GB2020289A - Phosphorus containing betaine derivatives - Google Patents
Phosphorus containing betaine derivativesInfo
- Publication number
- GB2020289A GB2020289A GB7915709A GB7915709A GB2020289A GB 2020289 A GB2020289 A GB 2020289A GB 7915709 A GB7915709 A GB 7915709A GB 7915709 A GB7915709 A GB 7915709A GB 2020289 A GB2020289 A GB 2020289A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxyalkyl
- alkyl
- image
- phosphorus containing
- betaine derivatives
- 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
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 title 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/65—Mixtures of anionic with cationic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/886—Ampholytes containing P
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/06—Ether- or thioether carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/90—Betaines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/92—Sulfobetaines ; Sulfitobetaines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
The compounds have the formula:- <IMAGE> or <IMAGE> in which A is O<(-)>, OM, or -O-Y-R<(+)>; B is O<-> or OM'; X<(-)> is an anion; z is 0-2 and only one of A and B is O<(-)>; R is a group of formula [R'CON(R<2>)-(CH2)n-N(R<3>)(R<4>)-]<(+)>- or <IMAGE> in which R<1> is C5-22 alkyl, alkenyl, alkoxy or hydroxyalkyl or up to C20 aryl or aralkyl; R<2> is H, alkyl, hydroxyalkyl, alkenyl, cycloalkyl or polyoxyalkylene; R<3> and R<4> are alkyl, hydroxyalkyl, carboxyalkyl, polyoxylalkylene or R<3> and R<4> form a heterocycle with the N atom; n is 2-12; Z is N, S or O; o is 0-3; p is 1-3 and o + p is 3-4; R<6> is C2-6 alkyl or hydroxyalkyl; Y is alkylene optionally substituted by alkoxy, or hydroxy or interrupted by up to 3 O atoms; M and M' are H, alkyl, hydroxyalkyl, cycloalkyl, aralkyl, aryl or a salt radical provided when either is an organic radical the other is H or a salt radical. The compounds are used as surfactants.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/902,121 US4181634A (en) | 1977-06-17 | 1978-05-05 | Mild cleansing compositions comprising an alkyleneoxylated bisquaternary ammonium compound and an anionic or amphoteric detergent such as a phosphobetaine |
US05/965,462 US4261911A (en) | 1978-11-30 | 1978-11-30 | Phosphitaines |
US05/965,461 US4215064A (en) | 1978-11-30 | 1978-11-30 | Phosphobetaines |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2020289A true GB2020289A (en) | 1979-11-14 |
GB2020289B GB2020289B (en) | 1983-01-12 |
Family
ID=27420590
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7915709A Expired GB2020289B (en) | 1978-05-05 | 1979-05-04 | Phosphorus containing betaine derivates |
Country Status (16)
Country | Link |
---|---|
AR (1) | AR228016A1 (en) |
AT (1) | AT376685B (en) |
AU (1) | AU528547B2 (en) |
BE (1) | BE876055A (en) |
BR (1) | BR7902725A (en) |
CH (1) | CH650001A5 (en) |
ES (1) | ES480266A1 (en) |
FR (1) | FR2424925B1 (en) |
GB (1) | GB2020289B (en) |
GR (1) | GR64909B (en) |
IE (1) | IE48107B1 (en) |
MX (1) | MX150948A (en) |
NL (1) | NL193247C (en) |
NZ (1) | NZ190363A (en) |
PH (1) | PH16742A (en) |
PT (1) | PT69574A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2461715A1 (en) * | 1979-07-23 | 1981-02-06 | Johnson & Johnson Baby Prod | Cationic tri:ester phosphate for hair-care - prepd. by reacting tert. amine with epi-bi:phosphate or quat. ammonium cpd. with phosphorus oxychloride |
GB2166443A (en) * | 1984-09-10 | 1986-05-08 | Johnson & Johnson Baby Prod | Process for the preparation of phosphate surfactants |
EP0312962A2 (en) * | 1987-10-21 | 1989-04-26 | Kao Corporation | Phosphoric acid ester, process for preparing the same, and detergent composition containing the same |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE792662A (en) * | 1971-12-13 | 1973-06-13 | Hoechst Ag | PHOSPHORUS COMPOUNDS WHICH ARE MIXED IONS |
CA1038766A (en) * | 1973-04-09 | 1978-09-19 | Robert J. Verdicchio | Amphoteric surface active agents |
CH597252A5 (en) * | 1973-04-14 | 1978-03-31 | Hoechst Ag | |
US3950417A (en) * | 1975-02-28 | 1976-04-13 | Johnson & Johnson | High-lathering non-irritating detergent compositions |
-
1979
- 1979-04-30 AR AR276345A patent/AR228016A1/en active
- 1979-05-03 MX MX177513A patent/MX150948A/en unknown
- 1979-05-03 NZ NZ190363A patent/NZ190363A/en unknown
- 1979-05-04 NL NL7903526A patent/NL193247C/en not_active IP Right Cessation
- 1979-05-04 CH CH4206/79A patent/CH650001A5/en not_active IP Right Cessation
- 1979-05-04 AT AT0335679A patent/AT376685B/en active
- 1979-05-04 BR BR7902725A patent/BR7902725A/en unknown
- 1979-05-04 BE BE0/195007A patent/BE876055A/en not_active IP Right Cessation
- 1979-05-04 ES ES480266A patent/ES480266A1/en not_active Expired
- 1979-05-04 GR GR59021A patent/GR64909B/en unknown
- 1979-05-04 PT PT69574A patent/PT69574A/en unknown
- 1979-05-04 GB GB7915709A patent/GB2020289B/en not_active Expired
- 1979-05-04 FR FR7911364A patent/FR2424925B1/en not_active Expired
- 1979-05-07 PH PH22510A patent/PH16742A/en unknown
- 1979-05-11 AU AU46933/79A patent/AU528547B2/en not_active Expired
- 1979-08-08 IE IE881/79A patent/IE48107B1/en not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2461715A1 (en) * | 1979-07-23 | 1981-02-06 | Johnson & Johnson Baby Prod | Cationic tri:ester phosphate for hair-care - prepd. by reacting tert. amine with epi-bi:phosphate or quat. ammonium cpd. with phosphorus oxychloride |
GB2166443A (en) * | 1984-09-10 | 1986-05-08 | Johnson & Johnson Baby Prod | Process for the preparation of phosphate surfactants |
EP0312962A2 (en) * | 1987-10-21 | 1989-04-26 | Kao Corporation | Phosphoric acid ester, process for preparing the same, and detergent composition containing the same |
EP0312962A3 (en) * | 1987-10-21 | 1990-10-10 | Kao Corporation | Phosphoric acid ester, process for preparing the same, and detergent composition containing the same |
US4985412A (en) * | 1987-10-21 | 1991-01-15 | Kao Corporation | Phosphoric acid ester, process for preparing the same, and detergent composition containing the same |
Also Published As
Publication number | Publication date |
---|---|
GB2020289B (en) | 1983-01-12 |
NL193247C (en) | 1999-04-02 |
ATA335679A (en) | 1984-05-15 |
IE790881L (en) | 1979-11-05 |
IE48107B1 (en) | 1984-10-03 |
ES480266A1 (en) | 1980-08-16 |
PT69574A (en) | 1979-06-01 |
MX150948A (en) | 1984-08-24 |
GR64909B (en) | 1980-06-07 |
AT376685B (en) | 1984-12-27 |
AU4693379A (en) | 1979-11-08 |
NZ190363A (en) | 1981-05-01 |
PH16742A (en) | 1984-02-10 |
AR228016A1 (en) | 1983-01-14 |
FR2424925A1 (en) | 1979-11-30 |
NL193247B (en) | 1998-12-01 |
NL7903526A (en) | 1979-11-07 |
CH650001A5 (en) | 1985-06-28 |
BE876055A (en) | 1979-11-05 |
FR2424925B1 (en) | 1988-05-20 |
AU528547B2 (en) | 1983-05-05 |
BR7902725A (en) | 1979-11-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PE20 | Patent expired after termination of 20 years |
Effective date: 19990503 |