GB1163851A - Derivatives of 1,4-[bis-benzoxazolyl-(2')]-naphthalene and the use thereof as optical brighteners - Google Patents

Derivatives of 1,4-[bis-benzoxazolyl-(2')]-naphthalene and the use thereof as optical brighteners

Info

Publication number
GB1163851A
GB1163851A GB260667A GB260667A GB1163851A GB 1163851 A GB1163851 A GB 1163851A GB 260667 A GB260667 A GB 260667A GB 260667 A GB260667 A GB 260667A GB 1163851 A GB1163851 A GB 1163851A
Authority
GB
United Kingdom
Prior art keywords
acid
formula
benzoxazolyl
naphthalene
ester
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
GB260667A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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.)
Filing date
Publication date
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1163851A publication Critical patent/GB1163851A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
    • C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,163,851. Derivatives of bis(benzoxazolyl)- naphthalene. FARBWERKE HOECHST A.G. 18 Jan., 1967 [18 Jan., 1966 (2)], No. 2606/67. Heading C2C. [Also in Divisions C3 and Dl] The invention comprises asymmetrical benzoxazole compounds of the formula wherein R 1-4 each represents hydrogen or a C 1-4 alkyl group, the substitutents in each benzoxazole moiety being different. The compounds are prepared by condensing the acid chloride of an acid of the Formula II with an o-aminophenol of the formula and heating the amide intermediate of the formula at a temperature above 200‹ C. in a high-boiling solvent under an atmosphere of an inert gas, if desired in the presence of an acidic catalyst, e.g. ZnCl 2 , p-toluene sulphonic acid. The asymmetrical benzoxazoles are used as optical brighteners. The acid reactants of the Formula II are prepared by converting the dimethyl ester of naphthalene-1,4-dicarboxylic acid to the monomethyl ester by partial hydrolysis, treating the half ester with thionyl chloride to form the acid chloride, condensing the acid chloride with an o-aminophenol to give an intermediate amide which is cyclized by heating to the appropriate 4-[benzoxazolyl-(2<SP>1</SP>)]-1-naphthoic acid methyl ester from which the free acid is obtained by hydrolysis.
GB260667A 1966-01-18 1967-01-18 Derivatives of 1,4-[bis-benzoxazolyl-(2')]-naphthalene and the use thereof as optical brighteners Expired GB1163851A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEF0048191 1966-01-18
DEF48189A DE1302052B (en) 1966-01-18 1966-01-18 Optical brighteners

Publications (1)

Publication Number Publication Date
GB1163851A true GB1163851A (en) 1969-09-10

Family

ID=25977081

Family Applications (1)

Application Number Title Priority Date Filing Date
GB260667A Expired GB1163851A (en) 1966-01-18 1967-01-18 Derivatives of 1,4-[bis-benzoxazolyl-(2')]-naphthalene and the use thereof as optical brighteners

Country Status (5)

Country Link
BE (1) BE692823A (en)
CH (3) CH478880A (en)
DE (1) DE1302052B (en)
FR (1) FR1508560A (en)
GB (1) GB1163851A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3993659A (en) 1971-08-10 1976-11-23 Ciba-Geigy Corporation Bis-benzoxazolyl-naphthalenes as optical brighteners
US4245007A (en) * 1975-10-10 1981-01-13 Ciba-Geigy Corporation 1,4-Bis-[azol-2'-yl]-naphthalenes and process of using the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3993659A (en) 1971-08-10 1976-11-23 Ciba-Geigy Corporation Bis-benzoxazolyl-naphthalenes as optical brighteners
US4245007A (en) * 1975-10-10 1981-01-13 Ciba-Geigy Corporation 1,4-Bis-[azol-2'-yl]-naphthalenes and process of using the same

Also Published As

Publication number Publication date
FR1508560A (en) 1968-01-05
CH478880A (en) 1969-09-30
DE1302052B (en) 1969-11-13
CH55467A4 (en) 1970-11-13
BE692823A (en) 1967-07-18
CH503829A (en) 1970-11-13

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee