CA1067243A - Crude oil demulsifiers - Google Patents
Crude oil demulsifiersInfo
- Publication number
- CA1067243A CA1067243A CA236,332A CA236332A CA1067243A CA 1067243 A CA1067243 A CA 1067243A CA 236332 A CA236332 A CA 236332A CA 1067243 A CA1067243 A CA 1067243A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- ethylene oxide
- addition
- product
- block polymer
- 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
- 239000010779 crude oil Substances 0.000 title claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 229920001451 polypropylene glycol Polymers 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- -1 aliphatic aldehydes Chemical class 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000000839 emulsion Substances 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- 239000007859 condensation product Substances 0.000 claims abstract description 7
- 239000012442 inert solvent Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 238000007792 addition Methods 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- 206010013457 Dissociation Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 208000018459 dissociative disease Diseases 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyethers (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742445873 DE2445873C3 (de) | 1974-09-26 | Verfahren zur Herstellung von verätherten Phenol-Aldehyd-Kondensationsprodukten und deren Verwendung zum Spalten von Rohölemulsionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067243A true CA1067243A (en) | 1979-11-27 |
Family
ID=5926731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA236,332A Expired CA1067243A (en) | 1974-09-26 | 1975-09-25 | Crude oil demulsifiers |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4117031A (enExample) |
| JP (1) | JPS6020042B2 (enExample) |
| AR (1) | AR212082A1 (enExample) |
| AT (1) | AT346592B (enExample) |
| BR (1) | BR7506265A (enExample) |
| CA (1) | CA1067243A (enExample) |
| FR (1) | FR2286158A1 (enExample) |
| GB (1) | GB1500825A (enExample) |
| IT (1) | IT1042830B (enExample) |
| NL (1) | NL178329C (enExample) |
| SU (1) | SU649323A3 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847030A1 (de) * | 1978-10-28 | 1980-05-08 | Basf Ag | Verfahren zur herstellung von mischkondensationsprodukten auf basis von phenol- butyraldehyd-harzen und deren verwendung |
| US4402857A (en) * | 1979-10-26 | 1983-09-06 | Texaco, Inc. | Demulsifier for produced oil-in-water emulsions containing spent mud acids |
| DE3142955A1 (de) * | 1981-10-29 | 1983-05-11 | Hoechst Ag, 6230 Frankfurt | "neue grenzflaechenaktive verbindungen, verfahren zu ihrer herstellung und ihre verwendung" |
| DE3223692A1 (de) * | 1982-06-25 | 1983-12-29 | Hoechst Ag, 6230 Frankfurt | Stickstoff enthaltende erdoel-emulsionsspalter und ihre verwendung |
| DE3223691A1 (de) * | 1982-06-25 | 1983-12-29 | Hoechst Ag, 6230 Frankfurt | Modifizierte veretherte phenol-aldehyd-kondensationsprodukte und deren verwendung zum spalten von erdoelemulsionen |
| DE3617178A1 (de) * | 1986-05-22 | 1987-11-26 | Basf Ag | Polyether, erhaeltlich durch umsetzung von alkylolierten bis-(4-hydroxyphenyl)-methanen mit polyalkylenoxiden und deren verwendung als erdoelemulsionsspalter |
| DE3809067A1 (de) * | 1988-03-18 | 1989-09-28 | Hoechst Ag | Verfahren zum trennen von erdoelemulsionen vom typ wasser-in-oel |
| US5407585A (en) * | 1993-08-16 | 1995-04-18 | Exxon Chemical Patents Inc. | Method of demulsifying water-in-oil emulsions |
| US5609794A (en) | 1994-08-05 | 1997-03-11 | Exxon Chemical Patents, Inc. | Demulsifier for water-in-oil emulsions, and method of use |
| DE19916945C1 (de) | 1999-04-15 | 2000-10-05 | Clariant Gmbh | Aromatische Aldehydharze und ihre Verwendung als Emulsionsspalter |
| DE19916946C1 (de) | 1999-04-15 | 2000-07-27 | Clariant Gmbh | Aromatische Aldehydharze und ihre Verwendung als Emulsionsspalter |
| DE10057043B4 (de) * | 2000-11-17 | 2004-05-06 | Clariant Gmbh | Alkylphenolglyoxalharze und ihre Verwendung als Emulsionsspalter |
| DE10224275B4 (de) * | 2002-05-31 | 2007-08-02 | Clariant Produkte (Deutschland) Gmbh | Emulsionsspalter |
| US6736211B2 (en) | 2002-07-22 | 2004-05-18 | Oil Chem Technologies | Method of using alkylsulfonated phenol/aldehyde resins as adsorption reducing agents for chemical flooding |
| RU2359994C1 (ru) * | 2008-04-07 | 2009-06-27 | Государственное образовательное учреждение высшего профессионального образования "Тюменский государственный нефтегазовый университет" | Способ деэмульгирования нефти бинарным деэмульгатором |
| RU2383583C1 (ru) * | 2008-07-25 | 2010-03-10 | Наталья Юрьевна Башкирцева | Состав для обезвоживания, обессоливания и регулирования реологических свойств высоковязких нефтей и водонефтяных эмульсий |
| DE102009040495B4 (de) | 2009-09-08 | 2014-02-13 | Clariant International Ltd. | Alkoxylierte Thiacalixarene und deren Verwendung als Rohöl-Emulsionsspalter |
| US9340725B2 (en) * | 2011-08-19 | 2016-05-17 | Baker Hughes Incorporated | Use of a BTEX-free solvent to prepare stimulation and oilfield production additives |
| CN102653685A (zh) * | 2012-04-06 | 2012-09-05 | 西南石油大学 | 一种原油采出液用双季铵盐型破乳剂及其制备方法 |
| JP5858115B1 (ja) * | 2014-09-03 | 2016-02-10 | 栗田工業株式会社 | ｏ／ｗ型エマルションの油水分離方法及びｏ／ｗ型エマルション用油水分離剤 |
| CA3051179C (en) * | 2017-01-25 | 2021-09-28 | Dorf Ketal Chemicals (India) Private Limited | Demulsification additive composition, use thereof, and method of demulsification |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2574543A (en) * | 1949-11-28 | 1951-11-13 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2679485A (en) * | 1952-06-27 | 1954-05-25 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2679484A (en) * | 1952-06-27 | 1954-05-25 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2679488A (en) * | 1952-06-27 | 1954-05-25 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2679486A (en) * | 1952-06-27 | 1954-05-25 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2695888A (en) * | 1952-09-19 | 1954-11-30 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2695887A (en) * | 1952-09-19 | 1954-11-30 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2695889A (en) * | 1952-09-19 | 1954-11-30 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2674619A (en) * | 1953-10-19 | 1954-04-06 | Wyandotte Chemicals Corp | Polyoxyalkylene compounds |
| FR1252877A (fr) * | 1959-02-10 | 1961-02-03 | Norton Co | Feuille d'abrasif appliqué souple |
| US3042625A (en) * | 1960-10-28 | 1962-07-03 | Nalco Chemical Co | Processes for breaking petroleum emulsions |
| US3278637A (en) * | 1960-10-28 | 1966-10-11 | Nalco Chemical Co | Polyoxyalkylated alkyl phenol-formal-dehyde-alkylene polyamine resins |
| FR1289576A (fr) * | 1961-03-24 | 1962-04-06 | Union Carbide Corp | Nouvelles compositions de résines formées d'un polyéther et d'un composé phénolique résineux |
| US3297638A (en) * | 1963-04-30 | 1967-01-10 | Monsanto Co | Composition consisting of an admixture of a phenol-aldehyde resin, an alkyl phenol-ethylene oxide condensate and a polyoxypropylene-ethylene oxide reaction product |
| US4032514A (en) * | 1971-08-18 | 1977-06-28 | Petrolite Corporation | Oxyalkylated cyclic phenol-aldehyde resins and uses therefor |
| US3725349A (en) * | 1972-06-12 | 1973-04-03 | Dow Chemical Co | Phenol-formaldehyde adhesive resins containing poly(c{11 {14 c{11 alkyleneoxy)glycols |
-
1975
- 1975-09-19 NL NLAANVRAGE7511088,A patent/NL178329C/xx not_active IP Right Cessation
- 1975-09-22 US US05/615,462 patent/US4117031A/en not_active Expired - Lifetime
- 1975-09-23 JP JP50114358A patent/JPS6020042B2/ja not_active Expired
- 1975-09-24 AR AR260513A patent/AR212082A1/es active
- 1975-09-24 FR FR7529207A patent/FR2286158A1/fr active Granted
- 1975-09-24 AT AT733475A patent/AT346592B/de not_active IP Right Cessation
- 1975-09-24 GB GB39095/75A patent/GB1500825A/en not_active Expired
- 1975-09-24 IT IT27602/75A patent/IT1042830B/it active
- 1975-09-25 CA CA236,332A patent/CA1067243A/en not_active Expired
- 1975-09-26 SU SU752176640A patent/SU649323A3/ru active
- 1975-09-26 BR BR7506265A patent/BR7506265A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2286158A1 (fr) | 1976-04-23 |
| JPS5153503A (enExample) | 1976-05-12 |
| NL178329C (nl) | 1986-03-03 |
| SU649323A3 (ru) | 1979-02-25 |
| AT346592B (de) | 1978-11-10 |
| ATA733475A (de) | 1978-03-15 |
| AR212082A1 (es) | 1978-05-15 |
| NL178329B (nl) | 1985-10-01 |
| FR2286158B1 (enExample) | 1979-03-16 |
| JPS6020042B2 (ja) | 1985-05-20 |
| DE2445873B2 (de) | 1976-07-29 |
| DE2445873A1 (de) | 1976-04-08 |
| IT1042830B (it) | 1980-01-30 |
| GB1500825A (en) | 1978-02-15 |
| BR7506265A (pt) | 1977-04-19 |
| US4117031A (en) | 1978-09-26 |
| NL7511088A (nl) | 1976-03-30 |
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