EP1192239B1 - Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens - Google Patents
Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens Download PDFInfo
- Publication number
- EP1192239B1 EP1192239B1 EP00922705A EP00922705A EP1192239B1 EP 1192239 B1 EP1192239 B1 EP 1192239B1 EP 00922705 A EP00922705 A EP 00922705A EP 00922705 A EP00922705 A EP 00922705A EP 1192239 B1 EP1192239 B1 EP 1192239B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- additive
- chosen
- weight
- anhydride
- 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 - Lifetime
Links
- 239000000654 additive Substances 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 230000000996 additive effect Effects 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229920001577 copolymer Polymers 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 5
- -1 amine compounds Chemical class 0.000 claims abstract 3
- 239000000446 fuel Substances 0.000 claims description 15
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- BRLPEEKPYKAERE-UHFFFAOYSA-N 3-dodecylfuran-2,5-dione Chemical compound CCCCCCCCCCCCC1=CC(=O)OC1=O BRLPEEKPYKAERE-UHFFFAOYSA-N 0.000 claims description 2
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 claims description 2
- GLGZPKHFMGAJAY-UHFFFAOYSA-N 3-octadecylfuran-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(=O)OC1=O GLGZPKHFMGAJAY-UHFFFAOYSA-N 0.000 claims description 2
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 2
- 229920003146 methacrylic ester copolymer Polymers 0.000 claims description 2
- JCDVRVQHKIBXTB-UHFFFAOYSA-N n'-[2-(docosylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCNCCNCCN JCDVRVQHKIBXTB-UHFFFAOYSA-N 0.000 claims description 2
- DBNYMXPUYZOHQN-UHFFFAOYSA-N n'-[2-(octadecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCNCCN DBNYMXPUYZOHQN-UHFFFAOYSA-N 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- HWEHWGJKBYHBQR-UHFFFAOYSA-N 3-hexadec-1-enylfuran-2,5-dione Chemical compound CCCCCCCCCCCCCCC=CC1=CC(=O)OC1=O HWEHWGJKBYHBQR-UHFFFAOYSA-N 0.000 claims 1
- LPBLFVHSSYPGBV-UHFFFAOYSA-N 3-hexadecylfuran-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC1=CC(=O)OC1=O LPBLFVHSSYPGBV-UHFFFAOYSA-N 0.000 claims 1
- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 claims 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000004062 sedimentation Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 238000010583 slow cooling Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000012188 paraffin wax Substances 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000002283 diesel fuel Substances 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- USQOVYLRWBOSQC-HNNXBMFYSA-N CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O Chemical compound CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O USQOVYLRWBOSQC-HNNXBMFYSA-N 0.000 description 1
- 102100023055 Neurofilament medium polypeptide Human genes 0.000 description 1
- 101710109612 Neurofilament medium polypeptide Proteins 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical group CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical group CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000007 visual effect Effects 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
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
-
- 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
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
Definitions
- the present invention relates to a new composition of multifunctional additives improving the cold operability of middle distillates, especially in during slow cooling processes during storage fuels and fuels at low temperatures. It aims in particular to improve the anti-sedimentation properties for application in fuels for Diesel engines and in fuels such as fuel oils domestic for boilers.
- Cold operability corresponds to a temperature limit at which middle distillates can be used without clogging problem. She is intermediate between cloud point temperature (ASTM D 2500-66) characteristic of the onset of crystallization of paraffins in the distillate and the pour point of the latter (ASTM D 97-66).
- paraffins are crystallized at bottom of the tank, they can be dragged starting in the engine and clogging in particular the filters and prefilters arranged upstream of the injection systems (pump and injectors).
- paraffins precipitate at the bottom of the tank and may be entrained and obstruct upstream pipes pump and boiler supply system (nozzle and filter). It is obvious that the presence of solids, such as paraffin crystals, prevents the normal circulation of the middle distillate.
- TLF additives Temporal Limit of Filterability
- the present invention relates to a composition multifunctional additives for lowering and maintain the cold operability temperature of middle distillates, so that during a stage of slow cooling during storage in a closed enclosure, up to temperatures above -20 ° C, we do not observe no sedimentation of the paraffins contained in the middle distillates.
- the composition of additives is obtained by combining 50 to 80% AB and 20 to 50% by weight of the CD reaction product.
- the composition of additives comprises from 50 to 80% by weight of a combination AB, CD in an AB / CD molar ratio varying from 0.2 to 4, and from 20 to 50% by weight of a mixture of AD, CB in a ratio AD / CB molar varying from 0.2 to 4.
- the carboxylic compound (A) is preferably chosen in the group comprising dodecylmaleic anhydrides, dodecenylmaleic, hexadecylmaleic, hexadecenylmaleic octadecylmaleic, octadecenylmaleic, eicosylmaleic and éicosénylmaléique.
- the polyalkyleneamine (B) is preferably chosen in the group comprising diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine and tetrapropylene.
- the copolymer (C) is preferably a copolymer containing 45 to 65 mol% of at least one acid unit carboxylic and from 55 to 35 mol% of at least one ester unit alkylated.
- the carboxylic acid units are chosen preferably among the units resulting from acids acrylic and methacrylic, and alkyl ester patterns among the patterns resulting from acrylic esters and methacrylics, and their derivatives.
- the copolymer (C) is chosen from acrylic acid / methacrylic ester copolymers and methacrylic acid / acrylic ester copolymers containing 45 to 65 mole% of acid units and 55 to 35 mole% of ester patterns.
- the N-alkylpolyalkylenepolyamine (D) is preference chosen from the group comprising N-alkylethylenediamines, N-alkylpropylenediamines, N-alkylbutylenediamines, N-alkyldiethylenetriamines, N-alkyldipropylenetriamines, N-alkyldibutylenetriamines, N-alkyltriethylenetetramines, N-alkyltripropylenetetramines and N-alkyltributylenetetramines having a alkyl radical comprising from 12 to 22 carbon atoms.
- D is chosen from N-dodecyldipropylenetriamine, N-octadecyldipropylene triamine, N-octadecyldiethylenetriamine and N-docosyldiethylenetriamine.
- a second object of the invention is a fuel containing a major part of middle distillate containing usually a filterability additive, and some minor, for example 50 to 1000 ppm of a composition Multifunctional cold operability additives for slow cooling.
- This example presents the two methods of cooling implemented as well as the composition of diesel and additives tested.
- the quench cooling method described in standard NFT M07-085, consists in pouring a sample of distillate in a graduated cylinder in volume and place for 24 hours in a refrigerated cabinet at one temperature generally set between -13 and -20 ° C, i.e. a temperature at least 1 ° C lower than its temperature cloud point, and at least 6 ° C higher than its pour point temperature.
- the anti-sedimentation function of the additive compositions is therefore effective. If the upper phase is clear and a cloudy compaction appears at the bottom of the test tube, the sedimentation is important and the composition of additives ineffective in anti-sedimentation.
- the slow cooling method is to introduce the sample of diesel fuel with or without additives into a cylinder graduated in volume, to place in a cabinet refrigerated at a temperature 10 ° C higher than the cloud point temperature of said diesel.
- the sample is gradually cooled from this temperature from 1 to 3 ° C / hour, up to a final test temperature that can reach -15 to -20 ° C. Once the final temperature reached, the sample is kept for 24 hours at this temperature, then we do the visual rating already mentioned for the rapid quenching method, as well as the samples from the top and bottom of the test piece to determine the temperatures Tcc and TLF of these different phases. Interpretation of the results is identical to the rapid quenching method.
- This example aims to show the difference between the quench cooling method and the method by slow cooling to 1 ° C per hour and therefore the interest to select additives reproducing the phenomenon of actual cooling of a stopped car tank and therefore the diesel cooling process.
- composition of multifunctional additives is all the more effective the smaller the sum of the six differences on the three diesel fuels.
- Ranking difference Tcc TLF gap difference Tcc TLF gap difference Tcc TLF gap Gi + TLF 21.2 11 17.8 10 19.7 10 89.7 11 AD 2.1 0 3.9 3 9.4 1 19.4 1 st AB 6.2 4 15.8 11 12.0 2 51 4 CD 2.2 6 7.2 3 12.7 4 35.1 2 CB 16.1 6 17.0 9 19.2 11 78.3 10 X 1 5.0 0 15.5 6 17.3 9 52.8 5 X 2 4.6 0 14.3 7 17.1 10 53 6 X 3 8.2 2 16.3 9 16.2 8 59.7 8 X 4 9.6 3 17.0 11 13.7 4 58.3 7 X 5 10.5 3 12.3 5 12.0 5 47.8 3 X 6 11.4 3 16.0 9 18.5 9 66.9 9 Slow method 1
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Beans For Foods Or Fodder (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Confectionery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- General Preparation And Processing Of Foods (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200030075T SI1192239T1 (en) | 1999-04-26 | 2000-04-21 | Multifunctional additive composition for cold process treatment of middle distillates |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9905235 | 1999-04-26 | ||
| FR9905235A FR2792646B1 (fr) | 1999-04-26 | 1999-04-26 | Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens |
| PCT/FR2000/001052 WO2000065000A1 (fr) | 1999-04-26 | 2000-04-21 | Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1192239A1 EP1192239A1 (fr) | 2002-04-03 |
| EP1192239B1 true EP1192239B1 (fr) | 2003-02-05 |
Family
ID=9544841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP00922705A Expired - Lifetime EP1192239B1 (fr) | 1999-04-26 | 2000-04-21 | Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6623536B1 (sk) |
| EP (1) | EP1192239B1 (sk) |
| JP (1) | JP2002543237A (sk) |
| KR (1) | KR100657047B1 (sk) |
| AT (1) | ATE232233T1 (sk) |
| CA (1) | CA2367927C (sk) |
| CZ (1) | CZ296126B6 (sk) |
| DE (1) | DE60001368T2 (sk) |
| DK (1) | DK1192239T3 (sk) |
| ES (1) | ES2192175T3 (sk) |
| FR (1) | FR2792646B1 (sk) |
| PL (1) | PL192234B1 (sk) |
| PT (1) | PT1192239E (sk) |
| SI (1) | SI1192239T1 (sk) |
| SK (1) | SK285752B6 (sk) |
| WO (1) | WO2000065000A1 (sk) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2802940B1 (fr) * | 1999-12-28 | 2003-11-07 | Elf Antar France | Composition d'additifs multifonctionnels d'operabilite a froid des distillats moyens |
| FR2839315B1 (fr) * | 2002-05-03 | 2006-04-28 | Totalfinaelf France | Additif pour ameliorer la stabilite thermique de compositions d'hydrocarbures |
| US20050138859A1 (en) * | 2003-12-16 | 2005-06-30 | Graham Jackson | Cold flow improver compositions for fuels |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2490669A1 (fr) * | 1980-09-19 | 1982-03-26 | Elf France | Nouvelles compositions d'additifs permettant l'amelioration de la temperature limite de filtrabilite et l'inhibition simultanee des cristaux de n-paraffines formes lors du stockage a basse temperature des distillats moyens |
| FR2510598A1 (fr) * | 1981-07-30 | 1983-02-04 | Inst Francais Du Petrole | Utilisation d'additifs azotes comme agents d'abaissement du point de trouble des distillats moyens d'hydrocarbures et compositions de distillats moyens d'hydrocarbures renfermant lesdits additifs |
| FR2633638B1 (fr) * | 1988-06-29 | 1991-04-19 | Inst Francais Du Petrole | Formulations d'additifs azotes pour carburants moteurs et les carburants moteurs les contenant |
| IT1229659B (it) * | 1989-04-21 | 1991-09-06 | Euron Spa | Additivo detergente, disperdente ed anti ruggine per combustibili ed oli lubrificanti. |
| JPH0751711B2 (ja) * | 1991-11-26 | 1995-06-05 | 三洋化成工業株式会社 | 燃料油用流動性向上剤および燃料油組成物 |
| FR2699550B1 (fr) * | 1992-12-17 | 1995-01-27 | Inst Francais Du Petrole | Composition de distillat moyen de pétrole contenant des additifs azotés utilisables comme agents limitant la vitesse de sédimentation des paraffines. |
| FR2710652B1 (fr) * | 1993-09-30 | 1995-12-01 | Elf Antar France | Composition d'additifs d'opérabilité à froid des distillats moyens. |
| DE4430294A1 (de) * | 1994-08-26 | 1996-02-29 | Basf Ag | Polymermischungen und ihre Verwendung als Zusatz für Erdölmitteldestillate |
| FR2735494B1 (fr) * | 1995-06-13 | 1997-10-10 | Elf Antar France | Additif bifonctionnel de tenue a froid et composition de carburant |
| CA2189918C (en) * | 1995-11-13 | 2005-01-25 | Richard Mark Scott | Dispersant additives |
| US5755834A (en) * | 1996-03-06 | 1998-05-26 | Exxon Chemical Patents Inc. | Low temperature enhanced distillate fuels |
| GB9610363D0 (en) * | 1996-05-17 | 1996-07-24 | Ethyl Petroleum Additives Ltd | Fuel additives and compositions |
| DE19622052A1 (de) * | 1996-05-31 | 1997-12-04 | Basf Ag | Paraffindispergatoren für Erdölmitteldestillate |
-
1999
- 1999-04-26 FR FR9905235A patent/FR2792646B1/fr not_active Expired - Fee Related
-
2000
- 2000-04-12 US US09/958,718 patent/US6623536B1/en not_active Expired - Fee Related
- 2000-04-21 JP JP2000614339A patent/JP2002543237A/ja active Pending
- 2000-04-21 DE DE60001368T patent/DE60001368T2/de not_active Expired - Lifetime
- 2000-04-21 WO PCT/FR2000/001052 patent/WO2000065000A1/fr active IP Right Grant
- 2000-04-21 PL PL352553A patent/PL192234B1/pl not_active IP Right Cessation
- 2000-04-21 SK SK1513-2001A patent/SK285752B6/sk unknown
- 2000-04-21 CZ CZ20013842A patent/CZ296126B6/cs not_active IP Right Cessation
- 2000-04-21 AT AT00922705T patent/ATE232233T1/de active
- 2000-04-21 KR KR1020017013764A patent/KR100657047B1/ko not_active IP Right Cessation
- 2000-04-21 ES ES00922705T patent/ES2192175T3/es not_active Expired - Lifetime
- 2000-04-21 PT PT00922705T patent/PT1192239E/pt unknown
- 2000-04-21 DK DK00922705T patent/DK1192239T3/da active
- 2000-04-21 EP EP00922705A patent/EP1192239B1/fr not_active Expired - Lifetime
- 2000-04-21 SI SI200030075T patent/SI1192239T1/xx unknown
- 2000-04-21 CA CA002367927A patent/CA2367927C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL192234B1 (pl) | 2006-09-29 |
| DE60001368T2 (de) | 2003-11-27 |
| WO2000065000A1 (fr) | 2000-11-02 |
| FR2792646B1 (fr) | 2001-07-27 |
| DE60001368D1 (de) | 2003-03-13 |
| SK15132001A3 (sk) | 2002-05-09 |
| ES2192175T3 (es) | 2003-10-01 |
| CA2367927C (en) | 2008-06-17 |
| CA2367927A1 (en) | 2000-11-02 |
| PL352553A1 (en) | 2003-08-25 |
| DK1192239T3 (da) | 2003-05-26 |
| KR100657047B1 (ko) | 2006-12-12 |
| EP1192239A1 (fr) | 2002-04-03 |
| SK285752B6 (sk) | 2007-07-06 |
| SI1192239T1 (en) | 2003-06-30 |
| CZ296126B6 (cs) | 2006-01-11 |
| CZ20013842A3 (cs) | 2002-05-15 |
| KR20020050755A (ko) | 2002-06-27 |
| ATE232233T1 (de) | 2003-02-15 |
| PT1192239E (pt) | 2003-06-30 |
| JP2002543237A (ja) | 2002-12-17 |
| US6623536B1 (en) | 2003-09-23 |
| FR2792646A1 (fr) | 2000-10-27 |
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