JPS62225533A - Organopolysiloxane modified with alkoxysilylalkyl polyoxyalkylene - Google Patents
Organopolysiloxane modified with alkoxysilylalkyl polyoxyalkyleneInfo
- Publication number
- JPS62225533A JPS62225533A JP6805586A JP6805586A JPS62225533A JP S62225533 A JPS62225533 A JP S62225533A JP 6805586 A JP6805586 A JP 6805586A JP 6805586 A JP6805586 A JP 6805586A JP S62225533 A JPS62225533 A JP S62225533A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- polyoxyalkylene
- integer
- represented
- 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
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000962 organic group Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 abstract description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 12
- 125000004122 cyclic group Chemical group 0.000 abstract description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 6
- 229910052697 platinum Inorganic materials 0.000 abstract description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 abstract description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 abstract description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract description 4
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- -1 polysiloxanes Polymers 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000005452 bending Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- 238000010183 spectrum analysis Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野１
本発明は、新規なアルコキシシリルアルキル・ポリオキ
シアルキレン変性オルがノボリシロキサンに関する。さ
らに詳しくは、分子鎖末端がフルコキシシリルアルキル
基もしくはポリオキシアルキレン基であって、１分子中
にフルコキシシリ序アルキル基およびポリオキシアルキ
レン基の両方を有する新規なオルガノポリシロキサンに
関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application 1] The present invention relates to a novel alkoxysilylalkyl polyoxyalkylene-modified novolisiloxane. More specifically, the present invention relates to a novel organopolysiloxane having a flukoxysilylalkyl group or a polyoxyalkylene group at the molecular chain end and having both a flukoxysilylalkyl group and a polyoxyalkylene group in one molecule.
［従来の技術１
オルガノポリシロキサンは、その基本構造の構成、大き
さ、形状、側鎖の種類およびその分子量等により油状、
ゴム状、固形樹脂状と極めて広範囲の性状を有しており
、またその特徴ある耐熱、耐寒性、酸化安定性、耐候性
、離型性、撥水性等と相まって繊維、離型紙、電気・電
子、走築、塗料添加剤等各種多様な工業分野で使用され
ており、分子内にアルコキシ基を有するオルガノポリシ
ロキサンまたは分子内にポリオキシアルキレン基を有す
るオルガノポリシロキサンはよく知られている。また、
分子側鎖中にフルコキシシリルアルキル基およびポリオ
キシフルキレン基の両方を有するオルが７ポリシロキサ
ンも知られている（特開昭５７−１３９１２３号公報参
照）。[Prior art 1 Organopolysiloxanes are oily,
It has an extremely wide range of properties such as rubber-like and solid resin-like, and its characteristic heat resistance, cold resistance, oxidation stability, weather resistance, mold release property, water repellency, etc., makes it suitable for fibers, release paper, electrical and electronics. Organopolysiloxanes having an alkoxy group in the molecule or organopolysiloxanes having a polyoxyalkylene group in the molecule are well known. Also,
Or-7 polysiloxanes having both flukoxysilylalkyl groups and polyoxyfulkylene groups in their molecular side chains are also known (see JP-A-57-139123).
［発明が解決しようとする問題点１
しかしながら、分子鎖末端がフルコキシシリルアルキル
基らしくはポリオキシアルキレン基であって、１分子中
にフルフキシシリルアルキル基およびポリオキシアルキ
レン基の両方を有するオルガノポリシロキサンは未だに
知られていない。[Problem to be Solved by the Invention 1] However, the molecular chain terminal is a flukoxysilylalkyl group, which is likely a polyoxyalkylene group, and organoorganisms having both a flukoxysilylalkyl group and a polyoxyalkylene group in one molecule Polysiloxane is still unknown.
本発明は、分子鎖末端がフルコキシシリルアルキル基も
しくはポリオキシアルキレン基であって、１分子中にフ
ルコキシシリルアルキル基およびポリオキシアルキレン
基の両方を有するオルガノポリシロキサンを提供するこ
とを目的とする。An object of the present invention is to provide an organopolysiloxane having a flukoxysilylalkyl group or a polyoxyalkylene group at the molecular chain end and having both a flukoxysilylalkyl group and a polyoxyalkylene group in one molecule. do.
［問題点を解決するための手段および作用の説明１
上記した目的は、一般式
［式中、Ｒは炭素原子数１〜１ｏの一価炭化水素基、八
および八゛は共にＱもしくは共にＧであり、Ｑは式
％式％
で示される基、Ｘは炭素原子数１〜４のアルコキシ基、
Ｒ１は炭素原子数２〜５のアルキレン基、ａは２よたは
３、Ｇは式
％式％）
で示される基、Ｒ２は水素原子もしくは炭素原子数１〜
５の一価有機基、ｂおよびＣは０〜１（）。[Explanation 1 of Means and Effects for Solving Problems] The above object is achieved by the general formula [wherein R is a monovalent hydrocarbon group having 1 to 1 carbon atoms, and 8 and 8 are both Q or both G , Q is a group represented by the formula %, X is an alkoxy group having 1 to 4 carbon atoms,
R1 is an alkylene group having 2 to 5 carbon atoms, a is 2 or 3, G is a group represented by the formula %), and R2 is a hydrogen atom or a group having 1 to 5 carbon atoms.
5 monovalent organic group, b and C are 0-1 ().
の整数、ただしｂ＋ｃは２〜２００の整数である。, where b+c is an integer from 2 to 200.
１は１〜５００の整数、ｍはＯ〜１００の整数、ｎはＯ
〜１００の整数、ただしＡおよび八゛が共にｑである場
合、ｎは１〜１００の整数であり、八および八゛が共に
Ｇである場合、ｍは１〜１００の整数である。１で表わ
されるアルフキシシリルアルキル・ポリオキシアルキレ
ン変性オルガノポリシロキサンにより達成される。1 is an integer from 1 to 500, m is an integer from 0 to 100, n is O
an integer from 1 to 100, provided that when A and 8' are both q, n is an integer from 1 to 100, and when 8 and 8' are both G, m is an integer from 1 to 100. This is achieved using the alphoxysilylalkyl polyoxyalkylene modified organopolysiloxane represented by 1.
これを説明するに、前記した式中Ｒは炭素原子数１〜１
０の一価炭化水素基であり、これにはメチル基、エチル
基、プロピル基、オクチル基などのアルキル基、２−フ
ェニルエチル基、２−フェニルプロピル基、３・３＝３
−）リフルオロプロピル基などの置換アルキル基、７エ
二ル基、トリル基などの７リール基、または置換アリー
ル基が例示され、分子中のＲは同種のものであってもよ
く、また異種のものであってちよい。To explain this, R in the above formula has 1 to 1 carbon atoms.
0 monovalent hydrocarbon group, which includes alkyl groups such as methyl group, ethyl group, propyl group, octyl group, 2-phenylethyl group, 2-phenylpropyl group, 3.3=3
-) A substituted alkyl group such as a fluoropropyl group, a 7-aryl group such as a 7-enyl group, a tolyl group, or a substituted aryl group, and the R's in the molecule may be the same or different. It's fine if it's something like that.
八およびへ゛１土共（こＱもしく１土共１こＣであり。8 and 1 earth (this Q or 1 earth and 1 earth C).
Ｑは弐
Ｒ，−ａ
Ｒ’ Ｓｉ −Ｘａ
で示される基であり、本発明のオルガノポリシロキサン
に加水分解性、縮合性、結合性等の反応性を付与する。Q is a group represented by 2R, -aR'Si-Xa, which imparts reactivity such as hydrolyzability, condensability, and bondability to the organopolysiloxane of the present invention.
Ｒ１は炭素原子数２〜５のアルキレン基であり、これに
は−Ｃ１１２Ｃ１［２−１−ＣＩ＋２ＣＨ２ＣＨ２−１
−ＣＨ（Ｃ１１３）Ｃｔ１２−１−（Ｃ）１２Ｌ−１−
（Ｃ）１２）Ｓ−が例示され、分子中のＲ１は同種のも
のであってもよく、また異種のちのであってもよい。×
は炭素原子数１〜４のアルコキシ基であり、これにはメ
トキシ基、エトキシ基、プロポキシ基、メトキシエトキ
シ基などが例示される。ａは２または３である。R1 is an alkylene group having 2 to 5 carbon atoms, including -C112C1[2-1-CI+2CH2CH2-1
-CH(C113)Ct12-1-(C)12L-1-
(C)12)S- is exemplified, and R1 in the molecule may be the same or different. ×
is an alkoxy group having 1 to 4 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, a methoxyethoxy group, and the like. a is 2 or 3.
Ｑの具体例としては −Ｃ１１２ＣＩｔ□−５ｉ（ＯＣＨｄ−１ＣＩ＋。A specific example of Q is -C112CIt□-5i (OCHd-1CI+.
迦
−ｃ１１２ｃ１１２−ｓｉ（ｏｃｌｌａ）２、−（Ｃ１
１２）、−５ｉ（ＯＣＩＩ□ｅｌｌ、Ｌ、Ｃ１１゜
−（Ｃｔｌｚ）−５ｉ（ｏｃｕ２ｃ）１．）２、ＣＩ。迦-c112c112-si(oclla)2,-(C1
12), -5i(OCII□ell, L, C11°-(Ctlz)-5i(ocu2c)1.)2, CI.
亀
−Ｃ１２ＣＬ−Ｓｉ（ＯＣＨ−ｅｌｌ、）２、Ｇは式
％式％
で示される基であり、本発明のオルガノポリシロキサン
に親水性、帯電防止性を付与する。式中Ｒ２は水素原子
もしくは炭素原子数１〜５の一価有磯基であり、−価有
機基としてはメチル基、エチル基、プロピル基のような
アルキル基、アセチル基、プロピオニル基のようなアシ
ル基が例示される。ｂおよびＣは０〜１００の整数であ
り、ただしｂ＋ｃは２〜２００Ｉ７）整数である。Tortoise-C12CL-Si(OCH-ell, )2,G is a group represented by the formula % and imparts hydrophilicity and antistatic properties to the organopolysiloxane of the present invention. In the formula, R2 is a hydrogen atom or a monovalent aisogroup having 1 to 5 carbon atoms, and the -valent organic group includes an alkyl group such as a methyl group, an ethyl group, and a propyl group, an acetyl group, and a propionyl group. An example is an acyl group. b and C are integers from 0 to 100, provided that b+c is an integer from 2 to 200I7).
