WO2005044828A1 - 環状有機ケイ素化合物の製造方法及びアルコール性水酸基を有するケイ素系樹脂及びその製造方法 - Google Patents

環状有機ケイ素化合物の製造方法及びアルコール性水酸基を有するケイ素系樹脂及びその製造方法 Download PDF

Info

Publication number
WO2005044828A1
WO2005044828A1 PCT/JP2004/016445 JP2004016445W WO2005044828A1 WO 2005044828 A1 WO2005044828 A1 WO 2005044828A1 JP 2004016445 W JP2004016445 W JP 2004016445W WO 2005044828 A1 WO2005044828 A1 WO 2005044828A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
organic silicon
organic
carbon atoms
resin
Prior art date
Application number
PCT/JP2004/016445
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Katsuhiko Komuro
Hiroshi Suzuki
Original Assignee
Toagosei Co., Ltd.
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 Toagosei Co., Ltd. filed Critical Toagosei Co., Ltd.
Priority to US10/577,948 priority Critical patent/US7402648B2/en
Priority to KR1020117013078A priority patent/KR101064063B1/ko
Priority to KR1020067008701A priority patent/KR101097570B1/ko
Priority to JP2005515324A priority patent/JP4470886B2/ja
Publication of WO2005044828A1 publication Critical patent/WO2005044828A1/ja

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
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • 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
    • 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
    • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
    • 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
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups

Definitions

  • the present invention relates to a method for producing a cyclic organic silicon compound, and more particularly, to a method for producing an alkoxysilane having a hydroxyl group protected by an organic substituent.
  • the present invention also relates to a novel organic gay resin having an alcoholic hydroxyl group and a method for producing the same.
  • the organic gay resin of the present invention is useful as a raw material such as a material for lithography and an organic-inorganic hybrid material.
  • Halogenosilanes and alkoxysilanes having a soluble group are useful as raw materials for lithography materials and organic-inorganic hybrid materials.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2002-224949
  • Patent Document 2 Japanese Unexamined Patent Application Publication No. 200 2-3 3 8583
  • the method known so far as a method for producing a halogenosilane or an alkoxysilane having a soluble group is a method utilizing a multi-step synthesis reaction. Not suitable.
  • Non-Patent Document 1 J. Org. Chem. 1997, 62, 4206-4207
  • Non-Patent Document 2 J. Org. Chem. 2002, 67, 2056-2064
  • Non-Patent Document 3 Non-Patent Document 4
  • Non-Patent Document 3 MakromolekulareChemie 1964, 73, 85
  • Non-Patent Document 4 MakromolekulareChemie 1966, 97, 241
  • Patent Document 1 Japanese Patent Laid-Open No. 8- No. 231 924
  • Patent Document 2 JP-A-9-176321
  • Patent Document 3 JP 2001-213963 A
  • Patent Document 4 JP 2003-146832A
  • an organic gay resin having an alicyclic epoxide is synthesized, and then an oxidation reaction (polymer reaction) is used to convert the organic gay resin having a diol into an organic gay resin having a diol. Conversion methods have also been reported (eg,
  • Patent Document 5
  • Patent Document 5 JP-A-10-87834 Further, polymethylsilsesquioxane-based fine particles having an alcoholic hydroxyl group have been reported (for example, Patent Document 6).
  • Patent Document 6 Japanese Patent Application Laid-Open No. Hei 1-11-1681
  • An organic gay resin having an alcoholic hydroxyl group is useful as a raw material for a lithography material, an organic-inorganic hybrid material, etc. because it exhibits an alkali-soluble group.
  • Patent Document 7 Japanese Patent Application Laid-Open No. 2003-149822
  • these resins can easily react with a silylating agent, and thus can be used as raw materials for various functional materials.
  • Non-Patent Document 1 J.0rg. Chem. 1997, 62, 4206
  • Non-Patent Document 2 J. Org. Chem. 2002, 67, 2056
  • Non-Patent Document 3 MakromolekulareChemie 1964, 73, 85
  • Non-Patent Document 4 MakromolekulareChemie 1966, 97, 241
  • Oxa-silacyclopentanes are useful as various organic synthetic intermediates, reactants, and resin raw materials because they generate an alcoholic hydroxyl group by performing a ring opening reaction.
  • synthesis of oxa-silacyclopentanes usually requires at least two steps of 1) hydrosilation of olefins with hydrosilane and 2) ring-closure reaction. Requires two or more reaction steps.
  • the present invention provides a process for synthesizing a cyclic organosilicon compound having a structure similar to that of oxa-silacyclopentanes by completing the reaction in a one-step reaction to obtain a target compound with high purity and high yield.
  • the task is to provide a law.
  • the alcoholic hydroxyl group easily reacts with silanol remaining in the resin, and the organic gay resin having the alcoholic hydroxyl group easily gels.
  • Another object of the present invention is to construct an organic gay resin having an alcoholic hydroxyl group which is easy to control the composition and does not change with time, and a method for producing the same. Means for solving the problem
  • the present invention relates to Invention 1 (hereinafter abbreviated as Invention 1) relating to a method for producing a cyclic organic gayne compound and Invention 2 (hereinafter referred to as Invention 2) relating to an organic gay resin containing an alcoholic hydroxyl group. Abbreviated).
  • the production method of the present invention 1 is characterized by reacting an olefin represented by the following general formula (1) and an alkoxysilane represented by the following general formula (2) in the presence of a transition metal catalyst.
  • This is a method for producing a cyclic organic gay compound represented by the following general formula (3).
  • Z represents an alkenyl group having 25 carbon atoms in which a terminal carbon atom C remote from the carbon atom to which the hydroxyl group is bonded forms a carbon-carbon unsaturated bond, and R is a methyl group or Me represents hydrogen, and Me represents a methyl group.
  • R represents an alkyl group or an alkoxyl group having 13 carbon atoms
  • R represents
  • Z ′ represents an alkylene group having 25 carbon atoms in which the carbon-carbon unsaturated bond of z is a saturated bond, the terminal carbon atom C of Z is bonded to a Si atom, and R is a methyl group or Represents hydrogen, R represents an alkyl group having 13 carbon atoms or an alkoxyl group, and R represents an alkyl group having 13 carbon atoms.
  • the use of a cyclic organic gayne compound such as oxa-silacyclopentane as a resin raw material allows easy control of the composition and stable alcoholic hydroxyl groups with no change over time.
  • the organic gay resin of the present invention 2 comprises a cyclic organic gay compound represented by the above general formula (3) (hereinafter, abbreviated as a cyclic organic gay compound [3]), or a polyfunctional alkoxysilane Is an organic gay resin having an alcoholic hydroxyl group obtained by hydrolyzing and condensing a mixture of the above.
  • a desirable raw material compound is a cyclic organic gayne compound (hereinafter abbreviated as DESMBO) in the above general formula (3) in which each substituent is as follows. It is.
  • a preferred production method for obtaining the organic gay resin of the present invention 2 is to prepare a cyclic organosilicon compound [3] or a mixture thereof with a polyfunctional alkoxysilane at a polymer concentration of 30%. This is a method in which hydrolysis and condensation are performed in an organic solvent while maintaining the concentration at not more than mass%.
  • a preferred production method comprises the following four steps.
  • Step (1) In an organic solvent, the cyclic organic gayne compound [3] or a mixture of the cyclic organic gayne compound and the polyfunctional alkoxysilane is hydrolyzed, and after adding an organic solvent, a dehydrating agent is added to dehydrate.
  • Step (2) After filtering the dehydrating agent, the silanol at the terminal of the resin is sealed with a silylating agent.
  • Step (3) After distilling off the solvent, an organic solvent and water are added to form an alcoholic hydroxyl group.
  • the organic gay resin to be washed with water.
  • Step (4) After adding a dehydrating agent and dehydrating the resin, the solvent is distilled off to obtain an organic gay resin having an alcoholic hydroxyl group.
  • a cyclic organic gayne compound having an alcoholic hydroxyl group and an alkoxyl group protected by an organic substituent can be synthesized by a one-step reaction.
  • a side reaction can be suppressed, and a target cyclic organosilicon compound can be obtained with high purity and high yield.
  • the cyclic organosilicon compound obtained by the present invention 1 has an alkoxysilyl group, it reacts with another organic gay compound (including a polymer) to form a lithiloxane bond, Coupling reaction with the silanol group in it is possible.
  • the cyclic organosilicon compound obtained according to the present invention 1 easily undergoes ring opening by a hydrolysis reaction to generate an alcoholic hydroxyl group, and the alcoholic hydroxyl group functions as an alkali-soluble group and a crosslinkable group. That is, it functions as a multi-reactive gay compound having a gay functional and a protected carbon functional group. Therefore, the cyclic organic gayne compound obtained by this production method is useful as an intermediate for organic synthesis, a raw material for resin synthesis, a modifier for resin, and a surface treatment agent for inorganic compounds.
  • a stable organic gay resin having an alcoholic hydroxyl group whose composition can be easily controlled and which does not change with time, can be obtained.
  • the present invention 1 relates to a method for producing a cyclic organic gay compound represented by the above general formula (3).
  • the present invention 1 will be described in detail.
  • the cyclic organic silicon compound represented by the general formula (3) is obtained by subjecting a hydroxyl-containing olefin (1) and an alkoxysilane (2) to a hydrosilation reaction in the presence of a transition metal catalyst. It is synthesized by performing a ring-closing condensation reaction (dealcoholization reaction).
  • these reactions can be performed instantaneously, so that side reactions hardly occur, and the target compound can be obtained in extremely high purity and high yield.
  • Olefins having a hydroxyl group are represented by the following general formula (1).
  • Z represents an alkenyl group having 25 carbon atoms in which a terminal carbon atom C far from the carbon atom to which the hydroxyl group is bonded forms a carbon-carbon unsaturated bond
  • R is a methyl group Or, it represents hydrogen, preferably a methyl group, and Me represents a methyl group.
  • olefins include 1-propene-3-methyl-3-ol, 1-butene-4-methyl-4-ol, 1-pentene-5-methyl-5-ol, 1-hexene- 6-methyl-6-ol, 1-butene-3-methyl-3 There are -ol, 1-penten-4-methyl-4-ol, 1-hexene-5-methyl-5-ol and 1-heptene-6-methyl-6-ol.
  • 1-butene-3-methyl-3-ol is most preferable because the raw material is easily obtained.
  • the alkoxysilanes are represented by the following general formula (2).
  • R represents an alkyl group or an alkoxyl group having 13 carbon atoms
  • R represents
  • alkoxysilanes include trimethoxy silane, triethoxy silane, tripropoxy silane, methyl dimethoxy silane, methyl ethoxy silane, methyl dipropoxy silane, methoxy diethoxy silane, methoxy dipropoxy.
  • Examples include silane, ethoxydipropoxysilane, methylmethoxyethoxysilane, and methylmethoxypropoxysilane.
  • R is an ethoxy group and R is an ethyl group.
  • the olefins of the above general formula (1) and the alkoxysilane of the above general formula (2) are subjected to a hydrosilylation reaction and a ring-closing condensation reaction in the presence of a transition metal catalyst. (Dealcoholization reaction).
  • the catalyst used in the present invention 1 is not particularly limited as long as it is known to promote the hydrolysis reaction.
  • Preferred catalysts include cobalt, nickel, ruthenium, rhodium, palladium, and iridium. And metals such as platinum, platinum, and other metals belonging to Groups 8 to 10; organometallic complexes; metal salts; and metal oxides.
  • platinum-based catalysts are used.
  • Preferred platinum-based catalysts include chloroplatinic acid hexahydrate (HPtCI-6H0), cis-PtCI (PhCN), platinum carbon, and divinyl chloride.
  • Platinum complexes (Pt-dvds) coordinated with loxane are exemplified.
  • Ph represents a phenyl group.
  • the amount of the catalyst to be used is preferably 0.1 ppm to 1,000 ppm with respect to the olefins represented by the general formula (1).
  • the preferred charge ratio of the olefins (1) and the alkoxysilane (2) is such that, based on 100 moles of the compound having a high boiling point, 110 mol The ratio is 20 moles.
  • the alkoxysilane (2) is a compound having a lower boiling point than the olefins (1), so that the alkoxysilane (2) is used in excess of the olefins (1).
  • reaction temperature since the control operation of the reaction temperature depends on external heating and the supply rate of the alkoxysilane, it cannot be determined unconditionally. However, usually, the reaction temperature is maintained in the range of 40 ° C to 120 ° C. The silylation reaction and the ring closure condensation reaction (dealcoholization reaction) can be smoothly continued.
  • the product obtained by the above reaction can be further purified by appropriately removing unreacted raw materials by a purification step such as distillation, so that the purity can be easily increased to 90% or more.
  • the cyclic organic gayne compound [3] synthesized as described above can be hydrolyzed under acid or basic conditions to form an organic gayne resin skeleton, and at the same time, introduce a hydroxyl group into the resin skeleton. it can.
  • the product of the hydrolysis-condensation is a polymer having the following repeating units.
  • R in the general formula (3) is an alkyl group having 13 carbon atoms
  • the repeating unit is [A] below,
  • Each of the repeating units [A] and [B] is characterized in that it has a hydroxyl group generated by opening the ring of the cyclic organic gay compound [3].
  • the organic gayne resin of the present invention can be obtained by, in addition to hydrolyzing and condensing a cyclic organic gayne compound [3] alone, a mixture of a cyclic organic gayne compound [3] and a polyfunctional alkoxysilane. Including those obtained by hydrolysis and co-condensation.
  • Preferable polyfunctional alkoxysilanes include 34-functional alkoxysilanes, preferably those comprising an alkyl group having 13 carbon atoms and Z or an alkoxy group having 13 carbon atoms.
  • Preferred trifunctional alkoxysilanes include, for example, triethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methyltriethoxysilane and the like.
  • a preferable ratio of the polyfunctional alkoxysilane is a ratio of not more than 10 mol per 1 mol of the cyclic organic gayne compound [3].
  • the preferred number average molecular weight of the organic gay resin of the present invention is 1 000 ⁇ 100
  • the preferred average molecular weight measured by GPC is 1,000,000.
  • Preferred acids include hydrochloric acid, nitric acid, sulfuric acid, acetic acid, formic acid and the like.
  • Preferred bases include sodium hydroxide, potassium hydroxide, lithium hydroxide, tetramethylammonium hydroxide, triethylamine, pyridine and the like.
  • the preferred amount of water used for the hydrolysis is greater than or equal to the stoichiometric amount, preferably 1.52 times the stoichiometric amount.
  • Preferred organic solvents used in the hydrolysis include acetone, methanol, ethanol, isopropyl alcohol, methyl ethyl ketone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, toluene, hexane, and the like. You may use it.
  • Preferred examples of the molecular weight modifier include hexamethyldisiloxane, tetramethyldisiloxane, hexaphenyldisiloxane, hexavinyldisiloxane, tetraphenyldimethyldisiloxane, and tetraisopropyldisiloxane.
  • Examples of the dehydrating agent after hydrolysis include anhydrous sodium sulfate and anhydrous magnesium sulfate.
  • the type of the dehydrating agent is not limited as long as it has a dehydrating effect and does not contaminate the resin.
  • the resin-terminated silanol is sealed with a silylating agent.
  • a silylating agent By sealing the silanol at the terminal of the resin, an organic gay resin having an alcoholic hydroxyl group which is stable over time can be constructed.
  • Preferred silylating agents include 1,1,1,3,3,3-hexamethyldisilazane, 1,1,3,3-tetramethyldisilazane, heptamethyldisilazane, 1,3-divinyl-1 1,1,3,3-tetramethyldisilazane, 1,1,3,3,5,5-hexamethylcyclotrisilazane, tris (trimethylsilyl) amine, bis (ethylamino) dimethylsilane, bis (dimethylamino) ) Dimethylsilane, bis (dimethylamino) diphenylsilane, bis (dimethylamino) methylphenylsilane, trimethylsi
  • aminosilanes such as lanol and t-butylaminotrimethylsilane
  • chlorosilanes such as silanols, trimethylchlorosilane, dimethylchlorosilane and phenylmethylchlorosi
  • the solvent is distilled off under reduced pressure, an organic solvent is added, and the organic garlic resin is washed with water.
  • organic solvent used for washing with water include acetone, methanol, ethanol, isopropyl alcohol, methyl ethyl ketone, methyl isobutyl ketone, propylene glycol monomethyl ether acetate, toluene, and hexane. You may use it.
  • Ultrapure water is generally used for water washing, but an acidic aqueous solution such as a hydrochloric acid aqueous solution, an alkaline aqueous solution such as a sodium hydroxide aqueous solution, or a saturated sodium chloride aqueous solution may be used. Washing with water is preferably performed until the aqueous layer becomes neutral.
  • an acidic aqueous solution such as a hydrochloric acid aqueous solution
  • an alkaline aqueous solution such as a sodium hydroxide aqueous solution
  • a saturated sodium chloride aqueous solution may be used. Washing with water is preferably performed until the aqueous layer becomes neutral.
  • the dehydrating agent to be used after washing with water include anhydrous sodium sulfate and anhydrous magnesium sulfate.
  • the type of the dehydrating agent is not particularly limited as long as it has a dehydrating effect and does not contaminate the resin.
  • a reactor (flask) provided with a cooling tube, a dropping funnel, and a magnetic stirrer was placed in an oil bath, and 1-butene-3-methyl-3-ol (30 g, 348 mmol) was charged and stirred.
  • Triethoxysilane (62.9 g, 383 mmol) was charged into the dropping funnel.
  • the triethoxysilane (11.2 mL) charged in the dropping funnel is poured into the flask, and the oil bath is set at 80 ° C.
  • Add 0.1 MPt-dvds xylene solution (13 to 0.0013 mmol) to the flask to start the reaction.
  • the colorless transparent liquid was subjected to 1 HN MR measurement at 270 MHz.
  • a reactor equipped with a dropping funnel and a magnetic stirrer was charged with DESMBO (49 g, 240 mmol), methyltriethoxysilane (78.6 g, 441 mmol), hexamethyldisiloxane (19.5 g, 120 mmol), and acetone (91 g). Stirred. A 1.5 wt% hydrochloric acid aqueous solution (37.4 g) was charged into the dropping funnel, and the solution was slowly dropped. After completion of the dropwise addition, the mixture was stirred at room temperature for 1.5 hours. Subsequently, diisopropyl ether (200 g) was added, and anhydrous magnesium sulfate was added, followed by dehydration for 2 hours.
  • DESMBO 49 g, 240 mmol
  • methyltriethoxysilane 78.6 g, 441 mmol
  • hexamethyldisiloxane (19.5 g, 120 mmol
  • acetone
  • the anhydrous magnesium sulfate is filtered off, hexamethyldisilazane (38.7 g, 240 mmol) is slowly added with stirring, and the mixture is stirred at room temperature for 2 hours, and the solvent is distilled off under reduced pressure.
  • Methyl ethyl ketone (200 g) and a 1N-hydrochloric acid aqueous solution are added, and the mixture is washed. The washing is repeated until the aqueous layer becomes neutral. After dehydration with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain an organic gay resin (73.3 g, 89%).
  • the organic gay resin was measured for 1 HN MR at 270 MHz, and the spectrum shown in FIG. 3 was obtained.
  • Table 3 shows the S values and their attributions. The compound thus obtained was confirmed to have the following structure.
  • Propylene glycol methyl ether acetate containing 0.5 wt% of water was prepared as a solvent.
  • the organic gay resin prepared in Example 1 was dissolved in a solvent at a concentration of 10 wt% to prepare a sample. This sample was left at 60 ° C for 3 days, and the change in molecular weight was monitored. Table 5 shows the results.
  • the production method of the present invention 1 is useful as a technique for inexpensively producing a cyclic organic gay compound having an alcoholic hydroxyl group and an alkoxyl group protected by an organic substituent.
  • the cyclic organosilicon compound obtained by the present invention 1 is useful as a resist raw material used in lithography.
  • the organic gay resin having an alcoholic hydroxyl group of the present invention 2 is useful as a raw material for lithography materials and organic-inorganic hybrid materials.
  • FIG. 1 is a 1 H-NMR spectrum of the compound obtained in Example 1.
  • FIG. 2 is a 13 C-NMR spectrum of the compound obtained in Example 1.
  • FIG. 3 shows a 1 H-NMR spectrum of the organic gay resin obtained in Example 1.
  • FIG. 4 shows a 1 -NMR spectrum of the organic gay resin obtained in Example 1.
  • Figure 5 shows the IR scan Bae spectrum of organic Gay fluororesin obtained in Example 1 c

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2004/016445 2003-11-07 2004-11-05 環状有機ケイ素化合物の製造方法及びアルコール性水酸基を有するケイ素系樹脂及びその製造方法 WO2005044828A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/577,948 US7402648B2 (en) 2004-11-05 2004-11-05 Method for producing cyclic organic silicon compound and organic silicon resin having alcoholic hydroxyl group
KR1020117013078A KR101064063B1 (ko) 2003-11-07 2004-11-05 알코올성 수산기를 갖는 규소계 수지 및 그의 제조 방법
KR1020067008701A KR101097570B1 (ko) 2003-11-07 2004-11-05 환상 유기 규소 화합물의 제조 방법
JP2005515324A JP4470886B2 (ja) 2003-11-07 2004-11-05 環状有機ケイ素化合物の製造方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2003-377752 2003-11-07
JP2003377752 2003-11-07
JP2004039063 2004-02-16
JP2004-039063 2004-02-16

Publications (1)

Publication Number Publication Date
WO2005044828A1 true WO2005044828A1 (ja) 2005-05-19

Family

ID=34575920

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2004/016445 WO2005044828A1 (ja) 2003-11-07 2004-11-05 環状有機ケイ素化合物の製造方法及びアルコール性水酸基を有するケイ素系樹脂及びその製造方法

Country Status (4)

Country Link
JP (2) JP4470886B2 (enrdf_load_stackoverflow)
KR (2) KR101064063B1 (enrdf_load_stackoverflow)
TW (1) TW200519120A (enrdf_load_stackoverflow)
WO (1) WO2005044828A1 (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007007598A1 (ja) * 2005-07-12 2007-01-18 Toagosei Co., Ltd. アルコ－ル性水酸基を有する有機ケイ素樹脂及びその製造方法
WO2014009204A1 (de) * 2012-07-11 2014-01-16 Wacker Chemie Ag Oxasilacyclen und verfahren zu deren herstellung
US9309358B2 (en) 2012-07-11 2016-04-12 Wacker Chemie Ag Crosslinkable siloxanes by acid-catalyzed polymerization of oxasilacycles

