CA1142294A - Ethers vinyliques, methode de preparation et utilisation pour l'obtention de polymeres - Google Patents

Ethers vinyliques, methode de preparation et utilisation pour l'obtention de polymeres

Info

Publication number: CA1142294A
Authority: CA; Canada
Prior art keywords: group; component; polymer according; solution; methyl
Prior art date: 1977-07-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000377343A

Other languages

English (en)

Inventor

Sameer H. Eldin

Friedrich Stockinger

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1977-07-07

Filing date

1981-05-11

Publication date

1983-03-01

1977-07-07 Priority claimed from CH843377A external-priority patent/CH633779A5/de

1981-05-11 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1981-05-11 Priority to CA000377343A priority Critical patent/CA1142294A/fr

1983-03-01 Application granted granted Critical

1983-03-01 Publication of CA1142294A publication Critical patent/CA1142294A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 30
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims description 13
238000000034 method Methods 0.000 title description 11
238000002360 preparation method Methods 0.000 title description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
-1 hydantoin vinyl ethers Chemical class 0.000 claims abstract description 15
229940091173 hydantoin Drugs 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 8
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 31
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 28
150000008064 anhydrides Chemical class 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 12
239000003795 chemical substances by application Substances 0.000 abstract description 9
239000002562 thickening agent Substances 0.000 abstract description 4
239000011230 binding agent Substances 0.000 abstract description 3
239000013008 thixotropic agent Substances 0.000 abstract description 3
239000003381 stabilizer Substances 0.000 abstract description 2
239000008139 complexing agent Substances 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 62
229920001577 copolymer Polymers 0.000 description 49
239000000203 mixture Substances 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
150000003863 ammonium salts Chemical class 0.000 description 21
239000000047 product Substances 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
150000001408 amides Chemical class 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
229910052757 nitrogen Inorganic materials 0.000 description 18
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
239000004342 Benzoyl peroxide Substances 0.000 description 13
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 13
235000019400 benzoyl peroxide Nutrition 0.000 description 13
229920001897 terpolymer Polymers 0.000 description 13
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
238000003756 stirring Methods 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000008096 xylene Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
230000003068 static effect Effects 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 6
239000001267 polyvinylpyrrolidone Substances 0.000 description 6
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
229940093956 potassium carbonate Drugs 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
230000008719 thickening Effects 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000005690 diesters Chemical class 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000011630 iodine Substances 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
239000000306 component Substances 0.000 description 4
239000003431 cross linking reagent Substances 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000002453 shampoo Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000007858 starting material Substances 0.000 description 4
NPSGIMOZNMNEAP-UHFFFAOYSA-N 1-(2-ethenoxyethyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(CCOC=C)C(=O)NC1=O NPSGIMOZNMNEAP-UHFFFAOYSA-N 0.000 description 3
ZUWLNOXNQWRSHI-UHFFFAOYSA-N 3-(2-ethenoxyethyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)NC(=O)N(CCOC=C)C1=O ZUWLNOXNQWRSHI-UHFFFAOYSA-N 0.000 description 3
UUQALTUYZNNAET-UHFFFAOYSA-N 3-(2-ethenoxyethyl)imidazolidine-2,4-dione Chemical compound C=COCCN1C(=O)CNC1=O UUQALTUYZNNAET-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000470 constituent Substances 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
150000003949 imides Chemical class 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000004753 textile Substances 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
238000010792 warming Methods 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 2
HOJYCNSTMZLRCV-UHFFFAOYSA-N 5,5-dimethyl-3-prop-2-enylimidazolidine-2,4-dione Chemical compound CC1(C)NC(=O)N(CC=C)C1=O HOJYCNSTMZLRCV-UHFFFAOYSA-N 0.000 description 2
VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
230000000536 complexating effect Effects 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003822 epoxy resin Substances 0.000 description 2
150000002169 ethanolamines Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
239000000463 material Substances 0.000 description 2
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
229920002239 polyacrylonitrile Polymers 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
235000007686 potassium Nutrition 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
OKLWGALVQNNLCI-IWQZZHSRSA-N (e)-2-(chloromethyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(\CCl)C(O)=O OKLWGALVQNNLCI-IWQZZHSRSA-N 0.000 description 1
BGKDZDYQQWNGIR-BQYQJAHWSA-N (e)-2-bromo-3-phenylbut-2-enedioic acid Chemical compound OC(=O)C(\Br)=C(/C(O)=O)C1=CC=CC=C1 BGKDZDYQQWNGIR-BQYQJAHWSA-N 0.000 description 1
PNNFEYPWPCDLOC-UPHRSURJSA-N (z)-2,3-dichlorobut-2-enedioic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C(O)=O PNNFEYPWPCDLOC-UPHRSURJSA-N 0.000 description 1
QQCYMGFLVZNQQO-YPKPFQOOSA-N (z)-2,3-diphenylbut-2-enedioic acid Chemical compound C=1C=CC=CC=1/C(C(=O)O)=C(/C(O)=O)C1=CC=CC=C1 QQCYMGFLVZNQQO-YPKPFQOOSA-N 0.000 description 1
JWPVCFSBPUPIQA-WAYWQWQTSA-N (z)-2-butylbut-2-enedioic acid Chemical compound CCCC\C(C(O)=O)=C\C(O)=O JWPVCFSBPUPIQA-WAYWQWQTSA-N 0.000 description 1
SASYHUDIOGGZCN-ARJAWSKDSA-N (z)-2-ethylbut-2-enedioic acid Chemical compound CC\C(C(O)=O)=C\C(O)=O SASYHUDIOGGZCN-ARJAWSKDSA-N 0.000 description 1
CQNPSIAJXGEDQS-VURMDHGXSA-N (z)-2-phenylbut-2-enedioic acid Chemical compound OC(=O)\C=C(/C(O)=O)C1=CC=CC=C1 CQNPSIAJXGEDQS-VURMDHGXSA-N 0.000 description 1
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 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
NERNEXMEYQFFHU-UHFFFAOYSA-N 1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCCCC1 NERNEXMEYQFFHU-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
FSRLCYXRDZIJJT-UHFFFAOYSA-N 1-ethenyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(C=C)CCCC2=C1 FSRLCYXRDZIJJT-UHFFFAOYSA-N 0.000 description 1
JADALHRUMHUJBX-UHFFFAOYSA-N 1-ethyl-5,5-dimethylimidazolidine-2,4-dione Chemical compound CCN1C(=O)NC(=O)C1(C)C JADALHRUMHUJBX-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
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150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000008394 flocculating agent Substances 0.000 description 1
UPBDXRPQPOWRKR-UHFFFAOYSA-N furan-2,5-dione;methoxyethene Chemical compound COC=C.O=C1OC(=O)C=C1 UPBDXRPQPOWRKR-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
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150000002730 mercury Chemical class 0.000 description 1
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229910021645 metal ion Inorganic materials 0.000 description 1
229920000609 methyl cellulose Polymers 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
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LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
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238000010422 painting Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
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229920001223 polyethylene glycol Polymers 0.000 description 1
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239000005056 polyisocyanate Substances 0.000 description 1
150000008442 polyphenolic compounds Chemical class 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012966 redox initiator Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229940102098 revolution Drugs 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000004513 sizing Methods 0.000 description 1
XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000003351 stiffener Substances 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
238000004381 surface treatment Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000271 synthetic detergent Substances 0.000 description 1
RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
229960001296 zinc oxide Drugs 0.000 description 1

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

CA000377343A 1977-07-07 1981-05-11 Ethers vinyliques, methode de preparation et utilisation pour l'obtention de polymeres Expired CA1142294A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000377343A CA1142294A (fr)	1977-07-07	1981-05-11	Ethers vinyliques, methode de preparation et utilisation pour l'obtention de polymeres

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH8433/77		1977-07-07
CH843377A CH633779A5 (de)	1977-07-07	1977-07-07	Verfahren zur herstellung neuer vinylaether und deren verwendung zur herstellung von polymeren.
CA306,892A CA1115711A (fr)	1977-07-07	1978-07-06	Procede d'obtention d'ethers de vinyle
CA000377343A CA1142294A (fr)	1977-07-07	1981-05-11	Ethers vinyliques, methode de preparation et utilisation pour l'obtention de polymeres

Publications (1)

Publication Number	Publication Date
CA1142294A true CA1142294A (fr)	1983-03-01

Family

ID=27165740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000377343A Expired CA1142294A (fr)	1977-07-07	1981-05-11	Ethers vinyliques, methode de preparation et utilisation pour l'obtention de polymeres

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CA (1)	CA1142294A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116814201A (zh) *	2023-06-12	2023-09-29	三联泵业股份有限公司	一种海洋工程疏浚泵消失模铸造用泡沫塑料粘结剂

1981
- 1981-05-11 CA CA000377343A patent/CA1142294A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116814201A (zh) *	2023-06-12	2023-09-29	三联泵业股份有限公司	一种海洋工程疏浚泵消失模铸造用泡沫塑料粘结剂
CN116814201B (zh) *	2023-06-12	2025-10-17	三联泵业股份有限公司	一种海洋工程疏浚泵消失模铸造用泡沫塑料粘结剂

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Publication	Publication Date	Title
US4338239A (en)	1982-07-06	Polyacrylate thickening agents
EP0172450B1 (fr)	1990-10-24	Compositions polymères à phases cristallines liquides
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CA1331072C (fr)	1994-07-26	Methode de preparation de sels metalliques contenant des polymeres a teneur en carboxyle
DE1768245A1 (de)	1972-01-27	Anhydrid-Interpolymere als Verdickungsmittel und Verfahren zu ihrer Herstellung
EP3087109B1 (fr)	2018-08-29	Compositions aqueuses solubles de polymères d'acide polyitaconique sélectionnés
US4585846A (en)	1986-04-29	Cyclopolymerizable sulfobetaine monomer
EP0146277A2 (fr)	1985-06-26	Produits cellulosiques
US4206309A (en)	1980-06-03	Vinyl ethers, process for their preparation, and their use for the preparation of polymers
EP0421185B1 (fr)	1994-08-10	Copolymère polyacrylate, dispersion de polyacrylate contenant un copolymère polyacrylate et procédé pour sa préparation
US3444143A (en)	1969-05-13	Decarboxylated polymeric carboxylic acid
US3450674A (en)	1969-06-17	Poly-n-heterocyclics and method
US5011895A (en)	1991-04-30	Precipitation polymerization of copolymers of a vinyl lactam and a polymerizable carboxylic acid using sub-surface feeding
Nazarova et al.	1992	Copolymerizations of N-vinylpyrrolidone and activated esters of unsaturated acids
EP0467959A4 (en)	1992-09-23	Precipitation polymerization of copolymers of a vinyl lactam and a polymerizable carboxylic acid in an aliphatic hydrocarbon solvent
CA2023213A1 (fr)	1991-03-06	Polymeres d'oxyde d'alkyle et de vinyle, renfermant une fonction lactame
Bonnans-Plaisance et al.	1992	Functional polythiiranes: 2. Polymers of methyl (2, 3-epithiopropyl-thio) ethanoate
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US4980419A (en)	1990-12-25	Alkyl vinyl ether polymers containing a lactam functionality
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GB2094811A (en)	1982-09-22	Preparation of polymers of hydantoin vinyl ethers of definite viscosities
Chen et al.	1987	Graft copolymers of para‐hydroxybenzoic acid (PHB). I. A general method for grafting mesogenic oligo‐PHB to oligomers
WO1993019098A1 (fr)	1993-09-30	Polymerisation par precipitation de copolymeres d'un lactame de vinyle et d'un acide carboxylique polymerisable et solubilisation de ceux-ci
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