DE877755C - Verfahren zur Herstellung von neuen Fluoreszenzmitteln der Stilbenreihe - Google Patents
Verfahren zur Herstellung von neuen Fluoreszenzmitteln der StilbenreiheInfo
- Publication number
- DE877755C DE877755C DEP46935A DEP0046935A DE877755C DE 877755 C DE877755 C DE 877755C DE P46935 A DEP46935 A DE P46935A DE P0046935 A DEP0046935 A DE P0046935A DE 877755 C DE877755 C DE 877755C
- Authority
- DE
- Germany
- Prior art keywords
- stilbene
- acid
- new
- chloride
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 8
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000007850 fluorescent dye Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- -1 acylated aminostilbene sulfonic Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000004744 fabric Substances 0.000 description 6
- VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZRSGZIMDIHBXIN-UHFFFAOYSA-N 1,3-benzodioxole-5-carbonyl chloride Chemical compound ClC(=O)C1=CC=C2OCOC2=C1 ZRSGZIMDIHBXIN-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- XVROZAJDEFRSQQ-UHFFFAOYSA-N 3,4-dihydroxybenzoyl chloride Chemical compound OC1=CC=C(C(Cl)=O)C=C1O XVROZAJDEFRSQQ-UHFFFAOYSA-N 0.000 description 2
- KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 2
- DWSUJONSJJTODA-UHFFFAOYSA-N 5-(chloromethyl)-1,3-benzodioxole Chemical group ClCC1=CC=C2OCOC2=C1 DWSUJONSJJTODA-UHFFFAOYSA-N 0.000 description 2
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 2
- REJHVSOVQBJEBF-UHFFFAOYSA-N DSD-acid Natural products OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000009994 optical bleaching Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JQNBCSPQVSUBSR-UHFFFAOYSA-N 2,3-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1OC JQNBCSPQVSUBSR-UHFFFAOYSA-N 0.000 description 1
- KCYKWOJPTQVXJT-UHFFFAOYSA-N 2,4-dibutoxybenzoyl chloride Chemical compound CCCCOC1=CC=C(C(Cl)=O)C(OCCCC)=C1 KCYKWOJPTQVXJT-UHFFFAOYSA-N 0.000 description 1
- YARKPRSRXZGKNI-UHFFFAOYSA-N 2,5-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(OC)C(C(Cl)=O)=C1 YARKPRSRXZGKNI-UHFFFAOYSA-N 0.000 description 1
- BIEFDNUEROKZRA-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline Chemical class NC1=CC=CC=C1C=CC1=CC=CC=C1 BIEFDNUEROKZRA-UHFFFAOYSA-N 0.000 description 1
- RZCCJXPBBDSEOO-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-carboxyphenyl)ethenyl]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C=CC1=CC=C(N)C(C(O)=O)=C1 RZCCJXPBBDSEOO-UHFFFAOYSA-N 0.000 description 1
- CZXHDWYXINPKFH-UHFFFAOYSA-N 2-amino-5-[2-(4-amino-3-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1C=CC1=CC=C(N)C(S(O)(=O)=O)=C1 CZXHDWYXINPKFH-UHFFFAOYSA-N 0.000 description 1
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 1
- FTHPLWDYWAKYCY-UHFFFAOYSA-N 3,5-dimethoxybenzoyl chloride Chemical compound COC1=CC(OC)=CC(C(Cl)=O)=C1 FTHPLWDYWAKYCY-UHFFFAOYSA-N 0.000 description 1
- ZTGKHKPZSMMHNM-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-disulfonic acid Chemical class OS(=O)(=O)C1=CC=CC(C=CC=2C=CC=CC=2)=C1S(O)(=O)=O ZTGKHKPZSMMHNM-UHFFFAOYSA-N 0.000 description 1
- BKKCHPZQDBOJLI-UHFFFAOYSA-N 3-amino-6-[2-(4-aminophenyl)ethenyl]cyclohexa-2,4-diene-1,1-disulfonic acid Chemical compound NC1=CC(C(C=C1)C=CC1=CC=C(C=C1)N)(S(=O)(=O)O)S(=O)(=O)O BKKCHPZQDBOJLI-UHFFFAOYSA-N 0.000 description 1
- RMNIMTZIXJZZLR-UHFFFAOYSA-N 3-benzamido-6-(2-phenylethenyl)benzene-1,2-disulfonic acid Chemical class C(C1=CC=CC=C1)(=O)NC1=C(C(=C(C=C1)C=CC1=CC=CC=C1)S(=O)(=O)O)S(=O)(=O)O RMNIMTZIXJZZLR-UHFFFAOYSA-N 0.000 description 1
- HSWXDJWJBYPPFZ-UHFFFAOYSA-N 5-amino-2-[2-(4-aminophenyl)ethenyl]benzoic acid Chemical class NC=1C=C(C(=CC=1)C=CC1=CC=C(C=C1)N)C(=O)O HSWXDJWJBYPPFZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OEYBFBRYHZLUOI-UHFFFAOYSA-N NC1=CC(S(O)(=O)=O)=C(C=CC(C(S(O)(=O)=O)=CC(N)=C2)=C2S(O)(=O)=O)C(S(O)(=O)=O)=C1 Chemical compound NC1=CC(S(O)(=O)=O)=C(C=CC(C(S(O)(=O)=O)=CC(N)=C2)=C2S(O)(=O)=O)C(S(O)(=O)=O)=C1 OEYBFBRYHZLUOI-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OLWMSXPKBVMLAD-UHFFFAOYSA-N n-[4-[2-(4-benzamidophenyl)ethenyl]phenyl]benzamide Chemical class C=1C=CC=CC=1C(=O)NC(C=C1)=CC=C1C=CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 OLWMSXPKBVMLAD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004753 textile 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
- C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US660868XA | 1948-06-26 | 1948-06-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE877755C true DE877755C (de) | 1953-05-26 |
Family
ID=22067170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP46935A Expired DE877755C (de) | 1948-06-26 | 1949-06-25 | Verfahren zur Herstellung von neuen Fluoreszenzmitteln der Stilbenreihe |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE489832A (enExample) |
| DE (1) | DE877755C (enExample) |
| GB (1) | GB660868A (enExample) |
| NL (1) | NL147211B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838504A (en) * | 1955-04-21 | 1958-06-10 | Sterling Drug Inc | Benzimidazolylstilbene whitening and brightening agents |
-
0
- BE BE489832D patent/BE489832A/fr unknown
-
1949
- 1949-06-08 GB GB15291/49A patent/GB660868A/en not_active Expired
- 1949-06-25 DE DEP46935A patent/DE877755C/de not_active Expired
- 1949-06-25 NL NL696913879A patent/NL147211B/xx not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2838504A (en) * | 1955-04-21 | 1958-06-10 | Sterling Drug Inc | Benzimidazolylstilbene whitening and brightening agents |
| US2937148A (en) * | 1955-04-21 | 1960-05-17 | Sterling Drug Inc | Detergent compositions comprising benzimidazolylstilbene whitening and brightening agents |
Also Published As
| Publication number | Publication date |
|---|---|
| GB660868A (en) | 1951-11-14 |
| NL147211B (nl) | 1953-01-15 |
| BE489832A (enExample) |
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