GB736792A - Condensation products of complex copper compounds with nitrogen-containing compounds and aldehydes - Google Patents
Condensation products of complex copper compounds with nitrogen-containing compounds and aldehydesInfo
- Publication number
- GB736792A GB736792A GB11446/52A GB1144652A GB736792A GB 736792 A GB736792 A GB 736792A GB 11446/52 A GB11446/52 A GB 11446/52A GB 1144652 A GB1144652 A GB 1144652A GB 736792 A GB736792 A GB 736792A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copper
- formaldehyde
- dicyandiamide
- complex
- chloride
- 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
- 150000001299 aldehydes Chemical class 0.000 title abstract 3
- 239000005749 Copper compound Substances 0.000 title abstract 2
- 239000007859 condensation product Substances 0.000 title abstract 2
- 150000001880 copper compounds Chemical class 0.000 title abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 30
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 13
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 9
- 235000019270 ammonium chloride Nutrition 0.000 abstract 7
- 229940123208 Biguanide Drugs 0.000 abstract 6
- -1 amine salt Chemical class 0.000 abstract 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 abstract 6
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 4
- 230000005494 condensation Effects 0.000 abstract 4
- 238000009833 condensation Methods 0.000 abstract 4
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 abstract 3
- 238000004043 dyeing Methods 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 2
- 229920003043 Cellulose fiber Polymers 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 150000001879 copper Chemical class 0.000 abstract 2
- 150000004699 copper complex Chemical class 0.000 abstract 2
- RSJOBNMOMQFPKQ-UHFFFAOYSA-L copper;2,3-dihydroxybutanedioate Chemical compound [Cu+2].[O-]C(=O)C(O)C(O)C([O-])=O RSJOBNMOMQFPKQ-UHFFFAOYSA-L 0.000 abstract 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 2
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 abstract 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 2
- 229920000768 polyamine Polymers 0.000 abstract 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229960001124 trientine Drugs 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 abstract 1
- XGQWHHCZIMXNHG-UHFFFAOYSA-N 4-aminonaphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 XGQWHHCZIMXNHG-UHFFFAOYSA-N 0.000 abstract 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 abstract 1
- LPXQRXLUHJKZIE-UHFFFAOYSA-N 8-azaguanine Chemical compound NC1=NC(O)=C2NN=NC2=N1 LPXQRXLUHJKZIE-UHFFFAOYSA-N 0.000 abstract 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000005752 Copper oxychloride Substances 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 150000004705 aldimines Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 abstract 1
- 150000005010 aminoquinolines Chemical class 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 1
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 1
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 abstract 1
- 229940015043 glyoxal Drugs 0.000 abstract 1
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960003540 oxyquinoline Drugs 0.000 abstract 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920003987 resole Polymers 0.000 abstract 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/56—Condensation products or precondensation products prepared with aldehydes
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/043—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
- C08G12/14—Dicyandiamides; Dicyandiamidines; Guanidines; Biguanidines; Biuret; Semicarbazides
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/10—After-treatment with compounds containing metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Abstract
The wet-fastness of dyeings and prints made with water-soluble substantive dyestuffs on cellulose fibres is enhanced by treating them with an aqueous solution of a resin made by condensing an aldehyde, a complex copper salt and a compound of the urea family containing at least once the grouping <FORM:0736792/IV (c)/1> The condensation may be performed in presence of an ammonium salt, an amine or an amine salt. The Specification contains lists of reactants. If the dyestuffs are capable of being after-metallized, the treatment may be performed in presence of a copper complex or copper salt, e.g. copper chloride, copper acetate or copper tartrate. In examples: (1) cotton yarn dyed with Benzolichtrot 8BL is treated with an