DE1233143B - Verfahren zur Herstellung von sulfonierten Mischpolymerisaten - Google Patents
Verfahren zur Herstellung von sulfonierten MischpolymerisatenInfo
- Publication number
- DE1233143B DE1233143B DE1962N0021275 DEN0021275A DE1233143B DE 1233143 B DE1233143 B DE 1233143B DE 1962N0021275 DE1962N0021275 DE 1962N0021275 DE N0021275 A DEN0021275 A DE N0021275A DE 1233143 B DE1233143 B DE 1233143B
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- acrylonitrile
- meq
- polymer
- sulfonated
- 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
- 229920001577 copolymer Polymers 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 31
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 23
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 18
- 238000006277 sulfonation reaction Methods 0.000 claims description 12
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 239000002253 acid Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000126 substance Substances 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 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- WSYAMLNOVPXLTR-UHFFFAOYSA-N 7,8-dioxabicyclo[4.2.0]octa-1,3,5-triene Chemical compound C1=CC=C2OOC2=C1 WSYAMLNOVPXLTR-UHFFFAOYSA-N 0.000 description 1
- 241000373567 Asio capensis Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000007696 Kjeldahl method Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- -1 benzene peroxide Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- PBGVMIDTGGTBFS-UHFFFAOYSA-N but-3-enylbenzene Chemical compound C=CCCC1=CC=CC=C1 PBGVMIDTGGTBFS-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 229920013730 reactive polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
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
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/16—Organic material
- B01J39/18—Macromolecular compounds
- B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
-
- 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
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP725461 | 1961-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1233143B true DE1233143B (de) | 1967-01-26 |
Family
ID=11660876
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1962N0021275 Pending DE1233143B (de) | 1961-03-01 | 1962-02-28 | Verfahren zur Herstellung von sulfonierten Mischpolymerisaten |
| DEN24838A Pending DE1227431B (de) | 1961-03-01 | 1962-02-28 | Kationenaustauscher |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN24838A Pending DE1227431B (de) | 1961-03-01 | 1962-02-28 | Kationenaustauscher |
Country Status (4)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228896B1 (en) | 1995-12-21 | 2001-05-08 | Iab Ionennaustauscher Gmbh Bitterfeld | Process for the preparation of very acidic cation exchangers |
| US6750259B2 (en) | 2002-07-08 | 2004-06-15 | Bayer Aktiengesellschaft | Process for preparing gel-type cation exchangers |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS182467B1 (en) * | 1975-06-05 | 1978-04-28 | Jiri Hradil | Method of preparing cationic ion exchanger |
| DE19644227A1 (de) * | 1996-10-24 | 1998-04-30 | Bayer Ag | Verfahren zur Herstellung ausblutarmer Kationenaustauscher |
| DE10050680A1 (de) * | 2000-10-13 | 2002-04-18 | Bayer Ag | Verfahren zur Herstellung stabiler gelförmiger Kationenaustauscher |
| CN103987458A (zh) * | 2011-12-28 | 2014-08-13 | 陶氏环球技术有限公司 | 强酸催化剂组合物 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE915267C (de) * | 1942-08-11 | 1954-07-19 | Gen Electric | Verfahren zur Herstellung von synthetischen, polymeren, wasserunloeslichen Sulfonierungsprodukten |
| US2759910A (en) * | 1951-11-06 | 1956-08-21 | Distillers Co Yeast Ltd | Polymerised compositions |
| GB775539A (en) * | 1954-11-24 | 1957-05-22 | Dow Chemical Co | Preparation of water-soluble sulphonation products of polymeric ar-vinyltoluenes |
| US2809959A (en) * | 1957-10-15 | Preparation of high-viscosity sulfona- | ||
| US2813087A (en) * | 1955-04-14 | 1957-11-12 | Dow Chemical Co | Preparation of water-soluble sulfonation products from polymers of arvinyltoluene and acrylonitrile |
| US2829128A (en) * | 1953-12-07 | 1958-04-01 | Monsanto Chemicals | Clear terpolymers |
| DE1031514B (de) * | 1954-11-24 | 1958-06-04 | Dow Chemical Co | Verfahren zur Herstellung von Harzsulfonaten |
| DE1070382B (de) * | 1959-12-03 | VEB Farbenfabrik Wolfen, Wolfen (Kr. Bitterfeld) | Verfahren zur Herstellung von Austauscherpolymerisaten |
-
0
- NL NL125475D patent/NL125475C/xx active
- NL NL275074D patent/NL275074A/xx unknown
-
1962
- 1962-02-28 DE DE1962N0021275 patent/DE1233143B/de active Pending
- 1962-02-28 DE DEN24838A patent/DE1227431B/de active Pending
- 1962-03-01 CH CH251862A patent/CH410424A/fr unknown
- 1962-03-13 GB GB968062A patent/GB997290A/en not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809959A (en) * | 1957-10-15 | Preparation of high-viscosity sulfona- | ||
| DE1070382B (de) * | 1959-12-03 | VEB Farbenfabrik Wolfen, Wolfen (Kr. Bitterfeld) | Verfahren zur Herstellung von Austauscherpolymerisaten | |
| DE915267C (de) * | 1942-08-11 | 1954-07-19 | Gen Electric | Verfahren zur Herstellung von synthetischen, polymeren, wasserunloeslichen Sulfonierungsprodukten |
| US2759910A (en) * | 1951-11-06 | 1956-08-21 | Distillers Co Yeast Ltd | Polymerised compositions |
| US2829128A (en) * | 1953-12-07 | 1958-04-01 | Monsanto Chemicals | Clear terpolymers |
| GB775539A (en) * | 1954-11-24 | 1957-05-22 | Dow Chemical Co | Preparation of water-soluble sulphonation products of polymeric ar-vinyltoluenes |
| DE1031514B (de) * | 1954-11-24 | 1958-06-04 | Dow Chemical Co | Verfahren zur Herstellung von Harzsulfonaten |
| US2813087A (en) * | 1955-04-14 | 1957-11-12 | Dow Chemical Co | Preparation of water-soluble sulfonation products from polymers of arvinyltoluene and acrylonitrile |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228896B1 (en) | 1995-12-21 | 2001-05-08 | Iab Ionennaustauscher Gmbh Bitterfeld | Process for the preparation of very acidic cation exchangers |
| US6750259B2 (en) | 2002-07-08 | 2004-06-15 | Bayer Aktiengesellschaft | Process for preparing gel-type cation exchangers |
Also Published As
| Publication number | Publication date |
|---|---|
| CH410424A (fr) | 1966-03-31 |
| GB997290A (en) | 1965-07-07 |
| NL275074A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| DE1227431B (de) | 1966-10-27 |
| NL125475C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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