JPS601341B2 - ジアザロ−ダミンラクトン及びその製法 - Google Patents
ジアザロ−ダミンラクトン及びその製法Info
- Publication number
- JPS601341B2 JPS601341B2 JP51023753A JP2375376A JPS601341B2 JP S601341 B2 JPS601341 B2 JP S601341B2 JP 51023753 A JP51023753 A JP 51023753A JP 2375376 A JP2375376 A JP 2375376A JP S601341 B2 JPS601341 B2 JP S601341B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- parts
- lactone
- formulas
- 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
- 150000002596 lactones Chemical class 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 β-methoxyethyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- WAHBYPMCDMLQAV-UHFFFAOYSA-N 2-(dibutylamino)-6-phenyl-1h-pyrimidin-4-one Chemical compound CCCCN(CCCC)C1=NC(O)=CC(C=2C=CC=CC=2)=N1 WAHBYPMCDMLQAV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- VNAFWALXWOAPCK-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1h-indene Chemical compound C1CC2=CC=CC=C2C1C1=CC=CC=C1 VNAFWALXWOAPCK-UHFFFAOYSA-N 0.000 description 1
- MHCXWAFWYAQMAE-UHFFFAOYSA-N 2-(dibutylamino)-6-(4-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound CCCCN(CCCC)C1=NC(O)=CC(C=2C=CC(OC)=CC=2)=N1 MHCXWAFWYAQMAE-UHFFFAOYSA-N 0.000 description 1
- MFXNIXTXWYFERG-UHFFFAOYSA-N 2-(diethylamino)-6-phenyl-1h-pyrimidin-4-one Chemical compound CCN(CC)C1=NC(O)=CC(C=2C=CC=CC=2)=N1 MFXNIXTXWYFERG-UHFFFAOYSA-N 0.000 description 1
- BMCGBRKMSVYAPS-UHFFFAOYSA-N 2-[4-(2-chloroanilino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C(C(=C1)O)=CC=C1NC1=CC=CC=C1Cl BMCGBRKMSVYAPS-UHFFFAOYSA-N 0.000 description 1
- MLKBAQXCOPYVQV-UHFFFAOYSA-N 2-[4-(4-chloroanilino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C(C(=C1)O)=CC=C1NC1=CC=C(Cl)C=C1 MLKBAQXCOPYVQV-UHFFFAOYSA-N 0.000 description 1
- QPNFUBAIQZJEPO-UHFFFAOYSA-N 2-[4-(dibutylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QPNFUBAIQZJEPO-UHFFFAOYSA-N 0.000 description 1
- GLELQLHCSRTFFD-UHFFFAOYSA-N 2-[4-(dimethylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1C(O)=O GLELQLHCSRTFFD-UHFFFAOYSA-N 0.000 description 1
- QXGZXDUYFNMZPE-UHFFFAOYSA-N 2-[4-(dipropylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCC)CCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QXGZXDUYFNMZPE-UHFFFAOYSA-N 0.000 description 1
- AWTRFGBAOOYGSF-UHFFFAOYSA-N 2-morpholin-4-yl-6-phenyl-1h-pyrimidin-4-one Chemical compound N=1C(=O)C=C(C=2C=CC=CC=2)NC=1N1CCOCC1 AWTRFGBAOOYGSF-UHFFFAOYSA-N 0.000 description 1
- LDORHCBMWSQLIU-UHFFFAOYSA-N 6-phenyl-1h-pyrimidin-2-one Chemical compound N1C(=O)N=CC=C1C1=CC=CC=C1 LDORHCBMWSQLIU-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
-
- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2509793A DE2509793C2 (de) | 1975-03-06 | 1975-03-06 | Diazarhodaminlactone und deren Verwendung als Farbbildner für Kopieverfahren |
| DE2509793.2 | 1975-03-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51111833A JPS51111833A (en) | 1976-10-02 |
| JPS601341B2 true JPS601341B2 (ja) | 1985-01-14 |
Family
ID=5940643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51023753A Expired JPS601341B2 (ja) | 1975-03-06 | 1976-03-06 | ジアザロ−ダミンラクトン及びその製法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4052398A (en:Method) |
| JP (1) | JPS601341B2 (en:Method) |
| CH (1) | CH599216A5 (en:Method) |
| DE (1) | DE2509793C2 (en:Method) |
| FR (1) | FR2303017A1 (en:Method) |
| GB (1) | GB1535855A (en:Method) |
| IT (1) | IT1056200B (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10988877B2 (en) | 2017-03-24 | 2021-04-27 | Janome Sewing Machine Co., Ltd. | Overlock sewing machine |
| US10988878B2 (en) | 2017-03-24 | 2021-04-27 | Janome Sewing Machine Co., Ltd. | Overlock sewing machine |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4272535A (en) * | 1978-07-31 | 1981-06-09 | Schering Corporation | 2,4-[1H,3H,5H]-(1)-Benzopyrano-[2,3-d]-pyrimidinediones and their use as anti-allergy agents |
| US4297355A (en) * | 1979-11-15 | 1981-10-27 | Schering Corporation | (1H,3H,5H)-(1)-Benzopyrano-(2,3-d)-pyrimidine-4-one-2-thiones and their use as anti-allergy agents |
| JP3917269B2 (ja) * | 1997-10-07 | 2007-05-23 | パイロットインキ株式会社 | 可逆熱変色性組成物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1349093A (en) * | 1971-09-23 | 1974-03-27 | British Hovercraft Corp Ltd | Ship assembly and repair |
| DE2243483C2 (de) * | 1972-09-05 | 1985-01-31 | Basf Ag, 6700 Ludwigshafen | Neue Diazaxanthenlactone, deren Herstellung und deren Verwendung als Farbbildner für Kopierverfahren |
-
1975
- 1975-03-06 DE DE2509793A patent/DE2509793C2/de not_active Expired
-
1976
- 1976-02-13 US US05/657,861 patent/US4052398A/en not_active Expired - Lifetime
- 1976-02-26 IT IT48302/76A patent/IT1056200B/it active
- 1976-03-03 CH CH267076A patent/CH599216A5/xx not_active IP Right Cessation
- 1976-03-04 FR FR7606135A patent/FR2303017A1/fr active Granted
- 1976-03-04 GB GB8652/76A patent/GB1535855A/en not_active Expired
- 1976-03-06 JP JP51023753A patent/JPS601341B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10988877B2 (en) | 2017-03-24 | 2021-04-27 | Janome Sewing Machine Co., Ltd. | Overlock sewing machine |
| US10988878B2 (en) | 2017-03-24 | 2021-04-27 | Janome Sewing Machine Co., Ltd. | Overlock sewing machine |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2303017B1 (en:Method) | 1981-12-18 |
| FR2303017A1 (fr) | 1976-10-01 |
| US4052398A (en) | 1977-10-04 |
| DE2509793A1 (de) | 1976-09-16 |
| GB1535855A (en) | 1978-12-13 |
| CH599216A5 (en:Method) | 1978-05-12 |
| JPS51111833A (en) | 1976-10-02 |
| DE2509793C2 (de) | 1985-01-10 |
| IT1056200B (it) | 1982-01-30 |
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