GB1600787A - Process for dyeing or printing fibre materials with azo dyestuffs produced on the fibre - Google Patents
Process for dyeing or printing fibre materials with azo dyestuffs produced on the fibre Download PDFInfo
- Publication number
- GB1600787A GB1600787A GB10987/78A GB1098778A GB1600787A GB 1600787 A GB1600787 A GB 1600787A GB 10987/78 A GB10987/78 A GB 10987/78A GB 1098778 A GB1098778 A GB 1098778A GB 1600787 A GB1600787 A GB 1600787A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- acid
- fibre
- effected
- reactive
- 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
- 238000000034 method Methods 0.000 title claims description 40
- 230000008569 process Effects 0.000 title claims description 39
- 239000000463 material Substances 0.000 title claims description 17
- 239000000835 fiber Substances 0.000 title claims description 13
- 238000004043 dyeing Methods 0.000 title claims description 12
- 230000008878 coupling Effects 0.000 claims description 22
- 238000010168 coupling process Methods 0.000 claims description 22
- 238000005859 coupling reaction Methods 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 20
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- -1 chloropropionyl groups Chemical group 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 9
- 238000010025 steaming Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000006149 azo coupling reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000003381 solubilizing effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- YZOXPLQWARQVEJ-UHFFFAOYSA-N 2-methylsulfonyl-1,3-benzothiazole Chemical group C1=CC=C2SC(S(=O)(=O)C)=NC2=C1 YZOXPLQWARQVEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- ANOHEAFDYMLBDM-UHFFFAOYSA-N azane;triazine Chemical group N.C1=CN=NN=C1 ANOHEAFDYMLBDM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 claims description 2
- 235000019233 fast yellow AB Nutrition 0.000 claims description 2
- 239000002985 plastic film Substances 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000007853 buffer solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/68—Preparing azo dyes on the material
Description
(54) PROCESS FOR DYEING OR PRINTING FIBRE
MATERIALS WITH AZO DYESTUFFS PRODUCED
ON THE FIBRE
(71) We, HOECHST AKTIEN
GESELLSCHAFT, a body corporate organised according to the laws of the Federal
Republic of Germany, of 6230 Frankfurt (Main) 80, Postfach 80 03 20, Federal
Republic of Germany, 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:- The present invention relates to a process for dyeing or printing fibre materials and represents an improvement in or modification of the invention described in the specification of our copending patent application No. 3895/77 (Serial No.
1576061).
The specification of our copending patent application No. 3895/77 (Serial No.
1576061) describes and claims a process for dyeing or printing a fibre material comprising fibres having hydrogen atoms which are reactive under alkaline conditions, which comprises applying to the material, by one or more aqueous liquors or printing pastes, a water-soluble diazotizable primary aromatic or heterocyclic amine which is or becomes fibre-reactive under alkaline fixation conditions, an azo coupling component, an alkaline agent and sodium nitrite, fixing the amine to the fibres, and subsequently treating the material with an acid to effect development of the dyestuff.
The coupling component and the amine may be applied separately or together.
The present invention provides a modification of the process of our abovementioned copending application, which comprises the use, when applying the coupling component and the amine separately, of an azo coupling component which is or becomes fibre-reactive under alkaline fixation conditions.
Suitable amines for the process of the invention are all aromatic or heterocyclic primary amines which have in the molecule a fibre-reactive group and which are watersoluble. The water-solubility may be caused either by the fibre-reactive group itself, or by one or more other water-solubilizing groups in the molecule, especially sulfonic acid groups.
Thus, primary aromatic carbocyclic or heterocyclic amines are concerned which contains at least one group or substituent capable of reacting with fibers containing reactive hydrogen atoms, such as cellulose fibres. Reactive groups are, for example, epoxy groups, the ethylene imide group, the vinyl group within the vinylsulfonic acid ester or the acrylic acid ester radical, moreover preliminary stages that form such reactive groups in an alkaline medium, the p - thiosulfatoethylsulfonyl group, the B - sulfato - ethylsulfonyl group, the ,B chloroethylsulfonyl group and the ,B- phosphatoethylsulfonyl group.It is not important whether these radicals are bound to the amine directly or through an intermediate link, especially -NH-, -NR- (R=alkyl having 1 to 3 carbon atoms), an alkylene group having 1 to 3 carbon atoms or a combination of such intermediate links, such as in the case of the ethionyl-amino radical.
Reactive substituents in fibre-reactive amines are those which may be split off easily and leave an electrophilic radical, such as halogen atoms at the following ring systems: quinoxaline, triazine, pyrimidine, phthalazine and pyridazone. There may also be used amines the reactive radical of which represents a fi - (2,2,3,3 - tetrafluoro cyclo - butyl) - acryloylamino group or a A - (2,2,3,3 - tetrafluoro - 4 - alkylcyclo - butyl)- acryloylamino - group, the alkyl group in the 4-position in the latter case having 1 to 4 carbon atoms.
The fibre, reactive group may be blocked, for example by reaction with methyl taurine.
The blocking may be reversed by usual processing methods.
Suitable coupling components for the process of the invention are all coupling components that contain fibre-reactive groups as indicated above, for example halogentriazine groups, halogenpyrimidine groups, halogen-quinoxaline carbonyl groups, halogenphthalazine carbonyl groups, vinylsulfone groups, p-hydroxyethylsulfone ester groups, methylsulfonyl benzthiazole groups, fluorobenzthiazole groups, ss - hydroxyethyl sulfonamide ester groups, - hydroxyethyl sulfonalkylamino ester groups, fi - bromoacryloyl groups, P chloropropionyl groups, ,B- - chloroacetyl groups, fi - phenylsulfonyl propionyl groups, halogenpyridazonalkyl groups, 2 chlorobenz - thlazol - sulfonyl groups, alkylsulfonyl groups, pyrimidine groups, ammonium triazine groups and acryloyl groups.
For the process of the invention there may also be used advantageously reactive coupling components, the water-solubility of which does not stem exclusively from the solubilizing action of the reactive group, but which contain in the molecule one or more further groups providing water-solubility, such as sulfonic acid groups or carboxylic acid groups. The improved degree of watersolubility is an appreciable feature insofar that padding liquors require much higher concentrations than those required for batchwise exhaustion liquors.
The process of the invention may be carried out in a manner wherein firstly the coupling component is applied and subsequently, if desired after an intermediate rinsing, the amine, alkali and sodium nitrite are applied.
Fixation of the fibre-reactive amine and coupling component is generally effected by dwelling at room temperature, drying or steaming. Dyestuff development is preferably effected by treatment with a dilute acid or acid mixture, for example a mixture of hydrochloric acid and acetic acid, or an acidic buffer mixture. It may alternatively be effected by steaming in an acidic atmosphere. The liquor or printing paste may additionally contain an agent which splits off an acid when heated, and then diazotization and coupling may be effected by dry heating or steaming.
Further relevant details about the process of the invention will be found in the specification of the parent application No.
3895/77 (Serial No. 1576061), the disclosure of which is incorporated by reference herein.
The dyeings and prints produced by the process of the invention have advantageous fastness to solvents.
The following Example illustrates the invention:
Example
A bleached mercerized cotton fabric was padded with a liquor containing, per liter,
20 g of the compound having the formula
20 g of calcinated soda and 100 g of urea.
Subsequently the textile material was dried at 1400C for 3 minutes, and then padded again with a liquor containing, per litre, 16 g of the compound having the formula
20 ml of sodium hydroxide solution (32.5 strength) and 20 g of sodium nitrite.
The thus padded fabric was rolled up and wrapped in a plastic sheet, where it was allowed to stand at room temperature overnight. For developing the dyeing, the fabric was padded the following day, with a liquor uptake of 100%, with a liquor containing 33 mV1 of hydrochloric acid (32.1% strength), 50 ml/l of acetic acid (60% strength) and 20 g/l of sodium acetate.
This operation was followed by an air passage of 60 seconds and a passage through hot water (700 C), rinsing, soaping, and further rinsing.
A clear and fast yellow dyeing was obtained.
WHAT WE CLAIM IS:
1. A process for dyeing or printing a fibre material comprising fibres having hydrogen atoms which are reactive under alkaline conditions, which comprises applying to the material by two or more treatments, each with an aqueous liquor or a printing paste, a water-soluble diazotizable primary aromatic or heterocyclic amine which is or becomes fibre-reactive under alkaline fixation conditions, an azo coupling component which is or becomes fibre-reactive under alkaline fixation conditions, an alkaline agent and sodium nitrite, the amine and the coupling component being applied separately, fixing the amine and the coupling component to the fibres, and subsequently treating the material with an acid to effect development of the dyestuff.
2. A process as claimed in claim 1, wherein the amine contains a reactive group
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (1)
- **WARNING** start of CLMS field may overlap end of DESC **.Suitable coupling components for the process of the invention are all coupling components that contain fibre-reactive groups as indicated above, for example halogentriazine groups, halogenpyrimidine groups, halogen-quinoxaline carbonyl groups, halogenphthalazine carbonyl groups, vinylsulfone groups, p-hydroxyethylsulfone ester groups, methylsulfonyl benzthiazole groups, fluorobenzthiazole groups, ss - hydroxyethyl sulfonamide ester groups, - hydroxyethyl sulfonalkylamino ester groups, fi - bromoacryloyl groups, P chloropropionyl groups, ,B- - chloroacetyl groups, fi - phenylsulfonyl propionyl groups, halogenpyridazonalkyl groups, 2 chlorobenz - thlazol - sulfonyl groups, alkylsulfonyl groups, pyrimidine groups, ammonium triazine groups and acryloyl groups.For the process of the invention there may also be used advantageously reactive coupling components, the water-solubility of which does not stem exclusively from the solubilizing action of the reactive group, but which contain in the molecule one or more further groups providing water-solubility, such as sulfonic acid groups or carboxylic acid groups. The improved degree of watersolubility is an appreciable feature insofar that padding liquors require much higher concentrations than those required for batchwise exhaustion liquors.The process of the invention may be carried out in a manner wherein firstly the coupling component is applied and subsequently, if desired after an intermediate rinsing, the amine, alkali and sodium nitrite are applied.Fixation of the fibre-reactive amine and coupling component is generally effected by dwelling at room temperature, drying or steaming. Dyestuff development is preferably effected by treatment with a dilute acid or acid mixture, for example a mixture of hydrochloric acid and acetic acid, or an acidic buffer mixture. It may alternatively be effected by steaming in an acidic atmosphere. The liquor or printing paste may additionally contain an agent which splits off an acid when heated, and then diazotization and coupling may be effected by dry heating or steaming.Further relevant details about the process of the invention will be found in the specification of the parent application No.3895/77 (Serial No. 1576061), the disclosure of which is incorporated by reference herein.The dyeings and prints produced by the process of the invention have advantageous fastness to solvents.The following Example illustrates the invention: Example A bleached mercerized cotton fabric was padded with a liquor containing, per liter, 20 g of the compound having the formula20 g of calcinated soda and 100 g of urea.Subsequently the textile material was dried at 1400C for 3 minutes, and then padded again with a liquor containing, per litre, 16 g of the compound having the formula20 ml of sodium hydroxide solution (32.5 strength) and 20 g of sodium nitrite.The thus padded fabric was rolled up and wrapped in a plastic sheet, where it was allowed to stand at room temperature overnight. For developing the dyeing, the fabric was padded the following day, with a liquor uptake of 100%, with a liquor containing 33 mV1 of hydrochloric acid (32.1% strength), 50 ml/l of acetic acid (60% strength) and 20 g/l of sodium acetate.This operation was followed by an air passage of 60 seconds and a passage through hot water (700 C), rinsing, soaping, and further rinsing.A clear and fast yellow dyeing was obtained.WHAT WE CLAIM IS: 1. A process for dyeing or printing a fibre material comprising fibres having hydrogen atoms which are reactive under alkaline conditions, which comprises applying to the material by two or more treatments, each with an aqueous liquor or a printing paste, a water-soluble diazotizable primary aromatic or heterocyclic amine which is or becomes fibre-reactive