JPS638389A - Production of silicon compound - Google Patents
Production of silicon compoundInfo
- Publication number
- JPS638389A JPS638389A JP15094886A JP15094886A JPS638389A JP S638389 A JPS638389 A JP S638389A JP 15094886 A JP15094886 A JP 15094886A JP 15094886 A JP15094886 A JP 15094886A JP S638389 A JPS638389 A JP S638389A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- siliconate
- silicon compound
- group
- amino acid
- 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.)
- Pending
Links
- 150000003377 silicon compounds Chemical class 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000005625 siliconate group Chemical group 0.000 claims abstract description 20
- 150000001413 amino acids Chemical class 0.000 claims abstract description 11
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- 125000005372 silanol group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 abstract description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 7
- 239000003513 alkali Substances 0.000 abstract description 6
- 239000003456 ion exchange resin Substances 0.000 abstract description 6
- 229920003303 ion-exchange polymer Polymers 0.000 abstract description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 abstract description 5
- 235000013922 glutamic acid Nutrition 0.000 abstract description 5
- 239000004220 glutamic acid Substances 0.000 abstract description 5
- 239000002537 cosmetic Substances 0.000 abstract description 3
- 239000004310 lactic acid Substances 0.000 abstract description 3
- 235000014655 lactic acid Nutrition 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001261 hydroxy acids Chemical class 0.000 abstract 2
- 229940061720 alpha hydroxy acid Drugs 0.000 abstract 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- SHEYKHMHFCPWCL-UHFFFAOYSA-N disilanyl-hydroxy-methylsilane Chemical compound C[SiH](O)[SiH2][SiH3] SHEYKHMHFCPWCL-UHFFFAOYSA-N 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 4
- -1 dodecyltrisilanol Chemical compound 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 3
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013402 health food Nutrition 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical compound OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VSTDKEWSKBIOMX-UHFFFAOYSA-N CC[SiH](O)[SiH2][SiH3] Chemical compound CC[SiH](O)[SiH2][SiH3] VSTDKEWSKBIOMX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-VANFPWTGSA-N D-mannopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-VANFPWTGSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KTHDTJVBEPMMGL-VKHMYHEASA-N N-acetyl-L-alanine Chemical compound OC(=O)[C@H](C)NC(C)=O KTHDTJVBEPMMGL-VKHMYHEASA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- VVOOXZLSKZCCJW-UHFFFAOYSA-N benzyl-(disilanyl)-hydroxysilane Chemical compound O[SiH](Cc1ccccc1)[SiH2][SiH3] VVOOXZLSKZCCJW-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- PMWBHKAFJHMDJA-UHFFFAOYSA-N cyclohexyl-(disilanyl)-hydroxysilane Chemical compound C1(CCCCC1)[SiH]([SiH2][SiH3])O PMWBHKAFJHMDJA-UHFFFAOYSA-N 0.000 description 1
- CPKTUMHHHOVSQC-UHFFFAOYSA-N diethyl-hydroxy-silylsilane Chemical compound CC[Si](O)([SiH3])CC CPKTUMHHHOVSQC-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- ZOAYMOGNAWSEJE-UHFFFAOYSA-N disilanyl-hydroxy-(2-phenylethyl)silane Chemical compound [SiH3][SiH2][SiH](O)CCC1=CC=CC=C1 ZOAYMOGNAWSEJE-UHFFFAOYSA-N 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WXKKFJKVDIJRDT-UHFFFAOYSA-N hydroxy-dimethyl-silylsilane Chemical compound C[Si](C)(O)[SiH3] WXKKFJKVDIJRDT-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、薬品、化粧品、健康食品等に、配合するケイ
素化合物を効率的に合成するとともに水溶夜中での安定
性を向上させたケイ素化合物の製造方法に関するもので
ある。[Detailed Description of the Invention] [Field of Industrial Application] The present invention is directed to the efficient synthesis of silicon compounds to be incorporated into medicines, cosmetics, health foods, etc., as well as improved stability of the silicon compounds during the night when dissolved in water. The present invention relates to a manufacturing method.
ケイ素化合物には最近種々の生理活性が見い出されてお
り、医薬品あるいは化粧品、健康食品等への導入検討も
なされるようになってきたが、安定性が悪いので、種々
の安定剤の添加により安定性の向上検討がなされている
。例えば、特公昭４６−２１６９５号公報には、アルカ
リシリコネートの水溶液に、サリチル酸、マンヌロン酸
、クエン酸又はフェノール等を添加して、錯化させ、次
いで攪拌を継続しながら陽イオン交換ｉｔ脂を添加して
、ｐＨ１〜８の安定な水溶液を得る方法が開示されてい
る。又、特公昭５３−１８１１号公報には、アルコール
又はフェノール性化合物を含有する水溶液に、有機ケイ
素化合物のアルカリ性水溶液を加えた後、溶液のｐｔｌ
を陽イオン交換樹脂により１３以下とすることによって
安定な水溶液を得る方法が開示されている。しかしなが
ら、これらの方法では、イオン交換樹脂を用いているの
で濾過が必要となり、煩雑かつコストアップになるとい
う問題がある。Silicon compounds have recently been found to have various physiological activities, and their introduction into pharmaceuticals, cosmetics, health foods, etc. is being considered, but their stability is poor, so it is difficult to stabilize them by adding various stabilizers. Improvements in performance are being considered. For example, in Japanese Patent Publication No. 46-21695, salicylic acid, mannuronic acid, citric acid, phenol, etc. are added to an aqueous solution of an alkali siliconate to form a complex, and then a cation-exchanged it fat is added while stirring. A method for obtaining a stable aqueous solution with a pH of 1 to 8 is disclosed. In addition, Japanese Patent Publication No. 1811/1983 discloses that after adding an alkaline aqueous solution of an organosilicon compound to an aqueous solution containing an alcohol or a phenolic compound, the ptl of the solution is
A method is disclosed in which a stable aqueous solution is obtained by reducing the value of 13 to 13 or less using a cation exchange resin. However, since these methods use an ion exchange resin, filtration is required, which is complicated and increases costs.
本発明は、イオン交換樹脂を用いることなく、簡単に操
作でき、安価に製造でき、かつ安定性の良好なケイ素化
合物の水溶液を辱ることを目的とする。The object of the present invention is to provide an aqueous solution of a silicon compound which can be easily operated, manufactured at low cost, and has good stability without using an ion exchange resin.
本発明は、シリコネートをオキシ酸又はアミノ酸で中和
すると、分子内にシラノール基を少くとも１個有するケ
イ素化合物を効率よく、かつ安定に製造できるとの知見
に基づいてなされたのである。The present invention was made based on the knowledge that by neutralizing siliconate with an oxyacid or an amino acid, a silicon compound having at least one silanol group in the molecule can be efficiently and stably produced.
本発明の製造方法により製造される目的物としては、下
記一般式（１）で表わされるケイ素化合物があげられる
。The target product produced by the production method of the present invention includes a silicon compound represented by the following general formula (1).
Ｒｎ５ｉ （ＯＨ）、−１・ ・ ・ （ｒ ）（式
中、Ｒは、炭素数１〜１２、好ましくは１〜６のアルキ
ル基、アラルキル基、アルケニル基、シクロアルキル基
、またはアルコキシ基であり、２以上のＲは互いに同一
でも異なっても良く、ｎは０〜３、好ましくは１〜３の
整数である。）
で表わされる化合物又はこれらの脱水縮合体である。こ
れらのケイ素化合物として、具体的には、メチルトリシ
ラノール、ジメチルジシラノール、トリメチルシラノー
ル、エチルトリシラノール、ジエチルジシラノール、プ
ロビルトリシラノール、オクチルトリシラノール、ドデ
シルトリシラノール、ベンジルトリシラノール、フェニ
ルエチルトリシラノール、プロペニルトリシラノール、
シクロへキシルトリシラノール、メトキシトリシラノー
ル、エトキントリシラノールの１種又は２種以上の混合
物があげられる。又、上記シラノール頌の脱水縮合２量
体、同３量体なども含まれる。上記各種化合物のうち、
本発明では、特にメチルトリシラノールが好ましい。Rn5i (OH), -1. . , two or more R's may be the same or different, and n is an integer of 0 to 3, preferably 1 to 3.) or a dehydrated condensate thereof. Specifically, these silicon compounds include methyltrisilanol, dimethyldisilanol, trimethylsilanol, ethyltrisilanol, diethyldisilanol, probyltrisilanol, octyltrisilanol, dodecyltrisilanol, benzyltrisilanol, and phenylethyltrisilanol. silanol, propenyltrisilanol,
Examples include one or a mixture of two or more of cyclohexyltrisilanol, methoxytrisilanol, and etquintrisilanol. Also included are dehydrated condensed dimers and trimers of the above-mentioned silanol. Among the above various compounds,
In the present invention, methyltrisilanol is particularly preferred.
本発明では、上記ケイ素化合物を製造するにあたり、原
材として、対応するシリコネートを用いる。ここで、シ
リコネートとしては、下記一般式（ＩＩ）で表わされる
ものを用いるのがよい。In the present invention, a corresponding siliconate is used as a raw material in producing the silicon compound. Here, as the siliconate, it is preferable to use one represented by the following general formula (II).
ＲｎＳｉ （ＯＨ）１（ＯＭ）、２ ・・・（Ｉ
ｆ）（式中、Ｍはアルカリ金属、１Ｔｌｌ十ｍ２は４−
ｎ、ｍ。RnSi (OH)1(OM),2...(I
f) (In the formula, M is an alkali metal, 1 Tll m2 is 4-
n, m.
は０〜３、ｍ２は１〜４であり、他は上記と同じ意味で
ある。）
式中、Ｍとしては、リチウム、ナトリウム、カリウムが
あげられ、具体的には、上記（ｊ ＞の化合物について
例示した化合物の一〇ＨのＨをアルカリ金属に変えたも
のがあげられる。is 0 to 3, m2 is 1 to 4, and the others have the same meanings as above. ) In the formula, examples of M include lithium, sodium, and potassium, and specifically examples include those in which H in 10H of the compound exemplified above for the compound (j>) is replaced with an alkali metal.
上記一般式（Ｉ）で表わされるシリコネートは、対応す
るハロゲン化物、例えば、一般式（ＩＩ［）で表わされ
る化合物をアルカリで加水分解することによって容易に
製造される。The siliconate represented by the general formula (I) above is easily produced by hydrolyzing a corresponding halide, for example, a compound represented by the general formula (II[), with an alkali.
Ｒｎ５ＩＸ４−、、・・・（■）
（式中、Ｘは塩素、臭素、フッ素などのハロゲンを示し
他は上記と同じ意味である。）
本発明では、上記シリコネートを特定の酸により中和し
、ケイ素化合物中の一〇Ｍ基を一〇Ｈ基にすることを特
徴とする。Rn5IX4-,...(■) (In the formula, X represents a halogen such as chlorine, bromine, or fluorine, and the others have the same meanings as above.) In the present invention, the siliconate is neutralized with a specific acid. , is characterized in that the 10M group in the silicon compound is replaced with 10H group.
ここで、中和に用いるアミノ酸としては通常のアミノ酸
でもよいが、特に酸性アミノ酸及びアシルアミノ酸が好
ましい。具体的には、アスパラギン酸、グルタミン酸等
の炭素数４〜５の酸性アミノ酸、Ｎ−アセチルグリシン
、Ｎ−アセチルアラニン等の炭素数４〜１３のアシルア
ミノ酸があげられる。又、ピロリドンカルボン酸のよう
な分子内アミドアミノ酸も使用できる。一方、オキシ酸
としては、通常のオキシ酸ならいずれでもよいが、特に
α−オキシ酸及び芳香族オキシ酸が好ましい。Here, the amino acids used for neutralization may be ordinary amino acids, but acidic amino acids and acylamino acids are particularly preferred. Specifically, acidic amino acids having 4 to 5 carbon atoms such as aspartic acid and glutamic acid, and acyl amino acids having 4 to 13 carbon atoms such as N-acetylglycine and N-acetylalanine are mentioned. Also, intramolecular amide amino acids such as pyrrolidone carboxylic acid can be used. On the other hand, as the oxyacid, any ordinary oxyacid may be used, but α-oxyacid and aromatic oxyacid are particularly preferred.
