EP1576037A1 - Procede de formation de revetements reactifs - Google Patents

Procede de formation de revetements reactifs

Info

Publication number
EP1576037A1
EP1576037A1 EP03799570A EP03799570A EP1576037A1 EP 1576037 A1 EP1576037 A1 EP 1576037A1 EP 03799570 A EP03799570 A EP 03799570A EP 03799570 A EP03799570 A EP 03799570A EP 1576037 A1 EP1576037 A1 EP 1576037A1
Authority
EP
European Patent Office
Prior art keywords
organic substrate
inorganic
ethylenically unsaturated
groups
compounds
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.)
Withdrawn
Application number
EP03799570A
Other languages
German (de)
English (en)
Inventor
Martin Kunz
Michael Bauer
Andreas Baranyai
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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 Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Publication of EP1576037A1 publication Critical patent/EP1576037A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/14—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by electrical means
    • B05D3/141—Plasma treatment
    • B05D3/142—Pretreatment
    • B05D3/144—Pretreatment of polymeric substrates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
    • B05D3/065—After-treatment
    • B05D3/067—Curing or cross-linking the coating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/40—Distributing applied liquids or other fluent materials by members moving relatively to surface
    • B05D1/42—Distributing applied liquids or other fluent materials by members moving relatively to surface by non-rotary members
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00—Polymeric substrate or laminate
    • B05D2201/02—Polymeric substrate

Definitions

  • the invention relates to a method for producing a highly adhesive reactive coating on organic or inorganic substrates.
  • Plasma processes have been used for some time to produce reactive coatings on surfaces.
  • Plasma polymerization in particular is frequently used in this regard.
  • polymerizable precursors are fed to a low-pressure plasma via the gas phase and deposited on the surface in polymerized form.
  • Techniques used for this and the resulting surfaces and their use are described, for example, in "Plasma Surface Modification and Plasma Polymerization by N. Inagaki, Technomic Publishing Company Inc., Lancaster 1996”, “Plasma Polymerization by H. Yasuda, Academic Press Inc., New York 1985 "and” Plasma Polymerization Processes by H. Biederman, Y. Osada, Elsevier Science Publishers, Amsterdam 1992 ".
  • the above-mentioned plasma techniques require that they be carried out in a vacuum and thus require complex equipment and time-consuming procedures.
  • the compounds to be applied or polymerized (precursors) must be evaporated and evaporated condensed again to the substrate, which can lead to high thermal loads and in many cases to decomposition.
  • the evaporation and deposition rates are low, making it difficult and lengthy to produce layers with a sufficient thickness.
  • Solutions, suspensions or emulsions are applied to the inorganic or organic substrate, the activatable initiator and / or the ethylenically unsaturated compound being incorporated at least one group which interacts with a subsequently applied coating or reacts with groups contained therein, c) the coated substrate heated and / or irradiated with electromagnetic waves and forming an adhesion promoter layer, d) providing the substrate pretreated in this way with the further coating which contains reactive groups which react with those of the adhesion promoter layer and / or which interact with the adhesion promoter layer.
  • the activatable initiator is preferably a free radical initiator.
  • polymers of mono- and diolefins for example polypropylene, polyisobutylene, poly-butene-1, poly-4-methylpentene-1, polyisoprene or polybutadiene, and polymers of cycloolefins such as, for example, cyclopentene or norbornene; also polyethylene (which may or may not be crosslinked), e.g.
  • HDPE high density polyethylene
  • HDPE-HMW high density and high molecular weight polyethylene
  • HDPE-UHMW medium density polyethylene
  • MDPE polyethylene low density polyethylene
  • LDPE linear low density polyethylene
  • VLDPE VLDPE
  • ULDPE ultra high molecular weight polyethylene
  • copolymers of mono- and diolefins with one another or with other vinyl monomers such as, for example, ethylene-propylene copolymers, linear low-density polyethylene (LLDPE) and mixtures thereof with low-density polyethylene (LDPE), and terpolymers of ethylene with propylene and a diene, such as
  • Unsaturated polyester resins which are derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols, and vinyl compounds as crosslinking agents, as well as their halogen-containing, flame-retardant modifications;
  • crosslinkable acrylic resins derived from substituted acrylic acid esters, such as epoxy acrylates, urethane acrylates or polyester acrylates;
  • Crosslinked epoxy resins which are derived from aliphatic, cycloaliphatic, heterocyclic or aromatic glycidyl compounds, for example products of bisphenol A diglycidyl ether, bisphenol F diglycidyl ethers which are crosslinked by means of conventional hard materials such as anhydrides or amines with or without
  • He, argon, xenon, N2, 02, H2, water vapor or air can be used as the primary plasma gases.
  • the method according to the invention is in itself not sensitive to the coupling of the electrical energy.
  • the process can be carried out in batch operation, for example in a rotating drum, or in the case of films, fibers or fabrics in continuous operation. These methods are known and are described in the prior art.
  • the method can also be carried out under corona discharge conditions.
  • Corona discharges are generated under normal pressure conditions, with air being the most common ionized gas. In principle, however, other gases and mixtures are also possible, such as in COATING Vol. 2001, No. 12, 426, (2001).
  • the advantage of air as an ionizing gas in the case of corona discharges lies in the fact that work can be carried out in an apparatus which is open to the outside and, for example, a film can be drawn continuously between the discharge electrodes.
  • Such process arrangements are known and z. B. in J. Adhesion Sci. Technol. Vol 7, No. 10, 1105, (1993).
  • Three-dimensional workpieces can be treated with a plasma-free jet by tracing the contours with the help of robots.
  • the process can be carried out in a wide pressure range, the discharge characteristic shifting from pure low-temperature plasma towards corona discharge with increasing pressure and finally changing to a pure corona discharge at atmospheric pressure of approx. 1000-1100 m
  • the process is preferably carried out at a process pressure of 10-6 mbar up to atmospheric pressure (1013 mbar), particularly preferably at atmospheric pressure as a corona process.
  • a corona discharge is used, air, CO 2 and / or nitrogen is preferably used as the gas.
  • Preferred compounds are: dibenzoyl peroxide, benzoyl peroxide, dicumyl peroxide, cumyl hydroperoxide, diisopropyl peroxydicarbonate, methyl ethyl ketone, bis (4-t-butylcyclohexyl) peroxydicarbonate, Ammoniumperoxomonosulfat, ammonium peroxodisulfate, Dikaliumpersulfat, Dinatriumpersulfat, N, N-azobisisobutyronitrile, 2,2'-azobis (2,4 - dimethylpentanitrile), 2,2'-azobis (2-methylpropannitrile), 2,2'-azobis (2-methylbutanenitrile), 1, 1 '- azobis (cyanocyclohexane), tert-amylperoxobenzoate, 2,2'-bis (tert -butylperoxy) butane, 1,1 '- bis (tert-butylperoxy) cycl
  • Possible coinitiators are, for example, sensitizers which shift or broaden the spectral sensitivity and thereby accelerate the photopolymerization.
  • These are, in particular, aromatic carbonyl compounds such as, for example, benzophenone, thioxanthone, in particular also isopropylthioxanthone, anthraquinone and 3-acylcoumarin derivatives, triazines, coumarins, terphenyls, styryl ketones, and 3- (aroylmethylene) thiazolines, camphorquinone, but also eosine, Rhodamine and erythrosine dyes. Certitiators are also tert.
  • the ethylenically unsaturated compounds can contain one or more olefinic double bonds. They can be low molecular weight (monomeric) or higher molecular weight (oligomeric, polymeric). Through clever selection, the properties of the reactive layers can be controlled in a wide range.
  • acrylonitrile acrylamide, methacrylamide, N-substituted (meth) acrylic amides
  • vinyl esters such as vinyl acetate, vinyl ethers such as isobutyl vinyl ether, styrene, alkyl and halogenstyrenes
  • maleic acid or maleic anhydride N-vinyl pyrrolidone
  • vinyl chloride or vinylidene chloride N-vinyl pyrrolidone
  • unsaturated compounds which carry additional groups which react acidic, neutral or basic (e.g. allylamine, 2-aminoethyl methacrylate, 4-vinylpyridine, acrylic acid, 2-propene-1-sulfonic acid).
  • Examples of higher molecular weight (oligomeric, polymeric) polyunsaturated compounds are acrylated epoxy resins, acrylated polyesters, polyurethanes and polyethers containing vinyl ether or epoxy groups.
  • Further examples of unsaturated oligomers are unsaturated polyester resins, which are usually produced from maleic acid, phthalic acid and one or more diols and have molecular weights of approximately 500 to 3000.
  • vinyl ether monomers and oligomers as well as maleate-terminated oligomers with polyester, polyurethane, polyether, polyvinyl ether and epoxy main chains can also be used.
  • Combinations of oligomers and polymers bearing vinyl ether groups, as described in WO 90/01512 are particularly suitable.
  • Copolymers of vinyl ether and maleic acid functionalized monomers are also suitable.
  • Such unsaturated oligomers can also be referred to as prepolymers.
  • unsaturated carboxylic acids are acrylic acid, methacrylic acid, crotonic acid, itaconic acid, cinnamic acid, unsaturated fatty acids such as linolenic acid or oleic acid.
  • Acrylic and methacrylic acid are preferred.
  • cationically polymerizable formulations of epoxides and / or vinyl ethers which are started by photochemically and / or thermally activatable acid generators should be mentioned here.
  • an improved adhesion of the coating to the surfaces can also be achieved if these have previously been provided with OH groups, which can be achieved by using OH-functionalized initiators and / or unsaturated compounds in step b).
  • Anchored epoxy groups can also be reacted with amines and / or alcohols and / or phenols to form stable bonds.

Landscapes

  • Plasma & Fusion (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)

Abstract

L'invention concerne un procédé pour former des revêtements sur un substrat inorganique ou organique, ainsi que des substrats revêtus au moyen de ce procédé. Le procédé selon l'invention est caractérisé en ce qu'il consiste : a) à soumettre le substrat inorganique ou organique à un plasma basse température, une décharge par effet couronne, un rayonnement dur et/ou à un traitement à la flamme ; à appliquer sur ce substrat inorganique ou organique 1.) au moins un initiateur activable ou 2.) au moins un initiateur activable et au moins un composé éthyléniquement insaturé sous forme de masses fondues, solutions, suspensions ou émulsions, et à incorporer, dans l'initiateur activable et/ou le composé éthyléniquement insaturé, au moins un groupe qui interagit, de manière adhésive, avec un revêtement appliqué ultérieurement ou avec des groupes contenus dans celui-ci, ; c) à chauffer le substrat ainsi revêtu et/ou à l'irradier au moyen d'ondes électromagnétiques, et à former une couche adhésive ; d) à pourvoir le substrat ainsi prétraité d'un revêtement supplémentaire contenant des groupes réactifs qui réagissent avec les groupes de la couche adhésive et/ou interagissent avec cette couche adhésive.
EP03799570A 2002-12-20 2003-12-15 Procede de formation de revetements reactifs Withdrawn EP1576037A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10260336 2002-12-20
DE10260336 2002-12-20
PCT/EP2003/051010 WO2004056910A1 (fr) 2002-12-20 2003-12-15 Procede de formation de revetements reactifs

Publications (1)

Publication Number Publication Date
EP1576037A1 true EP1576037A1 (fr) 2005-09-21

Family

ID=32667530

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03799570A Withdrawn EP1576037A1 (fr) 2002-12-20 2003-12-15 Procede de formation de revetements reactifs

Country Status (13)

Country Link
US (1) US20060159856A1 (fr)
EP (1) EP1576037A1 (fr)
JP (1) JP2006510774A (fr)
KR (1) KR20050084451A (fr)
CN (1) CN1729237A (fr)
AU (1) AU2003299237A1 (fr)
BR (1) BR0317581A (fr)
CA (1) CA2510380A1 (fr)
MX (1) MXPA05006547A (fr)
RU (1) RU2338760C2 (fr)
TW (1) TW200422108A (fr)
WO (1) WO2004056910A1 (fr)
ZA (1) ZA200504341B (fr)

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WO2006067061A2 (fr) * 2004-12-22 2006-06-29 Ciba Specialty Chemicals Holding Inc. Procede permettant de produire des revetements fortement adherents
JP5013242B2 (ja) * 2005-04-25 2012-08-29 旭硝子株式会社 着色されたフッ素樹脂成形体
US20070036909A1 (en) * 2005-08-09 2007-02-15 Shifang Luo Processes for producing oriented polymeric films provided with UV-active coatings
JP5057201B2 (ja) * 2005-08-26 2012-10-24 旭硝子株式会社 機能性表面を有するフッ素樹脂成形体
DE102009001775A1 (de) * 2009-03-24 2010-09-30 Evonik Röhm Gmbh (Meth)acrylatpolymere und deren Verwendung als polymergebundene UV-Initiatoren oder Zusatz zu UV-härtbaren Harzen
GB2476976A (en) 2010-01-18 2011-07-20 Lintfield Ltd Protected aryl ketones and their use as photoinitiators
KR101757406B1 (ko) * 2010-03-26 2017-07-12 파우에스엘 인터나치오날 아게 향상된 가닥 안내 장치
WO2013015412A1 (fr) * 2011-07-28 2013-01-31 凸版印刷株式会社 Corps stratifié, film de barrière au gaz et procédé de production de corps stratifié et de film de barrière au gaz
FR2979214B1 (fr) * 2011-08-26 2014-04-25 Seb Sa Article comportant un revetement antiadhesif presentant des proprietes ameliorees d'adherence au support
DE102011113720A1 (de) 2011-09-17 2012-05-10 Daimler Ag Verfahren zum Verkleben eines Anbauteils mit einem korrespondierenden Halteteil eines Kraftwagens sowie Halteanordnung eines Anbauteils an einem korrespondierenden Halteteil eines Kraftwagens
EP3024902B1 (fr) 2013-07-22 2019-09-11 CeramTec-Etec GmbH Colle transparente ayant un indice de réfraction compris entre 1,7 et 1,73
RU2553852C2 (ru) * 2013-08-07 2015-06-20 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Казанский государственный архитектурно-строительный университет" КГАСУ Способ поверхностной обработки изделий из поливинилхлорида
ITUB20155236A1 (it) * 2015-10-30 2017-04-30 Univ Degli Studi Di Milano Bicocca Processo di rivestimento di substrati polimerici e carta.
DE102016220687A1 (de) 2016-10-21 2018-04-26 Tesa Se Plasmabehandlung einer Mehrlagenverklebung
GB201709352D0 (en) * 2017-06-13 2017-07-26 Henkel IP & Holding GmbH Activating surfaces for subsequent bonding
US11787911B2 (en) 2017-06-13 2023-10-17 Henkel Ag & Co. Kgaa Activating surfaces for subsequent bonding
CN108545963A (zh) * 2018-04-27 2018-09-18 成都市德工智动科技有限公司 一种玻璃瓶表面印花工艺
CN108660789A (zh) * 2018-06-06 2018-10-16 安徽华利达户外用品有限公司 一种户外用品用聚酰胺纤维染色的方法
GB2579608B (en) * 2018-12-06 2023-02-15 Henkel Ag & Co Kgaa Activating surfaces for subsequent bonding to another substrate
KR102193671B1 (ko) * 2019-03-19 2020-12-21 한국과학기술연구원 벤젠 고리를 가지는 화합물로 코팅된 탄소섬유의 급속 플라즈마 처리를 통한 표면 처리 방법 및 장치, 이에 따른 탄소 섬유의 물성 향상 방법 및 물성이 향상된 탄소 섬유
BE1027320B1 (nl) * 2019-05-28 2021-01-12 Sidec Nv Granulaat en bijhorend geur- en emissiearme coating in het bijzonder bouwelementcoating, bijvoorbeeld vloercoating, op basis van een radicalaire polymerisatie
CN111040437B (zh) * 2019-12-12 2022-11-22 株洲时代新材料科技股份有限公司 一种适用于高温高电压器件的改性尼龙及其制备方法
CN111705347B (zh) * 2020-06-05 2021-11-30 西北工业大学宁波研究院 一种化学气相沉积法制备钛纳米管碘涂层的方法及应用
US20230374238A1 (en) 2020-10-30 2023-11-23 Mercene Coatings Ab Coating and primer
CN114956655B (zh) * 2022-05-24 2023-03-24 浙江雅杰建材有限公司 一种水泥密封用稀土固化剂的制备方法
CN114892396B (zh) * 2022-06-20 2024-01-19 深圳市乐清合兴电子有限公司 一种导电性能良好的导电布及其制作方法

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Also Published As

Publication number Publication date
AU2003299237A1 (en) 2004-07-14
JP2006510774A (ja) 2006-03-30
MXPA05006547A (es) 2005-08-16
CA2510380A1 (fr) 2004-07-06
KR20050084451A (ko) 2005-08-26
RU2338760C2 (ru) 2008-11-20
BR0317581A (pt) 2005-11-22
RU2005122900A (ru) 2006-08-10
US20060159856A1 (en) 2006-07-20
ZA200504341B (en) 2006-07-26
WO2004056910A1 (fr) 2004-07-08
CN1729237A (zh) 2006-02-01
TW200422108A (en) 2004-11-01

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