DE19545609A1 - Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen - Google Patents
Redoxkatalysatorsystem zur Initiierung von EmulsionspolymerisationenInfo
- Publication number
- DE19545609A1 DE19545609A1 DE19545609A DE19545609A DE19545609A1 DE 19545609 A1 DE19545609 A1 DE 19545609A1 DE 19545609 A DE19545609 A DE 19545609A DE 19545609 A DE19545609 A DE 19545609A DE 19545609 A1 DE19545609 A1 DE 19545609A1
- Authority
- DE
- Germany
- Prior art keywords
- redox catalyst
- catalyst system
- sodium
- reducing agent
- bis
- Prior art date
- 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.)
- Withdrawn
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 36
- 238000007720 emulsion polymerization reaction Methods 0.000 title claims description 8
- 230000000977 initiatory effect Effects 0.000 title 1
- 239000006185 dispersion Substances 0.000 claims abstract description 49
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 22
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 229920003023 plastic Polymers 0.000 claims abstract description 14
- 239000004033 plastic Substances 0.000 claims abstract description 14
- 239000007800 oxidant agent Substances 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 239000000839 emulsion Substances 0.000 claims abstract description 4
- 239000004908 Emulsion polymer Substances 0.000 claims abstract description 3
- 125000003172 aldehyde group Chemical group 0.000 claims abstract description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 239000000853 adhesive Substances 0.000 claims description 14
- 230000001070 adhesive effect Effects 0.000 claims description 14
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 14
- 229920001567 vinyl ester resin Polymers 0.000 claims description 13
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229940079826 hydrogen sulfite Drugs 0.000 claims description 10
- 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 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000003292 glue Substances 0.000 claims description 7
- YGZZDQOCTFVBFC-UHFFFAOYSA-L disodium;1,5-dihydroxypentane-1,5-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C(O)CCCC(O)S([O-])(=O)=O YGZZDQOCTFVBFC-UHFFFAOYSA-L 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 230000027455 binding Effects 0.000 claims 1
- 238000009739 binding Methods 0.000 claims 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 31
- 150000001299 aldehydes Chemical class 0.000 abstract description 18
- 239000000178 monomer Substances 0.000 abstract description 17
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract description 8
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 abstract description 5
- 238000004132 cross linking Methods 0.000 abstract description 4
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 alkyl hydroperoxides Chemical class 0.000 description 12
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 12
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 11
- 239000000084 colloidal system Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229920001290 polyvinyl ester Polymers 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 6
- 238000004026 adhesive bonding Methods 0.000 description 6
- 229940015043 glyoxal Drugs 0.000 description 6
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000010262 sodium metabisulphite Nutrition 0.000 description 5
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229960000587 glutaral Drugs 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 3
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 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
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000011111 cardboard Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000010985 leather 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
- 239000011976 maleic acid Substances 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 125000005385 peroxodisulfate group Chemical group 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- GOPSAMYJSPYXPL-UHFFFAOYSA-N prop-2-enyl n-(hydroxymethyl)carbamate Chemical compound OCNC(=O)OCC=C GOPSAMYJSPYXPL-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 229910001428 transition metal ion Inorganic materials 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- XTUAWCZYONBWON-UHFFFAOYSA-N 1-ethylimidazolidin-2-one;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCN1CCNC1=O XTUAWCZYONBWON-UHFFFAOYSA-N 0.000 description 1
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-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
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 description 1