under alkaline fixation conditions, an azo coupling component which is or becomes fibre-reactive under alkaline fixation conditions, an alkaline agent and sodium nitrite, the amine and the coupling component being applied separately, fixing the amine and the coupling component to the fibres, and subsequently treating the material with an acid to effect development of the dyestuff.2. A process as claimed in claim 1, wherein the amine contains a reactive groupor substituent specifically mentioned herein.3. A process as claimed in claim 1 or claim 2, wherein the amine contains one or more non - fibre - reactive watersolubilizing groups.4. A process as claimed in claim 3, wherein the amine contains one or more sulfonic acid groups.5. A process as claimed in any one of claims I to 4, wherein the coupling component contains a reactive group specifically mentioned herein.6. A process as claimed in any one of claims 1 to 5, wherein the coupling component contains one or more non fibre - reactive water solubilizing groups.7. A process as claimed in claim 6, wherein the coupling component contains one or more sulfonic acid groups and/or one or more carboxylic acid groups.8. A process as claimed in any one of claims 1 to 7, wherein firstly the coupling components is applied and subsequently, if desired after an intermediate rinsing, the amine, alkali and sodium nitrite are applied.9. A process as claimed in any one of claims 1 to 8, wherein fixation is effected by dwelling at room temperature.10. A process as claimed in any one of claims I to 8, wherein fixation is effected by drying.11. A process as claimed in any one of claims 1 to 8, wherein fixation is effected by steaming.12. A process as claimed in any one of claims 1 to 11, wherein the dyestuff development is effected by treatment with a dilute acid or acid mixture.13. A process as claimed in any one of claims 1 to 11, wherein the dyestuff development is effected by treatment with an acid buffer mixture.14. A process as claimed in any one of claims 1 to 11, wherein the dyestuff development is effected by steaming in an acid atmosphere.15. A process as claimed in any one of claims 1 to 11, wherein a liquor or printing paste additionally contains an agent which splits off an acid when heated and the dyestuff development is effected by dry heating or steaming.16. A process as claimed in any one of claims 1 to 15, wherein an aqueous liquor is applied to the material by a padding process.17. A process as claimed in any one of claims 1 to 16, wherein a material comprising cellulosic fibres is dyed or printed.18. A process as claimed in claim 1, conducted substantially as described herein.19. A process as claimed in claim 1, conducted substantially as described in the Example.20. A fibre material comprising fibres having hydrogen atoms which are reactive under alkaline conditions, whenever dyed or printed by a process as claimed in any, one of claims 1 to 19.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2712087A DE2712087C3 (en) | 1977-03-19 | 1977-03-19 | Process for coloring or printing fiber materials with reactive hydrogen atoms with azo dyes produced on the fiber !! |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1600787A true GB1600787A (en) | 1981-10-21 |
Family
ID=6004069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10987/78A Expired GB1600787A (en) | 1977-03-19 | 1978-03-20 | Process for dyeing or printing fibre materials with azo dyestuffs produced on the fibre |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE865092R (en) |
| DE (1) | DE2712087C3 (en) |
| FR (1) | FR2384059A2 (en) |
| GB (1) | GB1600787A (en) |
| IT (1) | IT1113114B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19600633A1 (en) * | 1996-01-10 | 1997-07-17 | Dystar Textilfarben Gmbh & Co | Process for the production of colored native or synthetic substrates |
| DE19600634A1 (en) * | 1996-01-10 | 1997-07-17 | Dystar Textilfarben Gmbh & Co | Process for the production of colored native or synthetic substrates and their aftertreatment |
-
1977
- 1977-03-19 DE DE2712087A patent/DE2712087C3/en not_active Expired
-
1978
- 1978-03-17 IT IT21341/78A patent/IT1113114B/en active
- 1978-03-20 BE BE186096A patent/BE865092R/en active
- 1978-03-20 GB GB10987/78A patent/GB1600787A/en not_active Expired
- 1978-03-20 FR FR7807958A patent/FR2384059A2/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1113114B (en) | 1986-01-20 |
| IT7821341A0 (en) | 1978-03-17 |
| FR2384059A2 (en) | 1978-10-13 |
| DE2712087A1 (en) | 1978-09-21 |
| BE865092R (en) | 1978-09-20 |
| DE2712087C3 (en) | 1980-02-14 |
| DE2712087B2 (en) | 1979-06-07 |
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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 |