DE2344834A1 - Cumarinderivate und ihre verwendung als optische aufheller - Google Patents
Cumarinderivate und ihre verwendung als optische aufhellerInfo
- Publication number
- DE2344834A1 DE2344834A1 DE19732344834 DE2344834A DE2344834A1 DE 2344834 A1 DE2344834 A1 DE 2344834A1 DE 19732344834 DE19732344834 DE 19732344834 DE 2344834 A DE2344834 A DE 2344834A DE 2344834 A1 DE2344834 A1 DE 2344834A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- compound
- substituted
- oxadiazol
- 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.)
- Ceased
Links
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims description 11
- 230000003287 optical effect Effects 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- -1 3-methyl-1,2,4-oxadiazol-5-yl Chemical group 0.000 claims description 8
- 229960000956 coumarin Drugs 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 235000001671 coumarin Nutrition 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- QKJALQPLNMEDAV-UHFFFAOYSA-N 2-oxochromene-3-carbonitrile Chemical compound C1=CC=CC2=C1OC(=O)C(C#N)=C2 QKJALQPLNMEDAV-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000004753 textile Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920002994 synthetic fiber Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007844 bleaching agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000271 synthetic detergent Substances 0.000 description 2
- 239000004758 synthetic textile Substances 0.000 description 2
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ACMLKANOGIVEPB-UHFFFAOYSA-N 2-oxo-2H-chromene-3-carboxylic acid Chemical compound C1=CC=C2OC(=O)C(C(=O)O)=CC2=C1 ACMLKANOGIVEPB-UHFFFAOYSA-N 0.000 description 1
- ISWHFVFEWCFBII-UHFFFAOYSA-M 3-[3-(1-methylpyridin-1-ium-2-yl)-1,2,4-oxadiazol-5-yl]-7-phenylmethoxychromen-2-one chloride Chemical compound [Cl-].C(C1=CC=CC=C1)OC1=CC=C2C=C(C(OC2=C1)=O)C1=NC(=NO1)C1=[N+](C=CC=C1)C ISWHFVFEWCFBII-UHFFFAOYSA-M 0.000 description 1
- IUYYAIYFKXGKKS-UHFFFAOYSA-N 3-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]chromen-2-one Chemical compound C1=CC(C)=CC=C1C1=NOC(C=2C(OC3=CC=CC=C3C=2)=O)=N1 IUYYAIYFKXGKKS-UHFFFAOYSA-N 0.000 description 1
- CTNXLXTUVUZBKP-UHFFFAOYSA-N 3-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]-7-phenylmethoxychromen-2-one Chemical compound ClCC1=NOC(C=2C(OC3=CC(OCC=4C=CC=CC=4)=CC=C3C=2)=O)=N1 CTNXLXTUVUZBKP-UHFFFAOYSA-N 0.000 description 1
- WREQQTGOXJJDPE-UHFFFAOYSA-N 3-[3-[(dibutylamino)methyl]-1,2,4-oxadiazol-5-yl]-7-phenylmethoxychromen-2-one Chemical compound CCCCN(CCCC)CC1=NOC(C=2C(OC3=CC(OCC=4C=CC=CC=4)=CC=C3C=2)=O)=N1 WREQQTGOXJJDPE-UHFFFAOYSA-N 0.000 description 1
- HCIQQGFQZYVOLX-UHFFFAOYSA-N 7-methoxy-2-oxochromene-3-carbonyl chloride Chemical compound C1=C(C(Cl)=O)C(=O)OC2=CC(OC)=CC=C21 HCIQQGFQZYVOLX-UHFFFAOYSA-N 0.000 description 1
- ONYRTHPVIUHYSF-UHFFFAOYSA-N 7-methoxy-3-(3-methyl-1,2,4-oxadiazol-5-yl)chromen-2-one Chemical compound O=C1OC2=CC(OC)=CC=C2C=C1C1=NC(C)=NO1 ONYRTHPVIUHYSF-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- DTBUWUADUUJZTQ-UHFFFAOYSA-M [Cl-].COC1=CC=C2C=C(C(OC2=C1)=O)C1=NC(=NO1)C1=[N+](C=CC=C1)C Chemical compound [Cl-].COC1=CC=C2C=C(C(OC2=C1)=O)C1=NC(=NO1)C1=[N+](C=CC=C1)C DTBUWUADUUJZTQ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 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
- 150000004775 coumarins Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 125000005077 diacylhydrazine group Chemical group 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- NKJXMLIWSJATEE-UHFFFAOYSA-N n'-hydroxy-4-methylbenzenecarboximidamide Chemical compound CC1=CC=C(C(N)=NO)C=C1 NKJXMLIWSJATEE-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Coloring (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4141672A GB1388590A (en) | 1972-09-06 | 1972-09-06 | 3-oxadiazolyl-coumarins and their use as brightening agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2344834A1 true DE2344834A1 (de) | 1974-03-21 |
Family
ID=10419588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732344834 Ceased DE2344834A1 (de) | 1972-09-06 | 1973-09-05 | Cumarinderivate und ihre verwendung als optische aufheller |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3933842A (enExample) |
| JP (1) | JPS5338355B2 (enExample) |
| CH (2) | CH578076B5 (enExample) |
| DE (1) | DE2344834A1 (enExample) |
| GB (1) | GB1388590A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2296636A2 (fr) * | 1974-12-30 | 1976-07-30 | Ugine Kuhlmann | Nouveaux derives de coumarine utilisables comme azurants optiques |
| EP0030703A1 (de) * | 1979-12-14 | 1981-06-24 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Cumarinverbindungen |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO762107L (enExample) * | 1975-06-27 | 1976-12-28 | Sumitomo Chemical Co | |
| US4882412A (en) * | 1987-11-30 | 1989-11-21 | Eastman Kodak Company | Polyester polymer containing the residue of the UV absorbing benzopyran compound and shaped articles produced therefrom |
| CN1506359A (zh) * | 2002-12-05 | 2004-06-23 | �й�ҽѧ��ѧԺҩ���о��� | 新的香豆素酰胺衍生物及其制法和其药物组合物与用途 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1382581A (en) * | 1971-02-11 | 1975-02-05 | Hickson & Welch Ltd | Coumarin-based quaternary salts |
-
1972
- 1972-09-06 GB GB4141672A patent/GB1388590A/en not_active Expired
-
1973
- 1973-09-05 DE DE19732344834 patent/DE2344834A1/de not_active Ceased
- 1973-09-05 CH CH1279073A patent/CH578076B5/xx not_active IP Right Cessation
- 1973-09-05 US US05/394,494 patent/US3933842A/en not_active Expired - Lifetime
- 1973-09-05 CH CH1279073D patent/CH1279073A4/xx unknown
- 1973-09-05 JP JP9934573A patent/JPS5338355B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2296636A2 (fr) * | 1974-12-30 | 1976-07-30 | Ugine Kuhlmann | Nouveaux derives de coumarine utilisables comme azurants optiques |
| EP0030703A1 (de) * | 1979-12-14 | 1981-06-24 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Cumarinverbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| US3933842A (en) | 1976-01-20 |
| GB1388590A (en) | 1975-03-26 |
| CH578076B5 (enExample) | 1976-07-30 |
| JPS4986423A (enExample) | 1974-08-19 |
| CH1279073A4 (enExample) | 1976-02-27 |
| JPS5338355B2 (enExample) | 1978-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |