EP0000424A1 - Lineare oder verzweigte Ester-Ätherblockcopolymere und ihre Verwendung als oberflächenaktive Stoffe allein oder in Mischungen mit üblichen oberflächenaktiven Stoffen - Google Patents
Lineare oder verzweigte Ester-Ätherblockcopolymere und ihre Verwendung als oberflächenaktive Stoffe allein oder in Mischungen mit üblichen oberflächenaktiven Stoffen Download PDFInfo
- Publication number
- EP0000424A1 EP0000424A1 EP78300074A EP78300074A EP0000424A1 EP 0000424 A1 EP0000424 A1 EP 0000424A1 EP 78300074 A EP78300074 A EP 78300074A EP 78300074 A EP78300074 A EP 78300074A EP 0000424 A1 EP0000424 A1 EP 0000424A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- soluble
- molecular weight
- weight
- copolymer
- component
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 38
- 229920001400 block copolymer Polymers 0.000 title abstract description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims abstract description 45
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 13
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 8
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 27
- 239000002202 Polyethylene glycol Substances 0.000 claims description 23
- 229920001223 polyethylene glycol Polymers 0.000 claims description 23
- 150000003077 polyols Chemical class 0.000 claims description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 16
- 229920000570 polyether Polymers 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 16
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 8
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000012071 phase Substances 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- 239000000839 emulsion Substances 0.000 abstract description 16
- 239000003921 oil Substances 0.000 abstract description 14
- 238000004945 emulsification Methods 0.000 abstract description 5
- 239000003995 emulsifying agent Substances 0.000 abstract description 3
- 239000000295 fuel oil Substances 0.000 abstract description 3
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- 239000000080 wetting agent Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 229920000578 graft copolymer Polymers 0.000 description 14
- -1 poly(ethylene-propylene) Polymers 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 125000003827 glycol group Chemical group 0.000 description 7
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002283 diesel fuel Substances 0.000 description 6
- 239000003350 kerosene Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000009884 interesterification Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- ZCGHEBMEQXMRQL-UHFFFAOYSA-N benzyl 2-carbamoylpyrrolidine-1-carboxylate Chemical compound NC(=O)C1CCCN1C(=O)OCC1=CC=CC=C1 ZCGHEBMEQXMRQL-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010763 heavy fuel oil Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/32—Liquid carbonaceous fuels consisting of coal-oil suspensions or aqueous emulsions or oil emulsions
- C10L1/328—Oil emulsions containing water or any other hydrophilic phase
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
- C09K23/44—Ether carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Polyethers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2919277 | 1977-07-12 | ||
| GB2919277 | 1977-07-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000424A1 true EP0000424A1 (de) | 1979-01-24 |
| EP0000424B1 EP0000424B1 (de) | 1984-02-01 |
Family
ID=10287624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78300074A Expired EP0000424B1 (de) | 1977-07-12 | 1978-06-23 | Lineare oder verzweigte Ester-Ätherblockcopolymere und ihre Verwendung als oberflächenaktive Stoffe allein oder in Mischungen mit üblichen oberflächenaktiven Stoffen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4203877A (de) |
| EP (1) | EP0000424B1 (de) |
| JP (3) | JPS5418898A (de) |
| AU (1) | AU523572B2 (de) |
| CA (1) | CA1126288A (de) |
| DE (1) | DE2862369D1 (de) |
| DK (1) | DK311278A (de) |
| ES (1) | ES471652A1 (de) |
| IT (1) | IT1097231B (de) |
| NZ (1) | NZ187767A (de) |
| ZA (1) | ZA783802B (de) |
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007731A2 (de) * | 1978-07-28 | 1980-02-06 | Imperial Chemical Industries Plc | Verfahren zur Herstellung von Dispersionen fester hydrophober Teilchen (z.B. Pestizide) und die so erhaltenen Teilchen-Dispersionen |
