KR970027094A - 비스(실릴알킬)-디설판의 제조방법 - Google Patents
비스(실릴알킬)-디설판의 제조방법 Download PDFInfo
- Publication number
- KR970027094A KR970027094A KR1019960052353A KR19960052353A KR970027094A KR 970027094 A KR970027094 A KR 970027094A KR 1019960052353 A KR1019960052353 A KR 1019960052353A KR 19960052353 A KR19960052353 A KR 19960052353A KR 970027094 A KR970027094 A KR 970027094A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- silylalkyl
- polysulfide
- reaction
- process according
- Prior art date
Links
- 125000005353 silylalkyl group Chemical group 0.000 title claims 5
- 238000000034 method Methods 0.000 claims abstract 6
- 229920001021 polysulfide Polymers 0.000 claims abstract 5
- 239000005077 polysulfide Substances 0.000 claims abstract 5
- 150000008117 polysulfides Polymers 0.000 claims abstract 5
- -1 silylalkyl disulfide Chemical compound 0.000 claims abstract 3
- 239000012434 nucleophilic reagent Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 150000003961 organosilicon compounds Chemical class 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000003009 desulfurizing effect Effects 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
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
- C07F7/0898—Compounds with a Si-S linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
본 발명은 친핵성 시약을 사용하여 상응하는 폴리설파이드를 탈황시켜 실릴알킬디설파이드를 선택적으로 합성하는 방법에 관한 것이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 화학식 (2)실릴알킬폴리설파이드 또는 실릴알킬폴리설파이드의 혼합물과 화학식 (3), 화학식 (4) 또는 화학식 (5)의 친핵성 화합물을, 화학식 (3) 내지 (5)의 화합물을 화학식 (2)의 화합물로부터 제거되는 황 원자에 대해서 등몰량으로 사용하여 반응시키고, 생성된 고체를 여과한 다음, 수득한 디설판을 정제함을 특징으로 하여, 화학식 (1)의 비스(실릴알킬)-디설판을 제조하는 방법.(R1R2R3SiR4)2S2(1)(R1R2R3SiR4)2Sn(2)M+CN-(3)M+ 2SO2 3 -(4)R5R6R7P (5)상기 화학식 (1) 내지 화학식 (5)에서, R1, R2및 R3은 탄소수 1 내지 8의 동일하거나 상이한 측쇄 또는 비측쇄 알킬 및/또는 알콕시 그룹, 수소 또는 1가 아릴 잔기, 특히 페닐, 톨릴, 벤질이고, R4는 탄소수 1 내지 8, 바람직하게는 2 내지 4의 2가 알킬리덴 잔기 또는이며, n은 3 내지 20, 특히 3 내지 10의 정수이고, M+는 알칼리 금속 양이온, 치환되거나 치환되지 않은 암모늄 이온 또는 1/2알칼리 토금속 이온 또는 아연 이온이며, R5, R6및 R7은 화학식 (1)의 R1, R2및 R3과 동일하다.
- 제1항에 있어서, 화학식 (3) 내지 화학식 (5)의 화합물이 혼합물로서 사용됨을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 반응이 친핵성 화합물을 용해시키는 용매의 존재하에 수행됨을 특징으로 하는 방법.
- 제1항 내지 3항 중의 어느 한 항에 있어서, 반응이 20℃ 내지 사용되는 용매의 지점에서 수행됨을 특징으로 하는 방법.
- 제1항 내지 제4항 중의 어느 한 항에 있어서, 반응이 이상 시스템에서 상 이동 촉매 존재하에 수행됨을 특징으로 하는 방법.
- 제1항에 있어서, 반응되는 화학식 (2)의 실릴알킬폴리설판이, 화학식 M+ 2Sn의 폴리설파이드 또는 폴리설파이드 혼합물(여기서, M+및 n은 위에서 정의한 바와 동일하다)(a), M+CN-,M+ 2SO2 3 -및 R5R6R7P 로 부터의 친핵성 시약(여기서, M+, R5, R6및 R7은 그위에서 정의한 바와 동일하다)(개별적으로 또는 함께) 및 화학식 (6)의 유기 규소 화합물(c)을 (a) 0.4 내지 0.7: (b) 1내지 1.1: (c) 1의 몰 비로 함유하는 용액을 제조함으로써 동일 반응계 내에서 합성되고, 혼합물이 함께 반응하며, 목적하는 디설파이드가 통상적인 정제로 분리됨을 특징으로 하는 방법Cl-R4-Si(R1R2R3)3(6)상기 화학식 (6)에서 R1, R2, R3및 R4는 위에서 정의한 바와 동일하다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US60/007,307 | 1995-11-06 | ||
DE19541404A DE19541404A1 (de) | 1995-11-07 | 1995-11-07 | Verfahren zur selektiven Synthese von Silylalkyldisulfiden |
DE19541404.7 | 1995-11-07 | ||
DE19543478.1 | 1995-11-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR970027094A true KR970027094A (ko) | 1997-06-24 |
Family
ID=7776798
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960052353A KR970027094A (ko) | 1995-11-06 | 1996-11-06 | 비스(실릴알킬)-디설판의 제조방법 |
Country Status (18)
Country | Link |
---|---|
US (1) | US5663395A (ko) |
EP (1) | EP0773224B1 (ko) |
JP (1) | JPH09169774A (ko) |
KR (1) | KR970027094A (ko) |
CN (1) | CN1070862C (ko) |
AU (1) | AU713295B2 (ko) |
BR (1) | BR9605476A (ko) |
CA (1) | CA2189601A1 (ko) |
CZ (1) | CZ318096A3 (ko) |
DE (2) | DE19541404A1 (ko) |
ES (1) | ES2168424T3 (ko) |
HR (1) | HRP960516B1 (ko) |
HU (1) | HU217297B (ko) |
PL (1) | PL183494B1 (ko) |
PT (1) | PT773224E (ko) |
SI (1) | SI0773224T1 (ko) |
SK (1) | SK143596A3 (ko) |
TW (1) | TW382018B (ko) |
Families Citing this family (51)
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KR100361933B1 (ko) | 1993-09-08 | 2003-02-14 | 라 졸라 파마슈티칼 컴파니 | 화학적으로정의된비중합성결합가플랫폼분자및그것의콘주게이트 |
EP0819694B1 (de) | 1996-07-18 | 2002-10-02 | Degussa AG | Gemische von Organilanpolysulfanen und ein Verfahren zur Herstellung von diese Gemische enthaltenden Kautschukmischungen |
JP3388531B2 (ja) * | 1996-11-29 | 2003-03-24 | 信越化学工業株式会社 | ポリスルフィドシランの脱硫方法 |
DE19732725A1 (de) * | 1997-07-30 | 1999-02-04 | Degussa | Mischungen, bestehend aus Bis(silylorganyl)polysulfanen und Silylorganylthiocyanaten, ihre Herstellung und Verwendung |
DE19734295C1 (de) * | 1997-08-08 | 1999-02-25 | Degussa | Verfahren zur Herstellung von Organosiliciumdisulfanen hoher Reinheit |
JP3465558B2 (ja) * | 1997-09-26 | 2003-11-10 | 信越化学工業株式会社 | ポリスルフィドシランの製造方法 |
DE19750503A1 (de) * | 1997-11-14 | 1999-05-20 | Degussa | Verfahren zur Reduzierung der Sulfankettenlänge von Bis(silylorganyl)polysulfanen |
DE19819373A1 (de) * | 1998-04-30 | 1999-11-04 | Degussa | Verfahren zur Herstellung von Gemischen von Organosiliciumoligosulfanen mit einem hohen Anteil an Organanosiliciumdisulfanen |
DE19848482C1 (de) * | 1998-10-21 | 2000-06-08 | Degussa | Verfahren zur Herstellung von Organosiliciumdisulfanen |
DE19905820A1 (de) * | 1998-10-27 | 2000-05-04 | Degussa | Schwefelfunktionelle Polyorganosilane |
US6458953B1 (en) * | 1998-12-09 | 2002-10-01 | La Jolla Pharmaceutical Company | Valency platform molecules comprising carbamate linkages |
US6399578B1 (en) * | 1998-12-09 | 2002-06-04 | La Jolla Pharmaceutical Company | Conjugates comprising galactose α1,3 galactosyl epitopes and methods of using same |
US20010010818A1 (en) * | 1998-12-09 | 2001-08-02 | Engle Steven B. | Methods and formulations for reducing circulating antibodies |
CA2376057A1 (en) * | 1999-06-08 | 2000-12-14 | La Jolla Pharmaceutical Company | Valency platform molecules comprising aminooxy groups |
US6452034B2 (en) | 2000-01-04 | 2002-09-17 | Crompton Corporation | Low-sulfur polysulfide silanes and process for preparation |
US6518335B2 (en) | 2000-01-05 | 2003-02-11 | Crompton Corporation | Sulfur-containing silane coupling agents |
FR2804120A1 (fr) * | 2000-01-24 | 2001-07-27 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant une charge blanche renforcante et un systeme de couplage (charge blanche/elstomere) |
FR2804121A1 (fr) | 2000-01-24 | 2001-07-27 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant une charge blanche renforcante et un systeme de couplage ( charge blanche/elastomere) |
DE10015308A1 (de) * | 2000-03-28 | 2001-10-11 | Degussa | Kautschukmischungen |
JP5113970B2 (ja) | 2000-04-25 | 2013-01-09 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | タイヤに使用できるゴム組成物用ブロックコポリマー |
