EP0652929A1 - Liquides electrovisqueux homogenes - Google Patents

Liquides electrovisqueux homogenes

Info

Publication number: EP0652929A1
Authority: EP; European Patent Office
Prior art keywords: aluminum; weight; liquids according; electroviscous; linear
Prior art date: 1993-05-28
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

Application number

EP94916135A

Other languages

German (de)

English (en)

Other versions

EP0652929B1 (fr

Inventor

Dietrich Pirck

Hans-Dieter Grasshoff

Harald Kohnz

Peter Finmans

Tobias Carstensen

Dieter Jakubik

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wintershall Dea International AG

Original Assignee

RWE Dea AG fuer Mineraloel und Chemie

RWE Dea AG

Priority date (The priority date 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 date listed.)

1993-05-28

Filing date

1994-05-25

Publication date

1995-05-17

1994-05-25 Application filed by RWE Dea AG fuer Mineraloel und Chemie, RWE Dea AG filed Critical RWE Dea AG fuer Mineraloel und Chemie

1995-05-17 Publication of EP0652929A1 publication Critical patent/EP0652929A1/fr

1998-08-12 Application granted granted Critical

1998-08-12 Publication of EP0652929B1 publication Critical patent/EP0652929B1/fr

2014-05-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000007788 liquid Substances 0.000 title claims abstract description 34
229910052782 aluminium Inorganic materials 0.000 claims abstract description 32
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 20
239000000344 soap Substances 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 12
150000008064 anhydrides Chemical class 0.000 claims abstract description 8
150000007513 acids Chemical class 0.000 claims abstract description 7
239000007795 chemical reaction product Substances 0.000 claims abstract description 7
-1 aluminum compound Chemical class 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 6
239000012530 fluid Substances 0.000 claims description 6
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 5
150000001735 carboxylic acids Chemical class 0.000 claims description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
239000012456 homogeneous solution Substances 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
RIVXQHNOKLXDBP-UHFFFAOYSA-K aluminum;hydrogen carbonate Chemical class [Al+3].OC([O-])=O.OC([O-])=O.OC([O-])=O RIVXQHNOKLXDBP-UHFFFAOYSA-K 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 5
239000010720 hydraulic oil Substances 0.000 claims 3
150000004677 hydrates Chemical class 0.000 claims 1
125000005188 oxoalkyl group Chemical group 0.000 claims 1
229920000515 polycarbonate Polymers 0.000 claims 1
239000004417 polycarbonate Substances 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 4
239000004411 aluminium Substances 0.000 abstract 1
150000001399 aluminium compounds Chemical class 0.000 abstract 1
229940077746 antacid containing aluminium compound Drugs 0.000 abstract 1
239000000047 product Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
GGQRKYMKYMRZTF-UHFFFAOYSA-N 2,2,3,3-tetrakis(prop-1-enyl)butanedioic acid Chemical compound CC=CC(C=CC)(C(O)=O)C(C=CC)(C=CC)C(O)=O GGQRKYMKYMRZTF-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000002199 base oil Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
241000640882 Condea Species 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000013016 damping Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
230000035882 stress Effects 0.000 description 2
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-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
WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
MHALQPUFCVTXKV-UHFFFAOYSA-N 3-hex-1-enyloxolane-2,5-dione Chemical class CCCCC=CC1CC(=O)OC1=O MHALQPUFCVTXKV-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
239000005643 Pelargonic acid Substances 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000032683 aging Effects 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
239000013530 defoamer Substances 0.000 description 1
WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000005684 electric field Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
238000000034 method Methods 0.000 description 1
UEEXYHHZSOEEDG-UHFFFAOYSA-N methylaluminum(2+);oxygen(2-) Chemical compound [O-2].[Al+2]C UEEXYHHZSOEEDG-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
229920013639 polyalphaolefin Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
239000003566 sealing material Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000725 suspension Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/76—Esters containing free hydroxy or carboxyl groups
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/30—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms
- C10M129/34—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 7 or less carbon atoms polycarboxylic
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/001—Electrorheological fluids; smart fluids