aqueous solution of a condensate of bis-(diethylenetriamine)-copper chloride, dicyandiamide and formaldehyde; (4) cotton fibres which are dyed with the diazo dyestuff obtained by coupling diazotized 1-amino-naphthalene-3,7-disulphonic acid with 1-amino-2-methoxy-5-methylbenzene and reacting the product with phosgene are treated with the condensation product of biguanide copper acetate, ammonium chloride, dicyandiamide and formaldehyde.ALSO:Water-soluble condensates are made by condensing together (1) a nitrogen-containing complex copper compound; (2) an aldehyde; and (3) a compound having one or more of the groups <FORM:0736792/IV (a)/1> Condensation is effected by heating to produce a dark violet, blue or green solution which may be heated to dryness in vacuo and the remaining resin subjected to further condensation by heating. Aqueous solutions of the condensates enhance the wet-fastness of dyeing or prints made with water-soluble substantive dyestuffs on cellulose fibres (see Group IV (c). Specified are:-copper p complexes of dicyandiamidine, biguanide, guanazoles, ethylene diamine, polyethylene polyamines, 8-hydroxy- or aminoquinoline, 3-hydroxyphenyl biguanide or glycocoll, the aldimine series and of mixed resoles obtained from phenols, 8-hydroxyquinoline and formaldehyde; aldehydes-formaldehyde, acetaldehyde, glyoxal, chloral, crotonaldehyde, hexamethylene tetramine; compounds with the specified group-dicyandiamide, dicyandiamidine, biguanide and its alkyl and aryl derivatives, guanidine, amino guanidine, melamine and guanazol. Condensation may be performed in presence of ammonium chloride, diethylene triamine or triethylene tetramine or their chlorhydrates. In examples: (1) Bis - (diethylenetriamine) - copper chloride, dicyandiamide and formaldehyde are condensed in presence of HCl. (2) The complex of copper chloride and guanazole, formaldehyde and guanazole are condensed alone or in presence of HCl. (3) The complex of dicyandiamidine and copper acetate, dicyandiamide, formaldehyde and ammonium chloride are heated together. (4) Biguanide copper acetate, ammonium chloride, dicyandiamide and formaldehyde are heated together. (5) Dicyandiamide is partly converted into biguanide chlorhydrate by heating with ammonium chloride, copper acetate added to form the biguanide complex and the whole heated with ammonia and formaldehyde. (6) Copper chloride-diethylene triamine complex is neutralized with HCl and heated together with dicyandiamide formaldehyde and ammonium chloride. The solution together with copper chloride, copper acetate, copper tartrate or a copper complex may be used to improve the wet-fastness of dyeings. (7) Copper chloride-diethylene triamine complex is neutralized with HCl and condensed with dicyandiamide and formaldehyde. Instead of diethylene triamine there may be used a polyamine made by reacting ethylene dichloride with ammonia and distilling off volatile components. (8) Copper oxychloride dissolved in HCl is treated with a mixture of diethylene triamine and triethylene tetramine. The solution is then heated with guanidine sulphate, dicyandiamide, formaldehyde, ammonium sulphate, and ammonium acetate or chloride. Specifications 619,969 and 691,686, [Group IV (b)], are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE312647X | 1951-05-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB736792A true GB736792A (en) | 1955-09-14 |
Family
ID=6136138
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11446/52A Expired GB736792A (en) | 1951-05-10 | 1952-05-06 | Condensation products of complex copper compounds with nitrogen-containing compounds and aldehydes |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH312647A (en) |
FR (1) | FR1066111A (en) |
GB (1) | GB736792A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3198595A (en) * | 1965-08-03 | Step-wise process for coloring anb fin- ishing cellulose materials wherein a cationic dye-fixing agent is employed with the resin finishing agent |
-
1952
- 1952-05-06 GB GB11446/52A patent/GB736792A/en not_active Expired
- 1952-05-08 CH CH312647D patent/CH312647A/en unknown
- 1952-05-09 FR FR1066111D patent/FR1066111A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3198595A (en) * | 1965-08-03 | Step-wise process for coloring anb fin- ishing cellulose materials wherein a cationic dye-fixing agent is employed with the resin finishing agent |
Also Published As
Publication number | Publication date |
---|---|
FR1066111A (en) | 1954-06-02 |
CH312647A (en) | 1956-02-15 |
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