GB1152875A - Coumarin Derivatives and their use as Optical Whitening Agents - Google Patents

Coumarin Derivatives and their use as Optical Whitening Agents

Info

Publication number
GB1152875A
GB1152875A GB42223/66A GB4222366A GB1152875A GB 1152875 A GB1152875 A GB 1152875A GB 42223/66 A GB42223/66 A GB 42223/66A GB 4222366 A GB4222366 A GB 4222366A GB 1152875 A GB1152875 A GB 1152875A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
group
reaction
cyano group
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
Application number
GB42223/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hickson and Welch Ltd
Original Assignee
Hickson and Welch Ltd
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.)
Filing date
Publication date
Application filed by Hickson and Welch Ltd filed Critical Hickson and Welch Ltd
Priority to GB42223/66A priority Critical patent/GB1152875A/en
Priority to US666997A priority patent/US3525753A/en
Priority to BE703813D priority patent/BE703813A/xx
Priority to FR120960A priority patent/FR1540028A/en
Priority to DE1643410A priority patent/DE1643410C3/en
Priority to CH1298867A priority patent/CH494309A/en
Priority to CH1298867D priority patent/CH1298867A4/xx
Priority to NL6712791A priority patent/NL6712791A/xx
Publication of GB1152875A publication Critical patent/GB1152875A/en
Expired legal-status Critical Current

Links

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)
  • Coloring (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,152,875. Coumarin derivatives. HICKSON & WELCH Ltd. 4 Sept., 1967 [21 Sept., 1966], No. 42223/66. Heading C2C. [Also in Division D1] Compounds of the formula wherein R 1 is hydrogen or alkyl and R 2 is alkyl. which alkyl groups may be substituted by non- ionogenic and non-colour producing substituents, may be obtained (i) by reaction of a compound of formula wherein X is cyano or a group, e.g. a nitro group, which is convertible to a cyano group, with an appropriate alkylating agent (e.g. a dialkyl sulphate or iodide), and where necessary converting the group X to a cyano group; (ii) by reaction of a compound of formula with a compound of formula or a functional derivative thereof, and where necessary converting the group X to a cyano group; or (iii) by reaction of a compound of formula with a diazonium compound of formula and where necessary converting the group X to a cyano group. The above compounds of Formula (II) employed as starting materials may be obtained by (a) reaction of a compound of formula with a compound of Formula IV or a functional derivative thereof; (b) by reaction of a compound of formula with a diazonium compound of Formula (VI) or (c) when R 1 represents hydrogen, by heating α - (41 - cyanophenyl) - # - (2<SP>11</SP>,4<SP>11</SP> - dimethoxyphenyl) acrylonitrile in the presence of an anhydrous Friedel-Crafts catalyst; the α-(4<SP>1</SP>- cyanophenyl) - # - (2<SP>11</SP>,4<SP>11</SP> - dimethoxyphenyl) acrylonitrile may be prepared by reaction of p-cyanobenzyl cyanide with 2,4-dimethoxybenzaldehyde. Specific examples describe the preparation of compounds of the above Formula (I) wherein R 1 is hydrogen and R 2 is methyl, ethyl or isopropyl. The products are stated to be useful as optical whitening agents.
GB42223/66A 1966-09-21 1966-09-21 Coumarin Derivatives and their use as Optical Whitening Agents Expired GB1152875A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB42223/66A GB1152875A (en) 1966-09-21 1966-09-21 Coumarin Derivatives and their use as Optical Whitening Agents
US666997A US3525753A (en) 1966-09-21 1967-09-11 Coumarin derivatives having optical whitening properties
BE703813D BE703813A (en) 1966-09-21 1967-09-13
FR120960A FR1540028A (en) 1966-09-21 1967-09-14 New optical brighteners
DE1643410A DE1643410C3 (en) 1966-09-21 1967-09-15 3- (4'-Cyanophenyl) coumarin derivatives and processes for their preparation, and textile treatment agents containing these compounds
CH1298867A CH494309A (en) 1966-09-21 1967-09-18 Process for the optical brightening of synthetic textile fibers, means for carrying out the process and application of the process
CH1298867D CH1298867A4 (en) 1966-09-21 1967-09-18
NL6712791A NL6712791A (en) 1966-09-21 1967-09-19

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB42223/66A GB1152875A (en) 1966-09-21 1966-09-21 Coumarin Derivatives and their use as Optical Whitening Agents

Publications (1)

Publication Number Publication Date
GB1152875A true GB1152875A (en) 1969-05-21

Family

ID=10423400

Family Applications (1)

Application Number Title Priority Date Filing Date
GB42223/66A Expired GB1152875A (en) 1966-09-21 1966-09-21 Coumarin Derivatives and their use as Optical Whitening Agents

Country Status (6)

Country Link
US (1) US3525753A (en)
BE (1) BE703813A (en)
CH (2) CH1298867A4 (en)
DE (1) DE1643410C3 (en)
GB (1) GB1152875A (en)
NL (1) NL6712791A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103773361B (en) * 2014-02-25 2015-04-22 山东大学 Cysteine fluorescence probe adopting coumarin as fluorophore and application of cysteine fluorescence probe

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3351482A (en) * 1961-02-21 1967-11-07 Bayer Ag Synthetic textiles brightened with 3-phenyl-7-hydroxy-coumarin

Also Published As

Publication number Publication date
DE1643410B2 (en) 1973-05-03
CH1298867A4 (en) 1970-04-15
BE703813A (en) 1968-03-13
CH494309A (en) 1970-04-15
DE1643410C3 (en) 1973-12-06
US3525753A (en) 1970-08-25
NL6712791A (en) 1968-03-22
DE1643410A1 (en) 1972-02-03

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee