GB1596565A - Azo dyes - Google Patents
Azo dyes Download PDFInfo
- Publication number
- GB1596565A GB1596565A GB388678A GB388678A GB1596565A GB 1596565 A GB1596565 A GB 1596565A GB 388678 A GB388678 A GB 388678A GB 388678 A GB388678 A GB 388678A GB 1596565 A GB1596565 A GB 1596565A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- aniline
- good
- benzamido
- enamel
- 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
- 239000000987 azo dye Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 230000008878 coupling Effects 0.000 claims description 17
- 238000010168 coupling process Methods 0.000 claims description 17
- 210000003298 dental enamel Anatomy 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 11
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 9
- 239000004800 polyvinyl chloride Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000976 ink Substances 0.000 claims description 5
- 239000004640 Melamine resin Substances 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- 238000000265 homogenisation Methods 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 claims description 2
- 230000000536 complexating effect Effects 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052573 porcelain Inorganic materials 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- -1 heterocyclic hydroxy compounds Chemical class 0.000 description 7
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006193 diazotization reaction Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RXJCXGJKJZARAW-UHFFFAOYSA-N 4-chloro-1,2-dimethoxybenzene Chemical compound COC1=CC=C(Cl)C=C1OC RXJCXGJKJZARAW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- UPBIVMVNDOALIE-UHFFFAOYSA-N n-(3-amino-2-methylphenyl)benzamide Chemical compound CC1=C(N)C=CC=C1NC(=O)C1=CC=CC=C1 UPBIVMVNDOALIE-UHFFFAOYSA-N 0.000 description 2
- ZKMYHZKZDMIROQ-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)benzamide Chemical compound C1=C(N)C(C)=CC=C1NC(=O)C1=CC=CC=C1 ZKMYHZKZDMIROQ-UHFFFAOYSA-N 0.000 description 2
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- DFHYLJFFCDLEBS-UHFFFAOYSA-N 1h-pyrazole-4,5-dione Chemical compound OC1=CN=NC1=O DFHYLJFFCDLEBS-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical class C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
- RUFOHZDEBFYQSV-UHFFFAOYSA-N 4-methoxy-3-nitroaniline Chemical compound COC1=CC=C(N)C=C1[N+]([O-])=O RUFOHZDEBFYQSV-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- SGYBFMHFBBYSFQ-UHFFFAOYSA-N C1(=CC=CC=C1)N1N=C(C=C1O)C(N)=O Chemical compound C1(=CC=CC=C1)N1N=C(C=C1O)C(N)=O SGYBFMHFBBYSFQ-UHFFFAOYSA-N 0.000 description 1
- BFCZBMZMVYRCAB-UHFFFAOYSA-N C1(=CC=CC=C1)N1N=C(C=C1O)C(NC1=C(C=CC(=C1)Cl)OC)=O Chemical compound C1(=CC=CC=C1)N1N=C(C=C1O)C(NC1=C(C=CC(=C1)Cl)OC)=O BFCZBMZMVYRCAB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- BSVOTWLTVAXQCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)-2,4-dichlorobenzamide Chemical compound C1=C(N)C(OC)=CC=C1NC(=O)C1=CC=C(Cl)C=C1Cl BSVOTWLTVAXQCV-UHFFFAOYSA-N 0.000 description 1
- HCXZVGVPPSVNQB-UHFFFAOYSA-N n-(3-amino-4-methylphenyl)-2,4-dichlorobenzamide Chemical compound C1=C(N)C(C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1Cl HCXZVGVPPSVNQB-UHFFFAOYSA-N 0.000 description 1
- IRFCTHNJIWUUJZ-UHFFFAOYSA-N n-(3-aminophenyl)benzamide Chemical compound NC1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 IRFCTHNJIWUUJZ-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical class C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1984877A IT1076855B (it) | 1977-02-01 | 1977-02-01 | Coloranti monoazoici insolubili in acqua |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1596565A true GB1596565A (en) | 1981-08-26 |
Family
ID=11161777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB388678A Expired GB1596565A (en) | 1977-02-01 | 1978-01-31 | Azo dyes |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS53114837A (en, 2012) |
| DE (1) | DE2803992A1 (en, 2012) |
| FR (1) | FR2378826A1 (en, 2012) |
| GB (1) | GB1596565A (en, 2012) |
| IT (1) | IT1076855B (en, 2012) |
| NL (1) | NL7800995A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9555200B2 (en) | 2011-03-15 | 2017-01-31 | Novartis Ag | Inhaler |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2587981B2 (ja) * | 1988-03-22 | 1997-03-05 | 三菱電線工業株式会社 | 耐熱老化性樹脂組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH114916A (de) * | 1924-03-29 | 1926-05-17 | Hoechst Ag | Verfahren zur Darstellung eines Azofarbstoffes. |
| CH111495A (de) * | 1924-05-22 | 1925-08-17 | Chem Fab Rohner A G Pratteln | Verfahren zur Darstellung eines Monoazofarbstoffes. |
| US1872033A (en) * | 1931-02-02 | 1932-08-16 | Dow Chemical Co | Fast azo dye |
| FR810699A (fr) * | 1935-09-21 | 1937-03-26 | Ig Farbenindustrie Ag | Colorants mono-azoïques insolubles dans l'eau et procédé de préparation de ces colorants |
| FR850220A (fr) * | 1938-02-11 | 1939-12-11 | Ig Farbenindustrie Ag | Colorants mono-azoïques et procédé de préparation de ces colorants |
| FR50607E (fr) * | 1939-05-05 | 1941-01-27 | Ig Farbenindustrie Ag | Colorants monoazoïques et procédé de préparation de ces colorants |
| BE788450A (fr) * | 1971-09-08 | 1973-03-06 | Bayer Ag | Nouveaux pigments monoazoiques, leur procede de preparation et leurs applications |
-
1977
- 1977-02-01 IT IT1984877A patent/IT1076855B/it active
-
1978
- 1978-01-27 NL NL7800995A patent/NL7800995A/xx not_active Application Discontinuation
- 1978-01-30 FR FR7802477A patent/FR2378826A1/fr active Granted
- 1978-01-31 DE DE19782803992 patent/DE2803992A1/de not_active Withdrawn
- 1978-01-31 GB GB388678A patent/GB1596565A/en not_active Expired
- 1978-02-01 JP JP937278A patent/JPS53114837A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9555200B2 (en) | 2011-03-15 | 2017-01-31 | Novartis Ag | Inhaler |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2378826A1 (fr) | 1978-08-25 |
| IT1076855B (it) | 1985-04-27 |
| NL7800995A (nl) | 1978-08-03 |
| FR2378826B1 (en, 2012) | 1980-05-16 |
| DE2803992A1 (de) | 1978-08-03 |
| JPS53114837A (en) | 1978-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |