EP0540471B1 - Compound and process for the production of good quality moulded articles - Google Patents

Compound and process for the production of good quality moulded articles Download PDF

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Publication number
EP0540471B1
EP0540471B1 EP92810821A EP92810821A EP0540471B1 EP 0540471 B1 EP0540471 B1 EP 0540471B1 EP 92810821 A EP92810821 A EP 92810821A EP 92810821 A EP92810821 A EP 92810821A EP 0540471 B1 EP0540471 B1 EP 0540471B1
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Prior art keywords
hydrogen
formula
phenyl
alkyl
process according
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German (de)
French (fr)
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EP0540471A1 (en
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Manfred Dr. Rembold
Claude Dr. Eckhardt
Peter Dr. Nesvadba
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Novartis AG
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Ciba Geigy AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65131—Compounds containing ether or acetal groups
    • 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
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • 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
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D06L4/621—Optical bleaching or brightening in aqueous solvents with anionic brighteners
    • 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
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D06L4/629—Optical bleaching or brightening in aqueous solvents with cationic brighteners
    • 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
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D06L4/636—Optical bleaching or brightening in aqueous solvents with disperse brighteners
    • 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
    • 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
    • D06L4/671—Optical brightening assistants, e.g. enhancers or boosters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65112—Compounds containing aldehyde or ketone groups
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber
    • Y10S8/925—Aromatic polyamide
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/93—Pretreatment before dyeing
    • Y10S8/931—Washing or bleaching

Description

Die vorliegende Erfindung betrifft ein Mittel und ein Verfahren zur Herstellung von polyamidfaserhaltigen hochweissen oder besonders farbbrillanten Artikeln mit verbesserten Mouldingechtheiten.The present invention relates to an agent and a method for the production of polyamide fiber-containing bright white or particularly brilliant color articles with improved fastness to molding.

Gewisse Artikel aus Kunstfasern werden durch thermische Behandlung geformt (Moulding). Es handelt sich vor allem um hochwertige Artikel aus optisch aufgehellten Polyamidfasern, oder auch solche, welche aus Polyamid/Polyurethan bestehen. Die heissen Pressformen verursachen in der Regel eine bestimmte Vergilbung oder gar Verbräunung des optisch aufgehellten Textilmaterials. Diese Erscheinung ist stark von der Polyamidqualität, aber vor allem von dem optischen Aufheller abhängig, und führt zu Schwankungen in der Produktequalität solcher Artikel.Certain articles made of synthetic fibers are shaped by thermal treatment (molding). These are primarily high-quality items made from optically brightened polyamide fibers, or items made from polyamide / polyurethane. The hot press molds usually cause a certain yellowing or even browning of the optically brightened textile material. This appearance is strongly dependent on the polyamide quality, but above all on the optical brightener, and leads to fluctuations in the product quality of such articles.

Es wurde nun gefunden, dass bei der Verwendung bestimmter Benzofuran-2-on-Verbindungen und üblicher optischer Aufheller, sowie auch in Verbindung mit Farbstoffen die obigen Nachteile ganz oder zumindest in grossem Masse beseitigt werden können. Überraschenderweise erhält man so eine Ware, welche nach dem Moulding im Vergleich zum nur optisch aufgehellten Material einen höheren Weissgrad, eine höhere Farbbrillanz und ausserdem geringere Qualitätsschwankungen aufweist.It has now been found that when using certain benzofuran-2-one compounds and conventional optical brighteners, and also in conjunction with dyes, the above disadvantages can be eliminated entirely or at least to a large extent. Surprisingly, you get a product that, after molding, has a higher degree of whiteness, a higher color brilliance and also lower quality fluctuations compared to the only optically brightened material.

Die Erfindung betrifft daher sowohl die Verwendung bzw. ein Verfahren unter Verwendung von Benzofuran-2-on-Verbindungen zur Verbesserung der Mouldingechtheit von polyamidfaserhaltigem Material als auch ein Mittel zum optischen Aufhellen von polyamidfaserhaltigem Artikeln, welches einen optischen Aufheller und ein Benzofuran-2-on enthält, sowie ein Mittel, das neben dem Benzofuran-2-on und dem optischen Aufheller noch einen oder mehrere Farbstoffe enthält.The invention therefore relates both to the use and a method using benzofuran-2-one compounds to improve the fastness to molding of polyamide fiber-containing material and to a means for optically brightening articles containing polyamide fiber, which has an optical brightener and a benzofuran-2-one contains, as well as an agent that contains one or more dyes in addition to the benzofuran-2-one and the optical brightener.

Das Verfahren zur Herstellung von polyamidfaserhaltigen Artikeln mit verbesserten Mouldingeigenschaften ist dadurch gekennzeichnet, dass man vor, während oder nach dem optischen Aufhellen und gegebenenfalls Färben der Faser eine Verbindung der Formel (1)

Figure imgb0001
worin

R₁
Phenyl unsubstituiert oder substituiert, worin die Substituenten 1 bis 3 Alkylreste mit zusammen höchstens 18 Kohlenstoffatomen, C₁-C₁₂-Alkoxy, C₁-C₁₈-Acyloxy, C₁-C₁₈-Alkoxycarbonyl, Chlor oder eine Mischung aus diesen Substituenten sind,
R₂
Wasserstoff oder C₁-C₄-Alkyl,
R₄
Wasserstoff, C₁-C₁₂-Alkyl, gegebenenfalls durch C₁-C₄-Alkyl substituiertes C₅-C₇-Cycloalkyl, Phenyl, C₇-C₁₂-Phenylalkyl oder Chlor ist,
R₃
die Bedeutung von R₂ oder R₄ hat oder ein Rest der Formel
Figure imgb0002
Figure imgb0003
Figure imgb0004
Figure imgb0005
 oder -D-E ist, worin
n
0, 1 oder 2,
R₆
Wasserstoff, C₁-C₁₈-Alkyl, durch Sauerstoff oder Schwefel unterbrochenes C₂-C₁₈-Alkyl, Dialkylaminoalkyl mit insgesamt 3 bis 16 Kohlenstoffatomen, Cyclopentyl, Cyclohexyl, Phenyl oder mit 1 bis 3 Alkylresten mit zusammen höchstens 18 Kohlenstoffatomen substituiertes Phenyl ist,
die Substituenten R₇
unabhängig voneinander Wasserstoff, C₁-C₁₈-Alkyl, Cyclopentyl, Cyclohexyl, Phenyl, mit 1 oder 2 Alkylresten mit zusammen höchstens 16 Kohlenstoffatomen substituiertes Phenyl, ein Rest der Formel -C₂H₄OH, -C₂H₄-O-CmH2m+1 oder
Figure imgb0006
 sind oder zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Piperidin- oder Morpholinrest bilden,
m
1 bis 18,
R₁₀
Wasserstoff, C₁-C₂₂-Alkyl oder C₅-C₁₂-Cycloalkyl,
A
ein gegebenenfalls durch Stickstoff, Sauerstoff oder Schwefel unterbrochenes Alkylen mit 2 bis 22 Kohlenstoffatomen,
R₈
Wasserstoff, C₁-C₁₈-Alkyl, Cyclopentyl, Cyclohexyl, Phenyl, mit 1 oder 2 Alkylresten mit zusammen höchstens 16 Kohlenstoffatomen substituiertes Phenyl oder Benzyl,
R₉
C₁-C₁₈-Alkyl,
D
-O-, -S-, -SO-, -SO₂- oder -C(R₁₁)₂- ist,
die Substituenten R₁₁
unabhängig voneinander Wasserstoff, Alkyl mit zusammen höchstens 16 Kohlenstoffatomen, Phenyl oder ein Rest der Formel
Figure imgb0007
 sind, worin n, R₆ und R₇ die angegebenen Bedeutungen haben,
E
ein Rest der Formel
Figure imgb0008
 worin R₁, R₂ und R₄ die angegebenen Bedeutungen haben, und
R₅
Wasserstoff, C₁-C₃₀-Alkyl, Cyclopentyl, Cyclohexyl, Chlor oder ein Rest der Formel
Figure imgb0009
 ist, worin R₆ und R₇ die angegebenen Bedeutungen haben, oder
R₅
zusammen mit R₄ einen Tetramethylenrest bildet,
auf die Faser aufbringt.The process for the production of polyamide fiber-containing articles with improved molding properties is characterized in that before, during or after the optical brightening and optionally dyeing of the fiber, a compound of Formula 1)
Figure imgb0001
 wherein
R₁
Phenyl unsubstituted or substituted, in which the substituents are 1 to 3 alkyl radicals with a total of at most 18 carbon atoms, C₁-C₁₂ alkoxy, C₁-C₁ Ac acyloxy, C₁-C₁₈ alkoxycarbonyl, chlorine or a mixture of these substituents,
R₂
Hydrogen or C₁-C₄ alkyl,
R₄
Is hydrogen, C₁-C₁₂-alkyl, optionally substituted by C₁-C₄-alkyl C durch-C₇-cycloalkyl, phenyl, C₇-C₁₂-phenylalkyl or chlorine,
R₃
has the meaning of R₂ or R₄ or a radical of the formula
Figure imgb0002
Figure imgb0003
Figure imgb0004
Figure imgb0005
 or -DE is where
n
0, 1 or 2,
R₆
Is hydrogen, C₁-C₁₈ alkyl, C₂-C₁₈ alkyl interrupted by oxygen or sulfur, dialkylaminoalkyl with a total of 3 to 16 carbon atoms, cyclopentyl, cyclohexyl, phenyl or with 1 to 3 alkyl radicals with a total of at most 18 carbon atoms substituted phenyl,
the substituents R₇
independently of one another hydrogen, C₁-C₁₈-alkyl, cyclopentyl, cyclohexyl, phenyl, with 1 or 2 alkyl radicals with a maximum of 16 carbon atoms substituted phenyl, a radical of the formula -C₂H₄OH, -C₂H₄-OC m H 2m + 1 or
Figure imgb0006
 are or together with the Nitrogen atom to which they are attached form a piperidine or morpholine residue,
m
1 to 18,
R₁₀
Hydrogen, C₁-C₂₂-alkyl or C₅-C₁₂-cycloalkyl,
A
an alkylene with 2 to 22 carbon atoms which may be interrupted by nitrogen, oxygen or sulfur,
R₈
Hydrogen, C₁-C₁₈-alkyl, cyclopentyl, cyclohexyl, phenyl, with 1 or 2 alkyl radicals with a total of at most 16 carbon atoms substituted phenyl or benzyl,
R₉
C₁-C₁₈ alkyl,
D
Is -O-, -S-, -SO-, -SO₂- or -C (R₁₁) ₂-,
the substituents R₁₁
independently of one another hydrogen, alkyl with a maximum of 16 carbon atoms, phenyl or a radical of the formula
Figure imgb0007
 are in which n, R₆ and R₇ have the meanings given,
E
a rest of the formula
Figure imgb0008
 wherein R₁, R₂ and R₄ have the meanings given, and
R₅
Hydrogen, C₁-C₃₀ alkyl, cyclopentyl, cyclohexyl, chlorine or a radical of the formula
Figure imgb0009
 is in which R₆ and R₇ have the meanings given, or
R₅
forms a tetramethylene residue together with R₄,
onto the fiber.

Die Benzofuran-2-one der Formel (1) und Verfahren zur ihrer Herstellung sowie ihre Verwendung zum Stabilisieren von polymeren organischen Materialien gegen thermischen, photooxidativen oder thermomechanischen Abbau sind in US-A-4,325,863, US-A-4,338,244 und EP-A-0 415 887 beschrieben.The benzofuran-2-ones of the formula (1) and processes for their preparation and their use for stabilizing polymeric organic materials against thermal, photooxidative or thermomechanical degradation are described in US Pat. Nos. 4,325,863, 4,338,244 and EP-A- 0 415 887.

