GB890519A - Process for the manufacture of coloured materials of high molecular weight - Google Patents

Process for the manufacture of coloured materials of high molecular weight

Info

Publication number
GB890519A
GB890519A GB399759A GB399759A GB890519A GB 890519 A GB890519 A GB 890519A GB 399759 A GB399759 A GB 399759A GB 399759 A GB399759 A GB 399759A GB 890519 A GB890519 A GB 890519A
Authority
GB
United Kingdom
Prior art keywords
benzene
azo
dyestuffs
isocyanate
dyestuff
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
GB399759A
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.)
BASF Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB890519A publication Critical patent/GB890519A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/68—Unsaturated polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/714—Monoisocyanates or monoisothiocyanates containing nitrogen in addition to isocyanate or isothiocyanate nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7856—Nitrogen containing azo groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6858—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

In a process for the manufacture of coloured polyurethanes by the polyaddition of an aromatic polyisocyanate with a polyhydroxylated aliphatic compound, or of coloured polyesters by the polymerization of a mixture of styrene with a condensation product of an unsaturated polycarboxylic acid and a polyhydroxyl compound, there is added before or during the polyaddition or polymerization a dyestuff which contains an isocyanate group and is free from groups imparting solubility in water. The dyestuffs may contain substituents such as halogen atoms or alkyl, alkoxy, nitro or carbalkoxy groups. Dyestuffs of the anthraquinone and benzene-azo-benzene, benzene-azo-pyrazolone, benzene-azo-acetoacetic acid arylide and benzene-azo-naphthalene series are mentioned. They may be added in admixture with benzene, toluene or nitrobenzene. The coloured materials obtained, if brought into a finely-divided form, are useful as pigments. In Examples (1) an adipic acid-glycol polyester, 2,4- and 2,6-tolylene diisocyanates and a toluene solution of azobenzene-4-isocyanate are mixed. There is then added a mixture of water, polyglycol ether and ethylmorpholine, a yellow polyurethane foam being obtained. A similar product was obtained using benzene-azo-naphthylisocyanate-(1:4) as dyestuff. p-Acetylamino-azo-benzene was used in a comparison experiment; (2) a plate is cast from a mixture of an unsaturated polyester from maleic acid and glycols, styrene, and a azobenzene-4-isocyanate and hardened at 100 DEG C. Benzene-azo-naphthylisocyanate-(1:4) can be used similarly; (3) a lacquer is prepared from the polyester specified in Example (1), toluene 2:4-and 2:6-diisocyanates and benzene-azo-naphthylisocyanate-(1:4) in toluene.ALSO:Azo dyestuffs containing an isocyanate group and free from groups importing water-solubility can be obtained by heating the hydrochloride of the appropriate dyestuff containing an amino group with phosgene in an inert solvent or by condensing equimolecular proportions of a monoamino dyestuff and of a diisocyanate. The dyestuffs may contain halogen atoms or alkyl alkoxy nitro or carbalkoxy groups. By the first method are prepared azobenzene-4-isocyanate benzene-azo-naphthyl-isocyanate-(1 : 4) and dyestuffs of the formulae <FORM:0890519/IV (c)/1> By the second method a dyestuff is prepared by reacting p-aminobenzene and 2,4-tolylene diisocyanate. Reference is also made to benzeneazo-pyrazolone and benzene-azo-acetoacetic acid arylide dyestuffs containing NCO groups. The dyestuffs are used for preparing coloured polyurethanes and polyesters, which, finely divided, are useful as pigments.ALSO:In a process for the manufacture of coloured polyurethanes (including foams) by the reaction of an aromatic polyisocyanate with a polyhydrooxylated aliphatic compound, there is added before or during the reaction a dyestuff which contains an isocyanate group and is free from groups imparting solubility in water. The dyestuffs may contain substituents such as halogen atoms or alkyl, alkoxy, nitro or carbalkoxy groups. Dyestuffs of the anthraquinone and benzene-azo-benzene, benzene-azo-pyrazolone, benzene-azo-acetoacetic acid arylide and benzene-azo-naphthalene series are mentioned. They may be added in admixture with benzene, toluene or nitrobenzene. In Example 1,1 a yellow foamed polyurethane is obtained by reacting an adipic acid-glycol polyester, 2,4-and 2,6-tolylene diisocyanates, a toluene solution of azobenzene-4-isocyanate and a mixture of water, polyglycol ether and N-ethyl morpholine. Benzene-azo-naphthyl isocyanate-(1 : 4) can also be used as the dyestuff p-acetylamino-azo-benzene is used in a comparison experiment.
GB399759A 1958-02-06 1959-02-04 Process for the manufacture of coloured materials of high molecular weight Expired GB890519A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH5554458A CH378536A (en) 1958-02-06 1958-02-06 Process for the production of colored high molecular weight substances

Publications (1)

Publication Number Publication Date
GB890519A true GB890519A (en) 1962-02-28

Family

ID=4519955

Family Applications (1)

Application Number Title Priority Date Filing Date
GB399759A Expired GB890519A (en) 1958-02-06 1959-02-04 Process for the manufacture of coloured materials of high molecular weight

Country Status (3)

Country Link
CH (1) CH378536A (en)
FR (1) FR1220879A (en)
GB (1) GB890519A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0511572A1 (en) * 1991-05-01 1992-11-04 Wolff Walsrode Aktiengesellschaft Amine and ammonium isocyanates, method of preparation, their use in preparing ammonium group containing polymers and the polymers thus prepared

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0511572A1 (en) * 1991-05-01 1992-11-04 Wolff Walsrode Aktiengesellschaft Amine and ammonium isocyanates, method of preparation, their use in preparing ammonium group containing polymers and the polymers thus prepared
US5310849A (en) * 1991-05-01 1994-05-10 Wolff Walsrode Ag Amino and ammonium isocyanates, a process for their preparation, their use for the production of polymers containing ammonium groups and the polymers thus produced

Also Published As

Publication number Publication date
FR1220879A (en) 1960-05-30
CH378536A (en) 1964-06-15

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