CH411224A - Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel - Google Patents

Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel

Info

Publication number: CH411224A
Authority: CH; Switzerland
Prior art keywords: methanol; parts; radical; toluenesulfone; water
Prior art date: 1959-01-16

Application number

CH613362A

Other languages

German (de)

English (en)

Inventor

Roderich Dr Raue

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1959-01-16

Filing date

1959-12-17

Publication date

1966-04-15

1959-12-17 Application filed by Bayer Ag filed Critical Bayer Ag

1966-04-15 Publication of CH411224A publication Critical patent/CH411224A/de

Links

230000003287 optical effect Effects 0.000 title claims description 5
238000005282 brightening Methods 0.000 title description 4
150000001893 coumarin derivatives Chemical class 0.000 title 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
239000004753 textile Substances 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical group 0.000 claims description 3
239000000835 fiber Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
238000005956 quaternization reaction Methods 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
239000002253 acid Substances 0.000 claims 2
230000008018 melting Effects 0.000 claims 2
238000002844 melting Methods 0.000 claims 2
MPQHFGWCQDCSEA-UHFFFAOYSA-N CO.S(=O)(=O)(OCC)OCC Chemical compound CO.S(=O)(=O)(OCC)OCC MPQHFGWCQDCSEA-UHFFFAOYSA-N 0.000 claims 1
125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
125000004494 ethyl ester group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
LXWDKUDDSFJARM-UHFFFAOYSA-N iodomethane;methanol Chemical compound OC.IC LXWDKUDDSFJARM-UHFFFAOYSA-N 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
150000004775 coumarins Chemical class 0.000 description 4
229920002239 polyacrylonitrile Polymers 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000009987 spinning Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
230000002087 whitening effect Effects 0.000 description 3
ACMLKANOGIVEPB-UHFFFAOYSA-N 2-oxo-2H-chromene-3-carboxylic acid Chemical class C1=CC=C2OC(=O)C(C(=O)O)=CC2=C1 ACMLKANOGIVEPB-UHFFFAOYSA-N 0.000 description 2
229940105325 3-dimethylaminopropylamine Drugs 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
FYOZSKRVTISLHE-UHFFFAOYSA-N ethyl 3-oxobenzo[f]chromene-2-carboxylate Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)OCC)=C3C=CC2=C1 FYOZSKRVTISLHE-UHFFFAOYSA-N 0.000 description 2
VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
229940013085 2-diethylaminoethanol Drugs 0.000 description 1
PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
RMHHFZIWCLXRTA-UHFFFAOYSA-N 3-oxobenzo[f]chromene-2-carboxylic acid Chemical compound C1=CC=C2C(C=C(C(O3)=O)C(=O)O)=C3C=CC2=C1 RMHHFZIWCLXRTA-UHFFFAOYSA-N 0.000 description 1
QCTOLMMTYSGTDA-UHFFFAOYSA-N 4-(dimethylamino)butan-1-ol Chemical compound CN(C)CCCCO QCTOLMMTYSGTDA-UHFFFAOYSA-N 0.000 description 1
UDMURVSWYOLZAU-UHFFFAOYSA-N 7-(dimethylamino)-2-oxochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)OC2=CC(N(C)C)=CC=C21 UDMURVSWYOLZAU-UHFFFAOYSA-N 0.000 description 1
VEEGNDSSWAOLFN-UHFFFAOYSA-N 7-methoxy-2-oxochromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)OC2=CC(OC)=CC=C21 VEEGNDSSWAOLFN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000005266 casting Methods 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003599 detergent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000155 melt Substances 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
-1 oxethyl Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000047 product Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920002994 synthetic fiber Polymers 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
- C09B57/02—Coumarine dyes
- 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
- C07D311/12—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 3 and unsubstituted in position 7
- 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
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Plural Heterocyclic Compounds (AREA)
Detergent Compositions (AREA)

CH613362A 1959-01-16 1959-12-17 Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel CH411224A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF27490A DE1205941B (de)	1959-01-16	1959-01-16	Optische Aufhellungsmittel

Publications (1)

Publication Number	Publication Date
CH411224A true CH411224A (de)	1966-04-15

Family

ID=7092471

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH613362A CH411224A (de)	1959-01-16	1959-12-17	Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel
CH8191759A CH400991A (de)	1959-01-16	1959-12-17	Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH8191759A CH400991A (de)	1959-01-16	1959-12-17	Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel

Country Status (5)

Country	Link
BE (1)	BE586593A (fr)
CH (2)	CH411224A (fr)
DE (1)	DE1205941B (fr)
FR (1)	FR1245885A (fr)
GB (1)	GB908784A (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE498447A (fr) *	1949-10-05
US2683720A (en) *	1949-12-15	1954-07-13	Endo Products Inc	Process for the preparation of 6-nitro-coumarin-3-carboxylic acid
DE937822C (de) *	1952-05-28	1956-01-19	Bayer Ag	Optische Bleichmittel

1959
- 1959-01-16 DE DEF27490A patent/DE1205941B/de active Pending
- 1959-12-17 CH CH613362A patent/CH411224A/de unknown
- 1959-12-17 CH CH8191759A patent/CH400991A/de unknown
1960
- 1960-01-13 GB GB131360A patent/GB908784A/en not_active Expired
- 1960-01-15 BE BE586593A patent/BE586593A/fr unknown
- 1960-01-16 FR FR815845A patent/FR1245885A/fr not_active Expired

Also Published As

Publication number	Publication date
CH400991A (de)	1965-07-15
BE586593A (fr)	1960-05-03
GB908784A (en)	1962-10-24
FR1245885A (fr)	1960-11-10
DE1205941B (de)	1965-12-02

Publication	Publication Date	Title
EP0029003B1 (fr)	1984-12-05	Sels d'agents de blanchiment optique cationiques, leur préparation et leur utilisation sur des matières organiques ainsi que leurs solutions aqueuses concentrées
DE1963065A1 (de)	1970-07-02	Neue Bis-(triazinylamino)-stilbene
DE2301495C3 (de)	1975-11-20	Grün-gelbe kationische Farbstoffe und Verfahren zu ihrer Herstellung
CH411224A (de)	1966-04-15	Verwendung von Cumarinabkömmlingen als optische Aufhellungsmittel
CH500982A (de)	1970-12-31	Verfahren zur Herstellung von 3-Phenyl-7-amino-carbostyril-Verbindungen
DE1670873C3 (de)	1979-01-11	Pyrazolyl-triazolyl-cumarine
DE2921641C2 (fr)	1988-03-10
DE1105375B (de)	1961-04-27	Optische Aufheller
DE2011552C3 (de)	1980-01-24	3- P'^'-Dichtör-^-afkyl-imenyrJ^ A2 -pyrazoint-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als optische Aufheller
EP0011824A1 (fr)	1980-06-11	Benzofurannyl-benzimidazoles, procédé pour leur préparation et leur application pour le blanchiment optique de matériaux organiques
US3075996A (en)	1963-01-29	Brightening agents
DE1594851C3 (de)	1976-02-26	Aufhellungsmittel
AT235234B (de)	1964-08-10	Optische Aufhellungsmittel
DE1719005C3 (de)	1976-11-04	2-(4'-Carboxystyryl)-benzoxazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als optische Aufheller
AT233507B (de)	1964-05-11	Optische Aufhellungsmittel
AT212326B (de)	1960-12-12	Verfahren zur Herstellung von neuen, basisch substituierten Azepinderivaten
AT235279B (de)	1964-08-25	Verfahren zur Herstellung neuer 5-Nitrofurfuryliden-hydrazine
CH356435A (de)	1961-08-31	Verfahren zur Herstellung eines optischen Aufhellungsmittels
DE1770961A1 (de)	1972-01-13	Triazinylaminocumarinverbindungen
DE825548C (de)	1951-12-20	Verfahren zur Herstellung von neuen diquartaeren Salzen von Pyrimidylaminocinnolinen
AT226702B (de)	1963-04-10	Verfahren zur Herstellung von neuen Flavon-7-oxy-essigsäureamiden
DE1518088C (de)	1971-07-15	Saureanlagerungssalze des 2 Guanidino methyl 1,4 benzodioxans sowie Verfahren zu ihrer Herstellung
AT215944B (de)	1961-06-26	Optisch aufhellende Stoffe
CH377775A (de)	1964-02-14	Verwendung von p-Cumarinyl-(3)-phenylcarbaminsäurederivaten als Aufhellungsmittel
DE1282591B (de)	1968-11-14	Optische Aufhellungsmittel