LU82908A1 - Catalyseurs et procede pour la preparation de polymeres et de copolymeres de chlorure de vinyle - Google Patents

Catalyseurs et procede pour la preparation de polymeres et de copolymeres de chlorure de vinyle Download PDF

Info

Publication number: LU82908A1
Authority: LU; Luxembourg
Prior art keywords: stannous; polymerization; vinyl chloride; chosen; antimony
Prior art date: 1979-12-21

Application number

LU82908A

Other languages

English (en)

French (fr)

Inventor

N Gaylord

M Nagler

Original Assignee

Dart Ind Inc

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.)

1979-12-21

Filing date

1980-11-04

Publication date

1981-03-24

1980-11-04 Application filed by Dart Ind Inc filed Critical Dart Ind Inc

1981-03-24 Publication of LU82908A1 publication Critical patent/LU82908A1/fr

Links

BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims description 50
238000000034 method Methods 0.000 title claims description 34
230000008569 process Effects 0.000 title claims description 20
229920000642 polymer Polymers 0.000 title claims description 10
229920001577 copolymer Polymers 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 5
239000003054 catalyst Substances 0.000 title description 12
238000006116 polymerization reaction Methods 0.000 claims description 39
239000003638 chemical reducing agent Substances 0.000 claims description 26
239000008139 complexing agent Substances 0.000 claims description 21
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 16
-1 antimony carboxylates Chemical class 0.000 claims description 12
150000007942 carboxylates Chemical class 0.000 claims description 11
239000012933 diacyl peroxide Substances 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
239000000725 suspension Substances 0.000 claims description 11
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 9
229940070765 laurate Drugs 0.000 claims description 9
238000012662 bulk polymerization Methods 0.000 claims description 8
230000003197 catalytic effect Effects 0.000 claims description 6
229920000915 polyvinyl chloride Polymers 0.000 claims description 6
239000004800 polyvinyl chloride Substances 0.000 claims description 6
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 claims description 6
FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical class [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 claims description 5
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
229910052787 antimony Inorganic materials 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
239000004014 plasticizer Substances 0.000 claims description 4
239000004342 Benzoyl peroxide Substances 0.000 claims description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims 1
TXTQARDVRPFFHL-UHFFFAOYSA-N [Sb].[H][H] Chemical compound [Sb].[H][H] TXTQARDVRPFFHL-UHFFFAOYSA-N 0.000 claims 1
150000001733 carboxylic acid esters Chemical class 0.000 claims 1
JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 claims 1
CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 23
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 14
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 14
239000000178 monomer Substances 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 10
238000010557 suspension polymerization reaction Methods 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 7
150000002430 hydrocarbons Chemical group 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003999 initiator Substances 0.000 description 5
125000002015 acyclic group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000011521 glass Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
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 3
150000003839 salts Chemical class 0.000 description 3
238000007789 sealing Methods 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
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 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
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 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
229920003091 Methocel™ Polymers 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
BRWZYZWZBMGMMG-UHFFFAOYSA-J dodecanoate tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O BRWZYZWZBMGMMG-UHFFFAOYSA-J 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012634 fragment Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
WTJKUFMLQFLJOT-UHFFFAOYSA-N heptadecan-9-one Chemical compound CCCCCCCCC(=O)CCCCCCCC WTJKUFMLQFLJOT-UHFFFAOYSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
150000002976 peresters Chemical class 0.000 description 2
150000003014 phosphoric acid esters Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
239000001119 stannous chloride Substances 0.000 description 2
235000011150 stannous chloride Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000004448 titration Methods 0.000 description 2
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
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
KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
RQHGZNBWBKINOY-PLNGDYQASA-N (z)-4-tert-butylperoxy-4-oxobut-2-enoic acid Chemical compound CC(C)(C)OOC(=O)\C=C/C(O)=O RQHGZNBWBKINOY-PLNGDYQASA-N 0.000 description 1
AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
DSCFFEYYQKSRSV-UHFFFAOYSA-N 1L-O1-methyl-muco-inositol Natural products COC1C(O)C(O)C(O)C(O)C1O DSCFFEYYQKSRSV-UHFFFAOYSA-N 0.000 description 1
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 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
SZFABAXZLWVKDV-UHFFFAOYSA-N 2-methyloctanoyl 2-methyloctaneperoxoate Chemical compound CCCCCCC(C)C(=O)OOC(=O)C(C)CCCCCC SZFABAXZLWVKDV-UHFFFAOYSA-N 0.000 description 1
LWXMGLYFVTUYCT-UHFFFAOYSA-N 2-methylpropyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)COOC(=O)C(C)(C)C LWXMGLYFVTUYCT-UHFFFAOYSA-N 0.000 description 1
PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
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 1
239000005569 Iron sulphate Substances 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 1
UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical group CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Substances Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 1
VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
QZYRMODBFHTNHF-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QZYRMODBFHTNHF-UHFFFAOYSA-N 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
QFOJTGAPBXCVOK-UHFFFAOYSA-N hexyl 2-ethylhexaneperoxoate Chemical compound CCCCCCOOC(=O)C(CC)CCCC QFOJTGAPBXCVOK-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 1
125000005474 octanoate group Chemical group 0.000 description 1
239000003921 oil Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
239000001230 potassium iodate Substances 0.000 description 1
229940093930 potassium iodate Drugs 0.000 description 1
235000006666 potassium iodate Nutrition 0.000 description 1
RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
229940043349 potassium metabisulfite Drugs 0.000 description 1
235000010263 potassium metabisulphite Nutrition 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000006479 redox reaction Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
229960003010 sodium sulfate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
238000009331 sowing Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
UWNNZXDNLPNGQJ-UHFFFAOYSA-N tert-butyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(C)(C)C UWNNZXDNLPNGQJ-UHFFFAOYSA-N 0.000 description 1
NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- C08F14/06—Vinyl chloride

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polymerization Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

LU82908A 1979-12-21 1980-11-04 Catalyseurs et procede pour la preparation de polymeres et de copolymeres de chlorure de vinyle LU82908A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10632579		1979-12-21
US06/106,325 US4269956A (en)	1979-12-21	1979-12-21	Peroxygen compound-metal carboxylate redox catalyst system for vinyl chloride polymerization

Publications (1)

Publication Number	Publication Date
LU82908A1 true LU82908A1 (fr)	1981-03-24

Family

ID=22310797

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82908A LU82908A1 (fr)	1979-12-21	1980-11-04	Catalyseurs et procede pour la preparation de polymeres et de copolymeres de chlorure de vinyle

Country Status (14)

Country	Link
US (1)	US4269956A (pt)
JP (1)	JPS5693712A (pt)
BE (1)	BE886226A (pt)
BR (1)	BR8007736A (pt)
CA (1)	CA1159814A (pt)
DE (1)	DE3048079A1 (pt)
ES (1)	ES497959A0 (pt)
FR (1)	FR2471991B1 (pt)
GB (1)	GB2065677B (pt)
IT (1)	IT1149275B (pt)
LU (1)	LU82908A1 (pt)
NL (1)	NL8006903A (pt)
NO (1)	NO803574L (pt)
SE (1)	SE8009009L (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0094160B1 (en) *	1982-05-06	1986-07-16	Imperial Chemical Industries Plc	Vinyl chloride polymerisation process
US4981662A (en) *	1990-06-01	1991-01-01	Fmc Corporation	Stabilized hydrogen peroxide
US7026029B2 (en) *	2001-06-05	2006-04-11	Lindholm Edward P	Reactive materials for limited play optical devices and methods of making same
US20060136947A1 (en) *	2004-11-12	2006-06-22	Flexplay Technologies, Inc.	Optical media, read inhibiting agents and methods of making and using same

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL59535C (pt) *	1941-12-31
US2981724A (en) *	1957-05-06	1961-04-25	Escambia Chem Corp	Suspension polymerization of vinyl chloride
US2996490A (en) *	1959-05-12	1961-08-15	Firestone Tire & Rubber Co	Suspension polymerization process and novel compounds for use in said process
NL280042A (pt) *	1961-06-22
FR1486471A (fr) *	1966-05-17	1967-06-30	Rhone Poulenc Sa	Procédé de polymérisation de l'acrylonitrile et système initiateur pour sa mise en oeuvre
US3739043A (en) *	1971-11-18	1973-06-12	Du Pont	Low temperature polymerization process
US3739044A (en) *	1971-12-09	1973-06-12	Du Pont	Low temperature polymerization process and initiating system
US3985718A (en) *	1973-04-24	1976-10-12	Rhone-Poulenc S.A.	Polymerization of olefinic monomers using a four component initiator
US4091197A (en) *	1973-06-08	1978-05-23	Nicolas Fischer	Process for polymerization of vinyl chloride micro-suspension with metal compounds
JPS5345836B2 (pt) *	1974-04-26	1978-12-09

1979
- 1979-12-21 US US06/106,325 patent/US4269956A/en not_active Expired - Lifetime
1980
- 1980-10-30 CA CA000363665A patent/CA1159814A/en not_active Expired
- 1980-10-30 FR FR8023230A patent/FR2471991B1/fr not_active Expired
- 1980-11-04 LU LU82908A patent/LU82908A1/fr unknown
- 1980-11-18 BE BE0/202846A patent/BE886226A/fr not_active IP Right Cessation
- 1980-11-26 NO NO803574A patent/NO803574L/no unknown
- 1980-11-27 BR BR8007736A patent/BR8007736A/pt unknown
- 1980-12-16 JP JP17663080A patent/JPS5693712A/ja active Pending
- 1980-12-16 GB GB8040188A patent/GB2065677B/en not_active Expired
- 1980-12-19 SE SE8009009A patent/SE8009009L/ not_active Application Discontinuation
- 1980-12-19 ES ES497959A patent/ES497959A0/es active Granted
- 1980-12-19 NL NL8006903A patent/NL8006903A/nl not_active Application Discontinuation
- 1980-12-19 IT IT26828/80A patent/IT1149275B/it active
- 1980-12-19 DE DE19803048079 patent/DE3048079A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
NO803574L (no)	1981-06-22
ES8200902A1 (es)	1981-11-16
BR8007736A (pt)	1981-06-23
US4269956A (en)	1981-05-26
JPS5693712A (en)	1981-07-29
BE886226A (fr)	1981-03-16
IT1149275B (it)	1986-12-03
NL8006903A (nl)	1981-07-16
CA1159814A (en)	1984-01-03
GB2065677A (en)	1981-07-01
ES497959A0 (es)	1981-11-16
SE8009009L (sv)	1981-06-22
IT8026828A0 (it)	1980-12-19
GB2065677B (en)	1983-09-21
DE3048079A1 (de)	1981-10-01
FR2471991B1 (fr)	1985-10-11
FR2471991A1 (fr)	1981-06-26

Publication	Publication Date	Title
CA2344824C (en)	2008-02-12	Continuous dosing of very fast initiators during polymerization reactions
CA2441807C (fr)	2009-05-12	Polymerisation en suspension aqueuse du chlorure de vinyle
LU82908A1 (fr)	1981-03-24	Catalyseurs et procede pour la preparation de polymeres et de copolymeres de chlorure de vinyle
KR101147877B1 (ko)	2012-05-25	(코)폴리머를 제조하기 위한 중합 방법
EP2807197B1 (fr)	2021-04-28	Procede de preparation de polymeres halogenes
LU82891A1 (fr)	1981-03-24	Compositions et procede pour la preparation de polymeres et de copolymeres de monomeres ethyleniquement insatures
LU82904A1 (fr)	1981-03-24	Catalyseurs et procede pour la preparation de polymeres et de copolymeres de monomeres ethyleniquement insatures
US4543401A (en)	1985-09-24	Peroxygen compound-isoascorbic acid redox catalyst system for suspension polymerization of vinyl chloride
LU82905A1 (fr)	1981-03-24	Procede et compositions pour la preparation de polymeres et de copolymeres de chlorure de vinyle
US3652522A (en)	1972-03-28	Process for the polymerization of vinyl chloride
FR2471987A1 (fr)	1981-06-26	Catalyseurs et procede pour la preparation de polymeres et de copolymeres d'halogenures de vinyle
EP0100741A1 (fr)	1984-02-15	Procédé de stabilisation de polymères à base de chlorure de vinyle
US4382133A (en)	1983-05-03	Peroxygen compound-6-O-alkanoylisoascorbic acid redox catalyst system for suspension polymerization of vinyl chloride
CN1085676C (zh)	2002-05-29	过氧酸作为分子量调节剂的应用
FR2596763A1 (fr)	1987-10-09	Procede de preparation en microsuspension de latex d'homo- et copolymeres du chlorure de vinyle utilisables comme produits d'ensemencement
LU82920A1 (fr)	1981-03-26	Compositions et procede de preparation de polymeres et de copolymeres de chlorure de vinyle
FR2858319A1 (fr)	2005-02-04	Procede de preparation de substances organiques iodees de faible masse moleculaire et substances organiques iodees de faible masse moleculaire
CA1279943C (fr)	1991-02-05	Procede de preparation en microsuspension de latex d'homo- et co-polymeres du chlorure de vinyle utilisables comme produits d'ensemencement
FR2587031A1 (fr)	1987-03-13	Procede de preparation en microsuspension de latex d'homo- et copolymeres du chlorure de vinyle utilisables comme produits d'ensemencement