EP3387060A1 - Kautschukmischungen - Google Patents

Kautschukmischungen

Info

Publication number
EP3387060A1
EP3387060A1 EP16802056.8A EP16802056A EP3387060A1 EP 3387060 A1 EP3387060 A1 EP 3387060A1 EP 16802056 A EP16802056 A EP 16802056A EP 3387060 A1 EP3387060 A1 EP 3387060A1
Authority
EP
European Patent Office
Prior art keywords
rubber
general formula
silatran
mixtures according
aromatic
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.)
Withdrawn
Application number
EP16802056.8A
Other languages
German (de)
English (en)
French (fr)
Inventor
Caren RÖBEN
Sascha Erhardt
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
Evonik 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
Application filed by Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP3387060A1 publication Critical patent/EP3387060A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/549—Silicon-containing compounds containing silicon in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers

Definitions

  • the present invention relates to rubber mixtures, a process for their preparation and their use.
  • EP 2 206 742 discloses silatran-containing particles which are used as coupling agents between silica and rubber.
  • silane derivatives of the formula R “'Si (0-CR' R” -CR 'R') 3 N, where at least one R "is an alkenyloxyalkyl group. These silane derivatives can in
  • Silicone compounds are used.
  • EP 1 045 006, EP 1 045 002 and EP 0 919 558 disclose silatranes for
  • Silicone rubber applications are known.
  • diphenylguanidine as a secondary accelerator in silica-filled rubber blends is known from various references (for example, H.-D.
  • the object of the invention is to prepare rubber mixtures with accelerators which release no toxic aniline or its derivatives.
  • the invention relates to rubber mixtures which are characterized in that they comprise at least one rubber, with the exception of silicone rubber, and at least one silatran of the general formula (I),
  • X 1 , X 2 and X 3 are each independently hydrogen (-H), straight-chain unsubstituted or branched unsubstituted (C 1 -C 10) -alkyl, preferably straight-chain unsubstituted or branched unsubstituted (C 1 -C 6) -alkyl, particularly preferably methyl or Ethyl, mean.
  • the rubber may preferably be a diene rubber.
  • G may preferably be CH3CH2CH2-.
  • X 1 , X 2 and X 3 may preferably be H.
  • the silatran of the general formula (I) can be CH 3 CH 2 CH 2 -Si (-O-CH 2 -CH 2 -) 3N.
  • Silatrans of the general formula (I) may be mixtures of silatrans of the general formula (I).
  • Silatrans of the general formula (I) may contain partially hydrolyzed silatrane compounds of the general formula (I).
  • Silatrans of the general formula (I) can be: CH 3 -CH 2 -si (-O-CH 2 -CH 2 -) 3 N,
  • the silatrans of the formula (I) can be prepared by reacting at least one compound of the general formula (I)
  • the reaction can be catalyzed or uncatalyzed.
  • the alk-OH can from the
  • Reaction mixture are separated continuously or discontinuously.
  • Examples of compounds of the general formula III may be: triethanolamine,
  • a low water content of the compounds of the formula III used can have a favorable effect on the composition and the product properties of the compounds.
  • the compounds of the formula III may preferably have a water content of less than 1% by weight, particularly preferably less than 0.2% by weight.
  • the reaction can be carried out in typical organic solvents having a boiling point of less than 200 ° C., preferably less than 100 ° C.
  • the reaction can be carried out in the absence of organic solvents.
  • metal-free or metal-containing catalysts can be used as a catalyst in the process for the preparation of silatrans of the formula (I).
  • metal-containing catalysts metal compounds of the 3.-7. Group, the 13.-14. Group and / or the Lanthaniden join be used.
  • transition metal compounds can be used as metal-containing catalysts.
  • the metal-containing catalysts may be metal compounds such as metal chlorides, metal oxides, metal oxychlorides, metal sulfides, metal sulfochlorides, metal alcoholates, metal thiolates, metal oxyalcoholates, metal amides, metal imides, or multiple bonded ligand transition metal compounds.
  • titanium alkoxides can be used as metal-containing catalysts.
  • titanates such as, for example, tetra-n-butyl orthotitanate, tetraethyl orthotitanate, tetra-n-propyl orthotitanate or tetraisopropyl orthotitanate, can be used as catalysts.
  • organic acids can be used as metal-free catalysts.
  • suitable organic acids are trifluoroacetic acid, trifluoromethanesulfonic acid or p-toluenesulfonic acid, trialkylammonium compounds R 3 NH + X " or organic bases such as, for example, trialkylamines NR 3.
  • the preparation process can be carried out at atmospheric pressure or reduced pressure, preferably between 1 and 600 mbar, more preferably between 5 and 200 mbar.
  • the production process can be carried out in the temperature range between 20 ° C and 200 ° C, preferably between 35 ° C and 150 ° C.
  • the reaction mixture may be added before or during the reaction substances that promote the transport of water from the product by forming azeotropic mixtures.
  • the corresponding substances can be cyclic or straight-chain aliphatics, aromatics, mixed aromatic-aliphatic compounds, ethers, alcohols or acids.
  • hexane, cyclohexane, benzene, toluene, ethanol, propanol, iso-propanol, butanol, ethylene glycol, tetrahydrofuran, dioxane, formic acid, acetic acid, ethyl acetate or Dimetyhlformamid can be used.
  • the silatranes of formula (I) can be used as accelerators in filled rubber compounds, for example tire treads.
  • the silatrans of the general formula (I) can be used in amounts of 0.1 to 8 parts by weight, preferably 0.2 to 6 parts by weight, more preferably 0.8 to 4 parts by weight, based on 100 wt. - Parts of the rubber used to be used.
  • Another object of the invention is a process for the preparation of the rubber mixtures according to the invention, which is characterized in that at least one rubber and a silatrane of the formula (I) is mixed.
  • the rubber mixture may contain at least one filler.
  • the addition of the silatrans of the general formula (I), as well as the addition of the fillers can be carried out at melt temperatures of 100 to 200 ° C. However, it can also be carried out at lower temperatures of 40 to 100 ° C, for example together with other rubber auxiliaries.
  • the silatranes of the formula (I) can be added to the mixing process both in pure form and supported on an inert organic or inorganic carrier, as well as pre-reacted with an organic or inorganic carrier.
  • Preferred support materials may be precipitated or pyrogenic silicas, waxes, thermoplastics, natural or synthetic silicates, natural or synthetic oxides, preferably alumina, or carbon blacks.
  • silatrans can also be pre-reacted with the filler to be used
  • fillers the following fillers can be used for the rubber mixtures according to the invention:
  • Carbon black The carbon blacks to be used in this case can be prepared by the flame black, furnace, gas black or thermal black process.
  • the carbon blacks may have a BET surface area of 20 to 200 m 2 / g.
  • the carbon blacks may also be doped, such as with Si.
  • Amorphous silicas preferably precipitated silicas or fumed silicas.
  • the amorphous silicas may have a specific surface area of 5 to 1000 m 2 / g, preferably 20 to 400 m 2 / g (BET surface area) and a primary particle size of 10 to 400 nm. If appropriate, the silicas may also be used as mixed oxides with others
  • Metal oxides such as Al, Mg, Ca, Ba, Zn and titanium oxides are present.
  • Synthetic silicates such as aluminum silicate or alkaline earth silicates, for example
  • Magnesium silicate or calcium silicate The synthetic silicates with BET surface areas of 20 to 400 m 2 / g and primary particle diameters of 10 to 400 nm. - Synthetic or natural aluminas and hydroxides.
  • Natural silicates such as kaolin and other naturally occurring silicas.
  • Glass fiber and glass fiber products (mats, strands) or glass microspheres.
  • amorphous silicas particularly preferably precipitated silicas or silicates, particularly preferably precipitated silicas having a BET surface area of from 20 to 400 m 2 / g in amounts of from 5 to 180 parts by weight, based in each case on 100 parts of rubber.
  • the fillers mentioned can be used alone or in a mixture.
  • 10 to 180 parts by weight of fillers, preferably precipitated silica, optionally together with 0 to 100 parts by weight of carbon black, and 0, 1 to 8 parts by weight of silatrans of the general formula I, respectively based on 100 parts by weight of rubber be used for the preparation of the mixtures.
  • Natural rubber also synthetic rubbers.
  • Preferred synthetic rubbers are described, for example, in W. Hofmann, Kautschuktechnologie, Genter Verlag, Stuttgart 1980. They include, among others, polybutadiene (BR),
  • Styrene / butadiene copolymers for example emulsion SBR (E-SBR) or solution SBR (L-SBR), preferably with a styrene content of 1 to 60 wt .-%, particularly preferably 2 to 50 wt .-%, based on the total polymer, - chloroprene (CR),
  • E-SBR emulsion SBR
  • L-SBR solution SBR
  • styrene content 1 to 60 wt .-%, particularly preferably 2 to 50 wt .-%, based on the total polymer, - chloroprene (CR)
  • Butadiene / acrylonitrile copolymers preferably having an acrylonitrile content of 5 to 60% by weight, preferably 10 to 50% by weight, based on the total polymer (NBR), partially hydrogenated or fully hydrogenated NBR rubber (HNBR), ethylene / Propylene / diene copolymers (EPDM) or rubbers mentioned above, which additionally have functional groups, such as Carboxy, silanol or epoxy groups, for example epoxidized NR, carboxy-functionalized NBR or silanol (-SiOH) or siloxy-functionalized (-Si-OR), amino-epoxy, mercapto, hydroxy-functionalized SBR, and mixtures these rubbers.
  • NBR total polymer
  • HNBR partially hydrogenated or fully hydrogenated NBR rubber
  • EPDM ethylene / Propylene / diene copolymers
  • functional groups such as Carboxy, silanol or epoxy groups, for example epoxidized NR, carboxy-functional
  • the rubber vulcanizates of the invention may comprise further rubber auxiliaries, such as reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers,
  • the rubber auxiliaries may be present in known amounts, inter alia, after the
  • Usual amounts may be, for example, amounts of 0, 1 to 50 wt .-%, based on rubber.
  • crosslinkers peroxides, sulfur or sulfur-donating substances can be used.
  • Rubber compounds may also contain vulcanization accelerators.
  • suitable vulcanization accelerators may be mercaptobenzothiazoles, sulfenamides, thiurams, dithiocarbamates, thioureas and thiocarbonates.
  • the vulcanization accelerators and sulfur can be used in amounts of 0.1 to 10 wt .-%, preferably 0, 1 to 5 wt .-%, based on 100 parts by weight of rubber.
  • the vulcanization of the rubber mixtures according to the invention can be carried out at temperatures of 100 to 200 ° C, preferably 120 to 180 ° C, optionally under pressure of 10 to 200 bar.
  • the blending of the rubbers with the filler, optionally rubber auxiliaries and the silatrane can be carried out in known mixing units, such as rollers, internal mixers and mixing extruders.
  • the rubber mixtures according to the invention can be used for the production of moldings, for example for the production of pneumatic tires, tire treads, cable sheaths, hoses,
  • Driving belts conveyor belts, roller coverings, tires, shoe soles, sealing rings and
  • the rubber mixtures according to the invention can be carried out without the addition of guanidines.
  • the rubber mixture may be free from
  • Guanidine derivatives preferably diphenylguanidine.
  • silatrans of the general formula (I) can be used as a secondary accelerator.
  • guanidine accelerator can be omitted partially or completely.
  • Another object of the invention is the use of silatrans of the general formula (i),
  • G is a monovalent unbranched or branched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic / aromatic (C2-Cs) -, preferably (C2-C6) -, particularly preferably (C3-C6) -, very particularly preferably (C3) -, hydrocarbon chain is,
  • X 1 , X 2 and X 3 are each independently hydrogen (-H), straight-chain unsubstituted or branched unsubstituted (C 1 -C 10) -alkyl, preferably straight-chain unsubstituted or branched unsubstituted (C 1 -C 6) -alkyl, particularly preferably methyl or Ethyl, mean, in
  • triethanolamine from BASF SE isobutyltriethoxysilane, hexadecyltrimethoxysilane, octyltriethoxysilane and propyltriethoxysilane from Evonik Industries AG, sodium hydroxide and phenyltrimethoxysilane from Sigma-Aldrich, ethanol and methanol from Sasol Solvents Germany GmbH, trimethoxymethylsilane from the company Merck, as well as n-hexane and n-pentane from VWR.
  • the product has a melting point of 85 ° C and according to analysis by H-NMR
  • the product has a melting point of 69 ° C and according to H-NMR analysis contains 98.4 wt .-% 1-Octylsilatran.
  • the product has a melting point of 79 ° C and contains according to H-NMR analysis 99.8 wt .-% 1-Hexadecylsilatran.
  • the product has a melting point of 55 ° C and according to H-NMR analysis contains 96.0 wt .-% of 1-isobutylsilatran.
  • the product has a melting point of 205 ° C and according to H-NMR analysis contains 94.4 wt .-% 1-phenylsilatran.
  • Example 5 Rubber Engineering Studies
  • the recipe used for the rubber compounds is given in Table 1 below.
  • the unit phr means by weight, based on 100 parts of the used
  • mixture 2 mixture without secondary accelerator.
  • inventive mixture 4 Silatran according to Example 1.
  • mixture 5 according to the invention Silatran according to Example 2.
  • inventive mixture 8 Silatran according to Example 4.
  • Vulkanox ® HS / LG k 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5 1, 5
  • Si 266 ® Bis (triethoxysilylpropyl) from Evonik Industries AG disulfide.
  • Corax® N 330 carbon black from Orion Engineered Carbons GmbH.
  • ZnO zinc oxide ZnO RS RAL 844 C from Arnsperger Chemikalien GmbH.
  • Perkacit TBzTD Tetrabenzylthiuram disulfide (TBzTD) based on Weber & Schaer (manufacturer: Dalian Richon).
  • Vulkacit ® CZ / EG-C A / Rhein Chemie Rheinau GmbH cyclohexyl-2-benzothiazole.
  • Sulfur Milling sulfur 80/90 ° from Solvay & CPC Barium Strontium GmbH & Co. KG. The mixtures are prepared in three stages in a 1.5 L internal mixer (E type) at a batch temperature of 155 ° C. according to the mixing instructions described in Table 2.
  • the vulcanization takes place at a temperature of 165 ° C in a typical
  • Vulcanization press with a holding pressure of 120 bar after t.95%.
  • the t.95% time is determined by means of Moving The Rheometer (rotorless Vulkameter) according to ISO 6502 (paragraph 3.2 "rotorless curemeter”) at 165 ° C.
  • the rubber test is carried out according to the test methods given in Table 3.
  • Table 4 gives the rubber technical data for the raw mixtures and vulcanizates.
  • Standard secondary accelerator DPG contains and compared to the comparison mixture 3.
  • the comparative mixture 6 however, has weaknesses in the abrasion (DIN abrasion) compared to the mixtures according to the invention 4, 5, 7 and 8.
  • Comparative blends Benefits in wet adhesion (ball rebound at 23 ° C) compared to the comparative blends 1, 2, 3 and 6 on.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Tires In General (AREA)
EP16802056.8A 2015-12-07 2016-11-28 Kautschukmischungen Withdrawn EP3387060A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015224436.9A DE102015224436A1 (de) 2015-12-07 2015-12-07 Kautschukmischungen
PCT/EP2016/079023 WO2017097625A1 (de) 2015-12-07 2016-11-28 Kautschukmischungen

