JP6560607B2 - ゴム用添加剤、ゴム組成物およびそれを用いた空気入りタイヤ - Google Patents
ゴム用添加剤、ゴム組成物およびそれを用いた空気入りタイヤ Download PDFInfo
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- JP6560607B2 JP6560607B2 JP2015243617A JP2015243617A JP6560607B2 JP 6560607 B2 JP6560607 B2 JP 6560607B2 JP 2015243617 A JP2015243617 A JP 2015243617A JP 2015243617 A JP2015243617 A JP 2015243617A JP 6560607 B2 JP6560607 B2 JP 6560607B2
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- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0008—Compositions of the inner liner
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0025—Compositions of the sidewalls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C5/00—Inflatable pneumatic tyres or inner tubes
- B60C5/12—Inflatable pneumatic tyres or inner tubes without separate inflatable inserts, e.g. tubeless tyres with transverse section open to the rim
- B60C5/14—Inflatable pneumatic tyres or inner tubes without separate inflatable inserts, e.g. tubeless tyres with transverse section open to the rim with impervious liner or coating on the inner wall of the tyre
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/24—Derivatives of hydrazine
- C08K5/25—Carboxylic acid hydrazides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C2001/005—Compositions of the bead portions, e.g. clinch or chafer rubber or cushion rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(式中、Rは水酸基、炭素数1〜4のアルキル基または炭素数1〜4のアルコキシ基を示し、Aは炭素数1〜4のアルキレン基、または炭素数2〜4のアルケニレン基を示す。)で表されるヒドラジド化合物を含有してなることを特徴とするものである。
(式中、Rは水酸基、炭素数1〜4のアルキル基または炭素数1〜4のアルコキシ基を示し、Aは炭素数1〜4のアルキレン基、または炭素数2〜4のアルケニレン基を示す。)
で表されるヒドラジド化合物を含有してなるものである。
本工程において使用する溶媒としては、反応に対して不活性な溶媒である限り公知の溶媒を広く使用することができる。かかる溶媒としては、例えば、ジメチルエーテル、ジエチルエーテル、ジイソプロピルエーテル、tert−ブチルメチルエーテル、テトラヒドロフラン、ジオキサン、テトラヒドロピラン、1、2−ジメトキシエタン等のエーテル類、ジクロロメタン、クロロホルム、四塩化炭素等のハロゲン類、ヘキサン、シクロヘキサン等の炭化水素類、ベンゼン、トルエン、キシレン、スチレン等の芳香族炭化水素類、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、tert−ブタノール等のアルコール類、アセトニトリル、プロピオニトリル等のニトリル類、N−メチル−2−ピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド等のアミド類、ジメチルスルホキシド、スルホラン等のスルホキシド類を挙げることができる。これらの溶媒は、1種を単独で使用でき、又は必要に応じて2種以上を混合して使用することができる。
本工程は、通常行われるカルボン酸のアルキルエステル化反応を適用すればよく、例えば、エステル化剤としてアルキルアルコールを用いる方法を挙げることができる。
本発明のゴム組成物においては、充填材は、ジエン系ゴム成分100質量部に対して、10〜160質量部、好ましくは30〜100質量部配合される。充填材としては、カーボンブラックが好ましいが、カーボンブラックと無機充填材とを併用してもよい。無機充填材と併用する場合には、ジエン系ゴム成分100質量部に対して、無機充填材を80質量部以下で併用することが好ましい。カーボンブラックを単独配合すれば、カーボンブラックのより強固な補強効果が得られることになる。
3−ヒドロキシ−2−ナフトエ酸ヒドラジド30gをトルエン300mLに懸濁させ、マレイン酸無水物16gを加えて60℃で2時間攪拌した。反応液をろ過し、得られた結晶をトルエンで洗浄後、減圧乾燥により(Z)−4−[N’−(3−ヒドロキシ−2−ナフトイル)ジアザニル]−4−オキソブタ−2−エン酸44.4g(収率99%)を得た。
性状:黄色固体
融点:241℃
1H−NMR(300MHz,DMSO−D6,δppm):6.4(s、2H),7.3(s、1H),7.4(t、1H),7.5(t、1H),7.8(d,1H),7.9(d,1H),8.6(s,1H),11.0(br−s,1H),11.4(br−s,2H),13.3(br−s,1H)
製造例1で製造した(Z)−4−[N’−(3−ヒドロキシ−2−ナフトイル)ジアザニル]4−オキソブタ−2−エン酸10gをメタノール150mLに懸濁させ、硫酸0.44mLを加えて還流下にて7時間攪拌した。トリエチルアミンを加えた後に減圧濃縮して溶媒を留去し、残渣にアセトンを加えてろ過した。得られた固体を熱アセトンで再結晶し、(Z)−4−[N’−(3−ヒドロキシ−2−ナフトイル)ジアザニル]−4−オキソブタ−2-エン酸メチル2.6g(収率25%)を得た。
性状:白色固体
融点:191℃
1H−NMR(300MHz,DMSO−D6,δppm):3.7(s,3H),6.4(d,1H),6.5(d,1H),7.3(s,1H),7.4(t,1H),7.5(t,1H),7.8(d,1H),7.9(d,1H),8.5(s,1H),11.0(br−s,1H),11.1(s,1H),11.5(br−s,1H)
4−メチレンオキセタン−2−オン17.5gにテトラヒドロフラン350mLを加え、3−ヒドロキシ−2−ナフトエ酸ヒドラジド35gを室温で少量ずつ加えた後に、N,N−ジメチルホルムアミド210mLを加えた。室温で2時間攪拌した後に、35℃で一晩加熱攪拌した。反応液をろ過し、ろ紙上の固体をテトラヒドロフランで洗浄(目的物を溶解させる)し、ろ液に水460mLを加えた。析出した結晶をろ過してとり、含水テトラヒドロフランで洗浄した後に減圧乾燥によってN’−(3−ヒドロキシ−2−ナフトイル)−N−(3−オキソブタノ)ヒドラジド11.6g(収率23%)を得た。
性状:薄茶色固体
融点:210℃
1H−NMR(300MHz,DMSO−D6,δppm):2.2(s,3H),3.5(s,2H),7.3(t,2H),7.5 (t,1H),7.7(d,1H),7.9(d,1H),8.5(s,1H),10.7(s,1H),10.8(br−s,1H),11.5(br−s,1H)
下記の表1に示す配合処方により、各種供試ゴム組成物を調製した。得られたゴム組成物に対し、tanδ、スコーチタイムおよびムーニー粘度を測定した。測定方法は下記の通りである。
粘弾性測定装置(レオメトリックス社製)を使用し、温度50℃、歪み5%、周波数15Hzでtanδを測定し、比較例1の値を100として夫々指数表示した。この値が小さい程、低発熱性が良好であることを示す。
未加硫ゴム粘度、スコーチタイムの測定は、JIS K 6300−1:2001(ムーニー粘度、ムーニースコーチタイム)に準拠して行った。夫々比較例1の値を100として指数表示した。スコーチ指数は数値が大きいほどスコーチ性能が良好で、作業性が良好であることを示す。また、ムーニー粘度指数は数値が小さいほど粘度が小さく、作業性が良好であることを示す。
*2 旭カーボン(株)製「♯80」
*3 3−ヒドロキシ−N’−(1,3−ジメチルブチリデン)−2−ナフトエ酸ヒドラジド
*4 特開2014−84312号公報記載の下記化合物
*5 富士興産(株)製「アロマックス#3」
*6 N−(1,3−ジメチルブチル)−N’−フェニル−p−フェニレンジアミン、大内新興化学工業株式会社製、商品名「ノクラック6C」
*7 2,2,4−トリメチル−1,2−ジヒドロキノリン重合体、大内新興化学工業株式会社製、商品名「ノクラック224」
*8 N−シクロヘキシル−2−ベンゾチアゾールスルフェンアミド、三新化学工業(株)製「サンセラーCM」
Claims (8)
- 低ロス剤として用いられる請求項1記載のゴム用添加剤。
- ジエン系ゴム成分100質量部に対して、充填材を10〜160質量部と、請求項1または2記載のゴム用添加剤を0.01〜30質量部と、を配合してなることを特徴とするゴム組成物。
- ジエン系ゴム成分が天然ゴムを含む請求項3記載のゴム組成物。
- 充填剤がカーボンブラックを含む請求項3記載のゴム組成物。
- 請求項3〜5のうちいずれか一項に記載のゴム組成物を用いたことを特徴とする空気入りタイヤ。
- 前記ゴム組成物をトレッド部、サイドウォール部、ビード部、インナーライナーおよびその他の補強ゴム部の少なくとも一つの部材に用いた請求項6記載の空気入りタイヤ。
Priority Applications (5)
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JP2015243617A JP6560607B2 (ja) | 2015-12-14 | 2015-12-14 | ゴム用添加剤、ゴム組成物およびそれを用いた空気入りタイヤ |
EP16875450.5A EP3392303A4 (en) | 2015-12-14 | 2016-12-05 | RUBBER ADDITIVE, RUBBER COMPOSITION AND AIR TIRES THEREWITH |
CN201680073660.XA CN108368310B (zh) | 2015-12-14 | 2016-12-05 | 橡胶用添加剂、橡胶组合物及使用该橡胶组合物的充气轮胎 |
PCT/JP2016/086071 WO2017104467A1 (ja) | 2015-12-14 | 2016-12-05 | ゴム用添加剤、ゴム組成物およびそれを用いた空気入りタイヤ |
US16/061,462 US20200263001A1 (en) | 2015-12-14 | 2016-12-05 | Rubber additive, rubber composition and pneumatic tire using same |
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JP2015243617A JP6560607B2 (ja) | 2015-12-14 | 2015-12-14 | ゴム用添加剤、ゴム組成物およびそれを用いた空気入りタイヤ |
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JP6560607B2 true JP6560607B2 (ja) | 2019-08-14 |
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US (1) | US20200263001A1 (ja) |
EP (1) | EP3392303A4 (ja) |
JP (1) | JP6560607B2 (ja) |
CN (1) | CN108368310B (ja) |
WO (1) | WO2017104467A1 (ja) |
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EP3495415B1 (en) | 2016-08-04 | 2021-01-20 | Bridgestone Corporation | Rubber composition, tire, additive, and hydrazide compound |
CN114929665A (zh) * | 2019-12-20 | 2022-08-19 | 大塚化学株式会社 | 晶体及其制造方法 |
EP4079535A4 (en) * | 2019-12-20 | 2024-01-24 | Otsuka Chemical Co., Ltd. | CRYSTAL AND METHOD FOR PRODUCING THEREOF |
CN114395116B (zh) * | 2022-01-27 | 2024-03-12 | 江苏麒祥高新材料有限公司 | 聚酯酰肼、橡胶组合物、轮胎及其制备方法和用途 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JPH0827315A (ja) * | 1994-07-15 | 1996-01-30 | Bridgestone Corp | ゴム組成物の混練り方法 |
DE69827906T2 (de) * | 1997-04-02 | 2005-05-19 | Bridgestone Corp. | Kautschukzusammensetzung und reifen |
JP4086359B2 (ja) * | 1997-04-02 | 2008-05-14 | 株式会社ブリヂストン | 空気入りタイヤ |
JPH11231462A (ja) * | 1998-02-12 | 1999-08-27 | Ricoh Co Ltd | 熱現像型ジアゾ複写材料 |
US20050103415A1 (en) * | 2003-11-18 | 2005-05-19 | Lukich Lewis T. | Tire with shock absorbing closed cell rubber tread of spaced apart lugs |
JP5292023B2 (ja) * | 2008-08-28 | 2013-09-18 | 精工化学株式会社 | 重合抑制方法及び重合抑制剤 |
CN101979255B (zh) * | 2010-11-05 | 2012-07-25 | 张雨军 | 一种乘用车用耐穿刺安全轮胎 |
-
2015
- 2015-12-14 JP JP2015243617A patent/JP6560607B2/ja active Active
-
2016
- 2016-12-05 CN CN201680073660.XA patent/CN108368310B/zh active Active
- 2016-12-05 WO PCT/JP2016/086071 patent/WO2017104467A1/ja active Application Filing
- 2016-12-05 EP EP16875450.5A patent/EP3392303A4/en not_active Withdrawn
- 2016-12-05 US US16/061,462 patent/US20200263001A1/en not_active Abandoned
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JP2017110052A (ja) | 2017-06-22 |
WO2017104467A1 (ja) | 2017-06-22 |
CN108368310A (zh) | 2018-08-03 |
CN108368310B (zh) | 2020-12-01 |
EP3392303A1 (en) | 2018-10-24 |
US20200263001A1 (en) | 2020-08-20 |
EP3392303A4 (en) | 2019-01-23 |
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