IL23688A - Condensation products of naphtho-1,8-sultone and their use as levelling agents for electro-deposited coatings - Google Patents
Condensation products of naphtho-1,8-sultone and their use as levelling agents for electro-deposited coatingsInfo
- Publication number
- IL23688A IL23688A IL23688A IL2368865A IL23688A IL 23688 A IL23688 A IL 23688A IL 23688 A IL23688 A IL 23688A IL 2368865 A IL2368865 A IL 2368865A IL 23688 A IL23688 A IL 23688A
- Authority
- IL
- Israel
- Prior art keywords
- condensation products
- sultone
- naphtho
- electrolytic bath
- bath compositions
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 14
- 239000003795 chemical substances by application Substances 0.000 title description 8
- 238000000576 coating method Methods 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000003792 electrolyte Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000008053 sultones Chemical class 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 2
- FZWBGUCUIVJVNZ-UHFFFAOYSA-N C(C#CC)(O)O.OC(COCC(O)O)O Chemical compound C(C#CC)(O)O.OC(COCC(O)O)O FZWBGUCUIVJVNZ-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000007747 plating Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 229910052759 nickel Inorganic materials 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 heterocyclic tertiary amines Chemical class 0.000 description 4
- 230000000149 penetrating effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910001453 nickel ion Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- BZMYFCJDZSQRCI-UHFFFAOYSA-K nickel(3+) sulfamate sulfate Chemical compound S(N)([O-])(=O)=O.S(=O)(=O)([O-])[O-].[Ni+3] BZMYFCJDZSQRCI-UHFFFAOYSA-K 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/12—Electroplating: Baths therefor from solutions of nickel or cobalt
- C25D3/14—Electroplating: Baths therefor from solutions of nickel or cobalt from baths containing acetylenic or heterocyclic compounds
- C25D3/18—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electroplating And Plating Baths Therefor (AREA)
Description
condensation products of and their as levelling agents for 22750 This invention consists in new condensation products of one known as The invention also concerns the use of these compounds as levelling agents for particularly of and in this connection it is an object of the invention to improve electrol particularly in respect of their stability and power of penetrating the metal to be The present invention provides condensation products of one with heterocyclic nitrogen bases containing in the molecule at least one hydrogen atom and at least one heterooyclio ring comprising at least one nitrogen Preferred heterocyclic nitrogen bases of this kind are indolenlne form of porphine and The also provides electrolytic bat particularly for which contain as a levelling agent from about 5 to about 600 mg of at least one of the tion products per litre of the invention provides a process for manufacturing the new condensation products wherein such is reacted with nitrogen base in substantially stoichiometric The reaction is preferably performed in an aqueous medium at a of and at a temperature of about and the reaction mixture may the be The invention is particularly suitable for electrolytes containing a mixture of nickel sulfate and nickel or a mixture o and nickel with heterocyclic tertiary amines and having a structure including one or more aromatic nuclei are The use of such compounds in electrolytes containing nickel ions disclosed in the French Patent Specification which mentions produots of the condensation of such as or aultones derived from or aromatic sulfonic acids having the ttached at the 3 positions with respect to the sulfonic acid such as tolylsul one and with compounds containing the pyridine or diazine ring one or two optionally substituted enzene nuclei linked to the aforesaid heterocyclic These known particularly the products of the reaction of pyridine or quinoline with have a levelling effect on ordinary bright but their action diminishes rapidly with time and it is necessary to regenerate the compounds to time by heating the electrolyte for several hours at to has pointed out in the French Patent Specification the addition of these oompounds considerably reduces the penetrating power of the which is a drawback when articles of complicated shapes are to As distinct therefrom the condensation products to the when added to ve an improved levelling effect thereon without substantiall reducing the penetrating power of the the condensation compounds of the invention are stable in such owing to which property is no longer necessary to subject the electrolytes containing them to periodic re eneratin given by way of of the preparation of electrolytes for producing a bright Such bath may nickel sulfate sulfamate or possibly nickel to attack the boric at least one such as toluene hexamine or cyanurio at least one brigh such as an alcohol or an unsaturated at least one voltage lowering such as lauryl at least one condensation product according to the invention in a proportion of from about 5 mg to about mg per litre of of known brigh may be used the brighteners forming th subject of Israel Pa ent Specification The electrolyte bath is conveniently used the following agitation of the electrolyte temperature from to according to concentration of nickel ions and the desired rate of the temperature being preferably between and of from to preferably approximately 2 a current density of from 2 to 15 the best results being obtained with a current density of from 5 to 7 o for an at a temperature of about 65 The table below lists examples of baths of the table states the ro ortions in rams er litre TABLE Example 330 380 330 330 380 0 0 Nickel 0 0 0 0 0 400 400 80 45 80 80 45 30 30 40 40 40 40 40 50 50 Saccharine amide oa acid 0 0 Butyne 0 0 0 levelling compoundst Compound A 0 0 0 0 Compound B 0 0 0 0 0 Compound 0 0 0 0 Compound D 0 0 0 0 Compound S 0 0 0 0 0 Compound 0 0 0 0 0 0 Compound 0 0 0 0 0 0 Brighteners Compound H 0 0 0 0 pH 60 60 15 15 The levelling compounds A to G as well as the brightening oompound H of the above table are as Compound Indolenine produced by one mol of indolenine of the formula with one of Compound A is beet used in the proportion of from 10 to 500 per litre of Compound produced by reacting one of aodium salt of indole of the formula with one mol of Compound B is best used in the proportion of from to 500 per litre of electro Compound produoed by reacting one mol of phthalocyanine of the formula with four of C is best used in the proportion of from 10 to per litre of Oomnound with one mol of Compound is best used in the proportion of from 20 to 600 per litre of Compound produced by reacting one mol of porphine of the formula with two moles of Compound E is best used in the proportion of from 10 to 150 per litre of Pi produced by reacting one mol of a porphyrine with two of Compound F is best used in the same proportion as compound Compound produced by reacting one mol of of the formula with one mol of Compound G is best used in the proportion of from 50 to 500 per litre of Compound Ht This brightening compound the product of the of It has been disclosed in Israel Patent Specification The compound H may be used in combination with of the levelling agents A to G Generally the condensation products according to the invention can be prepared by the following methods heterocyclic base containing a nitrogen heterocyclic ring and an active hydrogen atom la placed together with the sultone in stoichiometric proportions proportions in the case of compound D and in a flask fitted with a reflux Water and an for example are added to adjust the pH to The mixture is initially heated gradually to until the sultone then the temperature of the mixture is raised to about and kept at this temperature for about 4 The viscosity of the mixture increases and its consistency becomes reaction ture is then The product thus obtained can be used as as a levelling agent in electrolytic bath oomposltione such as those indicated Electrolytic baths containing levelling agents according to the invention produce and particularly nickel which ductile and perfectly level and which have no pitting or The penetrating power of the electrolyte is and the stability of the levelling agent is insufficientOCRQuality
Claims (3)
1.· Condensation products of naphtho-lt8^sultone with heterocyclic nitrogen bases containing in the molecule at least one active hydrogen atom and at leant one five-aemoered heterocyclic _ring comprising at least one nitrogen hetero a om.
