DE69902566T2 - Verfahren zur Herstellung von modifizierten Terpen-Phenol Harzen - Google Patents
Verfahren zur Herstellung von modifizierten Terpen-Phenol HarzenInfo
- Publication number
- DE69902566T2 DE69902566T2 DE69902566T DE69902566T DE69902566T2 DE 69902566 T2 DE69902566 T2 DE 69902566T2 DE 69902566 T DE69902566 T DE 69902566T DE 69902566 T DE69902566 T DE 69902566T DE 69902566 T2 DE69902566 T2 DE 69902566T2
- Authority
- DE
- Germany
- Prior art keywords
- terpene
- phenol
- pinene
- olefin
- range
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 36
- 239000005011 phenolic resin Substances 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 64
- 239000000047 product Substances 0.000 claims description 46
- 150000001336 alkenes Chemical class 0.000 claims description 45
- 150000003505 terpenes Chemical class 0.000 claims description 44
- 235000007586 terpenes Nutrition 0.000 claims description 44
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 27
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims description 27
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 23
- 229920005989 resin Polymers 0.000 claims description 23
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 claims description 18
- 125000002015 acyclic group Chemical group 0.000 claims description 16
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 16
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 14
- -1 boron halides Chemical class 0.000 claims description 12
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 10
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 10
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000008096 xylene Substances 0.000 claims description 9
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 8
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims description 8
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims description 8
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 8
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims description 8
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 8
- 229930006722 beta-pinene Natural products 0.000 claims description 8
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims description 8
- 239000011968 lewis acid catalyst Substances 0.000 claims description 7
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 claims description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 6
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229940069096 dodecene Drugs 0.000 claims description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- LFJQCDVYDGGFCH-JTQLQIEISA-N (+)-β-phellandrene Chemical compound CC(C)[C@@H]1CCC(=C)C=C1 LFJQCDVYDGGFCH-JTQLQIEISA-N 0.000 claims description 3
- LFJQCDVYDGGFCH-SNVBAGLBSA-N (+/-)-beta-Phellandrene Natural products CC(C)[C@H]1CCC(=C)C=C1 LFJQCDVYDGGFCH-SNVBAGLBSA-N 0.000 claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- LFJQCDVYDGGFCH-UHFFFAOYSA-N beta-phellandrene Natural products CC(C)C1CCC(=C)C=C1 LFJQCDVYDGGFCH-UHFFFAOYSA-N 0.000 claims description 3
- 235000001510 limonene Nutrition 0.000 claims description 3
- 229940087305 limonene Drugs 0.000 claims description 3
- 238000000197 pyrolysis Methods 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000000376 reactant Substances 0.000 description 14
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229910015900 BF3 Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000003637 basic solution Substances 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- IXKVYSRDIVLASR-UHFFFAOYSA-N 2,3-dioctylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1CCCCCCCC IXKVYSRDIVLASR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000845082 Panama Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003447 alpha-pinene group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920003247 engineering thermoplastic Polymers 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 150000003739 xylenols Chemical class 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69902566D1 DE69902566D1 (de) | 2002-09-26 |
| DE69902566T2 true DE69902566T2 (de) | 2002-12-19 |
Family
ID=22164563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69902566T Expired - Lifetime DE69902566T2 (de) | 1998-05-19 | 1999-05-18 | Verfahren zur Herstellung von modifizierten Terpen-Phenol Harzen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6160083A (enExample) |
| EP (1) | EP0959089B1 (enExample) |
| JP (1) | JP4730987B2 (enExample) |
| DE (1) | DE69902566T2 (enExample) |
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 |
| EP1913075B1 (en) * | 2005-08-09 | 2014-12-17 | Arizona Chemical Company | Rubber compositions containing improved tackifiers |
| FI126885B (fi) | 2011-05-31 | 2017-07-14 | Stora Enso Oyj | Terpeenifenolihartsin käyttö ekstruusiopinnoituksessa |
| WO2017106448A1 (en) | 2015-12-18 | 2017-06-22 | 3M Innovative Properties Company | Metal-containing sorbents for nitrogen-containing compounds |
| KR20180095656A (ko) | 2015-12-22 | 2018-08-27 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 수계 (메트)아크릴레이트 접착제 조성물에 내부적으로 혼입된 페놀 수지, 예비-접착제 반응 혼합물, 방법 및 용품 |
| CN108779370B (zh) | 2015-12-22 | 2021-02-12 | 3M创新有限公司 | 包含含聚乳酸的包装材料的包装的预粘合剂组合物、粘合剂和制品 |
| JP2019533738A (ja) | 2016-10-14 | 2019-11-21 | クレイトン・ケミカル・エル・エル・シー | 改良されたトレッド増強添加剤を含有するゴム組成物及びその使用 |
| 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 |
| WO2018125895A1 (en) * | 2016-12-28 | 2018-07-05 | Swimc, Llc | Packaging coating resins derived from reactions of phenols with polyolefinic terpenes |
| EP3864102B1 (en) | 2018-10-11 | 2024-11-27 | 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 EP EP99850084A patent/EP0959089B1/en not_active Expired - Lifetime
- 1999-05-18 DE DE69902566T patent/DE69902566T2/de not_active Expired - Lifetime
- 1999-05-19 JP JP13836799A patent/JP4730987B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6160083A (en) | 2000-12-12 |
| JP4730987B2 (ja) | 2011-07-20 |
| EP0959089B1 (en) | 2002-08-21 |
| JP2000001528A (ja) | 2000-01-07 |
| DE69902566D1 (de) | 2002-09-26 |
| EP0959089A1 (en) | 1999-11-24 |
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