CA1111176A - Procede d'obtention de polymeres et de copolymeres d'halogenure de vinyle avec des polyolefines - Google Patents

Procede d'obtention de polymeres et de copolymeres d'halogenure de vinyle avec des polyolefines

Info

Publication number: CA1111176A
Authority: CA; Canada
Prior art keywords: polymerization; polyolefin; weight; monomer; vinyl halide
Prior art date: 1976-11-30
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

CA270,387A

Other languages

English (en)

Inventor

Leigh E. Walker

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.)

Occidental Chemical Corp

Original Assignee

Hooker Chemicals and Plastics Corp

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.)

1976-11-30

Filing date

1977-01-25

Publication date

1981-10-20

1976-11-30 Priority claimed from US05/746,048 external-priority patent/US4067928A/en

1977-01-25 Application filed by Hooker Chemicals and Plastics Corp filed Critical Hooker Chemicals and Plastics Corp

1981-10-20 Application granted granted Critical

1981-10-20 Publication of CA1111176A publication Critical patent/CA1111176A/fr

Status Expired legal-status Critical Current

Links

-1 vinyl halide Chemical class 0.000 title claims abstract description 173
229920002554 vinyl polymer Polymers 0.000 title claims abstract description 147
229920000098 polyolefin Polymers 0.000 title claims abstract description 140
229920000642 polymer Polymers 0.000 title claims abstract description 104
238000000034 method Methods 0.000 title claims description 106
229920001577 copolymer Polymers 0.000 title claims description 21
239000000178 monomer Substances 0.000 claims abstract description 152
238000006116 polymerization reaction Methods 0.000 claims abstract description 147
238000006243 chemical reaction Methods 0.000 claims abstract description 114
239000000203 mixture Substances 0.000 claims abstract description 42
239000002245 particle Substances 0.000 claims abstract description 34
238000012662 bulk polymerization Methods 0.000 claims abstract description 13
230000008569 process Effects 0.000 claims description 97
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 73
229920001897 terpolymer Polymers 0.000 claims description 31
239000011541 reaction mixture Substances 0.000 claims description 29
238000013022 venting Methods 0.000 claims description 25
239000003999 initiator Substances 0.000 claims description 24
238000013019 agitation Methods 0.000 claims description 23
239000000376 reactant Substances 0.000 claims description 18
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
229920001519 homopolymer Polymers 0.000 claims description 17
150000001993 dienes Chemical class 0.000 claims description 16
230000006872 improvement Effects 0.000 claims description 12
150000001336 alkenes Chemical class 0.000 claims description 10
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
230000000379 polymerizing effect Effects 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
230000000977 initiatory effect Effects 0.000 claims description 7
229920001291 polyvinyl halide Polymers 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000007791 liquid phase Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 5
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
239000004698 Polyethylene Substances 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
229920001038 ethylene copolymer Polymers 0.000 claims description 4
150000001451 organic peroxides Chemical group 0.000 claims description 4
229920000573 polyethylene Polymers 0.000 claims description 4
239000004743 Polypropylene Substances 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
229920001155 polypropylene Polymers 0.000 claims description 3
229920000089 Cyclic olefin copolymer Polymers 0.000 claims 5
239000004709 Chlorinated polyethylene Substances 0.000 claims 2
229920001384 propylene homopolymer Polymers 0.000 claims 1
230000036647 reaction Effects 0.000 claims 1
238000012545 processing Methods 0.000 abstract description 9
238000002844 melting Methods 0.000 abstract description 6
230000008018 melting Effects 0.000 abstract description 6
238000010438 heat treatment Methods 0.000 abstract description 5
238000002485 combustion reaction Methods 0.000 abstract 1
239000000047 product Substances 0.000 description 63
206010001497 Agitation Diseases 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
229920000578 graft copolymer Polymers 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
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 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010094 polymer processing Methods 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229940117958 vinyl acetate Drugs 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
208000036366 Sensation of pressure Diseases 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000008859 change Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
230000004927 fusion Effects 0.000 description 3
229920001112 grafted polyolefin Polymers 0.000 description 3
239000000243 solution Substances 0.000 description 3
229920006029 tetra-polymer Polymers 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
WVLIQUPRRVSTGK-UHFFFAOYSA-N 6-(1,3-dioxopropan-2-yl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C(C=O)C=O)=N1 WVLIQUPRRVSTGK-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000012644 addition polymerization Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
125000005670 ethenylalkyl group Chemical group 0.000 description 2
FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical compound CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 2
238000009863 impact test Methods 0.000 description 2
239000007788 liquid Substances 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
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000005394 methallyl group Chemical group 0.000 description 2
AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
238000010298 pulverizing process Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000007928 solubilization Effects 0.000 description 2
238000005063 solubilization Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000012546 transfer Methods 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical group C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
VFRMAHVDXYSEON-UHFFFAOYSA-N 1,1-diiodoethene Chemical compound IC(I)=C VFRMAHVDXYSEON-UHFFFAOYSA-N 0.000 description 1
DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 description 1
OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
ZMFWTUBNIJBJDB-UHFFFAOYSA-N 6-hydroxy-2-methylquinoline-4-carboxylic acid Chemical compound C1=C(O)C=CC2=NC(C)=CC(C(O)=O)=C21 ZMFWTUBNIJBJDB-UHFFFAOYSA-N 0.000 description 1
RZBBHEJLECUBJT-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylacetate Chemical compound CC(C)CCCCCOC(=O)CS RZBBHEJLECUBJT-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-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
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
239000006057 Non-nutritive feed additive Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
OAEPNGOVHBRMGY-UHFFFAOYSA-N butylamino prop-2-enoate Chemical group CCCCNOC(=O)C=C OAEPNGOVHBRMGY-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
JHCKGVJZNIWNJK-UHFFFAOYSA-N diethyl pent-2-enedioate Chemical compound CCOC(=O)CC=CC(=O)OCC JHCKGVJZNIWNJK-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
230000003292 diminished effect Effects 0.000 description 1
230000003467 diminishing effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940035564 duration Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
GQRMMMQODXFNCX-UHFFFAOYSA-N ethene;2-methylbuta-1,3-diene Chemical compound C=C.CC(=C)C=C GQRMMMQODXFNCX-UHFFFAOYSA-N 0.000 description 1
WUIOPDYOMAXHRZ-UHFFFAOYSA-N ethenyl 4-chlorobenzoate Chemical class ClC1=CC=C(C(=O)OC=C)C=C1 WUIOPDYOMAXHRZ-UHFFFAOYSA-N 0.000 description 1
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010559 graft polymerization reaction Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
DPUXQWOMYBMHRN-UHFFFAOYSA-N hexa-2,3-diene Chemical compound CCC=C=CC DPUXQWOMYBMHRN-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000001788 irregular Effects 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
230000007246 mechanism 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
HVJXPDPGPORYKY-UHFFFAOYSA-N methyl 2-bromoprop-2-enoate Chemical compound COC(=O)C(Br)=C HVJXPDPGPORYKY-UHFFFAOYSA-N 0.000 description 1
ZTZJVAOTIOAZGZ-UHFFFAOYSA-N methyl 2-fluoroacrylate Chemical compound COC(=O)C(F)=C ZTZJVAOTIOAZGZ-UHFFFAOYSA-N 0.000 description 1
NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 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
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UIAMCVSNZQYIQS-KTKRTIGZSA-N oleonitrile Chemical compound CCCCCCCC\C=C/CCCCCCCC#N UIAMCVSNZQYIQS-KTKRTIGZSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 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
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920006124 polyolefin elastomer Polymers 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
LSJFMTWFOIHWKQ-UHFFFAOYSA-N prop-1-en-2-yl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)=C LSJFMTWFOIHWKQ-UHFFFAOYSA-N 0.000 description 1
PDBWEHKCAUAROT-UHFFFAOYSA-N prop-1-en-2-yl butanoate Chemical compound CCCC(=O)OC(C)=C PDBWEHKCAUAROT-UHFFFAOYSA-N 0.000 description 1
NLDFTWSUPLJCQD-UHFFFAOYSA-N prop-1-en-2-yl propanoate Chemical compound CCC(=O)OC(C)=C NLDFTWSUPLJCQD-UHFFFAOYSA-N 0.000 description 1
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
OTRMXXQNSIVZNR-UHFFFAOYSA-N prop-2-enyl nitrate Chemical compound [O-][N+](=O)OCC=C OTRMXXQNSIVZNR-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
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
238000007342 radical addition reaction Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
229910052717 sulfur Inorganic materials 0.000 description 1
OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
150000008127 vinyl sulfides Chemical class 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
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/02—Monomers containing chlorine
- C08F14/04—Monomers containing two carbon atoms
- 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Graft Or Block Polymers (AREA)
Polymerisation Methods In General (AREA)

CA270,387A 1976-11-30 1977-01-25 Procede d'obtention de polymeres et de copolymeres d'halogenure de vinyle avec des polyolefines Expired CA1111176A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US746,048		1976-11-30
US05/746,048 US4067928A (en)	1975-01-15	1976-11-30	Method of preparing vinyl halide polymers and copolymers with polyolefins

Publications (1)

Publication Number	Publication Date
CA1111176A true CA1111176A (fr)	1981-10-20

Family

ID=24999283

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA270,387A Expired CA1111176A (fr)	1976-11-30	1977-01-25	Procede d'obtention de polymeres et de copolymeres d'halogenure de vinyle avec des polyolefines

Country Status (11)

Country	Link
JP (1)	JPS6031848B2 (fr)
BE (1)	BE850890A (fr)
BR (1)	BR7700207A (fr)
CA (1)	CA1111176A (fr)
DE (1)	DE2701680A1 (fr)
ES (1)	ES455205A1 (fr)
FR (1)	FR2372180A1 (fr)
GB (1)	GB1568632A (fr)
IT (1)	IT1084901B (fr)
NL (1)	NL7701001A (fr)
SU (1)	SU799672A3 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT987193B (it) *	1972-05-08	1975-02-20	Hooker Chemical Corp	Procedimento di polimerizzazione di cloruro vinilico con polimeri e copolimeri olefinici e loro composizioni

1977
- 1977-01-07 GB GB446479A patent/GB1568632A/en not_active Expired
- 1977-01-12 BR BR7700207A patent/BR7700207A/pt unknown
- 1977-01-17 DE DE19772701680 patent/DE2701680A1/de not_active Ceased
- 1977-01-19 IT IT1942977A patent/IT1084901B/it active
- 1977-01-20 ES ES455205A patent/ES455205A1/es not_active Expired
- 1977-01-25 CA CA270,387A patent/CA1111176A/fr not_active Expired
- 1977-01-25 JP JP762277A patent/JPS6031848B2/ja not_active Expired
- 1977-01-26 SU SU772444853A patent/SU799672A3/ru active
- 1977-01-28 BE BE174499A patent/BE850890A/fr not_active IP Right Cessation
- 1977-01-28 FR FR7702429A patent/FR2372180A1/fr active Granted
- 1977-01-31 NL NL7701001A patent/NL7701001A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IT1084901B (it)	1985-05-28
FR2372180A1 (fr)	1978-06-23
SU799672A3 (ru)	1981-01-23
NL7701001A (nl)	1978-06-01
ES455205A1 (es)	1978-03-16
GB1568632A (en)	1980-06-04
JPS5369294A (en)	1978-06-20
FR2372180B1 (fr)	1983-08-19
DE2701680A1 (de)	1978-06-01
BE850890A (fr)	1977-07-28
JPS6031848B2 (ja)	1985-07-24
BR7700207A (pt)	1978-06-06

Legal Events

Date	Code	Title	Description
1998-10-20	MKEX	Expiry

Publication	Publication Date	Title
US4195137A (en)	1980-03-25	Method of preparing vinyl halide polymers and copolymers with polyolefins
US4028329A (en)	1977-06-07	Process for the bulk polymerization of vinyl halide polymers showing reduced reactor scale formation
US4012460A (en)	1977-03-15	Method of polymerizing vinyl chloride with olefin-acrylic ester copolymers and composition thereof
US4981907A (en)	1991-01-01	Process for the preparation of an acrylate-vinyl chloride graft polymer
US4067928A (en)	1978-01-10	Method of preparing vinyl halide polymers and copolymers with polyolefins
JPH04266905A (ja)	1992-09-22	ビニルポリマー樹脂の重合方法
AU637523B2 (en)	1993-05-27	Preparation of an impact-resistant polyacrylate/vinyl chloride graft copolymer
US4071582A (en)	1978-01-31	Method of polymerizing vinyl halide with olefin polymers and copolymers and compositions thereof
EP0466808B1 (fr)	1996-01-31	Procede de copolymerisation a teneur elevee en solides d'anhydride maleique et d'ether de vinyle d'alcoyle
US4155899A (en)	1979-05-22	Post bulk polymerization process for polyvinyl halide and composition thereof
CA1111176A (fr)	1981-10-20	Procede d'obtention de polymeres et de copolymeres d'halogenure de vinyle avec des polyolefines
US3580975A (en)	1971-05-25	Vinyl halide graft polymers
US4163033A (en)	1979-07-31	Method of polymerizing vinyl halide with olefin polymers and copolymers and compositions thereof
US4137216A (en)	1979-01-30	Post bulk polymerization process for polyvinyl halide and composition thereof
JPH0118082B2 (fr)	1989-04-04
CA1144295A (fr)	1983-04-05	Methode d'homogeneisation pour la formation de polymeres par emulsion-suspension
US3544539A (en)	1970-12-01	Process for the suspension polymerization of vinyl chloride
US3816565A (en)	1974-06-11	Particle size control of bulk polymerized vinyl chloride polymers and copolymers
US3810958A (en)	1974-05-14	Method of obtaining small particle size polymers and copolymers of vinyl chloride by bulk polymerization
CA1102046A (fr)	1981-05-26	Traduction non-disponible
DE2323191C3 (de)	1981-10-15	Verfahren zur Herstellung eines Polymeren aus Vinylhalogenid nach einem Zwei-Stufen-Massenpolymerisationsverfahren
GB1568631A (en)	1980-06-04	Method of preparing vinyl or vinylidene halide polymer products
CA1109181A (fr)	1981-09-15	Methode de polymerisation d'halogenure vinylique avec des polymeres et des copolymeres olefiniques; composes a base de ces produits
US4003962A (en)	1977-01-18	Method of preparing an easy processing polyvinyl halide by an in-process reaction
JPH0225923B2 (fr)	1990-06-06