DE2507459C3 - 4,5-Dialkoxy-N-cycloammoniumnaphthalimide - Google Patents
4,5-Dialkoxy-N-cycloammoniumnaphthalimideInfo
- Publication number
- DE2507459C3 DE2507459C3 DE19752507459 DE2507459A DE2507459C3 DE 2507459 C3 DE2507459 C3 DE 2507459C3 DE 19752507459 DE19752507459 DE 19752507459 DE 2507459 A DE2507459 A DE 2507459A DE 2507459 C3 DE2507459 C3 DE 2507459C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- naphthalimide
- blue
- och
- violet
- 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
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000005811 Viola adunca Nutrition 0.000 description 14
- 235000013487 Viola odorata Nutrition 0.000 description 14
- 235000002254 Viola papilionacea Nutrition 0.000 description 14
- -1 alkyl radical Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 240000009038 Viola odorata Species 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 244000154870 Viola adunca Species 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- BRYJEGDOYXLUHS-UHFFFAOYSA-N 1,2,3-trimethyl-5-phenylpyrazol-1-ium Chemical compound CN1C(C)=CC(C=2C=CC=CC=2)=[N+]1C BRYJEGDOYXLUHS-UHFFFAOYSA-N 0.000 description 2
- NLMISGYQTXQMDK-UHFFFAOYSA-N 1,3-dimethyl-2-phenylbenzimidazol-3-ium Chemical compound C[N+]=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 NLMISGYQTXQMDK-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 2
- 229960002218 sodium chlorite Drugs 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- NFLFDNVCHQPMTO-UHFFFAOYSA-N (4,5-dichloronaphthalene-1-carbonyl) 4,5-dichloronaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC(=O)C3=C4C=CC=C(C4=C(Cl)C=C3)Cl)=CC=C(Cl)C2=C1Cl NFLFDNVCHQPMTO-UHFFFAOYSA-N 0.000 description 1
- ZMKHDVWIHTXNTM-UHFFFAOYSA-N 1,2,3,5-tetramethylpyrazol-1-ium Chemical group CC1=CC(C)=[N+](C)N1C ZMKHDVWIHTXNTM-UHFFFAOYSA-N 0.000 description 1
- DTUDMIINCAAINX-UHFFFAOYSA-N 1,2,3-trimethylpyrazol-1-ium Chemical compound CC1=CC=[N+](C)N1C DTUDMIINCAAINX-UHFFFAOYSA-N 0.000 description 1
- UMZDENILBZKMFY-UHFFFAOYSA-N 1,2-dimethylpyridin-1-ium Chemical compound CC1=CC=CC=[N+]1C UMZDENILBZKMFY-UHFFFAOYSA-N 0.000 description 1
- KEOLYURDXNRJEY-UHFFFAOYSA-N 1,2-dimethylquinolin-1-ium Chemical compound C1=CC=CC2=[N+](C)C(C)=CC=C21 KEOLYURDXNRJEY-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- RTQPKEOYPPMVGQ-UHFFFAOYSA-N 1-methylquinolin-1-ium Chemical compound C1=CC=C2[N+](C)=CC=CC2=C1 RTQPKEOYPPMVGQ-UHFFFAOYSA-N 0.000 description 1
- NHQAVVKPLWMNBS-UHFFFAOYSA-N 2,4-dimethyl-5-phenyltriazole Chemical compound CC1=NN(C)N=C1C1=CC=CC=C1 NHQAVVKPLWMNBS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- LNVWRBNPXCUYJI-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazol-4-amine Chemical compound CC1=NNC(C)=C1N LNVWRBNPXCUYJI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AALSLNDNKLOORP-UHFFFAOYSA-N perchloric acid sulfuric acid Chemical compound OS(O)(=O)=O.OCl(=O)(=O)=O AALSLNDNKLOORP-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000004246 zinc acetate 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507459 DE2507459C3 (de) | 1975-02-21 | 1975-02-21 | 4,5-Dialkoxy-N-cycloammoniumnaphthalimide |
| IT4814476A IT1053864B (it) | 1975-02-21 | 1976-02-18 | Composti della serie delle n cicloammonionaftalimmidi |
| CH198176A CH620209A5 (en) | 1975-02-21 | 1976-02-18 | Process for the preparation of novel compounds of the N-cycloammonionaphthalimide series |
| FR7604573A FR2301520A1 (fr) | 1975-02-21 | 1976-02-19 | Seis d'ammonium quaternaires hétérocycliques dérivés du naphtalène 1,8-dicarboximide,leurs procédés de préparation et leur utilisation comme éclaircissants optiques pour fibres modifiées anioniquement |
| JP1715876A JPS51109022A (ja) | 1975-02-21 | 1976-02-20 | Nnkanjoanmoniumunafutaruimidokeikagobutsu |
| GB675176A GB1535358A (en) | 1975-02-21 | 1976-02-20 | Compounds of the n-cycloammonium naphthalimide series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507459 DE2507459C3 (de) | 1975-02-21 | 1975-02-21 | 4,5-Dialkoxy-N-cycloammoniumnaphthalimide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2507459A1 DE2507459A1 (de) | 1976-09-02 |
| DE2507459B2 DE2507459B2 (de) | 1979-03-22 |
| DE2507459C3 true DE2507459C3 (de) | 1979-11-15 |
Family
ID=5939436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752507459 Expired DE2507459C3 (de) | 1975-02-21 | 1975-02-21 | 4,5-Dialkoxy-N-cycloammoniumnaphthalimide |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS51109022A (enExample) |
| CH (1) | CH620209A5 (enExample) |
| DE (1) | DE2507459C3 (enExample) |
| FR (1) | FR2301520A1 (enExample) |
| GB (1) | GB1535358A (enExample) |
| IT (1) | IT1053864B (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1541050A (fr) * | 1967-08-11 | 1968-10-04 | Ugine Kuhlmann | Nouveaux agents de blanchiment optique, leur préparation et leurs applications |
| FR2186025A5 (enExample) * | 1972-05-24 | 1974-01-04 | Ugine Kuhlmann |
-
1975
- 1975-02-21 DE DE19752507459 patent/DE2507459C3/de not_active Expired
-
1976
- 1976-02-18 IT IT4814476A patent/IT1053864B/it active
- 1976-02-18 CH CH198176A patent/CH620209A5/de not_active IP Right Cessation
- 1976-02-19 FR FR7604573A patent/FR2301520A1/fr active Granted
- 1976-02-20 JP JP1715876A patent/JPS51109022A/ja active Pending
- 1976-02-20 GB GB675176A patent/GB1535358A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2301520A1 (fr) | 1976-09-17 |
| FR2301520B1 (enExample) | 1979-04-06 |
| DE2507459B2 (de) | 1979-03-22 |
| JPS51109022A (ja) | 1976-09-27 |
| DE2507459A1 (de) | 1976-09-02 |
| CH620209A5 (en) | 1980-11-14 |
| GB1535358A (en) | 1978-12-13 |
| IT1053864B (it) | 1981-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8330 | Complete disclaimer |