CA1232999A - Procede de preparationde polymeres "vivants" - Google Patents

Procede de preparationde polymeres "vivants"

Info

Publication number: CA1232999A
Authority: CA; Canada
Prior art keywords: group; substituents; carbon atoms; polymer; hydrocarbyl
Prior art date: 1983-11-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000467173A

Other languages

English (en)

Inventor

William B. Farnham

Dotsevi Y. Sogah

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-11-07

Filing date

1984-11-06

Publication date

1988-02-16

1983-11-07 Priority claimed from US06/549,408 external-priority patent/US4524196A/en

1984-11-06 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1988-02-16 Application granted granted Critical

1988-02-16 Publication of CA1232999A publication Critical patent/CA1232999A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 90
238000004519 manufacturing process Methods 0.000 title abstract description 5
239000000178 monomer Substances 0.000 claims abstract description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 38
239000003999 initiator Substances 0.000 claims abstract description 33
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 18
150000002500 ions Chemical class 0.000 claims abstract description 11
239000003426 co-catalyst Substances 0.000 claims abstract description 7
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims abstract description 4
-1 sorbyl Chemical group 0.000 claims description 62
238000000034 method Methods 0.000 claims description 60
230000008569 process Effects 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 26
230000000379 polymerizing effect Effects 0.000 claims description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
230000000977 initiatory effect Effects 0.000 claims description 18
125000001931 aliphatic group Chemical group 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
229910052718 tin Inorganic materials 0.000 claims description 9
125000000468 ketone group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229920001610 polycaprolactone Polymers 0.000 claims description 5
229910052710 silicon Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
125000000466 oxiranyl group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 13
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 12
229920001577 copolymer Polymers 0.000 abstract description 5
229920001519 homopolymer Polymers 0.000 abstract description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 2
229910052751 metal Inorganic materials 0.000 abstract description 2
239000002184 metal Substances 0.000 abstract description 2
239000002023 wood Substances 0.000 abstract description 2
239000011521 glass Substances 0.000 abstract 1
125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 abstract 1
125000000082 organogermanium group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 34
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
238000006116 polymerization reaction Methods 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 20
238000005227 gel permeation chromatography Methods 0.000 description 19
229910052786 argon Inorganic materials 0.000 description 16
125000004093 cyano group Chemical group *C#N 0.000 description 15
239000004926 polymethyl methacrylate Substances 0.000 description 14
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
229920003229 poly(methyl methacrylate) Polymers 0.000 description 13
239000002253 acid Substances 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 8
230000003213 activating effect Effects 0.000 description 8
238000010539 anionic addition polymerization reaction Methods 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
229910052782 aluminium Inorganic materials 0.000 description 7
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
230000007935 neutral effect Effects 0.000 description 7
229920000058 polyacrylate Polymers 0.000 description 7
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000002085 enols Chemical group 0.000 description 6
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 6
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 5
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
238000000576 coating method Methods 0.000 description 5
125000004386 diacrylate group Chemical group 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 5
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
101001001462 Homo sapiens Importin subunit alpha-5 Proteins 0.000 description 4
102100036186 Importin subunit alpha-5 Human genes 0.000 description 4
229930194542 Keto Natural products 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000000049 pigment Substances 0.000 description 4
239000004632 polycaprolactone Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 4
229940096522 trimethylolpropane triacrylate Drugs 0.000 description 4
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 3
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
229920000877 Melamine resin Polymers 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
229910010066 TiC14 Inorganic materials 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
VNDYJBBGRKZCSX-UHFFFAOYSA-L Zinc bromide Inorganic materials Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000006229 carbon black Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
210000003298 dental enamel Anatomy 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000004922 lacquer Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000003973 paint Substances 0.000 description 3
229920000120 polyethyl acrylate Polymers 0.000 description 3
238000010791 quenching Methods 0.000 description 3
230000000171 quenching effect Effects 0.000 description 3
238000010526 radical polymerization reaction Methods 0.000 description 3
125000005207 tetraalkylammonium group Chemical group 0.000 description 3
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 2
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 2
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
ZTJNPDLOIVDEEL-UHFFFAOYSA-N 2-acetyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(C)=O ZTJNPDLOIVDEEL-UHFFFAOYSA-N 0.000 description 2
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
WIYVVIUBKNTNKG-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydronaphthalene-2-carboxylic acid Chemical compound C1CC(C(O)=O)=CC2=C1C=C(OC)C(OC)=C2 WIYVVIUBKNTNKG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
229910021244 Co2Si Inorganic materials 0.000 description 2
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
101150093766 Segment-6 gene Proteins 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920006217 cellulose acetate butyrate Polymers 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002466 imines Chemical group 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 2
239000002304 perfume Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
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229910052717 sulfur Inorganic materials 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
HEYWXOWEALDDOL-UHFFFAOYSA-N tetraethylazanium;azide Chemical compound [N-]=[N+]=[N-].CC[N+](CC)(CC)CC HEYWXOWEALDDOL-UHFFFAOYSA-N 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
LAUZAYCJJOZDKK-UHFFFAOYSA-M tributyl-(2-methylcyclohexen-1-yl)oxystannane Chemical compound CCCC[Sn](CCCC)(CCCC)OC1=C(C)CCCC1 LAUZAYCJJOZDKK-UHFFFAOYSA-M 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
229940094989 trimethylsilane Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000467173A 1983-11-07 1984-11-06 Procede de preparationde polymeres "vivants" Expired CA1232999A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US549,408		1983-11-07
US06/549,408 US4524196A (en)	1982-06-17	1983-11-07	Process for preparing "living" polymers
US660,589		1984-10-18
US06/660,589 US4581428A (en)	1982-06-17	1984-10-18	Process for preparing "living" polymers using tetracoordinate organosilicon, organotin or organogermanium polymerization initiator with bifluoride ion source co-catalyst

Publications (1)

Publication Number	Publication Date
CA1232999A true CA1232999A (fr)	1988-02-16

Family

ID=27069123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000467173A Expired CA1232999A (fr)	1983-11-07	1984-11-06	Procede de preparationde polymeres "vivants"

Country Status (1)

Country	Link
CA (1)	CA1232999A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115851065A (zh) *	2022-11-25	2023-03-28	湖北双键精细化工有限公司	一种与uv罩光面漆相配套的单组份底漆用改性丙烯酸乳液及其制备方法

1984
- 1984-11-06 CA CA000467173A patent/CA1232999A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115851065A (zh) *	2022-11-25	2023-03-28	湖北双键精细化工有限公司	一种与uv罩光面漆相配套的单组份底漆用改性丙烯酸乳液及其制备方法
CN115851065B (zh) *	2022-11-25	2023-08-15	湖北双键精细化工有限公司	一种与uv罩光面漆相配套的单组份底漆用改性丙烯酸乳液及其制备方法

Legal Events

Date	Code	Title	Description
2005-02-16	MKEX	Expiry

Publication	Publication Date	Title
CA1232998A (fr)	1988-02-16	Polymeres vivants et procede de preparation
US4681918A (en)	1987-07-21	"Living" polymers and process for their preparation
US4508880A (en)	1985-04-02	"Living" polymers and process for their preparation
US4414372A (en)	1983-11-08	Process for preparing living polymers
US4417034A (en)	1983-11-22	Living polymers and process for their preparation
CA2134870C (fr)	2007-07-17	Procede ameliore de polymerisation dans un systeme aqueux
JP3113278B2 (ja)	2000-11-27	マクロモノマー連鎖移動剤を用いた架橋可能ポリマーの製造方法
US5773534A (en)	1998-06-30	Preparing crosslinkable polymers employing macromonomer chain transfer agents
EP0145263B1 (fr)	1991-04-17	Polymères vivants et procédé de préparation
CA1232999A (fr)	1988-02-16	Procede de preparationde polymeres "vivants"
US4783500A (en)	1988-11-08	"Living" polymers and process for their preparation
JPH055009A (ja)	1993-01-14	ビニル系単量体の重合法
KR910003839B1 (ko)	1991-06-12	"활성"중합체의 제법
EP1165629A1 (fr)	2002-01-02	Composition catalytique et procede de fabrication d'un polymere ou d'un copolymere
EP1091964B1 (fr)	2003-01-02	Composes d'aluminium pour la production de polymeres vinyliques
JPS62292806A (ja)	1987-12-19	原子団移動重合法およびリビングポリマ−
JP2000506928A (ja)	2000-06-06	不活性不飽和物を用いたフリーラジカルポリマー連鎖開始
IL105650A (en)	1996-10-16	Preparation of polymers that can be crosslinked by using macromonomeric chain transfer means
MXPA00012920A (en)	2002-02-26	Aluminium compounds for producing vinylic polymers