JP6798039B2 - 官能化リグニンを含む空気入りタイヤ用の高剛性配合物 - Google Patents
官能化リグニンを含む空気入りタイヤ用の高剛性配合物 Download PDFInfo
- Publication number
- JP6798039B2 JP6798039B2 JP2019546080A JP2019546080A JP6798039B2 JP 6798039 B2 JP6798039 B2 JP 6798039B2 JP 2019546080 A JP2019546080 A JP 2019546080A JP 2019546080 A JP2019546080 A JP 2019546080A JP 6798039 B2 JP6798039 B2 JP 6798039B2
- Authority
- JP
- Japan
- Prior art keywords
- lignin
- formulation
- functionalized lignin
- functionalized
- pneumatic tires
- 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.)
- Active
Links
- 229920005610 lignin Polymers 0.000 title claims description 42
- 239000000203 mixture Substances 0.000 title claims description 34
- 238000009472 formulation Methods 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 238000002156 mixing Methods 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 239000011324 bead Substances 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 9
- 238000010058 rubber compounding Methods 0.000 claims description 9
- 238000004073 vulcanization Methods 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 6
- 238000007306 functionalization reaction Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000012763 reinforcing filler Substances 0.000 claims description 5
- 239000006229 carbon black Substances 0.000 claims description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 17
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 17
- 238000004132 cross linking Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229920005611 kraft lignin Polymers 0.000 description 3
- 239000002655 kraft paper Substances 0.000 description 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000002355 alkine group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000019241 carbon black Nutrition 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001251054 Formica truncorum Species 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- JMFRWRFFLBVWSI-UHFFFAOYSA-N cis-coniferyl alcohol Natural products COC1=CC(C=CCO)=CC=C1O JMFRWRFFLBVWSI-UHFFFAOYSA-N 0.000 description 1
- LZFOPEXOUVTGJS-UHFFFAOYSA-N cis-sinapyl alcohol Natural products COC1=CC(C=CCO)=CC(OC)=C1O LZFOPEXOUVTGJS-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- JMFRWRFFLBVWSI-NSCUHMNNSA-N coniferol Chemical compound COC1=CC(\C=C\CO)=CC=C1O JMFRWRFFLBVWSI-NSCUHMNNSA-N 0.000 description 1
- 229940119526 coniferyl alcohol Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- LZFOPEXOUVTGJS-ONEGZZNKSA-N trans-sinapyl alcohol Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O LZFOPEXOUVTGJS-ONEGZZNKSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- B60C2001/0058—Compositions of the bead apexes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Materials Engineering (AREA)
- Reinforced Plastic Materials (AREA)
- Heat Treatment Of Steel (AREA)
Description
1つ目(配合物A)は、第1の比較例かつ先行技術配合物を表し、メチレン受容体化合物が第1の非生産混合ステップの間に添加され、メチレン供与体化合物が生産混合ステップの間に添加される;
2つ目(配合物B)は、別の比較例を表し、メチレン受容体化合物とメチレン供与体化合物の両方が、生産混合ステップの間に添加される;
3つ目(配合物C)は、さらなる比較例を表し、メチレン受容体化合物とメチレン供与体化合物とによって表される二成分樹脂の代わりに、非官能化リグニンを用いた;
4つ目(配合物D)は、本発明の実施例を表し、メチレン受容体化合物とメチレン供与体化合物とによって表される二成分樹脂の代わりに、本発明の官能化リグニンを用いた。
(第1の非生産混合ステップ)
混合開始前に、230〜270リットルの内容積を有する密閉式チャンバーミキサーに表Iに記載の成分を充填し、66〜72%の充填率とした。
前のステップからの混合物を40〜60rpmの速度で運転しているミキサー中で再加工し、次に130〜150℃の温度に達したところで除去した。
表Iに挙げた成分を前のステップから得た混合物に添加して、63〜67%の充填率とした。
Claims (4)
- 架橋性不飽和鎖ポリマー、補強性充填剤、熱硬化性樹脂および加硫系を含む、空気入りタイヤのビードフィラーの製造用ゴム配合物であり;前記配合物は、前記熱硬化性樹脂が、−OR基を有する官能化リグニンを含み、式中、Rは、−CH 2 CCHであり、
前記補強性充填剤が、カーボンブラックであり、
前記−OR基が、リグニンの5〜100%のヒドロキシルフェノール基の官能化に由来し、
前記官能化リグニンが、クラフトリグニンに由来し、
前記ゴム配合物は、5〜15phrの前記官能化リグニンを含み、
前記官能化リグニンが、生産混合ステップの調製において前記ゴム配合物に添加される、ことを特徴とする、空気入りタイヤのビードフィラーの製造用ゴム配合物。 - 請求項1に記載の配合物を用いて製造された、空気入りタイヤのビードフィラー。
- 請求項2に記載のビードフィラーを含む、空気入りタイヤ。
- 架橋性不飽和鎖ポリマー、補強性充填剤、熱硬化性樹脂および加硫系を含む、空気入りタイヤのビードフィラーの製造用ゴム配合物における熱硬化性樹脂としての官能化リグニンの使用であって;前記官能化リグニンは、−OR基を含み、式中、Rは、−CH 2 CCHであり、
前記補強性充填剤が、カーボンブラックであり、
前記−OR基が、リグニンの5〜100%のヒドロキシルフェノール基の官能化に由来し、
前記官能化リグニンが、クラフトリグニンに由来し、
前記ゴム配合物は、5〜15phrの前記官能化リグニンを含み、
前記官能化リグニンが、生産混合ステップの調製において前記ゴム配合物に添加される、使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT102016000120857 | 2016-11-29 | ||
IT102016000120857A IT201600120857A1 (it) | 2016-11-29 | 2016-11-29 | Mescola ad elevata rigidezza per pneumatici comprendente lignina funzionalizzata |
PCT/EP2017/080375 WO2018099822A1 (en) | 2016-11-29 | 2017-11-24 | High rigidity compound for pneumatic tyres comprising functionalized lignin |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2019535592A JP2019535592A (ja) | 2019-12-12 |
JP6798039B2 true JP6798039B2 (ja) | 2020-12-09 |
Family
ID=58347827
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019546080A Active JP6798039B2 (ja) | 2016-11-29 | 2017-11-24 | 官能化リグニンを含む空気入りタイヤ用の高剛性配合物 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11242447B2 (ja) |
EP (1) | EP3548303B1 (ja) |
JP (1) | JP6798039B2 (ja) |
IT (1) | IT201600120857A1 (ja) |
WO (1) | WO2018099822A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT202000008497A1 (it) * | 2020-04-21 | 2021-10-21 | Bridgestone Europe Nv Sa | Mescola ad elevata impermeabilita' per innerliner e metodo per la sua realizzazione |
IT202000016285A1 (it) * | 2020-07-06 | 2022-01-06 | Bridgestone Europe Nv Sa | Mescola in gomma ad elevata rigidezza per porzioni di pneumatico |
CN114426715B (zh) * | 2020-10-10 | 2023-07-04 | 中国石油化工股份有限公司 | 一种大粒径木质素/丁苯橡胶复合粒子及其合成方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0299074B1 (en) * | 1987-01-14 | 1992-01-29 | Bridgestone Corporation | Tire |
US8664305B2 (en) * | 2009-02-10 | 2014-03-04 | The Goodyear Tire & Rubber Company | Functionalized lignin, rubber containing functionalized lignin and products containing such rubber composition |
US9340426B2 (en) * | 2012-02-21 | 2016-05-17 | North Carolina State University | High value lignin derivatives, polymers, and copolymers and use thereof in thermoplastic, thermoset, composite, and carbon fiber applications |
WO2014097108A1 (en) * | 2012-12-18 | 2014-06-26 | Pirelli Tyre S.P.A. | Tyre for vehicle wheels |
JP6422708B2 (ja) * | 2014-09-12 | 2018-11-14 | 日本製紙株式会社 | ゴム補強用のリグニン誘導体の製造方法、リグニン樹脂組成物の製造方法およびゴム組成物の製造方法 |
US10138377B2 (en) * | 2014-09-12 | 2018-11-27 | Sumitomo Bakelite Co., Ltd. | Lignin derivative, lignin resin composition, rubber composition, and molding material |
JP6656960B2 (ja) * | 2015-03-13 | 2020-03-04 | 国立大学法人京都大学 | リグニンを構成するフェニルプロパン単位のα位が化学修飾されたリグノセルロース誘導体、それを含む繊維、繊維集合体、それらを含有する組成物及び成形体 |
-
2016
- 2016-11-29 IT IT102016000120857A patent/IT201600120857A1/it unknown
-
2017
- 2017-11-24 US US16/463,090 patent/US11242447B2/en active Active
- 2017-11-24 JP JP2019546080A patent/JP6798039B2/ja active Active
- 2017-11-24 EP EP17801482.5A patent/EP3548303B1/en active Active
- 2017-11-24 WO PCT/EP2017/080375 patent/WO2018099822A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
US20190284372A1 (en) | 2019-09-19 |
EP3548303A1 (en) | 2019-10-09 |
WO2018099822A1 (en) | 2018-06-07 |
EP3548303B1 (en) | 2020-03-25 |
JP2019535592A (ja) | 2019-12-12 |
US11242447B2 (en) | 2022-02-08 |
IT201600120857A1 (it) | 2018-05-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6733546B2 (ja) | ゴム組成物およびリグニン誘導体の製造方法 | |
JP6798039B2 (ja) | 官能化リグニンを含む空気入りタイヤ用の高剛性配合物 | |
CN104448425B (zh) | 一种橡胶组合物以及使用其的轮胎 | |
JP6715181B2 (ja) | タイヤ製造用ゴム配合物 | |
EP3059274A1 (en) | Resin composition and rubber composition | |
US10035905B2 (en) | Rubber compounds containing silicon dioxide for the production of tyres | |
JP2019537660A (ja) | 酸化防止剤としてのリグニンを含む空気入りタイヤ部品用のゴム配合物 | |
JP6406948B2 (ja) | ゴム補強用のリグニン誘導体、ゴム補強用のリグニン誘導体の製造方法、リグニン樹脂組成物およびゴム組成物 | |
US20160230008A1 (en) | Resin composition, rubber composition, and cured article | |
JP2016060750A (ja) | ゴム補強用のリグニン誘導体、リグニン樹脂組成物およびゴム組成物 | |
JP5828224B2 (ja) | タイヤビードフィラー用ゴム組成物およびそれを用いた空気入りタイヤ | |
JP6716043B2 (ja) | 分散剤としてのリグニンを含む空気入りタイヤ部品用のゴム配合物 | |
JP5830938B2 (ja) | タイヤ用ゴム組成物およびそれを用いた空気入りタイヤの製造方法 | |
WO2022008452A1 (en) | High-rigidity rubber compound for pneumatic tyre portions | |
JP6193577B2 (ja) | タイヤ用ゴム組成物及び空気入りタイヤ | |
ITUB20155282A1 (it) | Mescola in gomma per la produzione di pneumatici comprendente gomma riciclata | |
JP2015205949A (ja) | タイヤビードインシュレーション用ゴム組成物およびそれを用いた空気入りタイヤ |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190508 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200623 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200811 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20201110 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20201118 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6798039 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |