JP5357390B2 - ポリマー−充填剤カップリング剤 - Google Patents
ポリマー−充填剤カップリング剤 Download PDFInfo
- Publication number
- JP5357390B2 JP5357390B2 JP2006356224A JP2006356224A JP5357390B2 JP 5357390 B2 JP5357390 B2 JP 5357390B2 JP 2006356224 A JP2006356224 A JP 2006356224A JP 2006356224 A JP2006356224 A JP 2006356224A JP 5357390 B2 JP5357390 B2 JP 5357390B2
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- JP
- Japan
- Prior art keywords
- polymer
- filler
- compound
- sulfur
- rubber
- Prior art date
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- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
[式中、R8は、分岐鎖若しくは直鎖状のC1−C20アルキル基、分岐鎖若しくは直鎖状のC3−C20シクロアルキル基、分岐鎖若しくは直鎖状のC6−C20アリール基、分岐鎖若しくは直鎖状のC7−C20アルキルアリール基、又はそれらが混じった状態である]を含むことができる。該アリルスズ部分の−CH部分は、B−A−Sx−N化合物のA基に結合して、(アリルスズ)−A−Sx−Nを形成する。
[式中、A'及びA"は、分岐鎖若しくは直鎖状のC1−C20アルキレニル部分、分岐鎖若しくは直鎖状のC3−C20シクロアルキレニル部分、分岐鎖若しくは直鎖状のC6−C20アリーレニル部分、又は分岐鎖若しくは直鎖状のC7−C20アルキルアリーレニル部分であり;Zは、酸素、硫黄又はC=Oであり;kは、1から約4である]を含み得る。例えば、Aは、B及びSxとのオルト、メタ又はパラ結合を有するフェニル基を含み得る。他の例としては、Aは、(CH2)m
[式中、mは、1から約10である]を含み得る。
ビス-[2-(2-オキサゾリル)-フェニル]-ジスルフィド(2OPD)の合成
20gの2,2'-ジチオ-ビス-(安息香酸)(65mmol)を28.6mLのチオニルクロライド(390mmol)に加えた混合物を12時間還流し、その後、濾過した。ロータリーエバポレーターを用いて、濾液を乾燥し、150gの2,2'-ジチオ-ビス-(ベンゾイルクロライド)の粉末(44mmol)を回収した。この反応の収率は、68%であった。
ゴムのヒステリシス特性への2OPDの効果を判断するために、溶液重合SBR、カーボンブラック及び他の典型的な配合成分を含む4種のゴム配合組成物を調製した。表1に示すように、コントロール組成物(C1)、2種の2OPD含有組成物(E1及びE2)、並びに天然ゴムにおけるヒステリシスを減少させることが知られている市販の添加剤(Sumifine(登録商標)1162、住友化学社から入手可能)を含有する比較組成物(C2)を調製した。
Claims (4)
- 分子構造内に不飽和炭素−炭素結合を有するポリマーと、
式:B−A−Sx−N
[式中、Bは、アザへテロ環式の酸素若しくは硫黄含有部分であり;
Sxは、ポリスルフィドであって、但し、xが2から10の間であり;
Aは、BとSxの間に橋かけを形成する連結基であって、分岐鎖若しくは直鎖状のC6−C20アリーレニル部分、又は分岐鎖若しくは直鎖状のC7−C20アルキルアリーレニル部分であり;
Nは、A−Bであり;
前記アザへテロ環式の酸素若しくは硫黄含有部分が下記式II:
[式中、Xは、酸素又は硫黄であって;R 2、R3、R4、及びR 5 は、それぞれ独立して水素、分岐鎖又は直鎖状のC1−C20アルキル基であり、R 1 はAである]である]
で表わされる化合物とを含む組成物。 - 前記化合物が、ビス-[2-(2-オキサゾリニル)-フェニル]-ジスルフィドであることを特徴とする請求項1に記載の組成物。
- 請求項1に記載の組成物を含む空気入りタイヤ。
- ポリマー組成物中への充填剤の分散を促進する方法であって、
(i)分子構造中に不飽和炭素−炭素結合を有するポリマー;(ii)式:B−A−Sx−N[式中、Bは、アザへテロ環式の酸素若しくは硫黄含有部分であり;Sxは、ポリスルフィドを含み、xが2から10であり;Aは、BとSxの間に橋かけを形成する連結基であって、分岐鎖若しくは直鎖状のC6−C20アリーレニル部分、又は分岐鎖若しくは直鎖状のC7−C20アルキルアリーレニル部分であり;Nは、A−Bであり;前記アザへテロ環式の酸素若しくは硫黄含有部分が下記式II:
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US75453305P | 2005-12-28 | 2005-12-28 | |
US60/754,533 | 2005-12-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007238600A JP2007238600A (ja) | 2007-09-20 |
JP5357390B2 true JP5357390B2 (ja) | 2013-12-04 |
Family
ID=37963975
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006356224A Expired - Fee Related JP5357390B2 (ja) | 2005-12-28 | 2006-12-28 | ポリマー−充填剤カップリング剤 |
Country Status (4)
Country | Link |
---|---|
US (2) | US8080605B2 (ja) |
EP (1) | EP1803713B1 (ja) |
JP (1) | JP5357390B2 (ja) |
ES (1) | ES2491216T3 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013191764A1 (en) * | 2012-06-21 | 2013-12-27 | Sid Richardson Carbon, Ltd. | Polysulfide treatment of carbon black filler and elastomeric compositions with polysulfide treated carbon black |
CN113166494B (zh) * | 2018-12-11 | 2023-08-11 | 倍耐力轮胎股份公司 | 轮胎和含交联酚醛树脂的用于轮胎的弹性体胶料 |
Family Cites Families (38)
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US2968640A (en) * | 1959-01-19 | 1961-01-17 | Goodrich Co B F | Composition comprising styrene-butadiene elastomer, carbon black, an aminothiazole disulfide and a cadmium compound and method for curing same |
US4130562A (en) * | 1975-01-10 | 1978-12-19 | Givaudan Corporation | Odorant or flavoring thiazolyl disulphides |
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US4843087A (en) * | 1983-08-29 | 1989-06-27 | Sterling Drug Inc. | Di-heterocyclic compounds and their use as antiviral agents |
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-
2006
- 2006-12-28 EP EP06256596.5A patent/EP1803713B1/en not_active Expired - Fee Related
- 2006-12-28 ES ES06256596.5T patent/ES2491216T3/es active Active
- 2006-12-28 US US11/617,210 patent/US8080605B2/en not_active Expired - Fee Related
- 2006-12-28 JP JP2006356224A patent/JP5357390B2/ja not_active Expired - Fee Related
-
2011
- 2011-11-11 US US13/294,761 patent/US8765859B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US8765859B2 (en) | 2014-07-01 |
US8080605B2 (en) | 2011-12-20 |
ES2491216T3 (es) | 2014-09-05 |
US20070161756A1 (en) | 2007-07-12 |
EP1803713B1 (en) | 2014-06-04 |
EP1803713A2 (en) | 2007-07-04 |
US20120083562A1 (en) | 2012-04-05 |
JP2007238600A (ja) | 2007-09-20 |
EP1803713A3 (en) | 2011-05-04 |
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