2.* Condensation products according to Claim 1, wherein the heterocyclic nitrogen base is indolenine, sodium β-nitroso indole, phthalocyanine* lt5-dimethyl imidazole, Buccinimide, porphine or porphyrine (substituted porphine)*
3. Condensation products according to Claim 1, substantially as hereinbefore described and exemplified* 4· A process for the manufacture of condensation products as defined in Claim 1, wherein naphtho-l,8~sultone is reacted with a heterocyclic nitrogen base according to Claim · 5. A prooess according to Claim 4» wherein the reactants are used in substantially stoichiometric proportions* 6» A prooess according to Claim 4 or 5» wherein the reaction is performed in an aqueous medium pre erably at a pH of 3·5 - 4#0 and preferably at a temperature of about 85°0. 7· A prooess for the manufacture of condensation products according to Claim 1, 2» or 3, substantially as hereinbefore described and exemplified* 8· Electrolytic bath compositions, in particular for nickel-plating, which contain from about 5 to about 600 tag of at least one of the condensation products according to Claims 1, 2 or 3 per litre of electrolyte. 9· Electrolytic bath compositions acoording to Claim 8* in which the condensation roduct is used directl in the state in 23688/2 - 10 - any of Claims 4 to 7· 10· Electrolytic bath compositions according to Claim 8 or 9t which contain in addition a brightener being of the reaction product/e¾uimolar amounts of bis-hydroxyethyl ether butyne diol and naphtho-lt8-sultone» 11· Electrolytic bath compositions substantially as described in any one of Examples 1 to 7 of the Table herein. PC/DL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR990780A FR1418244A (en) | 1964-10-08 | 1964-10-08 | New sultones and their application as leveling agents for electrolytic coatings, especially nickel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL23688A true IL23688A (en) | 1969-01-29 |
Family
ID=8839948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL23688A IL23688A (en) | 1964-10-08 | 1965-06-08 | Condensation products of naphtho-1,8-sultone and their use as levelling agents for electro-deposited coatings |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3423296A (en) |
| BE (1) | BE662876A (en) |
| DE (1) | DE1228886C2 (en) |
| FR (1) | FR1418244A (en) |
| GB (1) | GB1099186A (en) |
| IL (1) | IL23688A (en) |
| NL (1) | NL6504673A (en) |
| SE (1) | SE306210B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107531859B (en) | 2015-04-28 | 2020-02-14 | 罗门哈斯电子材料有限责任公司 | Reaction products of dianhydrides and diamines as plating bath additives |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA622565A (en) * | 1961-06-20 | L. Towle Jack | Electrodeposition of nickel | |
| US1564414A (en) * | 1924-10-06 | 1925-12-08 | Grasselli Chemical Co | Cadmium plating |
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
| US2469727A (en) * | 1944-03-30 | 1949-05-10 | Du Pont | Electrodeposition of nickel |
| DE1075398B (en) * | 1954-03-22 | 1960-02-11 | DEHYDAG Deutsche Hydrierwerke G.m.b.H., Düsseldorf | Bath for the galvanic production of metal coatings |
| NL100419C (en) * | 1955-03-16 | |||
| US2850507A (en) * | 1956-05-09 | 1958-09-02 | Monsanto Chemicals | Amidophosphorus compounds |
| NL110592C (en) * | 1956-06-15 | |||
| DE1182930B (en) * | 1961-06-12 | 1964-12-03 | Dehydag Gmbh | Process for the regeneration of nickel baths |
-
1964
- 1964-10-08 FR FR990780A patent/FR1418244A/en not_active Expired
-
1965
- 1965-01-12 DE DE1965P0035857 patent/DE1228886C2/en not_active Expired
- 1965-04-13 NL NL6504673A patent/NL6504673A/xx unknown
- 1965-04-22 BE BE662876D patent/BE662876A/xx unknown
- 1965-04-23 GB GB17296/65A patent/GB1099186A/en not_active Expired
- 1965-04-23 SE SE5312/65A patent/SE306210B/xx unknown
- 1965-06-08 IL IL23688A patent/IL23688A/en unknown
- 1965-10-01 US US492266A patent/US3423296A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE306210B (en) | 1968-11-18 |
| GB1099186A (en) | 1968-01-17 |
| DE1228886B (en) | 1966-11-17 |
| FR1418244A (en) | 1965-11-19 |
| DE1228886C2 (en) | 1974-07-04 |
| US3423296A (en) | 1969-01-21 |
| NL6504673A (en) | 1966-04-12 |
| BE662876A (en) | 1965-10-22 |
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