GB1360490A - 3- 3,4, - dichloro -6,- alkylphenyl - delta2 - pyrazoline deriva tives and a process for their manufacture - Google Patents

3- 3,4, - dichloro -6,- alkylphenyl - delta2 - pyrazoline deriva tives and a process for their manufacture

Info

Publication number
GB1360490A
GB1360490A GB2381571*A GB2381571A GB1360490A GB 1360490 A GB1360490 A GB 1360490A GB 2381571 A GB2381571 A GB 2381571A GB 1360490 A GB1360490 A GB 1360490A
Authority
GB
United Kingdom
Prior art keywords
dichloro
optionally substituted
prepared
double bond
compound
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
GB2381571*A
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
Priority claimed from DE2011552A external-priority patent/DE2011552C3/en
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB1360490A publication Critical patent/GB1360490A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Coloring (AREA)

Abstract

1360490 Pyrazolines FARBWERKE HOECHST AG 19 April 1971 [11 March 1970] 23815/71 Heading C2C [Also in Division C5] Compounds of formula wherein R is a C 1 -C 4 alkyl group, R<SP>1</SP> is hydrogen or an optionally substituted pheny group, and X is an ethylenically unsaturated radical or an optionally substituted saturated aliphatic radical are prepared by one or more of (a) condensation of a 3,4-dichloro-6-R-phenylketone with a hydrazinophenyl sulphone, (b) esterification of a hydroxyalkyl sulphone, (c) splitting of an ester group formed in (b), optionally without isolation, to form a double bond, (d) hydrogenation of a double bond formed in (c), (e) additive saturation of a double bond formed in (c) by reaction with a compound having at least one active hydrogen atom, (f) quaternization of an amino compound formed in (e), or (g) conversion of a compound wherein X is a hydroxy group to the corresponding sulphinic acid salt and reacting this with an optionally substituted alkyl halide or with an epoxide. The products are optical brightening agents. 3,4 - Dichloro - 6 - R- or 6 - H - acetophenones, propiophenones and #-chloro-propiophenones are prepard by Friedel-Crafts acylation. The sodium salt of 2-sulphostyryl-3<SP>1</SP>,4<SP>1</SP>-dichloro- 6<SP>1</SP>-methyl-phenyl ketone is prepared by reaction of 3,4-dichloro-6-methyl-acetophenone with the sodium salt of benzaldehyde-2-sulphonic acid. 2,4-Dichloro-n-propyl-benzene is prepared by reduction of 2,4-dichloro-propiophenone. The compounds of Formula I are used as optical brighteners for polymers, which may be added before or after polymerization. In an example, an acrylonitrile copolymer containing a brightener is spun from DMF solution.
GB2381571*A 1970-03-11 1971-04-19 3- 3,4, - dichloro -6,- alkylphenyl - delta2 - pyrazoline deriva tives and a process for their manufacture Expired GB1360490A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2011552A DE2011552C3 (en) 1970-03-11 1970-03-11 3- P '^' - Dichtör - ^ - afkyl-imenyrJ ^ A2 -pyrazoint derivatives, process for their preparation and their use as optical brighteners

Publications (1)

Publication Number Publication Date
GB1360490A true GB1360490A (en) 1974-07-17

Family

ID=5764794

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2381571*A Expired GB1360490A (en) 1970-03-11 1971-04-19 3- 3,4, - dichloro -6,- alkylphenyl - delta2 - pyrazoline deriva tives and a process for their manufacture

Country Status (17)

Country Link
JP (2) JPS5632313B1 (en)
AT (1) AT315803B (en)
BE (1) BE764127A (en)
CA (1) CA971959A (en)
CH (2) CH569755A5 (en)
CS (1) CS152391B2 (en)
ES (1) ES388953A1 (en)
FR (1) FR2084476A5 (en)
GB (1) GB1360490A (en)
HU (1) HU162981B (en)
NL (1) NL163212C (en)
NO (1) NO131596C (en)
PL (1) PL83038B1 (en)
RO (1) RO61307A (en)
SE (1) SE378105B (en)
YU (1) YU34550B (en)
ZA (1) ZA711514B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988346A (en) * 1974-06-18 1976-10-26 Sandoz Ltd. Pyrazoline compounds useful as optical brighteners
US4036851A (en) 1974-01-29 1977-07-19 Sandoz Ltd. 1,3-Diphenyl substituted pyrazolines
US7300474B2 (en) 2002-02-28 2007-11-27 Clariant Produkte (Deutschland) Gmbh Aqueous liquid formulations of pyrazoline brighteners

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49134675A (en) * 1973-03-02 1974-12-25
JPS6291600A (en) * 1985-10-08 1987-04-27 モベイ・コ−ポレ−シヨン Detergent

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036851A (en) 1974-01-29 1977-07-19 Sandoz Ltd. 1,3-Diphenyl substituted pyrazolines
US3988346A (en) * 1974-06-18 1976-10-26 Sandoz Ltd. Pyrazoline compounds useful as optical brighteners
US7300474B2 (en) 2002-02-28 2007-11-27 Clariant Produkte (Deutschland) Gmbh Aqueous liquid formulations of pyrazoline brighteners

Also Published As

Publication number Publication date
CA971959A (en) 1975-07-29
NL7102967A (en) 1971-09-14
JPS591750B2 (en) 1984-01-13
SU439991A3 (en) 1974-08-15
ZA711514B (en) 1972-04-26
YU58971A (en) 1979-02-28
HU162981B (en) 1973-05-28
JPS56138173A (en) 1981-10-28
PL83038B1 (en) 1975-12-31
CH559273A (en) 1975-02-28
NO131596B (en) 1975-03-17
ES388953A1 (en) 1975-03-16
CH569755A5 (en) 1975-11-28
CH343771A4 (en) 1974-07-15
NO131596C (en) 1975-06-25
CS152391B2 (en) 1973-12-19
SE378105B (en) 1975-08-18
RO61307A (en) 1976-09-15
NL163212B (en) 1980-03-17
FR2084476A5 (en) 1971-12-17
JPS5632313B1 (en) 1981-07-27
NL163212C (en) 1980-08-15
BE764127A (en) 1971-09-13
AT315803B (en) 1974-06-10
YU34550B (en) 1979-09-10

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years