DE2141159C3 - Organosilicon compounds containing sulfur - Google Patents

Organosilicon compounds containing sulfur

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Publication number
DE2141159C3
DE2141159C3 DE19712141159 DE2141159A DE2141159C3 DE 2141159 C3 DE2141159 C3 DE 2141159C3 DE 19712141159 DE19712141159 DE 19712141159 DE 2141159 A DE2141159 A DE 2141159A DE 2141159 C3 DE2141159 C3 DE 2141159C3
Authority
DE
Germany
Prior art keywords
organosilicon compounds
compounds containing
compounds
containing sulfur
reaction
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.)
Expired
Application number
DE19712141159
Other languages
German (de)
Other versions
DE2141159B2 (en
DE2141159A1 (en
Inventor
Friedrich Dr. 6454 Grossauheim Thurn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE787691D priority Critical patent/BE787691A/en
Application filed by Degussa GmbH filed Critical Degussa GmbH
Priority to DE19712141159 priority patent/DE2141159C3/en
Priority to SU1791182A priority patent/SU511863A3/en
Priority to FR7219496A priority patent/FR2149339B1/fr
Priority to DD163594A priority patent/DD99585A5/xx
Priority to ES403883A priority patent/ES403883A1/en
Priority to NL7209035A priority patent/NL151995B/en
Priority to US00277043A priority patent/US3842111A/en
Priority to BR5584/72A priority patent/BR7205584A/en
Priority to CS568972A priority patent/CS188151B2/en
Priority to IT52209/72A priority patent/IT962125B/en
Priority to JP47082444A priority patent/JPS5128623B2/ja
Priority to AT710372A priority patent/AT315874B/en
Priority to GB3838672A priority patent/GB1394135A/en
Publication of DE2141159A1 publication Critical patent/DE2141159A1/en
Priority to US415176A priority patent/US3873489A/en
Priority to US05/467,583 priority patent/US3978103A/en
Publication of DE2141159B2 publication Critical patent/DE2141159B2/en
Priority to US05/529,568 priority patent/US3997356A/en
Priority to US05/690,150 priority patent/US4076550A/en
Application granted granted Critical
Publication of DE2141159C3 publication Critical patent/DE2141159C3/en
Expired legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • 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 System
    • 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
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/16—Sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/62—Submicrometer sized, i.e. from 0.1-1 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/12—Surface area

Description

Na2S4 Na 2 S 4

ίοίο

2. Verfahren zur Herstellung der im Anspruch 1 genannten Verbindungen, dadurch gekennzeichnet, is daß man2. Process for the preparation of the compounds mentioned in claim 1, characterized in that is that he

3-Chlorpropyltriäthoxysilan,3-chloropropyltriethoxysilane,

3-Chlorpropyltrimethoxysilanbzw.3-chloropropyltrimethoxysilane or

2-ChloräthyltriäthoxysiIan2-ChloräthyltriethoxysiIan

2020th

2525th

im Molverhältnis 2:1 in an sich bekannter Weise umsetzt.in a molar ratio of 2: 1 in a known manner.

3030th

Es ist bekannt, Organosiliciumverbindungen wie 3-Mercaptopropyltrimethoxysilan als Haftvermittler in Kautschukmischungen zu verwenden. Vorteilhaft fällt bei der Anwendung solcher Verbindungen ins Gewicht, daß sie die Verstrammung der Rohmischungen vermindern und die Spannungswerte der Vulkanisate erheblich, ihre Stoßelastizitäten und Shorehärten deutlich heraufsetzen. Dagegen werden die Verarbeitungseigenschaften der Mischung nachteilig beeinflußt, z. B. werden die Anvulkanisationszeiten stark verkürzt. Das bedeutet eine Verminderung der Verarbeitungssicherheit. Ferner werden die Defo-Elastizitäten stark erhöht, was eine Erhöhung des elastischen Kautschukanteils in der Rohmischung bedeutet und eine Erschwerung ihrer Weiterverarbeitung, z. B. beim Spritzen, zur Folge hat.It is known to use organosilicon compounds such as 3-mercaptopropyltrimethoxysilane as adhesion promoters in To use rubber compounds. When using such compounds, it is advantageous that they reduce the tightness of the raw mixes and considerably reduce the tension values of the vulcanizates, increase their impact elasticity and Shore hardness significantly. On the other hand, the processing properties adversely affects the mixture, e.g. B. the scorch times are greatly reduced. That means a reduction in processing security. Furthermore, the defo-elasticities are greatly increased, which is a Increasing the elastic rubber content in the raw mixture means and makes it more difficult Further processing, e.g. B. when spraying, has the consequence.

Gegenstand der Erfindung sind neue Schwefel enthaltende Organosiliciumverbindungen, die für diese Zwecke verwendet werden können, ohne daß die genannten Nachteile in Kauf genommen werden müssen, und ein Verfahren zur Herstellung dieser Verbindungen.The invention relates to new sulfur-containing organosilicon compounds for these Purposes can be used without the disadvantages mentioned being accepted must, and a process for making these compounds.

Sie erbringen einerseits weitgehend die Vorteile zum Beispiel des 3-Mercaptopropyltrimethoxysilans, aber gestalten andererseits die Verarbeitungseigenschaften der Kautschuk-Füllstoff-Mischungen wesentlich günstiger. Ferner sind die erfindungsgemäßen Verbindungen auf Grund ihrer einfachen Herstellungsverfahren mit guten Ausbeuten und der leichten Verfügbarkeit der Ausgangsstoffe in sehr wirtschaftlicher Weise zuganglieh und somit für den technischen Einsatz ausgezeichnet. On the one hand, they largely provide the advantages of 3-mercaptopropyltrimethoxysilane, for example, but on the other hand, make the processing properties of the rubber-filler mixtures much more favorable. Furthermore, the compounds according to the invention are due to their simple production process with good yields and the ready availability of the starting materials in a very economical manner and therefore excellent for technical use.

Die neuen Verbindungen entsprechen den FormelnThe new compounds correspond to the formulas

(H5C,O)3Si-(CH2)3-(S)4-(CH2)3-Si(OC2H5)3 (H 5 C, O) 3 Si- (CH 2) 3- (S) 4 - (CH 2) 3 Si (OC 2 H 5) 3

6565

(H5C2O)3Si-(CH2J2-(S)4-(CHj)2-Si(OC2Hs)3 (H 5 C 2 O) 3 Si- (CH 2 J 2 - (S) 4 - (CHj) 2 -Si (OC 2 Hs) 3

Die erfindungsgemäßen Verbindungen sind wertvolle Haftvermittler, die mit Vorteil in vulkanisierbaren, durch feinteilige natürliche oder synthetische silikatische Füllstoffe verstärkten Kautschukmischungen, die zusätzlich noch Ru3 als Verstärkerfüllstoffe enthalten können, eingesetzt werden.The compounds according to the invention are valuable adhesion promoters which are advantageously used in vulcanizable, rubber compounds reinforced by finely divided natural or synthetic silicate fillers that can additionally contain Ru3 as reinforcing fillers.

Verbindungen der beanspruchten Art sind gelbe, nicht ohne Zersetzung destillierbare Flüssigkeiten.Compounds of the claimed type are yellow liquids which cannot be distilled without decomposition.

Sie können in einfacher und wirtschaftlicher Weise hergestellt werden, wenn man 3-Chlorpropyltnäthoxysilan, 3-Chlorpropyltrimethoxysilan bzw. 2-Chloräthyltriäthoxysilan mit Na2S4 im Molverhältnis 2 :1, vorzugsweise in Gegenwart eines organischen Lösungsmittels, in an sich bekannter Weise umsetzt, von dem gebildeten und abgeschiedenen Halogenid abtrennt und gegebenenfalls das organische Lösungsmittel entfernt.They can be produced in a simple and economical manner if 3-Chlorpropyltnäthoxysilan, 3-Chlorpropyltrimethoxysilan or 2-Chloräthyltriäthoxysilan with Na 2 S 4 in a molar ratio of 2: 1, preferably in the presence of an organic solvent, in a known manner, of the halide formed and deposited is separated off and, if appropriate, the organic solvent is removed.

Die Temperatur, bei der die Umsetzung durchgeführt wird, ist nicht kritisch. Die Umsetzung kann etwa bei Raumtemperatur oder auch bei darunterliegenden Temperaturen erfolgen. Zur Vergrößerung der Reaktionsgeschwindigkeit ist es jedoch im allgemeiner vorteilhaft, bei erhöhten Temperaturen zu arbeiten, die bis zur Siedetemperatur des gegebenenfalls verwendeten Lösungsmittels reichen können. Da die einzusetzenden Ausgangsstoffe flüssig sind, kann die Umsetzung grundsätzlich in Abwesenheit eines Lösungsmittels erfolgen. Vorteilhafter ist jedoch die Anwendung eines inerten organischen Lösungsmittels, das die Verbindung Na2S4 ganz oder teilweise zu lösen vermag. Als solche kommen beispielsweise Dioxan, Tetrahydrofuran, Aceton und Alkohole in Frage.The temperature at which the reaction is carried out is not critical. The reaction can take place at about room temperature or at temperatures below this. In order to increase the rate of the reaction, however, it is generally advantageous to work at elevated temperatures which can reach up to the boiling point of the solvent which is optionally used. Since the starting materials to be used are liquid, the reaction can in principle take place in the absence of a solvent. However, it is more advantageous to use an inert organic solvent which is able to completely or partially dissolve the Na 2 S 4 compound. Examples of these are dioxane, tetrahydrofuran, acetone and alcohols.