また１は１〜５００の整数、ｍはＯ〜１００の整数、ｎ
はθ〜１００の整数である。ただし八およびＡ゛が共に
Ｑである場合、ｎは１〜１００であり、主た八お上び八
゛が共１こＣである場合、ｍは１〜１００である。Also, 1 is an integer from 1 to 500, m is an integer from 0 to 100, and n
is an integer between θ and 100. However, when 8 and A' are both Q, n is 1 to 100, and when the main 8, A and A are both 1 and C, m is 1 to 100.
この上うなオルがノボリシロキサンは、文献未記載の新
規化合物であり、具体例としては、上述のオルガノポリ
シロキサンにおいて両末端のけい素原子結合メチル基各
１個をフェニル基または３・３・３− ） ＩＪ フル
オロプロピル基に変えた化合物、あるいはジメチルポリ
シロキサン単位の一部らしくは全部をメチルフェニルシ
ロキサン単位、メチル（ｎ−オクチル）シロキサン単位
に変えたもの、またはメチル（３・３・３− ） ＋７
フルオロプロピル）シロキサン単位に変えたちのがあ
げられる。Una-orga novolisiloxane is a new compound that has not been described in any literature, and a specific example is the above-mentioned organopolysiloxane in which one silicon-bonded methyl group at both ends is replaced with a phenyl group or 3, 3, or 3. -) IJ A compound in which a fluoropropyl group is changed, or a part or all of a dimethylpolysiloxane unit is changed into a methylphenylsiloxane unit, a methyl (n-octyl)siloxane unit, or a methyl (3, 3, 3- ) +7
Fluoropropyl)siloxane units can be used.
本発明のオルガノポリシロキサンは次のようにして合成
される。The organopolysiloxane of the present invention is synthesized as follows.
＾および＾゛が共にＱの場合には、まず一般式％式％
（式中、Ｒ３は炭素数２〜５のフルケニル基であ１）、
Ｒ，Ｘおよびａは前記と同じ）で示されるシランを、一
般式
％式％
（式中、Ｒは前記と同じ）で示されるオルガフハイドロ
ジエンジシロキサンおよび一般式（式中、ｙは３〜１０
の整数、Ｒは前記と同じ）で示される環状オルガノハイ
ドロジエンシロキサン（ｍが０の場合には不要）に、そ
れぞれ塩化白金酸のような白金系触媒の存在下で付加反
応させて一般式
（式中、Ｒ，Ｒ１、Ｘおよびａは前記と同じ）で示され
る化合物および一般式 ′
（式中、Ｒ，Ｒ１、Ｘ、ｙおよびａは前記と同じ）で示
一般式
（式中、Ｒ，ｙは前記と同じ）で示される環状オル（式
中、Ｒ％ ｙは前記と同じ）で示される環状シ′オルガ
ノシロキサンを硫酸、硝酸、トリフルオロメタンスルホ
ン酸、活性白土のような酸性触媒により、重合して、一
般式
％式％
（式中、Ｒ，Ｒ’、Ｘ、ａ、１、ｍおよび１１は前記と
同し）で示されるオルガノハイドロジエンポリシロキサ
ン＋今虎十み−
さらに、該オルガノハイドロジエンポリシロキサンと一
般式
％式％）
（式中、Ｒ２、Ｒ３、ｂおよびＣは前記と同じ）で示さ
れるアルケニル基含有ポリオキシアルキレンを白金系触
媒で付加反応させることにより本発明のオルガノポリシ
ロキサンが合成される。When both ^ and ^゛ are Q, first the general formula % formula % (in the formula, R3 is a fluorenyl group having 2 to 5 carbon atoms and 1),
R, X, and a are the same as above) silane represented by the general formula % formula ~10
, R is the same as above) is subjected to an addition reaction in the presence of a platinum-based catalyst such as chloroplatinic acid, respectively, to form a cyclic organohydrodiene siloxane represented by the general formula ( Compounds represented by the general formula ' (wherein R, R1, X, and a are the same as above) and the general formula (wherein, R A cyclic organosiloxane represented by a cyclic organosiloxane (in the formula, R% y is the same as above) is treated with an acidic catalyst such as sulfuric acid, nitric acid, trifluoromethanesulfonic acid, or activated clay. , polymerized to form an organohydrodiene polysiloxane represented by the general formula % (where R, R', X, a, 1, m and 11 are the same as above) + Imatora Jumi - The present invention is produced by addition-reacting the organohydrodiene polysiloxane with an alkenyl group-containing polyoxyalkylene represented by the general formula % (% formula %) (wherein R2, R3, b and C are the same as above) with a platinum-based catalyst. organopolysiloxane is synthesized.
主た八および八゛が共にＣの場合には、まず一般式
（式中、Ｒ，Ｖは前記と同じ）で示される環状オルがノ
ハイドロジェンシロキサンと一般式％式％
（式中、Ｒ，Ｒ”、Ｘおよびａは前記と同じ）で示され
るシランとを塩化白金酸のような白金系触媒で付加反応
させて、一般式
（式中、Ｒ，Ｒ’、Ｘ、 Ｖお上びａは前記と同じ）で
示（式中、Ｒ，Ｖは前記と同じ）で示される環状オルガ
ノハイドロジエンシロキサン、
一般式 、 。When the main 8 and 8 are both C, firstly, the cyclic ol represented by the general formula (wherein R and V are the same as above) is a hydrogen siloxane and the general formula % formula % (wherein R , R'', X, and a are the same as above) with a platinum-based catalyst such as chloroplatinic acid, and the general formula a is the same as above) (wherein R and V are the same as above);
）Ｉ ＳｉＯＳｉ Ｉ１
Ｒ
（式中、Ｒは前記と同じ）で示されるオルガツノ１（式
中、Ｒ％ ｙは前記と同じ）で示される環状オルガノハ
イドロジエンシロキサン（ｎがＯの場合には不要）とを
硫酸、硝酸、トリフルオロメタンスルホン酸、活性白土
のような酸性触媒により重合して、一般式
％式％
（式中、Ｒ，Ｒ１、Ｘ、 ａ、 ｌ、 翰およびｎは前
記と同じ）で示されるオルガノハイドロジエンポリシロ
キサンを合成する。) I SiOSi I1 R Cyclic organohydrodiene siloxane represented by organo1 (wherein R% y is the same as above) (in the formula, R% is the same as above) (unnecessary when n is O) and are polymerized using an acidic catalyst such as sulfuric acid, nitric acid, trifluoromethanesulfonic acid, or activated clay to obtain the general formula % (wherein R, R1, X, a, l, kan and n are the same as above) Synthesize an organohydrodiene polysiloxane represented by:
さらに、該オルガノハイドロジエンポリシロキサンと一
般式
％式％）
（式中、Ｒ２、Ｒ３、ｂおよびＣは前記と同じ）で示さ
れるアルケニル基含有ポリオキシアルキレンを白金系触
媒で付加反応させることにより本発明のオルガノポリシ
ロキサンが合成される。Furthermore, by subjecting the organohydrodiene polysiloxane to an addition reaction with an alkenyl group-containing polyoxyalkylene represented by the general formula % (in which R2, R3, b and C are the same as above) using a platinum-based catalyst. The organopolysiloxane of the present invention is synthesized.
［実施例１ 次に実施例により本発明を説明する。[Example 1 Next, the present invention will be explained with reference to Examples.
実施例１
還流冷却管を備えた５００ｍ１の３つロフラスコにビニ
ルＦリメｌ−キシシラン１４８，２ｇＱ仕込み、内温が
６（）℃になるまで加熱し、塩化白金酸２重量％イソプ
ロピルアルコール溶液０゜１５ｇを加え、テトラメチル
ジシロキサン５１゜８ｇを滴下した。その後１００℃で
２時間反応させ、１４０℃１５ｍｍＨｇで減圧蒸留して
、式％式％
で示されるオルガノジシロキサンＡを得た。Example 1 148.2gQ of vinyl Flimeryl-xysilane was charged into a 500ml three-bottle flask equipped with a reflux condenser, heated until the internal temperature reached 6()℃, and a 2% by weight isopropyl alcohol solution of chloroplatinic acid was added to the 0℃ solution. 15 g of tetramethyldisiloxane was added thereto, and 51.8 g of tetramethyldisiloxane was added dropwise. Thereafter, the mixture was reacted at 100° C. for 2 hours and distilled under reduced pressure at 140° C. and 15 mmHg to obtain organodisiloxane A represented by the formula %.
次に還流冷却管を備えた３０Ｑｔａｌの３つロフラスコ
に環状ジメチルポリシロキサン７９ｇ環状メチルハイド
ロジエンシロキサン４ＨＨ。Next, 79 g of cyclic dimethylpolysiloxane 4HH was added to a 30 Qtal three-bottle flask equipped with a reflux condenser.
６ｇ、オルガノジシロキサンＡ１６．４ｇ、および触媒
としてトリフルオロメタンスルホン酸０゜００２ｇを仕
込み６０℃で３時間重合させた。6g of organodisiloxane A, and 0.002g of trifluoromethanesulfonic acid as a catalyst were charged and polymerized at 60°C for 3 hours.
その後炭酸カルシウム４ｇを加え触媒を中和後、助剤ろ
過を行なった。Thereafter, 4 g of calcium carbonate was added to neutralize the catalyst, followed by filtration with an auxiliary agent.
犬に、この生成物４６ｇと式
％式％
で示されるアリル基含有ポリオキシアルキレン８２６ｇ
、およびトルエン２０ｇを仕込み、内温が８５°Ｃにな
るまで加熱し、塩化白金酸２重量％イソプロピルアルコ
ール溶液０．０９ｇを加えた。その後１１５℃で２時間
反応させた。Dogs were given 46 g of this product and 826 g of allyl group-containing polyoxyalkylene of the formula %.
