WO2013191955A1 - Organopolysiloxanes monofonctionnels pour agents de compatibilité polyhétérosiloxanes - Google Patents

Organopolysiloxanes monofonctionnels pour agents de compatibilité polyhétérosiloxanes Download PDF

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Publication number
WO2013191955A1
WO2013191955A1 PCT/US2013/045069 US2013045069W WO2013191955A1 WO 2013191955 A1 WO2013191955 A1 WO 2013191955A1 US 2013045069 W US2013045069 W US 2013045069W WO 2013191955 A1 WO2013191955 A1 WO 2013191955A1
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Prior art keywords
organosiloxane
sio
hydrocarbyl
formula
group
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PCT/US2013/045069
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English (en)
Inventor
Don Lee Kleyer
Nanguo Liu
Adam C. TOMASIK
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Dow Corning Corporation
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Publication of WO2013191955A1 publication Critical patent/WO2013191955A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences

Definitions

  • polyheterosiloxanes has been of great interest for a wide range of applications due to their ability to impart high refractive index, impact resistance, scratch resistance, fire retardance, anti-corrosion, anti-stain, etc.
  • Methods for preparing polyheterosiloxane materials having at least two different non-Si metal elements has recently been disclosed in WO2011/002826. While the teachings of WO2011/002826 provide polyheterosiloxane compositions that have solubility in various organic solvents, there still remains a need to identify compositions and methods for improving the compatibility of polyheterosiloxane compositions with other polymers, and in particular with polydiorganosiloxanes.
  • the present inventors have discovered certain organosiloxane compositions that are useful to enhance the compatibility of polyheterosiloxanes with polydiorganosiloxanes.
  • the present disclosure relates to an organosiloxane having the formula; Si-R 2 -Si(R 1 ) 2 OSi(R 3 ) 2 X
  • n 1 or 2
  • R 1 is independently a monovalent Ci to C 2 o hydrocarbyl
  • R is a divalent C 2 to C 12 hydrocarbyl
  • R is independently a monovalent Ci to C30 hydrocarbyl
  • X is a hydrolyzable group selected from
  • R 4 is hydrogen or a Ci to C 6 alkyl group.
  • the present disclosure further provides a process for preparing an organosiloxane by:
  • R is independently a monovalent Ci to C30 hydrocarbyl
  • R 4 is hydrogen or a Ci to C 6 alkyl group
  • R 1 is independently a monovalent Ci to C 20 hydrocarbyl
  • R 5 is a C 2 to C 12 hydrocarbyl having a terminal unsaturated group, to form a mixture containing an organosiloxane of the formula
  • step IV optionally, further processing the reaction mixture of step III to remove any
  • the present disclosure relates to an organosiloxane having the formula; Si-R 2 -Si(R 1 ) 2 OSi(R 3 ) 2 X
  • n 1 or 2
  • R 1 is independently a monovalent Ci to C 20 hydrocarbyl
  • R is a divalent C 2 to C 12 hydrocarbyl
  • R is independently a monovalent Ci to C 30 hydrocarbyl
  • X is a hydrolyzable group selected from
  • R 4 is hydrogen or a Ci to C 6 alkyl group.
  • R 1 is independently a monovalent Ci to C 2 o hydrocarbyl.
  • the hydrocarbon group may independently be an alkyl, aryl, or alkylaryl group.
  • hydrocarbyl also includes halogen substituted hydrocarbyls.
  • R 1 may be a Ci to C 2 o alkyl group, alternatively R 1 may be a Ci to Cig alkyl group.
  • R 1 may be a Ci to C 6 alkyl group such as methyl, ethyl, propyl, butyl, pentyl, or hexyl.
  • R 1 may be an aryl group, such as phenyl, naphthyl, or an anthryl group.
  • R 1 may be any combination of the aforementioned alkyl or aryl groups.
  • R 1 is phenyl, methyl, or a combination of both.
  • R 1 is methyl.
  • R 2 is divalent hydrocarbon group containing 2 to
  • R 2 contains 2 to 6 carbon atoms, alternatively R 2 is ethylene, propylene, or isobutylene, alternatively R is ethylene (-CH 2 CH 2 -).
  • R 3 is independently a monovalent Ci to C 30 hydrocarbyl containing at least one aryl group.
  • R may be an aryl group, such as phenyl, naphthyl, or an anthryl group.
  • R may be any combination of the aforementioned alkyl or aryl groups.
  • R is phenyl (C 6 H 5 ).
  • R 4 is hydrogen or a Ci to C 6 alkyl group such as a methyl, ethyl, propyl, isopropyl, butyl, pentyl, or hexyl group.
  • R 4 is methyl.
  • X may be an alkoxy, hydroxyl, carboxy, amine, chloride, or oxime group.
  • X is -OCH 3 , -OCH 2 CH 3 , -
  • X is -OCH 3 .
  • the organosiloxane has the following formula
  • the organosiloxane has the formula
  • n 1 or 2
  • R 1 is independently a monovalent Ci to C 2 o hydrocarbyl
  • G is a siloxane or polysiloxane bridging group comprising at least one siloxy unit selected from a (R 2 Si0 2 / 2 ), (RSi0 3 / 2 ), or (S1O4/2) siloxy units, where R may be any organic group,
  • R is independently a monovalent Ci to C 3 o hydrocarbyl
  • X is a hydrolyzable group selected from
  • R 4 is hydrogen or a Ci to C 6 alkyl group.
  • G is a siloxane or polysiloxane bridging group comprising at least one siloxy unit selected from a (R 2 Si0 2 / 2 ), (RSi0 3 / 2 ), or (Si0 4 / 2 ) siloxy units, where R may be any organic group.
  • G may also be a combination of hydrocarbyl bridging groups, such as the divalent C 2 to C12 hydrocarbyl groups described above for R , and a siloxane or polysiloxane.
  • G is a polydimethylsiloxane of the formula -0(Me 2 Si0 2 /2) q - where the subscript q may vary from 1 to 20, alternatively from 1 to 10, or alternatively from 1 to 5.
  • the polysiloxane bridging group contains a (RSi0 3/2 ), or (Si0 4/2 ) siloxy unit(s), it may further contain additional R SiOi /2 siloxy units to provide endcapping groups.
  • some of the (RSi0 3 / 2 ), or (Si0 4 / 2 ) siloxy unit(s) when present in the bridging group may be silanol terminated.
  • the present organosiloxanes may be prepared by any known methods, or alternatively are prepared according to the methods as described below. [0017] This disclosure further provides a method for preparing the present organosiloxanes by
  • R is independently a monovalent C to C30 hydrocarbyl
  • R 4 is hydrogen or a Ci to C 6 alkyl group
  • R 1 is independently a monovalent Ci to C 2 o hydrocarbyl
  • R 5 is a C 2 to C 12 hydrocarbyl having a terminal unsaturated group, to form a mixture containing an organosiloxane of the formula
  • step IV optionally, further processing the reaction mixture of step III to remove any
  • the first step involves reacting
  • R 3 and R 4 in the (R 3 ) 2 Si(OR 4 ) 2 organosilane formula are the same as defined above.
  • R 1 in the disiloxane formula R 5 (R 1 ) 2 SiOSi(R 1 ) 2 R 5 is the same as defined above.
  • R 5 is this formula is a C 2 to C 12 hydrocarbyl having a terminal unsaturated group.
  • the terminal unsaturated group may be either an alkene or alkyne.
  • the terminal unsaturated group is vinyl.
  • step I The reaction effected in step I may be considered as an "equilibration" reaction.
  • the reaction of step I may be conducted under those conditions known in the art for performing organosiloxane equilibration reactions.
  • a sufficient quantity of an equilibration catalyst is added to enhance the reaction.
  • Suitable, non-limiting, equilibration catalysts include strong acids such as trifluoromethane sulfonic acid.
  • the amount of components a) and b) may vary and is not limiting. Typically, the reaction is conducted such that the amount of the disiloxane component b) added in step I) provides a slight molar excess vs the amount of the organosilane component a).
  • organosilanes suitable as component a) in the present process include; dimethoxydiphenylsilane , diethoxydiphenylsilane,
  • phenylmethyldimethoxysilane phenylmethyldiethoxysilane, dimethyldimethoxysilane, diethyldimethoxysilane, dimethyldiethoxysilane, diethyldiethoxysilane,
  • diorganosiloxanes suitable as component b) in the present process include; divinyltetramethyldisiloxane, diallyltetramethyldisiloxane, dihexenyltetramethyldisiloxane, hexamethyldisiloxane, tetramethyldisilxoane, etc.
  • R 5 (R 1 ) 2 SiOSi (R 3 ) 2 OR 4 organosiloxane of step I) may be prepared by alternative methods. Representative general reactions schemes to prepare the organosiloxane of step I) are summarized below;
  • ViMe 2 SiOSiPh 2 X types different SiH functional siloxanes may be used, e.g. ViMe 2 SiOSiPh 2 X + HSi(OSiMe 3 ) 3 + Pt cat -> (Me 3 SiO) 3 SiCH 2 CH 2 Ph 2 SiX alt. use
  • HMeSi(OSiMe 3 ) 2 , HMe 2 SiOSiMe 3 , HMe 2 Si(OMe 2 Si) x OSiMe 3 (Gelest or make from Me 3 SiOLi + x D 3 -> Me 3 SiO(Me 2 SiO) 3x Li + Me 2 HSiCl -> Me 3 SiO(Me 2 SiO) 3x SiMe 2 H or another alt.
  • Step II of the present process is optional, but when selected involves processing the mixture to remove unreacted starting components or other volatile components. Typically, processing involves heating the reaction mixture to a temperature ranging from 25 °C to 150°C, alternatively from 40° to 100°C, at reduced pressure while removing volatile species from the mixture under these conditions.
  • Step III involves reacting the R 5 (R 1 ) 2 SiOSi (R 3 ) 2 OR 4 organosiloxane with
  • the organohydrogensiloxane used in step III has the formula (R 1 3 SiO) n (R 1 )(3_ n ) SiH, where R 1 and n are as defined above. Typically R 1 is methyl and n is 2, so that the organohydrogensiloxane has the formula (Me 3 SiO) 2 (Me)SiH.
  • the reaction effected in step III is a hydro silylation reaction, in which the SiH of the organohydrogensiloxane reacts with the unsaturated group present on R 5 (R 1 ) 2 SiOSi (R 3 ) 2 OR 4 organosiloxane formed in step I of the present process to form an Si-C bond.
  • the reaction may be conducted under those conditions known in the art for effecting hydrosilylations reactions.
  • the hydrosilylation reaction can be conducted neat or in the presence of a solvent.
  • the solvent can be an alcohol such as methanol, ethanol, isopropanol, butanol, or n-propanol, a ketone such as acetone, methylethyl ketone, or methyl isobutyl ketone; an aromatic hydrocarbon such as benzene, toluene, or xylene; an aliphatic hydrocarbon such as heptane, hexane, or octane; a glycol ether such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, or ethylene glycol n-butyl ether, a halogenated hydrocarbon such as dichloromethane, 1,1,1- trichloroethane or methylene chloride, chloroform, di
  • the amount of solvent can be up to 70 weight percent, but is typically from 20 to 50 weight percent, said weight percent being based on the total weight of components in the hydrosilylation reaction.
  • the solvent used during the hydrosilylation reaction can be subsequently removed by various known methods.
  • Additional components can be added to the hydrosilylation reaction which are known to enhance such reactions. These components include salts such as sodium acetate which have a buffering effect in combination with platinum catalysts.
  • the amounts of component c used in the hydrosilylation reaction vs the amount of the R 5 (R 1 ) 2 SiOSi (R 3 ) 2 OR 4 organosiloxane may vary.
  • the molar ratio of the SiH units of component c) to the unsaturated groups of the R 5 (R 1 ) 2 SiOSi (R 3 ) 2 OR 4 organosiloxane may range from 10/1 to 1/10, alternatively from 5/1 to 1/5, or alternatively from 2/1 to 1/2.
  • Component d) is a hydrosilylation catalyst.
  • the hydrosilylation catalyst may be any suitable Group VIII metal based catalyst selected from a platinum, rhodium, iridium, palladium or ruthenium.
  • Group VIII metal containing catalysts useful to catalyze curing of the present compositions can be any of those known to catalyze reactions of silicon bonded hydrogen atoms with unsaturated hydrocarbon groups.
  • the preferred Group VIII metal for use as a catalyst to effect cure of the present compositions by hydrosilylation is a platinum based catalyst.
  • Some preferred platinum based hydrosilylation catalysts for curing the present composition are platinum metal, platinum compounds and platinum complexes.
  • Suitable platinum catalysts are described in US 2,823,218 (commonly referred to as “Speier's catalyst) and U.S. Patent No. 3,923,705.
  • the platinum catalyst may be "Karstedt's catalyst", which is described in Karstedt's U.S. Patent Nos. 3,715,334 and 3,814,730.
  • Karstedt's catalyst is a platinum divinyl tetramethyl disiloxane complex typically containing about one- weight percent of platinum in a solvent such as toluene.
  • the platinum catalyst may be a reaction product of chloroplatinic acid and an organosilicon compound containing terminal aliphatic unsaturation, as described in U.S. Patent No. 3,419,593.
  • the hydro silyation catalyst is a neutralized complex of platinum chloride and divinyl tetramethyl disiloxane, as described in US 5, 175,325.
  • suitable hydrosilylation catalysts are described in, for example, U.S. Patents 3,159,601; 3,220,972; 3,296,291; 3,516,946;
  • the hydrosilylation catalyst may be added in an amount equivalent to as little as 0.001 part by weight of elemental platinum group metal, per one million parts (ppm) of the total reaction composition.
  • concentration of the hydrosilylation catalyst in the reaction composition is that capable of providing the equivalent of at least 1 part per million of elemental platinum group metal.
  • a catalyst concentration providing the equivalent of 1 to 500, alternatively 5 to 500, alternatively 10 to 100 parts per million of elemental platinum group metal may be used.
  • Step IV of the present process is optional, and involves further processing the reaction mixture of step III to remove any volatile components. Step IV may be effected in a similar manner as step II, as described above.
  • the present disclosure further provides a method for improving the compatibility of a polyheterosiloxane by using the present organosiloxanes of the formula
  • the present organosiloxanes may be added as a siloxane component in the preparation of the polyheterosiloxanes, as described in
  • WO2011/002826 teaches a method for preparing a polyheterosiloxane having at least two non-Si metal elements comprising:
  • (R 1 3 SiO) n (R 1 )(3_ n) Si-R 2 -Si(R 1 ) 2 OSi(R 3 ) 2 X may be used as all or part of component (Bl) in the WO2011/002826 method.
  • the amount of the present organosiloxanes used as component Bl in the WO2011/002826 method may vary from 0.05 weight percent to 100 weight percent of the total amount of organosiloxane added for the preparation of the polyhetereosiloxane.
  • ViMe 2 SiOSiPh 2 (OMe) was first prepared by mixing 151.8g
  • ViMe 2 Si(OMe) and unreacted divinyltetramethyldisiloxane were removed at 50-60°C and 0.3-0.5mmHg.
  • 117.6 g material was collected in a 3-neck flask. The flask was heated to 90°C. Then, O. lg 1% Pt was added to the flask. Under stirring, 70.8g (Me 3 SiO) 2 (Me)SiH was slowly added into the flask in approximately 30 minutes. Temperature rose to 122°C.
  • FTIR was used to monitor the SiH content of the mixture after 15 minutes and found that the SiH was completely consumed.
  • the solution was clear and stirred at RT for 10 minutes. Volatile components were removed using a rotary evaporator at 60°C and 0.5 mmHg for 30 minutes. A clear yellow photoluminescent liquid was transferred to a glass vial. Eu element content was estimated to be 4.9% based on the weights of raw materials and final product.
  • the product was compatible with polydimethylsiloxanes (350 cSt DOW CORNING® 200 fluid), vinyl-terminated polydimethylsiloxanes (DOW CORNING® SFD 119 Fluid), OH- terminated polydimethylsiloxanes (having a viscosity of 40 mm /sec at 25°C), vinyl- terminated polyphenylmethylsiloxanes (M Vl D phMe 2 5M Vl ), and OH-terminated
  • polyphenylmethylsiloxanes having a viscosity of 500 mm /sec at 25°C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)

Abstract

L'invention porte sur un organosiloxane qui possède la formule : (R1 3SiO)n(R1)(3-n)Si-R2-Si(R1)2OSi(R3)2X où n vaut 1 ou 2, R1 représente indépendamment un groupe hydrocarbyle monovalent en C1 à C20, R2 représente un groupe hydrocarbyle divalent en C2 à C12, R3 représente indépendamment un groupe hydrocarbyle monovalent en C1 à C30 contenant au moins un groupe aryle, X représente un groupe hydrolysable choisi parmi -OR4, Cl, -OC(O)R4, -N(R4)2 ou -ON=CR4 2 où R4 représente l'atome d'hydrogène ou un groupe alkyle en C1 à C6.
PCT/US2013/045069 2012-06-20 2013-06-11 Organopolysiloxanes monofonctionnels pour agents de compatibilité polyhétérosiloxanes WO2013191955A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105218575A (zh) * 2015-11-04 2016-01-06 威海新元化工有限公司 一种1-乙烯基-3-羟基-1,1,3,3-四甲基二硅氧烷的制备方法
CN108440592A (zh) * 2018-03-23 2018-08-24 威海新元化工有限公司 一种1,5-二乙烯基-1,1,3,3,5,5-六甲基三硅氧烷的制备方法

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US5364896A (en) 1991-11-26 1994-11-15 Dow Corning Toray Silicone Co., Ltd Method for preparing silica filled organosiloxane compositions
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WO2011002826A1 (fr) 2009-07-02 2011-01-06 Dow Corning Corporation Procédés de préparation de polyhétérosiloxanes
WO2012094450A1 (fr) * 2011-01-05 2012-07-12 Dow Corning Corporation Polyhétérosiloxanes pour des matières à indice de réfraction élevé

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US2823218A (en) 1955-12-05 1958-02-11 Dow Corning Process for the production of organo-silicon compounds
US3159601A (en) 1962-07-02 1964-12-01 Gen Electric Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes
US3220972A (en) 1962-07-02 1965-11-30 Gen Electric Organosilicon process using a chloroplatinic acid reaction product as the catalyst
US3296291A (en) 1962-07-02 1967-01-03 Gen Electric Reaction of silanes with unsaturated olefinic compounds
US3419593A (en) 1965-05-17 1968-12-31 Dow Corning Catalysts for the reaction of = sih with organic compounds containing aliphatic unsaturation
US3516946A (en) 1967-09-29 1970-06-23 Gen Electric Platinum catalyst composition for hydrosilation reactions
US3814730A (en) 1970-08-06 1974-06-04 Gen Electric Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105218575A (zh) * 2015-11-04 2016-01-06 威海新元化工有限公司 一种1-乙烯基-3-羟基-1,1,3,3-四甲基二硅氧烷的制备方法
CN108440592A (zh) * 2018-03-23 2018-08-24 威海新元化工有限公司 一种1,5-二乙烯基-1,1,3,3,5,5-六甲基三硅氧烷的制备方法

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