CA1163033A - Preparation of copolymer dispersions having a narrow particle size distribution, and exhibiting dilatant flow over a broad range of concentrations - Google Patents
Preparation of copolymer dispersions having a narrow particle size distribution, and exhibiting dilatant flow over a broad range of concentrationsInfo
- Publication number
- CA1163033A CA1163033A CA000381041A CA381041A CA1163033A CA 1163033 A CA1163033 A CA 1163033A CA 000381041 A CA000381041 A CA 000381041A CA 381041 A CA381041 A CA 381041A CA 1163033 A CA1163033 A CA 1163033A
- Authority
- CA
- Canada
- Prior art keywords
- percent
- weight
- copolymer
- monomers
- olefinically unsaturated
- 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
- 229920001577 copolymer Polymers 0.000 title claims abstract description 51
- 239000006185 dispersion Substances 0.000 title claims abstract description 34
- 239000002245 particle Substances 0.000 title claims abstract description 29
- 230000001747 exhibiting effect Effects 0.000 title claims abstract description 10
- 238000009826 distribution Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000000839 emulsion Substances 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000009477 glass transition Effects 0.000 claims abstract description 12
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 claims abstract description 8
- 230000002776 aggregation Effects 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 7
- 150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 7
- 238000005054 agglomeration Methods 0.000 claims abstract description 6
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 6
- 230000004927 fusion Effects 0.000 claims abstract description 5
- 239000002270 dispersing agent Substances 0.000 claims abstract description 4
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 2
- 239000012874 anionic emulsifier Substances 0.000 claims description 2
- 239000012875 nonionic emulsifier Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 238000010008 shearing Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 229920000126 latex Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 229940063559 methacrylic acid Drugs 0.000 description 4
- -1 vinyl halides Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940102838 methylmethacrylate Drugs 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical class OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 235000019394 potassium persulphate Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical class COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- DYYFCJRYZVHEKQ-UHFFFAOYSA-N 3-butoxycarbonylbut-3-enoic acid Chemical compound CCCCOC(=O)C(=C)CC(O)=O DYYFCJRYZVHEKQ-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 229940074369 monoethyl fumarate Drugs 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical class OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- 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
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3025562.0 | 1980-07-05 | ||
| DE19803025562 DE3025562A1 (de) | 1980-07-05 | 1980-07-05 | Verfahren zur herstellung von copolymerdispersionen enger teilchengroessenverteilung mit breitem konzentrationsbereich dilatanten fliessverhaltens |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163033A true CA1163033A (en) | 1984-02-28 |
Family
ID=6106513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000381041A Expired CA1163033A (en) | 1980-07-05 | 1981-07-03 | Preparation of copolymer dispersions having a narrow particle size distribution, and exhibiting dilatant flow over a broad range of concentrations |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4371636A (en, 2012) |
| EP (1) | EP0043464B1 (en, 2012) |
| JP (1) | JPS5744614A (en, 2012) |
| AT (1) | ATE7302T1 (en, 2012) |
| CA (1) | CA1163033A (en, 2012) |
| DE (2) | DE3025562A1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10687946B2 (en) | 2016-04-25 | 2020-06-23 | Betterguards Technology Gmbh | Device for stabilising joints |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6045665B2 (ja) * | 1980-04-21 | 1985-10-11 | 日立化成工業株式会社 | 実装回路板用防湿絶縁塗料組成物 |
| DE3123344A1 (de) * | 1981-06-12 | 1982-12-30 | Krauss-Maffei AG, 8000 München | Dreh-stossdaempfer |
| DE3211900A1 (de) * | 1982-03-31 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | Verfahren zum verfestigen der oberflaechen von koernigen adsorbentien |
| DE3405907A1 (de) * | 1984-02-18 | 1985-08-22 | Daimler-Benz Ag, 7000 Stuttgart | Lager fuer die schwingungsisolierende abstuetzung eines schwingungsfaehigen aggregates an einem unterbau |
| DE3433085A1 (de) * | 1984-09-08 | 1986-03-20 | Basf Ag, 6700 Ludwigshafen | Stark dilatante polymerdispersionen mit verminderter temperaturabhaengigkeit der kritischen schergeschwindigkeit |
| DE3639091A1 (de) * | 1986-11-14 | 1988-05-26 | Daimler Benz Ag | Scherelement |
| DE3738716A1 (de) * | 1986-11-14 | 1988-09-15 | Daimler Benz Ag | Scherelement |
| US4840991A (en) * | 1986-11-28 | 1989-06-20 | Desoto, Inc. | Aqueous dispersions of partially cross-linked emulsion copolymers |
| US4853421A (en) * | 1988-02-03 | 1989-08-01 | Union Camp Corporation | Polyamide resin dispersions and method for the manufacture thereof |
| US4886844A (en) * | 1988-02-03 | 1989-12-12 | Union Camp Corporation | Polyamide resin dispersions and method for the manufacture thereof |
| DE3917757A1 (de) * | 1988-06-04 | 1989-12-07 | Daimler Benz Ag | Vorrichtung zur uebertragung eines drehmomentes mittels schubspannung eines sich gegenueberliegende zylindrische scherflaechen benetzenden fluessigen bzw. fliessfaehigen arbeitsmittels in einem drehmomentuebertragungsstrang |
| DE3917506A1 (de) * | 1988-06-04 | 1989-12-07 | Basf Ag | Fluessigkeitsreibungskupplung zur selbsttaetig zu- und abschaltbaren drehmomentuebertragung |
| EP0372047B1 (de) * | 1988-06-04 | 1992-02-26 | BASF Aktiengesellschaft | Flüssigkeitsreibungskupplung zur selbsttätig zu- und abschaltbaren drehmomentübertragung |
| DE3917456A1 (de) * | 1989-05-30 | 1990-12-06 | Basf Ag | Stark dilatante copolymerdispersion mit hoher dauerlastbestaendigkeit |
| DE4035653A1 (de) * | 1990-11-09 | 1992-05-14 | Daimler Benz Ag | Antriebs-schlupf-regeleinrichtung |
| DE4236040A1 (de) | 1992-10-24 | 1994-04-28 | Elastogran Gmbh | Stoßdämpfer |
| US5599290A (en) * | 1992-11-20 | 1997-02-04 | Beth Israel Hospital | Bone fracture prevention garment and method |
| US5712011A (en) * | 1995-07-27 | 1998-01-27 | Beth Israel Deaconess Medical Center, Inc. | Tug-resistant link |
| DE19602609A1 (de) * | 1996-01-25 | 1997-07-31 | Bayerische Motoren Werke Ag | Hydraulisch gedämpftes Zweimassenschwungrad |
| US6093468A (en) * | 1997-03-14 | 2000-07-25 | The Procter & Gamble Company | Flexible lightweight protective pad with energy absorbing inserts |
| GB2331717B (en) * | 1997-11-26 | 1999-12-22 | Ranier Ltd | Reticulated coatings |
| US20010005699A1 (en) | 1999-02-03 | 2001-06-28 | Morgan William E. | Multi-layer golf ball |
| US7547746B2 (en) * | 2005-06-09 | 2009-06-16 | Acushnet Company | Golf ball containing centipede polymers |
| US20050227786A1 (en) * | 2002-07-15 | 2005-10-13 | Sullivan Michael J | Golf ball with velocity reduced layer |
| US20040094026A1 (en) * | 2002-11-19 | 2004-05-20 | Integrity Testing Laboratory Inc. | Method of making a protective material and articles made therefrom |
| DE102004033813B4 (de) * | 2004-07-12 | 2010-04-08 | Endress + Hauser Gmbh + Co. Kg | Druckmessgerät |
| DE102009046437B4 (de) * | 2009-11-05 | 2018-04-19 | Man Diesel & Turbo Se | Verfahren zum Bearbeiten einer Einspritzdüse |
| EP2507300A1 (de) | 2009-12-04 | 2012-10-10 | Basf Se | Verfahren zur herstellung einer polymerisatdispersion |
| US20110133110A1 (en) * | 2009-12-04 | 2011-06-09 | Basf Se | Process for producing a polymer dispersion |
| US8679047B2 (en) | 2010-05-21 | 2014-03-25 | Presidium Athletics LLC | Impact resistant, torsion-reducing protective athletic gear using shear thickening fluid |
| DE202011000414U1 (de) | 2011-02-22 | 2012-05-23 | Brose Fahrzeugteile Gmbh & Co. Kommanditgesellschaft, Hallstadt | Dämpfungsvorrichtung zum Verhindern einer crashbedingten Betätigung einer Funktionskomponente in einem Fahrzeug |
| DE102011052329A1 (de) * | 2011-08-01 | 2013-02-07 | Druck- und Spritzgußwerk Hettich GmbH & Co. KG | Selbsteinzugssystem für ein bewegliches Möbelteil |
| DE102011122220A1 (de) * | 2011-12-23 | 2013-06-27 | Grass Gmbh | Dämpfungseinrichtung für ein bewegbares Möbelteil |
| DE102012011433A1 (de) | 2012-05-25 | 2013-11-28 | Vinzenz Bichler | Vorrichtung mit dilatantem Material zur adaptiven Bewegungsbegrenzung |
| DE102016114110A1 (de) | 2016-07-29 | 2018-02-01 | Betterguards Technology Gmbh | Vorrichtung zum adaptiven Dämpfen einer Körperbewegung |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075939A (en) * | 1958-10-08 | 1963-01-29 | Minnesota Mining & Mfg | Method of preparing dispersions from blend of fluorine containing polymers |
| GB1217446A (en) * | 1968-06-07 | 1970-12-31 | Sherwin Williams Co | Dilatant latex |
| US3728295A (en) * | 1968-06-07 | 1973-04-17 | Sherwin Williams Co | Dilatant latex of at least two aliphatic mono-unsaturated esters and an aliphatic mono-unsaturated carboxylic acid |
| US3770679A (en) * | 1970-12-16 | 1973-11-06 | Monsanto Co | Process for the preparation of a poly(vinyl acetate-dialkyl maleateacrylic acid) latex |
| US3770680A (en) * | 1971-05-03 | 1973-11-06 | Air Prod & Chem | Aqueous emulsion of interpolymer of vinyl acetate n methylol acrylamide and acrylic acid |
| US3784498A (en) * | 1972-04-21 | 1974-01-08 | Sinclair Koppers Co | Process for preparing low emulsifier synthetic latex |
| NL7414576A (nl) * | 1973-11-14 | 1975-05-16 | Dow Chemical Co | Met latex bekleed elektrostatisch vel. |
| DE2452585B2 (de) * | 1974-11-06 | 1981-07-30 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung scherstabiler wäßriger Copolymerisat-Dispersionen |
-
1980
- 1980-07-05 DE DE19803025562 patent/DE3025562A1/de not_active Withdrawn
-
1981
- 1981-06-12 DE DE8181104525T patent/DE3163371D1/de not_active Expired
- 1981-06-12 EP EP81104525A patent/EP0043464B1/de not_active Expired
- 1981-06-12 AT AT81104525T patent/ATE7302T1/de not_active IP Right Cessation
- 1981-07-01 US US06/279,548 patent/US4371636A/en not_active Expired - Fee Related
- 1981-07-01 JP JP56101369A patent/JPS5744614A/ja active Granted
- 1981-07-03 CA CA000381041A patent/CA1163033A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10687946B2 (en) | 2016-04-25 | 2020-06-23 | Betterguards Technology Gmbh | Device for stabilising joints |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0043464A3 (en) | 1982-02-10 |
| ATE7302T1 (de) | 1984-05-15 |
| JPH036166B2 (en, 2012) | 1991-01-29 |
| EP0043464B1 (de) | 1984-05-02 |
| DE3025562A1 (de) | 1982-02-11 |
| US4371636A (en) | 1983-02-01 |
| JPS5744614A (en) | 1982-03-13 |
| DE3163371D1 (en) | 1984-06-07 |
| EP0043464A2 (de) | 1982-01-13 |
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