DE2032953C3 - Verfahren zur Herstellung perlförmiger Polymerisate der Acrylsäure und Verwendung dieser Polyacrylsäuren - Google Patents
Verfahren zur Herstellung perlförmiger Polymerisate der Acrylsäure und Verwendung dieser PolyacrylsäurenInfo
- Publication number
- DE2032953C3 DE2032953C3 DE2032953A DE2032953A DE2032953C3 DE 2032953 C3 DE2032953 C3 DE 2032953C3 DE 2032953 A DE2032953 A DE 2032953A DE 2032953 A DE2032953 A DE 2032953A DE 2032953 C3 DE2032953 C3 DE 2032953C3
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- acrylic acid
- bead
- weight
- solution
- 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
- 229920000642 polymer Polymers 0.000 title claims description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 42
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims description 41
- 229920002125 Sokalan® Polymers 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 29
- 230000008569 process Effects 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 53
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 38
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 30
- 239000004971 Cross linker Substances 0.000 claims description 25
- 239000003112 inhibitor Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 13
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 7
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 7
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 239000011953 free-radical catalyst Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 111
- 239000011324 bead Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 42
- 239000011049 pearl Substances 0.000 description 37
- 239000004342 Benzoyl peroxide Substances 0.000 description 27
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 27
- 235000019400 benzoyl peroxide Nutrition 0.000 description 27
- 239000012429 reaction media Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 16
- 239000004584 polyacrylic acid Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 238000004062 sedimentation Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 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 description 9
- 229910021645 metal ion Inorganic materials 0.000 description 8
- 239000002685 polymerization catalyst Substances 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000013459 approach Methods 0.000 description 7
- 239000008139 complexing agent Substances 0.000 description 7
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000536 complexating effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000001934 delay Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- FHCIUVQKHDFBRJ-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene heptane Chemical compound CCCCCCC.C1CCCC2CCCCC21 FHCIUVQKHDFBRJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MVWDJLOUEUAWIE-UHFFFAOYSA-N O=C=O.O=C=O Chemical compound O=C=O.O=C=O MVWDJLOUEUAWIE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012688 inverse emulsion polymerization Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
- C11D3/3761—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in solid compositions
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/04—Acids, Metal salts or ammonium salts thereof
- C08F20/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Hydrology & Water Resources (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2032953A DE2032953C3 (de) | 1970-07-03 | 1970-07-03 | Verfahren zur Herstellung perlförmiger Polymerisate der Acrylsäure und Verwendung dieser Polyacrylsäuren |
| CH494071A CH558389A (de) | 1970-07-03 | 1971-04-05 | Verfahren zur herstellung perlfoermiger polymerisate der acrylsaeure und deren verwendung. |
| NL7106453A NL7106453A (enExample) | 1970-07-03 | 1971-05-11 | |
| FR7121465A FR2097869A5 (enExample) | 1970-07-03 | 1971-06-14 | |
| BE769391A BE769391A (fr) | 1970-07-03 | 1971-07-01 | Procede pour la preparation de polymeres en perles de l'acide acryliqueet utilisation de ces acides polyacryliques |
| SE7108615A SE380276B (sv) | 1970-07-03 | 1971-07-02 | Forfarande for framstellning av perlformiga polymerisat av akrylsyra |
| GB3105071A GB1341073A (en) | 1970-07-03 | 1971-07-02 | Bear polymers of acrylic acid |
| JP46049178A JPS5136791B1 (enExample) | 1970-07-03 | 1971-07-03 | |
| US05/497,645 US3948867A (en) | 1970-07-03 | 1974-08-15 | Process for polymerizing acrylic acid with inhibitor and retarder present and the use of resultant polyacrylic acids |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2032953A DE2032953C3 (de) | 1970-07-03 | 1970-07-03 | Verfahren zur Herstellung perlförmiger Polymerisate der Acrylsäure und Verwendung dieser Polyacrylsäuren |
| US16016171A | 1971-07-06 | 1971-07-06 | |
| US05/497,645 US3948867A (en) | 1970-07-03 | 1974-08-15 | Process for polymerizing acrylic acid with inhibitor and retarder present and the use of resultant polyacrylic acids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2032953A1 DE2032953A1 (de) | 1972-01-05 |
| DE2032953B2 DE2032953B2 (de) | 1977-11-10 |
| DE2032953C3 true DE2032953C3 (de) | 1978-08-17 |
Family
ID=27182704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2032953A Expired DE2032953C3 (de) | 1970-07-03 | 1970-07-03 | Verfahren zur Herstellung perlförmiger Polymerisate der Acrylsäure und Verwendung dieser Polyacrylsäuren |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3948867A (enExample) |
| BE (1) | BE769391A (enExample) |
| CH (1) | CH558389A (enExample) |
| DE (1) | DE2032953C3 (enExample) |
| FR (1) | FR2097869A5 (enExample) |
| GB (1) | GB1341073A (enExample) |
| NL (1) | NL7106453A (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2800357A1 (de) * | 1978-01-05 | 1979-07-19 | Bayer Ag | Verfahren zur herstellung von oligomeren acrylsaeuren |
| US4302350A (en) | 1979-04-09 | 1981-11-24 | The Procter & Gamble Company | Method and composition to inhibit staining of porcelain surfaces by manganese |
| EP0018344B1 (en) * | 1979-04-09 | 1983-06-22 | THE PROCTER & GAMBLE COMPANY | Method and composition to inhibit staining of porcelain surfaces by manganese, and toilet tank dispenser using this composition |
| DE3013812A1 (de) * | 1980-04-10 | 1981-10-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von waessrigen polymer-dispersionen mit einem polymerisatgehalt bis 75 gew. prozent |
| EP0065078B1 (en) * | 1981-04-27 | 1985-06-19 | American Cyanamid Company | A process for improving the polymerizability of acrylonitrile, acrylamide, acrylic acid and mixtures thereof |
| US4655957A (en) * | 1984-06-25 | 1987-04-07 | Bausch & Lomb Incorporated | Contact lens cleaning composition with polymeric beads |
| US4692502A (en) * | 1986-06-09 | 1987-09-08 | The Standard Oil Company | Polymerization process for carboxyl containing polymers utilizing oil soluble ionic surface active agents |
| DE69629291T2 (de) * | 1995-05-26 | 2004-04-22 | Igen International, Inc.(n.d.Ges.d.Staates Delaware) | Molekular geprägten perl polymere und stabilisierte suspensionspolymerisation von diesen in perfluorkohlstoff flussigkeiten |
| GB9700528D0 (en) * | 1997-01-13 | 1997-03-05 | Allied Colloids Ltd | Polymerisation processes and products |
| US6444744B1 (en) * | 1998-03-11 | 2002-09-03 | Nippon Shokubai Co., Ltd. | Hydrophilic resin, absorbent article, and acrylic acid for polymerization |
| EP1104681A1 (en) * | 1999-12-03 | 2001-06-06 | Biomat B.V. | Wire, tube or catheter with hydrophilic coating |
| JP4009700B2 (ja) * | 2003-10-20 | 2007-11-21 | 株式会社テクノネットワーク四国 | ラジカル重合体の製造方法 |
| KR101668900B1 (ko) * | 2009-08-04 | 2016-10-24 | 스미또모 세이까 가부시키가이샤 | 카르복실기 함유 수용성 중합체의 제조 방법 |
| GB201114332D0 (en) * | 2011-08-19 | 2011-10-05 | Nufarm Uk Ltd | Novel inhibitor compositions and methods of use |
| JP6220342B2 (ja) * | 2012-10-26 | 2017-10-25 | 和光純薬工業株式会社 | リチウム電池用結着剤、電極作製用組成物および電極 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904541A (en) * | 1953-12-23 | 1959-09-15 | Monsanto Chemicals | Continuous polymerization processes and resulting products |
| GB971055A (en) * | 1963-01-18 | 1964-09-30 | Standard Telephones Cables Ltd | Acrylic acid polymers |
| US3493471A (en) * | 1967-12-01 | 1970-02-03 | Dow Chemical Co | Acrylic acid purification |
-
1970
- 1970-07-03 DE DE2032953A patent/DE2032953C3/de not_active Expired
-
1971
- 1971-04-05 CH CH494071A patent/CH558389A/xx not_active IP Right Cessation
- 1971-05-11 NL NL7106453A patent/NL7106453A/xx not_active Application Discontinuation
- 1971-06-14 FR FR7121465A patent/FR2097869A5/fr not_active Expired
- 1971-07-01 BE BE769391A patent/BE769391A/xx unknown
- 1971-07-02 GB GB3105071A patent/GB1341073A/en not_active Expired
-
1974
- 1974-08-15 US US05/497,645 patent/US3948867A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7106453A (enExample) | 1972-01-05 |
| DE2032953B2 (de) | 1977-11-10 |
| GB1341073A (en) | 1973-12-19 |
| DE2032953A1 (de) | 1972-01-05 |
| BE769391A (fr) | 1971-11-16 |
| CH558389A (de) | 1975-01-31 |
| US3948867A (en) | 1976-04-06 |
| FR2097869A5 (enExample) | 1972-03-03 |
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