具体的には、グリコール酸、乳酸、グリセリン酸、タル
トロン酸、リンゴ酸、酒石酸、クエン酸等の炭素数２〜
６のα−オキシ酸、サリチル酸、マンデル酸等の炭素数
７〜９の芳香族オキシ酸が好ましい。使用する量として
は、対応するシリコネートのアルカリ分に対して、１．
０〜２．０当量の酸を用いるのが良く、また、安定化の
為に、それ以上の酸を中和して加えることも可能である
。又微量の鉱酸、アルカリで、ｐＨを例えば４〜７に最
終的に微妙に調製することもできる。中和後のケイ素化
合物濃度は０．１〜５％とするのが好ましい。尚、上記
中和は、０〜７０℃で行なうのがよい。Specifically, those having 2 or more carbon atoms such as glycolic acid, lactic acid, glyceric acid, tartronic acid, malic acid, tartaric acid, citric acid, etc.
Aromatic oxyacids having 7 to 9 carbon atoms, such as α-oxyacids having 6 α-oxyacids, salicylic acid, and mandelic acid, are preferred. The amount used is 1. based on the alkaline content of the corresponding siliconate.
It is preferable to use 0 to 2.0 equivalents of acid, and for stabilization, it is also possible to neutralize and add more acid. Furthermore, the final pH can be finely adjusted to, for example, 4 to 7 using a trace amount of mineral acid or alkali. The silicon compound concentration after neutralization is preferably 0.1 to 5%. Incidentally, the above neutralization is preferably carried out at a temperature of 0 to 70°C.
本発明の方法によれば、高価なイオン交換樹脂を使用す
ることなく、又濾過工程も省略できるので、コスト及び
作業性の面で有利にケイ素化合物を製造することができ
る。According to the method of the present invention, a silicon compound can be produced advantageously in terms of cost and workability, since an expensive ion exchange resin is not used and a filtration step can also be omitted.
又、製造したケイ素化合物を同時に安定化できるので、
本発明の製造方法は非常に効率が良い方法である。In addition, since the silicon compound produced can be stabilized at the same time,
The manufacturing method of the present invention is a very efficient method.
次に実施例により本発明を説明するが、本発明はこれら
に限定されるものではない。Next, the present invention will be explained with reference to Examples, but the present invention is not limited thereto.
実施例１
メチルトリクロルシランを加水分解して生じた沈殿を回
収し、これに等モルの水酸化す） ＩＪウムを加えて溶
解させ、１０％濃度のシリコネート（Ｃ）（３Ｓｌ（○
Ｈ）２ （ＯＮａ ） 〕の水溶液を得た。Example 1 Collect the precipitate generated by hydrolyzing methyltrichlorosilane, add and dissolve equimolar amount of hydroxide, and dissolve siliconate (C) (3Sl(○)) at a concentration of 10%.
An aqueous solution of H)2(ONa)] was obtained.
一方、適当な濃度のグルタミン酸水溶液を作り、後で加
えるシリコネートのアルカリに対して１．１倍当量のグ
ルタミン酸水溶液を採取し、これにシリコネート水溶液
を加えて、中和し、最終的にグルタミン酸Ｎａを含んだ
メチルトリシラノール１％水溶液を調製した。ｐＨは約
５でありこの水溶液は４５℃で１ケ月間透明であり安定
であった。On the other hand, prepare a glutamic acid aqueous solution with an appropriate concentration, collect the glutamic acid aqueous solution in an amount equivalent to 1.1 times the alkali of the siliconate that will be added later, add the siliconate aqueous solution to this, neutralize it, and finally remove the sodium glutamate. A 1% aqueous solution containing methyltrisilanol was prepared. The pH was approximately 5, and the aqueous solution remained transparent and stable for one month at 45°C.
実施例２
実施例１と同様の方法で、シリコネートをＲ製し、１．
０５倍当量の乳酸で中和し、乳酸Ｎａを含むメチル）
ＩＪシラノール１％水溶液を調製した。ｐＨは約４６５
であった。この溶液は４５℃で１ケ月間安定であった。Example 2 In the same manner as in Example 1, siliconate was made into R, and 1.
(Methyl containing sodium lactate, neutralized with 0.5 times equivalent of lactic acid)
A 1% aqueous solution of IJ silanol was prepared. pH is about 465
Met. This solution was stable for one month at 45°C.
実施例３
実施例１と同様の方法でシリコネートを調製し、１．１
倍当量のピロリドンカルボン酸で中和し、ピロリドンカ
ルボン酸ｊｌｌａを含むメチルトリシラノール１％溶液
を調製した。ｐＨは約６であった。この溶液は４５℃で
１ケ月間安定であった。Example 3 Siliconate was prepared in the same manner as in Example 1 and 1.1
The mixture was neutralized with twice the equivalent amount of pyrrolidone carboxylic acid to prepare a 1% methyltrisilanol solution containing pyrrolidone carboxylic acid Jlla. The pH was approximately 6. This solution was stable for one month at 45°C.
実施例４
実施例１と同様の方法でシリコネートを調製し、１．０
５倍当量のサリチル酸で中和し、１％のメチル） ＩＪ
シラノールを含むサリチル酸水溶液を１等だ。Example 4 A siliconate was prepared in the same manner as in Example 1, with a concentration of 1.0
Neutralized with 5 equivalents of salicylic acid, 1% methyl) IJ
An aqueous solution of salicylic acid containing silanol is 1st grade.
ｐＨは約５．０であった。この溶液は４５℃で１ケ月間
安定であった。The pH was approximately 5.0. This solution was stable for one month at 45°C.
実施例５
実施例１と同様の方法でシリコネートを調製し、１．５
倍当量のクエン酸を加えて中和し、１％のメチルトリシ
ラノールを含むクエン酸水溶液を１尋た。Example 5 A siliconate was prepared in the same manner as in Example 1, and 1.5
Double equivalent amount of citric acid was added to neutralize it, and 1 fathom of citric acid aqueous solution containing 1% methyltrisilanol was added.
ｐＨは約４．５であった。この溶液は４５℃で１ケ月間
安定であった。The pH was approximately 4.5. This solution was stable for one month at 45°C.
比較例１
実施例１の方法において、グルタミン酸を用いずにイオ
ン交換樹脂を用いて中和しＩＩ）Ｈ＝ ４．５のメチル
トリシラノール水溶液を得た。又、イオン交換樹脂で中
和後、微量の鉱酸及びアルカリで、ｐＨ＝３．４．５．
６．７の各メチルトリシラノール１％水溶液を得た。こ
れらの溶液を４５℃で保存した所、全て一日で安定性を
失い、白濁した。Comparative Example 1 In the method of Example 1, neutralization was performed using an ion exchange resin without using glutamic acid to obtain II) an aqueous methyltrisilanol solution with H=4.5. After neutralization with an ion exchange resin, the pH was adjusted to 3.4.5 with trace amounts of mineral acid and alkali.
A 1% aqueous solution of each methyltrisilanol in No. 6.7 was obtained. When these solutions were stored at 45°C, they all lost stability within one day and became cloudy.
Claims (5)
素化合物を製造するにあたり、対応するシリコネートを
オキシ酸又はアミノ酸で中和することを特徴とするケイ
素化合物の製造方法。(1) A method for producing a silicon compound, which comprises neutralizing a corresponding siliconate with an oxyacid or an amino acid in producing a silicon compound having at least one silanol group in the molecule.
