JP2000001528A5 - - Google Patents
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- Publication number
- JP2000001528A5 JP2000001528A5 JP1999138367A JP13836799A JP2000001528A5 JP 2000001528 A5 JP2000001528 A5 JP 2000001528A5 JP 1999138367 A JP1999138367 A JP 1999138367A JP 13836799 A JP13836799 A JP 13836799A JP 2000001528 A5 JP2000001528 A5 JP 2000001528A5
- Authority
- JP
- Japan
- Prior art keywords
- phenol
- terpene
- pinene
- group
- solvent
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 description 40
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 16
- 239000005011 phenolic resin Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 150000001336 alkenes Chemical class 0.000 description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 11
- 150000003505 terpenes Chemical class 0.000 description 11
- 235000007586 terpenes Nutrition 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 9
- -1 boron halides Chemical class 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 9
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 8
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 8
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 8
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 8
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 8
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 8
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 8
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 8
- 125000002015 acyclic group Chemical group 0.000 description 8
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 8
- 229930006722 beta-pinene Natural products 0.000 description 8
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 8
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 5
- 239000011968 lewis acid catalyst Substances 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003447 alpha-pinene group Chemical group 0.000 description 4
- 229940069096 dodecene Drugs 0.000 description 4
- 235000001510 limonene Nutrition 0.000 description 4
- 229940087305 limonene Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/081,496 US6160083A (en) | 1998-05-19 | 1998-05-19 | Method for making modified terpene-phenol resins |
| US081496 | 1998-05-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2000001528A JP2000001528A (ja) | 2000-01-07 |
| JP2000001528A5 true JP2000001528A5 (https=) | 2006-06-29 |
| JP4730987B2 JP4730987B2 (ja) | 2011-07-20 |
Family
ID=22164563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13836799A Expired - Lifetime JP4730987B2 (ja) | 1998-05-19 | 1999-05-19 | 改質テルペン−フェノール樹脂の製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6160083A (https=) |
| EP (1) | EP0959089B1 (https=) |
| JP (1) | JP4730987B2 (https=) |
| DE (1) | DE69902566T2 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4929634A (en) | 1987-10-23 | 1990-05-29 | American Cyanamid Company | Method of and bait compositions for controlling mollusks |
| JP2002069408A (ja) * | 2000-08-29 | 2002-03-08 | Nippon Petrochem Co Ltd | ホットメルト組成物およびホットメルト組成物用変性芳香族石油樹脂 |
| EP2940072B1 (en) | 2005-08-09 | 2020-05-27 | Kraton Chemical, LLC | Rubber compositions containing improved tackifiers |
| FI126885B (fi) | 2011-05-31 | 2017-07-14 | Stora Enso Oyj | Terpeenifenolihartsin käyttö ekstruusiopinnoituksessa |
| CN108472624B (zh) | 2015-12-18 | 2022-03-18 | 3M创新有限公司 | 用于含氮化合物的含金属吸附剂 |
| US10597564B2 (en) | 2015-12-22 | 2020-03-24 | 3M Innovative Properties Company | Internally incorporated phenolic resins in water-based (meth)acrylate adhesive compositions, pre-adhesive reaction mixtures, methods, and articles |
| WO2017112386A1 (en) | 2015-12-22 | 2017-06-29 | 3M Innovative Properties Company | Packaged pre-adhesive composition including a polylactic acid-containing packaging material, adhesives, and articles |
| EP3512890A4 (en) | 2016-10-14 | 2020-06-03 | Kraton Chemical, LLC. | RUBBER COMPOSITIONS WITH IMPROVED TREAD REINFORCEMENT ADDITIVES AND USE THEREOF |
| CN106589322B (zh) * | 2016-11-18 | 2018-09-25 | 江苏麒祥高新材料有限公司 | 一种改性萜烯酚树脂及其制备方法及其在轮胎胎面胶中的应用 |
| CN110139805B (zh) * | 2016-12-28 | 2022-02-11 | 宣伟投资管理有限公司 | 衍生自酚与多烯烃萜烯的反应的包装涂料树脂 |
| US20210317341A1 (en) | 2018-10-11 | 2021-10-14 | 3M Innovative Properties Company | Adhesive composition comprising block copolymer with polyvinyl aromatic endblock and poly(vinyl aromatic/butadiene) copolymer block and sis block copolymer, articles, and methods |
| CN112063100A (zh) * | 2020-09-14 | 2020-12-11 | 江苏麒祥高新材料有限公司 | 一种改性树脂液及其制备方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2343845A (en) * | 1941-12-20 | 1944-03-07 | Armstrong Cork Co | Synthetic resin |
| US2471455A (en) * | 1944-11-07 | 1949-05-31 | Hercules Powder Co Ltd | Preparation of terpene phenols |
| US2596235A (en) * | 1947-10-02 | 1952-05-13 | Neville Co | Terpene-phenolic reaction product |
| DE1222050B (de) * | 1962-06-05 | 1966-08-04 | Hoechst Ag | Verfahren zur Herstellung von modifizierten Terpenphenolkondensaten |
| US3297673A (en) * | 1963-10-03 | 1967-01-10 | Tenneco Chem | Production of terpene resins |
| US3383362A (en) * | 1965-04-05 | 1968-05-14 | Schenectady Chemical | Phenol-terpene-cyclic polyolefin polymer |
| US3692844A (en) * | 1968-06-24 | 1972-09-19 | Pennsylvania Ind Chem Corp | Process for preparing a terpene phenolic condensation product |
| US3929938A (en) * | 1971-08-23 | 1975-12-30 | Reichhold Chemicals Inc | Limonene/phenol condensation products and hot-melt adhesives containing the same along with ethylene/unsaturated ester copolymers |
| US3976606A (en) * | 1973-10-23 | 1976-08-24 | Minnesota Mining And Manufacturing Company | Adhesives tackified with low molecular weight terpene-phenolic resins |
| US3993626A (en) * | 1974-12-12 | 1976-11-23 | Neville Chemical Company | Production of ethyl cellulose-compatible phenol-modified hydrocarbon resins for use in printing inks |
| FR2303817A1 (fr) * | 1975-03-11 | 1976-10-08 | Derives Resiniques Terpenique | Procede de preparation de resines terpene-phenol |
| US4081425A (en) * | 1975-11-21 | 1978-03-28 | Hoechst Aktiengesellschaft | Process for the manufacture of light color terpenephenols |
| US4279659A (en) * | 1976-10-18 | 1981-07-21 | Petrolite Corporation | Laminating composition and uses |
| JPS56157414A (en) * | 1980-05-09 | 1981-12-04 | Nippon Oil Co Ltd | Production of hydrocarbon resin |
| GB8727636D0 (en) * | 1987-11-25 | 1987-12-31 | Exxon Chemical Patents Inc | Adhesive formulations |
| JP2803083B2 (ja) * | 1988-01-22 | 1998-09-24 | 三井化学株式会社 | 重合体組成物およびその用途 |
| EP0610632A1 (en) * | 1993-02-11 | 1994-08-17 | Dsm N.V. | Resinous copolymer |
| JP3223012B2 (ja) * | 1993-11-17 | 2001-10-29 | 三井化学株式会社 | フェノール樹脂、その製造方法および用途 |
| JPH0853539A (ja) * | 1994-08-12 | 1996-02-27 | Dainippon Ink & Chem Inc | フェノール樹脂の製造方法及びエポキシ樹脂の製造方法 |
| US5457175A (en) * | 1995-01-11 | 1995-10-10 | Arizona Chemical Company | Low softening point terpene-phenol resins |
| JP3292616B2 (ja) * | 1995-02-08 | 2002-06-17 | 日石三菱株式会社 | フェノール樹脂および樹脂組成物 |
-
1998
- 1998-05-19 US US09/081,496 patent/US6160083A/en not_active Expired - Lifetime
-
1999
- 1999-05-18 DE DE69902566T patent/DE69902566T2/de not_active Expired - Lifetime
- 1999-05-18 EP EP99850084A patent/EP0959089B1/en not_active Expired - Lifetime
- 1999-05-19 JP JP13836799A patent/JP4730987B2/ja not_active Expired - Lifetime
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