KR20180123585A - 에폭시화 중합체의 제조방법 - Google Patents
에폭시화 중합체의 제조방법 Download PDFInfo
- Publication number
- KR20180123585A KR20180123585A KR1020187032146A KR20187032146A KR20180123585A KR 20180123585 A KR20180123585 A KR 20180123585A KR 1020187032146 A KR1020187032146 A KR 1020187032146A KR 20187032146 A KR20187032146 A KR 20187032146A KR 20180123585 A KR20180123585 A KR 20180123585A
- Authority
- KR
- South Korea
- Prior art keywords
- polymer
- solvent
- epoxidized
- acid
- epoxidation
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 58
- 229920000642 polymer Polymers 0.000 title claims description 98
- 230000008569 process Effects 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims abstract description 51
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 238000006735 epoxidation reaction Methods 0.000 claims description 54
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 38
- 244000043261 Hevea brasiliensis Species 0.000 claims description 27
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 26
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 25
- 229920003052 natural elastomer Polymers 0.000 claims description 24
- 229920001194 natural rubber Polymers 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 150000008065 acid anhydrides Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229920002857 polybutadiene Polymers 0.000 claims description 7
- 239000007800 oxidant agent Substances 0.000 claims description 6
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 5
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- 241001495453 Parthenium argentatum Species 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 229920005549 butyl rubber Polymers 0.000 claims description 2
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical group CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- MPRWIVBRDAXEAF-UHFFFAOYSA-N acetyloxy ethaneperoxoate Chemical compound CC(=O)OOOC(C)=O MPRWIVBRDAXEAF-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 abstract description 24
- 239000005060 rubber Substances 0.000 abstract description 24
- 239000000243 solution Substances 0.000 description 28
- 238000001556 precipitation Methods 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 229920002907 Guar gum Polymers 0.000 description 13
- 239000000665 guar gum Substances 0.000 description 13
- 229960002154 guar gum Drugs 0.000 description 13
- 235000010417 guar gum Nutrition 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- 150000004965 peroxy acids Chemical class 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003518 caustics Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 244000303965 Cyamopsis psoralioides Species 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZDPBCYYDJHTNKC-UHFFFAOYSA-M tetrahexylphosphanium;bromide Chemical compound [Br-].CCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC ZDPBCYYDJHTNKC-UHFFFAOYSA-M 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- -1 glycol ethers Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 150000004967 organic peroxy acids Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241001553700 Euphorbia lathyris Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 241000341871 Taraxacum kok-saghyz Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical class O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 2
- MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 1
- JAUFWTSSYRTLLB-UHFFFAOYSA-N (2-phenylacetyl) 2-phenylacetate Chemical compound C=1C=CC=CC=1CC(=O)OC(=O)CC1=CC=CC=C1 JAUFWTSSYRTLLB-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- LLNAMUJRIZIXHF-CLFYSBASSA-N (z)-2-methyl-3-phenylprop-2-en-1-ol Chemical compound OCC(/C)=C\C1=CC=CC=C1 LLNAMUJRIZIXHF-CLFYSBASSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- WRTPVONNQPWNRH-UHFFFAOYSA-N 2-methylbutanoyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OC(=O)C(C)CC WRTPVONNQPWNRH-UHFFFAOYSA-N 0.000 description 1
- RWNXHDBPCPMSIB-UHFFFAOYSA-N 2-methylheptanoyl 2-methylheptanoate Chemical compound CCCCCC(C)C(=O)OC(=O)C(C)CCCCC RWNXHDBPCPMSIB-UHFFFAOYSA-N 0.000 description 1
- KRFHNSRRDDKHDT-UHFFFAOYSA-N 2-methylhexanoyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OC(=O)C(C)CCCC KRFHNSRRDDKHDT-UHFFFAOYSA-N 0.000 description 1
- FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-UHFFFAOYSA-N 0.000 description 1
- ZIAYFIXXUWHMJK-UHFFFAOYSA-N 3-methylheptanoyl 3-methylheptanoate Chemical compound CCCCC(C)CC(=O)OC(=O)CC(C)CCCC ZIAYFIXXUWHMJK-UHFFFAOYSA-N 0.000 description 1
- GOFWIJQXYAFIQU-UHFFFAOYSA-N 3-methylhexanoyl 3-methylhexanoate Chemical compound CCCC(C)CC(=O)OC(=O)CC(C)CCC GOFWIJQXYAFIQU-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- SQAHPYZABTWPNY-UHFFFAOYSA-N 3-phenylpropanoyl 3-phenylpropanoate Chemical compound C=1C=CC=CC=1CCC(=O)OC(=O)CCC1=CC=CC=C1 SQAHPYZABTWPNY-UHFFFAOYSA-N 0.000 description 1
- FFDDUJMMWJAXCM-UHFFFAOYSA-N 4-methylheptanoyl 4-methylheptanoate Chemical compound CCCC(C)CCC(=O)OC(=O)CCC(C)CCC FFDDUJMMWJAXCM-UHFFFAOYSA-N 0.000 description 1
- URZYJMFUPBREMV-UHFFFAOYSA-N 4-methylpentanoyl 4-methylpentanoate Chemical compound CC(C)CCC(=O)OC(=O)CCC(C)C URZYJMFUPBREMV-UHFFFAOYSA-N 0.000 description 1
- MCOIUVKCUYNDSI-UHFFFAOYSA-N 5-methylheptanoyl 5-methylheptanoate Chemical compound CCC(C)CCCC(=O)OC(=O)CCCC(C)CC MCOIUVKCUYNDSI-UHFFFAOYSA-N 0.000 description 1
- YZFHKCLSTBDMOU-UHFFFAOYSA-N 5-methylhexanoyl 5-methylhexanoate Chemical compound CC(C)CCCC(=O)OC(=O)CCCC(C)C YZFHKCLSTBDMOU-UHFFFAOYSA-N 0.000 description 1
- IYIHDGMBQBUFFD-UHFFFAOYSA-N 6-methylheptanoyl 6-methylheptanoate Chemical compound CC(C)CCCCC(=O)OC(=O)CCCCC(C)C IYIHDGMBQBUFFD-UHFFFAOYSA-N 0.000 description 1
- 241000208327 Apocynaceae Species 0.000 description 1
- 241001071161 Asclepias Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000041806 Cacalia Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000703226 Campanula americana Species 0.000 description 1
- 241000703121 Campanula rotundifolia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001232416 Chrysothamnus Species 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241001232454 Ericameria nauseosa Species 0.000 description 1
- 229930185597 Euphorbia lathyris Natural products 0.000 description 1
- 238000006469 Jacobsen epoxidation reaction Methods 0.000 description 1
- 235000017396 Menta cendrata Nutrition 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241001003282 Parthenium incanum Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 241001062991 Pycnanthemum Species 0.000 description 1
- 244000178112 Pycnanthemum incanum Species 0.000 description 1
- 235000012230 Pycnanthemum incanum Nutrition 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 241000607059 Solidago Species 0.000 description 1
- 244000197975 Solidago virgaurea Species 0.000 description 1
- 235000000914 Solidago virgaurea Nutrition 0.000 description 1
- 241001154912 Teucrium canadense Species 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- VCAQPYXOWLIOSF-UHFFFAOYSA-N acetic acid;sulfuric acid;hydrate Chemical compound O.CC(O)=O.OS(O)(=O)=O VCAQPYXOWLIOSF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- VIXPKJNAOIWFMW-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC VIXPKJNAOIWFMW-UHFFFAOYSA-M 0.000 description 1
- ZCPCLAPUXMZUCD-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC ZCPCLAPUXMZUCD-UHFFFAOYSA-M 0.000 description 1
- BXNDLFLURPWBIQ-UHFFFAOYSA-N dihexadecyl(dimethyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC BXNDLFLURPWBIQ-UHFFFAOYSA-N 0.000 description 1
- BNEFASITZOQPGR-UHFFFAOYSA-M dihexadecyl(dimethyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCC BNEFASITZOQPGR-UHFFFAOYSA-M 0.000 description 1
- JASBPDANIMWRTN-UHFFFAOYSA-M dihexadecyl(dimethyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCC JASBPDANIMWRTN-UHFFFAOYSA-M 0.000 description 1
- DAXBPSOPGVTRCZ-UHFFFAOYSA-M dihexadecyl(dimethyl)phosphanium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCC DAXBPSOPGVTRCZ-UHFFFAOYSA-M 0.000 description 1
- XJCGBPXLSLTNNL-UHFFFAOYSA-N dihexadecyl(dimethyl)phosphanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCC XJCGBPXLSLTNNL-UHFFFAOYSA-N 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- PSLWZOIUBRXAQW-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC PSLWZOIUBRXAQW-UHFFFAOYSA-M 0.000 description 1
- DYJCDOZDBMRUEB-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;hydron;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC DYJCDOZDBMRUEB-UHFFFAOYSA-M 0.000 description 1
- NQFNJHBXAYBSPB-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC NQFNJHBXAYBSPB-UHFFFAOYSA-N 0.000 description 1
- NFJMQHQMUNKPJG-UHFFFAOYSA-M dimethyl(dioctadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCCCC NFJMQHQMUNKPJG-UHFFFAOYSA-M 0.000 description 1
- TVGVGEPYQMNCSO-UHFFFAOYSA-M dimethyl(dioctadecyl)phosphanium;hydron;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCCCC TVGVGEPYQMNCSO-UHFFFAOYSA-M 0.000 description 1
- MJGXVMIMPGVYOK-UHFFFAOYSA-N dimethyl(dioctadecyl)phosphanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCCCC[P+](C)(C)CCCCCCCCCCCCCCCCCC MJGXVMIMPGVYOK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- MWSPFHZPVVWJCO-UHFFFAOYSA-M hydron;methyl(trioctyl)azanium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC MWSPFHZPVVWJCO-UHFFFAOYSA-M 0.000 description 1
- RULHPTADXJPDSN-UHFFFAOYSA-M hydron;tetrahexylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC RULHPTADXJPDSN-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- QLPMKRZYJPNIRP-UHFFFAOYSA-M methyl(trioctyl)azanium;bromide Chemical compound [Br-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC QLPMKRZYJPNIRP-UHFFFAOYSA-M 0.000 description 1
- AMUCTDNDAXEAOW-UHFFFAOYSA-M methyl(trioctyl)azanium;iodide Chemical compound [I-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC AMUCTDNDAXEAOW-UHFFFAOYSA-M 0.000 description 1
- UEPYVEILIFKOAA-UHFFFAOYSA-N methyl(trioctyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC UEPYVEILIFKOAA-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229920006173 natural rubber latex Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Chemical group 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000026676 system process Effects 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- KUBXSUKJFAQDPV-UHFFFAOYSA-N tetrabutylphosphanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC KUBXSUKJFAQDPV-UHFFFAOYSA-N 0.000 description 1
- SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
- ODTSDWCGLRVBHJ-UHFFFAOYSA-M tetrahexylazanium;chloride Chemical compound [Cl-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC ODTSDWCGLRVBHJ-UHFFFAOYSA-M 0.000 description 1
- VRKHAMWCGMJAMI-UHFFFAOYSA-M tetrahexylazanium;iodide Chemical compound [I-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC VRKHAMWCGMJAMI-UHFFFAOYSA-M 0.000 description 1
- LHIGLAVLYYKORA-UHFFFAOYSA-N tetrahexylazanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC LHIGLAVLYYKORA-UHFFFAOYSA-N 0.000 description 1
- PJSMIDZMHMDOSX-UHFFFAOYSA-M tetrahexylphosphanium;chloride Chemical compound [Cl-].CCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PJSMIDZMHMDOSX-UHFFFAOYSA-M 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/04—Oxidation
- C08C19/06—Epoxidation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/08—Isoprene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Tires In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662318387P | 2016-04-05 | 2016-04-05 | |
| US62/318,387 | 2016-04-05 | ||
| PCT/US2017/025857 WO2017176686A1 (en) | 2016-04-05 | 2017-04-04 | Process for producing epoxidized polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180123585A true KR20180123585A (ko) | 2018-11-16 |
Family
ID=60000667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020187032146A Ceased KR20180123585A (ko) | 2016-04-05 | 2017-04-04 | 에폭시화 중합체의 제조방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10836841B2 (enExample) |
| EP (1) | EP3440116A4 (enExample) |
| JP (2) | JP2019513866A (enExample) |
| KR (1) | KR20180123585A (enExample) |
| CN (1) | CN108884185A (enExample) |
| CA (1) | CA3018778A1 (enExample) |
| MX (1) | MX2018012259A (enExample) |
| WO (1) | WO2017176686A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220029189A (ko) * | 2020-09-01 | 2022-03-08 | 김진국 | 에폭시화 고무의 제조방법 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12258427B2 (en) | 2018-12-21 | 2025-03-25 | Bridgestone Corporation | Processes for increasing the molecular weight of guayule natural rubber |
| US20230382007A1 (en) * | 2020-10-16 | 2023-11-30 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Particleboards including modified guayule resins/soy protein resin blends and associated methods for forming same |
| CN113072652B (zh) * | 2021-04-25 | 2022-06-28 | 岭南师范学院 | 一种定量环氧化天然橡胶及其制备方法 |
| CN116135887A (zh) * | 2021-11-17 | 2023-05-19 | 北京化工大学 | 一种环氧化橡胶的制备方法、环氧化橡胶及应用 |
| CN116162205B (zh) * | 2021-11-25 | 2025-09-16 | 北京化工大学 | 一种环氧化溶聚丁苯橡胶及其制备方法和应用 |
| CN116162296A (zh) * | 2021-11-25 | 2023-05-26 | 北京化工大学 | 一种高性能绿色轮胎的胎面材料及其制备方法和应用 |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3305515A (en) | 1964-05-06 | 1967-02-21 | Exxon Research Engineering Co | Solvent for polybutadiene rubber |
| US4219627A (en) | 1977-03-09 | 1980-08-26 | The Firestone Tire & Rubber Company | Process for the preparation of block copolymers |
| US5747598A (en) | 1990-01-16 | 1998-05-05 | Mobil Oil Corporation | Epoxidized solid elastomeric copolymers |
| US5034470A (en) * | 1990-09-04 | 1991-07-23 | The Goodyear Tire & Rubber Company | Process for the preparation of epoxidized synthetic cis-1,4-polyisoprene |
| US5399626A (en) | 1991-04-29 | 1995-03-21 | Shell Oil Company | Viscous conjugated diene block copolymers |
| US5310819A (en) | 1992-01-23 | 1994-05-10 | The United States Of America As Represented By The Secretary Of The Navy | Surface epoxidation of elastomers |
| DE69404740T2 (de) | 1993-05-13 | 1998-01-22 | Kao Corp | Verfahren zur Herstellung von Rohkautschuk |
| JP3722238B2 (ja) * | 1995-12-14 | 2005-11-30 | ダイセル化学工業株式会社 | エポキシ化有機系重合体の製造方法 |
| DE69615159T2 (de) * | 1995-12-14 | 2002-01-17 | Daicel Chemical Industries, Ltd. | Verfahren zur herstellung von epoxidiertem organischem polymer, thermoplastische harzzusammensetzung, primerzusammensetzung, nicht-vulkanisierte kautschukzusammensetzung, kautschukformmassen und verfahren zu deren herstellung |
| US5789512A (en) | 1996-12-23 | 1998-08-04 | Sartomer Company | Method for the epoxidation of unsaturated polymers |
| US6242536B1 (en) | 1997-12-11 | 2001-06-05 | Bridgestone Corporation | Process for preparation of block copolymers in mixed alkane/cycloalkane solvents |
| US6455655B1 (en) | 2000-09-28 | 2002-09-24 | The Goodyear Tire & Rubber Company | Emulsion styrene-butadiene rubber |
| CN1113906C (zh) * | 2000-10-29 | 2003-07-09 | 青岛化工学院 | 环氧化反式－1,4－聚异戊二烯的合成方法 |
| US6903164B2 (en) | 2000-11-13 | 2005-06-07 | Daicel Chemical Industries, Ltd. | Epoxidized thermoplastic polymers and processes for their production |
| WO2002092636A1 (en) * | 2001-05-14 | 2002-11-21 | Daicel Chemical Industries, Ltd. | Process for producing epoxidized diene polymer |
| US6716925B2 (en) | 2001-11-02 | 2004-04-06 | The Goodyear Tire & Rubber Company | Tire with a component made of a rubber composition comprised of a rubber having pendant hydroxyl groups and a rubber containing a nitrile moiety |
| US8519057B2 (en) * | 2007-06-01 | 2013-08-27 | Exxonmobil Chemical Patents Inc. | Impact modification and functionalization of copolymers of olefins and dienes |
| JP5654409B2 (ja) * | 2011-04-22 | 2015-01-14 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
| TWI426090B (zh) * | 2011-05-31 | 2014-02-11 | Tsrc Corp | 製造環氧化聚合物的方法 |
| WO2013111753A1 (ja) | 2012-01-23 | 2013-08-01 | 住友ゴム工業株式会社 | エポキシ化天然ゴムの製造方法、タイヤ用ゴム組成物及び空気入りタイヤ |
| JP5603363B2 (ja) | 2012-03-08 | 2014-10-08 | 住友ゴム工業株式会社 | エポキシ化天然ゴムの製造方法、タイヤ用ゴム組成物及び空気入りタイヤ |
| CN103130990B (zh) * | 2012-10-03 | 2015-02-18 | 大连理工大学 | 星形梳状聚乳酸及其制备方法 |
| EP2912027B1 (en) * | 2012-10-26 | 2019-09-11 | Blue Cube IP LLC | Novel epoxide compounds: 1,3-dioxiranylcyclopentane derivatives |
| CN103570848B (zh) * | 2013-10-24 | 2016-01-20 | 沈阳化工大学 | 环氧化天然杜仲胶的合成方法 |
| FR3017393B1 (fr) * | 2014-02-07 | 2016-02-12 | Michelin & Cie | Bande de roulement pour pneumatique a base de polyisoprene epoxyde |
| CN103910816B (zh) * | 2014-04-12 | 2016-06-15 | 青岛科技大学 | 一种改进的环氧化反式异戊橡胶制备方法 |
-
2017
- 2017-04-04 MX MX2018012259A patent/MX2018012259A/es unknown
- 2017-04-04 WO PCT/US2017/025857 patent/WO2017176686A1/en not_active Ceased
- 2017-04-04 KR KR1020187032146A patent/KR20180123585A/ko not_active Ceased
- 2017-04-04 CA CA3018778A patent/CA3018778A1/en active Pending
- 2017-04-04 EP EP17779622.4A patent/EP3440116A4/en not_active Withdrawn
- 2017-04-04 JP JP2018552830A patent/JP2019513866A/ja active Pending
- 2017-04-04 CN CN201780022017.9A patent/CN108884185A/zh active Pending
- 2017-04-04 US US16/091,431 patent/US10836841B2/en not_active Expired - Fee Related
-
2022
- 2022-01-28 JP JP2022012125A patent/JP2022068188A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220029189A (ko) * | 2020-09-01 | 2022-03-08 | 김진국 | 에폭시화 고무의 제조방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019513866A (ja) | 2019-05-30 |
| US20190127495A1 (en) | 2019-05-02 |
| WO2017176686A1 (en) | 2017-10-12 |
| JP2022068188A (ja) | 2022-05-09 |
| EP3440116A1 (en) | 2019-02-13 |
| CN108884185A (zh) | 2018-11-23 |
| EP3440116A4 (en) | 2019-12-18 |
| MX2018012259A (es) | 2019-02-07 |
| CA3018778A1 (en) | 2017-10-12 |
| US10836841B2 (en) | 2020-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20180123585A (ko) | 에폭시화 중합체의 제조방법 | |
| CA1197646A (en) | Process for modifying rubbers | |
| TWI450928B (zh) | 以共軛二烯為基質之奈米結構的聚合物 | |
| TWI564311B (zh) | 用來製備１，３－丁二烯及苯乙烯共聚物的方法及其在可硫化彈性體組成物中的用途 | |
| EP0498426B1 (en) | Hydrogenated block copolymers containing epoxy groups | |
| JP2665663B2 (ja) | 改質不飽和ポリエステルの製造方法 | |
| CN113336877B (zh) | 一种环氧化丁基橡胶的制备方法 | |
| EP0946600A1 (en) | Method for the epoxidation of unsaturated polymers | |
| CN104854177B (zh) | 用于制备环氧化聚合物的方法 | |
| JP2854891B2 (ja) | ハロゲン化水素化アクリロニトリルブタジエンゴム | |
| BR112020000244A2 (pt) | borracha de dieno ramificada em estrela | |
| RU2623274C2 (ru) | Способ эпоксидирования бутадиен-стирольного каучука | |
| JP3686370B2 (ja) | エポキシ化重合体の製造方法 | |
| JP6263526B2 (ja) | 官能化および分枝化されたエラストマー性コポリマーの調製方法 | |
| KR102566344B1 (ko) | 에폭시화된 폴리파르네센 및 이를 생산하기 위한 방법 | |
| CN112745460B (zh) | 一种饱和极性聚合物及其制备方法 | |
| JP3686381B2 (ja) | エポキシ化重合体の製造方法 | |
| Pejvak | Investigation of different degradation methods to prepare liquid epoxidized natural rubber for coating applications/Pejvak Rooshenass | |
| CN105778000B (zh) | 一种异戊橡胶接枝马来酸酐及其制备方法 | |
| SU199037A1 (enExample) | ||
| JPS60209854A (ja) | 親水性ポリマ−の製造方法 | |
| JP3487921B2 (ja) | エポキシ化ブロック共重合体 | |
| JPH052686B2 (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20181105 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20200403 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20210614 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20220208 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20210614 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |