

ID=23702963

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1990/000163 WO1991006586A1 (fr) 1989-10-31 1990-10-30 Resine soluble dans l'eau

Country Status (7)

Country Link
EP (1) EP0498834A1 (fr)
AU (1) AU6711390A (fr)
CA (1) CA2072096A1 (fr)
FI (1) FI921927A (fr)
HU (1) HU9201429D0 (fr)
NO (1) NO921698L (fr)
WO (1) WO1991006586A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10142991C2 (de) * 2001-08-31 2003-04-10 Dynea Moers Gmbh Additiv zur Verlängerung der Offenzeit von wäßrigen Zusammensetzungen enthaltend Poymerdispersionen
EP1640389A1 (fr) * 2004-09-14 2006-03-29 Byk-Chemie GmbH Copolymères, leur procédé de fabrication et leur usage comme agent mouillant ou dispersant
US10836910B2 (en) 2015-04-01 2020-11-17 Swimc Llc Pigment dispersion

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Database WPI Acces Nb. 74-35278v(19) Derwent Publication, Ltd., (London, GB), & JP, A, 48080130 (DAINIPPON PAINT) 26 October 1973 see Abstract. *
Database WPI Acces Nb. 74-35278v(19) Derwent Publication, Ltd., (London, GB), & JP-A-48080130 (DAINIPPON PAINT) 26 October 1973 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10142991C2 (de) * 2001-08-31 2003-04-10 Dynea Moers Gmbh Additiv zur Verlängerung der Offenzeit von wäßrigen Zusammensetzungen enthaltend Poymerdispersionen
EP1640389A1 (fr) * 2004-09-14 2006-03-29 Byk-Chemie GmbH Copolymères, leur procédé de fabrication et leur usage comme agent mouillant ou dispersant
DE102004044879A1 (de) * 2004-09-14 2006-03-30 Byk-Chemie Gmbh Copolymerisate, deren Herstellung und Verwendung als Netz- und Dispergiermittel
KR101204967B1 (ko) 2004-09-14 2012-11-26 비와이케이-케미 게엠베하 공중합체, 그의 제조 방법과 습윤제 및 분산제로서의 용도
US10836910B2 (en) 2015-04-01 2020-11-17 Swimc Llc Pigment dispersion
US11655372B2 (en) 2015-04-01 2023-05-23 Swimc Llc Pigment dispersion

Also Published As

Publication number Publication date
NO921698L (no) 1992-06-30
FI921927A0 (fi) 1992-04-29
FI921927A (fi) 1992-04-29
NO921698D0 (no) 1992-04-30
AU6711390A (en) 1991-05-31
CA2072096A1 (fr) 1991-05-01
EP0498834A1 (fr) 1992-08-19
HU9201429D0 (en) 1992-08-28

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