WO1988002382A1 - Resine de dispersion d'un pigment, comprenant un acide contenant du phosphore - Google Patents

Resine de dispersion d'un pigment, comprenant un acide contenant du phosphore Download PDF

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Publication number
WO1988002382A1
WO1988002382A1 PCT/US1987/002387 US8702387W WO8802382A1 WO 1988002382 A1 WO1988002382 A1 WO 1988002382A1 US 8702387 W US8702387 W US 8702387W WO 8802382 A1 WO8802382 A1 WO 8802382A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
pigment
acid
carbon atoms
esters
Prior art date
Application number
PCT/US1987/002387
Other languages
English (en)
Inventor
Jozef Theresia Huybrechts
Guido Richard Louis Van Den Bosch
Rudolf Felix Landriette Verhaegen
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Publication of WO1988002382A1 publication Critical patent/WO1988002382A1/fr

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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
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • 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
    • C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment

Definitions

  • the present invention comprises a pigment dispersant. More particularly, it comprises such a dispersant having an acrylic resin containing organic acid and strong-acid phosphorus-containing monomers.
  • Sulfur-and phosphorus-containing monomers including 2-acrylamide-2-methylpropane sulfonic acid (AMPS)
  • AMPS 2-acrylamide-2-methylpropane sulfonic acid
  • acrylics and other monomers in various proportions for a variety of purposes, including for use in dispersing sediments in water.
  • an optimum dispersant resin for use in water-based coating compositions has remained an elusive desideratum.
  • U.S. Patent 4,450,013 - Hirsch et al. (1984) teaches a pigment grinding or dispersing resin of, for instance, 40-90% by weight acrylic acid, 10-60% AMPS, and 0-10% acrylonitrile, or equivalent monomers. (Parts, percentages and proportions herein are by weight except where indicated otherwise).
  • U.S. Patent 3,898,037 - Lange et al. (1975) teaches acrylamido-sulfonic acid polymers such as AMPS which may be copolymerized with other acrylics, and their use in corrosion inhibition.
  • U.S. Patent 4,177,178 - Das et al. (1979) teaches the use of A MPS copolymerized with other acrylics including long chain acrylics such as stearyl methacrylate, with a molecular weight of 15,000 to 100,000. These are said to be used to make thermosetting automotive topcoat paints.
  • European Patent Publication 129 , 329 - Farrar et al. (1984) teaches pigment dispersions using copolymers of acrylic acid with 1-50% AMPS having molecular weights in the range of 1,000 to 5,000, or up to 5700, with a low polydispersxty.
  • European Patent Publication 58,865-Perrey et al. (1982) teaches pigment dispersants with 1-10% pigment, using various acrylic sulfonic acid polymers.
  • European Patent Publication 170,474 - Backhouse (1986). teaches the use of phosphorus-containing compounds in water-based polymers to reducing gasing from metal pigments.
  • the present invention provides a pigment dispersant resin comprising copolymerized units of the following monomers in weight percent based on the polymer solids:
  • R is H or CH 3
  • R 1 is an ester, amido, alkyl, or ether linkage having 1-4 carbon atoms
  • the phosphorus-containing monomer is methacxyloxyethylphosphate (MOP).
  • the invention also includes water-based dispersions of the esin of the invention (including more or less of the resin in solution), with 50-150% of the amount of tertiary amine needed for neutralization. Pigment dispersions are also needed.
  • the preferred phosphorus-containing monomer for the invention is
  • Water based coating composition technology is based on a higher molecular weight or crosslinked latex giving rheology control with a water dispersible or soluble crosslinker such as a methylated melamine resin.
  • the amount: of inorganic acid in the dispersing resin is important for the stability of and the compatibility with the latex. With larger amounts than in this invention, one could expect real problems in film properties and compatibility, at least with certain resins. It is also k nown that reactive melamine resins are sensitive to self condensation and hydrolysis in presence of strong acids giving unstable products in the can. Too high acid values in general do give cured films which are sensitive to humidity.
  • the rest of the copolymer composition can be based on any unsaturated monomer such as acrylate, methacrylate, styrene, vinyl maleate, acrylamides or methacrylamides, or acrylonitrile or methacrylonitrile.
  • Certain preferred compositions contain MMA (methylmethacrylate) and BA (butylacrylate).
  • the copolymers should also have preferably hydroxy functionality to become an integral part of the cured polymer network.
  • HEMA hydroxyethyl methacrylate
  • HEA hydroxyethylacrylate
  • HPMA hydroxy-propylacrylate
  • HEMA hydroxypropylmethacrylate
  • HPMA hydroxybutyl acrylate
  • the copolymers are made by radical polymerization using solvents as diluents which are preferably water soluble.
  • Isopropanol (IP) is in this technology a good candidate since it forms a low boiling azeotrope with water.
  • Chain transfer agents e.g. mercaptans
  • Triganox 25C75 20.5 t-butylperoxy- pivalate from AKZO Add monomer + initiator blend over 3 hour period Triganox 25C75 : 10 IP : 40
  • Example 2 In variations on example 1, the following resin solutions were prepared.
  • Example 5 Pigment Dispersion (B) Ti-pure 902 titanium dioxide from Du Pont The same tests were run as above with following constraints:

