CA1123537A - Synthese et copolymerisation de monomeres macromoleculaires blocs coniques - Google Patents

Synthese et copolymerisation de monomeres macromoleculaires blocs coniques

Info

Publication number: CA1123537A
Authority: CA; Canada
Prior art keywords: graft copolymer; styrene; copolymerizable; macromolecular monomer; copolymer
Prior art date: 1976-05-27
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

CA369,251A

Other languages

English (en)

Inventor

Morris J. Danzig

Ralph Milkovich

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.)

Unilever Bestfoods North America

Original Assignee

Unilever Bestfoods North America

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.)

1976-05-27

Filing date

1981-01-23

Publication date

1982-05-11

1976-05-27 Priority claimed from US05/690,757 external-priority patent/US4104330A/en

1981-01-23 Application filed by Unilever Bestfoods North America filed Critical Unilever Bestfoods North America

1981-01-23 Priority to CA369,251A priority Critical patent/CA1123537A/fr

1982-05-11 Application granted granted Critical

1982-05-11 Publication of CA1123537A publication Critical patent/CA1123537A/fr

Status Expired legal-status Critical Current

Links

238000007334 copolymerization reaction Methods 0.000 title claims abstract description 16
230000015572 biosynthetic process Effects 0.000 title description 2
238000003786 synthesis reaction Methods 0.000 title 1
239000000178 monomer Substances 0.000 claims abstract description 243
229920000578 graft copolymer Polymers 0.000 claims abstract description 100
150000001993 dienes Chemical class 0.000 claims abstract description 32
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 31
239000000203 mixture Substances 0.000 claims abstract description 31
238000009826 distribution Methods 0.000 claims abstract description 23
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 19
229920001169 thermoplastic Polymers 0.000 claims abstract description 15
239000004416 thermosoftening plastic Substances 0.000 claims abstract description 15
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 14
239000004593 Epoxy Chemical group 0.000 claims abstract description 7
125000005068 thioepoxy group Chemical group S(O*)* 0.000 claims abstract description 7
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 201
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 103
229920000642 polymer Polymers 0.000 claims description 97
229920001577 copolymer Polymers 0.000 claims description 74
-1 ethylene, propylene Chemical group 0.000 claims description 22
239000005977 Ethylene Substances 0.000 claims description 17
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
239000003999 initiator Substances 0.000 claims description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
125000000129 anionic group Chemical group 0.000 claims description 10
230000009257 reactivity Effects 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 6
125000003827 glycol group Chemical group 0.000 claims description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
229920005684 linear copolymer Polymers 0.000 claims description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical class 0.000 claims description 4
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 claims description 3
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical class 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000005442 diisocyanate group Chemical group 0.000 claims 1
125000005395 methacrylic acid group Chemical class 0.000 claims 1
229920002554 vinyl polymer Polymers 0.000 abstract description 7
150000001875 compounds Chemical class 0.000 abstract description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 4
125000003700 epoxy group Chemical group 0.000 abstract description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Chemical group OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 114
239000000243 solution Substances 0.000 description 69
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 19
238000000034 method Methods 0.000 description 19
238000002360 preparation method Methods 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000004793 Polystyrene Substances 0.000 description 16
230000000704 physical effect Effects 0.000 description 16
239000011324 bead Substances 0.000 description 15
229920001195 polyisoprene Polymers 0.000 description 15
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 14
229920002223 polystyrene Polymers 0.000 description 14
238000006116 polymerization reaction Methods 0.000 description 13
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 9
229940063557 methacrylate Drugs 0.000 description 9
239000007787 solid Substances 0.000 description 9
150000001450 anions Chemical class 0.000 description 8
239000012153 distilled water Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000000725 suspension Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
239000004711 α-olefin Substances 0.000 description 8
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
239000004800 polyvinyl chloride Substances 0.000 description 7
229920000915 polyvinyl chloride Polymers 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000005227 gel permeation chromatography Methods 0.000 description 6
229960004592 isopropanol Drugs 0.000 description 6
229920003023 plastic Polymers 0.000 description 6
239000004033 plastic Substances 0.000 description 6
239000003381 stabilizer Substances 0.000 description 6
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 5
235000006708 antioxidants Nutrition 0.000 description 5
229920001400 block copolymer Polymers 0.000 description 5
229920001971 elastomer Polymers 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000005266 side chain polymer Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
230000001954 sterilising effect Effects 0.000 description 5
238000004659 sterilization and disinfection Methods 0.000 description 5
ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 4
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
230000003078 antioxidant effect Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000004040 coloring Methods 0.000 description 4
230000006835 compression Effects 0.000 description 4
238000007906 compression Methods 0.000 description 4
229920001519 homopolymer Polymers 0.000 description 4
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
238000005275 alloying Methods 0.000 description 3
238000010539 anionic addition polymerization reaction Methods 0.000 description 3
210000000988 bone and bone Anatomy 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229920005549 butyl rubber Polymers 0.000 description 3
239000001506 calcium phosphate Substances 0.000 description 3
OGHNVEJMJSYVRP-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2 OGHNVEJMJSYVRP-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
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150000002430 hydrocarbons Chemical class 0.000 description 3
229940102838 methylmethacrylate Drugs 0.000 description 3
SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000000518 rheometry Methods 0.000 description 3
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 3
PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 3
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229920002799 BoPET Polymers 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
235000010650 Hyssopus officinalis Nutrition 0.000 description 2
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000005041 Mylar™ Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 2
230000008859 change Effects 0.000 description 2
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238000000748 compression moulding Methods 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
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239000004615 ingredient Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
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239000003505 polymerization initiator Substances 0.000 description 2
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239000001267 polyvinylpyrrolidone Substances 0.000 description 2
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SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
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229940078499 tricalcium phosphate Drugs 0.000 description 2
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UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
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AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
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FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
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238000013329 compounding Methods 0.000 description 1
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239000000356 contaminant Substances 0.000 description 1
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239000013256 coordination polymer Substances 0.000 description 1
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238000004132 cross linking Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
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238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000005397 methacrylic acid ester group Chemical group 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical compound C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
VATDYQWILMGLEW-UHFFFAOYSA-N sec-butyllithium Chemical compound [Li]C(C)CC VATDYQWILMGLEW-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
JBIQAPKSNFTACH-UHFFFAOYSA-K vanadium oxytrichloride Chemical compound Cl[V](Cl)(Cl)=O JBIQAPKSNFTACH-UHFFFAOYSA-K 0.000 description 1

Landscapes

Graft Or Block Polymers (AREA)

CA369,251A 1976-05-27 1981-01-23 Synthese et copolymerisation de monomeres macromoleculaires blocs coniques Expired CA1123537A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA369,251A CA1123537A (fr)	1976-05-27	1981-01-23	Synthese et copolymerisation de monomeres macromoleculaires blocs coniques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/690,757 US4104330A (en)	1976-05-27	1976-05-27	Synthesis and copolymerization of tapered block macromer monomers
US690,757		1976-05-27
CA278,993A CA1109584A (fr)	1976-05-27	1977-05-24	Synthese et copolymerisation de monomeres de type macromeres, sequences, effiles
CA369,251A CA1123537A (fr)	1976-05-27	1981-01-23	Synthese et copolymerisation de monomeres macromoleculaires blocs coniques

Publications (1)

Publication Number	Publication Date
CA1123537A true CA1123537A (fr)	1982-05-11

Family

ID=27165090

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA369,251A Expired CA1123537A (fr)	1976-05-27	1981-01-23	Synthese et copolymerisation de monomeres macromoleculaires blocs coniques

Country Status (1)

Country	Link
CA (1)	CA1123537A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991012284A1 (fr) *	1990-02-14	1991-08-22	Elf Atochem S.A.	Macromonomeres multisequences fonctionnalises et leur procede de fabrication

1981
- 1981-01-23 CA CA369,251A patent/CA1123537A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991012284A1 (fr) *	1990-02-14	1991-08-22	Elf Atochem S.A.	Macromonomeres multisequences fonctionnalises et leur procede de fabrication
US5391628A (en) *	1990-02-14	1995-02-21	Elf Atochem S.A.	Functionalized multiblock macromonomers and process for their production
EP0442804B1 (fr) *	1990-02-14	1996-08-28	Elf Atochem S.A.	Macromonomères multiséquencés fonctionnalisés et leur procédé de fabrication

Legal Events

Date	Code	Title	Description
1999-05-11	MKEX	Expiry

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