Es ist weiter vorteilhaft, die Umsetzung unter Wasserausschluß und/oder unter Luftausschluß durchzuführen. Als Inertgase können dabei Edelgase oder Stickstoff verwendet werden. Beide Maßnahmen bewirken eine Verminderung der Nebenreaktionen.It is also advantageous to carry out the reaction with the exclusion of water and / or with the exclusion of air. Noble gases or nitrogen can be used as inert gases. Both measures cause a reduction in the side reactions.

Bei der Durchführung des erfindungsgemäßen Verfahrens geht man zweckmäßigerweise so vor, daß man die Verbindung Na2S4 zunächst ganz oder teilweise in einem inerten organischen Lösungsmittel löst. Hierbei sollte das Lösungsmittel so ausgewählt sein, daß unerwünschte Umesterungen am Siliciumatom ausgeschlossen sind. Zu dieser Lösung wird dann 3-Chlorpropyltriäthoxysilan oder 3-Chlorpropyltrimethoxysilan oder 2-Chloräthyltriäthoxysilan, gegebenenfalls ebenfalls gelöst, zugegeben. Nach beendeter Umsetzung wird von dem abgeschiedenen Salz (Metallhalogenid) abfiltriert und das organische Lösungsmittel, gegebenenfalls unter vermindertem Druck, destillativ entfernt. Die Endprodukte selbst können nicht ohne Zersetzung destilliert werden. Sie bleiben im Destillationssumpf zurück. Sie können ohne Reinigung direkt verwendet werden.When carrying out the process according to the invention, it is expedient to proceed in such a way that the compound Na 2 S 4 is first completely or partially dissolved in an inert organic solvent. The solvent should be selected so that undesired transesterification on the silicon atom is excluded. 3-Chloropropyltriethoxysilane or 3-chloropropyltrimethoxysilane or 2-chloroethyltriethoxysilane, optionally also dissolved, is then added to this solution. After the reaction has ended, the precipitated salt (metal halide) is filtered off and the organic solvent is removed by distillation, if appropriate under reduced pressure. The end products themselves cannot be distilled without decomposition. They remain in the distillation sump. They can be used directly without cleaning.

Beispiel 1example 1

In eine siedende Lösung von 0,5 Mol Na2S4 in 500 ml wasserfreiem Äthanol wurde nach und nach 1 Mol 3-Chlorpropyltriäthoxysilan eingetragen. Nach beendeter Reaktion wurde vom abgeschiedenen Salz abfiltriert und das Filtrat im Vakuum vom Lösungsmittel befreit. Es wurden 263 g (95,8% der Theorie) der Verbindung1 mol of 3-chloropropyltriethoxysilane was gradually added to a boiling solution of 0.5 mol of Na 2 S 4 in 500 ml of anhydrous ethanol. When the reaction had ended, the precipitated salt was filtered off and the filtrate was freed from the solvent in vacuo. There were 263 g (95.8% of theory) of the compound

(H5C2O)3Si-(CH2)J-(S)4-(CH2)J-Si(OCjHs),(H 5 C 2 O) 3 Si- (CH 2 ) J- (S) 4 - (CH 2 ) J-Si (OCjHs),

erhalten.obtain.

Analysenvv^rte:Analysis methods:

Berechnet C 40,11, H 7,84, Si 10,42 S 23,79; gefunden C 40,0, H 7,78, Si 10,48, S 22,98.Calculated C 40.11, H 7.84, Si 10.42, S 23.79; Found C 40.0, H 7.78, Si 10.48, S 22.98.

Beispiel 2Example 2

In eine siedende Lösung von 2 Mol Na2S4 in 2000 ml wasserfreiem Methanol wurden nach und nach 4 Mol 3-Chlorpropyltrimethoxysilan eingetragen. Nach beendeter Reaktion wurde vom abgeschiedenen Salz abfiltriert und das Lösungsmittel im Vakuum entfernt Es wurden 859 g (94,1 °/o der Theorie) der Verbindung4 mol of 3-chloropropyltrimethoxysilane were gradually introduced into a boiling solution of 2 mol of Na 2 S 4 in 2000 ml of anhydrous methanol. When the reaction had ended, the precipitated salt was filtered off and the solvent was removed in vacuo. 859 g (94.1% of theory) of the compound were obtained

gefunden C 31,20, H 6,43, Si 12,40, S 27,35. Beispiel 3Found C 31.20, H 6.43, Si 12.40, S 27.35. Example 3

In eine auf 500C erhitzte Lösung von 0,5 Mol Na2S4 in 500 ml wasserfreiem Äthanol wurde nach und nach 1 Mol 2-Chloräthyltriäthoxysilan zugegeben. Nach beendeter Reaktion wurde vom abgeschiedenen Salz abfiltriert und das Filtrat im Vakuum vom Lösungsmittel befreit Es wurden 226,5 g (88,7% der Theorie) der Verbindung1 mol of 2-chloroethyltriethoxysilane was gradually added to a solution, heated to 50 ° C., of 0.5 mol of Na 2 S 4 in 500 ml of anhydrous ethanol. When the reaction had ended, the deposited salt was filtered off and the filtrate was freed from the solvent in vacuo. 226.5 g (88.7% of theory) of the compound were obtained

erhalten.obtain.

Analysenwerte:Analysis values:

Berechnet C 31,69, H 6,65, Si 12,35, S 28,20; erhalten.Calculated C 31.69, H 6.65, Si 12.35, S 28.20; obtain.

Analysenwerte:Analysis values:

Berechnet C 37,61, H 7,49, Si 10,99, S 25,10; gefunden C 37,12, H 7,32, Si 11,21, S 24,38.Calculated C 37.61, H 7.49, Si 10.99, S 25.10; Found C 37.12, H 7.32, Si 11.21, S 24.38.

Claims (1)

Patentansprüche:Patent claims: 1. Schwefel enthaltende Organosiliciumverbindungen der Formeln1. Sulfur-containing organosilicon compounds of the formulas (H3C O)3Si-(C H2)J-(S)4-(C Hj)3-Si(O C H3)j (H5C2O)3Si-(CHj)2-(S)4-(CHj)2-Si(OC2H5)J(H 3 CO) 3 Si- (CH 2 ) J- (S) 4 - (C Hj) 3 -Si (OCH 3 ) j (H 5 C 2 O) 3 Si- (CHj) 2 - (S) 4 - (CHj) 2 -Si (OC 2 H 5 ) J mitwith
DE19712141159 1971-08-17 1971-08-17 Organosilicon compounds containing sulfur Expired DE2141159C3 (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
BE787691D BE787691A (en) 1971-08-17 ORGANOSILICIC COMPOUNDS CONTAINING SULFUR
DE19712141159 DE2141159C3 (en) 1971-08-17 1971-08-17 Organosilicon compounds containing sulfur
SU1791182A SU511863A3 (en) 1971-08-17 1972-05-30 The method of obtaining silicone polysulfides
FR7219496A FR2149339B1 (en) 1971-08-17 1972-05-31
DD163594A DD99585A5 (en) 1971-08-17 1972-06-09
ES403883A ES403883A1 (en) 1971-08-17 1972-06-15 Sulfur containing organosilicon compounds
NL7209035A NL151995B (en) 1971-08-17 1972-06-29 PROCESS FOR PREPARING SULFUR-CONTAINING ORGANOSILICON COMPOUNDS.
US00277043A US3842111A (en) 1971-08-17 1972-08-01 Sulfur containing organosilicon compounds
CS568972A CS188151B2 (en) 1971-08-17 1972-08-16 Method of organo silicon compounds containing sulphur
IT52209/72A IT962125B (en) 1971-08-17 1972-08-16 SULFURED ORGANIC SILICON COMPOUNDS AND PROCEDURE FOR THEIR PRODUCTION
BR5584/72A BR7205584A (en) 1971-08-17 1972-08-16 PROCESS FOR OBTAINING SULFUR ORGANOSILIC COMPOUNDS
JP47082444A JPS5128623B2 (en) 1971-08-17 1972-08-17
AT710372A AT315874B (en) 1971-08-17 1972-08-17 Process for the production of new, sulfur-containing organosilicon compounds
GB3838672A GB1394135A (en) 1971-08-17 1972-08-17 Sulphurcontaining organo-silicon compounds
US415176A US3873489A (en) 1971-08-17 1973-11-12 Rubber compositions containing silica and an organosilane
US05/467,583 US3978103A (en) 1971-08-17 1974-05-06 Sulfur containing organosilicon compounds
US05/529,568 US3997356A (en) 1971-08-17 1974-12-04 Reinforcing additive
US05/690,150 US4076550A (en) 1971-08-17 1976-05-26 Reinforcing additive

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19712141159 DE2141159C3 (en) 1971-08-17 1971-08-17 Organosilicon compounds containing sulfur

Publications (3)

Publication Number Publication Date
DE2141159A1 DE2141159A1 (en) 1973-03-01
DE2141159B2 DE2141159B2 (en) 1974-11-28
DE2141159C3 true DE2141159C3 (en) 1983-11-24

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DE19712141159 Expired DE2141159C3 (en) 1971-08-17 1971-08-17 Organosilicon compounds containing sulfur

Country Status (3)

Country Link
CS (1) CS188151B2 (en)
DE (1) DE2141159C3 (en)
SU (1) SU511863A3 (en)

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DE19734295C1 (en) * 1997-08-08 1999-02-25 Degussa Process for the production of high purity organosilicon disulfanes
US6066752A (en) * 1998-04-10 2000-05-23 Daiso Co., Ltd. Process for producing sulfur-containing organosilicon compounds and synthetic intermediates thereof
DE102005037690A1 (en) * 2005-08-10 2007-02-15 Degussa Ag Preparation of organosilicon compound comprises reacting halogenalkoxysilane compound with a dry polysulfide, dry sulfide and optionally sulfur; removing the mixture from the organic solvent and separating the binding phase
US7687558B2 (en) 2006-12-28 2010-03-30 Momentive Performance Materials Inc. Silated cyclic core polysulfides, their preparation and use in filled elastomer compositions
US7696269B2 (en) 2006-12-28 2010-04-13 Momentive Performance Materials Inc. Silated core polysulfides, their preparation and use in filled elastomer compositions
US7737202B2 (en) 2006-12-28 2010-06-15 Momentive Performance Materials Inc. Free-flowing filler composition and rubber composition containing same
US7781606B2 (en) 2006-12-28 2010-08-24 Momentive Performance Materials Inc. Blocked mercaptosilane coupling agents, process for making and uses in rubber
US7960460B2 (en) 2006-12-28 2011-06-14 Momentive Performance Materials, Inc. Free-flowing filler composition and rubber composition containing same
US7968635B2 (en) 2006-12-28 2011-06-28 Continental Ag Tire compositions and components containing free-flowing filler compositions
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
US7968636B2 (en) 2006-12-28 2011-06-28 Continental Ag Tire compositions and components containing silated cyclic core polysulfides
US8592506B2 (en) 2006-12-28 2013-11-26 Continental Ag Tire compositions and components containing blocked mercaptosilane coupling agent

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US4044037A (en) * 1974-12-24 1977-08-23 Union Carbide Corporation Sulfur containing silane coupling agents
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DE3311340A1 (en) * 1983-03-29 1984-10-11 Degussa Ag, 6000 Frankfurt METHOD FOR PRODUCING SULFURIZED ORGANOSILICIUM COMPOUNDS
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DE19818552A1 (en) * 1998-04-24 1999-10-28 Bayer Ag Mixtures of rubbers and activated and hydrophobicized exidic and silicate fillers and a process for their production
DE19825796A1 (en) * 1998-06-10 1999-12-16 Degussa New oligomeric organosilane polysulfanes, their use in rubber mixtures and for the production of moldings
DE19832458A1 (en) * 1998-07-18 2000-01-27 Bayer Ag Rubber mixture, useful of the production of tire treads
DE19844607A1 (en) * 1998-09-29 2000-03-30 Degussa Sulfanylsilanes
DE19905820A1 (en) 1998-10-27 2000-05-04 Degussa Sulfur-functional polyorganosilanes
DE19915281A1 (en) * 1999-04-03 2000-10-05 Degussa Rubber compounds
EP1063259A1 (en) * 1999-06-26 2000-12-27 Bayer Ag Rubber compositions containing rubber microgels and sulfur-bearing organosilicon compounds
DE19950608A1 (en) * 1999-10-21 2001-05-03 Degussa Organosilicon compound, process for its preparation and its use
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DE2141159A1 (en) 1973-03-01

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