、Ｒは、炭素数１〜１２のアルキル基、アラルキル基、
アルケニル基、シクロアルキル基、またはアルコキシ基
であり、２以上のＲは互いに同一でも異なっても良く、
ｎは０〜３の整数である。） で表わされる化合物又はこれらの脱水縮合体である特許
請求の範囲第（１）項記載の製造方法。(2) The silicon compound has the general formula (I): R_nSi(OH)_4_-_n...(I) (wherein R is an alkyl group having 1 to 12 carbon atoms, an aralkyl group,
an alkenyl group, a cycloalkyl group, or an alkoxy group, and two or more R's may be the same or different from each other,
n is an integer from 0 to 3. ) or a dehydrated condensate thereof.
II）（式中、Ｒは、炭素数１〜１２のアルキル基、アラ
ル基、アルケニル基、シクロアルキル基、またはアルコ
キシ基であり、２以上のＲは互いに同一でも異なってい
ても良く、Ｍはアルカリ金属である。又、ｎは０〜３、
ｍ＿１＋ｍ＿２は４−ｎ、ｍ＿１は０〜３、ｍ＿２は１
〜４である。）で表わされる化合物てある特許請求の範
囲第（１）項記載の製造方法。(3) The siliconate has the general formula (II): R_nSi(OH)_m_1(OM)_m_2...(
II) (wherein, R is an alkyl group, an aral group, an alkenyl group, a cycloalkyl group, or an alkoxy group having 1 to 12 carbon atoms, two or more R's may be the same or different from each other, and M is It is an alkali metal. Also, n is 0 to 3,
m_1+m_2 is 4-n, m_1 is 0 to 3, m_2 is 1
~4. ) The manufacturing method according to claim (1), which comprises a compound represented by:
ある特許請求の範囲第（１）項記載の製造方法。(4) The production method according to claim (1), wherein the amino acid is an acidic amino acid or an acylamino acid.
る特許請求の範囲第（１）項記載の製造方法。(5) The manufacturing method according to claim (1), wherein the oxyacid is an α-oxyacid or an aromatic oxyacid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15094886A JPS638389A (en) | 1986-06-27 | 1986-06-27 | Production of silicon compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15094886A JPS638389A (en) | 1986-06-27 | 1986-06-27 | Production of silicon compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS638389A true JPS638389A (en) | 1988-01-14 |
Family
ID=15507916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15094886A Pending JPS638389A (en) | 1986-06-27 | 1986-06-27 | Production of silicon compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS638389A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2645863A1 (en) * | 1989-04-12 | 1990-10-19 | Voisin Philippe | Silicon compounds and process for the manufacture thereof |
| EP0531134A2 (en) * | 1991-09-06 | 1993-03-10 | General Electric Company | Aqueous water repellent compositions |
| US5486598A (en) * | 1994-05-20 | 1996-01-23 | University Of Florida | Silica mediated synthesis of peptides |
| CN101906111A (en) * | 2010-08-12 | 2010-12-08 | 胡竹林 | Method for preparing methyl silicic acid and industrial hydrochloric acid by using hydrolysis of methyl trichlorosilane |
-
1986
- 1986-06-27 JP JP15094886A patent/JPS638389A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2645863A1 (en) * | 1989-04-12 | 1990-10-19 | Voisin Philippe | Silicon compounds and process for the manufacture thereof |
| EP0531134A2 (en) * | 1991-09-06 | 1993-03-10 | General Electric Company | Aqueous water repellent compositions |
| US5486598A (en) * | 1994-05-20 | 1996-01-23 | University Of Florida | Silica mediated synthesis of peptides |
| CN101906111A (en) * | 2010-08-12 | 2010-12-08 | 胡竹林 | Method for preparing methyl silicic acid and industrial hydrochloric acid by using hydrolysis of methyl trichlorosilane |
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