WO2005003200A1 - Process for formation of preformed stabilizer polyols - Google Patents
Process for formation of preformed stabilizer polyols Download PDFInfo
- Publication number
- WO2005003200A1 WO2005003200A1 PCT/EP2004/005659 EP2004005659W WO2005003200A1 WO 2005003200 A1 WO2005003200 A1 WO 2005003200A1 EP 2004005659 W EP2004005659 W EP 2004005659W WO 2005003200 A1 WO2005003200 A1 WO 2005003200A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- macromer
- recited
- polyol
- weight
- preformed stabilizer
- Prior art date
Links
- 150000003077 polyols Chemical class 0.000 title claims abstract description 124
- 229920005862 polyol Polymers 0.000 title claims abstract description 123
- 239000003381 stabilizer Substances 0.000 title claims abstract description 74
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 33
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 52
- 239000000178 monomer Substances 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 27
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000003999 initiator Substances 0.000 claims description 24
- 239000002841 Lewis acid Substances 0.000 claims description 22
- 150000007517 lewis acids Chemical class 0.000 claims description 22
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 22
- -1 phosphate anion Chemical class 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052718 tin Inorganic materials 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 abstract description 26
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract description 4
- 230000002829 reductive effect Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 33
- 238000005755 formation reaction Methods 0.000 description 33
- 239000000047 product Substances 0.000 description 22
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000011968 lewis acid catalyst Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 238000010559 graft polymerization reaction Methods 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910052691 Erbium Inorganic materials 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052779 Neodymium Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical class [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 3
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical class [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KDFRADWZKMRRPJ-UHFFFAOYSA-N (4-methoxybenzoyl) 4-methoxybenzenecarboperoxoate Chemical compound C1=CC(OC)=CC=C1C(=O)OOC(=O)C1=CC=C(OC)C=C1 KDFRADWZKMRRPJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- WBSONQUHDWJABP-UHFFFAOYSA-N 2-ethoxybenzenethiol Chemical compound CCOC1=CC=CC=C1S WBSONQUHDWJABP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 235000010210 aluminium Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- ZZUKBDJWZXVOQG-UHFFFAOYSA-N ethyl 2,2,2-tribromoacetate Chemical compound CCOC(=O)C(Br)(Br)Br ZZUKBDJWZXVOQG-UHFFFAOYSA-N 0.000 description 2
- NIJGVVHCUXNSLL-UHFFFAOYSA-N ethyl 2,2-dibromoacetate Chemical compound CCOC(=O)C(Br)Br NIJGVVHCUXNSLL-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-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
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- XNJYRGMCZCPTJE-UHFFFAOYSA-N (1,2-dibromo-2-phenylethenyl)benzene Chemical compound C=1C=CC=CC=1C(Br)=C(Br)C1=CC=CC=C1 XNJYRGMCZCPTJE-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 1
- LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- AONKGGMHQHWMSM-UHFFFAOYSA-N 1,1,1-tribromopropane Chemical compound CCC(Br)(Br)Br AONKGGMHQHWMSM-UHFFFAOYSA-N 0.000 description 1
- ZUDLIFVTNPYZJH-UHFFFAOYSA-N 1,1,2,2-tetraphenylethylbenzene Chemical compound C1=CC=CC=C1C(C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 ZUDLIFVTNPYZJH-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- UNMYKPSSIFZORM-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)butane Chemical compound CCCCOCCOC=C UNMYKPSSIFZORM-UHFFFAOYSA-N 0.000 description 1
- UXKQGJYFPNFUJY-UHFFFAOYSA-N 1-(2-methylbutan-2-yldiazenyl)cyclohexane-1-carbonitrile Chemical compound CCC(C)(C)N=NC1(C#N)CCCCC1 UXKQGJYFPNFUJY-UHFFFAOYSA-N 0.000 description 1
- QKNQPCLQRXMWJO-UHFFFAOYSA-N 1-(tert-butyldiazenyl)cyclohexane-1-carbonitrile Chemical compound CC(C)(C)N=NC1(C#N)CCCCC1 QKNQPCLQRXMWJO-UHFFFAOYSA-N 0.000 description 1
- MOZHUOIQYVYEPN-UHFFFAOYSA-N 1-bromo-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(Br)C=C1 MOZHUOIQYVYEPN-UHFFFAOYSA-N 0.000 description 1
- SRXJYTZCORKVNA-UHFFFAOYSA-N 1-bromoethenylbenzene Chemical compound BrC(=C)C1=CC=CC=C1 SRXJYTZCORKVNA-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical class CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- CTXUTPWZJZHRJC-UHFFFAOYSA-N 1-ethenylpyrrole Chemical compound C=CN1C=CC=C1 CTXUTPWZJZHRJC-UHFFFAOYSA-N 0.000 description 1
- HQSMEHLVLOGBCK-UHFFFAOYSA-N 1-ethenylsulfinylethene Chemical compound C=CS(=O)C=C HQSMEHLVLOGBCK-UHFFFAOYSA-N 0.000 description 1
- BJEWLOAZFAGNPE-UHFFFAOYSA-N 1-ethenylsulfonylethane Chemical compound CCS(=O)(=O)C=C BJEWLOAZFAGNPE-UHFFFAOYSA-N 0.000 description 1
- KBIAVTUACPKPFJ-UHFFFAOYSA-N 1-ethynyl-4-methoxybenzene Chemical compound COC1=CC=C(C#C)C=C1 KBIAVTUACPKPFJ-UHFFFAOYSA-N 0.000 description 1
- GAZZTEJDUGESGQ-UHFFFAOYSA-N 1-ethynyl-4-nitrobenzene Chemical group [O-][N+](=O)C1=CC=C(C#C)C=C1 GAZZTEJDUGESGQ-UHFFFAOYSA-N 0.000 description 1
- YWBMNCRJFZGXJY-UHFFFAOYSA-N 1-hydroperoxy-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(OO)CCCC2=C1 YWBMNCRJFZGXJY-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- TURGQPDWYFJEDY-UHFFFAOYSA-N 1-hydroperoxypropane Chemical compound CCCOO TURGQPDWYFJEDY-UHFFFAOYSA-N 0.000 description 1
- KOCUMXQOUWPSLK-UHFFFAOYSA-N 1-methoxybuta-1,3-diene Chemical compound COC=CC=C KOCUMXQOUWPSLK-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- MFLLXRJTHGPGEB-UHFFFAOYSA-N 1-propylperoxypropane Chemical compound CCCOOCCC MFLLXRJTHGPGEB-UHFFFAOYSA-N 0.000 description 1
- GOAHRBQLKIZLKG-UHFFFAOYSA-N 1-tert-butylperoxybutane Chemical compound CCCCOOC(C)(C)C GOAHRBQLKIZLKG-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- 229940069744 2,2'-dithiobisbenzothiazole Drugs 0.000 description 1
- HHDUQHBAZZHUDC-UHFFFAOYSA-N 2,2,3,3-tetraphenylbutanedinitrile Chemical compound C=1C=CC=CC=1C(C(C#N)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C#N)C1=CC=CC=C1 HHDUQHBAZZHUDC-UHFFFAOYSA-N 0.000 description 1
- JHSWSKVODYPNDV-UHFFFAOYSA-N 2,2-bis(prop-2-enoxymethyl)propane-1,3-diol Chemical compound C=CCOCC(CO)(CO)COCC=C JHSWSKVODYPNDV-UHFFFAOYSA-N 0.000 description 1
- IAHOUQOWMXVMEH-UHFFFAOYSA-N 2,4,6-trinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IAHOUQOWMXVMEH-UHFFFAOYSA-N 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- DMAPDMJDXJDTQO-UHFFFAOYSA-N 2,4-diphenylpent-4-en-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C)CC(=C)C1=CC=CC=C1 DMAPDMJDXJDTQO-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 1
- MVJJKARWXLGDPQ-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)butanoic acid Chemical compound CCC(C(O)=O)SSCC(O)=O MVJJKARWXLGDPQ-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 description 1
- RFIMISVNSAUMBU-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC=C RFIMISVNSAUMBU-UHFFFAOYSA-N 0.000 description 1
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 1
- HSMAVZYQDXUJLK-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C)C HSMAVZYQDXUJLK-UHFFFAOYSA-N 0.000 description 1
- JZDHUYKBYNFYAB-UHFFFAOYSA-N 2-(tert-butyldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(C)C JZDHUYKBYNFYAB-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- YQDDREVIWHKACY-UHFFFAOYSA-N 2-amino-4-[(3-amino-4-carboxyphenyl)disulfanyl]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(SSC=2C=C(N)C(C(O)=O)=CC=2)=C1 YQDDREVIWHKACY-UHFFFAOYSA-N 0.000 description 1
- YMDXORWESGVYJW-UHFFFAOYSA-N 2-butan-2-ylperoxypropan-2-yl hydrogen carbonate Chemical compound CCC(C)OOC(C)(C)OC(O)=O YMDXORWESGVYJW-UHFFFAOYSA-N 0.000 description 1
- MENUHMSZHZBYMK-UHFFFAOYSA-N 2-cyclohexylethenylbenzene Chemical compound C1CCCCC1C=CC1=CC=CC=C1 MENUHMSZHZBYMK-UHFFFAOYSA-N 0.000 description 1
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- PKSZTVKEDWHDDO-UHFFFAOYSA-N 2-hydroperoxybutan-2-ylbenzene Chemical compound CCC(C)(OO)C1=CC=CC=C1 PKSZTVKEDWHDDO-UHFFFAOYSA-N 0.000 description 1
- SGJUFIMCHSLMRJ-UHFFFAOYSA-N 2-hydroperoxypropane Chemical compound CC(C)OO SGJUFIMCHSLMRJ-UHFFFAOYSA-N 0.000 description 1
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
- FMXDVBRYDYFVGS-UHFFFAOYSA-N 2-methoxy-1,3,5-trinitrobenzene Chemical compound COC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O FMXDVBRYDYFVGS-UHFFFAOYSA-N 0.000 description 1
- GXBCWRMJQPLZDU-UHFFFAOYSA-N 2-methyl-2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)(C)C GXBCWRMJQPLZDU-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 1
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- PIAOLBVUVDXHHL-UHFFFAOYSA-N 2-nitroethenylbenzene Chemical compound [O-][N+](=O)C=CC1=CC=CC=C1 PIAOLBVUVDXHHL-UHFFFAOYSA-N 0.000 description 1
- SAFZQLDSMLNONX-UHFFFAOYSA-N 2-phenoxyethenylbenzene Chemical compound C=1C=CC=CC=1OC=CC1=CC=CC=C1 SAFZQLDSMLNONX-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
- JZQHTTYHPIAPCZ-UHFFFAOYSA-N 2-prop-1-en-2-yloxirane Chemical compound CC(=C)C1CO1 JZQHTTYHPIAPCZ-UHFFFAOYSA-N 0.000 description 1
- IGDCJKDZZUALAO-UHFFFAOYSA-N 2-prop-2-enoxypropane-1,3-diol Chemical compound OCC(CO)OCC=C IGDCJKDZZUALAO-UHFFFAOYSA-N 0.000 description 1
- NFPBWZOKGZKYRE-UHFFFAOYSA-N 2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)C NFPBWZOKGZKYRE-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
- HLHNOIAOWQFNGW-UHFFFAOYSA-N 3-bromo-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C=C1Br HLHNOIAOWQFNGW-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
- AIMDYNJRXHEXEL-UHFFFAOYSA-N 3-phenylprop-1-enylbenzene Chemical compound C=1C=CC=CC=1CC=CC1=CC=CC=C1 AIMDYNJRXHEXEL-UHFFFAOYSA-N 0.000 description 1
- LRQDMMVZKMBBQC-UHFFFAOYSA-N 3-phosphanylpropanenitrile Chemical compound PCCC#N LRQDMMVZKMBBQC-UHFFFAOYSA-N 0.000 description 1
- CQHADWBXOMARTO-UHFFFAOYSA-N 3-prop-1-enyloxolane-2,5-dione Chemical compound CC=CC1CC(=O)OC1=O CQHADWBXOMARTO-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- QILKKAFYAFEWGU-UHFFFAOYSA-N 4-(cyanomethyl)benzonitrile Chemical compound N#CCC1=CC=C(C#N)C=C1 QILKKAFYAFEWGU-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- AEOUXVZAAKMFQW-UHFFFAOYSA-N 4-[(4-cyano-2-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound N#CC(C)CC(C)(C)N=NC(C)(C)CC(C)C#N AEOUXVZAAKMFQW-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- MGYMHQJELJYRQS-UHFFFAOYSA-N Ascaridole Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 235000014755 Eruca sativa Nutrition 0.000 description 1
- 244000024675 Eruca sativa Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- VPIAKHNXCOTPAY-UHFFFAOYSA-N Heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 1
- 229920001908 Hydrogenated starch hydrolysate Polymers 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- BQMQLJQPTQPEOV-UHFFFAOYSA-N OP(=O)OC=C Chemical class OP(=O)OC=C BQMQLJQPTQPEOV-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- VJDDQSBNUHLBTD-GGWOSOGESA-N [(e)-but-2-enoyl] (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(=O)\C=C\C VJDDQSBNUHLBTD-GGWOSOGESA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- ILNQBWPWHQSSNX-UHFFFAOYSA-N [hydroperoxy(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OO)C1=CC=CC=C1 ILNQBWPWHQSSNX-UHFFFAOYSA-N 0.000 description 1
- QFISYKBJJWTOOD-UHFFFAOYSA-N [hydroperoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OO)C1=CC=CC=C1 QFISYKBJJWTOOD-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- MGYMHQJELJYRQS-ZJUUUORDSA-N ascaridole Natural products C1C[C@]2(C)OO[C@@]1(C(C)C)C=C2 MGYMHQJELJYRQS-ZJUUUORDSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JZOIZKBKSZMVRV-UHFFFAOYSA-N benzo(a)triphenylene Chemical compound C1=CC=CC2=C3C4=CC=CC=C4C=CC3=C(C=CC=C3)C3=C21 JZOIZKBKSZMVRV-UHFFFAOYSA-N 0.000 description 1
- GBROPGWFBFCKAG-UHFFFAOYSA-N benzochrysene Natural products C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- FFFMSANAQQVUJA-UHFFFAOYSA-N but-1-ynylbenzene Chemical compound CCC#CC1=CC=CC=C1 FFFMSANAQQVUJA-UHFFFAOYSA-N 0.000 description 1
- ITMIAZBRRZANGB-UHFFFAOYSA-N but-3-ene-1,2-diol Chemical compound OCC(O)C=C ITMIAZBRRZANGB-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- ADKBGLXGTKOWIU-UHFFFAOYSA-N butanediperoxoic acid Chemical compound OOC(=O)CCC(=O)OO ADKBGLXGTKOWIU-UHFFFAOYSA-N 0.000 description 1
- IWTBWSGPDGPTIB-UHFFFAOYSA-N butanoyl butaneperoxoate Chemical compound CCCC(=O)OOC(=O)CCC IWTBWSGPDGPTIB-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 description 1
- QSHZUFRQHSINTB-UHFFFAOYSA-L dibutyltin(2+);dibromide Chemical compound CCCC[Sn](Br)(Br)CCCC QSHZUFRQHSINTB-UHFFFAOYSA-L 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- ISXUHJXWYNONDI-UHFFFAOYSA-L dichloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](Cl)(Cl)C1=CC=CC=C1 ISXUHJXWYNONDI-UHFFFAOYSA-L 0.000 description 1
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- JBVOSZYUSFDYIN-UHFFFAOYSA-N dimethyl cyclopropane-1,2-dicarboxylate Chemical compound COC(=O)C1CC1C(=O)OC JBVOSZYUSFDYIN-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- SDTDHTCWRNVNAJ-UHFFFAOYSA-L dimethyltin(2+);diacetate Chemical compound CC(=O)O[Sn](C)(C)OC(C)=O SDTDHTCWRNVNAJ-UHFFFAOYSA-L 0.000 description 1
- DOHQOGRRQASQAR-UHFFFAOYSA-L dimethyltin(2+);dibromide Chemical compound C[Sn](C)(Br)Br DOHQOGRRQASQAR-UHFFFAOYSA-L 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- XSVCYDUEICANRJ-UHFFFAOYSA-K dysprosium(3+);trifluoromethanesulfonate Chemical compound [Dy+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F XSVCYDUEICANRJ-UHFFFAOYSA-K 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- GLQOFBCJADYRKR-UHFFFAOYSA-K erbium(3+);trifluoromethanesulfonate Chemical compound [Er+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F GLQOFBCJADYRKR-UHFFFAOYSA-K 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- AFIQVBFAKUPHOA-UHFFFAOYSA-N ethenyl 2-methoxyacetate Chemical compound COCC(=O)OC=C AFIQVBFAKUPHOA-UHFFFAOYSA-N 0.000 description 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 description 1
- ZFGRMLYEKGWOAC-UHFFFAOYSA-N ethyl 2,3,4-trinitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O ZFGRMLYEKGWOAC-UHFFFAOYSA-N 0.000 description 1
- YBIALGDLTMTDFX-UHFFFAOYSA-N ethyl 4-ethylperoxycarbonylbenzoate Chemical compound CCOOC(=O)C1=CC=C(C(=O)OCC)C=C1 YBIALGDLTMTDFX-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- TWNOVENTEPVGEJ-UHFFFAOYSA-K europium(3+);trifluoromethanesulfonate Chemical compound [Eu+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F TWNOVENTEPVGEJ-UHFFFAOYSA-K 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- SRVXDMYFQIODQI-UHFFFAOYSA-K gallium(iii) bromide Chemical compound Br[Ga](Br)Br SRVXDMYFQIODQI-UHFFFAOYSA-K 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
- DBPDCYACEYLEMY-UHFFFAOYSA-K holmium(3+);trifluoromethanesulfonate Chemical compound [Ho+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DBPDCYACEYLEMY-UHFFFAOYSA-K 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical class [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- WGJJZRVGLPOKQT-UHFFFAOYSA-K lanthanum(3+);trifluoromethanesulfonate Chemical compound [La+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WGJJZRVGLPOKQT-UHFFFAOYSA-K 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical class OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NUMHUJZXKZKUBN-UHFFFAOYSA-N methyl 4-ethenylbenzoate Chemical compound COC(=O)C1=CC=C(C=C)C=C1 NUMHUJZXKZKUBN-UHFFFAOYSA-N 0.000 description 1
- OIGSXRLVIQGTAV-UHFFFAOYSA-N methyl ethenesulfonate Chemical compound COS(=O)(=O)C=C OIGSXRLVIQGTAV-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 229940102838 methylmethacrylate Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- MIVGZOMJVVQBAO-UHFFFAOYSA-N n,n-dibenzylprop-2-enamide Chemical compound C=1C=CC=CC=1CN(C(=O)C=C)CC1=CC=CC=C1 MIVGZOMJVVQBAO-UHFFFAOYSA-N 0.000 description 1
- SDYRIBONPHEWCT-UHFFFAOYSA-N n,n-dimethyl-2-phenylethenamine Chemical compound CN(C)C=CC1=CC=CC=C1 SDYRIBONPHEWCT-UHFFFAOYSA-N 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- DDTRTGHABFCXDF-UHFFFAOYSA-N n-formyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC=O DDTRTGHABFCXDF-UHFFFAOYSA-N 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- WYRSPTDNOIZOGA-UHFFFAOYSA-K neodymium(3+);trifluoromethanesulfonate Chemical compound [Nd+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F WYRSPTDNOIZOGA-UHFFFAOYSA-K 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- BZXFEMZFRLXGCY-UHFFFAOYSA-N octane-2-thiol Chemical compound CCCCCCC(C)S BZXFEMZFRLXGCY-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- VPPWQRIBARKZNY-UHFFFAOYSA-N oxo(diphenyl)tin Chemical compound C=1C=CC=CC=1[Sn](=O)C1=CC=CC=C1 VPPWQRIBARKZNY-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical class [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- ROUBZIWQWFQCHU-UHFFFAOYSA-K praseodymium(3+);trifluoromethanesulfonate Chemical compound [Pr+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F ROUBZIWQWFQCHU-UHFFFAOYSA-K 0.000 description 1
- LSMSJHJAFDRFSC-UHFFFAOYSA-N prop-2-enoyl but-2-enoate Chemical compound CC=CC(=O)OC(=O)C=C LSMSJHJAFDRFSC-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DDCWGUIPLGMBPO-UHFFFAOYSA-K samarium(3+);trifluoromethanesulfonate Chemical compound [Sm+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DDCWGUIPLGMBPO-UHFFFAOYSA-K 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical class [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- JLYAVYSVLLIWEK-UHFFFAOYSA-K terbium(3+);trifluoromethanesulfonate Chemical compound [Tb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JLYAVYSVLLIWEK-UHFFFAOYSA-K 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- VCZQFJFZMMALHB-UHFFFAOYSA-N tetraethylsilane Chemical compound CC[Si](CC)(CC)CC VCZQFJFZMMALHB-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VJDDQSBNUHLBTD-UHFFFAOYSA-N trans-crotonic acid-anhydride Natural products CC=CC(=O)OC(=O)C=CC VJDDQSBNUHLBTD-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-decalin Chemical compound C1CCC[C@@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-MGCOHNPYSA-N 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical class [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
- C08F290/142—Polyethers
Definitions
- Ihis4ft er4iorijelates ⁇ e ⁇ r ⁇ rally ⁇ and, more particularly, to a process for preparing a transesterification stable preformed stabilizer for use in the 15 formation of polymer poiyols.
- Polymer poiyols also know as graft poiyols, are well know in polyurethane chemistry. They find special use in the formation of certain foams with special properties. Typically, graft poiyols are formed as the reaction product of ethylenically unsaturated
- the typical macromers are polyether poiyols having induced unsaturation prepared by reacting any conventional polyol with an organic compound having both ethylenic unsaturation and a carboxyl, anhydride, isocyanate, epoxy, or other group reactive with an active hydrogen-containing group.
- Suitable unsaturated isocyanates include compounds such as isocyanatoethylmethacrylate (IEM) and 1,1 -dimethyl meta-isopropenyl
- Macromers 35 benzyl isocyanate (TMI). Macromers are usually prepared in the presence of a Lewis acid catalyst.
- the preformed stabilizers of the present invention which are also graft poiyols, are prepared by reaction of ethylenically unsaturated monomers with the macromer in the 0 presence of a carrier polyol, a reaction moderator, and a free radical polymerization initiator.
- a carrier polyol ethylenically unsaturated monomers
- a reaction moderator ethylenically unsaturated monomers
- a free radical polymerization initiator ethylenically unsaturated monomers
- One problem associated with this reaction is the tendency to have formation of transesterification products between the macromer and the carrier polyol wherein the unsaturated group on the macromer gets transferred to the carrier polyol.
- This transesterification product can then cause problems in the subsequent graft polyol formation reaction using the preformed stabilizer.
- this invention provides a preformed stabilizer comprising the reaction product of: a Lewis acid catalyzed macromer; and at least one ethylenically unsaturated monomer; wherein the macromer and the monomer are polymerized in the presence of at least one free radical initiator, a carrier polyol, and at least one phosphorous compound.
- the present invention is a method for formation of a preformed stabilizer comprising the steps of: providing a Lewis acid catalyzed macromer; providing at least one ethylenically unsaturated monomer; and polymerizing the macromer and the monomer in the presence of at least one free radical initiator, a carrier polyol, and at least one phosphorous compound.
- the present invention is a final graft polyol comprising the reaction product of: a Lewis acid catalyzed macromer; and at least one ethylenically unsaturated monomer; wherein the macromer and the monomer are polymerized in the presence of at least one free radical initiator, a carrier polyol, and at least one phosphorous compound.
- the present invention is a method for formation of a final graft polyol comprising the steps of: providing a Lewis acid catalyzed macromer; providing at least one ethylenically unsaturated monomer; and polymerizing the macromer and the monomer in the presence of at least one free radical initiator, a carrier polyol, and at least one phosphorous compound.
- Figure 1 is a comparison overlay of Gel Permeation Chromatography chromatograms of a mixture of a macromer and a carrier polyol heated to 130°C in the presence or absence of phosphoric acid;
- Figure 2 is a comparison overlay of Gel Permeation Chromatography chromatograms of a preformed stabilizer prepared using a macromer either having or not having phosphoric acid;
- Figure 3 is a comparison overlay of Gel Permeation Chromatography chromatograms of a preformed stabilizer prepared in the presence or absence of a phosphoric acid reactor charge;
- Figure 4 is a Gel Permeation Chromatography chromatogram of a macromer showing the presence of a carrier polyol transesterification product
- Figure 5 is a Gel Permeation Chromatography chromatogram of a macromer showing the presence of a carrier polyol transesterification product
- Figure 6 is a Gel Permeation Chromatography chromatogram of a macromer showing the presence of a carrier polyol transesterification product
- Figure 7 is a Gel Permeation Chromatography chromatogram of a macromer showing the presence of a carrier polyol transesterification product.
- polyether poiyols are well known, for example, by the base catalyzed addition of alkylene oxides to an initiator molecule or nucleus containing reactive hydrogens such as a polyhydric alcohol.
- polyhydric alcohol initiators include: glycerol, 1,1,1-trimethylolpropane, 1,1,1-trimethylolethane, 1 ,2,6-hexanetriol, pentaerythritol, sucrose, and sorbitol.
- Suitable initiators include both aliphatics and aromatics, such as, ethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, 1 ,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,2- pentanediol, 1 ,4-pentanediol, 1 ,5-pentanediol, 1 ,6-hexanedioI, 1 ,7-heptanediol.
- polyhydric alcohol compounds derived from phenol such as 2,2-bis(4-hydroxyphenyl)propane, commonly known as Bisphenol A.
- Suitable initiators for the polyether poiyols of the present invention comprise hydrogenated starch hydrolysates, such as those available from Roquette under the tradename Lyca- sin®, which are derivatives of maltitol.
- the polyether poiyols may be prepared by any known process such as, for example, the process disclosed by Wurtz in 1859, Encyclopedia of Chemical Technology. Vol. 7, pp. 257-262, published by Interscience Publishers, Inc. (1951) or in U.S. Patent No. 1,922,459.
- alkylene oxides examples include ethylene oxide, propylene oxide, butylene oxide, amylene oxide, tetrahydrofurans, epihalohydrins, arylalkylene styrene, and mixtures thereof.
- the alkylene oxides are added onto the initiator molecule and chain propagation is carried out in the presence of catalysts by either anionic polymerization or by cationic polymerization.
- the preferred alkoxylation catalysts are potassium hydroxide, sodium hydroxide, alco- holates of potassium hydroxide, alcoholates of sodium hydroxide, cesium hydroxide, amines, Lewis acid catalysts, or double metal complex catalysts, all of which are known in the art.
- Graft poiyols are generally defined as vinyl polymer dispersions in polyether poiyols as disclosed generally in U.S. Reissue Number Re. 33,291. Methods for the formation of typical graft poiyols are known in the art. In the prior art graft poiyols are typically prepared by the in situ polymerization of a polyether polyol having induced unsaturation, commonly known as a macromer, and an ethylenically unsaturated monomer or a mixture of ethylenically unsaturated monomers in the presence of a carrier polyol, a reaction moderator, optionally a preformed stabilizer, and a free radical polymerization initiator.
- a polyether polyol having induced unsaturation commonly known as a macromer
- an ethylenically unsaturated monomer or a mixture of ethylenically unsaturated monomers in the presence of a carrier polyol, a reaction moderator, optional
- the macromers have induced unsaturation levels of between about 0.1 and 1 mole per mole of polyol.
- macromer means a polyether polyol having induced unsaturation.
- the macromers employed in preparing the preformed stabilizer and the final graft polyol according to the present invention may be prepared by the reaction of any conventional polyol, described above, with an organic compound having both ethylenic unsaturation and a carboxyl, anhydride, isocyanate, epoxy, or other group reactive with an active hydrogen-containing group in the presence of a Lewis acid catalyst.
- Suitable unsaturated isocyanates include compounds such as isocyanatoethylmethacrylate (IEM) and 1,1 -dimethyl meta-isopropenyi benzyl isocyanate (TMI).
- organic compounds having ethylenic unsaturation and a reactive group include: maleic acid and anhydride, fumaric acid, crotonic acid and anhydride, propenyl succinic anhydride, acrylic acid, acryloyl chloride, hydroxyethyl aery I ate or methacrylate, hydroxypropyl acrylate or methacrylate, halogenated maleic acids and anhydrides, unsaturated polyhydric alcohols such as 2-butene-1 ,4-diol, glycerol allyl ether, trimethylolpropane allyl ether, pentaerythritol allyl ether, pentaerythritol vinyl e- ther, pentaerythritol diallyl ether, and 1-butene-3,4-diol, unsaturated epoxides such as 1-vinylcyclohexene-3,4,epoxide, butadiene monoxid
- isocyanates such as isocyanatoethylmethacrylate (IEM) and 1,1 -dimethyl meta- isopropenyl benzyl isocyanate (TMI).
- IEM isocyanatoethylmethacrylate
- TMI 1,1 -dimethyl meta- isopropenyl benzyl isocyanate
- a polycarboxylic acid or anhydride is employed to incorporate unsaturation into the poiyols, it is preferable to react the unsaturated polyol with an alkylene oxide, preferably ethylene or propylene oxide, to remove the unreacted acid groups prior to employment as a macromer in the present invention.
- the amount of alkylene oxide employed is such as to reduce the acid number of the unsaturated polyol to about 5 or less.
- a reactor is charged with the desired conventional polyol and Lewis acid catalyst at a temperature of from 20 to 40 °C.
- the amount of Lewis acid catalyst ranges from 0.2 to 50 parts per million (ppm), preferably from 0.5 to 25 ppm, most preferably from 1 to 15 ppm.
- the mixture is then hea- ted to a temperature of from 70 to 130 °C and the organic compound having ethylenic unsaturation and a reactive group is added over 0.5 to 1 hours to the reactor. The contents are held there for 1 to 3 hours.
- the formed macromer is then used in the reaction for formation of the preformed stabilizer or final graft polyol as described below.
- the suitable Lewis acid catalysts generally comprise tin-based, boron-based, alumi- num-based, gallium-based, rare earth-based, zinc-based, or titanium-based compounds.
- Representative tin-based compounds include: Dibutyltin diacetate, Dibutyltin dibromide, Dibutyltin dichloride, Dibutyltin dilaurate, Dibutyltin dimethoxide, Dibutyltin oxide, Dimethyltin diacetate, Dimethyltin dibromide, Diphenyltin dichloride, Diphenyltin oxide, Methyltin trichloride, Phenyltin trichloride, Tin(IV) acetate, Tin(IV) bromide, Tin(IV) chloride, Tin(IV) iodide, Tin(ll) oxide, Tin(ll) acetate, Tin(ll) bromide, Tin(ll) chloride, Tin(ll) iodide
- Representative boron-based compounds include: Boron tribromide, Boron trichloride, Boron trifluoride, and tris(pentafluorophenyl)borane.
- Representative aluminum-based compounds include: Aluminum chloride and Aluminum bromide.
- Representative gallium-based com- pounds include: Gallium chloride, Gallium bromide, and Gallium(lll) actylacetonate.
- Representative rare earth catalysts are generally salts of Scandium, Yttrium, Lanthanum, Praseodymium, Neodymium, Erbium, Thulium, Ytterbium, Neodymium or Luteti- um.
- Examples include: Ytterbium triflate, Ytterbium(lll) actylacetonate, Erbium(lll) trifluorosulfonate (erbium triflate), Erbium(lll) actylacetonate, Holmium triflate, Terbium triflate, Europium triflate, Europium(lll) trifluroacetate, Samarium triflate, Neodymium triflate, Neodymium(lll) actylacetonate, Praseodymium triflate, Lanthanum triflate, and Dysprosium triflate.
- Representative zinc-based compounds include Zinc chloride and Zinc bromide.
- titanium compounds include Titanium(IV) bromide and Titanium(IV) chloride.
- the preformed stabilizer of the present invention is formed by reacting ethylenically unsaturated monomers with a macromer in the presence of a carrier polyol, a free radical initiator, and optionally a reaction moderator.
- ethylenically unsaturated monomers which may be employed in preparing the preformed stabilizer or graft poiyols of the present invention include: butadiene, isoprene, 1 ,4-pentadiene, 1 ,6-hexadiene, 1 ,7-octadiene, styrene, alpha-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 2,4-dimethylstyrene, ethylstyrene, isopropylstyrene, butylstyrene, phenylstyrene, cyclohexylstyrene, benzylstyrene, and the like; substituted styrenes such as cyanostyrene, nitrostyrene, N,N- dimethylaminostyrene, acetoxystyrene,
- the mo- nomer comprises acrylonitrile, styrene, or a mixture thereof.
- the mixture comprises from 20 to 80% acrylonitrile with the remainder comprising styrene.
- the amount of ethylenically unsaturated monomers employed in the graft polymerization reaction for the preformed stabilizer is generally from 3 to 15% by weight, based on the total weight of the product; preferably from 5 to 10 percent by weight monomers.
- the amount of ethylenically unsaturated monomers employed in the graft polymeriza- tion reactions for a final graft polyol is generally from 25 to 70% by weight, based on the total weight of the product; preferably from 40 to 55 percent by weight monomers.
- Free radical polymerization initiators that may be used include the well-known free radical polymerization initiators such as the peroxides, persulfates, perborates, percar- bonates, azo compounds, etc. These include hydrogen peroxide, dibenzyoyl peroxide, acetyl peroxide, benzoyl hydroperoxide, t-butyl hydroperoxide, di-t-butyl peroxide, lauroyl peroxide, butyryl peroxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide, paramenthane hydroperoxide, diacetyl peroxide, di-alpha-cumyl peroxide, dipropyl peroxide, diisopropyl peroxide, isopropyl-t-butyl peroxide, butyl-t-butyl peroxide, difuroyl peroxide, bis (triphenylmethyl) peroxide, bis(p-methoxybenzo
- the graft polymerization reaction for formation of the preformed stabilizer will employ from about 0.1 weight percent to about 10 weight percent of a free radical polymerization initiator based on the total weight of the monomers utilized.
- the graft polymerization reaction for formation of the final graft polyol will generally employ from about 0.1 to about 3 weight percent and more preferably from about 0.3 to 1 weight percent of a free radical polymerization initiator based on the total weight of the mono- mers utilized.
- reaction moderator is preferably an alcohol, mercaptan, a haloalkane, or mixtures thereof.
- the reaction moderators which may be employed are the following: acetic acid, bromoacetic acid, chloroacetic acid, ethyl dibromoacetate, iodoacetic acid, tribromoacetic acid, ethyl tribromoacetate, tri- chloroacetic acid, ethyl trichloroacetate, acetone, p-bromophenylacetonitrile, p- nitrophenylacetylene, allyl alcohol, 2,4,6-trinitroaniline, p-ethynylanisole, 2,4,6- trinitroanisole, azobenzene, benzaldehyde, p-cyanobenzaldehyde, 2-butylbenzene
- the carrier polyol used to form either the preformed stabilizer or the final graft polyol according to the present invention may comprise any conventional polyol described above.
- the carrier polyol used in the formation of the preformed stabilizer and the final graft polyol need not be the same; however, they can be the same.
- the carrier polyol may comprise initiator plus propylene oxide with an ethylene oxide cap of from 0 to 30 percent by weight.
- the carrier polyol can comprise an initiator plus a he- teric mixture of alkylene oxides with or without an ethylene oxide or propylene oxide cap.
- the characteristics of the desired carrier polyol are in part determined by the de- sired properties of the foam to be prepared using the graft polyol.
- the amount of carrier polyol in the formula ranges from 50 to 90 percent by weight, with about 60 to 75 percent by weight more preferred and approximately 68 weight percent most preferred.
- the amount of carrier polyol used in the reaction for formation of the preformed stabilizer based on the total amount of carrier polyol used in the whole process generally ranges from 1 to 10% by weight.
- the preformed stabilizer is made in a reactor under an inert atmosphere by a semi-batch process. A free radical polymerization of ethylenically unsaturated monomers in the presence of the macromer, a free radical initiator, a carrier polyol, and optionally a reaction modifier is carried out.
- the reaction is run at a temperature of from 90 to 140 °C, with a preferred temperature of 110 to 130 °C.
- some of the carrier polyol some or none of the reaction modifier, and all of the macromer are charged to the reactor, agitated and heated to 110 to 130 °C.
- the amount of macromer used based on the total weight of macromer and carrier polyol in this reactor ranges from 24 to 28% by weight.
- the unsaturated monomers and any remaining reaction modifier are charged to a monomer feed tank while the remainder of the carrier polyol and the free radical initiator are charged to a polyol feed tank.
- the preformed stabilizer can be stored in the unstripped state for use in the formation of a final graft polyol.
- the preformed stabilizer is stripped prior to use in formation of a final graft polyol.
- the final calculated solids content in the preformed stabilizer is from about 5 to 20% by weight; more preferred between 10 and 15 % by weight, most preferred is about 14% by weight.
- the final graft polyol is the same as described for the preformed stabilizer above. However, the amount of monomers used is higher to achieve the desired solids content for a final graft polyol.
- the final calculated solids content in final graft poiyols is generally from about 25 to 70% by weight; more preferred between 30 and 60 % by weight, most preferred is from about 40 to 55% by weight.
- the preformed stabilizer described above may be used in formation of the final graft polyol, in which case the preformed stabilizer generally replaces the macromer used as a reactant in the process described above.
- the benefits of using a preformed stabilizer is well known in the art, for example, as described in U.S. Patent 5,223,570, the disclosure of which is incorporated herein by reference.
- transesterification product is formed during the formation of the preformed stabilizer a certain amount of transesterification product is formed.
- This product is an adduct of the unsaturated organic compound used to form the macromer and the carrier polyol.
- This adduct can interfere with the filterabiiity of the final graft polyol, alter its viscosity, increase fouling of the reactor, and alter the chemical properties of the final graft polyol.
- the present inventors have unexpectedly found a straight-forward method for preventing this transesterification reaction.
- Suitable phosphorous compounds include compounds containing phosphorus-oxygen bonds, by way of non-limiting example: phosphoric acid, phosphorous acid, compounds containing the phosphate and/or phosphite anion, and mixtures of all of these compounds. In the present specification and claims all of these compounds are intended to be encompassed by the term phosphorous compounds.
- the amount of phosphorous compound be used in a weight to weight ratio of from 1:1 to 10:1 relative to the weight of the Lewis acid catalyst used in the reaction for formation of the macromer.
- the preferred amounts range from 0.2 to 500 ppm, more preferably from 0.5 to 250 ppm, and most preferably from 1 to 150 ppm of phosphorous compound.
- the phosphorous compound can be added either to the macromer before it is used in the reaction for the formation of the preformed stabilizer or as an initial charge to the reactor for formation of the preformed stabilizer.
- a macromer is formed as follows.
- the conventional polyol used is a sucrose and water co-initiated polyol having a theoretical number average molecular weight of approxima- teiy 6,800 Daltons.
- the conventional polyol has an intrinsic unsaturation of approximately 0.09-0.15 meq/g.
- the conventional polyol contains approximately 93 wt.% propylene oxide and initiators based on the total weight of the polyol and approximately a 7 wt.% ethylene oxide cap based on the total weight.
- the hydroxyl number of the conventional polyol is approximately 25.
- the conventional polyol has a theoretical average functionality of approximately 4.51 to 4.97 based on Gel Permeation
- the macromer is formed by first charging to a reactor the conventional polyol and 50 ppm dibutyltin dilaurate (T-12) catalyst at room temperature. The mixture is heated to 80 °C and the TMI is added dropwise to the mixture over 0.5 hours. The mixture was allowed to react another hour after completion of the addition. The macromer is subsequently bottled for storage.
- T-12 dibutyltin dilaurate
- a carrier polyol for use in the preformed stabilizer reaction is a glycerin-initiated con- ventional polyol comprising a heteric portion formed from propylene oxide and ethylene oxide at a molar ratio of 4.2:1.
- the carrier polyol also has a propylene oxide cap of 10 wt.% based on the total weight of the polyol and a hydroxyl number of 51.
- a first mixture included: macromer, carrier polyol and phosphoric acid present in a weight to weight ration of 1:1 based on the weight of the T-12.
- a second mixture included the macromer and the carrier polyol only. Both mixtures were heated to 130 °C and held there for a period of time. This temperature is the stripping temperature usually used to strip the unreacted components from the preformed stabilizer reaction. Then Gel Permeation Chromatography (GPC) was performed on each sample and the overlayed results are shown in Figure 1.
- chromatogram 40 represents the second mixture while chromatogram 42 represents the first mixture, which contained the phosphoric acid.
- Shoulder 44 in Figure 1 represents the position of the transesterification product of the TMI and the carrier polyol.
- the results demonstrate that in the absence of phosphoric acid, chromatogram 40, there is significant formation of this product. In the presence of the phosphoric acid there is none.
- a preformed stabilizer was prepared as follows. A portion of the carrier polyol, no reaction modifier, and all of the macromer are charged to a reactor, agitated and heated to 110 °C. The amount of macromer used based on the total weight of macromer and carrier polyol in this reaction ranges from 24 to 28% by weight. The ethylenically unsaturated monomers, acrylonitrile and stryrene at a weight to weight ratio of 1 :20, are charged to a monomer feed tank while the remainder of the carrier polyol and the free radical initiator, t-amyl peroxy-2-ethyl hexanoate (TRIGO- NOX 121), are charged to a polyol feed tank.
- TRIGO- NOX 121 t-amyl peroxy-2-ethyl hexanoate
- the streams from the monomer feed tank and the polyol feed tank are pumped together through an in-line static mixer and charged into the hot mixture in the reactor.
- the reaction temperature is 126 °C and the total feed time is 70 minutes.
- the preformed stabilizer is stripped at 130 °C.
- the final calculated solids content in the preformed stabilizer is from about 5 to 20%.
- the macromer, described above did not contain any phosphoric acid.
- the macromer did contain phosphoric acid at a weight to weight ratio of 1:1 based on the weight of the T-12.
- Each preformed stabilizer was then subjected to GPC and the overlayed results are shown in Figure 2.
- chromatogram 50 represents a preformed stabilizer formed without phosphoric acid and chromatogram 52 represents a preformed stabilizer prepared with phosphoric acid.
- Peak 54 represents the transesterification product of the TMI and the carrier polyol. The results demonstrate that the presence of the phosphoric acid significantly reduces the formation of the transesterification product.
- a preformed stabilizer was prepared with phosphoric acid at a 1:1 weight ratio based on the T-12 or a preformed stabilizer was prepared without phosphoric acid as described above.
- Chromatogram 70 represents a preformed stabilizer formed using no phosphoric acid.
- Chromatogram 72 represents a preformed stabilizer in the presence of a 1 :1 weight ratio of phosphoric acid to T-12 from the macromer.
- Peak 74 represents the transesterification product of TMI and the carrier polyol. The results show that the preformed stabilizer made in the presence of the phosphoric acid has a dramatically redu- ced level of transesterification products.
- a graft polyol made with the preformed stabilizer having phosphoric acid had a low viscosity and could readily be filtered through a 25 micron filter, however, a graft polyol prepared with the preformed stabilizer not having phosphoric acid had a higher viscosity and could not be filtered through a 25 micron filter.
- the carrier polyol used is a propylene glycol and water co-initiated polyol con- taining only propylene oxide.
- the polyol had a hydroxyl number of 56 and a number average molecular weight of 1942 Daltons.
- Peak 92 is the transesterification product of TMI and the carrier polyol.
- the carrier polyol used is a glycerine-initiated polyol containing only propylene oxide.
- the polyol had a hydroxyl number of 64 and a number average molecular weight of 2495 Daltons.
- Peak 100 is the transesterification product of TMI and the carrier polyol.
- the carrier polyol used is a glycerine- initiated polyol formed as a propylene oxide ethylene oxide heteric containing approximately 13% ethylene oxide.
- the polyol also has a propylene oxide cap of 10%.
- the polyol had a hydroxyl number of 64 and a number average molecular weight of 2937 Daltons. Peak 102 is the transesterification product of TMI and the carrier polyol.
- the inventors have also found that use of the preformed stabilizer prepared according to the present invention in formation of graft poiyols dramatically reduces the reactor fouling that usually accompanies graft polyol reactions. In fact it has been found that the reactor can be run at least 17% longer than before resulting in enhanced productivi- ty.
- the present invention finds utilization at a number of different points in the usual process for formation of graft poiyols.
- the present invention specifically prevents transesterification reactions that can occur when a macromer is combined with the carrier polyol in the presence of heating.
- the phosphoric acid can be added to the macromer after formation of the macromer and during storage of the macromer.
- the phosphoric acid can be added to a reactor during the formation reaction for forming of a preformed stabilizer as described above.
- the phosphoric acid can be added to a graft polyol formation reaction either in the presence or the absence of a preformed stabili- zer.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE602004015291T DE602004015291D1 (en) | 2003-06-27 | 2004-05-26 | PROCESS FOR THE FORMATION OF PREPARED STABILIZER POLYOLS |
EP04739363A EP1641852B1 (en) | 2003-06-27 | 2004-05-26 | Process for formation of preformed stabilizer polyols |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/608,247 | 2003-06-27 | ||
US10/608,247 US7148288B2 (en) | 2003-06-27 | 2003-06-27 | Process for formation of preformed stabilizer polyols |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005003200A1 true WO2005003200A1 (en) | 2005-01-13 |
Family
ID=33540525
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/005659 WO2005003200A1 (en) | 2003-06-27 | 2004-05-26 | Process for formation of preformed stabilizer polyols |
Country Status (6)
Country | Link |
---|---|
US (1) | US7148288B2 (en) |
EP (1) | EP1641852B1 (en) |
AT (1) | ATE402200T1 (en) |
DE (1) | DE602004015291D1 (en) |
ES (1) | ES2308190T3 (en) |
WO (1) | WO2005003200A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8247507B2 (en) | 2006-09-21 | 2012-08-21 | Basf Se | Cationic polymers as thickeners for aqueous and alcoholic compositions |
WO2016083538A1 (en) | 2014-11-27 | 2016-06-02 | Basf Se | Synthesis of polymer polyols in unsaturated polyols, polymer polyols and their use |
WO2018019708A1 (en) | 2016-07-27 | 2018-02-01 | Basf Se | Stabiliser for polyolefin-in-polyether polyol dispersions |
US10370479B2 (en) | 2014-04-30 | 2019-08-06 | Basf Se | Process for making a polymer polyol |
CN110283308A (en) * | 2019-06-21 | 2019-09-27 | 南京金栖化工集团有限公司 | A kind of preparation method of the stabilizer for synthesis of polymer polyalcohol |
US10472458B2 (en) | 2014-04-30 | 2019-11-12 | Basf Se | Stabilizer for polymer polyol production processes |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1728825B2 (en) * | 2005-06-02 | 2013-10-23 | Dow Global Technologies LLC | Toughened structural epoxy adhesive |
US20080071056A1 (en) * | 2006-09-14 | 2008-03-20 | Borst Joseph P | Method of forming a graft polyol and polyurethane article formed from the graft polyol |
US8835565B2 (en) * | 2012-04-18 | 2014-09-16 | Bayer Materialscience Llc | Preformed stabilizers useful for the production of polymer polyols and polymer polyols produced therefrom |
BR112015007609B1 (en) | 2012-10-05 | 2021-05-11 | Dow Global Technologies Llc | polyurethane foam |
KR20160135335A (en) * | 2014-03-21 | 2016-11-25 | 바스프 에스이 | Solid electrolyte |
CN113439096A (en) | 2019-02-07 | 2021-09-24 | 陶氏环球技术有限责任公司 | Process for preparing copolymer polyols |
WO2020163400A1 (en) | 2019-02-07 | 2020-08-13 | Dow Global Technologies Llc | Monomer recovery process |
US11421063B2 (en) | 2019-10-10 | 2022-08-23 | Covestro Llc | Preformed stabilizers with improved stability |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4522976A (en) * | 1984-05-17 | 1985-06-11 | Basf Wyandotte Corporation | Graft polymer dispersion in a mixture of low molecular weight polyols and polyether polyols and polyurethane foams prepared therefrom |
WO2003097710A1 (en) * | 2002-05-15 | 2003-11-27 | Basf Corporation | Graft polyols prepared by a continuous process |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5223570A (en) * | 1990-02-07 | 1993-06-29 | Basf Corporation | Method for the preparation of graft polymer dispersions having broad particle size distribution without wildly fluctuating viscosities |
EP0768324B1 (en) * | 1995-10-10 | 2000-08-16 | Bayer Ag | Continuous process for the preparation of highly stable, finely divided, low viscosity polymer polyols of small average particle size |
US6316584B1 (en) | 1997-06-10 | 2001-11-13 | Akzo Nobel Nv | Method for producing polyesters and copolyesters |
DE19829593A1 (en) | 1998-07-02 | 2000-01-05 | Henkel Kgaa | Process for the preparation of compounds with terminal OH groups |
US6172164B1 (en) * | 1999-04-01 | 2001-01-09 | Basf Corporation | Process for making graft polyols using t-amyl peroxy free radical initiator |
US6780932B2 (en) | 2002-03-22 | 2004-08-24 | Basf Corporation | Graft polyols prepared by a continuous process |
-
2003
- 2003-06-27 US US10/608,247 patent/US7148288B2/en not_active Expired - Lifetime
-
2004
- 2004-05-26 EP EP04739363A patent/EP1641852B1/en not_active Expired - Lifetime
- 2004-05-26 ES ES04739363T patent/ES2308190T3/en not_active Expired - Lifetime
- 2004-05-26 WO PCT/EP2004/005659 patent/WO2005003200A1/en active IP Right Grant
- 2004-05-26 DE DE602004015291T patent/DE602004015291D1/en not_active Expired - Lifetime
- 2004-05-26 AT AT04739363T patent/ATE402200T1/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4522976A (en) * | 1984-05-17 | 1985-06-11 | Basf Wyandotte Corporation | Graft polymer dispersion in a mixture of low molecular weight polyols and polyether polyols and polyurethane foams prepared therefrom |
WO2003097710A1 (en) * | 2002-05-15 | 2003-11-27 | Basf Corporation | Graft polyols prepared by a continuous process |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8247507B2 (en) | 2006-09-21 | 2012-08-21 | Basf Se | Cationic polymers as thickeners for aqueous and alcoholic compositions |
US10370479B2 (en) | 2014-04-30 | 2019-08-06 | Basf Se | Process for making a polymer polyol |
US10472458B2 (en) | 2014-04-30 | 2019-11-12 | Basf Se | Stabilizer for polymer polyol production processes |
WO2016083538A1 (en) | 2014-11-27 | 2016-06-02 | Basf Se | Synthesis of polymer polyols in unsaturated polyols, polymer polyols and their use |
CN107001579A (en) * | 2014-11-27 | 2017-08-01 | 巴斯夫欧洲公司 | Synthesis of polymer polyols in unsaturated polyols, polymer polyols and their use |
US10294336B2 (en) | 2014-11-27 | 2019-05-21 | Basf Se | Synthesis of polymer polyols in unsaturated polyols, polymer polyols and their use |
CN107001579B (en) * | 2014-11-27 | 2020-10-23 | 巴斯夫欧洲公司 | Synthesis of polymer polyols in unsaturated polyols, polymer polyols and their use |
WO2018019708A1 (en) | 2016-07-27 | 2018-02-01 | Basf Se | Stabiliser for polyolefin-in-polyether polyol dispersions |
CN110283308A (en) * | 2019-06-21 | 2019-09-27 | 南京金栖化工集团有限公司 | A kind of preparation method of the stabilizer for synthesis of polymer polyalcohol |
Also Published As
Publication number | Publication date |
---|---|
US20040266958A1 (en) | 2004-12-30 |
ES2308190T3 (en) | 2008-12-01 |
ATE402200T1 (en) | 2008-08-15 |
DE602004015291D1 (en) | 2008-09-04 |
EP1641852A1 (en) | 2006-04-05 |
US7148288B2 (en) | 2006-12-12 |
EP1641852B1 (en) | 2008-07-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7148288B2 (en) | Process for formation of preformed stabilizer polyols | |
EP1506240B1 (en) | Graft polyols prepared by a continuous process | |
EP1192198B1 (en) | Process for making graft polyols using t-amyl peroxy free radical initiator | |
EP1568727B1 (en) | Process for production of polymer polyols | |
US4521546A (en) | Graft copolymers from vinyl monomers and polyurethane oligomers and polyurethanes prepared therefrom | |
US6201035B1 (en) | Use of low unsaturated polyether polyols in high resilience slabstock foam applications | |
EP3512888B1 (en) | Improved polymer polyol quality | |
US6780932B2 (en) | Graft polyols prepared by a continuous process | |
EP0353070B1 (en) | Polyol polyacrylate dispersants | |
US5223570A (en) | Method for the preparation of graft polymer dispersions having broad particle size distribution without wildly fluctuating viscosities | |
US4140667A (en) | Graft copolymers from vinyl monomers and unsaturated polyols containing alkenyl aryl constituents and polyurethanes prepared therefrom | |
US4539339A (en) | Polyurethane foams made from vinyl polymer polyols | |
EP1589051A1 (en) | Process for preparing graft polyols using enol ethers as reaction moderators | |
US4202947A (en) | Polyurethane foam prepared from graft copolymers of vinyl monomers and unsaturated polyols containing alkenyl aryl constituents | |
US5225481A (en) | Polyol polyacrylate dispersants | |
US4321342A (en) | Curable fixtures of polyepoxides and amine-terminated graft polymer dispersions | |
EP0325818A1 (en) | Polymer polyols derived from novel dispersing media | |
EP0212843A2 (en) | Use of styrene-acrylonitrile polymer polyols containing partially alkoxylated polyoxyalkyleneamines | |
EP0177192A2 (en) | Vinyl polymer polyols and polyurethane foams made therefrom | |
MXPA98004643A (en) | Polymer of reinforcement grafting made in fluidosde perfluorocarb |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
DPEN | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2004739363 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2004739363 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 2004739363 Country of ref document: EP |