• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention relates to a novel branched siloxane-silalkylene copolymer represented by the following formula (1) containing a plurality of silicon atom bonded hydrogen atoms or silicon atom bonded alkoxy groups in a molecule: Where R 1 is an alkyl or aryl group having 1 to 10 carbon atoms, a is 3 or 4, X 1 is a silylalkyl group represented by the following formula (2) when i is 1. (Wherein R 1 is an alkyl or aryl group having 1 to 10 carbon atoms, R 2 is an alkylene group having 2 to 10 carbon atoms, R 3 is an alkyl group having 1 to 10 carbon atoms, X i + 1 is a hydrogen atom or the silylalkyl group, i is an integer of 1 to 10 representing the hierarchical increase in the silylalkyl group, b i is an integer of 0 to 3)
    公开号:KR19990071381A
    申请号:KR1019980034637
    申请日:1998-08-26
    公开日:1999-09-27
    发明作者:마코토 요시타케
    申请人:이이즈까 고지；도레이 다우 코닝 실리콘 가부시끼가이샤；
    IPC主号:
    专利说明:

    Branched siloxane-silalkylene copolymer
    The present invention relates to a novel branched siloxane-silalkylene copolymer containing a plurality of silicon atom bonded hydrogen atoms or silicon atom bonded alkoxy groups in a molecule.
    The organosilicon polymer containing the hydrogen atom couple | bonded with the some silicon atom in the molecule | numerator is used as a crosslinking agent of the crosslinking reaction by hydrosilylation reaction, or the precursor of functional organosilicon polymer synthesis | combination. Recently, a novel crosslinking agent obtained by forming a cured product having not only high crosslinking efficiency but also various properties such as mechanical strength, adhesion, and durability, and a novel precursor for synthesizing a functional organosilicon polymer having a special reactivity Development is desired, and various organic diatom polymers having a hydrogen atom bonded to a plurality of silicon atoms in one molecule have been proposed for this purpose (see Patent Publications No. 86-195129 and Patent Publication Nos. 94-107671). . However, even when such an organosilicon polymer was used as a crosslinking agent or a precursor, the results were not sufficiently satisfactory.
    On the other hand, it is known that the organosilicon polymer containing the alkoxy group couple | bonded with the some silicon atom in the molecule | numerator is used as a raw material of a coating agent, a coating vehicle, or a crosslinking agent of a moisture hardening composition. In particular, in recent years, there has been a demand for the development of organosilicon polymers that are highly reactive and effective for improving various properties such as mechanical strength, adhesion, and durability of the final product.
    In addition, a polymer having a resinous shape is known as an organosilicon polymer having a special structure (see Patent Publication No. 95-17981), and as a method for producing an addition reaction of tetravinylsilane and organochlorosilane as a manufacturing method thereof, there has been proposed. Tetravinylsilane, which is a raw material, is a special compound, and thus the organosilicon polymer has a disadvantage in that industrial utility is small. In particular, although the organosilicon polymer thereof contains a silicon atom-bonded hydrogen atom, there is a disadvantage that it is not possible to contain an alkoxy group in the polymer by the above production method.
    MEANS TO SOLVE THE PROBLEM This inventor reached | attained this invention as a result of earnestly examining in order to solve the said problem.
    It is an object of the present invention to provide novel branched siloxane-silalkylene copolymers containing a plurality of silicon atom bonded hydrogen atoms or silicon atom bonded alkoxy groups in a molecule.
    1 is a 29 Si-nuclear magnetic resonance spectrum of the branched siloxane-silalkylene copolymer obtained in Example 1. FIG.
    2 is a 29 Si-nuclear magnetic resonance spectrum of the branched siloxane-silalkylene copolymer obtained in Example 2. FIG.
    3 is a 29 Si-nuclear magnetic resonance spectrum of the branched siloxane-silalkylene copolymer obtained in Example 3. FIG.
    4 is a 29 Si-nuclear magnetic resonance spectrum of the branched siloxane-silalkylene copolymer obtained in Example 4. FIG.
    5 is a 29 Si-nuclear magnetic resonance spectrum of the branched siloxane-silalkylene copolymer obtained in Example 5. FIG.
    The present invention relates to branched siloxane-silalkylene copolymers represented by the following general formula (1):
    Formula 1
    Where
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    a is 3 or 4,
    X 1 is a silylalkyl group represented by the following formula (2) when i is 1.
    Formula 2
    (Wherein
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    R 2 is an alkylene group having 2 to 10 carbon atoms,
    R 3 is an alkyl group having 1 to 10 carbon atoms,
    X i + 1 is a hydrogen atom or the silylalkyl group,
    i is an integer of 1 to 10 representing the hierarchy of the silylalkyl group,
    b i is an integer of 0 to 3)
    The branched siloxane-silalkylene copolymer of the present invention is represented by the following general formula (1):
    Formula 1
    In the above formula, R 1 is an alkyl group or an aryl group having 1 to 10 carbon atoms, and as the alkyl group, methyl group, ethyl group, propyl group, butyl group, pentyl group, isopropyl group, isobutyl group, cyclopentyl group, cyclohexyl group And an aryl group includes a phenyl group and a naphthyl group. Among these, a methyl group is preferable. a is 3 or 4. X 1 is represented by the following formula (2) when i is 1.
    Formula 2
    Where
    R 2 is an alkylene group having 2 to 10 carbon atoms, and a linear alkylene group such as ethylene group, propylene group, butylene group, hexylene group, etc .; Branched alkylene groups, such as a methyl methylene group, a methyl ethylene group, a 1-methyl pentylene group, and a 1, 4- dimethyl butylene group, are mentioned. Among these, an ethylene group, a methyl methylene group, a hexylene group, a 1-methylpentylene group, and a 1, 4- dimethyl butylene group are preferable. R 3 is an alkyl group having 1 to 10 carbon atoms, and there are a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and an isopropyl group. Among these, a methyl group or an ethyl group is preferable. R 1 is the same as above. X i + 1 is a hydrogen atom or the silylalkyl group, but X i + 1 located at the terminal of the molecular chain is a hydrogen atom. i is an integer of 1 to 10, which represents the number of layers of the silylalkyl group, that is, the number of repetitions of the silylalkyl group. Therefore, when the number of layers is 1, the branched siloxane-silalkylene copolymer of the present invention is represented by the following formula (3), and when the number of layers is 2, the branched siloxane-silalkylene copolymer of the present invention is represented by the following formula (4) When the number of layers is 3, the branched siloxane-silalkylene copolymer of the present invention is represented by the following Formula 5:

    In the above formula, the sum of b 1 in one molecule is less than (3 × a).
    In the above formula, the sum of b 1 in one molecule is less than (3 × a), and the sum of b 2 is less than {3 × a × (3-b 1 )}.
    In addition, b i is an integer of 0-3.
    Such branched siloxane-silalkylene copolymers of the present invention are obtained as single compounds or mixtures thereof, and are specifically represented by the following average molecular formula:



    The branched siloxane-silalkylene copolymers of the present invention can be prepared, for example, by alternating one or more of the following steps (x) and (y).
    (x) represents a siloxane represented by the following formula or a branched siloxane-silalkylene copolymer produced in the following process (y) and a general formula R 4 -Si (OR 3 ) 3 , wherein R 3 is the same as above , R 4 is an alkenyl group having from 2 to 10 carbon atoms) by addition reaction of an alkenyl group-containing alkoxysilane in the presence of a platinum-based transition metal catalyst to alkoxy group-blocked branched siloxane-silalkylene copolymer It is a process of manufacturing;
    Wherein R 1 and a are the same as above.
    (y) is a branched siloxane containing a silicon atom-bonded hydrogen atom by reacting the branched siloxane-silalkylene copolymer obtained in the step (x) with a disiloxane of the compound of the following formula in the presence of an acidic aqueous solution: A process for preparing a silalkylene copolymer is as follows:
    Wherein R 1 is the same as above.
    In this process, a branched siloxane-silalkylene copolymer in which the molecular chain ends are sealed with an alkoxy group can be obtained by performing the (x) process at last, and finally, silicon at the molecular chain ends by the (y) process. Branched siloxane-silalkylene copolymers containing atomically bonded hydrogen atoms can be obtained.
    Platinum-based transition metal catalysts used in the step (x) include platinum chloride, alcohol-modified platinum chloride, olefin complexes of platinum and diketonate complexes of platinum. In carrying out the addition reaction using such a platinum-based transition metal catalyst, in order to completely react the silicon atom-bonded hydrogen atoms in the raw material, a slight excess of alkenyl group with respect to the silicon compound containing the silicon atom-bonded hydrogen atoms It is preferable to react the containing alkoxysilane. The excess alkenyl group-containing alkoxysilane can be fractionally recovered after the reaction by distillation under reduced pressure or the like. In addition, this addition reaction can be carried out at room temperature or heating conditions, it can be carried out using a solvent that does not inhibit the reaction.
    In the step (y), the reaction is preferably carried out by dropping the branched siloxane-silalkylene copolymer obtained in the step (x) in a mixture of the disiloxane and the acidic aqueous solution. In this case, it is preferable to use 1 mol or more of disiloxane with respect to 1 mol of alkoxy groups in the said copolymer. As for reaction temperature, 50 degreeC or more is preferable. In addition, by carrying out a reaction in which a hydrophilic solvent such as methanol, ethinol, isopropanol and the like coexist, the reaction can proceed efficiently. After the reaction, the organic layer can be separated, and then distilled under reduced pressure, whereby the remaining branched siloxane-silalkylene copolymer can be recovered with high purity.
    Specifically, for example, the following formula
    Tetrakis (dimethylsiloxy) silane represented by the above is used as a raw material, and vinyltrimethoxysilane is further reacted in the presence of a platinum catalyst.
    The reaction compound containing 12 silicon atom-bonded methoxy groups represented by this is obtained. Subsequently, it was added dropwise into a mixture of 1,1,3,3-tetramethyldisiloxane and an aqueous hydrochloric acid solution and reacted.
    A branched siloxane-silalkylene copolymer having an average of 8.6 silicon atom bonded hydrogen atoms and an average of 3.4 silicon atom bonded methoxy groups in one molecule is obtained. In addition, when vinyl trimethoxysilane is reacted with such a branched siloxane-silalkylene copolymer in the presence of a platinum catalyst, the following average molecular formula
    A branched siloxane-silalkylene copolymer having an average of 29 silicon atom bonded methoxy groups in one molecule is obtained. In particular, the branched siloxane-silalkylene copolymer thereof is added dropwise to the mixture of 1,1,3,3-tetramethyldisiloxane and an aqueous hydrochloric acid solution to react the same, and the following average molecular formula
    A branched siloxane-silalkylene copolymer having an average of 17.9 silicon atom bonded hydrogen atoms and an average of 11.1 silicon atom bonded methoxy groups in one molecule is obtained. In particular, when vinyltrimethoxysilane is reacted with such a branched siloxane-silalkylene copolymer in the presence of a platinum catalyst, the following average molecular formula
    A branched siloxane-silalkylene copolymer having an average of 65 silicon atom-bonded methoxy groups in one molecule can be produced.
    Furthermore, in the method for producing the same, in the step (y), a silicon atom-bonded hydrogen atom may be alcohol-decomposed to contain a small amount of the following monoalkoxysiloxy group as X i :
    Wherein R 1 and R 3 are the same as above.
    As described above, the branched siloxane-silalkylene copolymer of the present invention is characterized by containing a plurality of silicon atoms bonded to a hydrogen atom or a silicon atom bonded alkoxy group in a molecule. In particular, when it contains a silicon atom-bonded hydrogen atom, it is used as a crosslinking agent of a hydrosilylation reaction curable composition, or as a precursor for functional organosilicon polymer synthesis, and when it contains a silicon atom-bonded alkoxy group, it is reactive This is high and has the advantage of being used as a raw material of a coating agent or a coating vehicle or as a crosslinking agent of a moisture curable composition.
    Hereinafter, an Example demonstrates this invention. In the examples, the identification of the branched siloxane-silalkylene copolymers of the present invention was performed by 29 Si-nuclear magnetic resonance analysis and gel permeation chromatography analysis (solvent: toluene).
    Example 1
    Into a 200 ml four-necked flask equipped with a stirring device, a thermometer, a reflux condenser and a dropping lot, 103.6 g of vinyltrimethoxysilane and 0.04 g of 3% isopropanol solution of chloroplatinic acid were added and heated to 100 ° C while stirring. . Then, 49.4 g of tetrakis (dimethylsiloxy) silane was slowly added dropwise thereto so that the reaction temperature was maintained at 100 to 110 ° C using a dropping lot. After completion of the dropwise addition, the reaction solution was heated at 120 ° C. for 1 hour. After cooling, the reaction solution was transferred to a branched flask and concentrated under reduced pressure by a rotary evaporator to give 138.4 g of a pale brown liquid. Subsequently, in a 1 L four-necked flask equipped with a stirring device, a thermometer, a reflux condenser, and a dropping lot, 141.0 g of 1,1,3,3-tetramethyldisiloxane, 100 ml of concentrated hydrochloric acid, 200 ml of water and 200 isopropanol 200 Ml was added and stirred. Then, 80.6 g of the slightly brown liquid obtained above was slowly added dropwise over 1 hour using the dropping lot. After completion of the dropwise addition, the reaction solution was stirred at room temperature for 1 hour. Subsequently, the reaction solution was transferred to a separating lot, and the lower layer was separated. The remaining supernatant was washed twice with 200 ml of water and once with 50 ml of saturated aqueous sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The resulting solids were separated by filtration, and the resulting solution was transferred to a branch flask and concentrated under reduced pressure by a rotary evaporator to give 115.2 g of a colorless transparent liquid. As a result of analyzing the reaction product by 29 Si-nuclear magnetic resonance analysis, a molecule having an average of 8.6 silicon atom-bonded hydrogen atoms and an average of 3.4 silicon atom-bonded methoxy groups in one molecule represented by the following average molecular formula: It has been found to be a terrestrial siloxane-silalkylene copolymer. In addition, these branched siloxane-silalkylene copolymers were found to have a polystyrene reduced number average molecular weight of 1,980 by gel permeation chromatography.
    Example 2
    Into a 200 ml four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping lot, 51.8 g of vinyltrimethoxysilane and 0.04 g of a 3% isopropanol solution of chloroplatinic acid were added and heated to 100 ° C while stirring. . Subsequently, 44.1 g of the branched siloxane-silalkylene copolymer obtained in Example 1 was slowly added dropwise so that the reaction temperature was maintained at 100 to 110 ° C using a dropping lot. After completion of the dropwise addition, the reaction solution was heated at 120 ° C. for 1 hour. After cooling, the reaction solution was transferred to a branched flask and concentrated under reduced pressure by a rotary evaporator to give 186.2 g of a slightly brown liquid. The reaction product was analyzed by 29 Si-nuclear magnetic resonance analysis and found to be a branched siloxane-silalkylene copolymer having an average of 29 silicon atom-bonded methoxy groups in one molecule represented by the following average molecular formula. It became. In addition, this branched siloxane-silalkylene copolymer was found to have a polystyrene reduced number average molecular weight of 2,900 by gel permeation chromatography.
    Example 3
    Into a 1 L four-necked flask equipped with a stirring device, a thermometer, a reflux condenser, and a dropping lot, 134.3 g of 1,1,3,3-tetramethyldisiloxane, 100 ml of concentrated hydrochloric acid, 200 ml of water, and 200 ml of isopropanol were added. And stirred. Subsequently, 73.3 g of the branched siloxane-silalkylene copolymer obtained in Example 2 was slowly added dropwise over 1 hour using the dropping lot. After completion of the dropwise addition, the reaction solution was stirred at room temperature for 1 hour. Subsequently, the reaction solution was transferred to a separating lot, and the lower layer was separated. The remaining supernatant was washed twice with 200 ml of water and once with 50 ml of saturated aqueous sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The resulting solid was separated by filtration, and the resulting solution was transferred to a branch flask and concentrated under reduced pressure by a rotary evaporator to give 102.2 g of a colorless transparent liquid. As a result of analyzing the reaction product by 29 Si-nuclear magnetic resonance analysis, a molecule having an average of 17.9 silicon atom-bonded hydrogen atoms and an average of 11.1 silicon atom-bonded methoxy groups in one molecule, represented by the following average molecular formula: It has been found to be a terrestrial siloxane-silalkylene copolymer. In addition, this branched siloxane-silalkylene copolymer was found to have a polystyrene reduced number average molecular weight of 4,350 by gel permeation chromatography.
    Example 4
    Into a 200 ml four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping lot, 51.8 g of vinyltrimethoxysilane and 0.04 g of a 3% isopropanol solution of chloroplatinic acid were added and heated to 100 ° C while stirring. . Subsequently, 44.1 g of the branched siloxane-silalkylene copolymer obtained in Example 3 was slowly added dropwise so that the reaction temperature was maintained at 100 to 110 ° C using a dropping lot. After completion of the dropping, the reaction solution was heated at 120 ° C. for 1 hour. After cooling, the reaction solution was transferred to a branched flask and concentrated under reduced pressure by a rotary evaporator to give 186.2 g of a slightly brown liquid. The reaction product was analyzed by 29 Si-nuclear magnetic resonance analysis and found to be a branched siloxane-silalkylene copolymer having an average of 65 silicon atom bonded methoxy groups in one molecule, represented by the following average molecular formula. It became. In addition, this branched siloxane-silalkylene copolymer was found to have a polystyrene reduced number average molecular weight of 4,430 by gel permeation chromatography.