, and 20 g of toluene were charged, heated until the internal temperature reached 85°C, and 0.09 g of a 2% by weight solution of chloroplatinic acid in isopropyl alcohol was added. Thereafter, the mixture was reacted at 115° C. for 2 hours.
ついで、１３０℃／ １５ ｍ＋ａＨｇで揮発分を減圧
除去した後、遠心分離して未反応のアリル基含有ポリオ
キシアルキレンＢを除去したところ、粘度１１４ＣＳ（
２５℃）、屈折率１．４３１０（２５℃）を有する油状
物が得られた。このものは下記の赤外線吸収分析および
核磁気共鳴分析結果より式
％式％
で示されるオルガノポリシロキサンであることが確認さ
れた。Next, volatile components were removed under reduced pressure at 130°C/15 m+aHg, and then centrifuged to remove unreacted allyl group-containing polyoxyalkylene B, resulting in a viscosity of 114CS (
An oil having a refractive index of 1.4310 (25°C) was obtained. This product was confirmed to be an organopolysiloxane represented by the formula % from the results of infrared absorption analysis and nuclear magnetic resonance analysis described below.
赤外線吸収（ＩＲ）スペクトル分析（第１図参照）２９
００ｃｍ”” メチレン基、５ｉ−Ｃ貼基、伸縮振
動（強度大）
１７４０ｃｍ−’ ｃ＝ｏ 伸縮振動（強度中
）１２６０ｅ＋ｏ−’ ５ｉＣＬ 変角振動（
強度大）１１００ｃｍ−’ ５ｉＯＳｉ 変角
振動（強度大）８００ｃｍ−’ ５ｉ−Ｃｔｌ、変
角振動（強度大）核磁気共鳴（ＮＭＲ）スペクトル分析
（第２図参照）δ＝ ０ 、３ ｏ ｐ ｍ Ｓ ＋
Ｃｔｌ ３３．５ｐｐｍ Ｃ−ＣＨ２０，５ｉ−
ＯＣＩＩ３実施例２
還流冷却管を備えた５００ｍ１の３つロアう久コにビニ
ルトリメトキシシラン２９６．４ｇを仕込み、内温か６
０°Ｃになるまで加熱して塩化白金酸２重量％イソプロ
ピルアルコール溶液０゜０９６ヲｊｌｌえ、環状メチル
ハイドロジエンシロキサン４量体６０． １ｇを滴下し
た。その後１３０℃／ １５ ＋ｎｍＨｇで未反応のビ
ニルトリメトキシシランを減圧除去して、式
で示される環状オルガノシロキサン４量体Ｃを得た。Infrared absorption (IR) spectrum analysis (see Figure 1)29
00cm"" Methylene group, 5i-C adhesive group, stretching vibration (high intensity) 1740cm-' c=o stretching vibration (medium intensity) 1260e+o-' 5iCL bending vibration (
5i-Ctl, bending vibration (high intensity) nuclear magnetic resonance (NMR) spectrum analysis (see Figure 2) δ = 0, 3 o p m S+
Ctl 33.5ppm C-CH20,5i-
OCII3 Example 2 296.4g of vinyltrimethoxysilane was charged into a 500ml three-lower chamber equipped with a reflux condenser, and the internal temperature was 6.
Heat to 0°C and add 2% by weight isopropyl alcohol solution of chloroplatinic acid to 60°C of cyclic methylhydrogensiloxane tetramer. 1 g was added dropwise. Thereafter, unreacted vinyltrimethoxysilane was removed under reduced pressure at 130° C./ 15 +nmHg to obtain a cyclic organosiloxane tetramer C represented by the formula.
次に還流冷却管を備えた３００ｍ１の３つロフラスコに
環状オルガノシロキサン４量体Ｃ１５゜８ｇ、環状ジメ
チルポリシロキサン７９．１ｇ。Next, in a 300 ml three-bottle flask equipped with a reflux condenser, 8 g of cyclic organosiloxane tetramer C15° and 79.1 g of cyclic dimethylpolysiloxane were added.
テトラメチルジシロキサン５．１ｇおよび重合触媒とし
てトリフルオロメタンスルホン酸０゜００２ ｇを仕込
み６０ ’Ｃで３時間重合させた。5.1 g of tetramethyldisiloxane and 0.002 g of trifluoromethanesulfonic acid as a polymerization catalyst were charged and polymerized at 60'C for 3 hours.
その後炭酸カルシウム２ｇを加え触媒を中和後、助剤ろ
過を行なった。Thereafter, 2 g of calcium carbonate was added to neutralize the catalyst, and filtration with an aid was performed.
次に、この生成物６０．３ｇと実施例１で用いたアリル
基含有ポリオキシアルキレン８３４゜５ｇ、およびトル
エン３０ｇを仕込み、内温が８５°Ｃになるまで加熱し
、塩化白金酸２重量％イソプロピルアルコール溶液０．
１２ｇを加えた。Next, 60.3 g of this product, 834.5 g of allyl group-containing polyoxyalkylene used in Example 1, and 30 g of toluene were charged, heated until the internal temperature reached 85°C, and 2% by weight of chloroplatinic acid was added. Isopropyl alcohol solution 0.
Added 12g.
その後１１５℃で２時間反応させた。Thereafter, the mixture was reacted at 115° C. for 2 hours.
圧除去した後、遠心分離して未反応のアリル基含有ポリ
オキシアルキレンＢを除去したところ、粘度３００ＣＳ
（２５℃）、屈折率１．４３１０（２５℃）を有する油
状物が得られた。このものは下記の分析結果上り式
％式％）
で示されるオルガノポリシロキサンであることが確認さ
れた。After pressure removal, unreacted allyl group-containing polyoxyalkylene B was removed by centrifugation, and the viscosity was 300CS.
(25°C), an oil having a refractive index of 1.4310 (25°C) was obtained. This product was confirmed to be an organopolysiloxane shown by the following analytical results.
赤外線吸収（踵）スペクトル分析（第３図参照）２９０
０ｃ＋ｎ−’付近 メチレン基、Ｓ’５−ｅｌｌｓ基、
伸縮振動（強度大）
１７４０ｃｍ−’ Ｃ＝０ 伸縮振動（強度中
）１２６０ｃｍ−’ ５ｉＣ１ｌ： 変角振動
（強度大）１１００ｃｍ−’ Ｓｉ ＯＳｉ 変角
振動（強度大）８００ｃｍ−’ Ｓｉ −Ｃ１ｌｚ
変角振動（強度大）磁気共鳴（ＮＨＲ）スペクトル分
析（第４図参照）δ＝０．３ｐｐｍ ５ｉ−ｃｌ＋３
３．５ｐｐｍ ＣＣ）＋２０１ Ｓｉ ０Ｃ１ｌ＋
実施外３
還流冷却管を備えすこ５００ｍ１の３つロフラスコに実
施例１で合成したオルガノジシロキサンＡ６１．４ｇ、
環状メチルハイドロジエンシロキサン４量体５９．８ｇ
および環状ジメチルシロキサン４１体３６８．９ｇ、ま
た重合触媒として充分乾燥させた活性白土１５ｇを仕込
み７５℃で１０時間重合した。その後冷却して助剤ろ過
を行なった。次に得られたオルガノジシロキサン１３６
．９ｇ、ビニルトリメトキシシラン１３．４ｇ、式
％式％
で示されるアリル基含有ポリオキシアルキレン１４９．
７ｇとトルエン９０ｇを還流冷却管を備えｐ、５００ｍ
１の３つロフラスコに仕込み、内温か６０″Ｃになる主
で加熱して、塩化白金酸２重量％イソプロピルアルコー
ル溶１０．３８ｇを加えた。その後１２０℃で２時間反
応させた。Infrared absorption (heel) spectrum analysis (see Figure 3) 290
Near 0c+n-' methylene group, S'5-ells group,
Stretching vibration (high intensity) 1740cm-' C=0 Stretching vibration (medium intensity) 1260cm-' 5iC1l: Bending vibration (high intensity) 1100cm-' Si OSi Bending vibration (high intensity) 800cm-' Si -C1lz
Bending vibration (high intensity) magnetic resonance (NHR) spectrum analysis (see Figure 4) δ=0.3ppm 5i-cl+3 3.5ppm CC)+201 Si 0C1l+
Non-implementation 3 61.4 g of organodisiloxane A synthesized in Example 1 was placed in a 500 ml three-bottle flask equipped with a reflux condenser.
Cyclic methylhydrogensiloxane tetramer 59.8g
Then, 368.9 g of 41 cyclic dimethylsiloxanes and 15 g of sufficiently dried activated clay as a polymerization catalyst were charged and polymerized at 75° C. for 10 hours. Thereafter, it was cooled and filtered with an aid. Organodisiloxane 136 obtained next
．． 9 g, vinyltrimethoxysilane 13.4 g, allyl group-containing polyoxyalkylene represented by the formula % formula % 149.
7g and toluene 90g equipped with a reflux condenser pipe, 500m
1 was placed in a three-bottle flask, heated to an internal temperature of 60''C, and 10.38g of 2% by weight chloroplatinic acid in isopropyl alcohol was added.Then, the mixture was reacted at 120°C for 2 hours.
反応終了後、揮発分を減圧除去したところ、粘度３０５
ＣＳ（２５℃）、屈折率１．４３９２（２５℃）を有す
る油状物が得られた。このものは下記の赤外線吸収分析
および核磁気共鳴分析結果より式
で示されるオルがノボリシロキサンであることが確認さ
れた。After the reaction was completed, volatile components were removed under reduced pressure, and the viscosity was 305.
An oil was obtained having a CS (25°C) and a refractive index of 1.4392 (25°C). In this product, it was confirmed from the results of infrared absorption analysis and nuclear magnetic resonance analysis described below that ol represented by the formula was novolisiloxane.
赤外線吸収（ＩＲ）スペクトル分析（第５図参照）２９
００ｃＩ１１−１ メチレン基−Ｓ！ Ｃｔｌｚ
基、伸縮振動（強度大）
１２６０ｃｍ−’ ５ｉＣｌ１２ 変角振！Ｉ
！ＩＩ （強度大）１１００ｃｍ−’ ５ｉＯＳｉ
変角振動（強度大）８００ｃｍ−’ ５ｉ−
ＣＬ 変角振動（強度大）核磁気共鳴（ＮＭＲ）スペク
トル分析（第６図参照）δ＝０．３ｐｐｍ Ｓｉ
ＣＬ
３．５ｐｐｍ Ｃ−ＣＬＯｔ Ｓｉ −０ＣＬ［発明
の効果１
本発明によれば、分子鎖末端がフルフキシシリルアルキ
ル基もしくはポリオキシアルキレン基であって、１分子
中にフルコキシシリルアルキル基およびポリオキシアル
キレン基を有するアルフキシシリルフルキル・ポリオキ
シフルキレン変性オルガノジシロキサンを提供すること
がでトる。本発明のフルコキシシリルアルキル・ポリオ
キシアルキレン変性オルガノジシロキサンは優れた反応
性および親水性を有するのでシーラント、エラスＦマー
などの原料として、また各種多様の基材の処理剤として
、あるいは各種樹脂やゴムの添加剤として好適に使用す
ることができる。Infrared absorption (IR) spectrum analysis (see Figure 5) 29
00cI11-1 Methylene group-S! Ctlz
Base, stretching vibration (high intensity) 1260cm-' 5iCl12 Bending angle vibration! I
! II (high strength) 1100cm-' 5iOSi
Bending angle vibration (high intensity) 800cm-' 5i-
CL Bending vibration (high intensity) nuclear magnetic resonance (NMR) spectrum analysis (see Figure 6) δ = 0.3 ppm Si
CL 3.5ppm C-CLOt Si -0CL [Effect of the invention 1 According to the present invention, the molecular chain terminal is a flukoxysilylalkyl group or a polyoxyalkylene group, and one molecule contains a flukoxysilylalkyl group and a polyoxyalkylene group. It is possible to provide an alfoxysilylfurkyl polyoxyfulkylene modified organodisiloxane having an oxyalkylene group. The flukoxysilylalkyl/polyoxyalkylene-modified organodisiloxane of the present invention has excellent reactivity and hydrophilicity, so it can be used as a raw material for sealants, elas Fmer, etc., and as a treatment agent for various base materials, and for various resins. It can be suitably used as an additive for rubber.
第１図、第３図および第５図はそれぞれ実施例１、実施
例２および実施例３で得られた生成物の赤外線吸収スペ
クトル分析結果を示すものである。
また、第２図、第４図および第６図はそれぞれ実施例１
、実施例２および実施例３で得られた生成物の核磁気共
鳴スペクトル分析結果を示すものである。
第２図
ｐｐｍ
第４図
ｐｍFIG. 1, FIG. 3, and FIG. 5 show the results of infrared absorption spectrum analysis of the products obtained in Example 1, Example 2, and Example 3, respectively. Moreover, FIG. 2, FIG. 4, and FIG. 6 are respectively Example 1.
, which shows the results of nuclear magnetic resonance spectroscopy of the products obtained in Example 2 and Example 3. Figure 2 ppm Figure 4 pm
Claims (1)
およびＡ′は共にＱもしくは共にＧであり、Ｑは式 ▲数式、化学式、表等があります▼ で示される基、Ｘは炭素原子数１〜４のアルコキシ基、
Ｒ＾１は炭素原子数２〜５のアルキレン基、ａは２また
は３、Ｇは式 −Ｒ＾１−Ｏ−（Ｃ＿２Ｈ＿４Ｏ）ｂ−（Ｃ＿３Ｈ＿６
Ｏ）ｃ−Ｒ＾２で示される基、Ｒ＾２は水素原子もしく
は炭素原子数１〜５の一価有機基、ｂおよびｃは０〜１
００の整数、ただしｂ＋ｃは２〜２００の整数である。 ｌは１〜５００の整数、ｍは０〜１００の整数、ｎは０
〜１００の整数、ただしＡおよびＡ′が共にＱである場
合、ｎは１〜１００の整数であり、ＡおよびＡ′が共に
Ｇである場合、ｍは１〜１００の整数である。］で表わ
されるアルコキシシリルアルキル・ポリオキシアルキレ
ン変性オルガノポリシロキサン。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R is a monovalent hydrocarbon group having 1 to 10 carbon atoms, A
and A' are both Q or both G, Q is a group represented by the formula ▲ Numerical formula, chemical formula, table, etc. ▼, X is an alkoxy group having 1 to 4 carbon atoms,
R^1 is an alkylene group having 2 to 5 carbon atoms, a is 2 or 3, and G is the formula -R^1-O-(C_2H_4O)b-(C_3H_6
O) A group represented by c-R^2, R^2 is a hydrogen atom or a monovalent organic group having 1 to 5 carbon atoms, b and c are 0 to 1
An integer of 00, where b+c is an integer of 2 to 200. l is an integer from 1 to 500, m is an integer from 0 to 100, n is 0
an integer from 1 to 100, where A and A' are both Q, n is an integer from 1 to 100, and when A and A' are both G, m is an integer from 1 to 100. ] An alkoxysilylalkyl/polyoxyalkylene-modified organopolysiloxane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6805586A JPS62225533A (en) | 1986-03-26 | 1986-03-26 | Organopolysiloxane modified with alkoxysilylalkyl polyoxyalkylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6805586A JPS62225533A (en) | 1986-03-26 | 1986-03-26 | Organopolysiloxane modified with alkoxysilylalkyl polyoxyalkylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62225533A true JPS62225533A (en) | 1987-10-03 |
Family
ID=13362709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6805586A Pending JPS62225533A (en) | 1986-03-26 | 1986-03-26 | Organopolysiloxane modified with alkoxysilylalkyl polyoxyalkylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62225533A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994006807A1 (en) * | 1992-09-16 | 1994-03-31 | E.I. Du Pont De Nemours And Company | Single component inorganic/organic network materials and precursors thereof |
| EP0890598A1 (en) * | 1996-12-27 | 1999-01-13 | The Yokohama Rubber Co., Ltd. | Modified polysiloxanes, rubber compositions and tire tread rubber compositions containing the same, and reactive plasticizer |
| JP2010031071A (en) * | 2008-07-25 | 2010-02-12 | Shin-Etsu Chemical Co Ltd | Manufacturing method of hydrolyzable group-containing organohydrogenpolysiloxane, and organopolysiloxane obtained by addition reaction to organohydrogenpolysiloxane |
| JP2011241291A (en) * | 2010-05-18 | 2011-12-01 | Tosoh Corp | Cyclic polysiloxane, method for producing the same, and use thereof |
| JP2013010972A (en) * | 2012-10-18 | 2013-01-17 | Shin-Etsu Chemical Co Ltd | Method for producing organopolysiloxane |
| JP2017088808A (en) * | 2015-11-16 | 2017-05-25 | 信越化学工業株式会社 | Novel silicone compound, and cosmetic containing the same |
| WO2018016565A1 (en) * | 2016-07-22 | 2018-01-25 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Surface treatment agent for thermally conductive polyorganosiloxane composition |
| US20210147681A1 (en) | 2016-07-22 | 2021-05-20 | Momentive Performance Materials Japan Llc | Thermally conductive polysiloxane composition |
| US11254849B2 (en) | 2015-11-05 | 2022-02-22 | Momentive Performance Materials Japan Llc | Method for producing a thermally conductive polysiloxane composition |
| US11359124B2 (en) | 2017-05-31 | 2022-06-14 | Momentive Performance Materials Japan Llc | Thermally conductive polysiloxane composition |
-
1986
- 1986-03-26 JP JP6805586A patent/JPS62225533A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994006807A1 (en) * | 1992-09-16 | 1994-03-31 | E.I. Du Pont De Nemours And Company | Single component inorganic/organic network materials and precursors thereof |
| EP0890598A1 (en) * | 1996-12-27 | 1999-01-13 | The Yokohama Rubber Co., Ltd. | Modified polysiloxanes, rubber compositions and tire tread rubber compositions containing the same, and reactive plasticizer |
| EP0890598A4 (en) * | 1996-12-27 | 1999-09-29 | Yokohama Rubber Co Ltd | Modified polysiloxanes, rubber compositions and tire tread rubber compositions containing the same, and reactive plasticizer |
| JP2010031071A (en) * | 2008-07-25 | 2010-02-12 | Shin-Etsu Chemical Co Ltd | Manufacturing method of hydrolyzable group-containing organohydrogenpolysiloxane, and organopolysiloxane obtained by addition reaction to organohydrogenpolysiloxane |
| JP2011241291A (en) * | 2010-05-18 | 2011-12-01 | Tosoh Corp | Cyclic polysiloxane, method for producing the same, and use thereof |
| JP2013010972A (en) * | 2012-10-18 | 2013-01-17 | Shin-Etsu Chemical Co Ltd | Method for producing organopolysiloxane |
| US11254849B2 (en) | 2015-11-05 | 2022-02-22 | Momentive Performance Materials Japan Llc | Method for producing a thermally conductive polysiloxane composition |
| JP2017088808A (en) * | 2015-11-16 | 2017-05-25 | 信越化学工業株式会社 | Novel silicone compound, and cosmetic containing the same |
| US20210147681A1 (en) | 2016-07-22 | 2021-05-20 | Momentive Performance Materials Japan Llc | Thermally conductive polysiloxane composition |
| US11118056B2 (en) | 2016-07-22 | 2021-09-14 | Momentive Performance Materials Japan Llc | Thermally conductive polysiloxane composition |
| WO2018016565A1 (en) * | 2016-07-22 | 2018-01-25 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | Surface treatment agent for thermally conductive polyorganosiloxane composition |
| US11286349B2 (en) | 2016-07-22 | 2022-03-29 | Momentive Performance Materials Japan Llc | Surface treatment agent for thermally conductive polyorganosiloxane composition |
| US11359124B2 (en) | 2017-05-31 | 2022-06-14 | Momentive Performance Materials Japan Llc | Thermally conductive polysiloxane composition |
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