EP2222626A1 - Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen - Google Patents

Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen

Info

Publication number
EP2222626A1
EP2222626A1 EP08873016A EP08873016A EP2222626A1 EP 2222626 A1 EP2222626 A1 EP 2222626A1 EP 08873016 A EP08873016 A EP 08873016A EP 08873016 A EP08873016 A EP 08873016A EP 2222626 A1 EP2222626 A1 EP 2222626A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
polycondensation
anion
elastomer
crosslinking
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
EP08873016A
Other languages
English (en)
French (fr)
Inventor
Christian Maliverney
Laurent Saint-Jalmes
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.)
Elkem Silicones France SAS
Original Assignee
Bluestar Silicones France SAS
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
Priority claimed from FR0708924A external-priority patent/FR2925516A1/fr
Application filed by Bluestar Silicones France SAS filed Critical Bluestar Silicones France SAS
Priority to EP18168305.3A priority Critical patent/EP3385304B1/de
Publication of EP2222626A1 publication Critical patent/EP2222626A1/de
Ceased 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/92—Ketonic chelates
    • 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
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • 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
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups

Definitions

  • the present invention relates to an organopolysiloxane composition that can be vulcanized from room temperature to a polycondensation-crosslinking elastomer and does not contain alkyltin catalysts which have toxicity problems.
  • the invention also relates to novel polycondensation catalysts in silicone chemistry and their use as catalysts for the polycondensation reaction of organopolysiloxanes.
  • the formulations of the polycondensation-crosslinking elastomers generally involve a silicone oil, generally a hydroxyl-terminated polydimethylsiloxane, optionally prefunctionalized with a silane so as to have alkoxy ends, a crosslinking agent, a polycondensation catalyst, conventionally a tin salt or an alkyl titanate, a reinforcing filler and any other additives such as fillers, adhesion promoters, dyes, biocides, etc.
  • organopolysiloxane compositions vulcanizable at room temperature are well known and are classified into 2 distinct groups: single-component compositions (RTV-I) and two-component compositions (RTV-2).
  • single component compositions crosslink when exposed to moisture in the air, i.e. they can not crosslink in a confined environment.
  • the single-component silicone compositions used as mastics or adhesives cold-crosslink following a mechanism for hydrolysis of reactive functions of the acetoxysilane, cetimoxysilane, alkoxysilane, etc. type, followed by condensation reactions between formed silanol groups and other residual reactive functions. Hydrolysis is usually carried out by means of the water vapor diffusing into the material from the surface exposed to the atmosphere. Generally, the kinetics of the polycondensation reactions is extremely slow; these reactions are catalyzed by a suitable catalyst.
  • catalysts As catalysts are used, it is most often used catalysts based on tin, titanium, an amine or compositions of these catalysts.
  • the catalysts based on tin see in particular FR-A-2,557,582) and titanium (see in particular FR-A-2,786,497) are catalysts having a good efficiency.
  • the two-component compositions When the two-component compositions, they are marketed and stored in the form of two components, a first component containing the base polymeric materials and the second component containing the catalyst. The two components are mixed during use and the crosslinked mixture in the form of a relatively hard elastomer.
  • These two-component compositions are well known and are described in particular in the work of Walter NoIl "Chemistry and Technology of Silicones" 1968, 2nd edition on pages 395 to 398. These compositions essentially comprise 4 different ingredients:
  • crosslinking agent generally a silicate or a polysilicate
  • the condensation catalyst is based on an organic tin compound.
  • tin catalysts have already been proposed as a crosslinking catalyst for these RTV-2.
  • the most widely used compounds are alkyltin carboxylates such as tributyltain monooleate or dialkyltin dicarboxylates such as dibutyltin dilaurate, dibutyltin diacetate or dimethyltin dilaurate (see the book “Chemistry and Technology of NoIl”). silicones "page 337, Academy Press, 1968 - 2nd edition or patents EP 147 323 or EP 235 049).
  • Titanium catalysts also widely used in RTV-I, however, have a major disadvantage: they have slower kinetics than tin catalysts. In addition, these catalysts are not usable in RTV-2 due to gelling problems.
  • Another important aspect for a catalyst of the polycondensation reaction of the organopolysiloxanes is the time of implementation ("pot-life” or “working time”), that is to say the time during which the composition can be used after mixing without curing. This time must be long enough to allow its use but short enough to obtain a manipulable molded object at the latest a few minutes or hours after its manufacture.
  • the catalyst must therefore make it possible to obtain a good compromise between the time of use of the catalyzed mixture and the time at the end of which the molded object can be handled (these times depend on the intended application, for example the molding or the manufacture of joints).
  • the catalyst must give the catalyzed mixture a spreading time that does not vary with the storage time.
  • the essential objective of the present invention is therefore to find new catalysts which both for the air humidity, crosslinking at the surface but also cross-linking as complete as possible.
  • Another essential objective of the present invention is to provide a catalyst that can be used both in the crosslinking of the mono- and bi-component elastomer compositions.
  • Another essential objective of the present invention is to propose a catalytic system which continues to meet both the conservation, implementation and crosslinking constraints of the two types of mono- and bi-component elastomer compositions.
  • an organopolysiloxane composition characterized in that it comprises on the one hand a silicone base B capable of being hardened by polycondensation reaction into a silicone elastomer. and on the other hand, a catalytically effective amount of at least one polycondensation catalyst which is a metal complex or salt A of formula (1): [Zn (L 1 ) (L 2 )] (1) wherein:
  • L 1 and L 2 are identical or different and represent a ligand which is a ⁇ -dicarbonylato anion or the enolate anion of a ⁇ -dicarbonyl compound of formula (2) or an acetylacetato anion derived from a ⁇ -dicarbonylato ketoester of the following formula (2): R 1 COCHR 2 COR 3 (2) 68
  • R 1 and R 2 can be connected to form a ring
  • complex or metal salt A includes any oligomeric form or the like of said complex or metal salt A.
  • inventive character of the invention is due to the judicious and advantageous selection of delimited associations of metal compounds A used as polycondensation catalyst.
  • This catalyst has the advantage of being liquid at ambient temperature (25 ° C.) and soluble in organic solvents, even in alkanes, and in silicone oils.
  • the ⁇ -dicarbonylato ligands L 1 and L 2 are ⁇ -diketonato anions derived from a ⁇ -diketone chosen from the group consisting of ⁇ -diketones: 2,4-hexanedione; 2,4-heptanedione; heptanedione-3,5; ethyl-3-2,4-pentanedione; methyl-5-hexanedione-2,4; octanedione-2,4; octanedione-3,5; dimethyl-5,5-hexanedione-2,4; methyl-6-2,4-heptanedione; 2,2-dimethyl-3,5-nonanedione; 2,6-dimethyl-3,5-heptanedione; 2-acetylcyclohexanone (Cyacac); 2,2,6,6-tetramethyl-3,5-
  • the ⁇ -dicarbonylato ligands L 1 and L 2 are ⁇ -ketoesterat anions chosen from the group consisting of anions derived from the following compounds: methyl, ethyl, n-propyl, isopropyl, n butyl, sec-butyl, isobutyl, tert-butyl, isopentyl, n-hexyl, n-octyl, 1-methylheptyl, n-nonyl, n-decyl and n-dodecyl acetylacetic acid.
  • the invention also relates to the novel compounds of formulas (5) and (6) below:
  • Another subject of the invention consists in using, as catalyst, the polycondensation reaction of organopolysiloxanes of the complexes or metal salts A according to the invention and as described above.
  • the amount of the polycondensation catalyst according to the invention is between 0.1 and 10% by weight of the total mass, preferably between 0.5 and 5%, whether it is a mono preparation or bi-components.
  • These silicone bases may be single-component, that is to say, packaged in a single package, and storage stable in the absence of moisture, curable in the presence of moisture, in particular moisture brought by the ambient air or water generated within the base during its use.
  • two-component bases can be used, that is to say packed in two packages, which harden as soon as the polycondensation catalyst is incorporated. according to the invention. They are conditioned after incorporation of the catalyst into two separate fractions, one of the fractions being able to contain, for example, only the catalyst according to the invention or a mixture with the crosslinking agent.
  • the polyorganosiloxane oil C is preferably an ⁇ , ⁇ -dihydroxypolydiorganosiloxane polymer having a viscosity of between 50 and 5,000,000 mPa.s at 25 ° C. and the crosslinking agent D is preferably an organosilicon compound bearing more than two groups. hydrolyzable bonded to silicon atoms per molecule.
  • the polyorganosiloxane oil C may also be functionalized at its ends by hydrolysable radicals obtained by condensation of a precursor bearing hydroxyl functional groups with a cross-linking silane bearing hydrolysable radicals.
  • crosslinking agent (D) mention may be made of: the silanes of the following general formula: in which the symbols R 2 , which are identical or different, represent alkyl radicals having from 1 to
  • alkoxy-C 3 -C alkoxy radicals mention may be made of the following radicals: CH 3 OCH 2 CH 2 -
  • R 1 represents a hydrocarbon radical Ci-Ci 0 encompassing:
  • vinyl radicals such as the phenyl, tolyl and xylyl radicals.
  • the crosslinking agents D are products that are accessible on the silicone market; moreover their use in compositions hardening at room temperature is known; it appears in particular in the French patents FR-AI 126 411, FR-AI 179 969, FR-AI 189 216, FR-AI 198 749, FR-AI 248 826, FR-AI 314 649, FR-AI 423 477, FR-Al 432 799 and FR-A-2 067 636.
  • alkyltrialkoxysilanes, alkyl silicates and alkyl polysilicates are more particularly preferred, in which the organic radicals are alkyl radicals having from 1 to 4 carbon atoms.
  • crosslinking agents D which can be used, mention is made more particularly of the following silanes:
  • linear non-reactive polyorganosiloxane polymers (G) may be introduced in order to act on the physical characteristics of the compositions in accordance with the invention and / or on the mechanical properties of the elastomers resulting from the hardening of these compositions.
  • non-reactive linear polyorganosiloxane polymers are well known; they more particularly include: ⁇ , ⁇ -bis (triorganosiloxy) diorganopolysiloxane polymers with viscosities of at least 10 mPa.s at 25 ° C., formed essentially of diorganosiloxy units and at most 1% of monoorganosiloxy and / or siloxy units , the organic radicals bonded to the silicon atoms being chosen from methyl, vinyl and phenyl radicals, at least 60% of these organic radicals being methyl radicals and 10% at most being vinyl radicals.