    Example 5
    Into a 200 ml four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping lot, 97.8 g of vinyltrimethoxysilane and 0.04 g of a 3% isopropanol solution of chloroplatinic acid were added thereto, and the mixture was heated to 100 ° C while stirring. . Subsequently, 53.7 g of methyltris (dimethylsiloxy) silane was slowly added dropwise thereto so that the reaction temperature was maintained at 100 to 110 ° C using a dropping lot. After completion of the dropwise addition, the reaction solution was heated at 120 ° C for 1 hour. After cooling, the reaction solution was transferred to a branch flask and concentrated under reduced pressure by a rotary evaporator to give 142.5 g of a slightly brown liquid. Subsequently, in a 1 L four-necked flask equipped with a stirrer, thermometer, reflux condenser, and dropping lot, 120.9 g of 1,1,3,3-tetramethyldisiloxane, 100 ml of concentrated hydrochloric acid, 200 ml of water and isopropanol 200 ml was added and stirred. Then, 71.3 g of the branched siloxane-silalkylene copolymer obtained above was slowly added dropwise over 1 hour using the dropping lot. After completion of the dropwise addition, the reaction solution was stirred at room temperature for 1 hour. Subsequently, the reaction solution was transferred to a separating lot, and the lower layer was separated. The remaining supernatant was washed twice with 200 ml of water and once with 50 ml of saturated aqueous sodium bicarbonate solution, and dried over anhydrous magnesium sulfate. The resulting solid was separated by filtration, and the resulting solution was transferred to a branch flask and concentrated under reduced pressure by a rotary evaporator to give 98.3 g of a colorless transparent liquid. As a result of analyzing the reaction product by 29 Si-nuclear magnetic resonance analysis, a molecule having an average of 6.5 silicon atom-bonded hydrogen atoms and an average of 2.5 silicon atom-bonded methoxy groups in one molecule represented by the following molecular formula: It has been found to be a terrestrial siloxane-silalkylene copolymer. In addition, this branched siloxane-silalkylene copolymer was confirmed by gel permeation chromatography to have a polystyrene reduced number average molecular weight of 1,446.
    The branched siloxane-silalkylene copolymer of the present invention is characterized by a novel polymer having a plurality of silicon atom-bonded hydrogen atoms or silicon atom-bonded alkoxy groups in one molecule.
    权利要求:
    Claims (4)
    [1" claim-type="Currently amended] Branched siloxane-silalkylene copolymer represented by the following formula (1):
    Formula 1

    Where
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    a is 3 or 4,
    X 1 is a silylalkyl group represented by the following formula (2) when i is 1.
    Formula 2

    (Wherein
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    R 2 is an alkylene group having 2 to 10 carbon atoms,
    R 3 is an alkyl group having 1 to 10 carbon atoms,
    X i + 1 is a hydrogen atom or the silylalkyl group,
    i is an integer of 1 to 10 representing the hierarchical increase in the silylalkyl group,
    b i is an integer of 0 to 3)
    [2" claim-type="Currently amended] The method of claim 1,
    Branched siloxane-silalkylene copolymer represented by the following formula (3):
    Formula 3

    Where
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    R 2 is an alkylene group having 2 to 10 carbon atoms,
    R 3 is an alkyl group having 1 to 10 carbon atoms,
    a is 3 or 4,
    b 1 is an integer of 0-3.
    [3" claim-type="Currently amended] The method of claim 1,
    Branched siloxane-silalkylene copolymer represented by the following formula (4):
    Formula 4

    Where
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    R 2 is an alkylene group having 2 to 10 carbon atoms,
    R 3 is an alkyl group having 1 to 10 carbon atoms,
    a is 3 or 4,
    b 1 and b 2 are integers of 0 to 3, but the sum of b 1 in one molecule is less than (3 × a).
    [4" claim-type="Currently amended] The method of claim 1,
    Branched siloxane-silalkylene copolymer represented by the following formula (5):
    Formula 5

    Where
    R 1 is an alkyl or aryl group having 1 to 10 carbon atoms,
    R 2 is an alkylene group having 2 to 10 carbon atoms,
    R 3 is an alkyl group having 1 to 10 carbon atoms,
    a is 3 or 4,
    b 1 , b 2 and b 3 are integers from 0 to 3, but the sum of b 1 in one molecule is less than (3 × a), and the sum of b 2 in one molecule is {3 × a × (3-b 1). )} Is less than.
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    同族专利:
    公开号 | 公开日
    DE69823974T2|2005-05-25|
    KR100507886B1|2006-01-27|
    DE69823974D1|2004-06-24|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    1998-02-25|Priority to JP06065698A
    1998-02-25|Priority to JP98-60656
    1998-08-26|Application filed by 이이즈까 고지, 도레이 다우 코닝 실리콘 가부시끼가이샤
    1999-09-27|Publication of KR19990071381A
    2006-01-27|Application granted
    2006-01-27|Publication of KR100507886B1
    优先权:
    申请号 | 申请日 | 专利标题
    JP06065698A|JP3797519B2|1997-02-28|1998-02-25|Branched siloxane / silalkylene copolymer|
    JP98-60656|1998-02-25|
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