Landscapes

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

Abstract

Des polymères acryliques, avec un acide carboxylique et de petites quantités d'acides forts contenant du phosphore constituent de bons agents de dispersion de pigments, à utiliser dans des compositions de revêtement aqueuses.
PCT/US1987/002387 1986-09-30 1987-09-25 Resine de dispersion d'un pigment, comprenant un acide contenant du phosphore WO1988002382A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US91340286A 1986-09-30 1986-09-30
US913,402 1986-09-30
US93425486A 1986-11-24 1986-11-24
US934,254 1986-11-24

Publications (1)

Publication Number Publication Date
WO1988002382A1 true WO1988002382A1 (fr) 1988-04-07

Family

ID=27129623

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1987/002387 WO1988002382A1 (fr) 1986-09-30 1987-09-25 Resine de dispersion d'un pigment, comprenant un acide contenant du phosphore

Country Status (2)

Country Link
EP (1) EP0283511A4 (fr)
WO (1) WO1988002382A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2218708A (en) * 1988-05-19 1989-11-22 Int Paint Plc Marine antifouling paint
EP0398487A1 (fr) * 1989-04-27 1990-11-22 Imperial Chemical Industries Plc Dispersion aqueuse de particules inorganiques
EP0412027A1 (fr) * 1989-08-04 1991-02-06 Coatex S.A. Application aux suspensions aqueuses pigmentaires de carbonate de calcium d'un agent polycarboxylique à fonction phosphatée ou phosphonée inhibant l'effet de choc provoqué par l'introduction d'un électrolyte sous forme concentrée
US5109090A (en) * 1988-10-10 1992-04-28 Coatex S.A. Compatibility agent for aqueous polypigmentary suspensions containing hydrated calcium sulfate
EP0705892A2 (fr) * 1994-09-21 1996-04-10 ALBRIGHT & WILSON UK LIMITED Dispersion de particules solides dans l'eau
GB2359557A (en) * 2000-02-25 2001-08-29 Nippon Paint Co Ltd Water-based coating composition
FR2867478A1 (fr) * 2004-03-10 2005-09-16 Cray Valley Sa Dispersion aqueuse de polymere pour revetement barriere

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001150A (en) * 1970-11-25 1977-01-04 Kansai Paint Company, Ltd. Composition for preparing electroconductive resin comprising an unsaturated polyester and phosphoric or sulfonic unsaturated ester
EP0170474A2 (fr) * 1984-08-02 1986-02-05 Imperial Chemical Industries Plc Compositions aqueuses de revêtement contenant un pigment métallique et ayant une tendance réduite à former un gaz lors du stockage
US4612384A (en) * 1981-07-29 1986-09-16 Kuraray Co., Ltd. Phosphate monoester adhesive composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6119651A (ja) * 1984-07-06 1986-01-28 Toyo Soda Mfg Co Ltd 着色ポリマ−エマルジヨンおよびその製造方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001150A (en) * 1970-11-25 1977-01-04 Kansai Paint Company, Ltd. Composition for preparing electroconductive resin comprising an unsaturated polyester and phosphoric or sulfonic unsaturated ester
US4612384A (en) * 1981-07-29 1986-09-16 Kuraray Co., Ltd. Phosphate monoester adhesive composition
EP0170474A2 (fr) * 1984-08-02 1986-02-05 Imperial Chemical Industries Plc Compositions aqueuses de revêtement contenant un pigment métallique et ayant une tendance réduite à former un gaz lors du stockage

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0283511A4 *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2218708A (en) * 1988-05-19 1989-11-22 Int Paint Plc Marine antifouling paint
US5109090A (en) * 1988-10-10 1992-04-28 Coatex S.A. Compatibility agent for aqueous polypigmentary suspensions containing hydrated calcium sulfate
US5110358A (en) * 1988-10-10 1992-05-05 Coatex S.A. Compatibility agent for aqueous polypigmentary suspensions containing hydrated calcium sulfate
EP0398487A1 (fr) * 1989-04-27 1990-11-22 Imperial Chemical Industries Plc Dispersion aqueuse de particules inorganiques
US5084502A (en) * 1989-04-27 1992-01-28 Imperial Chemical Industries Plc Dispersions
EP0412027A1 (fr) * 1989-08-04 1991-02-06 Coatex S.A. Application aux suspensions aqueuses pigmentaires de carbonate de calcium d'un agent polycarboxylique à fonction phosphatée ou phosphonée inhibant l'effet de choc provoqué par l'introduction d'un électrolyte sous forme concentrée
FR2650594A1 (fr) * 1989-08-04 1991-02-08 Coatex Sa Application aux suspensions aqueuses pigmentaires de carbonate de calcium d'un agent polycarboxylique a fonction phosphatee ou phosphonee inhibant l'effet de choc provoque par l'introduction d'un electrolyte sous forme concentree
US5145902A (en) * 1989-08-04 1992-09-08 Coatex S.A. Application to aqueous calcium carbonate pigment suspensions of a polycarboxylic agent with phosphoric or phosphonic groups which inhibit the shock effect caused by the introduction of an electrolyte at high concentration
EP0705892A2 (fr) * 1994-09-21 1996-04-10 ALBRIGHT & WILSON UK LIMITED Dispersion de particules solides dans l'eau
EP0705892A3 (fr) * 1994-09-21 1997-08-13 Albright & Wilson Uk Ltd Dispersion de particules solides dans l'eau
GB2359557A (en) * 2000-02-25 2001-08-29 Nippon Paint Co Ltd Water-based coating composition
US6541070B2 (en) 2000-02-25 2003-04-01 Nippon Paint Co. Ltd. Method of forming a composite coating film comprising a pigment and resin emulsion
GB2359557B (en) * 2000-02-25 2003-12-24 Nippon Paint Co Ltd Method of forming composite coating film
FR2867478A1 (fr) * 2004-03-10 2005-09-16 Cray Valley Sa Dispersion aqueuse de polymere pour revetement barriere
WO2005097853A1 (fr) * 2004-03-10 2005-10-20 Cray Valleys.A. Dispersion aqueuse de polymere pour revetement barriere
CN1950408B (zh) * 2004-03-10 2011-07-27 克雷·瓦利有限公司 用于隔离涂料的聚合物含水分散体

Also Published As

Publication number Publication date
EP0283511A4 (fr) 1989-01-26
EP0283511A1 (fr) 1988-09-28

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