GB1599414A - Shampoo with anti-grease properties - Google Patents
Shampoo with anti-grease properties Download PDFInfo
- Publication number
- GB1599414A GB1599414A GB1596977A GB1596977A GB1599414A GB 1599414 A GB1599414 A GB 1599414A GB 1596977 A GB1596977 A GB 1596977A GB 1596977 A GB1596977 A GB 1596977A GB 1599414 A GB1599414 A GB 1599414A
- Authority
- GB
- United Kingdom
- Prior art keywords
- shampoo
- fluorosurfactant
- weight
- hair
- detergent
- 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
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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
- A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
- A61K8/70—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- C11D1/004—Surface-active compounds containing F
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Cosmetics (AREA)
Description
(54) SHAMPOO WITH ANTI-GREASE PROPERTIES
(71) We, UNILEVER LIMITED, a Company organised under the laws of
Great Britain, of Unilever House, Blackfriars, London, EC4, England, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to a hair shampoo which inhibits the spread of grease on hair.
In the United States Patent No. 3,959,462 it is disclosed that a particular class of fluorine containing polymers which are cationic fluoroacrylate latices can be incorporated into shampoos in order to impart an anti-grease effect to hair. By an anti-grease effect is meant that sebum, the naturally oily secretion of the scalp, is prevented from spreading along the hair shaft and thus making the hair greasy. The production of sebum by the sebaceous gland is not thought to be particularly affected.
Our own experiences have shown that really pronounced anti-grease effects cannot be obtained from shampoos which contain emulsion fluor polymers.
Furthermore it was found difficult to formulate shampoos to contain polymers and they often suffered from stability problems.
It has now been found that it is possible to obtain anti-grease effects from a shampoo if the shampoo is made by using an anionic, ampholytic, nonionic or cationic non-polymeric fluorosurfactant as the active anti-grease agent.
The anti-grease effect of the detergent-active compounds and fluorosurfactants can be determined by a test involving measuring the contact angle to a-bromonaphthalene of hair washed in the shampoo. The test is based on the test which is described by A. K. Kurilenka and L. B. Aleksandrova in
Khimicheskie Volkna (1965), 3, 65-67 and is performed as follows:
A single hair is sandwiched between two microscope slides which are held together by screw clamps at either end. A drop of cr-bromonaphthalene is placed at one end of the slides and is spread between them by capillary attraction. A liquid film is formed between slides which contacts the hair to give two contact angles.
The angle which is required is the so-called "advancing" contact angle and this can be determined by screwing in the screw clamps so that the film is "squeezed" along the hair shaft. The advancing contact angle of the washed hair can then be measured under the microscope. An untreated hair shows an advancing contact angle of about 300.
The relation between the advancing contact angle and the anti-grease effects of the fluorosurfactants according to the invention are demonstrated by the following experiment, the results of which are shown in Table I.
Six Italian blue string hair switches each weighing 2 g and being 6 cm long and having been shampooed with 15% w/w aqueous monoethanolamine laurylsulphate were treated with solutions of (mono(2-(N-ethyl perfluoro octane sulphonamide)ethyl)phosphate of varying concentrations such that the switches had contact angles with ct;bromonaphthalene of 40 , 50 , 60 , 70" and 80". These switches were then placed in contact with a mass of cotton wool soaked in light mineral oil to simulate the situation on the greasy scalp. The switches were weighed after one and two weeks and the amount of oil taken up by them calculated. This is shown in the Table I below.
TABLE I
One week oil 2 weeks oil Contact angle uptake 10-3g uptake 10-3 g 300 1) 85.8 446.0 40 62.1 269.3 50 67.7 I75.5 60 30.7 48.2 70 35.0 50.5 800 29.0 48.7 " untreated hair.
This Table shows how the oil repellency of the switch increases as the contact angle increases. In particular it can be seen that after two weeks the amount of oil taken up by switches having a contact angle of 45 is only half of that taken up by switches of 30 . Hence a contact angle of 45G is taken as giving a good level of oil repellency but preferably a contact angle of at least 600 is sought.
The next Table II gives a picture of the advancing contact angles of hair treated with aqueous emulsions of some commercially available fluor polymers.
TABLE II
Advancing contact angles to a-bromonaphthalene.
Polymer Conc. % Contact angle FC 208t' 0.2 32 3.0 44 FC 210" 0.2 31 3.0 44 Zopel B2' 0.2 31 "Trade name of 3M (Minnesota Manufacturing and Mining Co.).
2'Trade name of Du Pont.
This Table shows that really pronounced anti-greasing effects cannot be obtained from these materials even in the absence of a hydrocarbon detergent.
The present invention now provides an aqueous shampoo for inhibiting the spread of grease on hair comprising an anionic, ampholytic or nonionic surfaceactive agent and a non-polymer fluorine-containing surfactant, chosen from the anionic, ampholytic, nonionic and cationic classes which provides the hair with an advancing contact angle to a-bromonaphthalene of at least 450, preferably at least 600.
The anionic, ampholytic nonionic or cationic non-polymer fluoro-surfactants used in the present invention have the general formula: [ RfhX)a] bY where
Rf is a monovalent, (per)fluorinated aliphatic group which is either a straight C6-C22 chain or a branched chain derived by oligomerisation of 4-6 molecules of tetrafluorethylene; X is polyvalene bonding group, for example H2-, -C2-, -O-C6H4-, -O-C6H4-SO2-NH-, -O-C6H4-SO2-NH(CH2)n- where n is 2 to 4, or
where R is H, CH3 or C2H5 and R' is HCH2)n, where n' is 0 to 4;
Y is -CO2H, -SO3H, -OPO(OH)2, -OPO(OH)(O)- or a salt thereof, N+(CZH5)2C2H4CO2,
-N+(CH3)3Q- where Q is I-, OH- or CH3SO-4, or QCH2CH2O)n"R2 where n" is 0--100 and R2 is H, OH, C1-C20 alkyl or a isO or 1; and
b is 1 except that when Y is -OPO(OH)(O)- b is 2; the ratio of the amount of detergent-active compound to fluorosurfactant being such that the shampoo provides the hair with a contact angle to c- bromonaphthalene of at least 450, preferably at least 600. The salt referred to may for example be a sodium, potassium, ammonium or amine salt.
The ratio of the weight of the detergent-active compound to the fluorosurfactant is desirably from 2000:1 to 1:1, preferably from 20:1 to 1:1.
(ii) RfY' (iii) RfR4Y'
(v) RfOArY' where
R3 is a C1-C4 alkyl group;
R4 is a C1-C4 alkylene group;
Y' is -CO2H, -SO3H or -OPO(OH)2 or a salt thereof; and
Ar is a mono- or di-nuclear aromatic residue, the shampoo providing the hair with a contact angle to n-bromonaphthalene of at least 600.
If cationic non-polymer fluorosurfactants are used as the active anti-grease agents then it is difficult to formulate effective anti-grease shampoos with either anionic or ampholytic detergent-active materials because cationic fluorosurfactants are often incompatible with anionic or ampholytic detergentactive material.
In these cases the use of solubilising agents or hydrotropes known to those well versed in the art can be used to overcome these incompatibility problems. On the other hand cationic non-polymeric fluorosurfactants can more easily be used together with nonionic detergent-active materials to give shampoos which are effective enough to fall within this invention:
As will by now be apparent, the essential components of the shampoo of the invention are (1) an anionic, ampholytic or nonionic detergent-active compound and (2) an anionic, ampholytic, cationic or nonionic non-polymer fluorosurfactant.
The term detergent-active compound as used in this specification does not include fluorosurfactants. Otherwise, any of the well-known anionic, ampholytic or nonionic detergent-active compounds which are suitable for incorporation in shampoos can be used. Typical of these anionic detergent-actives are the hydrocarbon surfactants such as the salts of long chain fatty acids (soaps), alkyl benzene sulphonates, alkyl sulphates and alkyl ether sulphates, especially the more water-soluble salts such as the sodium, ammonium, mono- and tri-ethanolamine salts. Typical of the ampholytic detergent-active compounds are alkyl cycloimidinium l-ethoxy-ethionic acid derivatives such as the compound sold under the Registered Trade Mark Miranol C2M. Typical of the nonionic detergent-active compounds are the nonylphenol ethyleneoxide condensates such as the compounds sold under the trade name of Ethylan B.V.
Other compounds such as alkanolamides, amine oxides and fatty acid betaines, can be used as lather improvers. Specific examples of alkanolamides which are useful in this context are coconut mono- and diethanolamides.
Preferably the anionic detergent-active compound will be present in an amount of from 10 to 15% by weight and the lather improver will be present in an amount of from 0.5 to 6% by weight.
The non-polymer fluorosurfactants which are preferred in the shampoos of this invention are compounds having the following formula:
(ii) (a) C8F17SO2K (b) C7Fg5CO . ONH4
where
X=NH4 or CF3(CF2)7CH2 . CH2-
(v) The "Monflor" range of anionic surfactants marketed by Imperial
Chemical Industries Ltd. with the formulae
where
Rf' is a radical derived by oligomerisation of tetrafluoroethylene, typically
Other ingredients can be incorporated into shampoos for their conventional purposes in conventional amounts. These include viscosity modifiers, perfumes, colourants, opacifying agents, clarifying agents and pH controllers, preservatives and anti-dandruff agents.
The invention will be further described by means of the following Examples.
Example I
The advancing contact angle to a-bromonaphthalene of a hair shaft was measured as described above. The hair had been treated with a shampoo containing monoethanolamine lauryl sulphate (MLS) of the concentration shown in column 1 of the Table III and containing a fluorsurfactant as shown in columns 2 and 4. The method of treatment is as follows:- A switch of degreased Virgin Italian blue string hair is combed, wetted and placed inside a polythene sleeve. The switch is rinsed several times by filling the sleeve with water and draining. 2 ml of shampoo per 10 g of hair is then placed on the switch using a syringe and the hair is then washed by mechanically manipulating the sleeve. The hair is then rinsed and left to drain and dried at 500 C.
TABLE III
Advancing Contact Angles to -Bromonaphthalene
Detergent Fluorosurfactant Anionic MLS (i) (b) (i) (a) Conc. Contact Conc. Contact Conc. % w/w %w/w angle %w/w angle 0.1 0 30O 0 30O 0.1 57O 0.1 63" 5.0 .0 30 0 30 0.1 43" 0.1 52" 1.0 47" 1.0 62" 5.0 81" 5.0 not measured 10.0 0 30 0 30 0.1 40 0.1 50 1.0 44" 1.0 60 2.0 51 2.0 71" 3.0 56" 3.0 71" 15.0 0 30 0 30 1.0 45" 1.0 55" 2.0 49" 2.0 66" 3.0 53" 3.0 70O 5.0 70" 5.0 not measured It can be seen from the above Table that for any given level of hydrocarbon surfactant the advancing contact angle using the two fluorosurfactants specified increases with increasing concentration of the fluorosurfactant and that as the concentration of hydrocarbon surfactant increases the concentrations of either of the fluorosurfactants must be increased to achieve the chosen contact angle of 45 degrees, which gives the minimum desired level of oil repellency and anti-grease effect.
Example II
As described in Example I, the advancing contact angles were determined after Virgin Italian hair was washed with prototype shampoos which contained 1% by weight of non-polymer fluorosurfactant (i)(a) and 100/0, by weight of various hydrocarbon surfactants at pH 7. The contact angles are given in the next Table IV.
TABLE IV
Detergent Contact angle Triethanolamine lauryl sulphate 54o Sodium lauryl ether sulphate (2EO) 48" Sodium lauryl sulphate 54o Ammonium lauryl sulphate 55o Diethanolamine lauryl sulphate 54" The Table shows that the anti-grease effect according to the invention can be achieved from a range of shampoos each containing .1% by weight of fluorosurfactant (i)(a) and one of various anionic hydrocarbon surfactants at a concentration of 10% by weight.
Example III
As described in Example I the advancing contact angles were determined after
Virgin Italian hair was washed with two prototype shampoos containing 1% by
weight non-polymer fluorosurfactant (iv), one containing 10% and the other 20% by
weight of N-dialkyl glycine and each having a pH of 7; the angles were respectively 49" and 45".
Example IV
As described in Example I, the advancing contact angles were determined
after Virgin Italian hair was washed with a prototype shampoo which contained 1%
by weight of non-polymeric fluorosurfactant (i)(a) and 10% by weight of a
nonylphenol ethylene oxide condensate Ethylan B.V. at pH 7; the contact angle
was found to be 47".
Example V
Virgin Italian hair was washed with a prototype shampoo, which contained 1%
by weight of the cationic fluorosurfactant (3-perfluoro octane sulfonamide-N
propyl) trimethylammonium iodide and 10% by weight a nonylphenolethylene
oxide condensate (Ethylan B.V.) at pH 7. The advancing contact angle determined
as described in Example I was found to be 46 .
Example VI
Virgin Italian hair was washed with a prototype shampoo, which contained 1%
by weight of a nonionic fluorosurfactant polyethylene glycolmono (2-(N
ethylperfluoro-octane sulfonamide)ethyl)ether (4 EO) and 10% by weight of MLS
at pH 7. The advancing contact angle determined as described in Example I was
found to be 460.
WHAT WE CLAIM IS:- 1. An aqueous hair shampoo comprising a water-soluble fluorine-free anionic,
ampholytic or nonionic detergent-active compound and an anionic, ampholytic,
nonionic or cationic non-polymer fluorosurfactant having the general formula: [Rf(X)a] b- where Rf is a monovalent, perfluorinated, aliphatic group which is either a straight C6-C22 chain or a branched chain derived by oligomerisation of 4--6 molecules of
tetrafluoroethylene;
X is a polyvalent bonding group;
Y is -CO2H, -SO3H, -OPO(OH)2, -OPO(OH)(O)- or a salt thereof, N+(C2H5)2C2H4CO-2,
-N+(CH3)3Q where Q is I-, OH- or CH3S0-4, or hCH2CH2O)n,R2 where n" is 0--100 and R2 is H, OH, C1-C20 alkyl or Rf;
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (13)
1. An aqueous hair shampoo comprising a water-soluble fluorine-free anionic,
ampholytic or nonionic detergent-active compound and an anionic, ampholytic,
nonionic or cationic non-polymer fluorosurfactant having the general formula: [Rf(X)a] b- where Rf is a monovalent, perfluorinated, aliphatic group which is either a straight C6-C22 chain or a branched chain derived by oligomerisation of 4--6 molecules of
tetrafluoroethylene;
X is a polyvalent bonding group;
Y is -CO2H, -SO3H, -OPO(OH)2, -OPO(OH)(O)- or a salt thereof, N+(C2H5)2C2H4CO-2,
-N+(CH3)3Q where Q is I-, OH- or CH3S0-4, or hCH2CH2O)n,R2 where n" is 0--100 and R2 is H, OH, C1-C20 alkyl or Rf;
a isO or 1; and
b is 1 except that when Y is -OPO(OH)(O)- b is 2; the ratio of the amount of detergent-active compound to fluorosurfactant being such that the shampoo provides the hair with a contact angle to a- bromonaphthalene of at least 45".
2. A shampoo as claimed in Claim 1, wherein X is -CH2-, C2H4-, -0- C6H4-, -O-C6H4-SO2-NH-, -O-C6H4-SO2-NH(CH2)n- where n is 2 to 4, or
where R is H, CH3 or C2H5 and R1 is -(CH2)n'-, where n' is 0 to 4.
3. A shampoo as claimed in Claim 1 comprising from 5 to 20% by weight of a water-soluble fluorine-free anionic or ampholytic detergent-active compound and wherein the fluorosurfactant has any of the following general formulae:-
(ii) RfY' (iii) RfR4Y'
(v) RfOArY' where
R3 is a C1-C4 alkyl group;
R4 is a C1-C4 alkylene group;
Y' is -CO2H, -SO3H or -OPO(OH)2 or a salt thereof; and
Ar is a mono- or di-nuclear aromatic residue, the shampoo providing the hair with a contact angle to cr-bromonaphthalene of at least 600.
4. A shampoo as claimed in Claim 3, wherein the fluorosurfactant has the formula
5. A shampoo as claimed in Claim 4, wherein the fluorosurfactant has the formula C8F,7SO2N(C2H5)CH2CH20PO(OH)2
6. A shampoo as claimed in Claim 3, wherein the fluorosurfactant has the formula
7. A shampoo as claimed in Claim 3, wherein the fluorosurfactant has the formula CFj(CF2)7CH2CH2OPO(ONH4)2
8. A shampoo as claimed in Claim 3, wherein the fluorosurfactant has the formula [CF3(CF2),CH2CH20]2PO(ONH4)
9. A shampoo as claimed in any of the preceding claims, wherein the anionic detergent-active compound is an alkyl sulphate.
10. A shampoo as claimed in Claim 9, wherein the alkyl sulphate is monoethanolamine lauryl sulphate.
11. A shampoo as claimed in any of the preceding claims, wherein the ratio of the weight of detergent active compound to fluorosurfactant is from 2000:1 to 1:1.
12. A shampoo as claimed in Claim 11, wherein the said ratio is 20:1 to 1:1.
13. A shampoo as claimed in Claim 1 comprising an anionic or ampholytic detergent-active compound and an anionic or ampholytic non-polymer fluorosurfactant substantially as hereinbefore described in any one of the
Examples.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1596977A GB1599414A (en) | 1977-04-18 | 1977-04-18 | Shampoo with anti-grease properties |
| CA301,254A CA1105837A (en) | 1977-04-18 | 1978-04-17 | Anti-grease shampoo containing fluorine-free surfactant and non-polymer fluorosurfactant |
| DE19782816828 DE2816828A1 (en) | 1977-04-18 | 1978-04-18 | ANTIFAT SHAMPOO |
| FR7811386A FR2387648A1 (en) | 1977-04-18 | 1978-04-18 | SHAMPOO WITH ANTI-GREASE PROPERTIES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1596977A GB1599414A (en) | 1977-04-18 | 1977-04-18 | Shampoo with anti-grease properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1599414A true GB1599414A (en) | 1981-09-30 |
Family
ID=10068846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1596977A Expired GB1599414A (en) | 1977-04-18 | 1977-04-18 | Shampoo with anti-grease properties |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1105837A (en) |
| DE (1) | DE2816828A1 (en) |
| FR (1) | FR2387648A1 (en) |
| GB (1) | GB1599414A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005095567A1 (en) * | 2004-03-03 | 2005-10-13 | 3M Innovative Properties Company | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| US11193059B2 (en) | 2016-12-13 | 2021-12-07 | Current Lighting Solutions, Llc | Processes for preparing color stable red-emitting phosphor particles having small particle size |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2450105A1 (en) * | 1979-02-27 | 1980-09-26 | Oreal | COMPOSITION AND METHOD FOR TREATING KERATINIC MATERIALS BASED ON FLUORINATED DERIVATIVES |
| ES2030494T3 (en) * | 1987-06-23 | 1992-11-01 | Eniricerche S.P.A. | COMPOSITION OF A PHASE CONTAINING A PERFLUORED OIL AND ONE OR SEVERAL SURFACE AGENTS, USEFUL AS AN EXCIPIENT FOR COSMETIC AND DERMATOLOGICAL FORMULATIONS, AS WELL AS FOR BIOMEDICINAL APPLICATIONS. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130594C (en) * | 1968-07-22 | |||
| GB1337467A (en) * | 1971-10-13 | 1973-11-14 | Dow Corning Ltd | Wetting compositions and treatment of surfaces therewith |
| US3993745A (en) * | 1974-05-31 | 1976-11-23 | Alberto Culver Company | Perfluorinated compounds in hair treatment compositions |
| US4013786A (en) * | 1974-05-31 | 1977-03-22 | Alberto Culver Company | Hair creme rinses and hair conditioners containing hydrophobic-lipophobic perfluorinated compounds |
| US3993744A (en) * | 1974-05-31 | 1976-11-23 | Alberto Culver Company | Live human hair treatment compositions containing perfluorinated compounds |
-
1977
- 1977-04-18 GB GB1596977A patent/GB1599414A/en not_active Expired
-
1978
- 1978-04-17 CA CA301,254A patent/CA1105837A/en not_active Expired
- 1978-04-18 FR FR7811386A patent/FR2387648A1/en active Pending
- 1978-04-18 DE DE19782816828 patent/DE2816828A1/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005095567A1 (en) * | 2004-03-03 | 2005-10-13 | 3M Innovative Properties Company | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| US7294610B2 (en) | 2004-03-03 | 2007-11-13 | 3M Innovative Properties Company | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| CN1926227B (en) * | 2004-03-03 | 2010-06-23 | 3M创新有限公司 | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| US7811978B2 (en) | 2004-03-03 | 2010-10-12 | 3M Innovative Properties Company | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| US7985723B2 (en) | 2004-03-03 | 2011-07-26 | 3M Innovative Properties Company | Fluorinated sulfonamide surfactants for aqueous cleaning solutions |
| US11193059B2 (en) | 2016-12-13 | 2021-12-07 | Current Lighting Solutions, Llc | Processes for preparing color stable red-emitting phosphor particles having small particle size |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1105837A (en) | 1981-07-28 |
| DE2816828A1 (en) | 1978-10-19 |
| FR2387648A1 (en) | 1978-11-17 |
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| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |