WO2002100961A1 - Primer composition for painted substrates - Google Patents

Primer composition for painted substrates Download PDF

Info

Publication number
WO2002100961A1
WO2002100961A1 PCT/US2002/018218 US0218218W WO02100961A1 WO 2002100961 A1 WO2002100961 A1 WO 2002100961A1 US 0218218 W US0218218 W US 0218218W WO 02100961 A1 WO02100961 A1 WO 02100961A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
primer composition
adhesive tape
painted
solution
Prior art date
Application number
PCT/US2002/018218
Other languages
English (en)
French (fr)
Inventor
Akihiko Nakayama
Tsuyoshi Asano
Masataka Ohishi
Original Assignee
3M Innovative Properties 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 3M Innovative Properties Company filed Critical 3M Innovative Properties Company
Publication of WO2002100961A1 publication Critical patent/WO2002100961A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D133/00Coating compositions based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04Homopolymers or copolymers of esters
    • C09D133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/062Copolymers with monomers not covered by C09D133/06
    • C09D133/064Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/003Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds

Definitions

  • the present invention relates to a primer composition to be used for improving the adhesion strength of an adhesive tape, and more particularly a decorative adhesive tape, to a substrate painted with a melamine resin paint or an anti-acid rain paint.
  • the primer composition is applied to the painted substrate before the adhesive tape is adhered to the painted substrate.
  • peripheral portions for example, door pillars
  • the peripheral portions for example, door pillars
  • the peripheral portions are coated to be black as a design of an automobile.
  • it has tended to become common to stick a black color adhesive tape on the peripheral portions in place of coating with a paint owing to environmental requirements to decrease the use of organic solvents in coating and owing to the reasons regarding the work processes.
  • Sticking such an adhesive tape for decoration can be carried out by directly sticking an adhesive tape, having an acrylic adhesive in an adhesion face, to object faces of the peripheral portions of the side windows, already coated with a ground color of the body. It can also be carried out by applying a resin composition, having a prescribed adhesive property to improve the adhesion force, to the adhesive tape to the object faces and then sticking an adhesive tape thereto.
  • a resin composition usable as an adhesive are compositions containing a copolymer having carboxyl groups in the molecule, a copolymer having amino groups, and the like as constituent components.
  • Japanese Patent Laid-Open No. 59-30872 discloses an aqueous composition for coating, which is an aqueous solution or an aqueous dispersion of an addition copolymerized resin obtained by reaction of a carboxyl-containing copolymer with an unsaturated aliphatic primary amine.
  • 6-322342 discloses a binary solution type adhesive composition containing (A) an aqueous solution of a polymer compound having carboxyl groups and/or sulfonic acid groups in the molecule and (B) an aqueous solution of an amino groupcontaining acrylic copolymer in the molecule and Japanese Patent Laid-Open No. 2655574 discloses an acrylic copolymer containing primary amine groups and carboxylic acid groups, respectively.
  • High shearing force can be applied partially between the side window peripheral portions to which an adhesive tape is adhered and the rim portions of the side windows through rubber members. When this occurs, the adhesion strength of the adhesive tape in the relevant portions can be low, and the adhesive tape can become wrinkled. Further, the adhesive tape is to be adhered to the coating to be the ground color of an automobile and there exist as the coating of the automobile are an acidic coating using an anti-acid rain paint and an alkaline coating using a melamine resin paint and a composition capable of improving the adhesion strength of the adhesive tape to the painted substrate painted with any of these paints is desired to be made available. However, conventional resin compositions disclosed in the above mentioned
  • Japanese Patent Laid-Open No. 59-30872, Japanese Patent Laid-open No. 6-322342, and Patent No. 2655574 are not proposed for a presumed purpose to adhere an adhesive tape to a painted substrate, so that the effect in such a purpose is not made clear.
  • the present invention has been developed taking such a conventional situation into consideration, and the purpose of the present invention is to provide a composition capable of improving the adhesion strength of an adhesive tape, especially the durability to shearing force in relation to the painted surface and making the adhesive tape usable for the case where the adhesive tape is adhered to any of the acidic paint and the alkaline paint.
  • the present invention provides a primer composition comprising (A) a graft copolymer of an acrylic copolymer grafted with an aminoalkyl group having a primary amino group in the terminal; (B) an acrylic copolymer having carboxyl group in the molecular chain; and (C) a solvent capable of dissolving or dispersing the component (A) and the component (B) therein as essential constituent components.
  • the primer composition of the present invention contains the component (A) excellent in adhesion to an acidic paint-coated surface (an anti-acid rain paint) and an acrylic adhesive (acidic) and the component (B) excellent in adhesion to an alkaline paint- coated surface (a melamine resin paint) in a single solution, the composition allows an adhesive tape containing an acrylic adhesive to be adhered to both of the alkaline paint- coated surface and the acidic paint-coated surface and improves the adhesion strength of the adhesive tape to the respective painted surfaces, especially the durability to the shearing force.
  • Japanese Patent Laid-Open No. 59-30872 and Patent No. 2655574 are basically different in terms of the constitution from the primer composition of the present invention in a point that they contain only one type of component as a copolymer and the composition disclosed in the Japanese Patent Laid-Open No. 6-322342 is different in a point that it is a two-solution-type adhesive composition.
  • the component (A) More particularly, it is preferable to use those having the amine-H equivalent from 350 to 1800 as the component (A) and those having the acid value (mg KOH g) from 10 to 110 as the component (B).
  • the stability (the coating strength, the heat resistance, the waterproofness, the weathering resistance, and the like) of the primer coating is improved, however the molecular weights are too high, that causes decrease of their solubility and increase of the viscosity of their solution, so that it is preferably to use those having weight average molecular weight of about 100, 000 for the component (A) and those having weight average molecular weight of 4600 to 14,000, for the component (B).
  • the glass transition temperature (Tg) of the component (A) and of the component (B) is preferably around room temperature. Practically, it is preferable to use those having Tg of 40 to
  • the solvents usable for the component (C) is those capable of dissolving or dispersing the two types of copolymers of the component (A) and the component (B) and normally, organic solvents are used, however in the case where hydrophilic groups are introduced in the component (A) and the component (B) to make them water-soluble resin or these components are emulsified, water may also be used.
  • theprimercomposition of the present invention may further contain a variety of additives such as an ultraviolet ray adsorbent, a heat stabilizer, a thickener and the like based on the necessity.
  • NK-350 resin solution (amino-H equivalent weight about 1,800; the weight average molecular weight around 100,000; Tg approximately 400°C), manufactured by Nippon Shokubai Co., Ltd., was used as the component (A) and SCX (a registered trade mark) 804 acrylic resin (acid value about 10; the weight average mlecular weight 14,000; and Tg approximately 60°C), manufactured by Johnson Polymer Corporation was used as the component (B).
  • Example 2
  • a primer composition solution was produced in the same manner as the foregoing Example 1 except that Joncryl (a registered trade mark) 611 acrylic resin (acid value about 53; the weight average molecular weight 8,100; and Tg approximately 50°C), manufactured by Johnson Polymer Corporation was used as the component (B).
  • Joncryl a registered trade mark 611 acrylic resin (acid value about 53; the weight average molecular weight 8,100; and Tg approximately 50°C), manufactured by Johnson Polymer Corporation was used as the component (B).
  • a primer composition solution was produced in the same manner as the foregoing Example 1 except that Polyment (a registered trade mark) NK-380 resin solution (amino-H equivalent weight about 700; the weight average molecular weight around 100,000; Tg approximately 100°C) , manufactured by Nippon Shokubai Co., Ltd., was used as the component (A) and Joncryl (a registered trade mark) 611 acrylic resin, manufactured by Johnson Polymer Corporation was used as the component (B).
  • Polyment a registered trade mark
  • NK-380 resin solution amino-H equivalent weight about 700; the weight average molecular weight around 100,000; Tg approximately 100°C
  • Joncryl a registered trade mark
  • 611 acrylic resin manufactured by Johnson Polymer Corporation
  • NK-350 resin solution manufactured by Nippon Shokubai Co., Ltd.
  • Joncryl a, registered trade mark 683 acrylic resin (acid value about 160; the weight average molecular weight 8,000; and Tq approximately 75°C), manufactured by Johnson Polymer Corporation
  • a primer composition solution containing 5% of solid matter and being in even solution state was produced using Polyment (a registered trade mark) NK-350 resin solution, manufactured by Nippon Shokubai Co., Ltd., was used as the component (A) but using no component for the component (B) and then diluting the resin solution to 5% of solid by methyl ethyl ketone.
  • the adhering method was according to JIS Z 0237 8.2.3. Controls were prepared by directly sticking only the adhesive tape to the melamine resin-painted steel plate and the anti-acid rain paintpainted steel plate without applying any primer composition solutions. Measurement of the durability to shearing force was carried out according to JIS Z 0237 11.3, except that the adhesion surface area was 10 x 10 mm.
  • the test pieces coated with the primer compositions of the Examples 1 to 6 according to the present invention showed higher durability to shearing force than the test pieces coated with the primer composition of the comparative Example 2 containing no component for the component (B) and also found that the test pieces were provided with the effect of improving adhesion strength to both the melamine resin-painted steel plate and the anti-acid rain paint-painted steel plate.
  • the test piece coated with the primer composition of the comparative Example 2 it took place a phenomenon that the primer composition was stripped from the melamine resin-painted steel plate (in other words, the primer composition was stripped while being left in the adhesive tape side) in tests 2 and 3. Such parting manner would be a serious problem in use of the adhesive tape to be adhered to an automobile.
  • the primer composition of the present invention contains a copolymer excellent in adhesion to the acidic paint-coated surface and a copolymer excellent in adhesion to the alkaline paint-coated surface in a single solution, so that the primer composition can be used preferably for sticking an adhesive tape to substrates painted any of the acidic paint and the alkaline paint and can improve the adhesion strength of the adhesive tape to the painted surface and especially remarkably improve the durability to the shearing force.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
PCT/US2002/018218 2001-06-08 2002-06-07 Primer composition for painted substrates WO2002100961A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001-174301 2001-06-08
JP2001174301A JP4856322B2 (ja) 2001-06-08 2001-06-08 塗装板用プライマー組成物

Publications (1)

Publication Number Publication Date
WO2002100961A1 true WO2002100961A1 (en) 2002-12-19

Family

ID=19015606

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2002/018218 WO2002100961A1 (en) 2001-06-08 2002-06-07 Primer composition for painted substrates

Country Status (2)

Country Link
JP (1) JP4856322B2 (ja)
WO (1) WO2002100961A1 (ja)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010063599A1 (de) * 2008-12-01 2010-06-10 Basf Se Wässrige bindemittelzusammensetzung enthaltend oligomere
WO2012171924A1 (de) 2011-06-14 2012-12-20 Tesa Se Primer zur verbesserung der adhäsion von klebebändern auf schwer verklebbaren kunststoffen und metallen
EP2789666A1 (de) 2013-04-11 2014-10-15 Tesa Se Schwarzer Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf Glasoberflächen
EP2789665A1 (de) 2013-04-11 2014-10-15 Tesa Se Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf hydrophilen Oberflächen, insbesondere Glasoberflächen
WO2015169575A1 (de) 2014-05-09 2015-11-12 Tesa Se Primer zur verbesserung der adhäsion von klebebändern auf hydrophilen oberflächen
WO2016030017A1 (de) 2014-08-29 2016-03-03 Tesa Se Primer für klebebänder
EP3231823A1 (de) 2016-04-13 2017-10-18 tesa SE Einfärbbarer primer
DE102016210536A1 (de) 2016-04-13 2017-10-19 Tesa Se Einfärbbarer Primer
US11560497B2 (en) * 2015-05-28 2023-01-24 3M Innovative Properties Company Adhesive sheet

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005288876A (ja) * 2004-03-31 2005-10-20 Three M Innovative Properties Co レセプターフィルム及びマーキングフィルム
WO2006013878A1 (ja) * 2004-08-05 2006-02-09 Nichiban Co., Ltd. 光硬化型シーリング剤に対する補修用シーラーの密着性向上剤
CN104220546B (zh) * 2012-03-30 2016-07-06 木本股份有限公司 易剥离性粘合膜及金属板的加工方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4826921A (en) * 1986-09-05 1989-05-02 International Paint Public Limited Company Coating composition
EP0336428A2 (en) * 1988-04-08 1989-10-11 Nippon Paint Co., Ltd. Curable composition
US5304607A (en) * 1989-07-04 1994-04-19 Courtaulds Coatings (Holdings) Limited Coating compositions