  • the viscosity of these polymers can reach several tens of millions of mPa.s at 25 ° C; they therefore include oils with fluid to viscous appearance and hard soft gums. They are prepared according to the usual techniques described more precisely in the French patents FR-A-978 058, FR-AI 025 150, FR-AI 108 764 and FR-AI 370 884. Preferably, the ⁇ , ⁇ -bis oils are used. (Trimethylsiloxy) dimethylpolysiloxanes with a viscosity ranging from 10 mPa.s to 1000 mPa.s at 25 ° C. These polymers which act as plasticizers can be introduced in a proportion of at most 70 parts, preferably from 5 to 20 parts. , per 100 parts of polyorganosiloxane C oil capable of crosslinking by polycondensation.
  • compositions according to the invention may also advantageously comprise at least one silicone resin (H).
  • silicone resins are branched organopolysiloxane polymers well known and commercially available. They have, per molecule, at least two different units chosen from those of formula R 111 SSiO 1 Q (unit M), Rr 2 SiO 2Z 2 (unit D), R 111 SiO 372 (unit T) and SiO 4/2 (unit Q).
  • the radicals R '" are identical or different and are chosen from linear or branched alkyl radicals, vinyl, phenyl and 3,3,3-trifluoropropyl radicals.
  • the alkyl radicals preferably contain from 1 to 6 carbon atoms, inclusive.
  • alkyl radicals R of methyl, ethyl, isopropyl, tert-butyl and n-hexyl radicals, these resins preferably being hydroxylated and in this case having a hydroxyl content by weight of between 5 and 500 meq / 100 g.
  • resins examples include MQ resins, MDQ resins, TD resins and MDT resins.
  • compositions in accordance with the invention it is necessary, in the case of single-component compositions, to use an apparatus which makes it possible to intimately mix, with the exclusion of moisture, with and without heat input, the various constituents to which the additives and additives mentioned above may be added. All these ingredients can be loaded into the apparatus in any order of introduction.
  • the mixtures can be heated to a temperature in the range 50- 180 0 C under atmospheric pressure or under reduced pressure to promote the departure of volatile materials.
  • compositions according to the invention that is to say undiluted, or in the form of dispersions in diluents, are stable storage in the absence of water and harden as soon as possible. low temperatures (after starting solvents in the case of dispersions) in the presence of water to form elastomers.
  • compositions according to the invention can be used for multiple applications such as grouting and / or gluing in the building industry, the transport industry (examples: automotive, aerospace, rail, maritime and aeronautics). assembly of the most diverse materials (metals, plastics, natural and synthetic rubbers, wood, cardboard, polycarbonate, faience, brick, ceramic, glass, stone, concrete and masonry), insulation of electrical conductors, encapsulation of electronic circuits and preparation of molds for the manufacture of resins or synthetic foams.
  • assembly of the most diverse materials metal, plastics, natural and synthetic rubbers, wood, cardboard, polycarbonate, faience, brick, ceramic, glass, stone, concrete and masonry
  • insulation of electrical conductors encapsulation of electronic circuits and preparation of molds for the manufacture of resins or synthetic foams.
  • oil (or oils) polyorganosiloxane (s) C may (s) crosslink by polycondensation to an elastomer
  • a catalyst of the polycondensation reaction which is the metal complex A according to the invention and as defined above.
  • a solution of 100 mmol of 97% sodium methylate (6.12 g) in 100 ml of isopropanol is concentrated by distillation of 20%, then 100 mmol of 95% isopropyl acetoacetate (15.93 g) are added and the solution is heated at 80 ° C. for 1 h to obtain a homogeneous orange solution.
  • a solution of zinc chloride (50 mmol, 7 g) in 50 ml of isopropanol is then added at 70 ° C. in 1 hour. The heating is maintained between 80 and 90 0 C for 3:30 and then the sodium chloride formed is filtered after cooling.
  • VTMO vinyltrimethoxysilane
  • test species is placed in contact with a short ⁇ , ⁇ -dihydroxylated polydimethylsiloxane oil QA equivalent to the OH content, viscosity of 100 mPa.s, oil 48V100), then a crosslinking agent, ethyl silicate is added (1 equivalent / OH), or the same volume of ethyl silicate called "advanced", that is to say a mixture of ethoxypolysiloxanes (in this case> léq / OH).
  • the mash used is prepared as follows: a mixture of 3464 g of ⁇ , ⁇ -dihydroxylated oil with a viscosity of 20000 centipoise containing 0.066% of OH, and 120 g of vinyltrimethoxysilane with stirring is added. g of a 2% by weight solution of lithium hydroxide in methanol, and then after 5 minutes, 400 g of pyrogenic silica AE55 are added. The mixture is devolatilized under vacuum and then stored away from moisture.
  • the symbol ">” corresponds to the hardness values measured on the top of the pion and the symbol “ ⁇ ” corresponds to the hardness values measured on the lower part of the pion, less exposed to ambient air. that the upper part
  • the working time with the new catalyst (6) according to the invention is a little longer than in the case of the tin catalyst allowing a good flexibility of use for an application of RTV2 type.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP08873016A 2007-12-20 2008-12-18 Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen Ceased EP2222626A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP18168305.3A EP3385304B1 (de) 2007-12-20 2008-12-18 Bei raumtemperatur vulkanisierbare organopolysiloxan-zusammensetzung zur bildung eines elastomers

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0708924A FR2925516A1 (fr) 2007-12-20 2007-12-20 Composition organopolysiloxanique vulcanisable a temperature ambiante en elastomere et nouveaux catalyseurs de polycondensation d'organopolysiloxanes.
FR0804801 2008-09-02
PCT/FR2008/001768 WO2009106718A1 (fr) 2007-12-20 2008-12-18 Composition organopolysiloxanique vulcanisable a temperature ambiante en elastomere et nouveaux catalyseurs de polycondensation d'organopolysiloxanes

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP18168305.3A Division EP3385304B1 (de) 2007-12-20 2008-12-18 Bei raumtemperatur vulkanisierbare organopolysiloxan-zusammensetzung zur bildung eines elastomers

Publications (1)

Publication Number Publication Date
EP2222626A1 true EP2222626A1 (de) 2010-09-01

Family

ID=40810044

Family Applications (2)

Application Number Title Priority Date Filing Date
EP08873016A Ceased EP2222626A1 (de) 2007-12-20 2008-12-18 Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP18168305.3A Active EP3385304B1 (de) 2007-12-20 2008-12-18 Bei raumtemperatur vulkanisierbare organopolysiloxan-zusammensetzung zur bildung eines elastomers

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP18168305.3A Active EP3385304B1 (de) 2007-12-20 2008-12-18 Bei raumtemperatur vulkanisierbare organopolysiloxan-zusammensetzung zur bildung eines elastomers

Country Status (6)

Country Link
US (1) US8835590B2 (de)
EP (2) EP2222626A1 (de)
JP (3) JP2011506738A (de)
KR (2) KR101443544B1 (de)
CN (2) CN105440288A (de)
WO (1) WO2009106718A1 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017220871A1 (fr) 2016-06-21 2017-12-28 Bluestar Silicones France Sas Procédé de lutte contre l'apparition de brouillard dans un dispositif à cylindres lors de l'enduction de supports flexibles avec une composition silicone liquide réticulable
WO2019220065A2 (fr) 2018-05-18 2019-11-21 Elkem Silicones France Sas Procede de production de materiaux silicones poreux
WO2020127818A1 (fr) 2018-12-20 2020-06-25 Elkem Silicones France Sas Procédé de lutte contre l'apparition de brouillard dans un dispositif a cylindres lors de l'enduction de supports flexibles avec une composition silicone liquide réticulable
WO2022023675A1 (fr) 2020-07-29 2022-02-03 Elkem Silicones France Sas Composition silicone réticulable en élastomère comprenant un additif de tenue thermique
WO2022129348A1 (fr) 2020-12-16 2022-06-23 Elkem Silicones France Sas Composition silicone biocide applicable sur des surfaces

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105440288A (zh) * 2007-12-20 2016-03-30 蓝星有机硅法国公司 在环境温度下可硫化成弹性体的有机聚硅氧烷组合物以及新的有机聚硅氧烷缩聚催化剂
FR2925511A1 (fr) * 2007-12-20 2009-06-26 Bluestar Silicones France Soc Composition organopolysiloxanique vulcanisable a temperature ambiante en elastomere et nouveaux catalyseurs de polycondensation d'organopolysiloxanes.
EP2382044B1 (de) * 2008-10-13 2018-08-01 ELKEM SILICONES France SAS Neue katalysatoren für die umsetzung von einem isocyanat und einem alkohol
ES2477561T3 (es) * 2009-06-19 2014-07-17 Bluestar Silicones France Composición de silicona reticulable por deshidrogenación-condensación en presencia de un catalizador metálico
EP2492323A1 (de) 2011-02-23 2012-08-29 Akzo Nobel Coatings International B.V. Biofäulebeständige Zusammensetzungen
US9012585B2 (en) 2011-07-20 2015-04-21 Dow Corning Corporation Zinc containing complex and condensation reaction catalysts, methods for preparing the catalysts, and compositions containing the catalysts
KR101881965B1 (ko) 2011-08-18 2018-07-25 아크조노벨코팅스인터내셔널비.브이. 스테롤 및/또는 그의 유도체를 포함하는 내오염성 조성물
US9139699B2 (en) 2012-10-04 2015-09-22 Dow Corning Corporation Metal containing condensation reaction catalysts, methods for preparing the catalysts, and compositions containing the catalysts
KR101738602B1 (ko) 2011-10-17 2017-06-08 신에쓰 가가꾸 고교 가부시끼가이샤 축합반응 경화형 실리콘 박리 코팅 조성물
DE102012206489A1 (de) * 2012-04-19 2013-10-24 Wacker Chemie Ag Härterzusammensetzungen für kondensationsvernetzende RTV-2-Systeme
FR2999980A1 (fr) * 2012-12-20 2014-06-27 Bluestar Silicones France Article presentant des proprietes antisalissures et destine a etre utilise dans des applications aquatiques en particulier marines
JP6134006B2 (ja) * 2012-12-20 2017-05-24 ブルースター・シリコーンズ・フランス・エスアエス 水中用途、特に海洋用途を目的とする防汚特性を有する物品
CN104981523B (zh) * 2012-12-20 2018-10-09 埃肯有机硅法国简易股份公司 在环境温度下可硫化成弹性体的有机聚硅氧烷组合物以及有机聚硅氧烷缩聚催化剂
CN104981524B (zh) 2012-12-20 2020-03-13 埃肯有机硅法国简易股份公司 在环境温度下可硫化成弹性体的有机聚硅氧烷组合物以及新的有机聚硅氧烷缩聚催化剂
MX2015010754A (es) 2013-02-26 2015-11-30 Akzo Nobel Coatings Int Bv Composiciones anti-suciedad con un polimero u oligomero que contiene un oxialquileno fluorado.
EP2813529A1 (de) 2013-06-11 2014-12-17 Sika Technology AG Härtbare Zusammensetzung auf Basis von Silangruppen-haltigen Polymeren und einem Zinkkatalysator
DK3077468T3 (en) 2013-12-03 2018-05-22 Akzo Nobel Coatings Int Bv PROCEDURE FOR COATING AN OLD COATING LAYER ON A SUBSTRATE AND COATING COMPOSITION SUITABLE FOR USE IN THIS PROCEDURE
FR3020067A1 (fr) * 2014-04-18 2015-10-23 Bluestar Silicones France Procede d'enduction d'un composition silicone sur un support souple
CN106062011B (zh) * 2014-05-21 2018-03-16 道康宁公司 含锌催化剂、制备含锌催化剂的方法以及包含含锌催化剂的组合物
WO2016137881A1 (en) 2015-02-23 2016-09-01 King Industries Curable coating compositions of silane functional polymers
CN106928725A (zh) 2015-12-31 2017-07-07 蓝星有机硅（上海）有限公司 导电的可固化的有机硅橡胶
JP6866488B2 (ja) 2017-01-17 2021-04-28 アクゾ ノーベル コーティングス インターナショナル ビー ヴィ 汚損剥離コーティング組成物、該コーティング組成物でコーティングされた基材、および該コーティング組成物の使用
US11597123B2 (en) * 2017-06-29 2023-03-07 Elkem Silicones France Sas Method for producing silicone elastomer molds
JP6931131B2 (ja) 2017-12-14 2021-09-01 アクゾ ノーベル コーティングス インターナショナル ビー ヴィ 多層塗料系で被覆された基材および多層塗料系を使用する人工物体上の水生生物汚損を防除する方法
SG11202100108SA (en) 2018-07-13 2021-02-25 Akzo Nobel Coatings Int Bv Tie-coat composition
WO2020164005A1 (en) 2019-02-13 2020-08-20 Dow Global Technologies Llc Moisture-curable polyolefin formulation
BR112021021152A2 (pt) * 2019-06-19 2021-12-28 Momentive Performance Mat Jp Composição de agente de revestimento aquoso
CA3143372A1 (en) * 2019-06-27 2020-12-30 Dow Silicones Corporation Room temperature vulcanisable silicone compositions
WO2021113564A1 (en) * 2019-12-06 2021-06-10 Lonza Solutions Ag Compositions for antifouling protection
WO2022207681A1 (en) 2021-03-30 2022-10-06 Akzo Nobel Coatings International B.V. Fouling control coating composition
CN115991875B (zh) * 2023-02-15 2023-12-15 杭州之江有机硅化工有限公司 一种脱醇型室温硫化硅橡胶用钛酸酯催化剂及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147323A2 (de) * 1983-12-28 1985-07-03 Rhone-Poulenc Chimie Elastomere härtbare Silikonzusammensetzungen, die einen Zinnchelatkatalysator enthalten
EP1964872A1 (de) * 2007-02-26 2008-09-03 Wacker Chemie AG Verfahren zur Herstellung von Organyloxygruppen aufweisenden Organosiliciumverbindungen

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR978058A (fr) 1948-11-13 1951-04-09 Amorceur pour pêche
BE498183A (de) 1949-11-10 1900-01-01
FR1108764A (fr) 1953-06-24 1956-01-17 Thomson Houston Comp Francaise Stabilisation et perfectionnement des organopolysiloxanes
FR1126411A (fr) 1954-02-18 1956-11-22 Dow Corning élastomères siloxanes
FR1126884A (fr) 1954-10-02 1956-12-03 Teves Kg Alfred Régulateur de pression pour la répartition harmonique de la pression
FR1136885A (fr) 1954-10-06 1957-05-21 Dow Corning Procédé de fabrication de produits organosiliciques pulvérulents hydrophobes
US3127363A (en) 1955-08-05 1964-03-31 Process for the manufacture of elasto-
BE556585A (de) 1956-04-11
FR1189216A (fr) 1956-10-01 1959-10-01 Thomson Houston Comp Francaise Compositions d'organopolysiloxanes durcissables à la température ambiante
FR1198749A (fr) 1958-02-06 1959-12-09 Rhone Poulenc Sa Compositions organopolysiloxaniques vulcanisables
DE1120690B (de) 1959-02-20 1961-12-28 Wacker Chemie Gmbh Bei Zutritt von Luftfeuchtigkeit bei Raumtemperatur haertende Massen auf Basis von Organopolysiloxanen
GB1024234A (en) 1962-06-27 1966-03-30 Midland Silicones Ltd Improvements in or relating to siloxane elastomers
FR1370884A (fr) 1963-07-30 1964-08-28 Dow Corning Compositions siloxane
DE1224039B (de) 1964-02-06 1966-09-01 Bayer Ag Unter Ausschluss von Wasser lagerfaehige, plastische Organopolysiloxanformmassen
FR1432799A (fr) 1965-02-12 1966-03-25 Rhone Poulenc Sa Aldiminoxysilanes et siloxanes et compositions en contenant
US3494951A (en) 1967-09-20 1970-02-10 Gen Electric Nitrogen-containing organosilicon materials and methods for producing them
US3453300A (en) * 1967-12-14 1969-07-01 Grace W R & Co Preparation of zinc ethyl acetoacetate chelate
BE758713A (fr) 1969-11-12 1971-05-10 Rhone Poulenc Sa Iminoxyorganoxysilanes
US3689454A (en) 1971-01-06 1972-09-05 Gen Electric Curable compositions
GB1350420A (en) 1971-01-06 1974-04-18 Gen Electric Alkanedioxy titanium chelates
US3801572A (en) 1971-08-23 1974-04-02 Gen Electric Amino-functional silicone compounds
US3888815A (en) 1973-08-20 1975-06-10 Gen Electric Self-bonding two-package room temperature vulcanizable silicone rubber compositions
JPS5411953A (en) 1977-06-29 1979-01-29 Shin Etsu Chem Co Ltd Cold-curable organopolysiloxane composition
US4115356A (en) 1977-07-18 1978-09-19 Dow Corning Corporation Self adhering room temperature vulcanizable silicone elastomers
FR2439805A1 (fr) 1978-10-24 1980-05-23 Rhone Poulenc Ind Compositions organopolysiloxaniques durcissables en elastomeres pour la fabrication de moules
US4273698A (en) 1979-02-28 1981-06-16 General Electric Company Self-bonding room temperature vulcanizable silicone rubber compositions
FR2458572A1 (fr) 1979-06-08 1981-01-02 Rhone Poulenc Ind Compositions organopolysiloxaniques durcissant en elastomeres, des la temperature ambiante en presence d'eau
DE3061802D1 (en) 1979-11-28 1983-03-03 M & T Chemicals Inc Hydantoinylsilanes and bis(hydantoinyl)disiloxanes and method for preparing same
DE3039720A1 (de) 1980-10-21 1982-05-27 Wacker-Chemie GmbH, 8000 München Umsetzungsprodukte von kieselsaeureester mit organischer zinnverbindung und ihre verwendung
US4356116A (en) 1981-04-03 1982-10-26 General Electric Company Devolatilized room temperature vulcanizable silicone rubber composition
DE3134931A1 (de) 1981-09-03 1983-04-28 Bayer Ag, 5090 Leverkusen Aminoorganoaminosilane, verfahren zu deren herstellung und deren verwendung
FR2531095B1 (fr) 1982-07-30 1987-08-14 Rhone Poulenc Spec Chim Compositions organopolysiloxaniques monocomposantes comportant en tant que reticulants des silanes a groupements acyloxyle ou cetoniminoxyle et catalysees par des derives organiques du titane
FR2540129B1 (fr) 1983-01-27 1985-06-21 Rhone Poulenc Spec Chim Compositions organopolysiloxaniques contenant des polyacyloxysilanes et durcissant tres rapidement en elastomeres en presence d'accelerateur du type phosphate
FR2540128B1 (fr) 1983-01-27 1986-02-21 Rhone Poulenc Spec Chim Compositions organopolysiloxaniques contenant des polyacyloxysilanes et durcissant tres rapidement en elastomeres en presence d'accelerateur du type hydroxyde metallique
FR2550541B1 (fr) 1983-08-12 1987-04-10 Rhone Poulenc Spec Chim Compositions organopolysiloxaniques monocomposantes resistant aux microorganismes
FR2572415B1 (fr) 1984-10-29 1987-01-09 Rhone Poulenc Spec Chim Composition organopolysiloxanique vulcanisable a temperature ambiante en elastomere auto-adherent
FR2592657B1 (fr) 1986-01-09 1988-05-20 Rhone Poulenc Spec Chim Systeme catalytique a l'etain pour composition organopolysiloxane durcissable des la temperature ambiante.
US4677147A (en) * 1986-03-24 1987-06-30 Dow Corning Corporation Bakeware release coating
FR2634768A1 (fr) * 1988-07-29 1990-02-02 Rhone Poulenc Chimie Procede de preparation de diorganopolysiloxanes a groupements terminaux alcoxy
FR2757869B1 (fr) 1996-12-31 1999-05-21 Rhodia Chimie Sa Utilisation de melanges a base de pt et de composes de metaux de transition autres que le pt pour ameliorer les proprietes de resistance a l'arc des elastomeres silicones
FR2786497B1 (fr) 1998-11-27 2001-01-05 Rhodia Chimie Sa Compositions organopolysiloxanes durcissant en elastomeres translucides des la temperature ambiante en presence d'humidite
DE10242415A1 (de) * 2002-09-12 2004-03-25 Wacker-Chemie Gmbh Organopolysiloxane und deren Einsatz in bei Raumtemperatur vernetzbaren Massen
DE10259613A1 (de) * 2002-12-19 2004-07-08 Wacker-Chemie Gmbh Organopolysiloxanzusammensetzungen und deren Einsatz in bei Raumtemperatur vernetzbaren niedermoduligen Massen
FR2887552B1 (fr) * 2005-06-24 2007-10-12 Rhodia Chimie Sa Utilisation d'une composition organopolysiloxanique vulcanisable des la temperature ambiante pour former un elastomere auto adherent
JP4766679B2 (ja) * 2006-02-21 2011-09-07 信越化学工業株式会社 加熱硬化型オルガノポリシロキサン組成物
JP2007231030A (ja) * 2006-02-27 2007-09-13 Shin Etsu Chem Co Ltd 皮膜形成シリコーンエマルジョン組成物
CN105440288A (zh) * 2007-12-20 2016-03-30 蓝星有机硅法国公司 在环境温度下可硫化成弹性体的有机聚硅氧烷组合物以及新的有机聚硅氧烷缩聚催化剂