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07149901A (ja) * 1993-12-01 1995-06-13 Shin Etsu Chem Co Ltd 有機けい素化合物とその製造方法、および有機けい素化合物重合体
JP2003098670A (ja) * 2001-09-20 2003-04-04 Fujitsu Ltd レジスト組成物及びこれを用いたパターン形成方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07149901A (ja) * 1993-12-01 1995-06-13 Shin Etsu Chem Co Ltd 有機けい素化合物とその製造方法、および有機けい素化合物重合体
JP2003098670A (ja) * 2001-09-20 2003-04-04 Fujitsu Ltd レジスト組成物及びこれを用いたパターン形成方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
TROST B.M. ET AL.: "Markovnikov alkyne hydrosilylation catalyzed by ruthenium complexes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 123, no. 50, 2001, pages 12726 - 12727, XP002986953 *
WALKUP R.D. ET AL.: "Silicon functionalized silyl enol ethers. 4. Effects of fariations of aloxy substituents upon cyclizations of dialkoxy-2-chloroethylsilyl enol ethers to form 2,2-dialkoxy-1-oxa-2-silacyclohexanes", CHEMISTRY LETTERS, no. 7, 1990, pages 1055 - 1058, XP002986954 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007007598A1 (ja) * 2005-07-12 2007-01-18 Toagosei Co., Ltd. アルコ－ル性水酸基を有する有機ケイ素樹脂及びその製造方法
WO2014009204A1 (de) * 2012-07-11 2014-01-16 Wacker Chemie Ag Oxasilacyclen und verfahren zu deren herstellung
JP2015527312A (ja) * 2012-07-11 2015-09-17 ワッカー ケミー アクチエンゲゼルシャフトＷａｃｋｅｒ Ｃｈｅｍｉｅ ＡＧ オキサシラサイクルおよびこれらの製造方法
US9284340B2 (en) 2012-07-11 2016-03-15 Wacker Chemie Ag Oxasilacycles and method for the production thereof
US9309358B2 (en) 2012-07-11 2016-04-12 Wacker Chemie Ag Crosslinkable siloxanes by acid-catalyzed polymerization of oxasilacycles

Also Published As

Publication number Publication date
TWI341842B (enrdf_load_stackoverflow) 2011-05-11
KR20060111489A (ko) 2006-10-27
JP5062231B2 (ja) 2012-10-31
TW200519120A (en) 2005-06-16
KR20110070928A (ko) 2011-06-24
JP4470886B2 (ja) 2010-06-02
JP2010013653A (ja) 2010-01-21
KR101064063B1 (ko) 2011-09-08
JPWO2005044828A1 (ja) 2007-05-17
KR101097570B1 (ko) 2011-12-22

Similar Documents

Publication Publication Date Title
JP5740953B2 (ja) 有機ケイ素化合物の製造方法
JP5153635B2 (ja) 新規エポキシ化合物およびその製造方法
JP5115729B2 (ja) トリアルキルシリル基で保護されたアセト酢酸エステル基含有有機ケイ素化合物及びその製造方法
JP5664192B2 (ja) 有機ケイ素化合物の製造方法
JP5652829B2 (ja) 無水条件におけるシラノールの製造方法
JP5062231B2 (ja) アルコール性水酸基を有する有機ケイ素樹脂及びその製造方法
US7402648B2 (en) Method for producing cyclic organic silicon compound and organic silicon resin having alcoholic hydroxyl group
WO2007007597A1 (ja) 新規な有機ケイ素化合物及びその製造方法
JP4605018B2 (ja) 有機ケイ素化合物の製造方法並びにジオールを有する有機ケイ素樹脂及びその製造方法
WO2006021989A1 (ja) 有機ケイ素化合物の製造方法
JP2002020392A (ja) Ｎ−アルケニルアザシラシクロペンタン、およびその製造方法
WO2007007598A1 (ja) アルコ－ル性水酸基を有する有機ケイ素樹脂及びその製造方法
JP2004256503A (ja) 有機ケイ素化合物の製造方法
JP4172342B2 (ja) 環状有機ケイ素化合物及びその製造方法
JP4433563B2 (ja) 有機ケイ素化合物
JP4891536B2 (ja) アミノアリール基含有有機ケイ素化合物の製造方法、並びに、その中間体の製造方法
JP4013520B2 (ja) 新規なハロゲノシランおよびアルカリ可溶性樹脂
JP3257414B2 (ja) 環状エーテル基を有するオルガノポリシロキサン
JP2002193978A (ja) 新規な環状有機ケイ素化合物
JP3029691B2 (ja) オルガノシクロシロキサンおよびその製造方法
Miguel Faculty of Chemistry AMU
JP2002193975A (ja) アダマンチルエステル基を有する新規な有機ケイ素化合物
JPH04217690A (ja) オルガノシクロシロキサンおよびその製造方法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2005515324

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 1020067008701

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 2007055036

Country of ref document: US

Ref document number: 10577948

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 1020067008701

Country of ref document: KR

122 Ep: pct application non-entry in european phase
WWP Wipo information: published in national office

Ref document number: 10577948

Country of ref document: US