RU2219571C2 - Heavy metal-free coating composition - Google Patents

Heavy metal-free coating composition Download PDF

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RU2219571C2
RU2219571C2 RU2000129661/04A RU2000129661A RU2219571C2 RU 2219571 C2 RU2219571 C2 RU 2219571C2 RU 2000129661/04 A RU2000129661/04 A RU 2000129661/04A RU 2000129661 A RU2000129661 A RU 2000129661A RU 2219571 C2 RU2219571 C2 RU 2219571C2
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Russia
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composition according
compound
sensitizer
content
formula
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RU2000129661/04A
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Russian (ru)
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RU2000129661A (en
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Любомир МИСЕВ (CH)
Любомир Мисев
Аллан Францис КУННИНГАМ (US)
Аллан Францис КУННИНГАМ
Гизель БАУДИН (CH)
Гизель БАУДИН
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Циба Спешиалти Кемикалз Холдинг Инк.
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
    • 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
    • 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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/02—Polyalkylene oxides
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/10—Block or graft copolymers containing polysiloxane sequences
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/38—Treatment before imagewise removal, e.g. prebaking

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Epoxy Resins (AREA)

Abstract

FIELD: polymer materials. SUBSTANCE: UV-solidificated cation-polymerizing contains: 40-70% of mono-, bis-, or higher aliphatic or aromatic glycidyl ethers; 20-55% of titanium dioxide; as photoinitiator, 0.5-10% of at least one hexafluorophosphate salt of iodonium of formula:
Figure 00000002
, where R1, R2, R3 and R4, independently, represent hydrogen, C1-C20-alkyl, or unsubstituted or hydroxyl-substituted C1-C20- alcoxy, provided that at least one of R1, R2, R3 or R4 is not hydrogen atom; and 0.1-3% of sensitizer. Invention also provides coated substrate and photopolymerization method. EFFECT: enabled preparation of heavy metal-free composition with good resistance to yellowing. 10 cl, 1 tbl, 18 ex

Description

Текст описания в факсимильном виде (см. графическую часть) Те Description text in facsimile form (see graphic part)

Claims (10)

1. УФ-отверждаемая катионно-полимеризуемая композиция, содержащая (а) моно-, бис- или высшие алифатические или ароматические глицидиловые эфиры, (b) двуокись титана, (с) в качестве фотоинициатора по крайней мере одну гексафторфосфатную соль иодония формулы I1. UV-curable cation-polymerizable composition containing (a) mono-, bis- or higher aliphatic or aromatic glycidyl ethers, (b) titanium dioxide, (c) as photoinitiator at least one iodonium hexafluorophosphate salt of formula I
Figure 00000029
Figure 00000029
 где R1, R2, R3 и R4 каждый независимо один от другого представляет водород, С1-С20алкил или незамещенный или гидроксилзамещенный С1-С20алкокси, при условии, что по крайней мере один из R1, R2, R3 или R4 не является атомом водорода;where R 1 , R 2 , R 3 and R 4 each independently of one another is hydrogen, C 1 -C 20 alkyl or unsubstituted or hydroxyl-substituted C 1 -C 20 alkoxy, provided that at least one of R 1 , R 2 , R 3 or R 4 is not a hydrogen atom; (d) соединение-сенсибилизатор, при этом содержание компонента (а) составляет 40-70%, содержание двуокиси титана (b) составляет 20-55%, содержание фотоинициатора (с) составляет 0,5-10% и содержание соединения-сенсибилизатора (d) составляет 0,1-3%.(d) a sensitizer compound, wherein the content of component (a) is 40-70%, the titanium dioxide content (b) is 20-55%, the photoinitiator content (c) is 0.5-10%, and the content of the sensitizer compound ( d) is 0.1-3%. 2. Композиция по п.1, отличающаяся тем, что в соединении формулы I R2 представляет С1-С12алкил, в частности, изобутил или додецил, а R1, R3 и R4 являются атомами водорода.2. The composition according to claim 1, characterized in that in the compound of formula IR 2 represents C 1 -C 12 alkyl, in particular isobutyl or dodecyl, and R 1 , R 3 and R 4 are hydrogen atoms. 3. Композиция по п.1, отличающаяся тем, что соединение-сенсибилизатор (d) представляет собой соединение, выбранное из группы, состоящей из антраценов, ксантонов, бензофенонов и тиоксантонов.3. The composition according to claim 1, characterized in that the sensitizer compound (d) is a compound selected from the group consisting of anthracenes, xanthones, benzophenones and thioxanthones. 4. Композиция по п.3, отличающаяся тем, что соединение-сенсибилизатор (d) представляет собой производное тиоксантона.4. The composition according to claim 3, characterized in that the compound-sensitizer (d) is a derivative of thioxantone. 5. Композиция по п.1, отличающаяся тем, что глицидиловый эфир (а) представляет собой соединение формулы II5. The composition according to claim 1, characterized in that the glycidyl ether (a) is a compound of formula II
Figure 00000030
Figure 00000030
 где х означает число от 1 до 6;where x is a number from 1 to 6; R5 представляет одновалентный или шестивалентный алкильный или арильный радикал.R 5 represents a monovalent or hexavalent alkyl or aryl radical. 6. Субстрат с нанесенным покрытием, по крайней мере одна поверхность которого покрыта композицией по п.1.6. The coated substrate, at least one surface of which is coated with the composition according to claim 1. 7. Субстрат по п.6, отличающийся тем, что указанную композицию по п.1 наносят при толщине покрытия 0,1-100 мкм.7. The substrate according to claim 6, characterized in that the composition according to claim 1 is applied at a coating thickness of 0.1-100 microns. 8. Способ фотополимеризации композиции по п.1, предусматривающий облучение указанной композиции светом с длиной волны 200-600 нм.8. The method of photopolymerization of a composition according to claim 1, comprising irradiating said composition with light with a wavelength of 200-600 nm. 9. Способ по п.8, отличающийся тем, что после облучения проводят термообработку.9. The method according to claim 8, characterized in that after irradiation, heat treatment is carried out. 10. Способ по п.8, отличающийся тем, что он использован для получения покрытий, красок, типографских красок, порошкообразных покрытий, ламинирующих адгезивов или композиций для зубной пасты, в частности белых эмалевых композиций.10. The method according to claim 8, characterized in that it is used to obtain coatings, paints, printing inks, powder coatings, laminating adhesives or compositions for toothpaste, in particular white enamel compositions.
RU2000129661/04A 1998-04-24 1999-04-14 Heavy metal-free coating composition RU2219571C2 (en)

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EP98810361.0 1998-04-24
EP98810361 1998-04-24

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RU2219571C2 true RU2219571C2 (en) 2003-12-20

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EP (1) EP1084456A1 (en)
JP (1) JP2002513078A (en)
KR (1) KR20010042957A (en)
AU (1) AU758652B2 (en)
BR (1) BR9909890A (en)
CA (1) CA2329012A1 (en)
RU (1) RU2219571C2 (en)
WO (1) WO1999056177A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19961355A1 (en) 1999-12-17 2001-06-21 S & C Polymer Silicon & Compos Photoinitiator system with titanocene initiators
DE19961347A1 (en) * 1999-12-17 2001-06-21 S & C Polymer Silicon & Compos Photoinitiator system with acylphosphine oxide initiators
GB0516515D0 (en) * 2005-08-11 2005-09-21 Sun Chemical Bv A jet ink and ink jet printing process
EP2428501B1 (en) * 2009-05-08 2018-12-12 Nippon Shokubai Co., Ltd. Diaryliodonium salt mixture and process for production thereof, and process for production of diaryliodonium compound
JP5485583B2 (en) * 2009-05-08 2014-05-07 株式会社日本触媒 Method for producing diaryliodonium compound
CN104497277A (en) * 2014-11-26 2015-04-08 南京凯泰化工科技有限公司 Free-radical photoinitiator and preparation method thereof
RU2646003C2 (en) * 2017-06-06 2018-03-01 Федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный технический университет" (ВолгГТУ) Photopolymerisable composition for accelerated formation of protective coatings

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US4399071A (en) * 1982-03-12 1983-08-16 General Electric Company Method for making diaryliodonium salts
DE4002682A1 (en) * 1990-01-31 1991-08-01 Herberts Gmbh METHOD FOR COATING SUBSTRATES WITH UV-RADIATING COATING AGENTS
TW460509B (en) * 1996-07-12 2001-10-21 Ciba Sc Holding Ag Curing process for cationically photocurable formulations

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EP1084456A1 (en) 2001-03-21
JP2002513078A (en) 2002-05-08
CA2329012A1 (en) 1999-11-04
KR20010042957A (en) 2001-05-25
AU758652B2 (en) 2003-03-27
AU3707799A (en) 1999-11-16
WO1999056177A1 (en) 1999-11-04

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Effective date: 20040415