DE2213753A1 - Bis-styryltriazole, deren Verwendung zum optischen Aufhellen von organischen Materialien und Verfahren zu deren Herstellung - Google Patents
Bis-styryltriazole, deren Verwendung zum optischen Aufhellen von organischen Materialien und Verfahren zu deren HerstellungInfo
- Publication number
- DE2213753A1 DE2213753A1 DE19722213753 DE2213753A DE2213753A1 DE 2213753 A1 DE2213753 A1 DE 2213753A1 DE 19722213753 DE19722213753 DE 19722213753 DE 2213753 A DE2213753 A DE 2213753A DE 2213753 A1 DE2213753 A1 DE 2213753A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrogen
- carbon atoms
- halogen
- bis
- 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.)
- Pending
Links
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- 239000011368 organic material Substances 0.000 title claims description 7
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- 238000000034 method Methods 0.000 title description 25
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- 239000000460 chlorine Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- 229910052708 sodium Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- DYGINNXQEXTSGJ-UHFFFAOYSA-N 1-oxido-3-(1,2,4-triazol-3-ylidene)-1,2,4-triazol-1-ium Chemical compound [N+]1(=NC(N=C1)=C1N=NC=N1)[O-] DYGINNXQEXTSGJ-UHFFFAOYSA-N 0.000 description 2
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- 150000001989 diazonium salts Chemical class 0.000 description 1
- QQSBWCNELOEITJ-UHFFFAOYSA-N dibenzofuran-3,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3OC2=C1 QQSBWCNELOEITJ-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- AOSJNFGVUJMQKB-UHFFFAOYSA-N hydrazine hypochlorous acid Chemical compound NN.ClO AOSJNFGVUJMQKB-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BBDNZMUIQBRBJH-UHFFFAOYSA-N sulfurochloridic acid;toluene Chemical compound OS(Cl)(=O)=O.CC1=CC=CC=C1 BBDNZMUIQBRBJH-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/22—Naphthotriazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH470371A CH554392A (de) | 1971-03-31 | 1971-03-31 | Verwendung von styryl-v-triazolen zum optischen aufhellen von organischen materialien ausserhalb der textilindustrie. |
| CH470071A CH554389A (de) | 1971-03-31 | 1971-03-31 | Verwendung von bis-styryltriazolen zum optischen aufhellen von organischen materialien ausserhalb der textilindustrie. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2213753A1 true DE2213753A1 (de) | 1972-10-12 |
Family
ID=25696099
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722213753 Pending DE2213753A1 (de) | 1971-03-31 | 1972-03-22 | Bis-styryltriazole, deren Verwendung zum optischen Aufhellen von organischen Materialien und Verfahren zu deren Herstellung |
| DE19722213895 Pending DE2213895A1 (de) | 1971-03-31 | 1972-03-22 | Styryl-v-triazole, deren Verwendung zum optischen Aufhellen von organischen Materialien und Verfahren zu deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722213895 Pending DE2213895A1 (de) | 1971-03-31 | 1972-03-22 | Styryl-v-triazole, deren Verwendung zum optischen Aufhellen von organischen Materialien und Verfahren zu deren Herstellung |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH554389A (enExample) |
| DE (2) | DE2213753A1 (enExample) |
| FR (2) | FR2131661A5 (enExample) |
| GB (3) | GB1352089A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3926969A (en) * | 1972-11-24 | 1975-12-16 | Sandoz Ltd | Triazole-bis(benzoxazole) optical brighteners |
| US8772487B2 (en) * | 2008-01-24 | 2014-07-08 | Life Technologies Corporation | Fluorogenic hydrazine-substituted compounds |
| KR20250127750A (ko) * | 2022-12-23 | 2025-08-26 | 미요시 유시 가부시끼가이샤 | 자외선 흡수제 |
-
1971
- 1971-03-31 CH CH470071A patent/CH554389A/xx not_active IP Right Cessation
- 1971-03-31 CH CH470371A patent/CH554392A/xx not_active IP Right Cessation
-
1972
- 1972-03-20 GB GB1289172A patent/GB1352089A/en not_active Expired
- 1972-03-20 GB GB1289272A patent/GB1353133A/en not_active Expired
- 1972-03-22 DE DE19722213753 patent/DE2213753A1/de active Pending
- 1972-03-22 DE DE19722213895 patent/DE2213895A1/de active Pending
- 1972-03-24 GB GB1404472A patent/GB1360135A/en not_active Expired
- 1972-03-27 FR FR7210696A patent/FR2131661A5/fr not_active Expired
- 1972-03-27 FR FR7210693A patent/FR2131658A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1353133A (en) | 1974-05-15 |
| CH554392A (de) | 1974-09-30 |
| DE2213895A1 (de) | 1972-10-05 |
| GB1360135A (en) | 1974-07-17 |
| FR2131661A5 (enExample) | 1972-11-10 |
| CH554389A (de) | 1974-09-30 |
| GB1352089A (en) | 1974-05-15 |
| FR2131658A5 (enExample) | 1972-11-10 |
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