[go: up one dir, main page]

WO2010134340A1 - Procédé de fabrication d'un agent de couplage de type silane - Google Patents

Procédé de fabrication d'un agent de couplage de type silane Download PDF

Info

Publication number
WO2010134340A1
WO2010134340A1 PCT/JP2010/003380 JP2010003380W WO2010134340A1 WO 2010134340 A1 WO2010134340 A1 WO 2010134340A1 JP 2010003380 W JP2010003380 W JP 2010003380W WO 2010134340 A1 WO2010134340 A1 WO 2010134340A1
Authority
WO
WIPO (PCT)
Prior art keywords
propyl
dioxa
bis
silacyclooctane
group
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/JP2010/003380
Other languages
English (en)
Japanese (ja)
Inventor
暁 堀江
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.)
Bridgestone Corp
Original Assignee
Bridgestone Corp
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 Bridgestone Corp filed Critical Bridgestone Corp
Priority to JP2011514337A priority Critical patent/JPWO2010134340A1/ja
Publication of WO2010134340A1 publication Critical patent/WO2010134340A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages

Definitions

  • the present invention relates to a method for producing a silane coupling agent, and relates to a method for producing a silane coupling agent which is excellent in economic efficiency and can reduce the time required for the production process.
  • a technique for achieving both improvement in performance on a wet road surface of a tire and reduction in rolling resistance a technique of using an inorganic filler such as silica as a filler of a rubber composition used for a tire tread is known. It is known to be effective.
  • rubber compositions containing inorganic fillers such as silica reduce tire rolling resistance, improve braking performance on wet road surfaces, and improve steering stability, but have high unvulcanized viscosity and multi-stage kneading. Therefore, there is a problem in workability.
  • a rubber composition containing an inorganic filler such as silica the breaking strength and wear resistance are greatly reduced, and problems such as vulcanization delay and poor filler dispersion occur. Therefore, when an inorganic filler such as silica is blended with the rubber composition for tread, the unvulcanized viscosity of the rubber composition is reduced, the modulus and wear resistance are ensured, and the hysteresis loss is further reduced. It is essential to add a silane coupling agent.
  • the silane coupling agent is expensive, the blending cost increases due to the blending of the silane coupling agent.
  • the addition of a dispersion improver decreases the unvulcanized viscosity of the rubber composition and improves workability, but also reduces the wear resistance.
  • the dispersion improver is a highly ionic compound, a decrease in workability such as roll adhesion is also observed.
  • the present inventor even when an inorganic filler such as silica is blended as a filler, even when a conventional silane coupling agent is added, the hysteresis loss of the rubber composition is reduced and the wear resistance is reduced. It was found that the level of improvement could not be sufficiently satisfied and there was still room for improvement.
  • an object of the present invention is to provide a method for producing a silane coupling agent that solves the above-mentioned problems of the prior art, is excellent in economy, and can reduce the time required for the production process.
  • the present inventor when reacting an alcohol with a silane compound having a methoxysilyl group or an ethoxysilyl group, the reaction proceeds even under no catalyst, It has been found that a silane compound into which an alkoxyl group derived from the alcohol is introduced can be synthesized, and the present invention has been completed.
  • a silane compound (A) having a methoxysilyl group or an ethoxysilyl group is reacted with an alcohol in the absence of a catalyst to have an alkoxyl group derived from the alcohol. It includes a step of obtaining a silane compound (B).
  • the alcohol further has a nitrogen-containing functional group
  • the silane compound (B) has an aminoalkoxyl group