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2512596B2 (ja) * 1990-04-24 1996-07-03 積水化学工業株式会社 プライマ―を用いた貼付構造体
JPH05345868A (ja) * 1992-06-15 1993-12-27 Kuraray Co Ltd プライマー用組成物
JPH0931426A (ja) * 1995-07-13 1997-02-04 Oji Paper Co Ltd 自動車塗膜保護用粘着シート
JP3012898B2 (ja) * 1996-01-29 2000-02-28 三洋化成工業株式会社 金属蒸着用下塗り剤組成物
JPH1135888A (ja) * 1997-07-24 1999-02-09 Sekisui Chem Co Ltd プライマー樹脂組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4826921A (en) * 1986-09-05 1989-05-02 International Paint Public Limited Company Coating composition
EP0336428A2 (en) * 1988-04-08 1989-10-11 Nippon Paint Co., Ltd. Curable composition
US5304607A (en) * 1989-07-04 1994-04-19 Courtaulds Coatings (Holdings) Limited Coating compositions

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2009321590B2 (en) * 2008-12-01 2015-02-26 Basf Se Aqueous binder composition comprising oligomers
US20110237736A1 (en) * 2008-12-01 2011-09-29 Basf Se Aqueous binder composition comprising oligomers
WO2010063599A1 (de) * 2008-12-01 2010-06-10 Basf Se Wässrige bindemittelzusammensetzung enthaltend oligomere
US9096753B2 (en) 2008-12-01 2015-08-04 Basf Se Aqueous binder composition comprising oligomers
EP2370516B1 (de) 2008-12-01 2015-07-01 Basf Se Wässrige bindemittelzusammensetzung enthaltend oligomere
WO2012171924A1 (de) 2011-06-14 2012-12-20 Tesa Se Primer zur verbesserung der adhäsion von klebebändern auf schwer verklebbaren kunststoffen und metallen
DE102011077510A1 (de) 2011-06-14 2012-12-20 Tesa Se Primer zur Verbesserung der Adhäsion von Klebebändern auf schwer verklebbaren Kunststoffen und Metallen
EP2789666A1 (de) 2013-04-11 2014-10-15 Tesa Se Schwarzer Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf Glasoberflächen
DE102013206376A1 (de) 2013-04-11 2014-10-16 Tesa Se Schwarzer Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf Glasoberflächen
DE102013206369A1 (de) 2013-04-11 2014-10-16 Tesa Se Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf hydrophilen Oberflächen, insbesondere Glasoberflächen
EP2789665A1 (de) 2013-04-11 2014-10-15 Tesa Se Silan-Primer zur Verbesserung der Adhäsion von Klebebändern auf hydrophilen Oberflächen, insbesondere Glasoberflächen
WO2015169575A1 (de) 2014-05-09 2015-11-12 Tesa Se Primer zur verbesserung der adhäsion von klebebändern auf hydrophilen oberflächen
DE102014208814A1 (de) 2014-05-09 2015-11-12 Tesa Se Primer zur Verbesserung der Adhäsion von Klebebändern auf hydrophilen Oberflächen
WO2016030017A1 (de) 2014-08-29 2016-03-03 Tesa Se Primer für klebebänder
DE102014217245A1 (de) 2014-08-29 2016-03-03 Tesa Se Primer für Klebebänder
US10513634B2 (en) 2014-08-29 2019-12-24 Tesa Se Primer for adhesive tapes
US11560497B2 (en) * 2015-05-28 2023-01-24 3M Innovative Properties Company Adhesive sheet
EP3231823A1 (de) 2016-04-13 2017-10-18 tesa SE Einfärbbarer primer
DE102016210536A1 (de) 2016-04-13 2017-10-19 Tesa Se Einfärbbarer Primer

Also Published As

Publication number Publication date
JP4856322B2 (ja) 2012-01-18
JP2003003114A (ja) 2003-01-08

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