Bedeuten die Substituenten in der Formel (1) Alkyl, so können bis zu 30 Kohlenstoffatome enthalten. Beispiele hierfür sind Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tetradecyl, Hexadecyl, Octadecyl, Eicosyl oder Docosyl sowie entsprechende verzweigte Isomere, insbesondere tert.-Butyl, i-Octyl und i-Dodecyl. Alkoxy- und Alkoxycarbonylreste leiten sich von diesen Gruppen ab ebenso wie Alkylenreste, die in den Definitionen der in Formel (1) gezeigten Substituenten enthalten sind. Die aufgezählten Alkylreste können durch Sauerstoff oder Schwefel unterbrochen sein, um insbesondere Struktureinheiten wie -CH₂CH₂-O-CH₂CH₂-, -CH₂CH₂-S-CH₂CH₂- oder -O-(CH₂)₆-O- zu bilden. Sind die Alkylreste Substituenten an Phenylringen, so besetzen sie vorzugsweise die 3- und 5-Stellung.If the substituents in the formula (1) are alkyl, they can contain up to 30 carbon atoms. Examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, Octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl or docosyl and corresponding branched isomers, in particular tert-butyl, i-octyl and i-dodecyl. Alkoxy and alkoxycarbonyl radicals are derived from these groups, as are alkylene radicals which are contained in the definitions of the substituents shown in formula (1). The enumerated alkyl radicals can be interrupted by oxygen or sulfur to form structural units such as -CH₂CH₂-O-CH₂CH₂-, -CH₂CH₂-S-CH₂CH₂- or -O- (CH₂) ₆-O-. If the alkyl radicals are substituents on phenyl rings, they preferably occupy the 3- and 5-positions.

In bevorzugt verwendeten Benzofuran-2-onen ist der Substituent R₂ in den Verbindungen der Formel (1) Wasserstoff.In preferably used benzofuran-2-ones, the substituent R₂ in the compounds of formula (1) is hydrogen.

R₃ ist vorzugsweise Wasserstoff, C₁-C₁₂-Alkyl, Cyclopentyl, Cyclohexyl, Chlor oder ein Rest der Formel

Figure imgb0010
oder -D-E, worin n, R₆, R₇, D und E die angegebenen Bedeutungen haben.R₃ is preferably hydrogen, C₁-C₁₂ alkyl, cyclopentyl, cyclohexyl, chlorine or a radical of the formula
Figure imgb0010
 or -DE, where n, R₆, R₇, D and E have the meanings given.

Bevorzugt bedeutet R₆ Wasserstoff, C₁-C₁₈-Alkyl, Cyclopentyl oder Cyclohexyl.R₆ is preferably hydrogen, C₁-C₁₈ alkyl, cyclopentyl or cyclohexyl.

In einer weiteren Gruppe bevorzugt verwendeter Benzofuran-2-one bedeutet R₁ Phenyl unsubstituiert oder substituiert, worin die Substituenten 1 oder 2 Alkylreste mit zusammen höchstens 12 Kohlenstoffatomen, C₁-C₁₂-Acyloxy oder eine Mischung aus diesen Substituenten sind.

R₂
ist Wasserstoff und R₄ ist Wasserstoff oder C₁-C₁₂-Alkyl,
R₃
ist Wasserstoff, C₁-C₁₂-Alkyl,
Figure imgb0011
 oder -D-E,
R₅
Wasserstoff, C₁-C₂₀-Alkyl,
Figure imgb0012
 oder
R₅
ist zusammen mit R₄ Tetramethylen, und n, R₆, R₇, D und E haben die angegebenen Bedeutungen.
In a further group of preferably used benzofuran-2-one, R₁ is phenyl unsubstituted or substituted, where the substituents are 1 or 2 alkyl radicals with a maximum of 12 carbon atoms, C₁-C₁₂ acyloxy or a mixture of these substituents.
R₂
is hydrogen and R₄ is hydrogen or C₁-C₁₂ alkyl,
R₃
is hydrogen, C₁-C₁₂ alkyl,
Figure imgb0011
 or -DE,
R₅
Hydrogen, C₁-C₂₀ alkyl,
Figure imgb0012
 or
R₅
is together with R₄ tetramethylene, and n, R₆, R₇, D and E have the meanings given.

Hiervon bevorzugt werden solche Verbindungen der Formel (1), worin

R₁
Phenyl oder
Figure imgb0013
 worin R₄₀,R₄₁ und R₄₂ unabhängig voneinander Wasserstoff oder C₁-C₈-Alkyl,
R₃
Wasserstoff, C₁-C₁₂-Alkyl oder -D-E,
R₂
Wasserstoff,
R₄
Wasserstoff oder C₁-C₄-Alkyl, und
R₅
C₁-C₂₀-Alkyl ist,
wobei D und E die angegebenen Bedeutungen haben, und insbesondere jene Verbindungen, worin
R₁
Phenyl oder
Figure imgb0014
 worin R₄₀,R₄₁ und R₄₂ unabhängig voneinander Wasserstoff oder C₁-C₄-Alkyl,
R₃
C₁-C₄-Alkyl oder -D-E,
R₂ und R₄
Wasserstoff, und
R₅
C₁-C₄-Alkyl oder Cyclopentyl oder Cyclohexyl ist, wobei D -C(R₁₁)₂- und E ein Rest der Formel
Figure imgb0015
ist, wobei die Substituenten R₁₁ gleich oder verschieden voneinander sind und je C₁-C₄-Alkyl sind, und R₁, R₂, R₄ und R₅ die angegebene Bedeutung haben.Of these, preference is given to those compounds of the formula (1) in which
R₁
Phenyl or
Figure imgb0013
 wherein R₄₀, R₄₁ and R₄₂ independently of one another are hydrogen or C₁-C₈-alkyl,
R₃
Hydrogen, C₁-C₁₂-alkyl or -DE,
R₂
Hydrogen,
R₄
Hydrogen or C₁-C₄ alkyl, and
R₅
Is C₁-C₂₀ alkyl,
where D and E have the meanings given, and in particular those compounds in which
R₁
Phenyl or
Figure imgb0014
 wherein R₄₀, R₄₁ and R₄₂ independently of one another are hydrogen or C₁-C₄-alkyl,
R₃
C₁-C₄ alkyl or -DE,
R₂ and R₄
Hydrogen, and
R₅
C₁-C₄-alkyl or cyclopentyl or cyclohexyl, where D is -C (R₁₁) ₂- and E is a radical of the formula
Figure imgb0015
is, where the substituents R₁₁ are the same or different and are each C₁-C₄-alkyl, and R₁, R₂, R₄ and R₅ have the meaning given.

Besonders bevorzugt sind Verbindungen der Formel (1), worin

R₁
Phenyl oder
Figure imgb0016
 worin R₄₀,R₄₁ und R₄₂ unabhängig voneinander C₁-C₄-Alkyl,
R₄ und R₂
Wasserstoff,
R₃ und R₅
unabhängig voneinander C₁-C₁₈-Alkyl, Cyclopentyl oder Cyclohexyl ist, wobei als Beispiele die Verbindungen (2) und (3) genannt seien.
Figure imgb0017
Figure imgb0018
Compounds of the formula (1) in which
R₁
Phenyl or
Figure imgb0016
 wherein R₄₀, R₄₁ and R₄₂ are independently C₁-C₄ alkyl,
R₄ and R₂
Hydrogen,
R₃ and R₅
is independently C₁-C₁₈ alkyl, cyclopentyl or cyclohexyl, examples of which are compounds (2) and (3).
Figure imgb0017
Figure imgb0018

Die Verbindungen der Formel (1) werden üblicherweise aus wässrigem Bad appliziert. Die Applikation kann vor, während oder nach dem optischen Aufhellen der Fasern, nach einem Auszieh- oder Kontinueverfahren erfolgen. Die Applikation gemeinsam mit dem optischen Aufheller ist bevorzugt.The compounds of formula (1) are usually applied from an aqueous bath. The application can take place before, during or after the optical brightening of the fibers, using a pull-out or continuous process. Application together with the optical brightener is preferred.

Beim Ausziehverfahren kann man 0,01 bis 1%, vorzugsweise 0,05 bis 0,5%, optischen Aufheller und 0,01 bis 3%, vorzugsweise 0,03 bis 0,3% der Verbindungen der Formel (1) einsetzen.In the exhaust process, 0.01 to 1%, preferably 0.05 to 0.5%, optical brightener and 0.01 to 3%, preferably 0.03 to 0.3%, of the compounds of the formula (1) can be used.

Beim Kontinueverfahren kann man 0,1 bis 10 g/l, vorzugsweise 0,2 bis 2 g/l, optischen Aufheller und 0,1 bis 30 g/l, vorzugsweise 0,2 bis 2 g/l der Verbindungen der Formel (1) einsetzen.In the continuous process, 0.1 to 10 g / l, preferably 0.2 to 2 g / l, optical brightener and 0.1 to 30 g / l, preferably 0.2 to 2 g / l, of the compounds of the formula (1 ) deploy.

Unter Polyamidfasermaterial wird synthetisches Polyamidfasermaterial, wie z.B. solches aus Polyamid-6, Polyamid-6,6 oder Polyamid-12, sowie aus modifiziertem Polyamid, z.B. basisch anfärbbaren Polyamid verstanden. Neben den reinen Polyamidfasern kommen vor allem auch Fasermischungen aus Polyamid und Polyurethan in Betracht, so z.B. Trikotmaterial aus Polyamid/Polyurethanfasern im Mischungsverhältnis 70:30. Grundsätzlich kann das reine oder gemischte Polyamidfasermaterial in den verschiedensten Verarbeitungsformen vorliegen, wie z.B. als Faser, Garn, Gewebe, Gewirke, Vlies oder Flormaterial.Polyamide fiber material is understood to mean synthetic polyamide fiber material, such as, for example, that of polyamide-6, polyamide-6,6 or polyamide-12, and of modified polyamide, for example polyamide which can be dyed in the base. In addition to the pure polyamide fibers occur especially fiber mixtures made of polyamide and polyurethane, such as tricot material made of polyamide / polyurethane fibers in a mixing ratio of 70:30. In principle, the pure or mixed polyamide fiber material can be in a wide variety of processing forms, such as fiber, yarn, woven, knitted, nonwoven or pile material.

Für polyamidhaltige Fasermaterialien geeignete optische Aufheller sind z.B. solche der allgemeinen Formeln (5) bis (11).Optical brighteners suitable for polyamide-containing fiber materials are e.g. those of the general formulas (5) to (11).

Bis-triazolyl-stilbene der allgemeinen Formel (5)

Figure imgb0019
sowie deren z.B. Alkalimetall-Salze, worin die Reste R₁₂, R₁₃, R₁₄ und R₁₅ unabhängig voneinander z.B. H, C₁-C₆-Alkyl, Phenyl oder mit beispielsweise Sulfonsäuregruppen substituiertes Phenyl bedeuten können.Bis-triazolyl-stilbenes of the general formula (5)
Figure imgb0019
 and, for example, their alkali metal salts, in which the radicals R₁₂, R₁₃, R₁₄ and R₁₅ independently of one another can mean, for example, H, C₁-C₆-alkyl, phenyl or phenyl substituted with, for example, sulfonic acid groups.

Bis-triazinylamino-stilbene der allgemeinen Formel (6)

Figure imgb0020
sowie deren z.B. Alkalimetall-Salze,
worin die Reste R₁₆, R₁₇, R₁₈ und R₁₉ unabhängig voneinander z.B.
Figure imgb0021
Figure imgb0022
 -N(C₁-C₆-hydroxyalkyl)₂, -N(C₁-C₆-Alkyl)(C₁-C₆-hydroxyalkyl),
-NH₂, -N(C₁-C₆-Alkyl)₂, C₁-C₆-Alkoxy, Cl, -NH-(C₁-C₆-sulfoalkyl) oder
-NH-(C₁-C₆-hydroxyalkyl)
bedeuten können.Bis-triazinylamino-stilbenes of the general formula (6)
Figure imgb0020
 as well as their, for example, alkali metal salts,
wherein the radicals R₁₆, R₁₇, R₁₈ and R₁₉ independently, for example
Figure imgb0021
Figure imgb0022
 -N (C₁-C₆-hydroxyalkyl) ₂, -N (C₁-C₆-alkyl) (C₁-C₆-hydroxyalkyl),
-NH₂, -N (C₁-C₆-alkyl) ₂, C₁-C₆-alkoxy, Cl, -NH- (C₁-C₆-sulfoalkyl) or
-NH- (C₁-C₆-hydroxyalkyl)
can mean.

Distyryl-biphenyle der allgemeinen Formel (7)

Figure imgb0023
sowie deren z.B. Alkalimetall-Salze,
worin die Reste R₂₀, R₂₁, R₂₂ und R₂₃ unabhängig voneinander z.B.
H, Sulfo bzw. Sulfino, -SO₂N(C₁-C₆-Alkyl)₂, -SO₂-(C₁-C₆-Alkyl), -OCH₃, -CN, -Cl, -COOCH₃ oder -CON(C₁-C₆-Alkyl)₂ bedeuten können.Distyryl biphenyls of the general formula (7)
Figure imgb0023
 as well as their, for example, alkali metal salts,
wherein the radicals R₂₀, R₂₁, R₂₂ and R₂₃ independently, for example
H, sulfo or sulfino, -SO₂N (C₁-C₆-alkyl) ₂, -SO₂- (C₁-C₆-alkyl), -OCH₃, -CN, -Cl, -COOCH₃ or -CON (C₁-C₆-alkyl) ₂ can mean.

Bis-benzoxazolyl-derivate der allgemeinen Formel (8)

Figure imgb0024
worin die Reste R₂₄, R₂₅, R₂₆ und R₂₇ unabhängig voneinander z.B.
H, verzweigtes oder unverzweigtes C₁-C₆-Alkyl, insbesondere tert.-Butyl, tert.-Butyl-Phenyl oder -COOC₁-C₆-Alkyl und
Figure imgb0025
Figure imgb0026
 bedeuten können.Bis-benzoxazolyl derivatives of the general formula (8)
Figure imgb0024
 wherein the radicals R₂₄, R₂₅, R₂₆ and R₂₇ independently, for example
H, branched or unbranched C₁-C₆-alkyl, especially tert-butyl, tert-butyl-phenyl or -COOC₁-C₆-alkyl and
Figure imgb0025
Figure imgb0026
 can mean.

Coumarine der allgemeinen Formel (9)

Figure imgb0027
sowie deren z.B. Alkalimetall-Salze,
worin die Reste
R₂₈ H, C₁-C₆-Alkyl oder C₁-C₆-Carboxy,
R₂₉ H, Phenyl, Carboxy-C₁-C₆-Alkyl oder
Figure imgb0028
 und
R₃₀
Figure imgb0029
Figure imgb0030
 -O-(C₁-C₆-Alkyl), -N(C₁-C₆-Alkyl)₂ oder -NH-CO-(C₁-C₆-Alkyl) bedeuten können.Coumarins of the general formula (9)
Figure imgb0027
 as well as their, for example, alkali metal salts,
where the residues
R₂₈ H, C₁-C₆-alkyl or C₁-C₆-carboxy,
R₂₉ H, phenyl, carboxy-C₁-C₆ alkyl or
Figure imgb0028
 and
R₃₀
Figure imgb0029
Figure imgb0030
 -O- (C₁-C₆-alkyl), -N (C₁-C₆-alkyl) ₂ or -NH-CO- (C₁-C₆-alkyl) can mean.

Pyrazoline der allgemeinen Formel (10)

Figure imgb0031
sowie deren z.B. Alkalimetall-Salze,
worin die Reste

R₃₁
H, Cl oder Amino (einschliesslich substituierte Amine, wie z.B. Methylamine, Dimethylamin, Diethylamin, Diethanolamin, Anilin),
R₃₂ und R₃₃
unabhängig voneinander H oder C₁-C₆-Alkyl, Phenyl,
R₃₄
H oder Cl und
R₃₅
H, Cl, Sulfo bzw. Sulfino, -SO₂N(C₁-C₆-Alkyl)₂, -SO₂-(C₁-C₆-Alkyl), -OCH₃, -CN, -Cl, -COO(C₁-C₆-Alkyl) oder -CON(C₁-C₆-Alkyl)₂ bedeuten.
Pyrazolines of the general formula (10)
Figure imgb0031
 as well as their, for example, alkali metal salts,
where the residues
R₃₁
H, Cl or amino (including substituted amines, such as, for example, methylamine, dimethylamine, diethylamine, diethanolamine, aniline),
R₃₂ and R₃₃
independently of one another H or C₁-C₆-alkyl, phenyl,
R₃₄
H or Cl and
R₃₅
H, Cl, sulfo or sulfino, -SO₂N (C₁-C₆-alkyl) ₂, -SO₂- (C₁-C₆-alkyl), -OCH₃, -CN, -Cl, -COO (C₁-C₆-alkyl) or -CON (C₁-C₆-alkyl) ₂ mean.

Dibenzofuranyl-biphenyle der allgemeinen Formel (11)

Figure imgb0032
sowie deren z.B. Alkalimetall-Salze,
worin die Reste R₃₇, R₃₈ und R₃₉ unabhängig voneinander
H, Halogen, CN, Phenoxy, Benzyloxy, C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder einen Sulfonsäurerest bedeuten können.Dibenzofuranyl biphenyls of the general formula (11)
Figure imgb0032
 as well as their, for example, alkali metal salts,
wherein the radicals R₃₇, R₃₈ and R₃₉ independently
H, halogen, CN, phenoxy, benzyloxy, C₁-C₄-alkyl, C₁-C₄-alkoxy or a sulfonic acid residue.

Die vorgenannten Aufheller sind bekannt und ihre Herstellung z.B. in US-A-4 093 645, Angewandte Chemie, 87, S. 693 und Ullmann's Encyclopedie of Indust. Chem. (5. Ausgabe, 1991) Vol. A 18, S. 156-167 beschrieben.The aforementioned brighteners are known and their preparation is described, for example, in US Pat. No. 4,093,645, Angewandte Chemie, 87 , p. 693 and Ullmann's Encyclopedie of Indust. Chem. (5th edition, 1991) Vol. A 18, pp. 156-167.

Als für das Verfahren geeignete Farbstoffe kommen alle die zum Färben der oben genannten Textilien geeigneten Farbstoffe wie Azo-, Anthrachinon-, Nitro,- Acridon-, oder Naphthochinonfarbstoffe in Frage.Suitable dyes for the process are all dyes suitable for dyeing the above-mentioned textiles, such as azo, anthraquinone, nitro, acridone or naphthoquinone dyes.

Die Herstellung des Mittels zum optischen Aufhellen von polyamidfaserhaltigen Artikeln mit verbesserten Mouldingechtheiten erfolgt durch Mischen der Komponenten, wobei dann auch allfällige Hilfsstoffe eingearbeitet werden können.The agent for the optical brightening of articles containing polyamide fibers with improved molding fastness properties is produced by mixing the components, in which case any auxiliaries can also be incorporated.

Übliche Hilfsstoffe sind z.B. Dispergier-, Egalisier- und Waschmittel, wie Fettalkoholpolyglykolether, Alkylethoxylate oder Alkylphenolethoxylate, anionische Alkylbenzolsulfonate oder lineare Alkylsulfonate, allein oder kombiniert mit Benzimidazol-derivaten oder ethoxylierten Fettaminen, sowie Sequestriermittel, wie Na-Salz der Ethylendiamintetraessigsäure, oder Bleichmittel, wie Na-dithionit, sowie Kombinationen von zwei oder mehreren Hilfsmitteln.Common auxiliaries are e.g. Dispersing, leveling and washing agents, such as fatty alcohol polyglycol ethers, alkyl ethoxylates or alkylphenol ethoxylates, anionic alkylbenzenesulfonates or linear alkylsulfonates, alone or in combination with benzimidazole derivatives or ethoxylated fatty amines, and sequestering agents, such as Na salt of ethylenediaminetetraionic acid, such as Na or bidentate acetic acid, or Na and combinations of two or more aids.

Die abschliessende Formgebung (Moulding) der Textilien erfolgt nach den üblichen Verfahrensweisen.The final shaping (molding) of the textiles is carried out according to the usual procedures.

Die folgenden Beispiele veranschaulichen die Erfindung ohne sie jedoch hierauf beschränken zu wollen. Teile bedeuten Gewichtsteile und Prozente Gewichtsprozente, welche auf das Textilgewicht bezogen sind.The following examples illustrate the invention without, however, wishing to restrict it thereto. Parts mean parts by weight and percentages by weight, which are based on the textile weight.

In den folgenden Beispielen wird als Textil ein PA-6 Texturtrikot verwendet. Der Aufheller und die Benzofuran-2-on-Verbindung werden im Ausziehverfahren appliziert, wobei dem Behandlungsbad noch 3 g/l stabilisiertes Hydrosulfit (Clarit PS®) zugegeben werden. Die Behandlungsdauer beträgt 30 min. bei einer Temperatur von 120°C.In the following examples, a PA-6 texture jersey is used as the textile. The brightener and the benzofuran-2-one compound are applied in the exhaust process, with 3 g / l of stabilized hydrosulfite (Clarit PS®) being added to the treatment bath. The treatment lasts 30 minutes. at a temperature of 120 ° C.

Die Bestimmung des Weissgrades erfolgt nach der Methode nach Ganz (Ganz, Appl. Optics 18, 1073-1078 (1979)) mit Hilfe eines Zeiss RFC 3 Spektrometers.The degree of whiteness is determined according to the Ganz method (Ganz, Appl. Optics 18 , 1073-1078 (1979)) using a Zeiss RFC 3 spectrometer.

Beispiel 1 (Vergleichsbeispiel):Example 1 (comparative example):

Es wird der Aufheller der Formel (12)

Figure imgb0033
bei einer Konzentration von 0,2% aus einem wässrigen Bad appliziert. Der Weissgrad beträgt 270 Einheiten.
Eine Hälfte des Textilstückes wird dann dem Mouldingtest unterzogen:
Bei einem "Rhodiaceta Thermotester' (Firma Setaran, Lyon/F) mit 13 heizbaren Metallplättchen à 15x35 mm wird die Temperatur eines der mittleren Plättchen auf 199°C eingestellt. Der untere Sockel wird mit einer ca. 3 mm dicken Wollfilzunterlage überzogen. Das Textilstück wird während einer Minute gepresst (Pressdruck ca. 70 g/cm) und dann wieder auf seinen Weissgrad untersucht.The brightener of formula (12)
Figure imgb0033
 applied at a concentration of 0.2% from an aqueous bath. The degree of whiteness is 270 units.
Half of the textile piece is then subjected to the molding test:
In a "Rhodiaceta Thermotester '(Setaran, Lyon / F) with 13 heatable metal plates of 15x35 mm, the temperature of one of the middle plates is set to 199 ° C. The lower base is covered with an approximately 3 mm thick wool felt pad. The textile piece is pressed for one minute (pressing pressure approx. 70 g / cm) and then examined again for its whiteness.

Nach dem Mouldingtest beträgt der Weissgradverlust etwa 50 Einheiten.After the molding test, the loss of whiteness is about 50 units.

Beispiel 2:Example 2:

Es wird wie in Beispiel 1 verfahren, mit dem einzigen Unterschied, dass zu dem dort verwendeten optischen Aufheller im Applikationsbad ein Benzofuran-2-on der Formel (2)

Figure imgb0034
in Form einer wässrigen Dispersion, in einer Konzentration von 0,1 % zugesetzt wird. Nach dem Mouldingtest gemäss Beispiel 1 beträgt der Weissgradverlust etwa 20 Einheiten, bei gleicher Formstabilität wie in Beispiel 1.The procedure is as in Example 1, with the only difference that, in addition to the optical brightener used there, a benzofuran-2-one of the formula (2)
Figure imgb0034
 in the form of an aqueous dispersion, in a concentration of 0.1%. After the molding test according to Example 1, the loss of whiteness is about 20 units, with the same dimensional stability as in Example 1.

Beispiel 3 (Vergleichsbeispiel):Example 3 (comparative example):

Es wird wie in Beispiel 1 verfahren, mit dem einzigen Unterschied, dass ein Aufheller der Formel (13) verwendet wird

Figure imgb0035
Nach dem Mouldingtest beträgt der Weissgradverlust etwa 25 EinheitenThe procedure is as in Example 1, with the only difference that a brightener of the formula (13) is used
Figure imgb0035
 After the molding test, the loss of whiteness is about 25 units

Beispiel 4:Example 4:

Es wird wie in Beispiel 3 verfahren, mit dem einzigen Unterschied, dass zu dem dort verwendeten optischen Aufheller im Applikationsbad ein Benzofuran-2-on der Formel (3)

Figure imgb0036
in Form einer wässrigen Dispersion, in einer Konzentration von 0,1 % zugesetzt wird. Nach dem Mouldingtest gemäss Beispiel 1 beträgt der Weissgradverlust etwa 10 Einheiten, bei gleicher Formstabilität wie in Beispiel 3.The procedure is as in Example 3, with the only difference that, in addition to the optical brightener used there, a benzofuran-2-one of the formula (3)
Figure imgb0036
 in the form of an aqueous dispersion, in a concentration of 0.1%. After the molding test according to Example 1, the loss of whiteness is about 10 units, with the same dimensional stability as in Example 3.

Beispiel 5 (Vergleichsbeispiel):Example 5 (comparative example):

Es wird wie in Beispiel 1 verfahren, mit dem einzigen Unterschied, dass ein Aufheller der Formel (14) verwendet wird

Figure imgb0037
Nach dem Mouldingtest beträgt der Weissgradverlust etwa 38 EinheitenThe procedure is as in Example 1, with the only difference that a brightener of the formula (14) is used
Figure imgb0037
 After the molding test, the loss of whiteness is about 38 units

Beispiel 6:Example 6:

Es wird wie in Beispiel 5 verfahren, mit dem einzigen Unterschied, dass zu dem dort verwendeten optischen Aufheller im Applikationsbad ein Benzofuran-2-on der Formel (3)

Figure imgb0038
in Form einer wässrigen Dispersion, in einer Konzentration von 0,1 % zugesetzt wird. Nach dem Mouldingtest gemäss Beispiel 1 beträgt der Weissgradverlust etwa 16 Einheiten, bei gleicher Formstabilität wie in Beispiel 5.The procedure is as in Example 5, with the only difference that, in addition to the optical brightener used there, a benzofuran-2-one of the formula (3)
Figure imgb0038
 in the form of an aqueous dispersion, in a concentration of 0.1%. After the molding test according to Example 1, the loss of whiteness is about 16 units, with the same dimensional stability as in Example 5.

Claims (14)

  1. A process for the preparation of shaped, polyamide fibre-containing articles having enhanced moulding properties, which comprises applying to the fibres, before, during or after whitening and optionally dyeing the fibres, a compound of formula (1)
    Figure imgb0057
     wherein
    R₁   is unsubstituted or substituted phenyl, wherein the substituents are 1 to 3 alkyl radicals together containing not more than 18 carbon atoms, C₁-C₁₂alkoxy, C₁-C₁₈acyloxy, C₁-C₁₈alkoxycarbonyl, chloro or a mixture of these substituents,
    R₂   is hydrogen or C₁-C₄alkyl,
    R₄   is hydrogen, C₁-C₁₂alkyl, unsubstituted or C₁-C₄alkyl-substituted C₅-C₇cycloalkyl, phenyl, C₇-C₁₂phenylalkyl or chloro,
    R₃   has the meaning of R₂ or R₄ or is a radical of formula
    Figure imgb0058
    Figure imgb0059
    Figure imgb0060
    Figure imgb0061
     -D-E, wherein
    n   is 0, 1 or 2,
    R₆   is hydrogen, C₁-C₁₈alkyl, C₂-C₁₈alkyl which is interrupted by oxygen or sulfur, dialkylaminoalkyl containing a total of 3 to 16 carbon atoms, cyclopentyl, cyclohexyl, phenyl or phenyl which is substituted by 1 to 3 alkyl radicals together containing not more than 18 carbon atoms,
    the substituents R₇   are each independently of the other hydrogen, C₁-C₁₈alkyl, cyclopentyl, cyclohexyl, phenyl, phenyl which is substituted by 1 or 2 alkyl radicals together containing not more than 16 carbon atoms, a radical of formula -C₂H₄OH, -C₂H₄-O-CmH2m+1 or
    Figure imgb0062
     or, together with the nitrogen atom to which they are attached, form a piperidine or morpholine radical,
    m   is 1 to 18,
    R₁₀   is hydrogen, C₁-C₂₂alkyl or C₅-C₁₂cycloalkyl,
    A   is alkylene of 2 to 22 carbon atoms which may be interrupted by nitrogen, oxygen or sulfur,
    R₈   is hydrogen, C₁-C₁₈alkyl, cyclopentyl, cyclohexyl, phenyl, phenyl which is substituted by 1 or 2 alkyl radicals together containing not more than 16 carbon atoms, or benzyl,
    R₉   is C₁-C₁₈alkyl,
    D   is -O-, -S-, -SO-, -SO₂- or -C(R₁₁)₂-,
    the substituents R₁₁   are each independently of the other hydrogen, alkyl together containing not more than 16 carbon atoms, phenyl or a radical of formula
    Figure imgb0063
     wherein n, R₆ and R₇ have the given meanings,
    E   is a radical of formula
    Figure imgb0064
     wherein R₁, R₂ and R₄ have the given meanings, and
    R₅   is hydrogen, C₁-C₃₀alkyl, cyclopentyl, cyclohexyl, chloro or a radical of formula
    Figure imgb0065
     wherein R₆ and R₇ have the given meanings, or
    R₅   together with R₄ forms a tetramethylene radical,
    and then thermally shaping the articles thus treated.
  2. A process according to claim 1 which comprises the use of a compound of formula (1) wherein R₂ is hydrogen.
  3. A process according to claim 1 which comprises the use of a compound of formula (1) wherein R₃ is hydrogen, C₁-C₁₂alkyl, cyclopentyl, cyclohexyl, chloro or a radical of formula
    Figure imgb0066
     or -D-E, wherein n, R₆, R₇, D and E are as defined in claim 1.
  4. A process according to claim 3 which comprises the use of a compound of formula (1) wherein R₆ is hydrogen, C₁-C₁₈alkyl, cyclopentyl or cyclohexyl.
  5. A process according to claim 1 which comprises the use of a compound of formula (1) wherein
    R₁   is unsubstituted or substituted phenyl, wherein the substituents are 1 or 2 alkyl radicals together containing not more than 12 carbon atoms, C₁-C₁₂acyloxy or a mixture of these substituents:
    R₂   is hydrogen,
    R₄   is hydrogen or C₁-C₁₂alkyl,
    R₃   is hydrogen, C₁-C₁₂alkyl,
    Figure imgb0067
     or -D-E,
    R₅   is hydrogen, C₁-C₂₀alkyl,
    Figure imgb0068
     or
    R₅   together with R₄ forms a tetramethylene radical, and n, R₆, R₇, D and
    E are as defined in claim 1.
  6. A process according to claim 5 which comprises the use of a compound of formula (1) wherein
    R₁   is phenyl or
    Figure imgb0069
     wherein R₄₀, R₄₁ and R₄₂ are each independently of one another hydrogen or C₁-C₈alkyl,
    R₃   is hydrogen, C₁-C₁₂alkyl or -D-E,
    R₂ and R₄   are each independently of the other hydrogen or C₁-C₄alkyl, and
    R₅   is C₁-C₂₀alkyl,
    and D and E are as defined in claim 5.
  7. A process according to claim 6 which comprises the use of a compound of formula (1) wherein
    R₁   is phenyl or
    Figure imgb0070
     wherein R₄₀, R₄₁ and R₄₂ are each independently of one another hydrogen or C₁-C₄alkyl,
    R₃   is C₁-C₄alkyl or -D-E,
    R₂ and R₄   are hydrogen, and
    R₅   is C₁-C₄alkyl or cyclopentyl or cyclohexyl,
    and D is -C(R₁₁)₂- and E is a radical of formula
    Figure imgb0071
     and the substituents R₁₁ are identical or different and are each C₁-C₄alkyl, and R₁, R₂, R₄ and R₅ are as defined.
  8. A process according to claim 1 which comprises the use of a compound of formula (1) wherein
    R₁   is phenyl or
    Figure imgb0072
     wherein R₄₀, R₄₁ and R₄₂ are each independently of one another C₁-C₄alkyl,
    R₄ and R₂   are hydrogen, and
    R₃ and R₅   are each independently of the other C₁-C₁₈alkyl, cyclopentyl or cyclohexyl.
  9. A process according to claim 1 which comprises the use of a compound of formula (2) or (3)
    Figure imgb0073
    Figure imgb0074
  10. A process according to any one of claims 1-9 which comprises the use of a fluorescent whitening agent having the basic structure of a bis-triazinylamino-stilbene, his-triazolyl-stilbene, distyrylbiphenyl, bis-benzoxazolyl derivative, coumarin, pyrazoline or dibenzofuranylbiphenyl.
  11. A process according to claim 10 which comprises the use of a mixture of a fluorescent whitening agent and one or more dyes such as azo, anthraquinone, nitro, acridone or naphthoquinone dyes.
  12. A process according to claim 1 which comprises the use of a compound of formula (1) in a concentration of 0.01 to 3 % in the exhaust process or in an amount of 0.1 to 30 g/l in the continuous process.
  13. A process according to claim 12 which comprises the use of a compound of formula (1) in a concentration of 0.03 to 0.3 % in the exhaust process or in an amount of 0.2 to 2 g/l in the continuous process.
  14. A polyamide fibre-containing article having enhanced moulding properties which has been treated by the process according to claim 1.
EP92810821A 1991-11-01 1992-10-23 Compound and process for the production of good quality moulded articles Expired - Lifetime EP0540471B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3194/91 1991-11-01
CH319491 1991-11-01

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EP0540471A1 EP0540471A1 (en) 1993-05-05
EP0540471B1 true EP0540471B1 (en) 1996-05-01

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EP (1) EP0540471B1 (en)
JP (1) JPH05230774A (en)
CA (1) CA2081812C (en)
DE (1) DE59206173D1 (en)
ES (1) ES2086715T3 (en)
MX (1) MX9205504A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH686306A5 (en) 1993-09-17 1996-02-29 Ciba Geigy Ag 3-aryl-benzofuranones as stabilizers.
TW593303B (en) * 2001-09-11 2004-06-21 Ciba Sc Holding Ag Stabilization of synthetic polymers
US20090165215A1 (en) * 2006-04-24 2009-07-02 Huntsman International Llc Process for the enhancement of thermostability
KR100862645B1 (en) * 2007-05-18 2008-10-09 한국생명공학연구원 New fumimycin compound with peptide deformylase-inhibitory activity and antimicrobial activity

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2535098A (en) * 1947-06-13 1950-12-26 Monsanto Chemicals Gamma-valerolactone and gammabutyrolactone as dyeing assistants for cellulose ester and ether yarns and fabrics
US4002423A (en) * 1971-08-13 1977-01-11 Hoechst Aktiengesellschaft Benzofuran derivatives process for their preparation and their use as optical brighteners
US4093645A (en) * 1972-07-26 1978-06-06 Hickson & Welch Limited Styryl-tetrahydronaphthyl derivatives
GB2042562B (en) * 1979-02-05 1983-05-11 Sandoz Ltd Stabilising polymers
US4581035A (en) * 1984-11-08 1986-04-08 Crucible Chemical Company Waterless dye composition and method of use thereof for coloring thermoplastic articles
US5175312A (en) * 1989-08-31 1992-12-29 Ciba-Geigy Corporation 3-phenylbenzofuran-2-ones
EP0415887B1 (en) * 1989-08-31 1994-10-05 Ciba-Geigy Ag 3-Phenyl-benzofuran-3-ones

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JPH05230774A (en) 1993-09-07
ES2086715T3 (en) 1996-07-01
CA2081812A1 (en) 1993-05-02
EP0540471A1 (en) 1993-05-05
MX9205504A (en) 1993-06-01
US5322525A (en) 1994-06-21
DE59206173D1 (en) 1996-06-05
CA2081812C (en) 2002-07-02
US5437689A (en) 1995-08-01

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