| EP0033170A2 (de) * | 1980-01-24 | 1981-08-05 | Shell Internationale Researchmaatschappij B.V. | Hydraulische Flüssigkeit, hydraulische Ausrüstung, die diese Flüssigkeit enthält, und Konzentrat dieser Flüssigkeit |
| EP0164817A2 (de) * | 1984-03-21 | 1985-12-18 | Imperial Chemical Industries Plc | Detergens |
| WO1993015257A1 (de) * | 1992-01-25 | 1993-08-05 | Henkel Kommanditgesellschaft Auf Aktien | Verwendung von blockcopolyestern mit polyalkylenglykolblöcken als glättemittel in spinnpräparationen |
| EP0584771A1 (de) * | 1992-08-26 | 1994-03-02 | The B.F. Goodrich Company | Einfach zu dispergieren Polycarboxylsäureverdickungsmitteln |
| EP0623630A2 (de) * | 1993-05-07 | 1994-11-09 | BASF Aktiengesellschaft | Wasser-in-Öl-Polymeremulsionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO1995032227A1 (de) * | 1994-05-25 | 1995-11-30 | Basf Aktiengesellschaft | Verfahren zur herstellung von stabilen wasser-in-öl-emulsionen von hydrolysierten polymerisaten von n-vinylamiden und ihre verwendung |
| DE4420516A1 (de) * | 1994-06-13 | 1995-12-14 | Henkel Kgaa | Polyolpolyhydroxystearate |
| WO1996007689A1 (en) * | 1994-09-02 | 1996-03-14 | Ici Americas Inc. | Polyalkylene glycol hydroxy carboxylic acid dispersant |
| WO1996016728A1 (de) * | 1994-12-02 | 1996-06-06 | Henkel Kommanditgesellschaft Auf Aktien | Wasser-in-öl-emulsionen |
| WO1996028245A1 (de) * | 1995-03-15 | 1996-09-19 | Henkel Kommanditgesellschaft Auf Aktien | Multiple w/o/w-emulsionen |
| DE19533539A1 (de) * | 1995-09-11 | 1997-03-13 | Henkel Kgaa | O/W-Emulgatoren |
| WO1998009998A1 (en) * | 1996-09-03 | 1998-03-12 | Imperial Chemical Industries Plc | Polyacrylamide polymerisation |
| EP1297938A1 (de) * | 2001-09-28 | 2003-04-02 | Goldschmidt AG | Gleit- und Trennmittel für Gummiformkörper |
| WO2004041769A1 (de) * | 2002-11-08 | 2004-05-21 | Cognis Ip Management Gmbh | Verfahren zur herstellung eines esters |
| WO2005107681A1 (de) * | 2004-04-29 | 2005-11-17 | Cognis Ip Management Gmbh | Emulgatorkonzentrat für kosmetische zusammensetzung |
| US7300507B2 (en) | 2004-11-05 | 2007-11-27 | Gr Advanced Materials Ltd. | Emulsion ink |
| FR2906530A1 (fr) * | 2006-09-29 | 2008-04-04 | Stearinerie Dubois Fils Sa | Procede de synthese d'esters d'estolides. |
| US7396396B2 (en) | 2003-11-10 | 2008-07-08 | Gr Advanced Materials Ltd. | Emulsion ink |
| WO2011070051A2 (en) | 2009-12-09 | 2011-06-16 | Basf Se | Liquid suspension concentrate formulations containing saflufenacil |
| WO2011116049A1 (en) | 2010-03-17 | 2011-09-22 | Croda, Inc. | Polymeric surfactant |
| WO2014019975A1 (en) | 2012-07-30 | 2014-02-06 | Shell Internationale Reserach Maatschappij B.V. | Lubricating oil composition for internal combustion engines |
| US8653002B2 (en) | 2009-08-27 | 2014-02-18 | Basf Se | Aqueous suspension concentrate formulations containing saflufenacil |
| US8778838B2 (en) | 2009-08-27 | 2014-07-15 | Basf Se | Aqueous concentrate formulations containing saflufenacil and glyphosate |
| EP2784038A1 (de) | 2013-03-26 | 2014-10-01 | Basf Se | Fließmittel auf Zuschlägen |
| US9545104B2 (en) | 2009-12-09 | 2017-01-17 | Basf Se | Liquid suspension concentrate formulations containing saflufenacil and glyphosate |
| US9586864B2 (en) | 2013-03-26 | 2017-03-07 | Basf Se | Rapidly suspendable pulverulent composition |
| US10266700B2 (en) | 2013-03-26 | 2019-04-23 | Basf Se | Rapidly suspendable pulverulent composition |
| WO2019232106A1 (en) * | 2018-05-30 | 2019-12-05 | The Procter & Gamble Company | Liquid fabric enhancers comprising branched polyester molecules |
| WO2020078958A1 (en) | 2018-10-16 | 2020-04-23 | Intervet International B.V. | Stable emulsions of bacterial antigens |
| WO2020078941A1 (en) | 2018-10-16 | 2020-04-23 | Intervet International B.V. | Emulsion vaccine for fish |
| US11041137B2 (en) | 2013-10-29 | 2021-06-22 | Croda, Inc. | Lubricant composition comprising hydroxycarboxylic acid derived friction modifier |
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| US3847851A (en) * | 1972-06-16 | 1974-11-12 | Dainippon Toryo Kk | Thermosetting synthetic polymer dispersions and process for production thereof |
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- 1978-06-23 DE DE7878300074T patent/DE2862369D1/de not_active Expired
- 1978-07-03 US US05/921,563 patent/US4203877A/en not_active Expired - Lifetime
- 1978-07-03 NZ NZ187767A patent/NZ187767A/xx unknown
- 1978-07-03 ZA ZA00783802A patent/ZA783802B/xx unknown
- 1978-07-05 AU AU37773/78A patent/AU523572B2/en not_active Expired
- 1978-07-07 CA CA306,985A patent/CA1126288A/en not_active Expired
- 1978-07-11 DK DK783112A patent/DK311278A/da not_active Application Discontinuation
- 1978-07-12 ES ES471652A patent/ES471652A1/es not_active Expired
- 1978-07-12 JP JP8413078A patent/JPS5418898A/ja active Granted
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| EP0007731A2 (de) * | 1978-07-28 | 1980-02-06 | Imperial Chemical Industries Plc | Verfahren zur Herstellung von Dispersionen fester hydrophober Teilchen (z.B. Pestizide) und die so erhaltenen Teilchen-Dispersionen |
| EP0007731A3 (de) * | 1978-07-28 | 1980-02-20 | Imperial Chemical Industries Plc | Verfahren zur Herstellung von Dispersionen fester hydrophober Teilchen (z.B. Pestizide) und die so erhaltenen Teilchen-Dispersionen |
| EP0033170A2 (de) * | 1980-01-24 | 1981-08-05 | Shell Internationale Researchmaatschappij B.V. | Hydraulische Flüssigkeit, hydraulische Ausrüstung, die diese Flüssigkeit enthält, und Konzentrat dieser Flüssigkeit |
| EP0033170A3 (en) * | 1980-01-24 | 1981-10-07 | Shell Internationale Research Maatschappij B.V. | Hydraulic fluid, hydraulic equipment containing this fluid and a concentrate of this fluid |
| US4354949A (en) * | 1980-01-24 | 1982-10-19 | Shell Oil Company | Hydraulic fluid, hydraulic equipment containing this fluid and a concentrate of this fluid |
| EP0164817A2 (de) * | 1984-03-21 | 1985-12-18 | Imperial Chemical Industries Plc | Detergens |
| EP0164817A3 (en) * | 1984-03-21 | 1987-08-19 | Imperial Chemical Industries Plc | Surfactant |
| WO1993015257A1 (de) * | 1992-01-25 | 1993-08-05 | Henkel Kommanditgesellschaft Auf Aktien | Verwendung von blockcopolyestern mit polyalkylenglykolblöcken als glättemittel in spinnpräparationen |
| EP0584771A1 (de) * | 1992-08-26 | 1994-03-02 | The B.F. Goodrich Company | Einfach zu dispergieren Polycarboxylsäureverdickungsmitteln |
| EP0623630A2 (de) * | 1993-05-07 | 1994-11-09 | BASF Aktiengesellschaft | Wasser-in-Öl-Polymeremulsionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP0623630A3 (de) * | 1993-05-07 | 1995-03-29 | Basf Ag | Wasser-in-Öl-Polymeremulsionen, Verfahren zu ihrer Herstellung und ihre Verwendung. |
| WO1995032227A1 (de) * | 1994-05-25 | 1995-11-30 | Basf Aktiengesellschaft | Verfahren zur herstellung von stabilen wasser-in-öl-emulsionen von hydrolysierten polymerisaten von n-vinylamiden und ihre verwendung |
| DE4420516A1 (de) * | 1994-06-13 | 1995-12-14 | Henkel Kgaa | Polyolpolyhydroxystearate |
| DE4420516C2 (de) * | 1994-06-13 | 1998-10-22 | Henkel Kgaa | Polyglycerinpolyhydroxystearate |
| WO1996007689A1 (en) * | 1994-09-02 | 1996-03-14 | Ici Americas Inc. | Polyalkylene glycol hydroxy carboxylic acid dispersant |
| WO1996016728A1 (de) * | 1994-12-02 | 1996-06-06 | Henkel Kommanditgesellschaft Auf Aktien | Wasser-in-öl-emulsionen |
| US5863461A (en) * | 1994-12-02 | 1999-01-26 | Henkel Kommanditgesellschaft Auf Aktien | Water-in-oil emulsions |
| WO1996028245A1 (de) * | 1995-03-15 | 1996-09-19 | Henkel Kommanditgesellschaft Auf Aktien | Multiple w/o/w-emulsionen |
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Also Published As
| Publication number | Publication date |
|---|---|
| JPS5418898A (en) | 1979-02-13 |
| ZA783802B (en) | 1979-07-25 |
| CA1126288A (en) | 1982-06-22 |
| NZ187767A (en) | 1980-10-24 |
| US4203877A (en) | 1980-05-20 |
| ES471652A1 (es) | 1979-10-01 |
| JPH03174240A (ja) | 1991-07-29 |
| AU3777378A (en) | 1980-01-10 |
| AU523572B2 (en) | 1982-08-05 |
| EP0000424B1 (de) | 1984-02-01 |
| JPH0317534B2 (de) | 1991-03-08 |
| DE2862369D1 (en) | 1984-03-08 |
| DK311278A (da) | 1979-01-13 |
| IT7825616A0 (it) | 1978-07-12 |
| JPH0411251B2 (de) | 1992-02-27 |
| JPS6470525A (en) | 1989-03-16 |
| IT1097231B (it) | 1985-08-26 |
| JPH0134532B2 (de) | 1989-07-19 |
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