GB846148A - A process for fluorescent brightening fibres and fibrous materials - Google Patents

A process for fluorescent brightening fibres and fibrous materials

Info

Publication number
GB846148A
GB846148A GB6625/57A GB662557A GB846148A GB 846148 A GB846148 A GB 846148A GB 6625/57 A GB6625/57 A GB 6625/57A GB 662557 A GB662557 A GB 662557A GB 846148 A GB846148 A GB 846148A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aryl
group
fibres
naphthaldehyde
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
GB6625/57A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB846148A publication Critical patent/GB846148A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • 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
    • C07C45/72—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Artificial Filaments (AREA)
  • Pyrrole Compounds (AREA)
  • Coloring (AREA)

Abstract

Fibrous materials of animal or vegetable origin or synthetic fibrous materials are treated with a fluorescent non-colouring methine compound of the formula: <FORM:0846148/IV(a)/1> where X is an aromatic or heterocyclic radical, R1 is an acyl or a carboxyl group which may be esterified, a carbonamide group which may be alkyl, aryl or aralkyl substituted or a cyano group and R2 is an alkyl, cycloalkyl, aryl, acyl or carboacyl group which may be esterified or an alkyl, aryl or aralkyl substituted carbonamide or cyano group when X is a mono nuclear aromatic radical and may also be hydrogen when X is a polynuclear aromatic or heterocyclic radical, and n is 1 or 2. X may be phenyl, naphthyl, indolyl, carbazolyl, or thienyl and when aromatic may be substituted by hydroxyl, alkoxy, alkyl, aryl, aralkyl or acyl groups halogen atoms or nitro or cyano groups, sulphonic acid or carboxyl groups which may be esterified or carbonamide or sulphonamide groups which may be alkyl, aryl or aralkyl substituted. The compounds may be added to spinning solutions. The materials which may be treated include fibres of polyesters, polyamides, polyurethanes, polyacrylonitrile, polystyrene or cellulose. Water-soluble compounds may be applied to natural fibres and insoluble or barely soluble compounds to the synthetic fibres. In examples, (1) polyacrylonitrile fibres are treated with an aqueous bath containing a paraffin sulphonate to which has been added a solution of a -(2-hydroxynaphthyl-1)-ethyleneb -cyanocarboxylic acid-methylamide in alcohol and the bath is heated to boiling; (7) polyacrylonitrile fibres are treated with a bath brought to the boil and containing a surface active paraffin sulphonate, oxalic acid and benzene-1, 4-bis-(ethylene-a ,a -dicarboxylic acid-diethylester); (8) a solution in dimethyl formamide of b -(2-hydroxynaphthyl-1)-ethylene-a -cyano-a -carbonamide is added to a cellulose acetate/acetone spinning solution; (9) b -(2-hydroxynaphthyl-1)-ethylene-a , a -dicarbonamide is added to granulated polystyrene, optionally with titanium dioxide and is shaped in an injection moulding machine. Examples (5) and (6) also illustrate the treatment of polyacrylonitrile fibres.ALSO:Fluorescent non-colouring methine compounds of the formula: <FORM:0846148/IV(b)/1> where X is a heterocyclic or aromatic radical, for example an indolyl, carbazolyl or thienyl radical, or a phenyl or naphthyl radical which may be substituted by hydroxyl, alkoxy, alkyl, aryl, aralkyl or acyl groups, halogen atoms, nitro, dimethylamino or cyano groups, sulphonic acid or carboxyl groups which may be esterified, or carbonamide or sulphonamide groups which may be alkyl, aryl or aralkyl substituted, R1 is an acyl group, a carboxyl group which may be esterified, a carbonamide group which may be alkyl, aryl or aralkyl substituted or a cyano group, R2 is an alkyl, cycloalkyl, aryl or acyl group, a carboxyl group which may be esterified, an alkyl, aryl or aralkyl substituted carbonamide group or a cyano group when X is a mononuclear aromatic radical and may also be hydrogen when X is a polynuclear aromatic or heterocyclic radical, and n is 1 or 2, are prepared by reacting an aromatic or heterocyclic aldehyde with a compound containing an active methylene group in the presence of an alkaline condensing agent. A solvent or diluent such as alcohol or benzene may be present. Aldehydes specified are 3- or 5-chloro-salicylaldehyde, N-ethylcarbazole-3-aldehyde, 2-thiophene aldehyde, 3:5-dichlor-salicylaldehyde, 4-diemethylamino-salicylaldehyde, 4-hydroxybenzaldehyde, aldehydo-cresotic acids, anisaldehyde, 2-hydroxy-1-naphthaldehyde, 3, 6 or 7-chloro-2-hydroxy-1-naphthaldehyde, 3 or 6-methoxy-2-hydroxy-1-naphthaldehyde, 2:6-dihydroxy-naphthalene-1:5-dialdehyde, 1-hydroxy-2-naphthaldehyde, 1- hydroxy-4-methoxy-2-naphthaldehyde, 1-hydroxy-4-chloro-2-naphthaldehyde, 1-hydroxy-4-bromo-2-naphthaldehyde, 2-methoxy-1-naphthaldehyde, 2-ethoxy-1-naphthaldehyde, benzaldehyde, 4-chlorobenzaldehyde, 3-nitrobenzaldehyde, terephthaldehyde, 1-naphthaldehyde, and 1-methyl-2-phenylindole-3-aldehyde. The active-methylene-group containing substances specified include malonic acid, cyanacetic acid, acetoacetic acid and their esters, amides, anilides, alkyl-, aralkyl- or cyclo-alkyl-amides, acetone, acetyl acetone, acetophenone, benzyl cyanide and malonic acid dinitrile. In an example 2-hydroxy-1-naphthaldehyde and cyanacetmethylamide are dissolved in alcohol, pyridine is added dropwise and the mixture heated to boiling to give as a reaction product b -(2-hydroxynaphthyl-1)-ethylene-a -cyano-a -carbonic acid-methylamide.ALSO:Fibrous materials of animal or vegetable origin or synthetic fibrous materials are treated with a fluorescent non-colouring methine compound of the formula: <FORM:0846148/IV (c)/1> where X is an aromatic or heterocyclic radical, R1 is an acyl or a carboxyl group which may be esterified, a carbonamide group which may be alkyl, aryl or aralkyl substituted or a cyano group and R2 is an alkyl, cycloalkyl, aryl, acyl or carboacyl group which may be esterified or an alkyl, aryl or aralkyl substituted carbonamide or cyano group when X is a mono nuclear aromatic radical and may also be hydrogen when X is a polynuclear aromatic or heterocyclic radical, and n is 1 or 2. X may be phenyl, naphthyl, indolyl, carbazolyl, or thienyl and when aromatic may be substituted by hydroxyl, alkoxy, alkyl, aryl, aralkyl or acyl groups halogen atoms or nitro or cyano groups, sulphonic acid or carboxyl groups which may be esterified or carbonamide or sulphonamide groups which may be alkyl, aryl or aralkyl substituted. The compounds may be applied in aqueous or organic solutions or dispersions which may contain washing agents. The materials which may be treated include fibres of polyesters, polyamides, polyurethanes, polyacrylonitrile polystrene or cellulose. Watersoluble compounds may be applied to natural fibres and insoluble or barely soluble compounds to the synthetic fibres. In examples, (1) polyacrylonitrile fibres are treated with an aqueous bath containing a paraffin sulphonate to which has been added a solution of b -(2-hydroxynaphthyl-1)-ethylene-a -cyano-a -carboxylic acid-methylamide in alcohol and the bath is heated to boiling; (2) e caprolactam fibres are treated in an aqueous bath at 30 DEG to 70 DEG C. containing oleyl alcohol sulphonate, and a dispersion prepared by grinding b -(2-hydroxynaphthyl-1)-a , a -dicyanethylene with formaldehyde-hydroxynaphthalene sulphonic acid; (4) polyester fibres are treated with an aqueous bath heated to boiling and containing formic acid, oleyl alcohol sulphonate and to which a solution of b -(2-hydroxy-naphthyl-1)-ethylene -a -cyan #s -a -carbonamide in dimethyl formamide has been added; (7) polyacrylonitrile fibres are treated with a bath brought to the boil and containing a surface active paraffin sulphonate, oxalic acid and benzene-1, 4-bis-(ethylenea , a -dicarboxylic aciddiethylester).
GB6625/57A 1956-03-01 1957-02-27 A process for fluorescent brightening fibres and fibrous materials Expired GB846148A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF19663A DE1010047B (en) 1956-03-01 1956-03-01 Whitening agents

Publications (1)

Publication Number Publication Date
GB846148A true GB846148A (en) 1960-08-24

Family

ID=7089398

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6625/57A Expired GB846148A (en) 1956-03-01 1957-02-27 A process for fluorescent brightening fibres and fibrous materials

Country Status (6)

Country Link
BE (1) BE555326A (en)
CH (2) CH360047A (en)
DE (1) DE1010047B (en)
FR (1) FR1185438A (en)
GB (1) GB846148A (en)
NL (2) NL214984A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3254046A (en) * 1963-06-24 1966-05-31 Monsanto Co Spin dyeing of polyacrylonitrile fibers with 1-30 parts per million of polymethine and triarylmethane dyes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL124588C (en) * 1959-04-08
JP2846091B2 (en) * 1990-09-25 1999-01-13 オリヱント化学工業株式会社 Indole compounds and their uses

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3254046A (en) * 1963-06-24 1966-05-31 Monsanto Co Spin dyeing of polyacrylonitrile fibers with 1-30 parts per million of polymethine and triarylmethane dyes

Also Published As

Publication number Publication date
NL214984A (en)
FR1185438A (en) 1959-07-31
NL105255C (en)
CH360047A (en) 1962-02-15
DE1010047B (en) 1957-06-13
CH366391A (en) 1962-12-31
BE555326A (en)

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