GB908784A - Coumarin derivative brightening agents - Google Patents
Coumarin derivative brightening agentsInfo
- Publication number
- GB908784A GB908784A GB131360A GB131360A GB908784A GB 908784 A GB908784 A GB 908784A GB 131360 A GB131360 A GB 131360A GB 131360 A GB131360 A GB 131360A GB 908784 A GB908784 A GB 908784A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- nhconh
- nhco
- aralkyl
- 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
- 238000005282 brightening Methods 0.000 title abstract 2
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229960000956 coumarin Drugs 0.000 abstract 2
- 235000001671 coumarin Nutrition 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 2
- 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 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 238000009987 spinning Methods 0.000 abstract 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)
- Detergent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Prior to spinning fibres therefrom, a solution of polyacrylonitrile in dimethylformamide is admixed with a coumarin brightening agent of the formula:- <FORM:0908784/IV(a)/1> or a quaternary derivative thereof, wherein A represents a phenylene or naphthylene radical which may be optionally substituted (e.g. by hydroxyl, halogen, alkyl, -O-alkyl, -O-aralkyl, -NH2, -NH-alkyl, -N-(alkyl)2, -NHCO-alkyl, -NHCO-aryl, -NHCONH-alkyl or -NHCONH-aryl), R represents hydrogen or C1-3 alkyl, Y represents O or NH, R1 represents alkylene and R2 and R3 represent alkyl or aralkyl.ALSO:The invention comprises quarternary ammonium derivatives of coumarin compounds of the formula: <FORM:0908784/IV (b)/1> wherein A represents a phenylene or naphthylene radical which may be optionally substituted (e.g. by hydroxyl, halogen, alkyl, -O-alkyl, -O-aralkyl, -NH2, -NH-alkyl, - N - (alkyl)2, - NHCO - alkyl, - NHCO - aryl, -NHCONH-alkyl or -NHCONH-aryl), R represents hydrogen or C1-3 alkyl, Y represents O or NH, R1 represents alkylene and R2 and R3 represent alkyl or aralkyl. The compounds are prepared by reacting a coumarin-3-carboxylic acid derivative of the formula:- <FORM:0908784/IV (b)/2> wherein X is halogen, an -O-alkyl group or a free hydroxyl group with an amine of the formula: H-Y-R1-N R2 R3, and subsequently quarternating the resulting products of the above general formula with a quarternating agent such as dimethyl or diethyl sulphate, methyl or ethyl iodide, 4-toluenesulphonic acid methyl or ethyl ester or benzyl chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF27490A DE1205941B (en) | 1959-01-16 | 1959-01-16 | Optical brighteners |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB908784A true GB908784A (en) | 1962-10-24 |
Family
ID=7092471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB131360A Expired GB908784A (en) | 1959-01-16 | 1960-01-13 | Coumarin derivative brightening agents |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE586593A (en) |
| CH (2) | CH411224A (en) |
| DE (1) | DE1205941B (en) |
| FR (1) | FR1245885A (en) |
| GB (1) | GB908784A (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE498447A (en) * | 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 (en) * | 1952-05-28 | 1956-01-19 | Bayer Ag | Optical bleach |
-
1959
- 1959-01-16 DE DEF27490A patent/DE1205941B/en active Pending
- 1959-12-17 CH CH613362A patent/CH411224A/en unknown
- 1959-12-17 CH CH8191759A patent/CH400991A/en unknown
-
1960
- 1960-01-13 GB GB131360A patent/GB908784A/en not_active Expired
- 1960-01-15 BE BE586593A patent/BE586593A/en unknown
- 1960-01-16 FR FR815845A patent/FR1245885A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1205941B (en) | 1965-12-02 |
| FR1245885A (en) | 1960-11-10 |
| CH400991A (en) | 1965-07-15 |
| BE586593A (en) | 1960-05-03 |
| CH411224A (en) | 1966-04-15 |
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