JP2016528306A5 - - Google Patents
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- JP2016528306A5 JP2016528306A5 JP2016515021A JP2016515021A JP2016528306A5 JP 2016528306 A5 JP2016528306 A5 JP 2016528306A5 JP 2016515021 A JP2016515021 A JP 2016515021A JP 2016515021 A JP2016515021 A JP 2016515021A JP 2016528306 A5 JP2016528306 A5 JP 2016528306A5
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- thermoplastic
- oil
- block copolymer
- polymerizing
- 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.)
- Pending
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- 239000000178 monomer Substances 0.000 claims description 263
- 238000000034 method Methods 0.000 claims description 143
- 229920001169 thermoplastic Polymers 0.000 claims description 125
- 239000004416 thermosoftening plastic Substances 0.000 claims description 125
- 229920001400 block copolymer Polymers 0.000 claims description 93
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 71
- 230000000379 polymerizing effect Effects 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 59
- 239000012986 chain transfer agent Substances 0.000 claims description 54
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 52
- 239000008158 vegetable oil Substances 0.000 claims description 50
- 229920006301 statistical copolymer Polymers 0.000 claims description 45
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 45
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 44
- -1 dinitrile Chemical group 0.000 claims description 39
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 claims description 36
- 229920000642 polymer Polymers 0.000 claims description 34
- 239000010775 animal oil Substances 0.000 claims description 32
- 235000021388 linseed oil Nutrition 0.000 claims description 32
- 239000000944 linseed oil Substances 0.000 claims description 32
- 150000003254 radicals Chemical class 0.000 claims description 26
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 235000012424 soybean oil Nutrition 0.000 claims description 18
- 239000003549 soybean oil Substances 0.000 claims description 18
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 16
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 16
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 16
- 235000005687 corn oil Nutrition 0.000 claims description 16
- 239000002285 corn oil Substances 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 16
- 239000010426 asphalt Substances 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 150000001993 dienes Chemical class 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000002825 nitriles Chemical class 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- 230000021615 conjugation Effects 0.000 claims description 10
- 229920001971 elastomer Polymers 0.000 claims description 10
- 150000003626 triacylglycerols Chemical class 0.000 claims description 10
- 239000000806 elastomer Substances 0.000 claims description 9
- 229920001519 homopolymer Polymers 0.000 claims description 9
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 claims description 8
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 8
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 8
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 claims description 8
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 8
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 8
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000002441 reversible effect Effects 0.000 claims description 8
- 239000003607 modifier Substances 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- WHBAFXYJHSRBSV-UHFFFAOYSA-N 1-phenylethyl 2-phenylpropanedithioate Chemical compound CC(SC(=S)C(C)c1ccccc1)c1ccccc1 WHBAFXYJHSRBSV-UHFFFAOYSA-N 0.000 claims description 6
- QEZSTBGQYFCJCW-UHFFFAOYSA-N 1-phenylethyl benzenecarbodithioate Chemical group C=1C=CC=CC=1C(C)SC(=S)C1=CC=CC=C1 QEZSTBGQYFCJCW-UHFFFAOYSA-N 0.000 claims description 6
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 6
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 claims description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 6
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 claims description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 6
- 229920000359 diblock copolymer Polymers 0.000 claims description 6
- 239000012990 dithiocarbamate Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 claims description 6
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 229920000428 triblock copolymer Polymers 0.000 claims description 6
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 6
- 229960002415 trichloroethylene Drugs 0.000 claims description 6
- 239000012989 trithiocarbonate Substances 0.000 claims description 6
- 239000003981 vehicle Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012991 xanthate Substances 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 238000001879 gelation Methods 0.000 claims description 5
- 235000013311 vegetables Nutrition 0.000 claims description 5
- 239000012988 Dithioester Substances 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- LAKYXBYUROTWBI-UHFFFAOYSA-N bis(benzylsulfanyl)methanethione Chemical group C=1C=CC=CC=1CSC(=S)SCC1=CC=CC=C1 LAKYXBYUROTWBI-UHFFFAOYSA-N 0.000 claims description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920003247 engineering thermoplastic Polymers 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000005022 dithioester group Chemical group 0.000 claims 2
- 238000013467 fragmentation Methods 0.000 claims 2
- 238000006062 fragmentation reaction Methods 0.000 claims 2
- 238000012711 chain transfer polymerization Methods 0.000 claims 1
- 238000004581 coalescence Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 239000010773 plant oil Substances 0.000 claims 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims 1
- 230000003068 static effect Effects 0.000 claims 1
- 238000004073 vulcanization Methods 0.000 claims 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361825241P | 2013-05-20 | 2013-05-20 | |
| US61/825,241 | 2013-05-20 | ||
| PCT/US2014/038799 WO2014189939A2 (en) | 2013-05-20 | 2014-05-20 | Thermoplastic elastomers via reversible addition-fragmentation chain transfer polymerization of triglycerides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016528306A JP2016528306A (ja) | 2016-09-15 |
| JP2016528306A5 true JP2016528306A5 (enExample) | 2017-06-29 |
Family
ID=50983166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016515021A Pending JP2016528306A (ja) | 2013-05-20 | 2014-05-20 | トリグリセリドの可逆的付加開裂連鎖移動重合を介した熱可塑性エラストマー |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US9650463B2 (enExample) |
| EP (3) | EP3632942A1 (enExample) |
| JP (1) | JP2016528306A (enExample) |
| KR (1) | KR20160009583A (enExample) |
| CN (3) | CN105229045B (enExample) |
| AU (1) | AU2014268692B2 (enExample) |
| BR (2) | BR112015028368B1 (enExample) |
| CA (1) | CA2910680A1 (enExample) |
| CL (1) | CL2015003375A1 (enExample) |
| EA (1) | EA201592176A1 (enExample) |
| HK (1) | HK1220219A1 (enExample) |
| PH (1) | PH12015502467A1 (enExample) |
| SG (3) | SG10201606740QA (enExample) |
| WO (1) | WO2014189939A2 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015505339A (ja) | 2012-01-18 | 2015-02-19 | アイオワ、ステイト、ユニバーシティー、リサーチ、ファウンデーション、インコーポレイテッドＩｏｗａ Ｓｔａｔｅ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ｆｏｕｎｄａｔｉｏｎ，Ｉｎｃ． | 植物油の原子移動ラジカル重合による熱可塑性エラストマー |
| CN105229045B (zh) | 2013-05-20 | 2018-07-13 | 爱荷华州立大学研究基金会有限公司 | 经由甘油三酯的可逆加成-断裂链转移聚合的热塑性弹性体 |
| ES2811918T3 (es) * | 2015-02-09 | 2021-03-15 | Archer Daniels Midland Co | Macroiniciadores de aceites poliméricos derivados de fuentes renovables y copolímeros de bloque termoplásticos derivados de los mismos |
| BR112017018131B1 (pt) * | 2015-02-27 | 2022-10-25 | Cargill, Incorporated | Composições de rejuvenescimento para aplicações de asfalto e métodos de aplicação das mesmas |
| DE102015208810A1 (de) * | 2015-05-12 | 2016-11-17 | Continental Reifen Deutschland Gmbh | RAFT-Agens, Verfahren zur Polymerisation, Polymer und Kautschukmischung sowie deren Verwendung |
| HK1249897A1 (zh) * | 2015-06-02 | 2018-11-16 | 内斯托尔株式会社 | 新型甘油三酯及其用途 |
| US10323148B1 (en) | 2016-05-26 | 2019-06-18 | Marathon Petroleum Company Lp | Method of making an asphalt composition containing ester bottoms |
| CN106433158B (zh) * | 2016-07-07 | 2018-12-04 | 交通运输部科学研究院 | 改性生物沥青的制备方法和改性生物沥青及其用途 |
| US11072674B2 (en) | 2016-07-07 | 2021-07-27 | Iowa State University Research Foundation, Inc. | Multiblock copolymer and method of making thereof |
| WO2018009830A1 (en) | 2016-07-07 | 2018-01-11 | Iowa State University Research Foundation, Inc. | Thiocarbonylthio compounds as chain transfer agents suitable for raft polymerization |
| WO2018031373A1 (en) | 2016-08-12 | 2018-02-15 | Iowa State University Research Foundation, Inc. | Acrylated and acylated or acetalized polyol as a biobased substitute for hard, rigid thermoplastic and thermoplastic and thermoset materials |
| FR3058729A1 (fr) * | 2016-11-17 | 2018-05-18 | Compagnie Generale Des Etablissements Michelin | Pneumatique comprenant une bande de roulement comprenant un elastomere thermoplastique et un systeme de reticulation a base de soufre |
| FR3060588A1 (fr) * | 2016-12-20 | 2018-06-22 | Compagnie Generale Des Etablissements Michelin | Composition de caoutchouc comprenant une poudrette de caoutchouc specifique |
| WO2018183261A1 (en) * | 2017-03-27 | 2018-10-04 | Iowa State University Research Foundation, Inc. | Macro-raft chain transfer agents as anionic polymerization terminators |
| US10316192B2 (en) | 2017-08-25 | 2019-06-11 | Cargill, Incorporated | Emulsions with polymerized oils and methods of manufacturing the same |
| CN108084071B (zh) * | 2017-12-29 | 2019-11-22 | 云南铁峰矿业化工新技术有限公司 | 一种黄药真空制备装置 |
| CN108503276A (zh) * | 2018-04-20 | 2018-09-07 | 万玉梅 | 一种功能型路面养护材料及其制备方法 |
| EP3802714A4 (en) | 2018-06-11 | 2022-03-23 | Swimc Llc | PACKAGING COATING WITH WATER-DISPERSABLE ACRYLIC BLOCK COPOLYMER |
| CA3103339A1 (en) | 2018-06-18 | 2019-12-26 | Cornell University | Systems and methods for n-halamine-dopamine copolymers for high-performance, low-cost, and easy-to-apply antimicrobial coatings |
| CN109679001A (zh) * | 2018-12-29 | 2019-04-26 | 锦州英诺威科技服务有限公司 | 一种用于聚丙烯生产的杀活剂 |
| US11814506B2 (en) | 2019-07-02 | 2023-11-14 | Marathon Petroleum Company Lp | Modified asphalts with enhanced rheological properties and associated methods |
| CA3088894C (en) | 2020-05-21 | 2024-04-30 | Marathon Petroleum Company Lp | Systems and methods for venting asphalt transport tanks |
| CN112175555A (zh) * | 2020-09-29 | 2021-01-05 | 杭州英创新材料有限公司 | 一种极性热熔胶及其制备方法 |
| US20240199871A1 (en) * | 2021-04-02 | 2024-06-20 | Iowa State University Research Foundation, Inc. | Impact modification of polyesters via reactive extrusion with polyacrylated epoxidized high oleic soybean oil |
| CA3214142A1 (en) * | 2021-04-02 | 2022-10-06 | Iowa State University Research Foundation, Inc. | Thermoplastic graft elastomers via reactive compatibilization of polyacrylated epoxidized high oleic soybean oil and polydiene-containing copolymers |
| CN113214575B (zh) * | 2021-04-24 | 2022-03-25 | 温州市剑利鞋业有限公司 | 一种pvc鞋底及其制备工艺 |
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- 2014-05-20 CN CN201480029039.4A patent/CN105229045B/zh active Active
- 2014-05-20 WO PCT/US2014/038799 patent/WO2014189939A2/en not_active Ceased
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- 2014-05-20 BR BR112015028368-3A patent/BR112015028368B1/pt active IP Right Grant
- 2014-05-20 JP JP2016515021A patent/JP2016528306A/ja active Pending
- 2014-05-20 HK HK16108276.0A patent/HK1220219A1/zh unknown
- 2014-05-20 EA EA201592176A patent/EA201592176A1/ru unknown
- 2014-05-20 BR BR122017010545-0A patent/BR122017010545B1/pt active IP Right Grant
- 2014-05-20 EP EP14732720.9A patent/EP2999727B1/en active Active
- 2014-05-20 SG SG10201606740QA patent/SG10201606740QA/en unknown
- 2014-05-20 SG SG10201606742UA patent/SG10201606742UA/en unknown
- 2014-05-20 KR KR1020157034372A patent/KR20160009583A/ko not_active Withdrawn
- 2014-05-20 AU AU2014268692A patent/AU2014268692B2/en not_active Ceased
- 2014-05-20 SG SG11201509408UA patent/SG11201509408UA/en unknown
- 2014-05-20 CA CA2910680A patent/CA2910680A1/en not_active Abandoned
- 2014-05-20 EP EP18150507.4A patent/EP3327047A1/en not_active Withdrawn
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