  • the nitrogen-containing functional group refers to a group containing a nitrogen atom, and examples thereof include an amino group, an imino group, a substituted amino group, a substituted imino group, and the aminoalkoxyl group.
  • the alkoxyl group containing this nitrogen-containing functional group is meant.
  • the reaction temperature in the absence of a catalyst is preferably in the range of 50 to 200 ° C, and more preferably in the range of 130 to 170 ° C.
  • the reaction time in the absence of a catalyst is preferably in the range of 1 to 12 hours.
  • silane compound (B) As said silane compound (B), following general formula (IV): [W in the formula (IV) is —NR 6 —, —O— or —CR 6 R 11 — (wherein R 11 is —R 7 or —C m H 2m —R 5 , where R 5 Is —NR 6 R 7 , —NR 6 —NR 6 R 7 or —N ⁇ NR 6 , R 6 is —C n H 2n + 1 , R 7 is —C q H 2q + 1 , m, n and q are each independently 0 to 20, and R 8 and R 9 are each independently represented by —M—C 1 H 2 1 — (wherein M is —O— or —CH 2 —, and 1 is 0 to 20), R 10 is represented by a methoxy group, an ethoxy group, or —M—C 1 H 2 1 —R 5 (where M, 1 and R 5 are as defined
  • the A 1 is a polysulfide group, a thioester group, a thiol group, a dithiocarbonate group, a dithioacetal group, a hemithioacetal group, a vinylthio group. , ⁇ -thiocarbonyl group, ⁇ -thiocarbonyl group, S—CO—CH 2 —O moiety, diketone group, and at least one selected from the group consisting of S—CH 2 —Si moieties.
  • the A 1 is represented by the following general formula (V), formula (VI) or formula (VII): [A 2 in the formula (V) is —S—CO—R 13 , —S—S—R 13 , —S—CS—O—R 13 , —R 14 —Cl, —R 14 —Br, — SH, —S—CO—O—R 13 , or —S—CO—CO—R 13 , wherein R 13 is —C r H 2r + 1 , R 14 is —C t H 2t —, r and t are each independently 0 to 20, R 12 in formula (V), formula (VI) and formula (VII) is —C t H 2t — (wherein t is 0 to 20), R 1 , R 2 and R 3 in the formula (VI) are as defined above, W, R 8 , R 9 and R 10 in formula (VII) have the
  • silane compound (B) 3-octanoylthio-propyl (monodimethylaminoethoxy) dimethoxysilane, 3-octanoylthio-propyl (didimethylaminoethoxy) monomethoxysilane, 3-octanoylthio-propyltridimethylaminoethoxysilane, 3-octanoylthio-propyl (monodiethylaminoethoxy) dimethoxysilane, 3-octanoylthio-propyl (didiethylaminoethoxy) monomethoxysilane, 3-octanoylthio-propyltridiethylaminoethoxysilane, 3- Octanoylthio-propyl (dimethylaminoethoxy) methoxymethylsilane, 3-octanoylthio-propyl (dimethylaminoeth
  • a silane compound (A) having a methoxysilyl group or an ethoxysilyl group and an alcohol in the absence of a catalyst by reacting a silane compound (A) having a methoxysilyl group or an ethoxysilyl group and an alcohol in the absence of a catalyst, the production cost is reduced and the time required for the production process is shortened.
  • a silane compound (B) having an alkoxyl group derived from the alcohol can be provided.
  • the present invention is described in detail below.
  • the method for producing a silane coupling agent of the present invention comprises a silane compound (A) having a methoxysilyl group or an ethoxysilyl group and an alcohol reacted in the absence of a catalyst to have an alkoxyl group derived from the alcohol. It includes the step of obtaining (B).
  • a silane compound into which an alkoxyl group derived from the alcohol is introduced by an alcohol exchange reaction between the silane compound in which the alkoxyl group is directly bonded to the silicon atom and the alcohol, titanium tetra n- Titanium alkoxide such as butoxide is used.
  • an alcohol exchange reaction can be performed even under non-catalytic conditions by changing the alkoxyl group of the raw silane compound to a methoxy group or an ethoxy group.
  • a silane compound into which an alcohol-derived alkoxyl group used as a reactant is introduced can be synthesized.
  • the silane compound (B) can efficiently develop a novel silane coupling agent by designing the structure of the alcohol used as a reactant.
  • an example of reaction formula which makes a silane compound (A) and alcohol react and obtains a silane compound (B) is shown below.
  • the silane compound (A) used in the method for producing a silane coupling agent of the present invention is not particularly limited as long as it has a methoxysilyl group or an ethoxysilyl group.
  • halogen or hydrogen can be used.
  • Silane compounds bonded to silicon atoms can also be used.
  • silane compound (A) following general formula (VIII): [In formula (VIII), at least one of R ′ 1 , R ′ 2 and R ′ 3 is represented by —O—C a H 2a + 1 (where a is 1 to 2), Represented by —M—C 1 H 2 + 1 (wherein M is —O— or —CH 2 —, l is 0 to 20), and A ′ 1 is a monovalent group].
  • a silane compound is preferred.
  • —O—C a H 2a + 1 is a methoxy group or an ethoxy group because a is 1 to 2
  • —C 1 H 2l + 1 is a group in which l is 0 to 20 Therefore, it is hydrogen or an alkyl group having 1 to 20 carbon atoms.
  • examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like.
  • the alkyl group may be linear or branched.
  • a ′ 1 is not particularly limited as long as it is a monovalent group.
  • a ′ 1 Thioester group, thiol group, dithiocarbonate group, dithioacetal group, hemithioacetal group, vinylthio group, ⁇ -thiocarbonyl group, ⁇ -thiocarbonyl group, S—CO—CH 2 —O moiety, diketone group, S—CH A group containing a 2- Si moiety or the like is preferable.
  • a ′ 1 is defined by the following formula (IX) or formula (X): [A 2 in the formula (IX) represents —S—CO—R 13 , —S—S—R 13 , —S—CS—O—R 13 , —R 14 —Cl, —R 14 —Br, — SH, —S—CO—O—R 13 , or —S—CO—CO—R 13 , wherein R 13 is —C r H 2r + 1 , R 14 is —C t H 2t —, r and t are each independently 0 to 20, R 12 in formula (IX) and formula (X) is —C t H 2t — (wherein t is 0 to 20),
  • R ′ 1 , R ′ 2 and R ′ 3 is represented by —O—C a H 2a + 1 (where a is 1 to 2), and the others are — M—C l H 2
  • —C r H 2r + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms because r is 0 to 20, and the alkyl group having 1 to 20 carbon atoms is as described above. It is as follows.
  • —C t H 2t — is a single bond or an alkylene group having 1 to 20 carbon atoms because t is 0 to 20.
  • examples of the alkylene group having 1 to 20 carbon atoms include a methylene group, an ethylene group, a trimethylene group, and a propylene group.
  • the alkylene group may be linear or branched.
  • x in the formula (X) is 1 to 10, preferably 2 to 4. Note that -C a H 2a + 1 and -C l H 2l + 1 are as described above.
  • silane compound (A) examples include trimethoxysilane, octyl (monomethyl) dimethoxysilane, 3-chloro-propyl (monomethyl) dimethoxysilane, 3-mercapto-propyl (monomethyl) dimethoxysilane, and 3-octanoylthio-propyl.
  • the alcohol reacted with the silane compound (A) in the absence of a catalyst is not particularly limited. From the viewpoint of improving ring efficiency, an alcohol having a nitrogen-containing functional group is preferred.
  • the alcohol reacted with the silane compound (A) in the absence of a catalyst is represented by the following formula: [Wherein R a and R b are each independently a monovalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may be linear or branched. R c and R d are each independently a divalent saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group may be linear or branched. In particular, dimethylaminoethanol, diethylaminoethanol, dibutylaminoethanol, N-methyldiethanolamine, N-butyldiethanolamine, N-lauryldiethanolamine and the like are preferable. .
  • the amount of alcohol used is preferably in the range of 0.9 to 1.1 molar equivalents per mole of silyl groups of the starting silane compound, and particularly preferably 1 molar equivalent. If the amount of alcohol used per mole of silyl group in the raw material silane compound is less than 1 molar equivalent, the reaction will not be completed. On the other hand, if it exceeds 1 molar equivalent, impurities may be produced.
  • a solvent can be used in a reaction without a catalyst.
  • the solvent include hexane, benzene, toluene, xylene, chloroform, dichloromethane, tetrahydrofuran, N, N-dimethylformamide and the like.
  • the reaction temperature is preferably in the range of 50 to 200 ° C., and more preferably in the range of 130 to 170 ° C. in the reaction without a catalyst. If the reaction temperature in the absence of a catalyst is within the specified range, the reaction rate can be increased. Further, when the reaction temperature in the absence of a catalyst is less than 50 ° C., the reaction may hardly proceed. On the other hand, when the reaction temperature exceeds 200 ° C., impurities may be generated.
  • the reaction time is preferably in the range of 1 to 12 hours in the reaction without a catalyst. If the reaction time under non-catalyst is within the above specified range, the yield of the product (silane compound (B)) can be sufficiently secured. In addition, if the reaction time in the absence of a catalyst is less than 1 hour, the reaction may not be completed, and if it exceeds 12 hours, impurities may be generated.
  • the silane compound (B) obtained by the method for producing a silane coupling agent of the present invention is a silane compound having an alkoxyl group derived from the alcohol. Moreover, it is preferable that the said alkoxyl group is an amino alkoxyl group from a viewpoint of adding to an inorganic filler compounded rubber composition and improving a coupling efficiency. More specifically, the silane compound (B) is preferably a compound represented by the above formula (I) and a compound represented by the above formula (IV).
  • R 1 , R 2 and R 3 are represented by the above general formula (II) or formula (III), and the other is a methoxy group or an ethoxy group.
  • M is —O— in one or more of R 1 , R 2 and R 3 .
  • M is —O— or —CH 2 —
  • l is 0 to 20, preferably 0 to 10.
  • m is 0 to 20, preferably in the range of 0 to 10.
  • —C m H 2m + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms because m is 0 to 20.
  • examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like.
  • the alkyl group may be linear or branched.
  • alkylene group having 1 to 20 carbon atoms examples include a methylene group, an ethylene group, a trimethylene group, and a propylene group.
  • the alkylene group may be linear or branched.
  • X and Y are each independently —O—, —NR 6 — or —CH 2 —.
  • R 6 is —C n H 2n + 1
  • n is 0 to 20, preferably in the range of 0 to 10.
  • —C n H 2n + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms because n is 0 to 20.
  • R 4 is —OR 6 , —NR 6 R 7 or —R 6 .
  • R 6 is —C n H 2n + 1
  • R 7 is —C q H 2q + 1
  • n and q are each independently 0 to 20, preferably 0 to 10. .
  • —C n H 2n + 1 is as described above, and —C q H 2q + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms because q is 0 to 20.
  • the alkyl group having 1 to 20 carbon atoms is as described above.
  • R 5 is —NR 6 R 7 , —NR 6 —NR 6 R 7, or —N ⁇ NR 6 .
  • R 6 is —C n H 2n + 1
  • R 7 is —C q H 2q + 1
  • n and q are each independently 0 to 20, preferably 0 to 10. .
  • -C n H 2n + 1 and -C q H 2q + 1 are as described above.
  • a 1 is a monovalent group. From the viewpoint of improving the coupling efficiency by adding to the inorganic filler-containing rubber composition, polysulfide group, thioester group, thiol group, Dithiocarbonate group, dithioacetal group, hemithioacetal group, vinylthio group, ⁇ -thiocarbonyl group, ⁇ -thiocarbonyl group, S—CO—CH 2 —O moiety, diketone group, S—CH 2 —Si moiety, etc. It is preferable to include. From the same viewpoint, the A 1 is preferably represented by the general formula (V), formula (VI) or formula (VII).
  • r is 0 to 20, preferably 0 to 10.
  • t is 0 to 20, The range of is preferable.
  • —C r H 2r + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms, and the alkyl group having 1 to 20 carbon atoms is as described above.
  • t is 0 to 20, —C t H 2t — is a single bond or an alkylene group having 1 to 20 carbon atoms.
  • the alkylene group having 1 to 20 carbon atoms is as described above.
  • R 1 , R 2 and R 3 in the formula (VI) are as defined above, and W, R 8 , R 9 and R 10 in the formula (VII) are the formulas described in detail later. It is synonymous with that defined in (IV). Furthermore, x in the formulas (VI) and (VII) is 1 to 10, preferably 2 to 4.
  • W is represented by —NR 6 —, —O— or —CR 6 R 11 —, wherein R 11 is —R 7 or —C m H 2m —R 5 .
  • R 5 is —NR 6 R 7 , —NR 6 —NR 6 R 7 , or —N ⁇ NR 6
  • R 6 is —C n H 2n + 1
  • R 7 is —C q H 2q + 1
  • m, n and q are each independently 0 to 20, preferably 0 to 10.
  • —C m H 2m — is a single bond or an alkylene group having 1 to 20 carbon atoms because m is 0 to 20.
  • examples of the alkylene group having 1 to 20 carbon atoms include a methylene group, an ethylene group, a trimethylene group, and a propylene group.
  • the alkylene group may be linear or branched.
  • —C n H 2n + 1 and —C q H 2q + 1 are hydrogen or an alkyl group having 1 to 20 carbon atoms because n and q are 0 to 20.
  • examples of the alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tridecyl group, tetradecyl group, Examples include a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and the like.
  • the alkyl group may be linear or branched.
  • R 8 and R 9 are each independently represented by —M—C 1 H 2l —, and R 10 is represented by a methoxy group, an ethoxy group or —M—C 1 H 2l —R 5 .
  • M is —O— or —CH 2 —
  • R 5 is —NR 6 R 7 , —NR 6 —NR 6 R 7 , or —N ⁇ NR 6
  • R 6 is —C In n H 2n + 1
  • R 7 is —C q H 2q + 1
  • l, n and q are each independently 0 to 20, preferably in the range of 0 to 10.
  • M is —O—.
  • —C 1 H 2l — is a single bond or an alkylene group having 1 to 20 carbon atoms because l is 0 to 20, and the alkylene group having 1 to 20 carbon atoms is as described above.
  • -C l H 2l + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms because l is 0 to 20.
  • the alkyl group having 1 to 20 carbon atoms is as described above.
  • -C n H 2n + 1 and -C q H 2q + 1 are as described above.
  • a 1 is a monovalent group. From the viewpoint of improving coupling efficiency by adding to an inorganic filler-containing rubber composition, polysulfide group, thioester group, thiol group, Dithiocarbonate group, dithioacetal group, hemithioacetal group, vinylthio group, ⁇ -thiocarbonyl group, ⁇ -thiocarbonyl group, S—CO—CH 2 —O moiety, diketone group, S—CH 2 —Si moiety, etc. It is preferable to include. From the same viewpoint, the A 1 is preferably represented by the general formula (V), formula (VI) or formula (VII).
  • r is 0 to 20, preferably 0 to 10.
  • t is 0 to 20, The range of is preferable.
  • —C r H 2r + 1 is hydrogen or an alkyl group having 1 to 20 carbon atoms, and the alkyl group having 1 to 20 carbon atoms is as described above.
  • t is 0 to 20, —C t H 2t — is a single bond or an alkylene group having 1 to 20 carbon atoms.
  • the alkylene group having 1 to 20 carbon atoms is as described above.
  • R 1 , R 2 and R 3 in formula (VI) are as defined in formula (I) above, and W, R 8 , R 9 and R 10 in formula (VII) are as defined above. It is synonymous with.
  • x in the formulas (VI) and (VII) is 1 to 10, preferably 2 to 4.
  • Silane Compound (B) includes 3-octanoylthio-propyl (monodimethylaminoethoxy) dimethoxysilane, 3-octanoylthio-propyl (didimethylaminoethoxy) monomethoxysilane, and 3-octanoylthio-propyltridimethyl.
  • Example 1 Provide of 3-mercaptopropyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane>
  • 18.0 g of 3-mercaptopropyldimethoxymethylsilane and 11.9 g of N-methyldiethanolamine were dissolved in 200 mL of xylene under a nitrogen atmosphere.
  • the temperature was raised to 150 ° C. and stirred for 10 hours.
  • Example 2 ⁇ Production of 3-mercaptopropyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane> Under a nitrogen atmosphere, 11.9 g of N-methyldiethanolamine was dissolved in 18.0 g of 3-mercaptopropyldimethoxymethylsilane in a 500 mL four-necked eggplant flask. The temperature was raised to 150 ° C. and stirred for 6 hours. Then, the remaining volatile components are removed with a rotary pump (10 Pa) and a cold trap (dry ice + ethanol), and 3-mercaptopropyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane 21.4 is removed.
  • Example 4 Provide of 3-ethyloxalylthio-propyl (methyl) 1,3-dioxa-6-methylaza-2-silacyclooctane>
  • 26.2 g of 3-ethyloxalylthio-propyldimethoxymethylsilane and 11.2 g of N-methyldiethanolamine were dissolved in 200 mL of xylene under a nitrogen atmosphere.
  • the temperature was raised to 150 ° C. and stirred for 7 hours.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)

Abstract

L'invention porte sur un procédé de fabrication d'un agent de couplage de type silane qui présente un rendement économique élevé et qui permet de réduire le temps nécessaire à la fabrication. Plus particulièrement, le procédé de fabrication d'un agent de couplage de type silane est caractérisé en ce qu'il comporte une étape de réaction d'un composé silane (A) ayant un groupe méthoxysilyle ou un groupe éthoxysilyle avec un alcool en l'absence de tout catalyseur afin de produire un composé silane (B) ayant un groupe alcoxyle issu de l'alcool. Dans le procédé, il est préféré que l'alcool ait, de plus, un groupe fonctionnel azoté et que le composé silane (B) ait un groupe aminoalcoxyle.
PCT/JP2010/003380 2009-05-20 2010-05-19 Procédé de fabrication d'un agent de couplage de type silane Ceased WO2010134340A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2011514337A JPWO2010134340A1 (ja) 2009-05-20 2010-05-19 シランカップリング剤の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009122587 2009-05-20
JP2009-122587 2009-05-20

Publications (1)

Publication Number Publication Date
WO2010134340A1 true WO2010134340A1 (fr) 2010-11-25

Family

ID=43126032

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2010/003380 Ceased WO2010134340A1 (fr) 2009-05-20 2010-05-19 Procédé de fabrication d'un agent de couplage de type silane

Country Status (2)

Country Link
JP (1) JPWO2010134340A1 (fr)
WO (1) WO2010134340A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011122128A (ja) * 2009-11-13 2011-06-23 Sumitomo Rubber Ind Ltd タイヤ用ゴム組成物及び空気入りタイヤ

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08311078A (ja) * 1995-05-17 1996-11-26 Yokohama Rubber Co Ltd:The オキサゾリジンシリルエーテル化合物の製造方法
JP2007051146A (ja) * 2005-08-17 2007-03-01 Degussa Ag 有機珪素化合物、その製造および該化合物の使用
JP2008169157A (ja) * 2007-01-12 2008-07-24 Dow Corning Toray Co Ltd ビス（シラトラニルアルキル）ポリスルフィド等の製造方法およびビス（シラトラニルアルキル）ポリスルフィド等の混合物
WO2009104766A1 (fr) * 2008-02-22 2009-08-27 株式会社ブリヂストン Composé organique du silicium et compositions de caoutchouc, pneusmatiques, compositions d'apprêt, compositions de peinture et adhésifs l'utilisant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08311078A (ja) * 1995-05-17 1996-11-26 Yokohama Rubber Co Ltd:The オキサゾリジンシリルエーテル化合物の製造方法
JP2007051146A (ja) * 2005-08-17 2007-03-01 Degussa Ag 有機珪素化合物、その製造および該化合物の使用
JP2008169157A (ja) * 2007-01-12 2008-07-24 Dow Corning Toray Co Ltd ビス（シラトラニルアルキル）ポリスルフィド等の製造方法およびビス（シラトラニルアルキル）ポリスルフィド等の混合物
WO2009104766A1 (fr) * 2008-02-22 2009-08-27 株式会社ブリヂストン Composé organique du silicium et compositions de caoutchouc, pneusmatiques, compositions d'apprêt, compositions de peinture et adhésifs l'utilisant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
I. P. URTANE ET AL.: "Nitrogen containing organosilicon compounds. CXIX. Synthesis of cyclic organosilicon esters of diethanolamines", ZEITSCHRIFT FUER ANORGANISCHE UND ALLGEMEINE CHEMIE, vol. 520, 1985, pages 179 - 195 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011122128A (ja) * 2009-11-13 2011-06-23 Sumitomo Rubber Ind Ltd タイヤ用ゴム組成物及び空気入りタイヤ

Also Published As

Publication number Publication date
JPWO2010134340A1 (ja) 2012-11-08

Similar Documents

Publication Publication Date Title
JP5334848B2 (ja) ケイ素含有のカップリング試薬からなる混合物
KR100853604B1 (ko) 메르캅토실란
JP4200002B2 (ja) 充填剤入りエラストマー組成物用炭化水素コアポリスルフィドシランカップリング剤
EP2471798B1 (fr) Procédé de production d'agents de couplage silane
KR101350003B1 (ko) 유기규소 화합물, 그의 제법 및 용도
KR20040111135A (ko) 유기규소 화합물
JPH09169774A (ja) ビス（シリルアルキル）ジスルファンの製造法
EP1244676A1 (fr) Silane contenant du soufre comme agents de couplage
JPH11158192A (ja) 短鎖ポリスルフィドシラン混合物の製造方法
JPH11349594A (ja) 短鎖ポリスルフィドシラン混合物の製造方法
EP2552925A1 (fr) Procédé de production d'azodicarbamides contenant du silicium
JP2011046641A (ja) シランカップリング剤の製造方法
WO2010134340A1 (fr) Procédé de fabrication d'un agent de couplage de type silane
WO2010134339A1 (fr) Procédé de fabrication d'un agent de couplage de type silane
JP7322762B2 (ja) ケチミン構造を有する有機ケイ素化合物の製造方法
US5936112A (en) Mixtures consisting of bis (silylorganyl) polysulfans and silyorganylthiocyanates, their production, and use
JP5699990B2 (ja) ピペラジニル基を有するオルガノキシシラン化合物の製造方法及びピペラジン化合物
JP6885294B2 (ja) 多環式アミノシラン化合物およびその製造方法
WO2010134337A1 (fr) Procédé pour la production d'un agent de couplage silane
JP4143821B2 (ja) ポリスルフィドシランの製造方法
JP2011046642A (ja) シランカップリング剤の製造方法
JP4143822B2 (ja) ポリスルフィドシランの製造方法
KR102067785B1 (ko) 아미노알킬실란 화합물의 제조 방법 및 이러한 방법에 의해 제조된 아미노알킬실란 화합물
JP4801135B2 (ja) アミノアルキルシランの製造方法
CN112513055A (zh) 硫醚硅烷、其生产方法及其用途

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10777577

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2011514337

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10777577

Country of ref document: EP

Kind code of ref document: A1