DE1264781B - Verfahren zur Polymerisation von Vinylmonomeren - Google Patents
Verfahren zur Polymerisation von VinylmonomerenInfo
- Publication number
- DE1264781B DE1264781B DE1962G0036756 DEG0036756A DE1264781B DE 1264781 B DE1264781 B DE 1264781B DE 1962G0036756 DE1962G0036756 DE 1962G0036756 DE G0036756 A DEG0036756 A DE G0036756A DE 1264781 B DE1264781 B DE 1264781B
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- substituent
- phosphine derivative
- thpc
- hydrogen
- 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.)
- Pending
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 8
- 229920002554 vinyl polymer Polymers 0.000 title claims description 8
- 239000000178 monomer Substances 0.000 title claims description 7
- 150000003003 phosphines Chemical class 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- AKXUUJCMWZFYMV-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;chloride Chemical compound [Cl-].OC[P+](CO)(CO)CO AKXUUJCMWZFYMV-UHFFFAOYSA-M 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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
- 241000206672 Gelidium Species 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- -1 phosphorus compound Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- 241000251468 Actinopterygii Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- GCAKFSUPQDLXIL-UHFFFAOYSA-N potassium rhodium Chemical compound [K].[Rh] GCAKFSUPQDLXIL-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000246 remedial effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/10—Aqueous solvent
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3562A GB959356A (en) | 1962-01-01 | 1962-01-01 | Improvements in or relating to chemical reactions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1264781B true DE1264781B (de) | 1968-03-28 |
Family
ID=9697229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962G0036756 Pending DE1264781B (de) | 1962-01-01 | 1962-12-31 | Verfahren zur Polymerisation von Vinylmonomeren |
Country Status (3)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5576508A (en) | 1978-12-01 | 1980-06-09 | Sumitomo Electric Industries | Method of fabricating crosslinked polyethylene cable |
| DE19842055A1 (de) * | 1998-09-15 | 2000-03-16 | Agfa Gevaert Ag | Herstellung kugelförmiger Polymerisate |
| US6294623B1 (en) | 1998-09-15 | 2001-09-25 | Agfa-Gevaert | Production of spherical polymers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833741A (en) * | 1956-03-29 | 1958-05-06 | H D Justi & Son Inc | Method of polymerizing acrylate esters in the presence of an organo-metallic inhibitor |
-
0
- NL NL287200D patent/NL287200A/xx unknown
- NL NL128627D patent/NL128627C/xx active
-
1962
- 1962-01-01 GB GB3562A patent/GB959356A/en not_active Expired
- 1962-12-31 DE DE1962G0036756 patent/DE1264781B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833741A (en) * | 1956-03-29 | 1958-05-06 | H D Justi & Son Inc | Method of polymerizing acrylate esters in the presence of an organo-metallic inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| NL287200A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| GB959356A (en) | 1964-06-03 |
| NL128627C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2703876C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE894321C (de) | Verfahren zum Polymerisieren von Acrylsaeureamiden, insbesondere N-di-substituiertenAcrylsaeureamiden | |
| EP1834941A2 (de) | Polymerisationsinhibitor zur Stabilisierung von olefinisch ungesättigten Monomeren | |
| DE2500428A1 (de) | Verfahren zum abtrennen von metallionen | |
| DE2052569C3 (de) | Ungesättigte phosphorhaltige Carbonsäurederivate | |
| DE1264781B (de) | Verfahren zur Polymerisation von Vinylmonomeren | |
| DE1217950B (de) | Verfahren zur Herstellung neuer Perhydrate von Aminoalkylphosphonsaeuren | |
| DE1165856B (de) | Verfahren zur Polymerisation von radikalisch polymerisierbaren ungesaettigten Verbindungen | |
| DE2125587A1 (de) | Verfahren zur Herstellung von Hypophosphiten | |
| DE69605923T2 (de) | Behandlungen zur inhibierung der polymerisation von vinylaromatischen monomeren | |
| EP0017897B1 (de) | Thiocarbamylhydroxylamin-Verbindungen und deren Verwendung als Polymerisationsinitiatoren | |
| DE1229531B (de) | Organische Radikaldonatoren-Reaktionen | |
| DE1060849B (de) | Stabilisierung von Perborat | |
| DE1619182A1 (de) | Weichmacher fuer Textilstoffe | |
| DD236521A1 (de) | Verfahren zur herstellung von neuen 3,3,4-trimethyl-4-sulfomethyl-pyrrolidiniumbetainen | |
| DE2919096A1 (de) | Verfahren zum reinigen von acrylsaeureesterhomo- oder -mischpolymerisaten durch senken des gehalts an freiem acrylsaeureestermonomeren | |
| DE1235896B (de) | Verfahren zur Herstellung primaerer oder sekundaerer Aminoalkylestersalze der Acryl-, Methacryl-, Croton-, Itacon- oder Fumarsaeure | |
| DE1239679B (de) | Stabilisierung von Acrylsaeureamiden oder alpha-Alkylacrylsaeureamiden gegen Polymerisation | |
| DE1034864B (de) | Verfahren zur Herstellung von Polymeren, die quaternaere Ammoniumgruppen enthalten | |
| DE1201778B (de) | Verfahren zur Bekaempfung von schleim-bildenden Mikroorganismen in Industriewaessern | |
| DE2034922C3 (de) | hexyl)-peroxydicarbonat und mindestens 70% cis-Isomeres enthaltende Di-(3.3.5trimethyl-cyclohexyO-peroxydiarbonat-Isomerengemische | |
| DE2060903B2 (de) | N-oxide der dibenzo eckige klammer auf b,f eckige klammer zu thiepinreihe, verfahren zur herstellung derselben und pharmazeutische mittel | |
| DE2113246A1 (de) | Inhibition der Polymerisation von Vinylmonomeren | |
| DE1015225B (de) | Verfahren zur Herstellung von wasserloeslichen oberflaechenaktiven Mischpolymerisaten | |
| DD231363A5 (de) | Verfahren zur polymerisation von vinychlorid |