GB1020907A - Method of producing ion exchange resins having a sponge structure - Google Patents
Method of producing ion exchange resins having a sponge structureInfo
- Publication number
- GB1020907A GB1020907A GB51764A GB51764A GB1020907A GB 1020907 A GB1020907 A GB 1020907A GB 51764 A GB51764 A GB 51764A GB 51764 A GB51764 A GB 51764A GB 1020907 A GB1020907 A GB 1020907A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- divinyl
- ether
- ion exchange
- groups
- 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.)
- Expired
Links
- 239000003456 ion exchange resin Substances 0.000 title abstract 2
- 229920003303 ion-exchange polymer Polymers 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 6
- -1 vinyl napthalene Chemical compound 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 230000010849 Ion Exchange Activity Effects 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 abstract 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003700 epoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 abstract 1
- YKKDJUGGSDWUKX-UHFFFAOYSA-N 1,2-bis(ethenyl)-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1C=C YKKDJUGGSDWUKX-UHFFFAOYSA-N 0.000 abstract 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 abstract 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- BAFMBHJRYJBYQD-UHFFFAOYSA-N 2-ethyl-3-phenyloxirane Chemical compound CCC1OC1C1=CC=CC=C1 BAFMBHJRYJBYQD-UHFFFAOYSA-N 0.000 abstract 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 abstract 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 abstract 1
- LBSKXDSMJGRBOZ-UHFFFAOYSA-N 6-prop-2-enyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(CC=C)C1O2 LBSKXDSMJGRBOZ-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- FVGJPCFYGPKBKJ-UHFFFAOYSA-N Dodecyl propionate Chemical compound CCCCCCCCCCCCOC(=O)CC FVGJPCFYGPKBKJ-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 abstract 1
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005576 amination reaction Methods 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- IHTWATXYZJSPOM-UHFFFAOYSA-N bis(ethenyl) oxalate Chemical compound C=COC(=O)C(=O)OC=C IHTWATXYZJSPOM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 abstract 1
- 229940091854 dodecyl propionate Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 abstract 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 abstract 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- AUBDSFLQOBEOPX-UHFFFAOYSA-N hexa-1,5-dien-3-yne Chemical group C=CC#CC=C AUBDSFLQOBEOPX-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 abstract 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 229920002102 polyvinyl toluene Polymers 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 abstract 1
- 229960000834 vinyl ether Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
- C08J9/286—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers
-
- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Ion exchange resins having a sponge structure are produced by a method wherein one or more monovinyl aromatic compounds and one or more polyvinyl compounds are copolymerized in the presence of substances which dissolve in the monomer mixture but in which the resulting aromatic vinyl polymers are practically neither soluble nor swellable, and in the presence of 0.1% to 20% by weight referred to the monomer mixture, of one or more polar compounds containing vinyl and/or epoxy groups, followed by the subsequent introduction of groups having ion exchange activity. As monovinyl aromatic substances there may be used styrene, vinyl toluene, vinyl ethyl benzene, vinyl anisole, acenaphthylene and vinyl napthalene. Examples of polyvinyl compounds are divinyl benzene, divinyl ethyl benzene, trivinylbenzene, divinyl acetylene, butadiene, ethylene glycol dimethacrylate, divinyl ketone, divinyl sulphone, oxalic acid divinyl ester, divinyl ether and methacrylic acid vinyl ester. Suitable non-solvents are benzine (b.p. 100-140 DEG C.), white spirit (bp. 160-190 DEG C.), titralin, decalin, cyclohexane, butanol, amyl alcohol, dodecanol, cyclohexanol, diphenyl ether, dihexyl ether, 2-ethylhexyl acetate, dodecylpropionate, nitromethane, linear polystyrene and linear polyvinyltoluene. Polar compounds containing vinyl groups may be acrylic acid and its derivatives, methacrylic acid and its derivatives, methyl vinyl ketone, vinyl halides, vinyl benzyl halides, methyl vinyl ether, vinyl pyridine, esters of vinyl alcohol such as vinyl acetate and vinyl propionate and maleic acid and its derivatives. Those containing epoxy groups may be styrene oxide, vinyl toluene oxide, ethyl styrene oxide, phenyl glycide ether, divinyl benzene dioxide and epichlorohydrin. The introduction of groups having ion exchange activity may be effected by halogen alkylation and amination, nitration and reduction, sulphonation, halogenation with a phosphorus halide followed by saponification and oxidation, halogen alkylation followed by reaction with trialkyl phosphites and saponification.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51764A GB1020907A (en) | 1964-01-06 | 1964-01-06 | Method of producing ion exchange resins having a sponge structure |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51764A GB1020907A (en) | 1964-01-06 | 1964-01-06 | Method of producing ion exchange resins having a sponge structure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1020907A true GB1020907A (en) | 1966-02-23 |
Family
ID=9705760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB51764A Expired GB1020907A (en) | 1964-01-06 | 1964-01-06 | Method of producing ion exchange resins having a sponge structure |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1020907A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5832603A (en) * | 1981-08-21 | 1983-02-25 | Mitsubishi Chem Ind Ltd | Preparation of cation exchange resin |
| WO2015157552A1 (en) * | 2014-04-09 | 2015-10-15 | Rohm And Haas Company | Catalyst resin |
| WO2015157551A1 (en) * | 2014-04-09 | 2015-10-15 | Rohm And Haas Company | Catalyst resin |
-
1964
- 1964-01-06 GB GB51764A patent/GB1020907A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5832603A (en) * | 1981-08-21 | 1983-02-25 | Mitsubishi Chem Ind Ltd | Preparation of cation exchange resin |
| WO2015157552A1 (en) * | 2014-04-09 | 2015-10-15 | Rohm And Haas Company | Catalyst resin |
| WO2015157551A1 (en) * | 2014-04-09 | 2015-10-15 | Rohm And Haas Company | Catalyst resin |
| US9809692B2 (en) | 2014-04-09 | 2017-11-07 | Rohm And Haas Company | Catalyst resin |
| US10023711B2 (en) | 2014-04-09 | 2018-07-17 | Rohm And Haas Company | Catalyst resin |
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