GB1594002A - 2-amino-1,3-benzthiazole-5-sulphonic acid - Google Patents
2-amino-1,3-benzthiazole-5-sulphonic acid Download PDFInfo
- Publication number
- GB1594002A GB1594002A GB15281/77A GB1528177A GB1594002A GB 1594002 A GB1594002 A GB 1594002A GB 15281/77 A GB15281/77 A GB 15281/77A GB 1528177 A GB1528177 A GB 1528177A GB 1594002 A GB1594002 A GB 1594002A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- sulphonic acid
- amino
- benzthiazole
- mixture
- 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
- HHPNZYLFEYNOHR-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2SC(N)=NC2=C1 HHPNZYLFEYNOHR-UHFFFAOYSA-N 0.000 title claims abstract description 16
- LQFGLIVRXSQIDU-UHFFFAOYSA-N 3-nitro-4-thiocyanatobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(SC#N)C([N+]([O-])=O)=C1 LQFGLIVRXSQIDU-UHFFFAOYSA-N 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- -1 3-nitro-4-thiocyanobenzene sulphonic acid sodium salt Chemical compound 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 5
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 3
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 235000010288 sodium nitrite Nutrition 0.000 claims description 3
- SXTOGAIYFMTUAD-UHFFFAOYSA-M sodium;4-amino-3-nitrobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1[N+]([O-])=O SXTOGAIYFMTUAD-UHFFFAOYSA-M 0.000 claims description 3
- 239000001117 sulphuric acid Substances 0.000 claims description 3
- 235000011149 sulphuric acid Nutrition 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000012267 brine Substances 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 2
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- IXJHMTJVCWFNGB-UHFFFAOYSA-N 3-amino-4-thiocyanatobenzenesulfonic acid Chemical compound NC=1C=C(C=CC1SC#N)S(=O)(=O)O IXJHMTJVCWFNGB-UHFFFAOYSA-N 0.000 description 1
- AKTKBYZZTJZZPY-UHFFFAOYSA-N 4-amino-1,3-benzothiazole-2-sulfonic acid Chemical compound NC1=CC=CC2=C1N=C(S(O)(=O)=O)S2 AKTKBYZZTJZZPY-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Coloring (AREA)
Abstract
2-Amino-1,3-benzothiazole-5-sulphonic acid can be used as a new diazo component in the synthesis of azo dyes. The new compound can be prepared by reducing 3-nitro-4-thiocyanobenzenesulphonic acid.
Description
(54) 2-AMINO-i ,3-BENZTHIAZOLE-5-SULPHONIC ACID
(71) We, IMPERIAL CHEMICAL INDUSTRIES LIMITED, Imperial Chemical House,
Millbank, London SW1P 3JF, a British Company 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:
According to the invention there is provided 2-amino-1,3-benzthiazole-5-sulphonic acid which has the structure:
and which may be prepared by the reduction of 3-nitro-4-thiocyanobenzene sulphonic acid. A method known per se may be used for the reduction. Thus, the nitro compound may be hydrogenated over a catalyst, for example a nickel or palladium on charcoal catalyst or an iron/acid reduction may be used. Other suitable methods, already known for the reduction of aromatic nitro compounds to aromatic amines, include electrolytic reduction. It is believed that the 3-amino-4-thiocyanobenzene sulphonic acid is first formed and then cyclises spontaneously to the amino-benzthiazole sulphonic acid.
The 3-nitro-4-thiocyanobenzene sulphuric acid may itself be prepared by a Sandmeyer reaction, that is to say by reacting diazotised 4-amino-3-nitrobenzene sulphonic acid with thiocyanate ions in the presence of cuprous ions.
A particularly convenient method of preparing the 2-amino-1,3-benzthiazole-5-sulphonic acid is to carry out the aforesaid Sandmeyer reaction on the 4-amino-3-nitrobenzene sulphonic acid and then reduce the reaction product without isolating the 3-nitro-4-thiocyanobenzene sulphonic acid. The overall yield using this method is approximately 90% of the theoretical yield.
If desired, the 2-amino-i,3-benzthiazole-5-sulphonic acid may be isolated in the form of one of its salts, for example an alkali metal or ammonium salt.
The new acid (or a salt thereof) may be used as a diazo component in the manufacture of azo dyes. Such dyes may be manufactured by coupling the diazotised 2-amino-i ,3-benzthiazole-5- sulphonic acid with a coupling component of the pyrazolone, aminopyrazole, 2,6dihydroxypyridine, 2,6-diaminopyridine, indole or arylamine series and may be used as acid dyes for the colouration of polyamide textile materials. It has the advantage over isomeric compounds, such as 2-amino-i ,3-benzthiazole-6-sulphonic acid, that it can be prepared in good yield from readily available intermediates by relatively simple aqueous processes.
The invention is illustrated but not limited by the following Examples in which all parts and percentages are by weight.
Example 1
24 parts of 4-amino-3-nitrobenzene sulphonic acid sodium salt are dissolved in 125 parts of 1 molar sulphuric acid with stirring and the solution is cooled to 0 C and diazotised by the slow addition of 50 parts of 2 molar sodium nitrite solution. 15 parts of sodium acetate are then added and the mixture is added to a stirred solution of 15.2 parts of ammonium thiocyanate and 0.5 parts of cuprous thiocyanate dissolved in 200 parts of water. After 2 hrs, the evolution of nitrogen has ceased and no diazonium salt can be detected in the mixture. 40 parts of sodium chloride are added and, after stirring a further 10 minutes, the crystalline precipitate is collected by filtration, washed with a little 10% brine and dried. The yield of 3-nitro-4-thiocyanobenzene sulphonic acid sodium salt is 26.5 parts. An infra red spectrum of the product shows a characteristic thiocyano absorption peak at 2170 cm".
5.64 parts of the 3-nitro-4-thiocyanobenzene sulphonic acid are dissolved in 100 parts of water and the solution is hydrogenated at room temperature and 1 atmosphere pressure of hydrogen over 0.5 part of a 5%palladium on charcoal catalyst. When the theoretical volume of 1.34 litres of hydrogen has been absorbed, the solution is separated from the catalyst and acidified by the addition of hydrochloric acid. The white precipitate is collected by filtration washed with water and dried at 1200C in air. 4.6 parts of 2-amino-1,3-benzthiazole-5-sulphonic acid are obtained.
Elementary analysis of the product gives the following composition:
Carbon - 36.5%, Hydrogen 2.4%, Nitrogen 12.1% H6N2O3S2 requires:- Carbon 36.52%, Hydrogen 2.60%, Nitrogen 12.17%
Example 2
A mixture of 25 parts of iron filings, 100 parts of water and 0.5 parts of 36% hydrochloric acid is stirred for 30 minutes at a temperature of 95"C. 14.1 parts of 3-nitro-4-thiocyanobenzene sulphonic acid are then added and vigorous stirring at 90-95"C continued for a further 2 hours.
The mixture is then made alkaline by the addition of 2 parts of sodium carbonate and filtered.
The clear filtrates are acidified by the addition of hydrochloric acid and the precipitate which separates is collected by filtration, washed with water and dried at 1200C. 10.35 parts of 2-amino-1,3-benzthiazole-5-sulphonic acid are thus obtained.
Example 3
24 parts of 4-amino-3-nitrobenzene sulphonic acid sodium salt are dissolved in 125 parts of 1 molar sulphuric acid with stirring and the solution is cooled to 0 C and diazotised by the slow addition of 50 parts of 2 molar sodium nitrite solution. 15 parts of sodium acetate are then added and the mixture is added to a stirred solution of 15.2 parts of ammonium thiocyanate and 0.5 part of cuprous thiocyanate dissolved in 200 parts of water. After 2 hours the evolution of nitrogen has ceased and no diazonium salt can be detected in the reaction mixture. The whole mixture is then added to a mixture of 50 parts of iron filings, 100 parts of water and 1 part of 36% hydrochloric acid, which has previously been stirred and heated at 95"C for a period of 30 minutes, and stirring at 90-95"C is continued for 2 hours. The mixture is then made alkaline by the addition of 4 parts of sodium carbonate and filtered. The clear filtrates are acidified by the addition of hydrochloric acid and the precipitate thus formed is collected by filtration, washed with water and dried at 1200C. 21 parts of 2-amino-1,3-benzthiazole-5-sulphonic acid are thus obtained.
WHAT WE CLAIM IS
1. 2-Amino-1,3-benzthiazole-5-sulphonic acid.
2. A process for the preparation of 2-amino-1,3-benzthiazole-5-sulphonic acid which comprises reducing 3-nitro-4-thiocyanobenzene sulphonic acid by a known reduction method.
3. A process as claimed in claim 2 wherein the 3-nitro-4-thiocyanobenzene sulphonic acid is obtained by reacting diazotised 4-amino-3-nitrobenzene sulphonic acid with thiocyanate ions in the presence of cuprous ions and is reduced without being isolated.
4. A process as claimed in claim 2 conducted substantially as hereinbefore described with reference to Example 1 or Example 2.
5. A process as claimed in claim 3 conducted substantially as hereinbefore described with
reference to Example 3.
