ES2576504T3 - Catalizadores de blanqueo - Google Patents

Catalizadores de blanqueo Download PDF

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Publication number
ES2576504T3
ES2576504T3 ES14173100.0T ES14173100T ES2576504T3 ES 2576504 T3 ES2576504 T3 ES 2576504T3 ES 14173100 T ES14173100 T ES 14173100T ES 2576504 T3 ES2576504 T3 ES 2576504T3
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Spain
Prior art keywords
alkyl
substituted
unsubstituted
hydroxy
phenyl
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ES14173100.0T
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English (en)
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Hauke Rohwer
Barbara WINKLER
Frédérique Wendeborn
Katharina Misteli
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BASF SE
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BASF SE
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0215—Sulfur-containing compounds
    • B01J31/0218—Sulfides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms 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 the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms 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 the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/02—Preparation in the form of powder by spray drying
    • C—CHEMISTRY; METALLURGY
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    • C11D3/16—Organic compounds
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    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames
    • C—CHEMISTRY; METALLURGY
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    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
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    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/3927—Quarternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
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    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
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    • C11D3/3942—Inorganic per-compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D3/3947—Liquid compositions
    • C—CHEMISTRY; METALLURGY
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    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3281—Heterocyclic compounds
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    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/34—Organic compounds containing sulfur
    • 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
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B08—CLEANING
    • B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
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    • B08B3/04—Cleaning involving contact with liquid
    • B08B3/08—Cleaning involving contact with liquid the liquid having chemical or dissolving effect
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    • C11D3/34—Organic compounds containing sulfur
    • C11D3/3481—Organic compounds containing sulfur containing sulfur in a heterocyclic ring, e.g. sultones or sulfolanes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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    • C11D3/34—Organic compounds containing sulfur
    • C11D3/349—Organic compounds containing sulfur additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea
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    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Detergent Compositions (AREA)

Abstract

Un compuesto de fórmula (1)**Fórmula** en donde R1, R2, R3, R4 independientemente uno de otro son hidrógeno, alquilo C1 - C28 alcoxi C1-C28, alquenilo C2 - C28, alquinilo C2 - C22, cicloalquilo C3 - C12, cicloalquenilo C3 - C12, aralquilo C7 - C9, heteroalquilo C3 - C20, cicloheteroalquilo C3 - C12, heteroaralquilo C5 - C16 no sustituido o sustituido, fenilo o naftilo no sustituido o sustituido, en el que los sustituyentes para los radicales se seleccionan del grupo que consiste en alquilo C1 - C4; hidroxi; sulfo; sulfato; halógeno; ciano; nitro; carboxi; aminado; N-mono- o N, N-di- alquilamino C1 - C4 o sustituido con hidroxi en el fragmento alquilo; N-fenilamino; N naftilamino, en el que los grupos amino pueden ser cuaternarios; fenilo; fenoxi o naftiloxi; o R1, R2, R3, R4, independientemente uno de otro son OR11, NR11R12, NO2 o halógeno; o R1 y R2, R2 y R3 o R3 y R4 están unidos entre sí para formar 1, 2 o 3 carbocíclicos o heterocíclicos anillos, que pueden estar interrumpidos por uno o más -O-, -S-o -NR13- y que pueden estar condensados adicionalmente con otros anillos aromáticos y/o que pueden estar sustituidos con uno o más grupos alquilo C1 - C6. R5 denota hidrógeno, alquilo C1 - C28 alcoxi C1-C28, alquenilo C2 - C28, alquinilo C2 - C22, cicloalquilo C3 - C12, cicloalquenilo C3 - C12, aralquilo C7 - C9, heteroalquilo C3 - C20, cicloheteroalquilo C3 - C12, heteroaralquilo C5 - C16 no sustituido o sustituido, fenilo no sustituido o sustituido, o heteroarilo no sustituido o sustituido; en donde los sustituyentes para los radicales se seleccionan del grupo que consiste de alquilo C1-C4; C1-C4; hidroxi; sulfo; sulfato; halógeno; ciano; nitro; carboxi; aminado; N-mono- o N, N-di-C1-C4 alquilamino no sustituido o sustituido con hidroxi en el fragmento alquilo; N-fenilamino; naftilamino N- en el que los grupos amino pueden ser cuaternarios; fenilo; fenoxi o naftiloxi; R6 denota hidrógeno, alquilo C1 - C28 alcoxi C1-C28, alquenilo C2 - C28, alquinilo C2 - C22, cicloalquilo C3 - C12, cicloalquenilo C3 - C12, aralquilo C7 - C9, heteroalquilo C3 - C20, cicloheteroalquilo C3 - C12, heteroaralquilo C5 - C16, fenilo no sustituido o sustituido o naftilo, o heteroarilo no sustituido o sustituido; en donde los sustituyentes para los radicales se seleccionan del grupo que consiste en alquilo C1 - C4; hidroxi; sulfo; sulfato; halógeno; ciano; nitro; carboxi; aminado; N-mono- o N, N-di-C1-C4 alquilamino no sustituido o sustituido con hidroxi en el fragmento alquilo; Nfenilamino; amino N-naftilo en el que los grupos amino pueden ser cuaternarios; fenilo; fenoxi o naftiloxi; R7 es un grupo**Fórmula** en donde cada grupo con un anión A- ; k es un número entero de 1 a 4; A- es el anión de un ácido orgánico o inorgánico; R10 denota hidrógeno, alquilo C1-C28 alquenilo C2 -C28, alquinilo C2 -C22, cicloalquilo C3 -C12, cicloalquenilo C3 -C12, aralquilo C7 - C9, heteroalquilo C3 - C20, cicloheteroalquilo C3 - C12, heteroaralquilo C5 - C16; R11, R12 son independientemente hidrógeno, alquilo C1-C18 o fenilo; o R10 y R11 junto con el átomo de nitrógeno al cual están unidos forman un anillo de 5 miembros-o 6 que puede contener un átomo adicional de N, O o S. R13 denota hidrógeno o alquilo C1-C18; con la condición de que se excluye (N-[(2-hidroxifenil) metilenamino] -2-(4- metilmorfolin-4-io-4-il) acetamida cloruro.

Description

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en peso a 50% en peso, con base en el peso total de la formulación detergente. Las formulaciones detergentes pueden también utilizarse en forma llamada "dosis unitaria líquida".
Otra formulación preferida para un detergente es un gránulo que comprende:
a) 1 a 99% en peso, con base en el peso total del gránulo, de al menos un compuesto de fórmula (1) como se describe anteriormente y de al menos un peróxido,
b) 1 a 99% en peso, con base en el peso total del gránulo, de al menos un aglutinante,
c) 0 a 20% en peso, con base en el peso total del gránulo, de al menos un material de encapsulación,
d) 0 a 20% en peso, con base en el peso total del gránulo, de al menos otro aditivo y
e) 0 a 20% en peso con base en el peso total del gránulo, de agua.
Los gránulos comprenden un polímero orgánico soluble en agua como aglutinante. Tales polímeros pueden ser utilizados solos o en forma de mezclas de dos o más polímeros.
Polímeros solubles en agua que entran en consideración son, por ejemplo, polietilenglicoles, copolímeros de óxido de etileno con óxido de propileno, gelatina, poliacrilatos, polimetacrilatos, polivinilpirrolidonas, vinilpirrolidonas, acetatos de vinilo, polivinilimidazoles, polivinilpiridina-N-óxidos, copolímeros de vinilpirrolidona de cadena larga α-olefinas, copolímeros de vinilpirrolidona con vinilimidazol, poli (vinilpirrolidona/dimetilaminoetilmetacrilatos), copolímeros de vinilpirrolidona/dimetilaminopropil metacrilamidas, copolímeros de vinilpirrolidona/dimetilaminopropilacrilamidas, copolímeros cuaternarios de vinilpirrolidona y dimetilaminoetil metacrilatos, terpolímeros de vinilcaprolactama/vinilpirrolidona/dimetilaminoetil metacrilatos, copolímeros de vinilpirrolidona y cloruro de metacrilamidopropil trimetil amonio. terpolímeros caprolactama/vinilpirrolidona/dimetilaminoetil metacrilatos, copolímeros de estireno y ácido acrílico, ácidos policarboxílicos, poliacrilamidas, carboximetilcelulosa, hidroximetilcelulosa, alcoholes de polivinilo, acetato de polivinilo, acetato de polivinilo hidrolizados, copolímeros de acrilato de etilo con metacrilate y ácido metacrílico, copolímeros de ácido maleico con hidrocarburos insaturados, y también la polimerización mixta de los productos de los polímeros mencionados.
De los polímeros orgánicos, se da preferencia especial a los polietilenglicoles, carboximetilcelulosa, poli acrilamidas, alcoholes de polivinilo, polivinilpirrolidonas, gelatina, acetatos de polivinilo hidrolizados, copolímeros de vinilpirrolidona y acetato de vinilo, y también poliacrilatos, copolímeros de etilacrilato con metacrilato y ácido metacrílico, y polymatacrilatos.
Los materiales encapsulantes incluyen especialmente polímeros y ceras solubles en agua y dispersables en agua De estos
materiales, se da preferencia a los polietilenglicoles, poliamidas, poliacrilamidas, alcoholes polivinílicos, polivinilpirrolidones, gelatina, acetatos de polivinilo hidrolizados, copolímeros de vinilpirrolidona y acetato de vinilo, y también poliacrilatos, parafinas, ácidos grasos, copolímeros de acrilato de etilo con metacrilato y ácido metacrílico, y polimetacrilatos.
Otros aditivos (d) que entran en consideración son, por ejemplo, agentes humectantes, eliminadores de polvo, al agua colorantes insolubles o solubles en agua o pigmentos, y también aceleradores de disolución, abrillantadores ópticos y agentes secuestrantes. Ejemplos que ya se han dado anteriormente.
Los compuestos de fórmula (1) son útiles en un proceso para el blanqueo de manchas o de suciedad en los materiales textiles en el contexto de un proceso de lavado o mediante la aplicación directa de un eliminador de manchas y para la limpieza de superficies duras que comprende poner en contacto un material textil o un material de superficie dura en un medio acuoso, un compuesto de fórmula (1) como se describe anteriormente y un peróxido o un precursor de peróxido o O2yo aire.
Los compuestos de fórmula (1) se pueden usar como un catalizador para reacciones de oxidación.
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Bromuro de N-[(2-hidroxifenil) metilenamino] -2-(4-metilmorfolin-4-io-4-il) acetamida:
17,8 g (0.07 mol) de compuesto 1C se agitó con 100 ml de etanol, se añadieron 8,7 g (0.07 moles) de salicilaldehído gota a gota a temperatura ambiente. Se obtiene una suspensión espesa de color blanco y se agita a temperatura 5 ambiente durante la noche. El sólido se filtró entonces y se secó para dar 23,4 g de un sólido blanco como una mezcla de dos isómeros del compuesto 101B.
1H-NMR (300 MHz, DMSO), δ [ppm]: 3,45 (s, 3H), 3,64-3,87 (m, 4H), 3,94-4,06 (m, 4H), 4,54 y 4,95 (2 s, 1 H), 6.85-6,95 (m, 2H), 7,25 -7,34 (m, 1 H), 7,62 y 7,80 (2 dd, J1 = 1.5 Hz, J2 = 7,8 Hz y J1 = 1,5 Hz, J2 = 7,8 Hz, 1 H), 8,39 y 8,56 (2s, 1 H), 10.08 y 10,75 (amplio 2S, 1 H), 11.95 y 12.51 (amplio 2S, 1 H).
10 Compuesto 102
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Lit. previamente preparado Compuesto 102
Cloruro de N-(2-hidroxi-1-naftil) metilenamino] -2-(4-metilmorfolin-4-io-4-il) acetamida: 2-hidroxi naftaldehído (98%; 5,08 g, 0.0289mol) se añade a 25 ° C a una suspensión agitada de cloruro de 2-(4-metilmorfolin-4-io-4-il)acetohidrazida (5,77
15 g, 0.0275mol; preparado de acuerdo con US3398147) en etanol (50 ml) y la suspensión resultante se agitó a continuación a 25 ° C (durante la noche) y 50 ° C (una hora). La mezcla de reacción se filtra, la torta de filtro se resuspendió en etanol fresco (70 ml) y la suspensión resultante se calentó a reflujo (una hora). Se calentó (45°C) se filtró y secó de la torta de filtración para proporcionar el compuesto indicado (7,1 g). Un sólido Amarillo beige;
1H-NMR (400 MHz, DMSO-d6), δ [ppm]: 3,48 (s) y 3,50 (s; 3H), 3,65-3,88 (m, 4H), 3,97-4,08 (m, 4H), 4,62 (s) y 5,03 (s;
20 2H), 7.25 a 7.27 (m, d-like) y 7,31-7,33 (m, d-similares; 1 H), 7,37-7,43 (m, 1 H), 7,57-7,62 (m, 1 H ), 7,85-7,87 (M, parecido a d), 7,89-7,91 (m, parecido a d) y 7,94-7,96 (m, parecido a d; 2H), 8,41-8,43 (m, parecido a d) a 8,80-8,82 (m, d -como; 1H),8,96 (s) y 9,47 (s; 1H), 10,84 (s ancho), 12,07 (s ancho), 12,16 (s ancho) y 13,54 (s ancho; 2H); LC/MS (Pos. ESI), zona% (m/z): 98,6 (328,2); calc. para C18H22N3O3: 328;
El Análisis elemental (para Cl solamente) encontró un 9,4%; calc. para C18ClH22N3O3: 9,7%.
25 Compuesto 103
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Lit. previamente preparado Compuesto 103
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Claims (1)

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CN101485565B (zh) * 2009-02-13 2011-04-13 华中科技大学 一种激光散斑血流成像分析方法
KR101831472B1 (ko) 2010-06-28 2018-02-22 바스프 에스이 금속 비함유 표백 조성물

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JP2016166226A (ja) 2016-09-15
RU2578565C2 (ru) 2016-03-27
CN103328455A (zh) 2013-09-25
JP5923109B2 (ja) 2016-05-24
US20150225357A1 (en) 2015-08-13
BR112013014591A2 (pt) 2016-07-19
US9051285B2 (en) 2015-06-09
ES2524734T3 (es) 2014-12-11
RU2013132311A (ru) 2015-01-20
KR101912962B1 (ko) 2018-10-29
JP6081640B2 (ja) 2017-02-15
PL2805942T3 (pl) 2016-09-30
AU2011344415B2 (en) 2016-05-26
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CN103328455B (zh) 2016-02-24
US9296713B2 (en) 2016-03-29
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