Definitions

the invention relates to homogeneous electroviscous liquids (EVF).
Electroviscous liquids in the form of dispersions of finely divided hydrophilic solids in hydrophobic liquids have been known for some time.
the special feature of these liquids is that their flow behavior and thus their viscosity can be changed within wide limits by applying an electric field, so that there are wide-ranging and versatile possible uses.
Electroviscous liquids are intended for use in particular in the field of industrial and vehicle hydraulics, e.g. for machine and engine mounting or damping, for positioning workpieces, for vehicle level control, vehicle suspension and damping as well as for torque converters and automatic clutches.
the material composition of the known electroviscous liquids is very different.
the electroviscous liquids consist of three components, a disperse phase which contains silicates, zeolites, titanates, semiconductors, polysaccharides or organic polymers, an electrically non-conductive hydrophobic liquid as the liquid phase and a dispersant.
DE 35 36 934 A1 describes electroviscous liquids whose disperse phase contains aluminum silicates which have a water content of 1-25% by weight and whose atomic ratio Al / Si on the surface is between 0.15 and 0.80.
the object of the invention is therefore to provide homogeneous electroviscous liquids which meet the technical requirements of a modern industrial hydraulic fluid and which do not have the disadvantages described, but rather have a high electroviscous effect.
electroviscous liquids which contain or consist of aluminum soaps which are obtained by reacting one or more saturated and / or unsaturated monomeric, oligomeric and / or polymeric C3 to C 3 2-polycarboxylic acid ( n) with one or more carboxyl groups, their anhydrides and / or half-esters, their alcohol component (s) being linear or branched, mono- or polyvalent C- * to C- * 2 alcohols and / or their oligomers, with a or more of the following reactive aluminum compound (s)
Aluminum alkyls, oxoalkylenes, hydroxycarboxylates, oxocarboxylates, oxoalcoholates, alkoxy carboxylates, oxides and / or oxyhydrates are produced
the reactive aluminum compounds are preferably
reaction products of the polycarboxylic acids, anhydrides or half esters with the active aluminum compounds are used as aluminum soaps, in which all or some of the valences of the aluminum have been reacted.
the electroviscous liquids according to the invention preferably comprise the following individual components:
Component (a) 2-50% by weight, preferably 5-40% by weight, in particular 10-35% by weight of the aluminum soap, in homogeneous solution with component (b): 50-98% by weight, preferably 60 -95% by weight, in particular 65-90% by weight, of a conventional hydraulic base liquid, and additionally component (c): 0-10% by weight, preferably 0-5% by weight, in particular 0.1 up to 2% by weight, soluble, known hydraulic additives, each based on the total composition.
Component (a) consists of oligomeric, complex aluminum soaps based on reaction adducts of polycarboxylic acids or olefinic carboxylic acids, their anhydrides, semiesters or oligomers with the active aluminum compounds. Soap formation takes place completely or partially, for example by targeted partial hydrolysis, so that hydroxyl soap structures are formed.
Polycarboxylic acids are to be understood as carboxylic acids which are formed by reacting unsaturated carboxylic acids with one another or with olefins. Compounds which consist of 2 to 10, preferably 2 to 6, units are used as their oligomers.
Linear or branched mono- or polyhydric alcohols are used as alcohol components of the polycarboxylic acid half-esters.
the C number is advantageously determined by the selection of the base liquid in order to ensure the solubility of the corresponding reaction products.
component (a) examples include partial ester / aluminum soap adducts based on alkenyl succinic anhydrides, in particular n-hexenyl succinic anhydrides, diisobutenyl succinic anhydrides, tetrapropenyl succinic anhydrides, dodecenyl succinic anhydride.
alkenyl succinic anhydrides in particular n-hexenyl succinic anhydrides, diisobutenyl succinic anhydrides, tetrapropenyl succinic anhydrides, dodecenyl succinic anhydride.
olefin addition products of itaconic, citraconic and mesaconic acid are also suitable.
copolymers of unsaturated carboxylic acids for example maleic, fumaric, acrylic or ⁇ methacrylic acid, can be used.
Polyesters bearing carboxyl groups and based on saturated or aromatic dicarboxylic acids such as a
Component (b) includes hydraulic media such as conventional mineral oil selective raffinates, hydrocrackates, hydrogenates, poly-alpha-olefins or synthetic esters.
Component (c) comprises conventional hydraulic additives for optimizing the hydraulic product properties, e.g. of
component (c) examples are:
the olefin carboxylic acid half ester is initially introduced in dilute form and mixed with the Al carrier component with the rejection of moisture.
the nominal viscosity is adjusted with component (b), and additive is added with component (c) in accordance with the respective requirements.
the liquids produced in this way show a strongly increasing viscosity increase with a strengthening of the field in the voltage field from approx. 500 V / mm field strength.
the optimum responsiveness is in the range of 3-8 kV / mm field strength with an aluminum content of preferably 0.1 to 0.5%.
the initial viscosity of the EVF can range from 15 to 6000 mPA-s at 40 ° C.
Example 1 is based on a polycarboxylic acid which has not been reacted with an active aluminum compound. It turned out to be ineffective.
Examples 2 to 4 describe reaction products according to the invention.
the corresponding electrorheological measurement results are shown in the attached table.
the final mix had one
Example 2 50 g of the tetrapropenylsuccinic acid half ester of Example 1 were dissolved in 150 ml of toluene and cooled to -30 ° C. and rendered inert. 33 ml of a 10% solution of ⁇ methyl aluminum oxide (product from Witco) were added with a syringe.
⁇ methyl aluminum oxide product from Witco
a mixture of 10 g of the tetrapropenylsuccinic acid half-ester of Example 1, 2.5 g of aluminum oxide hydrate (Disperal R ', Condea Chemie), 15 g of pelargonic acid and 130 g of naphthenic white oil as hydraulic base oil were heated to 120 ° C. for one hour. At 80 - 100 ° C by a

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Lubricants (AREA)
Fluid-Pressure Circuits (AREA)
Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Physical Or Chemical Processes And Apparatus (AREA)

EP94916135A 1993-05-28 1994-05-25 Liquides electrovisqueux homogenes Expired - Lifetime EP0652929B1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE4317764A DE4317764A1 (de)	1993-05-28	1993-05-28	Homogene elektroviskose Flüssigkeiten
DE4317764		1993-05-28
PCT/DE1994/000595 WO1994028096A1 (fr)	1993-05-28	1994-05-25	Liquides electrovisqueux homogenes

Publications (2)

Publication Number	Publication Date
EP0652929A1 true EP0652929A1 (fr)	1995-05-17
EP0652929B1 EP0652929B1 (fr)	1998-08-12

Family

ID=6489119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP94916135A Expired - Lifetime EP0652929B1 (fr)	1993-05-28	1994-05-25	Liquides electrovisqueux homogenes

Country Status (11)

Country	Link
EP (1)	EP0652929B1 (fr)
JP (1)	JP3433942B2 (fr)
KR (1)	KR100279494B1 (fr)
AT (1)	ATE169666T1 (fr)
AU (1)	AU6793094A (fr)
BR (1)	BR9405380A (fr)
CA (1)	CA2141205C (fr)
CZ (1)	CZ292137B6 (fr)
DE (3)	DE4317764A1 (fr)
RU (1)	RU95106492A (fr)
WO (1)	WO1994028096A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10108533C2 (de) *	2001-02-22	2003-09-25	Schenck Ag Carl	Drehmomentwandler auf Basis elektrorheologischer und/oder magnetorheologischer Flüssigkeiten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3047507A (en) *	1960-04-04	1962-07-31	Wefco Inc	Field responsive force transmitting compositions
DE4139065A1 (de)	1991-11-28	1993-06-17	Rwe Dea Ag	Homogene elektroviskose fluessigkeiten

1993
- 1993-05-28 DE DE4317764A patent/DE4317764A1/de not_active Withdrawn
1994
- 1994-05-25 AU AU67930/94A patent/AU6793094A/en not_active Abandoned
- 1994-05-25 EP EP94916135A patent/EP0652929B1/fr not_active Expired - Lifetime
- 1994-05-25 JP JP50010595A patent/JP3433942B2/ja not_active Expired - Lifetime
- 1994-05-25 DE DE59406666T patent/DE59406666D1/de not_active Expired - Fee Related
- 1994-05-25 WO PCT/DE1994/000595 patent/WO1994028096A1/fr not_active Ceased
- 1994-05-25 KR KR1019950700322A patent/KR100279494B1/ko not_active Expired - Lifetime
- 1994-05-25 RU RU95106492/04A patent/RU95106492A/ru unknown
- 1994-05-25 DE DE4493438T patent/DE4493438D2/de not_active Expired - Fee Related
- 1994-05-25 AT AT94916135T patent/ATE169666T1/de not_active IP Right Cessation
- 1994-05-25 CZ CZ1995178A patent/CZ292137B6/cs not_active IP Right Cessation
- 1994-05-25 CA CA002141205A patent/CA2141205C/fr not_active Expired - Lifetime
- 1994-05-25 BR BR9405380-4A patent/BR9405380A/pt not_active Application Discontinuation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9428096A1 *

Also Published As

Publication number	Publication date
CA2141205A1 (fr)	1994-12-08
DE4317764A1 (de)	1994-12-01
AU6793094A (en)	1994-12-20
KR100279494B1 (ko)	2001-03-02
JP3433942B2 (ja)	2003-08-04
CZ292137B6 (cs)	2003-08-13
DE59406666D1 (de)	1998-09-17
CZ17895A3 (en)	1995-09-13
RU95106492A (ru)	1996-11-20
EP0652929B1 (fr)	1998-08-12
CA2141205C (fr)	2002-10-15
WO1994028096A1 (fr)	1994-12-08
ATE169666T1 (de)	1998-08-15
DE4493438D2 (de)	1996-08-22
JPH09505324A (ja)	1997-05-27
BR9405380A (pt)	1999-09-08

Legal Events

Date	Code	Title	Description
1995-03-31	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1995-05-17	17P	Request for examination filed	Effective date: 19950207
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1995-09-06	17Q	First examination report despatched	Effective date: 19950721
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1998-02-12	GRAH	Despatch of communication of intention to grant a patent	Free format text: ORIGINAL CODE: EPIDOS IGRA
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