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WO2000000355A1 - Production de pieces moulees en silicone, imprimees resistant a l'usure - Google Patents

Production de pieces moulees en silicone, imprimees resistant a l'usure Download PDF

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Publication number
WO2000000355A1
WO2000000355A1 PCT/EP1999/004362 EP9904362W WO0000355A1 WO 2000000355 A1 WO2000000355 A1 WO 2000000355A1 EP 9904362 W EP9904362 W EP 9904362W WO 0000355 A1 WO0000355 A1 WO 0000355A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
abrasion
printing
printing paste
average
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/EP1999/004362
Other languages
German (de)
English (en)
Inventor
Thomas Naumann
Stephan Kirchmeyer
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.)
Momentive Performance Materials GmbH
Original Assignee
GE Bayer Silicones GmbH and Co KG
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 GE Bayer Silicones GmbH and Co KG filed Critical GE Bayer Silicones GmbH and Co KG
Publication of WO2000000355A1 publication Critical patent/WO2000000355A1/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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
    • B29C59/005—Surface shaping of articles, e.g. embossing; Apparatus therefor characterised by the choice of material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M1/00—Inking and printing with a printer's forme
    • B41M1/26—Printing on other surfaces than ordinary paper
    • B41M1/30—Printing on other surfaces than ordinary paper on organic plastics, horn or similar materials
    • B41M1/305—Printing on other surfaces than ordinary paper on organic plastics, horn or similar materials using mechanical, physical or chemical means, e.g. corona discharge, etching or organic solvents, to improve ink retention

Definitions

  • the present invention relates to a method for producing abrasion-resistant printed silicone molded parts and the silicone molded parts obtainable by this method.
  • silicone moldings such.
  • B. Switch and keyboard mats which have been printed with printing pastes based on silicone rubber, have a low abrasion resistance.
  • so-called top coats based on silicone rubbers, polyurethanes or other organic binders are often applied by spraying and hardened by thermal treatment.
  • the main disadvantage of the spraying process is that only small parts of the topcoat get to the desired location during application and large parts are lost as so-called overspray. This is undesirable for cost reasons.
  • the spraying process has the disadvantage that it can only be automated in a very complex and costly manner.
  • the invention therefore relates to a method for producing abrasion-resistant printed silicone molded parts, a printing paste based on polyurethanes being printed on a silicone molded part after surface activation, and the molded part then being thermally treated.
  • silicone moldings are e.g. B. producible from compositions containing as base polymers polyorganosiloxanes, preferably polydiorganosiloxanes such as polydimethyl and polydiphenylsiloxanes, and additionally have accessible groups for crosslinking reactions. Such groups are predominantly H atoms, hydroxyl and vinyl groups, which can be located at the chain ends, but can also be incorporated into the chain.
  • the masses often contain fillers and reinforcing materials such.
  • Further additives are preferably crosslinking catalysts such as organic peroxides and metal compounds (for example platinum compounds such as hexachloroplatinic acid or tin compounds such as dibutyltin dilaurate), anti-aging agents, bactericides, fungicides, processing aids such as lubricants, inorganic and organic pigments.
  • crosslinking catalysts such as organic peroxides and metal compounds (for example platinum compounds such as hexachloroplatinic acid or tin compounds such as dibutyltin dilaurate), anti-aging agents, bactericides, fungicides, processing aids such as lubricants, inorganic and organic pigments.
  • the silicone moldings are usually made from the masses by methods known to those skilled in the art by heating in suitable devices, for. B. heated molds, injection molding machines or extruders.
  • the silicone moldings which can be used in the process according to the invention can be surface-modified, for example by applying coatings or printing on the basis of silicones.
  • the materials or coatings on which the coatings are based are in principle the same as those on which the moldings are based. You can colorants and additional tools such.
  • alcohols such as methanol, ethanol, n-propanol, isopropanol and butanol, ketones such as acetone and butanone, esters such as butyl acetate and methoxypropyl acetate, aromatic solvents such as toluene and xylene and aliphatic solvents such as hexane and white spirit.
  • the first step in the process mainly serves to increase the surface roughness of the silicone molded part - and thus also the binding force between the silicone molded part and the printing paste.
  • the activation can e.g. B. by treatment with solvents; Treatment with alkaline solutions such as B. sodium or potassium hydroxide in water or suitable organic solvents; Treatment with oxidizing agents; mechanical roughening z. B. by grinding; and treatment with flame, plasma or corona discharges.
  • Preferred surface activation methods are treatment with flames (gas flames) and corona discharges.
  • Printing pastes based on polyurethanes in the sense of the invention are printing pastes which contain, in addition to hydroxyl-functional components, isocyanate-functional components. By reacting the hydroxyl groups with the isocyanate groups, urethane groups are formed.
  • Printing pastes based on polyurethanes are preferably crosslinking compositions
  • Mn average molecular weight
  • the polyols a) used in the printing paste based on polyurethanes have an average molecular weight (Mn) of 200 to 5000, preferably 500 to 2000 and on average at least 2 hydroxyl groups per molecule.
  • the average molecular weight can be determined by means of gel permeation or particle exclusion chromatography. graph can be determined.
  • Preferred polyols are hydroxyl-containing polyesters, polyethers, polycarbonates, polyester amides, polyacrylates and Polyacrylate polyols used. Polybutadienes containing hydroxyl groups are also suitable.
  • Suitable polyesters are e.g. B. the reaction products of polyhydric, preferably dihydric alcohols, which may optionally additionally contain trihydric alcohols, with polyhydric, preferably dihydric carboxylic acids or their esterifiable derivatives.
  • the polycarboxylic acids can be aliphatic, cycloaliphatic, aromatic and / or heterocyclic in nature and they can be substituted by halogen atoms and / or unsaturated.
  • carboxylic acids and their derivatives are succinic acid, adipic acid, phthalic acid, isophthalic acid, phthalic anhydride, anhydride tetrahydrophthalic anhydride, hexahydrophthalic anhydride, Terachlorphthal Acidanhydrid, ene domethylentetrahydrophthalcic Acidanhydrid, maleic acid, maleic anhydride, marklare fu, dimerized and trime catalyzed unsaturated fatty acids (optionally in admixture with monomeric unsaturated fatty acids) called dimethyl terephthalate and bisglycol terephthalate.
  • Suitable polyhydric alcohols are e.g. B. ethylene glycol, 1, 2- and 1, 3-propanediol, 1, 4- and 2,3-butanediol, 1, 6-hexanediol, 1, 8-octanediol, 2,2-dimethyl-1, 3-propanediol, 1st , 4-bis (hydroxymethyl) cyclohexane, 1, 1, 1-T ⁇ ' s- (hydroxymethyl) propane, 1, 1, 1-tris (hydroxymethyl) ethane, di-, tri-, tetra- and higher polyethylene glycols, di - and higher polypropylene glycols and di- and higher polybutylene glycols. Lactone polyester, e.g. B.
  • ⁇ -caprolactone or from hydroxycarboxylic acids, e.g. B. ⁇ -hydroxycaproic acid can be used.
  • hydroxycarboxylic acids e.g. B. ⁇ -hydroxycaproic acid
  • the hydroxyl-functional polyesters known from oleochemistry, such as, for. B. castor oil and its transesterification products can be used.
  • Suitable polyethers can e.g. B. by polymerization of epoxides (such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide or epichlorohydrin) or of tetrahydrofuran with itself, preferably in the presence of Lewis catalysts such as Boron trifluoride.
  • Suitable polyethers can furthermore be obtained by addition of the epoxides mentioned, preferably of ethylene oxide and propylene oxide, optionally in a mixture or in succession, to starting components with compounds containing reactive hydrogen atoms, such as water, alcohols, ammonia or amines, for. B. ethylene glycol, 1, 2- or 1, 3-propanediol, water, 4,4'-dihydroxydiphenylpropane, aniline, ethanolamine or ethylenediamine.
  • epoxides such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide or epichlorohydrin
  • the polycarbonates containing hydroxyl groups are those which are known in the art, for. B. by reacting the above-mentioned diols, in particular 1,3-propanediol, 1,4-butanediol and / or 1,6-hexanediol, diethylene glycol, triethylene glycol, tetraethylene glycol or thiodiglycol, with diaryl carbonates, e.g. B. diphenyl carbonate, or phosgene can be produced.
  • Suitable polyester amides and polyamides are e.g. B. the predominantly linear condensates obtained from polyvalent saturated or unsaturated carboxylic acids or their anhydrides and polyvalent saturated or unsaturated amino alcohols, diamines, polyamines and mixtures thereof.
  • Polyacrylates suitable for the present invention are polymers of compounds having ethylenically unsaturated groups, preferably esters of acrylic acid and methacrylic acid, eg. B. methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate and hexyl acrylate or methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate and hexyl methacrylate.
  • Other compounds containing ethylenically unsaturated groups are e.g. B. styrene, acrylonitrile, acrylamide,
  • Methacrylamide acrylic acid, methacrylic acid, esters of maleic acid and fumaric acid such as.
  • the polyacrylate polyols for the purposes of the present invention are hydroxyl-bearing, ethylenically unsaturated group-containing compounds (the ethylenically unsaturated groups as defined above), in particular hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxylethyl methacrylate and hydroxypropyl methacrylate.
  • polyacrylate polyols by etherification, for. B. with ethylene oxide or propylene oxide, or esterification, for. B. with caprolactone to further modify.
  • the compounds have an average molecular weight (Mn) of 200 to 5000 and at least 2 hydroxyl groups per molecule.
  • Particularly preferred polyols for printing paste based on polyurethanes are polyester polyols which have an average molecular weight between 500 and 2000 and 2 to 7 hydroxyl groups per molecule.
  • polyisocyanates b aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic polyisocyanates or any mixtures of these polyisocyanates can be used, as described, for. B. in Houben-Weyl "Methods of Organic Chemistry", Volume E20 “Macromolecular Substances”, editor H. Bartl, J. Falbe, Georg Thieme Verlag, Stuttgart, New York, 1987, pp. 1587-1593 . These are e.g. B.
  • ethylene diisocyanate 1, 4-tetramethylene diisocyanate, 1, 6-hexamethylene diisocyanate, 1, 12-dodecane diisocyanate, cyclobutane-1, 3-diisocyanate, cyclohexane-1, 3- and -1, 4-diisocyanate and any mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4- and 2,6-hexahydro-toluenediisocyanate and any mixtures of these isomers, hexahydro-1, 3 and / or -1, 4th -phenylene diisocyanate, perhydro-2,4'- and / or -4,4'-diphenylmethane diisocyanate, norbomane diisocyanates (e.g.
  • Modification products from the aforementioned isocyanates are also suitable.
  • “modification” is understood to mean the production of derivatives of simple polyisocyanates, in particular diisocyanates, containing derivatives of uretane, allophanate, uretdione and / or isocyanurate groups.
  • Suitable modifiable diisocyanates are, for example Hexamethylene diisocyanate, cyclohexane-1, 3- and -1, 4-diisocyanate and any mixtures of these isomers, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 2,4- and 2,6-hexahydro toluenediisocyanate and any mixtures of these isomers, perhydro-2,4'- and / or -4,4'-diphenylmethane diisocyanate, 2,4- and 2,6-tolylene diisocynanate as well as any mixtures of these isomers, diphenylmethane-2,4'- and / or - 4,4'-diisocyanate and naphthylene-1, 5-diisocyanate
  • the monoisocyanates which may be used include 1-isocyanatohexane, 1-isocyanatoctadecan
  • Particularly preferred modifiable diisocyanates are the technically important polyisocyanates such as 2,4-diisocyanatotoluene; whose technical mixtures with up to 35 wt .-%, based on the mixture, of 2,6-diisocyanatotoluene; 4,4'-diisocyanatodiphenylmethane, its technical mixtures with 2,4'- and 2,2'-diisocyanatodiphenylmethane; 1,6-diisocynatohexane; 1,4-diisocyanatobutane; 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane; 1-Isocyanato-3 (4) -isocyanatomethyl-1 - methylcyclohexane or mixtures of these diisocyanates.
  • 2,4-diisocyanatototoluene whose technical mixtures with up to 35
  • isocyanates based on hexamethylene diisocyanate and isophorone diisocyanate modified by trimerization, biurization and allophanatization are very particularly preferred.
  • the quantitative ratios of polyols a) to polyisocyanates b) are preferably chosen so that 0.8 to 3.0, preferably 1.0 to 1.5, isocyanate groups of the polyisocyanate component fall per hydroxyl group of the polyol component.
  • Organic solvents d) can be present in the printing paste in an amount of up to 50% by weight, preferably from 0 to 2.5% by weight. The viscosity of the printing pastes is adjusted on the one hand and the miscibility of the individual components is improved on the other hand.
  • Suitable organic solvents are those solvents or solvent mixtures which contain no groups (such as hydroxyl, amino and carboxylic acid groups) which can react with isocyanate groups of the polyisocyanates b).
  • Suitable solvents or solvent mixtures in the sense of the invention are, for. B. acetone, 2-butanone, cyclohexanone, isobutyl methyl ketone, tetrahydrofuran, methyl acetate, ethyl acetate, butyl acetate, acetonitrile, chlorobenzene, chloroform, dichloromethane, perchlorethylene, carbon tetrachloride, trichlorethylene, trichloroethane, dichlorobenzene, dimethylformamide, dimethylformamide pyrrolidone, dimethylacetamide, dimethyl sulfoxide, dioxane, hexane, heptane, isooctane, ligroin, washing, soldering, light, varnish or test gasoline, petroleum ether, petroleum, turpentine oil substitute, cyclohexane, toluene, xylene, aliphatic or aromatic paint solvent mixture
  • Toluene, xylene, butyl acetate and methoxypropyl acetate are preferred.
  • Matting agents c) for the purposes of the invention are particulate agents which are suitable for changing the gloss of the printing pastes, such as natural inorganic agents (for example talc and silica) or organic agents (for example polyolefin waxes). Matting agents can be present in the printing paste in an amount of up to 5% by weight, preferably 0.1 to 2% by weight.
  • the printing pastes which can be used in the process according to the invention can contain up to 5% by weight, preferably from 0.1 to 2% by weight, of conventional auxiliaries e).
  • the tools within the meaning of the invention are, for. B. catalysts (such as catalysts which catalyze the reaction between polyisocyanates and polyols), additives which improve the adhesion of the printing paste, such as silanes (e.g. amino, epoxy, (meth) acrylate, Hydroxyl-, carboxyl- and thio-functional alkoxysiiane), surface-active additives, colorants, leveling agents, wetting agents, dispersing agents, stabilizers against aging and weathering, plasticizers, fungistatic and bacteriostatic substances and fillers.
  • silanes e.g. amino, epoxy, (meth) acrylate, Hydroxyl-, carboxyl- and thio-functional alkoxysiiane
  • surface-active additives e.g. amino, epoxy
  • Catalysts which catalyze the reaction between the polyisocyanate and the polyol are.
  • the catalysts mentioned can also be used as mixtures. Further representatives of usable catalysts as well as the details of the mode of action of the catalysts are in the plastics handbook, volume VII, edited by Vieweg and Höchtlen, Carl-Hanser-Verlag, Kunststoff, 1966, e.g. B. on pages 96 to 102.
  • the colorants in the sense of the invention are organic or inorganic dyes and pigments such as azo, anthraquinone, thioindigo or other polycyclic organic pigments, carbon black, titanium dioxide, zinc sulfide, ultramarine, iron oxide, nickel or chromium antimony dioxide, cobalt blue, chromium oxide and Chromate pigments.
  • the printing pastes which can be used in the process according to the invention preferably contain carbon black and no colorants.
  • all printing processes are suitable for applying the printing pastes to the silicone moldings in the process according to the invention.
  • the screen printing method and the pad printing method described in DE 36 36 962 are preferably used.
  • the thermal treatment is expediently carried out directly after the printing and serves to dry and crosslink the applied printing pastes.
  • the thermal treatment can e.g. B. by heating the molded body to 50 to 200 ° C, preferably 70 to 150 ° C, in an oven or by irradiation with suitable lamps such as infrared radiators.
  • the thermal treatment can also be carried out at temperatures lower than 50 ° C. if the printing pastes based on polyurethanes have suitable high crosslinking speeds for this.
  • the use of printing pastes with high crosslinking speeds is not preferred since these usually have short processing times at processing temperature.
  • the layer thickness of the applied printing paste after the thermal treatment is preferably 5 to 20 ⁇ m.
  • Another object of the invention are abrasion-resistant printed silicone molded parts obtainable by the process according to the invention.
  • Blank sample A plate with the dimensions 50 x 50 x 2 mm made of addition-crosslinked silicone rubber was coated with a commercially available black printing ink based on addition-crosslinking silicone rubber using a tampon printer (type Hermetic 61, available from Tampophnt) with a print image test area of 5 x Printed 10 mm three times in succession, wet on wet and then crosslinked with hot air at 180 ° C for 10 minutes.
  • a tampon printer type Hermetic 61, available from Tampophnt
  • the printed surface of a blank was subjected to a corona treatment (type CG06 from Arcotec, activation ten times with a rolling speed of 100 mm / s, setting 10 kV, 300 watts).
  • a corona treatment type CG06 from Arcotec, activation ten times with a rolling speed of 100 mm / s, setting 10 kV, 300 watts.
  • the printing ink from Example 2 was made using the tampon printer from Example 1 applied three times in succession, wet in wet and then crosslinked with hot air at 80 ° C. for 60 minutes.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Plasma & Fusion (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne un procédé permettant de produire des pièces moulées en silicone, imprimées résistant à l'usure, ainsi que des pièces moulées en silicone obtenues à l'aide dudit procédé.
PCT/EP1999/004362 1998-06-27 1999-06-23 Production de pieces moulees en silicone, imprimees resistant a l'usure Ceased WO2000000355A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19828639.2 1998-06-27
DE19828639A DE19828639A1 (de) 1998-06-27 1998-06-27 Herstellung abriebfester, bedruckter Siliconformteile

Publications (1)

Publication Number Publication Date
WO2000000355A1 true WO2000000355A1 (fr) 2000-01-06

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Application Number Title Priority Date Filing Date
PCT/EP1999/004362 Ceased WO2000000355A1 (fr) 1998-06-27 1999-06-23 Production de pieces moulees en silicone, imprimees resistant a l'usure

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DE (1) DE19828639A1 (fr)
WO (1) WO2000000355A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2701889A4 (fr) * 2011-04-26 2014-12-10 Aortech Internat Plc Procédé de liaison

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
US7469905B2 (en) 2000-11-30 2008-12-30 Springseal Inc. Permanently lubricated film gasket and method of manufacture

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JPS5867302A (ja) * 1981-10-19 1983-04-21 Shin Etsu Polymer Co Ltd ガス交換膜
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2701889A4 (fr) * 2011-04-26 2014-12-10 Aortech Internat Plc Procédé de liaison
US9216558B2 (en) 2011-04-26 2015-12-22 Aortech International Plc Bonding process
US9421737B2 (en) 2011-04-26 2016-08-23 Aortech International Plc Bonding process
US9809016B2 (en) 2011-04-26 2017-11-07 Aortech International Plc Bonding process
US10195834B2 (en) 2011-04-26 2019-02-05 Aortech International Plc Bonding process

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Publication number Publication date
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