6. 2-Amino-1,3-benzthiazole-5-sulphonic acid whenever prepared by a process claimed in
any one of claims 2 to 5.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (6)
1. 2-Amino-1,3-benzthiazole-5-sulphonic acid.
2. A process for the preparation of 2-amino-1,3-benzthiazole-5-sulphonic acid which comprises reducing 3-nitro-4-thiocyanobenzene sulphonic acid by a known reduction method.
3. A process as claimed in claim 2 wherein the 3-nitro-4-thiocyanobenzene sulphonic acid is obtained by reacting diazotised 4-amino-3-nitrobenzene sulphonic acid with thiocyanate ions in the presence of cuprous ions and is reduced without being isolated.
4. A process as claimed in claim 2 conducted substantially as hereinbefore described with reference to Example 1 or Example 2.
5. A process as claimed in claim 3 conducted substantially as hereinbefore described with
reference to Example 3.
6. 2-Amino-1,3-benzthiazole-5-sulphonic acid whenever prepared by a process claimed in
any one of claims 2 to 5.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15281/77A GB1594002A (en) | 1977-04-13 | 1977-04-13 | 2-amino-1,3-benzthiazole-5-sulphonic acid |
| FR7809142A FR2387225A1 (en) | 1977-04-13 | 1978-03-29 | 2-AMINO 1,3-BENZOTHIAZOLE-5-SULPHONIC ACID |
| DE19782813983 DE2813983A1 (en) | 1977-04-13 | 1978-03-31 | BENZTHIAZOLSULPHONIC ACID AND METHOD FOR PRODUCING IT |
| BE186597A BE865725A (en) | 1977-04-13 | 1978-04-05 | NEW HETEROCYCLIC ACID |
| IT22230/78A IT1158682B (en) | 1977-04-13 | 1978-04-12 | PROCEDURE FOR THE PREPARATION OF 2-AMINO-1,3-BENZOTIALZOL-5-SULPHONIC ACID |
| CH393378A CH638506A5 (en) | 1977-04-13 | 1978-04-12 | Benzothiazolesulphonic acid and preparation thereof |
| JP4308878A JPS53127468A (en) | 1977-04-13 | 1978-04-12 | 22aminoo1*33zenzothiazolee55 sulfonate and process for preparing same |
| ES468771A ES468771A1 (en) | 1977-04-13 | 1978-04-13 | 2-amino-1,3-benzthiazole-5-sulphonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15281/77A GB1594002A (en) | 1977-04-13 | 1977-04-13 | 2-amino-1,3-benzthiazole-5-sulphonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1594002A true GB1594002A (en) | 1981-07-30 |
Family
ID=10056288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15281/77A Expired GB1594002A (en) | 1977-04-13 | 1977-04-13 | 2-amino-1,3-benzthiazole-5-sulphonic acid |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS53127468A (en) |
| BE (1) | BE865725A (en) |
| CH (1) | CH638506A5 (en) |
| DE (1) | DE2813983A1 (en) |
| ES (1) | ES468771A1 (en) |
| FR (1) | FR2387225A1 (en) |
| GB (1) | GB1594002A (en) |
| IT (1) | IT1158682B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7416593B2 (en) | 2002-11-13 | 2008-08-26 | Clariant Finance (Bvi) Limited | Mono azo dyes |
-
1977
- 1977-04-13 GB GB15281/77A patent/GB1594002A/en not_active Expired
-
1978
- 1978-03-29 FR FR7809142A patent/FR2387225A1/en active Granted
- 1978-03-31 DE DE19782813983 patent/DE2813983A1/en not_active Withdrawn
- 1978-04-05 BE BE186597A patent/BE865725A/en not_active IP Right Cessation
- 1978-04-12 IT IT22230/78A patent/IT1158682B/en active
- 1978-04-12 JP JP4308878A patent/JPS53127468A/en active Pending
- 1978-04-12 CH CH393378A patent/CH638506A5/en not_active IP Right Cessation
- 1978-04-13 ES ES468771A patent/ES468771A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7416593B2 (en) | 2002-11-13 | 2008-08-26 | Clariant Finance (Bvi) Limited | Mono azo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7822230A0 (en) | 1978-04-12 |
| FR2387225B3 (en) | 1980-11-21 |
| BE865725A (en) | 1978-10-05 |
| ES468771A1 (en) | 1978-11-16 |
| CH638506A5 (en) | 1983-09-30 |
| DE2813983A1 (en) | 1978-10-26 |
| IT1158682B (en) | 1987-02-25 |
| FR2387225A1 (en) | 1978-11-10 |
| JPS53127468A (en) | 1978-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960310 |