US3843718A - 1,4-bis-styryl-benzene-dioxyalkanoic acids,salts and esters - Google Patents

1,4-bis-styryl-benzene-dioxyalkanoic acids,salts and esters Download PDF

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Publication number
US3843718A
US3843718A US00230931A US23093172A US3843718A US 3843718 A US3843718 A US 3843718A US 00230931 A US00230931 A US 00230931A US 23093172 A US23093172 A US 23093172A US 3843718 A US3843718 A US 3843718A
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Prior art keywords
carbon atoms
alkyl
formula
compounds
groups
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Expired - Lifetime
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US00230931A
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English (en)
Inventor
C Luethi
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Novartis AG
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Ciba Geigy AG
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Priority claimed from CH323571A external-priority patent/CH556888A/de
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Priority to US472391A priority Critical patent/US3927119A/en
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Publication of US3843718A publication Critical patent/US3843718A/en
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Classifications

    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/74—Unsaturated compounds containing —CHO groups
    • 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
    • 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
    • D06L4/65—Optical bleaching or brightening with mixtures of optical brighteners
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture

Definitions

  • R and R are identical or different and de- 260/465 F, 260/512 R, 260/512 C, 260/520, note alkyl with five to 18 carbon atoms, substituted 260/544 M, 260/559 B, 260/600, 260/606.5 alkyl with a total of two to 20 carbon atoms, or alke- P, 260/613 R, 260/951 nyl with three to four carbon atoms, X and X are [51] Int. Cl.
  • C070 69/76 identical or different and denote hydrogen, alkoxy
  • References Cited denote hydrogen, halogen, alkenyl with three to four UMTED STATES PATENTS carbon atoms or alkyl with one to four carbon atoms. 3,755,446 8/1973 Scheuermann @1111.
  • R a represents hydrogen halogen alkoxy one to four carbon atoms or alkyl with one to four carbon atoms, and the parapositions are free of alkoxy groups FOREIGN PATENTS OR APPLICATIONS 1 Or and gmups- 1,576,018 6/1969 France 3 Claims, No Drawings 1,4-BIS-STXRXLQENZEljE-DIOXYALKANOIC wherein R denotes alkyl with to 18 carbon atoms, al-
  • ACIDS, SALTS AND ESTERS kenyl with 3 to 4 carbon atoms or a substituted alkyl The new compounds are useful as optical brightengroup with a total of 2 to 12 carbon atoms, of which the ers. substituents can be phenyl, phenyl substituted by lower
  • the present invention relates to new bis-stilbene 5 alkyl or halogen, carboxyl, including its salts, carbalkcompounds, their use as optical brighteners, and prooxy or carbophenoxy, carbonamido with an optionally Deads for their manufacture.
  • temperatures between about and 100C are in general used, especially if dimethylformamide or dimethylsulphoxide are em ployed as solvents.
  • the preferred temperature range is to 60C.
  • higher temperatures can also be employed if this is desired for reasons of time saving or if a less active but cheaper condensation agent is to be employed.
  • reaction temperatures in the range of 10 to 180C are thus also possible.
  • the treatment in a neutral or alkaline or acid bath.
  • the treatment is usually carried out at temperatures of about to I 140C, for example at the boiling point of the bath or near it (about 90C).
  • Solutions or emulsions in organic solvents can also be used for the finishing, according to the invention, of textile substrates, as is practised in the dyeing trade in so-called solvent dyeing padthermofix application, or exhaustion dyeing processes in dyeing machines).
  • dyestuffs shadeing
  • pigments coloured pigments especially, for example, white pigments
  • dye baths printing pastes, discharge pastes or reserve pastes, or for the aftertreatment of dyeings, prints or discharge prints.
  • a bis-stilbene compound of the formula X1 X2 W Q R 0 0 R2 a a g 26.7 g of ethyl acetate, 2 g of a reaction accelerator and EXAMPLE 28 An intimate mixture of 100 parts of polyvinyl chloride, 3 parts of stabiliser (Advastat ED 100: Ba/Cd complex), 2 parts of titanium dioxide, 59 parts of dioctyl phthalate and 0.01 to 0.2 part of the compound of the formula (43) are milled on a calender at 150 to 155C to give a sheet.
  • the opaque polyvinyl chloride sheet thus obtained has a substantially higher degree of whiteness than a sheet which does not contain the optical brightener.
  • R, and R each independently is (CH ),,COOM where n is an integer from 1 to 3 and M is hydrogen, sodium potassium, ammonium or alkyl of 1 to 8 carbon atoms,
  • a is hydrogen, halogen, or alkyl or alkoxy of one to four carbon atoms
  • X, and X each independently is hydrogen, alkoxy of one to four carbon atoms, halogen, alkenyl of three to four carbon atoms or alkyl of one to four carbon atoms,
  • Y, and Y each independently is hydrogen, halogen, alkenyl of three to four carbon atoms, or alkyl of one to four carbon atoms,
  • a bis-stilbene compound according to claim 2 in which X,, X Y, and Y each is hydrogen, and
  • R, and R each is CH,),,COOM
  • n is an integer from 1 to 3 and M is hydrogen, sodium, potassium, ammonium or alkyl of one to eight carbon atoms.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US00230931A 1971-03-05 1972-03-01 1,4-bis-styryl-benzene-dioxyalkanoic acids,salts and esters Expired - Lifetime US3843718A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US472391A US3927119A (en) 1971-03-05 1974-05-22 Bis-stilbene compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH323571A CH556888A (de) 1971-03-05 1971-03-05 Verfahren zum optischen aufhellen ausserhalb der textilindustrie von organischen materialien.
CH160872 1972-02-03

Publications (1)

Publication Number Publication Date
US3843718A true US3843718A (en) 1974-10-22

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Family Applications (1)

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US00230931A Expired - Lifetime US3843718A (en) 1971-03-05 1972-03-01 1,4-bis-styryl-benzene-dioxyalkanoic acids,salts and esters

Country Status (11)

Country Link
US (1) US3843718A (en, 2012)
JP (1) JPS5638625B1 (en, 2012)
BE (1) BE780173A (en, 2012)
CA (1) CA994357A (en, 2012)
DD (1) DD99627A5 (en, 2012)
DE (1) DE2209128C3 (en, 2012)
ES (1) ES400439A1 (en, 2012)
FR (1) FR2128543B1 (en, 2012)
GB (1) GB1350883A (en, 2012)
IT (1) IT952084B (en, 2012)
NL (1) NL7202870A (en, 2012)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984399A (en) * 1967-10-03 1976-10-05 Ciba-Geigy Ag Bis-stilbene compounds
EP0001991A1 (de) * 1977-11-04 1979-05-30 Ciba-Geigy Ag Phosphoniumverbindungen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von unsymmetrisch substituierten Stilbenaufhellern
US4264330A (en) * 1977-05-16 1981-04-28 Dieter Schmidt Method of visualizing the flow pattern of a fluid using optically active, radioactive or chemically active particles of desired density
US4314820A (en) * 1979-04-11 1982-02-09 Ciba-Geigy Corporation Distyrylbenzene fluorescent brightening agents
US4339393A (en) * 1979-04-11 1982-07-13 Ciba-Geigy Corporation Distyrylbiphenyls
US4371475A (en) * 1977-05-04 1983-02-01 Showa Kagaku Kogyo Company, Ltd. 1,4-Bis-styryl-benzene derivatives and a process for the preparation of the same
US20100190105A1 (en) * 2007-05-25 2010-07-29 Agfa Graphics Nv Lithographic printing plate precursor

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3061269D1 (en) 1979-06-29 1983-01-13 Wellcome Found Substituted phenol ethers, their preparation, intermediates therefor, pharmaceutical compositions containing them and the preparation thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH500145A (de) * 1967-07-14 1970-12-15 Ciba Geigy Ag Verfahren zur Herstellung aromatischer, Äthylendoppelbindungen enthaltender Verbindungen
CH505036A (de) * 1968-12-23 1971-03-31 Ciba Geigy Ag Verfahren zur Herstellung von neuen Bis-stilben-Verbindungen

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984399A (en) * 1967-10-03 1976-10-05 Ciba-Geigy Ag Bis-stilbene compounds
US4371475A (en) * 1977-05-04 1983-02-01 Showa Kagaku Kogyo Company, Ltd. 1,4-Bis-styryl-benzene derivatives and a process for the preparation of the same
US4264330A (en) * 1977-05-16 1981-04-28 Dieter Schmidt Method of visualizing the flow pattern of a fluid using optically active, radioactive or chemically active particles of desired density
EP0001991A1 (de) * 1977-11-04 1979-05-30 Ciba-Geigy Ag Phosphoniumverbindungen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von unsymmetrisch substituierten Stilbenaufhellern
US4314820A (en) * 1979-04-11 1982-02-09 Ciba-Geigy Corporation Distyrylbenzene fluorescent brightening agents
US4339393A (en) * 1979-04-11 1982-07-13 Ciba-Geigy Corporation Distyrylbiphenyls
US4468352A (en) * 1979-04-11 1984-08-28 Ciba-Geigy Corporation Distyrylbiphenyls
US4602087A (en) * 1979-04-11 1986-07-22 Ciba-Geigy Corporation Distyrylbiphenyls
US20100190105A1 (en) * 2007-05-25 2010-07-29 Agfa Graphics Nv Lithographic printing plate precursor
US8445176B2 (en) * 2007-05-25 2013-05-21 Agfa Graphics Nv Lithographic printing plate precursor

Also Published As

Publication number Publication date
GB1350883A (en) 1974-04-24
DE2209128C3 (de) 1981-10-22
DE2209128A1 (de) 1972-09-14
FR2128543B1 (en, 2012) 1974-04-05
IT952084B (it) 1973-07-20
NL7202870A (en, 2012) 1972-09-07
FR2128543A1 (en, 2012) 1972-10-20
DE2209128B2 (en, 2012) 1981-01-08
BE780173A (fr) 1972-09-04
CA994357A (en) 1976-08-03
ES400439A1 (es) 1975-06-16
DD99627A5 (en, 2012) 1973-08-12
JPS5638625B1 (en, 2012) 1981-09-08

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