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WO 2017/147061 Al 31 August 2017 (31.08.2017) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/147061 Al 31 August 2017 (31.08.2017) P O P C T (51) International Patent Classification: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, C09J 183/04 (2006.0 1) C08L 83/04 (2006.0 1) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, (21) International Application Number: KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, PCT/US20 17/0 18687 MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, (22) International Filing Date: NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, 2 1 February 2017 (21 .02.2017) RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, (25) Filing Language: English ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every (30) Priority Data: kind of regional protection available): ARIPO (BW, GH, 62/298,499 2 3 February 2016 (23.02.2016) U S GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: DOW CORNING CORPORATION TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, [US/US]; 2200 West Salzburg Road, Midland, Michigan DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, 48686 (US). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (72) Inventors: BEYER, Patrick; Pfarrer-Veller-Strasse 12, GW, KM, ML, MR, NE, SN, TD, TG). 55 128 Mainz (DE). DINNINGER, Chad; 1045 1 Marion Road, Saint Charles, Michigan 48655 (US). GIBAS, Ro¬ Declarations under Rule 4.17 : ger; 702 McCormick Street, Bay City, Michigan 48708- — as to applicant's entitlement to apply for and be granted a 7739 (US). KENNAN, John; 6124 Londonberrie Court, patent (Rule 4.1 7(H)) Midland, Michigan 48640 (US). WOLF, Hans Peter; Taunusblick 18, 65835 Liederbach (DE). — as to the applicant's entitlement to claim the priority of the earlier application (Rule 4.1 7(in)) (74) Agents: ISTVAN-MITCHELL, Wyatt et al; 900 Fifth Third Center, 111 Lyon Street NW, Grand Rapids, — of inventorship (Rule 4.17(iv)) Michigan 49503 (US). Published: (81) Designated States (unless otherwise indicated, for every — with international search report (Art. 21(3)) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, © (54) Title: SELECTIVE ADHESION SILICONE RUBBER (57) Abstract: The present invention relates to selective adhesion liquid silicone rubber composition comprising an organopoly¬ siloxane (A) containing at least 2 alkenyl groups bonded to silicon atom per molecule, an organopolysiloxane (B) containing at least 2 silicon-bonded hydrogen atom per molecule comprising organopolysiloxane (Bl) and organopolysiloxane (B2), wherein organo ¬ polysiloxane (Bl) contains siloxy units of the type (R HSiOi/ )x where R is independently selected from hydrogen, aliphatic hydro¬ o 2 2 carbyl, aromatic hydrocarbyl, or organyl group and x > 2 ; and organopolysiloxane (B2) contains siloxy units of the type (RHSiO 2/2) where R is independently selected from hydrogen, aliphatic hydrocarbyl, aromatic hydrocarbyl, or organyl group and z > 2 , a platin¬ um based catalyst (C), an inhibitor (D), selected from the group consisting of acetylenic alcohols and their derivatives, a silica filler (E) and an adhesion promoter (F). SELECTIVE ADHESION SILICONE RUBBER [0001] The present invention relates to a selective adhesion liquid silicone elastomer compositions which can cure at temperatures < 140°C. Also included is a process for preparing cured silicone elastomer and articles and composite parts made from said selective adhesion liquid silicone elastomer compositions. [0002] Liquid curable silicone elastomer compositions typically cure or react to provide for cured silicone elastomers, also known as silicone rubbers. The terms silicone elastomer and silicone rubber are typically used interchangeably. Liquid curable silicone elastomer compositions include platinum cured silicone elastomers (addition reaction, otherwise known as hydrosilylation). [0003] Organopolysiloxanes may generally be described as polymers having multiple units of the formula (I): RaSiO(4 - a) 2 (I) in which R is independently selected from hydrogen, aliphatic hydrocarbyl, aromatic hydrocarbyl, or organyl group (that is any organic substituent group, regardless of functional type, having one free valence at a carbon atom). Saturated aliphatic hydrocarbyls are exemplified by, but not limited to alkyl groups such as methyl, ethyl, propyl, pentyl, octyl, undecyl, and octadecyl and cycloalkyl groups such as cyclohexyl. Unsaturated aliphatic hydrocarbyls are exemplified by, but not limited to, alkenyl groups such as vinyl, allyl, butenyl, pentenyl, cyclohexenyl and hexenyl; and by alkynyl groups. Aromatic hydrocarbon groups are exemplified by, but not limited to, phenyl, tolyl, xylyl, benzyl, styryl, and 2-phenylethyl. Organyl groups are exemplified by, but not limited to, halogenated alkyl groups such as chloromethyl, 3-chloropropyl, and 3,3,3-trifluoropropyl; nitrogen containing groups such as amino groups, amido groups, imino groups, imido groups; oxygen containing groups such as polyoxyalkylene groups, carbonyl groups, alkoxy groups and hydroxyl groups. Further organyl groups may include sulfur containing groups, fluor containing groups, phosphorus containing groups, boron containing groups. The subscript "a" is an integer of from 0 to 3 . [0004] Siloxy units may be described by a shorthand (abbreviated) nomenclature, namely - "M," "D," "T," and "Q," when R is a methyl group (further teaching on silicone nomenclature may be found in Walter Noll, Chemistry and Technology of Silicones, dated 1962, Chapter I, pages 1-9). The M unit corresponds to a siloxy unit where a = 3, that is R Si0 ; the D 3 2 unit corresponds to a siloxy unit where a = 2, namely R2Si0 2 /2; the T unit corresponds to a siloxy unit where a = 1, namely R iO ; and the Q unit corresponds to a siloxy unit where a = 0, namely Si0 4 2 . [0005] In some instances, the silicone elastomer may be overmoulded onto other parts made of different or same materials or may be coated on textile or fabric. For example, a silicone surface may be overmoulded onto a polyethylene telephone housing, or a polyurethane automobile dashboard. Further examples include an airbag fabric coated with a silicone elastomer. [0006] Selective adhesion liquid silicone rubber (also referred to as "SA LSR") refers to liquid silicone elastomer products that incorporate some level or form of adhesion promoter to build unprimed (or primer free) adhesion to a first type of substrate while exhibiting minimal adhesion to a second type of substrate, thereby the "selective" adhesion qualification. The first type of substrate may include plastic substrates, while the second type of substrate may include metal substrates such as those surfaces of the moulds used to shape silicone rubber products. The adhesion is spontaneously developed during the curing process, without the need to rely on a primer material. [0007] Examples of such SA LSR include those disclosed in US4677161 where the adhesion promoter is a polysiloxane comprising diorganohydrogensiloxy, alkoxy and Si0 4 2 units; and those disclosed in US4906686 where the adhesion promoter is a mixture, or reaction product, of (a) a silicon-free compound which contains at least 1 alcoholic hydroxyl group and at least 1 alkenyl group in each molecule, and (b) an organosilane having in each molecule at least 1 alkoxy group and at least 1 epoxy or methacryloxy or acryloxy group. [0008] US6663967 discloses a curable organopolysiloxane polymer system having selective adhesion to a substrate, said system containing the following components: (A) an organopolysiloxane polymer; (B) an organohydrogenpolysiloxane crosslinker; (C) a platinum group metal catalyst; (D) a cure inhibitor; (E) an adhesion promoter; (F) an epoxy functional compound; and (G) a trialkyl end blocked polysiloxane, where the platinum group metal catalyst is a neutralized complex of chloroplatinic acid or platinum dichloride with symdivinyltetramethyldisiloxane. The composition selectively adheres to a substrate that may be a thermoset or a thermoplastic, but not to a metal such as aluminum or steel. [0009] US201 4/01 79863 relates to an addition curable silicone rubber composition having self-adhesiveness which is capable of adhering to organic resins such as polyamide, polybuthylene terephthalate (PBT), polycarbonate, polyphenylene oxide, and polyphenylene sulfide. The addition curable self-adhesive silicone rubber composition can be moulded at a relatively low temperature in a short time and has sufficient pot life for working without sacrificing its rapid curability at low temperature. [0010] US4087585 discloses that hydroxylated, vinyl-containing polysiloxane and epoxy- containing silanes can be used to provide silicone compositions which, when cured in contact with substrates, exhibit adhesion properties. [001 1] SA LSRs typically allow fabricators to adhere silicone to plastic substrates by simply injection moulding the silicone onto the surface of the plastic substrate. The use of an SA LSR avoids the need for applying an adhesive primer and costly manual assembly steps. Further, binding directly to the plastic substrate eliminates gaps between
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