JP6541007B2 - フェノール変性リグニン樹脂及びその製造方法、並びに、樹脂組成物、ゴム組成物、及び硬化物 - Google Patents
フェノール変性リグニン樹脂及びその製造方法、並びに、樹脂組成物、ゴム組成物、及び硬化物 Download PDFInfo
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- JP6541007B2 JP6541007B2 JP2016510485A JP2016510485A JP6541007B2 JP 6541007 B2 JP6541007 B2 JP 6541007B2 JP 2016510485 A JP2016510485 A JP 2016510485A JP 2016510485 A JP2016510485 A JP 2016510485A JP 6541007 B2 JP6541007 B2 JP 6541007B2
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- lignin
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- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
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- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
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- 239000011259 mixed solution Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- CYGSXDXRHXMAOV-UHFFFAOYSA-N o-cresol hydrogen sulfate Chemical compound CC1=CC=CC=C1OS(O)(=O)=O CYGSXDXRHXMAOV-UHFFFAOYSA-N 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000012086 standard solution 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
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
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- 229920001187 thermosetting polymer Polymers 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
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- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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- 239000012498 ultrapure water Substances 0.000 description 1
- DQTMTQZSOJMZSF-UHFFFAOYSA-N urushiol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DQTMTQZSOJMZSF-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/38—Block or graft polymers prepared by polycondensation of aldehydes or ketones onto macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols with polyhydric phenols
-
- 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
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)
- Phenolic Resins Or Amino Resins (AREA)
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| JP2014104583 | 2014-05-20 | ||
| PCT/JP2015/059372 WO2015147165A1 (ja) | 2014-03-28 | 2015-03-26 | フェノール変性リグニン樹脂及びその製造方法、並びに、樹脂組成物、ゴム組成物、及び硬化物 |
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| JPWO2015147165A1 JPWO2015147165A1 (ja) | 2017-04-13 |
| JP6541007B2 true JP6541007B2 (ja) | 2019-07-10 |
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| CN (1) | CN105873970B (zh) |
| WO (1) | WO2015147165A1 (zh) |
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| DE112017000191T5 (de) * | 2016-04-19 | 2018-08-02 | Fuji Electric Co., Ltd. | Harzzusammensetzung mit Ligninskelett und Gießteil, das die Harzzusammensetzung enthält |
| EP3511379A4 (en) * | 2016-09-09 | 2020-04-22 | Idemitsu Kosan Co., Ltd. | PROCESS FOR PRODUCING LIGNIN CONTAINING RESIN COMPOSITION, AND LIGNIN CONTAINING RESIN MOLDING PART |
| CN106633622B (zh) * | 2016-09-21 | 2018-10-12 | 沈阳化工大学 | 一种含有玉米素基团的酚醛树脂及其制备方法 |
| JP2020055888A (ja) * | 2017-01-24 | 2020-04-09 | ハリマ化成株式会社 | ノボラック型フェノール樹脂、樹脂組成物およびノボラック型フェノール樹脂の製造方法 |
| IT201700007087A1 (it) * | 2017-01-24 | 2018-07-24 | Bridgestone Corp | Mescole in gomma per parti di pneumatico comprendenti lignina come agente disperdente |
| JP2020094078A (ja) * | 2017-03-28 | 2020-06-18 | ハリマ化成株式会社 | 摺動材 |
| JP2020094079A (ja) * | 2017-03-28 | 2020-06-18 | ハリマ化成株式会社 | 摺動材 |
| WO2019031610A1 (ja) | 2017-08-10 | 2019-02-14 | 出光興産株式会社 | 改質リグニンの製造方法及び改質リグニン、並びに改質リグニン含有樹脂組成材料 |
| EP3666784A4 (en) | 2017-08-10 | 2021-04-14 | Idemitsu Kosan Co.,Ltd. | PROCESS FOR THE MANUFACTURING OF MODIFIED LIGNIN AND MODIFIED POLYPHENOL, AND MATERIAL OF COMPOSITION OF RESIN CONTAINING MODIFIED LIGNIN |
| KR20200049849A (ko) * | 2017-09-07 | 2020-05-08 | 렌매틱스, 인코포레이티드. | 중합체 내 항산화제 안정제 |
| FR3080627B1 (fr) * | 2018-04-26 | 2021-02-26 | Porcher Ind | Composition d'adherisage pour textile et textile de renfort y relatif |
| JP2020050814A (ja) * | 2018-09-28 | 2020-04-02 | 住友ベークライト株式会社 | フェノール変性リグニン樹脂を含む樹脂材料、それを用いたフェノール変性リグニン樹脂組成物および構造体 |
| BR102018077291B1 (pt) * | 2018-12-27 | 2024-02-20 | Suzano S.A. | Resinas fenólicas do tipo novolaca, processo de síntese das referidas resinas fenólicas e uso das mesmas |
| CN111763358B (zh) * | 2019-04-02 | 2022-12-09 | 中国石油化工股份有限公司 | 一种含有橡胶改性剂的橡胶组合物和一种硫化橡胶及其制备方法和应用 |
| CN110776696A (zh) * | 2019-12-07 | 2020-02-11 | 界首市鑫豪塑胶有限公司 | 一种复合木质素改善三元乙丙橡胶硫化特性的方法 |
| CN117120498A (zh) * | 2021-04-06 | 2023-11-24 | 住友电木株式会社 | 木质素改性酚醛清漆型酚醛树脂及其制造方法以及成型材料、树脂组合物和磨具 |
| JP7197064B1 (ja) * | 2021-04-06 | 2022-12-27 | 住友ベークライト株式会社 | 摩擦材用熱硬化性樹脂組成物および摩擦材 |
| CN113929976B (zh) * | 2021-10-26 | 2023-12-22 | 东莞市昌泰鞋业有限公司 | 一种休闲鞋及其制备方法 |
| CN115490880B (zh) * | 2022-10-10 | 2023-11-21 | 上海昶法新材料有限公司 | 一种改性木质素的制备方法及其应用 |
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