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WO1998058030A1 - Pate de matage pour systemes cationiques - Google Patents

Pate de matage pour systemes cationiques Download PDF

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Publication number
WO1998058030A1
WO1998058030A1 PCT/GB1998/001588 GB9801588W WO9858030A1 WO 1998058030 A1 WO1998058030 A1 WO 1998058030A1 GB 9801588 W GB9801588 W GB 9801588W WO 9858030 A1 WO9858030 A1 WO 9858030A1
Authority
WO
WIPO (PCT)
Prior art keywords
matting
epoxy resin
silica
monomer
weight
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/GB1998/001588
Other languages
English (en)
Inventor
Gemma Morea-Swift
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.)
Ineos Silicas Ltd
Original Assignee
Joseph Crosfield and Sons Ltd
Crosfield Ltd
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 Joseph Crosfield and Sons Ltd, Crosfield Ltd filed Critical Joseph Crosfield and Sons Ltd
Priority to CA002293290A priority Critical patent/CA2293290A1/fr
Priority to EP98924489A priority patent/EP0991728A1/fr
Priority to AU76682/98A priority patent/AU7668298A/en
Priority to JP50392999A priority patent/JP2002508012A/ja
Priority to BR9810042-4A priority patent/BR9810042A/pt
Publication of WO1998058030A1 publication Critical patent/WO1998058030A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3072—Treatment with macro-molecular organic compounds
    • 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
    • C09D7/42—Gloss-reducing agents
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/02—Amorphous compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/51—Particles with a specific particle size distribution
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
    • C01P2004/82—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases
    • C01P2004/84—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases one phase coated with the other
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/12—Surface area
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/14—Pore volume
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/16—Pore diameter
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/16—Pore diameter
    • C01P2006/17—Pore diameter distribution
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Definitions

  • the present invention relates to a matting paste for cationic systems.
  • 100% solid coatings formulations can be manufactured which will crosslink under Ultra Violet light. They contain oligomers, photoreactive initiators and various additives.
  • UV formulations Three major classes of photocurable resins may be used in UV formulations: i) acrylated oligomers, ii) unsaturated polyesters and iii) cycloaliphatic and bisphenol A epoxies.
  • Acrylated oligomers and unsaturated polyesters can polymerise and crosslink when they are mixed with chemicals which produce free radicals when exposed to Ultraviolet light.
  • Cycloaliphatic and bisphenol A epoxies can polymerise and crosslink when they are mixed with sulphonium salts which decompose under Ultraviolet light, produce an acid catalyst which initiate the reaction. This mechanism of curing is defined "Cationic Curing" .
  • Nitrogen surface area is determined by standard nitrogen adsorption methods of Brunauer, Emmett and Teller (BET) using a multipoint method with an ASAP 2400 apparatus supplied by Micromeritics of the USA. The samples are outgassed under vacuum at 270 deg.C for at least one hour before measurement. Surface area is calculated from the volume of nitrogen gas adsorbed at P/Po 0.98.
  • This apparatus also provides the pore size distribution from which it is possible to get the pore size (D 10 ) for which 10% of the pores are below this pore size. In the same manner is possible to get the pore size for which 50% (D 50 ) and 90% (D 90 ) of the pores are below this pore size. Additionally the pore volume (cm3/g) for a given range of pore size can be obtained from the desorption curve.
  • the weight mean particle size is determined with the aid of a Malvern Mastersizer using a 100 mm path length lens. This instrument, made by Malvern Instruments,
  • Worcestershire uses the principle of Fraunhoffer diffraction utilising a low power He/Ne laser. Before measurement the sample is dispersed ultrasonically in water for a period of 7 minutes to form an aqueous suspension. The Malvern Mastersizer measures the weight particle size distribution of the silica. The weight mean particle size (d 50 ) , the 10 percentile (d 10 ) and the 90 percentile (d 90 ) are easily obtained from the data generated by the instrument. iii. Matting efficiency
  • the resin, diluent, additive and photoinitiator were weighed in an amber brown jar and stirred for 30 seconds at 500 rpm using an Heidolph stirrer equipped with Cowles head. The silica was then added and all was stirred at 3000 rpm for ten minutes. The system was allowed to deaerate and then drawn down onto black Leneta 7C cards using a 25 microns K-Bar applicator. The cards were cured at 3m/min using one Fusion H lamp of 300W/inch. Gloss at 60° was measured on cured films using a Multiglossmeter by BYK.
  • the amorphous silicas used in this invention has a pore volume between 1.0 and 2.0 ml/g, preferably at least 1.8 ml/g as measured by Nitrogen Porosimetry, a surface area between 200 and 500 sq.m/g and an average particle size, as measured by Malvern between 4.0 and 12.0 microns.
  • the amorphous silica is a wax coated silica which, before coating, has a pore volume between 1.0 and 2.0 ml/g, preferably at least 1.8 ml/g as measured by Nitrogen Porosimetry, a surface area between 200 and 500 sq.m/g and an average particle size, as measured by Malvern between 4.0 and 12.0 microns.
  • the was coating preferably represents 6 to 15% by weight of the weight of the uncoated silica.
  • the wax comprises a microcrystalline wax or a polyethylene wax.
  • the matting monomer is selected within the group consisting in vinyl ether monomer containing one or more functional groups and acrylate monomer containing one or more functional groups or mixtures thereof. More preferably the matting monomer is selected within the group consisting in Triethylene glycol divinyl ether (DVE-3), 1,4-Cyclohexane dimethanol divinyl ether (CHVE), Hexanedioldivinylether, Ethylvinylether, Propylvinylether, Isobutylvinylether, Hexanedioldivinylether, Tripropylenglycole triacrylate (TPGDA) , Dipropylenglycole diacrylate (DPGDA), 1, ⁇ -Hexanediol diacrylate (HDDA) , Trimethylpropane triacrylate (TMPTA) , Ethoxylated trimethylpropane triacrylate (EO-TMPTA) , Propoxylated glycerol triacryl
  • It is second object of the present invention to provide a photocurable cationic system comprising 40 to 80% w/w of an epoxy resin and 20 to 60% w/w of a matting paste.
  • the epoxy resin is selected within the group consisting in cycloaliphatic epoxy resin or a bisphenol A epoxy resin or a mixture thereof.
  • It is a third object of the present invention to provide a photocurable cationic system comprising 40 to 80% w/w of an epoxy resin with a matting efficiency of less than 40 gloss units, preferably less than 30 gloss units, more preferably less than 20 gloss units.
  • the epoxy resin is selected within the group consisting in cycloaliphatic epoxy resin or a bisphenol A epoxy resin or a mixture thereof.
  • Formulations can be manufactured either by successive addition of the various components or by making a matting paste with silica and the matting diluent that can be used to add to the gloss paint for the purpose.
  • acrylated diluent is any of the following group (1, 6-hexanediol diacrylate (HDDA), and tripropylenglycole triacrylate (TPGDA) ) and Irgacure 184 is a free radical photoinitiator. Results obtained from Formulation 3 are reported in Table 3.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic 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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Le procédé selon l'invention consiste à utiliser 10 à 40 % en poids de diluants, tels que des éthers de vinyle (comme le CHVE, DVE3) et des acrylates (HDDA, TPGDA, DPGDA) avec une résine époxy cycloaliphatique pour améliorer l'effet de silice poreuse. Ce procédé permet de fabriquer des revêtements mats et semi-brillants à l'aide d'un système cationique ou hybride (séchage cationique/à radical libre) sans nuire aux autres propriétés de films requises.
PCT/GB1998/001588 1997-06-16 1998-06-01 Pate de matage pour systemes cationiques Ceased WO1998058030A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002293290A CA2293290A1 (fr) 1997-06-16 1998-06-01 Pate de matage pour systemes cationiques
EP98924489A EP0991728A1 (fr) 1997-06-16 1998-06-01 Pate de matage pour systemes cationiques
AU76682/98A AU7668298A (en) 1997-06-16 1998-06-01 Matting paste for cationic systems
JP50392999A JP2002508012A (ja) 1997-06-16 1998-06-01 カチオン塗料系用の艶消ペースト
BR9810042-4A BR9810042A (pt) 1997-06-16 1998-06-01 Pasta de fosqueamento para uso como um agente de fosqueamento em um sistema catiÈnico, e, sistema catiÈnico fotocurável

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9712591.8 1997-06-16
GBGB9712591.8A GB9712591D0 (en) 1997-06-16 1997-06-16 Matting paste for cationic systems

Publications (1)

Publication Number Publication Date
WO1998058030A1 true WO1998058030A1 (fr) 1998-12-23

Family

ID=10814312

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/001588 Ceased WO1998058030A1 (fr) 1997-06-16 1998-06-01 Pate de matage pour systemes cationiques

Country Status (9)

Country Link
EP (1) EP0991728A1 (fr)
JP (1) JP2002508012A (fr)
KR (1) KR20010013796A (fr)
CN (1) CN1260817A (fr)
AU (1) AU7668298A (fr)
BR (1) BR9810042A (fr)
CA (1) CA2293290A1 (fr)
GB (1) GB9712591D0 (fr)
WO (1) WO1998058030A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001004217A3 (fr) * 1999-04-13 2001-08-23 Grace Gmbh & Co Kg Agent de matite pour revetements durcissables par rayonnement
US6770128B1 (en) 1999-04-13 2004-08-03 Grace Gmbh & Co. Kg Matting agent radiation for curing coatings
US8197654B2 (en) 2009-01-22 2012-06-12 Ppg Industries Ohio, Inc. Methods for preparing an electrodepositable coating composition
US10370519B2 (en) 2012-07-24 2019-08-06 Akzo Nobel Coatings International B.V. Matting paste composition
CN110951298A (zh) * 2019-11-29 2020-04-03 湖南柯盛新材料有限公司 一种双组份环氧哑光美缝剂
CN111748234A (zh) * 2020-07-07 2020-10-09 威远达威木业有限公司 一种阳离子消光填料及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5347883B2 (ja) * 2009-09-30 2013-11-20 大日本印刷株式会社 化粧シート

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5221337A (en) * 1990-02-14 1993-06-22 W. R. Grace & Co.-Conn. SiO2 flatting agent, process for its production and its use
US5460857A (en) * 1991-06-07 1995-10-24 Basf Lacke + Farben Ag Method of producing dull paint surfaces
WO1995031508A1 (fr) * 1994-05-11 1995-11-23 Crosfield Limited Agent matant a base de silice enrobe de cire

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5221337A (en) * 1990-02-14 1993-06-22 W. R. Grace & Co.-Conn. SiO2 flatting agent, process for its production and its use
US5460857A (en) * 1991-06-07 1995-10-24 Basf Lacke + Farben Ag Method of producing dull paint surfaces
WO1995031508A1 (fr) * 1994-05-11 1995-11-23 Crosfield Limited Agent matant a base de silice enrobe de cire

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001004217A3 (fr) * 1999-04-13 2001-08-23 Grace Gmbh & Co Kg Agent de matite pour revetements durcissables par rayonnement
JP2003522219A (ja) * 1999-04-13 2003-07-22 グレース・ゲーエムベーハー・ウント・コムパニー・カーゲー 放射線硬化コーティング用の艶消剤
US6770128B1 (en) 1999-04-13 2004-08-03 Grace Gmbh & Co. Kg Matting agent radiation for curing coatings
CN1322072C (zh) * 1999-04-13 2007-06-20 格雷斯股份有限两合公司 用于辐射固化涂料的消光剂
US8197654B2 (en) 2009-01-22 2012-06-12 Ppg Industries Ohio, Inc. Methods for preparing an electrodepositable coating composition
US10370519B2 (en) 2012-07-24 2019-08-06 Akzo Nobel Coatings International B.V. Matting paste composition
CN110951298A (zh) * 2019-11-29 2020-04-03 湖南柯盛新材料有限公司 一种双组份环氧哑光美缝剂
CN110951298B (zh) * 2019-11-29 2021-09-07 湖南柯盛新材料有限公司 一种双组份环氧哑光美缝剂
CN111748234A (zh) * 2020-07-07 2020-10-09 威远达威木业有限公司 一种阳离子消光填料及其制备方法

Also Published As

Publication number Publication date
BR9810042A (pt) 2000-08-29
KR20010013796A (ko) 2001-02-26
AU7668298A (en) 1999-01-04
CA2293290A1 (fr) 1998-12-23
JP2002508012A (ja) 2002-03-12
GB9712591D0 (en) 1997-08-20
EP0991728A1 (fr) 2000-04-12
CN1260817A (zh) 2000-07-19

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