- VTERBIYJBWDXDT-UHFFFAOYSA-N 2-hydroxybutanedial Chemical compound O=CC(O)CC=O VTERBIYJBWDXDT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BXAAQNFGSQKPDZ-UHFFFAOYSA-N 3-[1,2,2-tris(prop-2-enoxy)ethoxy]prop-1-ene Chemical compound C=CCOC(OCC=C)C(OCC=C)OCC=C BXAAQNFGSQKPDZ-UHFFFAOYSA-N 0.000 description 1
- UIVALZXFWDRKKE-UHFFFAOYSA-N 3-hydroxypentanedial Chemical compound O=CCC(O)CC=O UIVALZXFWDRKKE-UHFFFAOYSA-N 0.000 description 1
- LUNMJPAJHJAGIS-UHFFFAOYSA-N 3-methylpentanedial Chemical compound O=CCC(C)CC=O LUNMJPAJHJAGIS-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-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
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920002085 Dialdehyde starch Polymers 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
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- 150000002927 oxygen compounds Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
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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
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19545609A DE19545609A1 (de) | 1995-12-07 | 1995-12-07 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
| EP96119133A EP0778290B1 (de) | 1995-12-07 | 1996-11-29 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
| DE59602433T DE59602433D1 (de) | 1995-12-07 | 1996-11-29 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
| ES96119133T ES2135154T3 (es) | 1995-12-07 | 1996-11-29 | Sistema catalizador redox para la iniciacion de polimerizaciones en emulsion. |
| AT96119133T ATE182155T1 (de) | 1995-12-07 | 1996-11-29 | Redoxkatalysatorsystem zur initiierung von emulsionspolymerisationen |
| US08/759,831 US5744418A (en) | 1995-12-07 | 1996-12-04 | Redox catalyst system for the initiation of emulsion polymerization |
| JP32720696A JP4121097B2 (ja) | 1995-12-07 | 1996-12-06 | 乳化重合を開始するためのレドックス触媒系 |
| US09/067,840 US5969065A (en) | 1995-12-07 | 1998-04-27 | Redox catalyst system for the initiation of emulsion polymerization |
| GR990402486T GR3031395T3 (en) | 1995-12-07 | 1999-09-30 | Redox catalyst for the initiation of emulsion polymerization |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19545609A DE19545609A1 (de) | 1995-12-07 | 1995-12-07 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19545609A1 true DE19545609A1 (de) | 1997-06-12 |
Family
ID=7779409
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19545609A Withdrawn DE19545609A1 (de) | 1995-12-07 | 1995-12-07 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
| DE59602433T Expired - Lifetime DE59602433D1 (de) | 1995-12-07 | 1996-11-29 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59602433T Expired - Lifetime DE59602433D1 (de) | 1995-12-07 | 1996-11-29 | Redoxkatalysatorsystem zur Initiierung von Emulsionspolymerisationen |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5744418A (enExample) |
| EP (1) | EP0778290B1 (enExample) |
| JP (1) | JP4121097B2 (enExample) |
| AT (1) | ATE182155T1 (enExample) |
| DE (2) | DE19545609A1 (enExample) |
| ES (1) | ES2135154T3 (enExample) |
| GR (1) | GR3031395T3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10241481B4 (de) * | 2002-09-07 | 2006-07-06 | Celanese Emulsions Gmbh | Verfahren zum Herstellen von wässrigen Polymerdispersionen mit sehr niedrigen Restmonomergehalten und deren Verwendung |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1276816B1 (it) * | 1995-10-04 | 1997-11-03 | Atochem Elf Italia | Emulsione a basso voc |
| DE19636510A1 (de) | 1996-09-09 | 1998-03-12 | Clariant Gmbh | Polyvinylalkohol-Kompositionen |
| DE19851024A1 (de) * | 1998-11-05 | 2000-05-11 | Basf Ag | Wäßrige Dispersionen von wasserlöslichen Polymerisaten von N-Vinylcarbonsäureamiden, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19857897A1 (de) * | 1998-12-15 | 2000-06-21 | Basf Ag | Verfahren zur Herstellung wäßriger Polymerdispersionen |
| JP2000212533A (ja) * | 1999-01-20 | 2000-08-02 | Sumitomo Chem Co Ltd | 接着剤組成物 |
| DE19927278C1 (de) * | 1999-06-15 | 2000-12-14 | Siemens Audiologische Technik | Verfahren zum Anpassen eines Hörhilfegeräts sowie Hörhilfegerät |
| US6379499B1 (en) | 1999-09-28 | 2002-04-30 | University Of Georgia Research Foundation, Inc. | Polymer-aldehyde additives to improve paper properties |
| JP4379998B2 (ja) * | 1999-09-30 | 2009-12-09 | 住友化学株式会社 | エチレン−酢酸ビニル系共重合体水性エマルジョンの製造方法 |
| DE10064085A1 (de) | 2000-12-21 | 2002-07-04 | Consortium Elektrochem Ind | Verfahren zur Entfernung von freien Aldehyden |
| DE10163586A1 (de) * | 2001-12-21 | 2003-07-03 | Clariant Gmbh | Verwendung von weichmacherfreien, wässrigen copolymeren Poly(vinylester)- Dispersionen in Lebensmittelbeschichtungsmassen |
| DE10320904A1 (de) * | 2003-05-09 | 2004-11-25 | Cognis Deutschland Gmbh & Co. Kg | Startersysteme II |
| DE10333623A1 (de) * | 2003-07-24 | 2005-02-24 | Celanese Emulsions Gmbh | Beschichtungszusammensetzung und Verfahren zu deren Herstellung |
| DE102005032194B4 (de) | 2005-07-09 | 2008-11-27 | Celanese Emulsions Gmbh | Wässrige Kunststoff-Dispersionen, Verfahren zu deren Herstellung sowie deren Verwendung |
| DE102006030557A1 (de) * | 2006-07-03 | 2008-01-10 | Celanese Emulsions Gmbh | Verfahren zur Herstellung wässriger Vinylester-Dispersionen |
| EP2125903B1 (en) * | 2006-07-18 | 2014-01-15 | Celanese International Corporation | Emulsion polymerisation process |
| DE102007033595A1 (de) | 2007-07-19 | 2009-01-22 | Celanese Emulsions Gmbh | Polyvinylesterdispersionen, Verfahren zu deren Herstellung und deren Verwendung |
| DE102007033596A1 (de) | 2007-07-19 | 2009-01-22 | Celanese Emulsions Gmbh | Beschichtungsmittel mit hoher Bewitterungsbeständigkeit, Verfahren zu deren Herstellung und deren Verwendung |
| US20100167611A1 (en) * | 2008-12-29 | 2010-07-01 | Mclennan Alistair John | Vinyl acetate / aromatic vinyl ester copolymer binder resins |
| KR101656542B1 (ko) * | 2009-01-14 | 2016-09-09 | 트린세오 유럽 게엠베하 | 에멀젼 중합에서의 단량체 전환율 증가 |
| US8440766B2 (en) | 2010-07-28 | 2013-05-14 | Celanese Emulsions Gmbh | Heterogeneous vinyl acetate based copolymers as binder for paints |
| EP2431396B1 (en) | 2010-09-15 | 2016-07-27 | Celanese Sales Germany GmbH | Vinyl acetate based alkaline resistant scrim binder |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3438941A (en) * | 1967-10-16 | 1969-04-15 | Nalco Chemical Co | Homopolymerization of acrolein in aqueous monomer emulsion via redox catalyst |
| JPS6010138B2 (ja) | 1975-10-31 | 1985-03-15 | 住友化学工業株式会社 | 不織布 |
| JPS588410B2 (ja) * | 1975-11-04 | 1983-02-16 | 住友化学工業株式会社 | スイセイブンサンエキノ セイゾウホウホウ |
| DE2620738C2 (de) | 1976-05-11 | 1983-04-28 | Wacker-Chemie GmbH, 8000 München | Verfahren zur Herstellung wäßriger Copolymerdispersionen und deren Verwendung in Vermischung mit sauren, wasserlöslichen Härtezusätzen für Klebemittel |
| US4360632A (en) | 1981-10-23 | 1982-11-23 | Air Products And Chemicals, Inc. | Ketone bisulfites as reducing agent for free radical polymerization |
| JPS6099096A (ja) | 1984-10-12 | 1985-06-01 | 住友化学工業株式会社 | 含浸紙 |
| DE3521618A1 (de) * | 1985-06-15 | 1986-12-18 | Bayer Ag, 5090 Leverkusen | In wasser dispergierbare polyisocyanat-zubereitung und ihre verwendung als zusatzmittel fuer waessrige klebstoffe |
| DK0394774T3 (da) | 1989-04-26 | 1996-02-19 | Nat Starch Chem Invest | Forbedrede klæbestoffer til træarbejde baseret på multitrinsemulitionspolymer |
| DE3942628A1 (de) * | 1989-12-22 | 1991-06-27 | Wacker Chemie Gmbh | Verwendung waessriger copolymerdispersionen unter zusatz von sauren metallsalzen oder freien saeuren als klebemittel |
| US5434216A (en) | 1993-05-07 | 1995-07-18 | National Starch And Chemical Investment Holding Corporation | Woodworking latex adhesives with improved water, heat and creep resistance |
| DE4420484C2 (de) | 1994-06-11 | 1999-02-04 | Clariant Gmbh | Wäßriger Dispersionsklebstoff auf Polyvinylester-Basis, Verfahren zur Herstellung sowie dessen Verwendung |
-
1995
- 1995-12-07 DE DE19545609A patent/DE19545609A1/de not_active Withdrawn
-
1996
- 1996-11-29 EP EP96119133A patent/EP0778290B1/de not_active Expired - Lifetime
- 1996-11-29 ES ES96119133T patent/ES2135154T3/es not_active Expired - Lifetime
- 1996-11-29 DE DE59602433T patent/DE59602433D1/de not_active Expired - Lifetime
- 1996-11-29 AT AT96119133T patent/ATE182155T1/de not_active IP Right Cessation
- 1996-12-04 US US08/759,831 patent/US5744418A/en not_active Expired - Lifetime
- 1996-12-06 JP JP32720696A patent/JP4121097B2/ja not_active Expired - Lifetime
-
1998
- 1998-04-27 US US09/067,840 patent/US5969065A/en not_active Expired - Lifetime
-
1999
- 1999-09-30 GR GR990402486T patent/GR3031395T3/el unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10241481B4 (de) * | 2002-09-07 | 2006-07-06 | Celanese Emulsions Gmbh | Verfahren zum Herstellen von wässrigen Polymerdispersionen mit sehr niedrigen Restmonomergehalten und deren Verwendung |
| US7244812B2 (en) | 2002-09-07 | 2007-07-17 | Celanese Emulsions Gmbh | Method for the production of aqueous polymer dispersions containing very few residual monomers and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0778290B1 (de) | 1999-07-14 |
| US5969065A (en) | 1999-10-19 |
| EP0778290A3 (de) | 1997-09-10 |
| JPH09176217A (ja) | 1997-07-08 |
| GR3031395T3 (en) | 2000-01-31 |
| EP0778290A2 (de) | 1997-06-11 |
| ATE182155T1 (de) | 1999-07-15 |
| JP4121097B2 (ja) | 2008-07-16 |
| DE59602433D1 (de) | 1999-08-19 |
| US5744418A (en) | 1998-04-28 |
| ES2135154T3 (es) | 1999-10-16 |
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