DE1645106B1 - Verfahren zur herstellung von copolymerisaten aus schweflig saeureanhydrid und ungesaettigten organischen verbindungen - Google Patents
Verfahren zur herstellung von copolymerisaten aus schweflig saeureanhydrid und ungesaettigten organischen verbindungenInfo
- Publication number
- DE1645106B1 DE1645106B1 DE19661645106 DE1645106A DE1645106B1 DE 1645106 B1 DE1645106 B1 DE 1645106B1 DE 19661645106 DE19661645106 DE 19661645106 DE 1645106 A DE1645106 A DE 1645106A DE 1645106 B1 DE1645106 B1 DE 1645106B1
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- amount
- product
- added
- hours
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 24
- 150000002894 organic compounds Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000008065 acid anhydrides Chemical class 0.000 title 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 42
- 229920001577 copolymer Polymers 0.000 claims description 37
- 235000010269 sulphur dioxide Nutrition 0.000 claims description 20
- 238000007334 copolymerization reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 5
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- -1 aliphatic mercaptans Chemical class 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 229960002380 dibutyl phthalate Drugs 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 26
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 229920002492 poly(sulfone) Polymers 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229920000896 Ethulose Polymers 0.000 description 5
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000012736 aqueous medium Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000011049 pearl Substances 0.000 description 5
- 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 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 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 3
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 3
- 238000000889 atomisation Methods 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- HLOUDBQOEJSUPI-UHFFFAOYSA-N 1-ethenyl-2,3-dimethylbenzene Chemical class CC1=CC=CC(C=C)=C1C HLOUDBQOEJSUPI-UHFFFAOYSA-N 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 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)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR75009241 | 1965-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1645106B1 true DE1645106B1 (de) | 1972-01-05 |
Family
ID=9696040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661645106 Withdrawn DE1645106B1 (de) | 1965-03-15 | 1966-02-14 | Verfahren zur herstellung von copolymerisaten aus schweflig saeureanhydrid und ungesaettigten organischen verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE677824A (enrdf_load_stackoverflow) |
| DE (1) | DE1645106B1 (enrdf_load_stackoverflow) |
| FR (1) | FR1453274A (enrdf_load_stackoverflow) |
| GB (1) | GB1139564A (enrdf_load_stackoverflow) |
| NL (1) | NL6601057A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000077077A1 (de) * | 1999-06-11 | 2000-12-21 | Basf Aktiengesellschaft | Verfahren zur herstellung von polysulfonen mit alipatischer hauptkette |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2643241A (en) * | 1951-01-02 | 1953-06-23 | Phillips Petroleum Co | Stabilization of polysulfone resins with organic sulfides |
-
1965
- 1965-03-15 FR FR9241A patent/FR1453274A/fr not_active Expired
-
1966
- 1966-01-27 NL NL6601057A patent/NL6601057A/xx unknown
- 1966-02-14 DE DE19661645106 patent/DE1645106B1/de not_active Withdrawn
- 1966-03-14 BE BE677824D patent/BE677824A/xx unknown
- 1966-03-14 GB GB1111566A patent/GB1139564A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2643241A (en) * | 1951-01-02 | 1953-06-23 | Phillips Petroleum Co | Stabilization of polysulfone resins with organic sulfides |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000077077A1 (de) * | 1999-06-11 | 2000-12-21 | Basf Aktiengesellschaft | Verfahren zur herstellung von polysulfonen mit alipatischer hauptkette |
Also Published As
| Publication number | Publication date |
|---|---|
| BE677824A (enrdf_load_stackoverflow) | 1966-09-14 |
| NL6601057A (enrdf_load_stackoverflow) | 1966-09-16 |
| FR1453274A (fr) | 1966-09-23 |
| GB1139564A (en) | 1969-01-08 |
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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 |