DE1595180B2 - Verfahren zur herstellung von copolymeren aus vinylaromatisch schen verbindungen und schwefligsaeureanhydrid - Google Patents
Verfahren zur herstellung von copolymeren aus vinylaromatisch schen verbindungen und schwefligsaeureanhydridInfo
- Publication number
- DE1595180B2 DE1595180B2 DE19651595180 DE1595180A DE1595180B2 DE 1595180 B2 DE1595180 B2 DE 1595180B2 DE 19651595180 DE19651595180 DE 19651595180 DE 1595180 A DE1595180 A DE 1595180A DE 1595180 B2 DE1595180 B2 DE 1595180B2
- Authority
- DE
- Germany
- Prior art keywords
- hours
- copolymers
- anhydride
- vinyl
- aromatic compounds
- 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- Withdrawn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
- 229920001577 copolymer Polymers 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 title 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 16
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 235000010269 sulphur dioxide Nutrition 0.000 claims description 8
- -1 vinyl aromatic compounds Chemical class 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 6
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001491 aromatic compounds Chemical class 0.000 claims description 5
- 150000003568 thioethers Chemical class 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000004580 weight loss Effects 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 1
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/205—Copolymers of sulfur dioxide with unsaturated organic compounds
- C08G75/22—Copolymers of sulfur dioxide with unsaturated aliphatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR995232A FR1433352A (fr) | 1964-11-17 | 1964-11-17 | Procédé de préparation de copolymères à base d'anhydride sulfureux et produits en résultant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1595180A1 DE1595180A1 (de) | 1970-04-09 |
| DE1595180B2 true DE1595180B2 (de) | 1971-03-04 |
Family
ID=8842684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651595180 Withdrawn DE1595180B2 (de) | 1964-11-17 | 1965-11-16 | Verfahren zur herstellung von copolymeren aus vinylaromatisch schen verbindungen und schwefligsaeureanhydrid |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3448090A (enExample) |
| BE (1) | BE672032A (enExample) |
| DE (1) | DE1595180B2 (enExample) |
| FR (1) | FR1433352A (enExample) |
| GB (1) | GB1127245A (enExample) |
| NL (1) | NL143243B (enExample) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2481596A (en) * | 1946-08-13 | 1949-09-13 | Celanese Corp | Stabilization of polysulfone resins |
| US2637664A (en) * | 1949-06-23 | 1953-05-05 | Phillips Petroleum Co | Coating articles with an olefinsulfur dioxide resin |
| US2647879A (en) * | 1950-04-18 | 1953-08-04 | Monsanto Chemicals | Improving the flex resistance of butadiene-1, 3 type polymers |
| US2677664A (en) * | 1951-02-19 | 1954-05-04 | Telkes Maria | Composition of matter for the storage of heat |
| US2765295A (en) * | 1952-02-18 | 1956-10-02 | Phillips Petroleum Co | Butene-1-acrylonitrile-so terpolymers |
| US2705227A (en) * | 1954-03-15 | 1955-03-29 | Du Pont | Heat stabilization of polyamides |
-
0
- BE BE672032D patent/BE672032A/xx unknown
-
1964
- 1964-11-17 FR FR995232A patent/FR1433352A/fr not_active Expired
-
1965
- 1965-11-11 GB GB47907/65A patent/GB1127245A/en not_active Expired
- 1965-11-12 US US513144A patent/US3448090A/en not_active Expired - Lifetime
- 1965-11-16 DE DE19651595180 patent/DE1595180B2/de not_active Withdrawn
- 1965-11-16 NL NL656514868A patent/NL143243B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1127245A (en) | 1968-09-18 |
| DE1595180A1 (de) | 1970-04-09 |
| US3448090A (en) | 1969-06-03 |
| FR1433352A (fr) | 1966-04-01 |
| NL143243B (nl) | 1974-09-16 |
| BE672032A (enExample) | |
| NL6514868A (enExample) | 1966-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |