EP2885352A1 - Compositions d'organosiloxane réticulant à l'ambiante - Google Patents

Compositions d'organosiloxane réticulant à l'ambiante

Info

Publication number
EP2885352A1
EP2885352A1 EP13745382.5A EP13745382A EP2885352A1 EP 2885352 A1 EP2885352 A1 EP 2885352A1 EP 13745382 A EP13745382 A EP 13745382A EP 2885352 A1 EP2885352 A1 EP 2885352A1
Authority
EP
European Patent Office
Prior art keywords
radicals
weight
composition
radical
rtv
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Withdrawn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
EP13745382.5A
Other languages
German (de)
English (en)
Inventor
Torsten Sixt
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.)
Wacker Chemie AG
Original Assignee
Wacker Chemie 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 Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP2885352A1 publication Critical patent/EP2885352A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C08G77/08—Preparatory processes characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • 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
    • C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/08—Crosslinking by silane

Definitions

  • Two-component (2K) silicone compositions have long been known in the art and are often used as adhesives and sealants in a variety of applications. at
  • Room temperature crosslinking two part silicones are referred to as "room temperature vulcanizing 2 part silicones" (RTV-2)
  • Polymer composition or referred to as A component.
  • the second component is often called hardener composition or B component.
  • tin catalysts are used because they allow an acceptable cure rate.
  • Organotin compounds are now classified as hazardous substances and thus also hardener composition containing organotin compounds.
  • Organotin compounds by legal regulations such as the EU Directive 76/769 / EEC more and more
  • Organotitanium compounds also show the known disadvantages of Ti, such as yellowing, surface tack and also too slow
  • Titanium catalysts in two-component polycondensation compositions based on OH-functional polymers because of the immediate
  • Facade elements can optionally have more
  • US Pat. No. 6,753,400 B2 also discloses room-temperature curing compositions comprising hydroxy-polydimethylsiloxane polymer, crosslinker and, as catalyst, bi-carboxylate.
  • these have an uneven depth hardening.
  • Desiccant / water traps contain a better
  • the molecular sieve used there dried serves to adsorb moisture from the formulation components as well as the diffusion-induced moisture access through the
  • the Molesieb is pre-dried to dryness substantially by anhydrous by heating to 100-500 ° C is made.
  • Layer thicknesses> 5mm is not sufficiently good with such formulations: it is to observe a considerable hardness gradient from outside to inside, up to missing vulcanization in the
  • the object of the present invention was therefore the
  • the polymer composition (II) contains at least 0.2% by weight of an adsorbent (C) selected from the group consisting of moisture-saturated molecular sieves characterized by containing not more than 10% by weight of their own weight in water can.
  • C an adsorbent
  • the determination of the water absorption of (C) is carried out by measuring the relative increase in weight under standard conditions, ie at 20 ° C and 50% relative humidity, within a period of 12 hours.
  • the crosslinkers (A) used in the hardener compositions (1) according to the invention are preferably organosilicon compounds of the general formula (1)
  • R 2 are the same or different independently of one another
  • Nitrogen atoms can be interrupted, means
  • Z independently of one another may be identical or different and is hydrolyzable radicals and
  • c 3 or 4
  • the partial hydrolysates may be any suitable partial hydrolysates.
  • Partial homohydrolysates i. Partial hydrolysates of one type of organosilicon compound of general formula (1), as well as partial co-hydrolysates, i. Partial hydrolysates of at least two different types of organosilicon compounds of the general formula (1).
  • These crosslinkers or partial hydrolysates according to the invention have a maximum weight average Mw of 1,200 g / mol (SEC versus polystyrene standard).
  • organosilicon compounds used according to the invention
  • Organosilicon compounds of the formula (1) such are those with up to 10 silicon atoms are preferred.
  • the radical R 2 is preferably monovalent
  • Hydrocarbon radicals having 1 to 18 carbon atoms which are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups or (poly) glycol radicals, the latter being
  • Oxyethylene and / or oxypropylene units are constructed, particularly preferably to alkyl radicals having 1 to 12
  • radical R 2 may also be divalent radicals which, for example, link together two silyl groups.
  • radicals R 2 are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert.
  • Cycloheptyl radical and methylcyclohexyl radicals include alkenyl radicals such as the vinyl, 1-propenyl and 2-propenyl radicals; Aryl radicals, such as the phenyl, naphthyl, anthryl and phenanthryl radicals;
  • Alkaryl radicals such as o-, m-, p-tolyl radicals; Xylyl residues and
  • Ethylphenyl radicals and aralkyl radicals, such as the benzyl radical, the ⁇ - and the ⁇ -phenylethyl radical.
  • substituted radicals R 2 are methoxyethyl,
  • divalent radicals R 2 are polyisobutylenediyl radicals and propanediyl-terminated polypropylene glycol residues.
  • radical R 2 are hydrocarbon radicals having 1 to 12
  • Carbon atoms are preferred and the methyl and the vinyl radical particularly preferred.
  • Z are all hydrolyzable radicals known hitherto, e.g. via oxygen atom or nitrogen atom bonded to silicon atom, optionally substituted
  • Radical Z is preferably radical -OR 1 , where R 1 is substituted or unsubstituted hydrocarbon radicals which may be interrupted by oxygen atoms.
  • Z examples are methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, tert-butoxy and 2-methoxyethoxy, amino radicals, such as methylamino , Dimethylamino, ethylamino, diethylamino, dipropylamino, dibutylamino and cyclohexylamino radical, amido radicals, such as N-methylacetamido and benzamido radicals, aminoxy radicals, such as the diethylaminoxy radical,
  • amino radicals such as methylamino , Dimethylamino, ethylamino, diethylamino, dipropylamino, dibutylamino and cyclohexylamino radical
  • amido radicals such as N-methylacetamido and benzamido radicals
  • aminoxy radicals such as the diethyla
  • Oxime radicals such as dimethylketoximo, methylethylketoximo and methylisobutylketoximo radical
  • enoxy radicals such as the 2-propenoxy radical
  • acyloxy radicals for example acetyl groups.
  • the crosslinkers (A) used in the compositions according to the invention are tetramethoxysilane,
  • crosslinkers (A) used in the hardener compositions (I) according to the invention are commercially available products or can be prepared by processes known in silicon chemistry
  • crosslinkers (A) according to the invention are used in amounts such that at least two-fold molar
  • Crosslinker functions based on the end group content of the components to be crosslinked.
  • a molar ratio of crosslinker functions to be crosslinked is preferably, a molar ratio of crosslinker functions to be crosslinked
  • Suitable catalysts (B) according to the invention are Bi compounds. Particular preference is given to bi-carboxylates or
  • Carboxylic acid salts between 2 and 20 carbon units
  • the hardener compositions (I) according to the invention comprise catalyst (B) in the amounts customary for the condensation reaction.
  • catalyst (B) in the range from 200 to 2500 ppm, in each case based on the metal and the
  • the hardness compositions (I) according to the invention may contain adhesion promoters (D) as further component. They are considered to be functional silanes or coupling agents.
  • adhesion promoters (D) used in the compositions according to the invention are silanes and organopolysiloxanes having functional groups, for example those having glycidoxy, amino or methacryloxy radicals. Furthermore, adhesion promoters (D) can also be silanes with hydrolyzable groups and SiC-bonded vinyl, acryloxy, methacryloxy, epoxy,
  • Acid anhydride, acid, ester, cyanurato, carbamato or ureidofunktionelle or ether groups and their partial and mixed hydrolysates can be used.
  • Preferred adhesion promoters are amino-, acrylic-, epoxy-, cyanurato-, carbamato- or ureido-functional silanes with hydrolyzable groups and their partial hydrolysates.
  • Preference is given to (D) in amounts such that 100 parts by weight of the catalyzed, ready-to-use RTV-2 composition ( hardness composition (I) + polymer composition (II)) have a content of
  • the hardener composition (I) may have more
  • ingredients (E) which have long been known in the art, included.
  • fillers such as reinforcing and non-reinforcing fillers other than (C) such as silicic acid, carbon black, quartz, chalk, diatomaceous earth, plasticizers, soluble dyes, inorganic and organic pigments, solvents, fungicides, fragrances, dispersing aids, rheological additives,
  • the preparation of the hardener composition (I) can be any suitable hardener composition.
  • the preparation of the hardener composition (I) can be any suitable hardener composition.
  • the adsorbent (C) is selected from the group of moisture-saturated molecular sieves, which are also called zeolites, and which are characterized in that they can absorb a maximum of 10 wt.% Of its own weight of water, preferably at most 5 wt.%.
  • the adsorbents (C) have long been known and commercially available.
  • the adsorbent (C) is added to at least 0.2% by weight, preferably 0.5% by weight, in the polymer composition (II). Preferably from 0.2 to 10% by weight, more preferably from 0.5 to 5% by weight.
  • the polydimethylsiloxanes (F) preferably have at least two silanol groups per molecule.
  • the viscosity of (F) is usually from 1,000 to 300,000 mPa.s at 25 ° C,
  • plasticizers (G) are liquid end-blocked by triorganosiloxy groups at room temperature
  • Methylphenylpolysiloxanes having a viscosity of usually 10 to 10,000 mPa.s at 25 ° C, preferably 50 to 5,000 mPa.s, particularly preferably 50 to 2,000 mPas.
  • the preparation of the polymer compositions (II) can be any suitable polymer compositions.
  • the other components (E) are also mixed in if necessary.
  • condensation-crosslinking RTV-2 silicone compositions according to the invention are used, for example, as adhesives and sealants in various applications.
  • Curing of RTV-2 silicone composite wafers is accomplished by contacting the hardener composition (I) with the
  • Alcohol can escape equilibrium. This leads to the fact that even the previously considered unsuitable catalyst (B) by a synergistic effect with moisture-saturated adsorbent (C) a uniform and good depth hardening in the
  • Silicone compositions achieved and thus can be dispensed with the use of the questionable Sn catalysts. It is thus possible to achieve a uniform good curing at layer thicknesses of 5mm or more.
  • a further advantage of the composition according to the invention is the simple commercial accessibility of the raw materials to be used. In addition, eliminates the need for a
  • the preparation of the polymer composition is carried out in accordance with the compounding technique known to those skilled in the art, in which, for example, in a planetary mixer or dissolver, the polymers (F) and optionally plasticizer (G) are introduced, optional further
  • Components (E) are stirred or homogeneously incorporated by means of dissolver disc.
  • the powdery molecular sieve (C) is incorporated and homogenized in the same way.
  • the preparation of the hardener composition is usually carried out by simply mixing together crosslinker (A), if necessary
  • Adhesion promoters (D), finally the catalyst (B) are Adhesion promoters (D), finally the catalyst (B)
  • OMG Catalyst 310 a Bi catalyst from OMG Borchers GmbH, Langenfeld
  • TES34 component (A)
  • Wacker Chemie AG Munich
  • Viscosity of about 100 mm 2 / s) (Wacker Chemie AG, Kunststoff) homogeneously mixed.
  • Hardener composition (according to Example 1) was added, homogeneously mixed and poured into metal rings (6 mm high, 43 mm diameter), which lie on Hostaflonfolien. At this
  • Polymer composition (® designation ELASTOSIL M 4512 a pourable, vulcanizes at room temperature
  • Constant weight under exposure to standard climate ensured and revealed by a residual moisture absorption of up to 5 wt.% From.
  • the pot life is determined by the viscosity measurement according to ISO 2555 (spindle 5, 2.5 rpm). The pot life is defined as the time to reach a viscosity of 60,000 mPas.
  • the cut surface must be tack-free and may have a maximum hardness deviation of 25% compared to the surface.
  • the Shore A hardness is determined according to DIN (German Industrial Standard) 53505 (March 2000 edition).
  • the elongation at break is determined according to DIN 53504-85S1.
  • the tensile strength is determined according to DIN 53504-85S1.
  • Table 1 shows, in addition to Example 2, Inventive Examples 3 to 6 and the results of curing in
  • Hardener preparation per 100 parts of polymer composition are already demoldable after 6 hours.
  • the differences in hardness of the specimens up / down decrease with increasing proportion of
  • Hardness differences top / bottom are particularly balanced with an adsorbent amount of 2 wt.%.
  • Examples 3-6 are all vulcanized, only sample 3 has a slight stickiness inside.
  • the vulcanizate is at addition levels of 2 wt% adsorbent inside
  • Adhesion-free, and the pot life is reduced with increasing amount of adsorbent.
  • Example 8 (according to the invention)
  • the vulcanizate is demolished after 24h at the top / bottom without sticking and has a hardness of 17 Shore A and 8 Shore A below.
  • Example 7 As the comparison of Example 7 with Examples 8 and 9 shows, remains in the non-inventive composition with a molecular sieve that has a moisture absorption of> 10 wt.%, The vulcanizate on the underside sticky and is no longer demoldable. Only with the invention
  • compositions according to Example 8 and 9 are obtained useful vulcanizates with good mechanical properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

Composition de silicone RTV-2 réticulant par condensation, à base (I) d'une composition de durcisseur contenant (A) au moins un agent de réticulation et (B) au moins un bi-catalyseur, et (II) d'une composition polymère, caractérisée en ce que la composition polymère (II) contient au moins 0,2 % en poids d'un agent d'adsorption (C) qui est sélectionné dans le groupe des tamis moléculaires saturés en humidité, lesquels sont caractérisés en ce qu'ils ne peuvent absorber que 10% au maximum de leur propre poids en eau.
EP13745382.5A 2012-08-17 2013-07-30 Compositions d'organosiloxane réticulant à l'ambiante Withdrawn EP2885352A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012214695.4A DE102012214695A1 (de) 2012-08-17 2012-08-17 Bei Raumtemperatur vernetzende Organosiloxanzusammensetzungen
PCT/EP2013/066037 WO2014026849A1 (fr) 2012-08-17 2013-07-30 Compositions d'organosiloxane réticulant à l'ambiante

Publications (1)

Publication Number Publication Date
EP2885352A1 true EP2885352A1 (fr) 2015-06-24

Family

ID=48917520

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13745382.5A Withdrawn EP2885352A1 (fr) 2012-08-17 2013-07-30 Compositions d'organosiloxane réticulant à l'ambiante

Country Status (6)

Country Link
US (1) US9181433B2 (fr)
EP (1) EP2885352A1 (fr)
KR (1) KR20150031321A (fr)
CN (1) CN104583324A (fr)
DE (1) DE102012214695A1 (fr)
WO (1) WO2014026849A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111500251A (zh) * 2020-04-16 2020-08-07 广州回天新材料有限公司 一种双组份缩合型粘接密封胶及其制备方法
WO2023122192A2 (fr) 2021-12-21 2023-06-29 L'oreal Compositions longue durée contenant un élastomère de silicone à fonction acide et un copolymère séquencé

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2843555A (en) 1956-10-01 1958-07-15 Gen Electric Room temperature curing organopolysiloxane
US3305502A (en) 1963-12-16 1967-02-21 Gen Electric Process for curing diorgano polysiloxanes at room temperature
JPS5232949A (en) 1975-09-08 1977-03-12 Shin Etsu Chem Co Ltd Cold-setting organo-polysiloxane composition
US4499230A (en) 1983-04-01 1985-02-12 General Electric Company One package, stable, moisture curable, alkoxy-terminated organopolysiloxane compositions containing a zeolite
JP3069365B2 (ja) * 1990-07-31 2000-07-24 東レ・ダウコーニング・シリコーン株式会社 加熱硬化性オルガノポリシロキサン組成物
DE19832686A1 (de) * 1998-07-21 2000-02-03 Heidelberger Bauchemie Gmbh Kondensationsvernetzendes Silikon mit hoher Festigkeit
JP2003119387A (ja) 2001-10-10 2003-04-23 Shin Etsu Chem Co Ltd 室温硬化性オルガノポリシロキサン組成物
US7527838B2 (en) 2006-04-06 2009-05-05 Momentive Performance Materials Inc. Architectural unit possessing translucent silicone rubber component
DE102010030842A1 (de) 2010-07-02 2012-01-05 Wacker Chemie Ag Lagerstabile Härterzusammensetzung im 2K System
JP2013139510A (ja) * 2011-12-29 2013-07-18 Dow Corning Toray Co Ltd 多成分型硬化性シリコーンゴム組成物、それを用いてなる電子部品用材料および太陽電池モジュール

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2014026849A1 *

Also Published As

Publication number Publication date
DE102012214695A1 (de) 2014-02-20
US9181433B2 (en) 2015-11-10
KR20150031321A (ko) 2015-03-23
CN104583324A (zh) 2015-04-29
WO2014026849A1 (fr) 2014-02-20
US20150152263A1 (en) 2015-06-04

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