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147323A2 (de) * 1983-12-28 1985-07-03 Rhone-Poulenc Chimie Elastomere härtbare Silikonzusammensetzungen, die einen Zinnchelatkatalysator enthalten
EP1964872A1 (de) * 2007-02-26 2008-09-03 Wacker Chemie AG Verfahren zur Herstellung von Organyloxygruppen aufweisenden Organosiliciumverbindungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO2009106718A1 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017220871A1 (fr) 2016-06-21 2017-12-28 Bluestar Silicones France Sas Procédé de lutte contre l'apparition de brouillard dans un dispositif à cylindres lors de l'enduction de supports flexibles avec une composition silicone liquide réticulable
US11078379B2 (en) 2016-06-21 2021-08-03 Elkem Silicones France Sas Method for the prevention of mist formation in a device comprising rolls during the coating of flexible media with a crosslinkable liquid silicone composition
WO2019220065A2 (fr) 2018-05-18 2019-11-21 Elkem Silicones France Sas Procede de production de materiaux silicones poreux
WO2020127818A1 (fr) 2018-12-20 2020-06-25 Elkem Silicones France Sas Procédé de lutte contre l'apparition de brouillard dans un dispositif a cylindres lors de l'enduction de supports flexibles avec une composition silicone liquide réticulable
WO2022023675A1 (fr) 2020-07-29 2022-02-03 Elkem Silicones France Sas Composition silicone réticulable en élastomère comprenant un additif de tenue thermique
WO2022129348A1 (fr) 2020-12-16 2022-06-23 Elkem Silicones France Sas Composition silicone biocide applicable sur des surfaces

Also Published As

Publication number Publication date
US8835590B2 (en) 2014-09-16
EP3385304B1 (de) 2020-07-15
KR20130018366A (ko) 2013-02-20
JP5770151B2 (ja) 2015-08-26
KR20100087227A (ko) 2010-08-03
JP2015083584A (ja) 2015-04-30
JP2013064147A (ja) 2013-04-11
JP2011506738A (ja) 2011-03-03
CN101932546A (zh) 2010-12-29
EP3385304A1 (de) 2018-10-10
CN105440288A (zh) 2016-03-30
KR101443544B1 (ko) 2014-09-22
WO2009106718A1 (fr) 2009-09-03
US20110046304A1 (en) 2011-02-24

Similar Documents

Publication Publication Date Title
EP3385304B1 (de) Bei raumtemperatur vulkanisierbare organopolysiloxan-zusammensetzung zur bildung eines elastomers
EP2222756B1 (de) Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP2222775B1 (de) Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP2268743B1 (de) Verbindungen mit einer guanidinstruktur und ihre verwendung als organopolysiloxan-polykondensationskatalysatoren
EP2222774B1 (de) Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP2222688B1 (de) Verbindungen mit einer guanidinstruktur und ihre verwendung als organopolysiloxan-polykondensationskatalysatoren
EP2367867B1 (de) Verbindungen mit guanidinstruktur und verwendung davon als organopolysiloxan-polykondensationskatalysatoren
EP2222773B1 (de) Silikonzusammensetzung die bei umgebungstemperatur vulkanisierbar ist und katalysator für die polykondensation von organosiloxanpolymeren
EP2222772B1 (de) Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzummensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP2222770B1 (de) Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP2222771A1 (de) Bei zimmertemperatur zu einem elastomer vulkanisierbare organopolysiloxanzusammensetzung sowie neuartige katalysatoren zur polykondensation von organopolysiloxanen
EP3215557B1 (de) Neuartige silikonzusammensetzung zur vernetzung von katalysatoren
EP2729533B1 (de) Verwendung von carbenen in einer lösung als organopolysiloxan-polykondensationskatalysatoren
WO2005071007A1 (fr) Composition polyorganosiloxane monocomposante reticulant en elastomere silicone

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20100629

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20121106

APBK Appeal reference recorded

Free format text: ORIGINAL CODE: EPIDOSNREFNE

APBN Date of receipt of notice of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA2E

APBR Date of receipt of statement of grounds of appeal recorded

Free format text: ORIGINAL CODE: EPIDOSNNOA3E

APAF Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNE

APAF Appeal reference modified

Free format text: ORIGINAL CODE: EPIDOSCREFNE

REG Reference to a national code

Ref country code: DE

Ref legal event code: R003

APBT Appeal procedure closed

Free format text: ORIGINAL CODE: EPIDOSNNOA9E

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: ELKEM SILICONES FRANCE SAS

18R Application refused

Effective date: 20180502