Publications (1)

Publication Number Publication Date
EP3387060A1 true EP3387060A1 (de) 2018-10-17

Family

ID=57421852

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16802056.8A Withdrawn EP3387060A1 (de) 2015-12-07 2016-11-28 Kautschukmischungen

Country Status (15)

Country Link
US (1) US10781302B2 (ja)
EP (1) EP3387060A1 (ja)
JP (1) JP6828051B2 (ja)
KR (1) KR20180090279A (ja)
CN (1) CN108291054B (ja)
BR (1) BR112018011508B1 (ja)
CA (1) CA3007487C (ja)
DE (1) DE102015224436A1 (ja)
IL (1) IL259779B (ja)
MX (1) MX2018006672A (ja)
MY (1) MY187475A (ja)
RU (1) RU2736124C2 (ja)
UA (1) UA124194C2 (ja)
WO (1) WO2017097625A1 (ja)
ZA (1) ZA201804383B (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102024758B1 (ko) * 2018-05-26 2019-09-25 에스케이이노베이션 주식회사 식각액 조성물, 절연막의 식각방법, 반도체 소자의 제조방법 및 실란화합물
CN116875064B (zh) * 2023-07-25 2023-12-19 广州市佳合硅橡胶有限公司 一种耐高温混炼硅橡胶及其制备方法

Family Cites Families (14)

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SU514841A1 (ru) * 1974-07-09 1976-05-25 Иркутский Институт Органической Химии Сибирского Отделения Ссср Способ получени бис(силатранилалкил) сульфидов
US4048206A (en) 1975-04-22 1977-09-13 Mikhail Grigorievich Voronkov Process for the production of 1-organylsilatranes and carbofunctional derivatives thereof
US5945555A (en) 1997-11-28 1999-08-31 Dow Corning Toray Silicone Co., Ltd. Silatrane derivative, method for manufacturing same, adhesion promoter, and curable silicone composition
JP2000265063A (ja) 1999-03-16 2000-09-26 Dow Corning Toray Silicone Co Ltd シリコーンゴム組成物
JP2000302977A (ja) 1999-04-16 2000-10-31 Dow Corning Toray Silicone Co Ltd シリコーンゴム組成物
US6284861B1 (en) * 1999-12-13 2001-09-04 Dow Corning Toray Silicone, Ltd. Silicone rubber composition
DE102005038794A1 (de) * 2005-08-17 2007-02-22 Degussa Ag Kautschukmischungen
DE102006004062A1 (de) * 2006-01-28 2007-08-09 Degussa Gmbh Kautschukmischungen
JP5193470B2 (ja) * 2007-01-12 2013-05-08 東レ・ダウコーニング株式会社 ビス（シラトラニルアルキル）ポリスルフィド等の製造方法およびビス（シラトラニルアルキル）ポリスルフィド等の混合物
DE102008054967A1 (de) 2008-12-19 2010-06-24 Evonik Degussa Gmbh Silatranhaltige Partikel
US9109103B2 (en) * 2013-11-25 2015-08-18 The Goodyear Tire & Rubber Company Functionalized polymer, rubber composition and pneumatic tire
US9109073B1 (en) * 2014-08-19 2015-08-18 The Goodyear Tire & Rubber Company Bifunctionalized polymer
US9090730B1 (en) * 2014-08-19 2015-07-28 The Goodyear Tire & Rubber Company Rubber composition and pneumatic tire
US9428628B2 (en) * 2014-08-20 2016-08-30 The Goodyear Tire & Rubber Company Functionalized polymer, rubber composition and pneumatic tire

Also Published As

Publication number Publication date
WO2017097625A1 (de) 2017-06-15
KR20180090279A (ko) 2018-08-10
MY187475A (en) 2021-09-23
MX2018006672A (es) 2018-11-09
CA3007487C (en) 2022-10-04
BR112018011508A2 (pt) 2018-12-04
CN108291054B (zh) 2020-12-22
IL259779A (en) 2018-07-31
ZA201804383B (en) 2019-04-24
RU2018123802A3 (ja) 2020-04-28
JP2018538427A (ja) 2018-12-27
UA124194C2 (uk) 2021-08-04
DE102015224436A1 (de) 2017-06-08
CA3007487A1 (en) 2017-06-15
RU2018123802A (ru) 2020-01-09
US20180346696A1 (en) 2018-12-06
CN108291054A (zh) 2018-07-17
JP6828051B2 (ja) 2021-02-10
IL259779B (en) 2022-04-01
BR112018011508B1 (pt) 2022-05-17
RU2736124C2 (ru) 2020-11-11
US10781302B2 (en) 2020-09-22

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