CN101307162B (zh) * | 2000-05-22 | 2014-03-19 | 米其林集团总公司 | 轮胎行驶胎面的组合物以及它的制造方法 |
CA2414076A1 (en) | 2000-06-08 | 2001-12-13 | La Jolla Pharmaceutical Company | Multivalent platform molecules comprising high molecular weight polyethylene oxide |
US6359046B1 (en) | 2000-09-08 | 2002-03-19 | Crompton Corporation | Hydrocarbon core polysulfide silane coupling agents for filled elastomer compositions |
JP4209200B2 (ja) * | 2001-03-12 | 2009-01-14 | ソシエテ ド テクノロジー ミシュラン | タイヤトレッド用ゴム組成物 |
FR2823210B1 (fr) * | 2001-04-10 | 2005-04-01 | Rhodia Chimie Sa | Organoxysilanes polysulfures utilisables notamment en tant qu'agent de couplage, compositions d'elastomere(s) les contenant et articles en elastomere(s) prepares a partir de telles compositions |
DE10122269A1 (de) | 2001-05-08 | 2002-11-21 | Degussa | Silanmodifizierter biopolymerer, biooligomerer, oxidischer oder silikatischer Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung |
JP4536375B2 (ja) * | 2001-06-28 | 2010-09-01 | ソシエテ ド テクノロジー ミシュラン | 極めて低い比表面積のシリカで強化されたタイヤトレッド |
CN1547601B (zh) * | 2001-06-28 | 2012-09-05 | 米其林技术公司 | 采用具有低比表面积的二氧化硅增强的轮胎胎面 |
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DE10218350A1 (de) | 2002-04-25 | 2003-11-20 | Degussa | Silanmodifizierter oxidischer oder silikatischer Füllstoff, Verfahren zu seiner Herstellung und seine Verwendung |
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US7968633B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing free-flowing filler compositions |
US7968634B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing silated core polysulfides |
US8592506B2 (en) | 2006-12-28 | 2013-11-26 | Continental Ag | Tire compositions and components containing blocked mercaptosilane coupling agent |
US7968635B2 (en) | 2006-12-28 | 2011-06-28 | Continental Ag | Tire compositions and components containing free-flowing filler compositions |
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-
1995
- 1995-11-07 DE DE19541404A patent/DE19541404A1/de not_active Withdrawn
-
1996
- 1996-09-23 PT PT96115226T patent/PT773224E/pt unknown
- 1996-09-23 DE DE59608364T patent/DE59608364D1/de not_active Expired - Fee Related
- 1996-09-23 ES ES96115226T patent/ES2168424T3/es not_active Expired - Lifetime
- 1996-09-23 EP EP96115226A patent/EP0773224B1/de not_active Expired - Lifetime
- 1996-09-23 SI SI9630415T patent/SI0773224T1/xx unknown
- 1996-10-30 TW TW085113256A patent/TW382018B/zh not_active IP Right Cessation
- 1996-10-30 CZ CZ963180A patent/CZ318096A3/cs unknown
- 1996-10-30 PL PL96316746A patent/PL183494B1/pl unknown
- 1996-11-04 CN CN96120660A patent/CN1070862C/zh not_active Expired - Fee Related
- 1996-11-05 HR HR960516A patent/HRP960516B1/xx not_active IP Right Cessation
- 1996-11-05 CA CA002189601A patent/CA2189601A1/en not_active Abandoned
- 1996-11-05 JP JP8292755A patent/JPH09169774A/ja not_active Abandoned
- 1996-11-05 US US08/743,842 patent/US5663395A/en not_active Expired - Fee Related
- 1996-11-06 AU AU70624/96A patent/AU713295B2/en not_active Ceased
- 1996-11-06 HU HU9603081A patent/HU217297B/hu not_active IP Right Cessation
- 1996-11-06 SK SK1435-96A patent/SK143596A3/sk unknown
- 1996-11-06 KR KR1019960052353A patent/KR970027094A/ko not_active Application Discontinuation
- 1996-11-07 BR BR9605476A patent/BR9605476A/pt active Search and Examination
Also Published As
Publication number | Publication date |
---|---|
HUP9603081A2 (en) | 1997-10-28 |
JPH09169774A (ja) | 1997-06-30 |
ES2168424T3 (es) | 2002-06-16 |
HRP960516B1 (en) | 2002-04-30 |
PT773224E (pt) | 2002-05-31 |
CZ318096A3 (en) | 1997-05-14 |
DE59608364D1 (de) | 2002-01-17 |
BR9605476A (pt) | 1998-08-11 |
HRP960516A2 (en) | 1998-02-28 |
EP0773224B1 (de) | 2001-12-05 |
EP0773224A2 (de) | 1997-05-14 |
HU9603081D0 (en) | 1996-12-30 |
CN1070862C (zh) | 2001-09-12 |
EP0773224A3 (de) | 1998-03-18 |
AU7062496A (en) | 1997-05-15 |
DE19541404A1 (de) | 1997-05-15 |
PL183494B1 (pl) | 2002-06-28 |
TW382018B (en) | 2000-02-11 |
CA2189601A1 (en) | 1997-05-08 |
SK143596A3 (en) | 1997-05-07 |
PL316746A1 (en) | 1997-05-12 |
HUP9603081A3 (en) | 1998-09-28 |
SI0773224T1 (en) | 2002-06-30 |
AU713295B2 (en) | 1999-11-25 |
US5663395A (en) | 1997-09-02 |
CN1156149A (zh) | 1997-08-06 |
HU217297B (hu) | 1999-12-28 |
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