DE2322119C3 - Verfahren zur Herstellung von kugelförmigen, kleinen Polymerteilchen - Google Patents
Verfahren zur Herstellung von kugelförmigen, kleinen PolymerteilchenInfo
- Publication number
- DE2322119C3 DE2322119C3 DE2322119A DE2322119A DE2322119C3 DE 2322119 C3 DE2322119 C3 DE 2322119C3 DE 2322119 A DE2322119 A DE 2322119A DE 2322119 A DE2322119 A DE 2322119A DE 2322119 C3 DE2322119 C3 DE 2322119C3
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- water
- particles
- solvent
- 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 56
- 239000002245 particle Substances 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 22
- 239000000839 emulsion Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 9
- BDJRBEYXGGNYIS-UHFFFAOYSA-N azelaic acid group Chemical group C(CCCCCCCC(=O)O)(=O)O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 229920001634 Copolyester Polymers 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical group OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- 239000007764 o/w emulsion Substances 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000001856 Ethyl cellulose Substances 0.000 claims description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims description 2
- 229920001249 ethyl cellulose Polymers 0.000 claims description 2
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000005060 rubber Substances 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000576 coating method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012798 spherical particle Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- -1 sulfate ester Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000020 Nitrocellulose Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 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 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- PPAFDTIQCIVDKX-UHFFFAOYSA-N dodecane undecane Chemical compound CCCCCCCCCCC.CCCCCCCCCCCC PPAFDTIQCIVDKX-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/16—Powdering or granulating by coagulating dispersions
Landscapes
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25429472A | 1972-05-17 | 1972-05-17 | |
| US00334344A US3847886A (en) | 1972-05-17 | 1973-02-21 | Method of preparing small particles of a solid polymer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2322119A1 DE2322119A1 (de) | 1973-12-06 |
| DE2322119B2 DE2322119B2 (de) | 1979-01-18 |
| DE2322119C3 true DE2322119C3 (de) | 1979-09-13 |
Family
ID=26943958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2322119A Expired DE2322119C3 (de) | 1972-05-17 | 1973-05-02 | Verfahren zur Herstellung von kugelförmigen, kleinen Polymerteilchen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3847886A (enExample) |
| JP (1) | JPS5632332B2 (enExample) |
| AU (1) | AU466301B2 (enExample) |
| CA (1) | CA1009815A (enExample) |
| DE (1) | DE2322119C3 (enExample) |
| FR (1) | FR2184783B1 (enExample) |
| GB (1) | GB1409638A (enExample) |
| IT (1) | IT987639B (enExample) |
| NL (1) | NL7306710A (enExample) |
| SE (1) | SE379203B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1012692A (en) * | 1973-01-19 | 1977-06-21 | Du Pont Of Canada Limited | Removal of volatile impurities from polymers |
| JPS5947685B2 (ja) * | 1974-03-05 | 1984-11-21 | 鐘淵化学工業株式会社 | 塩化ビニル共重合体の製造方法 |
| CS179075B1 (en) * | 1974-11-26 | 1977-10-31 | Stoy Vladimir | Mode of manufacture of spherical particles from polymer |
| US4205162A (en) * | 1978-11-03 | 1980-05-27 | Stauffer Chemical Company | Polymer recovery process |
| US4304843A (en) * | 1978-11-22 | 1981-12-08 | E. I. Du Pont De Nemours And Company | Dry toner with improved toning uniformity |
| US4546172A (en) * | 1983-01-20 | 1985-10-08 | Mitsubishi Chemical Industries Ltd. | Process for producing polycarbonate resin particles |
| JPS6094409A (ja) * | 1983-10-28 | 1985-05-27 | Nippon Zeon Co Ltd | 塩化ビニル樹脂の回収方法 |
| JPS621728A (ja) * | 1985-06-27 | 1987-01-07 | Chuichi Hirayama | ポリアミノ酸の球状粒子とその製造方法 |
| US4833060A (en) * | 1988-03-21 | 1989-05-23 | Eastman Kodak Company | Polymeric powders having a predetermined and controlled size and size distribution |
| JP3123153B2 (ja) * | 1991-11-11 | 2001-01-09 | ミノルタ株式会社 | 静電荷像現像用トナーおよびその製造方法 |
| JP2004109943A (ja) * | 2002-09-20 | 2004-04-08 | Ricoh Co Ltd | 画像形成装置 |
| US7704340B1 (en) * | 2002-10-02 | 2010-04-27 | The United States Of America As Represented By The Secretary Of The Navy | Pelletized nitrocellulose (PNC) manufacture and long term storage |
| JP5882021B2 (ja) * | 2011-10-19 | 2016-03-09 | 東洋ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ、並びに微粒子ゴム粉末の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2202481A (en) * | 1937-11-20 | 1940-05-28 | Carbide & Carbon Chem Corp | Recovery of plastic materials |
-
1973
- 1973-02-21 US US00334344A patent/US3847886A/en not_active Expired - Lifetime
- 1973-04-09 CA CA168,260A patent/CA1009815A/en not_active Expired
- 1973-04-26 AU AU54852/73A patent/AU466301B2/en not_active Expired
- 1973-05-02 DE DE2322119A patent/DE2322119C3/de not_active Expired
- 1973-05-14 FR FR7317293A patent/FR2184783B1/fr not_active Expired
- 1973-05-14 SE SE7306774A patent/SE379203B/xx unknown
- 1973-05-15 NL NL7306710A patent/NL7306710A/xx not_active Application Discontinuation
- 1973-05-16 GB GB2329073A patent/GB1409638A/en not_active Expired
- 1973-05-16 IT IT24178/73A patent/IT987639B/it active
- 1973-05-17 JP JP5421173A patent/JPS5632332B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5632332B2 (enExample) | 1981-07-27 |
| AU466301B2 (en) | 1975-10-23 |
| DE2322119B2 (de) | 1979-01-18 |
| AU5485273A (en) | 1974-10-31 |
| JPS4941448A (enExample) | 1974-04-18 |
| IT987639B (it) | 1975-03-20 |
| NL7306710A (enExample) | 1973-11-20 |
| DE2322119A1 (de) | 1973-12-06 |
| GB1409638A (en) | 1975-10-08 |
| US3847886A (en) | 1974-11-12 |
| FR2184783B1 (enExample) | 1977-12-30 |
| FR2184783A1 (enExample) | 1973-12-28 |
| CA1009815A (en) | 1977-05-10 |
| SE379203B (enExample) | 1975-09-29 |
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| DE2721501C2 (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |