JP2016538352A5 - - Google Patents
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- Publication number
- JP2016538352A5 JP2016538352A5 JP2016518134A JP2016518134A JP2016538352A5 JP 2016538352 A5 JP2016538352 A5 JP 2016538352A5 JP 2016518134 A JP2016518134 A JP 2016518134A JP 2016518134 A JP2016518134 A JP 2016518134A JP 2016538352 A5 JP2016538352 A5 JP 2016538352A5
- Authority
- JP
- Japan
- Prior art keywords
- rosin ester
- composition
- rosin
- esterified
- composition according
- 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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 87
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 87
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 87
- 239000000203 mixture Substances 0.000 claims description 83
- 150000002148 esters Chemical class 0.000 claims description 66
- 229920000642 polymer Polymers 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 26
- UZZYXZWSOWQPIS-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C=O)=CC(C(F)(F)F)=C1 UZZYXZWSOWQPIS-UHFFFAOYSA-N 0.000 claims description 19
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 claims description 19
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 claims description 19
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 claims description 19
- 229940118781 dehydroabietic acid Drugs 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- 239000003784 tall oil Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000007323 disproportionation reaction Methods 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361883725P | 2013-09-27 | 2013-09-27 | |
| US61/883,725 | 2013-09-27 | ||
| PCT/US2014/057674 WO2015048415A2 (en) | 2013-09-27 | 2014-09-26 | Rosin esters and compositions thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016538352A JP2016538352A (ja) | 2016-12-08 |
| JP2016538352A5 true JP2016538352A5 (cg-RX-API-DMAC7.html) | 2017-11-09 |
| JP6789812B2 JP6789812B2 (ja) | 2020-11-25 |
Family
ID=51842774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016518134A Active JP6789812B2 (ja) | 2013-09-27 | 2014-09-26 | ロジンエステル及びその組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10011740B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3049491A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6789812B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102366374B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN105916949A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2015048415A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2530281A (en) * | 2014-09-17 | 2016-03-23 | Arjobex Ltd | Voided plastics film |
| KR102524275B1 (ko) * | 2015-09-11 | 2023-04-21 | 아라까와 가가꾸 고교 가부시끼가이샤 | 가소제 및 광학용 점·접착제 조성물 |
| WO2018074273A1 (ja) * | 2016-10-17 | 2018-04-26 | 荒川化学工業株式会社 | 複合プラスチック成形物 |
| WO2018212154A1 (ja) * | 2017-05-17 | 2018-11-22 | ハリマ化成株式会社 | 粘着付与樹脂および粘着剤組成物 |
| JP7179784B2 (ja) * | 2017-06-30 | 2022-11-29 | クレイトン・ポリマーズ・エル・エル・シー | 淡色ロジンエステル組成物及びこれを製造する方法 |
| US11034914B2 (en) * | 2018-05-01 | 2021-06-15 | Kraton Polymers Llc | Desulfurized black liquor soap compositions and processes for producing |
| US11034858B2 (en) * | 2018-12-21 | 2021-06-15 | Kraton Polymers Llc | Light-colored rosin and rosin ester compositions |
| US20230220205A1 (en) | 2020-05-29 | 2023-07-13 | Industrias Alen, S.A. De C.V. | Wax-like formulations of natural-origin materials and its method of preparation |
| FR3118046B1 (fr) * | 2020-12-23 | 2022-12-30 | Michelin & Cie | Composition de caoutchouc comprenant un élastomère diénique fortement saturé |
| FR3118045B1 (fr) * | 2020-12-23 | 2022-12-30 | Michelin & Cie | Composition de caoutchouc |
| US11572472B2 (en) | 2021-03-31 | 2023-02-07 | Adventus Material Strategies, Llc | Pigmentable, non-asphalt based, sealant composition and methods of production and use |
| KR102421999B1 (ko) * | 2021-11-05 | 2022-07-18 | 주식회사 정석케미칼 | 시공성 및 품질 균일성을 개선한 펠릿타입 열 융착형 노면표지용 도료 조성물 및 그 제조방법 |
| FI131246B1 (en) * | 2023-12-22 | 2025-01-07 | Neste Oyj | Process for the production of rosin esters |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1820265A (en) | 1928-11-24 | 1931-08-25 | Hercules Powder Co Ltd | Ester gum and method of producing |
| US2051796A (en) | 1929-12-02 | 1936-08-18 | Hercules Powder Co Ltd | Hydrogenated resin esters and their production |
| US2239555A (en) | 1938-03-19 | 1941-04-22 | Elmer E Fleck | Stable rosin acid, rosin ester, and rosin product containing them and a method for their production |
| US2729660A (en) | 1953-01-21 | 1956-01-03 | Gen Mills Inc | Phosphite esters as esterification catalysts |
| US2749614A (en) | 1955-04-29 | 1956-06-12 | Ellis W Volkel | Rivet shearing tool |
| NL125300C (cg-RX-API-DMAC7.html) | 1961-04-14 | |||
| US3423389A (en) | 1967-10-05 | 1969-01-21 | Arizona Chem | Rosin compounds of improved color and stability |
| US3780013A (en) | 1972-12-18 | 1973-12-18 | Arizona Chem | Preparation of color improved tall oil rosin pentaerythritol esters |
| US3959410A (en) | 1974-08-12 | 1976-05-25 | The Goodyear Tire & Rubber Company | Butadiene grafted ethylene-vinyl acetate hot melt adhesive |
| US4172070A (en) | 1978-03-27 | 1979-10-23 | Arizona Chemical Company | Oxygen-stable rosin-primary polyhydric aliphatic alcohol esters and a method for preparing the same utilizing arylsulfonic acid catalysis |
| JPS559605A (en) | 1978-06-23 | 1980-01-23 | Arakawa Chem Ind Co Ltd | Preparation of rosin ester having high softening point and improved stability |
| US4377510A (en) | 1981-11-30 | 1983-03-22 | Arizona Chemical Company | Urethane-modified rosin ester and process for preparing the same |
| US4380513A (en) | 1981-11-30 | 1983-04-19 | Arizona Chemical Company | Inert rosin esters and process for preparing the same |
| US4548746A (en) | 1984-05-14 | 1985-10-22 | Westvaco Corporation | Rosin pentaerythritol ester preparation improvement |
| US4585584A (en) | 1985-04-08 | 1986-04-29 | Union Camp Corporation | Process for preparing rosin esters of improved color |
| US4650607A (en) | 1985-05-09 | 1987-03-17 | Westvaco Corporation | Method for rosin esterification |
| US4657703A (en) | 1986-06-30 | 1987-04-14 | Hercules Incorporated | Method of improving the color of tall oil rosin esters |
| US4690783A (en) | 1986-08-29 | 1987-09-01 | Union Camp Corporation | Method of preparing rosin ester from polyol with phosphorous acid catalyst |
| US4788009A (en) | 1986-11-14 | 1988-11-29 | Union Camp Corporation | Method of preparing rosin esters of improved thermal stability with inorganic salt of phosphorous or hypophosphorous acid |
| US4693847A (en) | 1986-11-14 | 1987-09-15 | Union Camp Corporation | Method of preparing hot-melt stable rosin ester with organic ester of hypophosphorous acid catalyst |
| US4725384A (en) | 1986-11-17 | 1988-02-16 | Westvaco Corporation | Method for rosin esterification in the presence of phosphinic acid and phenol sulfide and subsequent neutralization with a magnesium salt |
| JP2539811B2 (ja) | 1987-01-29 | 1996-10-02 | 荒川化学工業株式会社 | ロジンエステルの製造法 |
| US5021548A (en) | 1990-01-22 | 1991-06-04 | Hercules Incorporated | Sodium hydroxymethane sulfonate to improve the color stability of rosin resins |
| US5036129A (en) | 1990-04-17 | 1991-07-30 | Great Lakes Chemical Corporation | Flame retardant hot melt adhesive compositions |
| US5049652A (en) | 1990-11-30 | 1991-09-17 | Hercules Incorporated | Use of a mixed catalyst system to improve the viscosity stability of rosin resins |
| DE69220045T2 (de) * | 1991-12-21 | 1997-09-11 | Arakawa Chem Ind | Verfahren zur herstellung von kolophoniumester und farblosem kolophonium |
| JP2795018B2 (ja) * | 1991-12-21 | 1998-09-10 | 荒川化学工業株式会社 | ロジンエステルの製造法 |
| US5543110A (en) | 1993-03-16 | 1996-08-06 | Westvaco Corporation | Tall oil deodorization process |
| JP3371985B2 (ja) | 1993-06-25 | 2003-01-27 | 荒川化学工業株式会社 | 無色ロジンエステルの製造法 |
| US5504152A (en) | 1995-01-10 | 1996-04-02 | Arizona Chemical Company | Esterification of rosin |
| CN1223644C (zh) | 2000-02-17 | 2005-10-19 | 阿克佐诺贝尔公司 | 聚酯增粘剂及粘合剂组合物 |
| JP4534258B2 (ja) * | 2007-09-28 | 2010-09-01 | 荒川化学工業株式会社 | 粘着付与剤、医療用貼布剤用粘着付与剤、粘着剤または接着剤組成物および医療用貼付剤用粘着剤 |
| JP5190668B2 (ja) * | 2007-12-28 | 2013-04-24 | 荒川化学工業株式会社 | 粘着付与剤、粘・接着剤組成物および粘・接着フィルムラベル |
| CN102348766A (zh) * | 2009-03-13 | 2012-02-08 | 荒川化学工业株式会社 | 树脂用改性剂、接合剂组合物和热塑性树脂组合物 |
| CN102369083B (zh) * | 2009-03-30 | 2014-08-20 | 荒川化学工业株式会社 | 用于无铅焊料的焊剂组合物和无铅焊料组合物 |
| US20110213120A1 (en) | 2010-03-01 | 2011-09-01 | Arizona Chemical Company | Rosin esters for non-woven applications, methods of making and using and products therefrom |
| JP5734779B2 (ja) * | 2010-12-24 | 2015-06-17 | 富士フイルム株式会社 | ポリエステル重合体、樹脂組成物、成形体、及びフィルム |
| WO2012141675A1 (en) * | 2011-04-11 | 2012-10-18 | Arizona Chemical Company, Llc | Rosin esters for non-wovens |
| JP2013058172A (ja) | 2011-09-09 | 2013-03-28 | Toshiba Corp | 映像収録再生装置、収録方法及び再構築方法 |
| WO2013090283A1 (en) * | 2011-12-12 | 2013-06-20 | Arizona Chemical Company, Llc | Rejuvenation of reclaimed asphalt |
| KR20140123952A (ko) * | 2012-01-28 | 2014-10-23 | 아라까와 가가꾸 고교 가부시끼가이샤 | 점착 부여제, 의료용 또는 공업용 점착 부여제, 의료용 또는 공업용 점·접착제, 의료용 또는 공업용 점·접착 시트, 및 의료용 또는 공업용 접착 테이프 |
| US20150018470A1 (en) | 2012-03-08 | 2015-01-15 | Arakawa Chemical Industries, Ltd. | Hot-melt adhesive composition |
| RU2543163C2 (ru) * | 2012-12-25 | 2015-02-27 | Аризона Кемикал Кампани, ЛЛК | Способ очистки канифоли |
| EP3049490B1 (en) * | 2013-09-27 | 2024-08-14 | Kraton Chemical, LLC | Rosin esters and compositions thereof |
-
2014
- 2014-09-26 CN CN201480057440.9A patent/CN105916949A/zh active Pending
- 2014-09-26 WO PCT/US2014/057674 patent/WO2015048415A2/en not_active Ceased
- 2014-09-26 US US15/025,081 patent/US10011740B2/en active Active
- 2014-09-26 KR KR1020167010634A patent/KR102366374B1/ko not_active Expired - Fee Related
- 2014-09-26 EP EP14790825.5A patent/EP3049491A2/en not_active Withdrawn
- 2014-09-26 JP JP2016518134A patent/JP6789812B2/ja active Active
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