ES2613880T3 - Composition for permanent hydrophilization of polyolefin fibers and their use - Google Patents
Composition for permanent hydrophilization of polyolefin fibers and their use Download PDFInfo
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- ES2613880T3 ES2613880T3 ES13786214.0T ES13786214T ES2613880T3 ES 2613880 T3 ES2613880 T3 ES 2613880T3 ES 13786214 T ES13786214 T ES 13786214T ES 2613880 T3 ES2613880 T3 ES 2613880T3
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/04—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyolefins
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
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- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H3/00—Non-woven fabrics formed wholly or mainly of yarns or like filamentary material of substantial length
- D04H3/005—Synthetic yarns or filaments
- D04H3/007—Addition polymers
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
- D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/18—Synthetic fibres consisting of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/20—Polyalkenes, polymers or copolymers of compounds with alkenyl groups bonded to aromatic groups
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/11—Oleophobic properties
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- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Absorbent Articles And Supports Therefor (AREA)
- Nonwoven Fabrics (AREA)
Abstract
Composición para la hidrofilización permanente de fibras de poliolefina y filamentos de poliolefina y productos textiles no tejidos (no tejidos) fabricados a partir de los mismos, que contiene (A) 15 al 50 % en peso de al menos un tensioactivo no iónico, donde el tensioactivo no iónico se selecciona del siguiente grupo de compuestos que presentan respectivamente una o varias cadenas de hidrocarburo C6-C18 ramificadas o de cadena lineal, saturadas o insaturadas en su molécula: alcoholes grasos C6-C18 alcoxilados, aminas C6-C18 alcoxiladas, amidas C6-C18 alcoxiladas, ácidos C6-C18 grasos alcoxilados, ésteres de ácidos grasos C6-C18 alcoxilados y alquilfenoles C8-C18 alcoxilados; (B) 15 al 50 % en peso de al menos un compuesto de amonio cuaternario de fórmula general (I): [R1-C(>=O)-X-(CH2)n-NR2R3-(CH2)m-X-C(>=O)-R1]+ Y- (I) donde R1 es un grupo alquilo con 1 a 22 átomos de C o un grupo alquenilo con 2 a 22 átomos de C, R2 y R3 son independientemente entre sí, un grupo alquilo con 1 a 22 átomos de C, hidroxietilo o un resto de poliglicol, X es un átomo de oxígeno, NH, N-CH3 o un grupo (OC2H4)z con z >= 1 a 10, Y- es uno de los aniones CH3OSO3-, C2H5OSO3-, CH3COO-, Cl-, fosfato, lactato, citrato, y m y n significan, independientemente entre sí, un número entero de 1 a 6; donde el compuesto de amonio cuaternario está presente como sólido a temperatura ambiente (20 ºC); (C) 15 al 50 % en peso de al menos un éster de ácido fosfórico neutralizado de fórmula general (II): P(>=O)(OR4)(OR5)(OR6) (II) donde R4, R5 y R6, independientemente entre sí, (i) significan un grupo alquilo alcoxilado con 3 a 22 átomos de C en la cadena de hidrocarburo o un grupo alquenilo alcoxilado con 3 a 22 átomos de C en la cadena de hidrocarburo, en los que el número de grupos alcoxi por grupo alquilo o alquileno asciende a de 1 a 10, y en los que los grupos alquilo o grupos alquenilo pueden ser respectivamente ramificados o lineales, saturados o insaturados; (ii) significan un grupo alquilo con 3 a 22 átomos de C o un grupo alquenilo con 3 a 22 átomos de C, que pueden ser respectivamente ramificados o lineales, saturados o insaturados, y/o (iii) significan hidrógeno, donde por lo menos uno de los restos R4, R5 y R6 no es hidrógeno.Composition for permanent hydrophilicization of polyolefin fibers and polyolefin filaments and nonwoven (nonwoven) textile products manufactured therefrom, containing (A) 15 to 50% by weight of at least one nonionic surfactant, where the Nonionic surfactant is selected from the following group of compounds which respectively have one or more branched or straight-chain C6-C18 hydrocarbon chains, saturated or unsaturated in their molecule: alkoxylated C6-C18 fatty alcohols, alkoxylated C6-C18 amines, C6 amides -C18 alkoxylated, alkoxylated C6-C18 fatty acids, alkoxylated C6-C18 fatty acid esters and C8-C18 alkoxylated alkylphenols; (B) 15 to 50% by weight of at least one quaternary ammonium compound of general formula (I): [R1-C (> = O) -X- (CH2) n-NR2R3- (CH2) mXC (> = O) -R1] + Y- (I) where R1 is an alkyl group with 1 to 22 C atoms or an alkenyl group with 2 to 22 C atoms, R2 and R3 are independently of each other, an alkyl group with 1 to 22 C atoms, hydroxyethyl or a polyglycol moiety, X is an oxygen atom, NH, N-CH3 or a group (OC2H4) z with z> = 1 to 10, Y- is one of the CH3OSO3-, C2H5OSO3 anions -, CH3COO-, Cl-, phosphate, lactate, citrate, and m and n are, independently of one another, an integer from 1 to 6; where the quaternary ammonium compound is present as a solid at room temperature (20 ºC); (C) 15 to 50% by weight of at least one neutralized phosphoric acid ester of general formula (II): P (> = O) (OR4) (OR5) (OR6) (II) where R4, R5 and R6, independently of one another, (i) mean an alkoxylated alkyl group with 3 to 22 C atoms in the hydrocarbon chain or an alkoxylated alkenyl group with 3 to 22 C atoms in the hydrocarbon chain, in which the number of alkoxy groups per alkyl or alkylene group it is from 1 to 10, and in which the alkyl groups or alkenyl groups can be branched or linear, saturated or unsaturated, respectively; (ii) mean an alkyl group with 3 to 22 C atoms or an alkenyl group with 3 to 22 C atoms, which can be respectively branched or linear, saturated or unsaturated, and / or (iii) signify hydrogen, whereby minus one of the residues R4, R5 and R6 is not hydrogen.
Description
DESCRIPCIONDESCRIPTION
Composicion para la hidrofilizacion permanente de fibras de poliolefina y su usoComposition for permanent hydrophilization of polyolefin fibers and their use
5 La presente invencion se refiere a composiciones, preferiblemente en forma de preparaciones hiladas, para fibras o filamentos de poliolefina que confieren a estas propiedades hidrofilas permanentes de fibras en principio hidrofobas, asf como a fibras y filamentos acabados con estas composiciones y estructura textil plana fabricada a partir de los mismos, especialmente material no tejido.The present invention relates to compositions, preferably in the form of spun preparations, for polyolefin fibers or filaments that confer on these permanent hydrophilic properties of in principle hydrophobic fibers, as well as fibers and filaments finished with these compositions and manufactured flat textile structure from them, especially nonwoven material.
10 Los materiales no tejidos hidrofilos se usan como materiales no tejidos protectores, es decir, como material no tejido superior o como material no tejido intermedio de materiales no tejidos de varias capas, para artfculos higienicos como panales, compresas, productos de incontinencia y productos similares. Aquellos materiales no tejidos tienen el objetivo de conducir rapidamente fluidos corporales, como la orina, a la capa de absorcion que se encuentra debajo.10 Hydrophilic nonwoven materials are used as protective nonwoven materials, that is, as upper nonwoven material or as intermediate nonwoven material of multilayer nonwoven materials, for hygienic items such as honeycombs, compresses, incontinence products and similar products . Those non-woven materials are intended to quickly lead body fluids, such as urine, to the absorption layer underneath.
15 Las preparaciones hidrofilizantes habituales se eliminan del material no tejido mas o menos rapido y mas o menos fuertemente mediante el transporte de lfquidos dentro del panal u otro producto. De esta manera, el material no tejido protector pierde poco a poco sus propiedades hidrofilas y, debido a las propiedades hidrofobas de las poliolefinas, es cada vez mas hidrofobo. En el posterior contacto adicional con fluidos corporales, su conduccion a la capa de absorcion se dificulta cada vez mas y finalmente es completamente imposible. La consecuencia es que los 20 lfquidos se fugan de la construccion de material no tejido y que la construccion de material no tejido ya no puede desempenar su funcion original, mantener seca la piel de un bebe o de un paciente.15 The usual hydrophilizing preparations are removed from the nonwoven material more or less quickly and more or less strongly by transporting liquids within the honeycomb or other product. In this way, the protective nonwoven material gradually loses its hydrophilic properties and, due to the hydrophobic properties of polyolefins, it is increasingly hydrophobic. In the subsequent additional contact with body fluids, its conduction to the absorption layer becomes increasingly difficult and is finally completely impossible. The consequence is that the 20 liquids escape from the construction of non-woven material and that the construction of non-woven material can no longer perform its original function, keeping the skin of a baby or a patient dry.
Por el contrario, una preparacion para la hidrofilizacion permanente debera permanecer adherida lo mas duraderamente posible sobre la poliolefina y conferir al material no tejido una hidrofilia lo mas constante posible 25 durante un periodo de tiempo lo mas largo posible.On the contrary, a preparation for permanent hydrophilization should remain as durable as possible on the polyolefin and give the non-woven material as constant hydrophilicity as possible for a period of time as long as possible.
Normalmente, la formacion de un material no tejido se realiza de filamentos y/o fibras, fijandose los materiales no tejidos de fibra de orientacion aleatoria bien mediante procedimientos ffsicos como agujeteado o bien de forma qufmica. En la produccion de materiales no tejidos cardados, que a continuacion se termofijan, una preparacion de 30 fibra hidrofilizante debe cumplir ademas todavfa otros requisitos. La preparacion debe en este caso hacer posible la preparacion y procesamiento de las fibras y ademas proporcionar propiedades de deslizamiento optimas y cohesion de las fibras o filamentos, asf como un acabado antiestatico suficiente, para poder realizar la formacion de materiales no tejidos con velocidad aceptable.Normally, the formation of a non-woven material is made of filaments and / or fibers, the non-woven materials of random orientation fiber being fixed either by physical procedures such as punching or chemically. In the production of carded nonwoven materials, which are then thermofixed, a preparation of hydrophilicizing fiber must also meet other requirements. The preparation must in this case make possible the preparation and processing of the fibers and also provide optimum sliding properties and cohesion of the fibers or filaments, as well as a sufficient antistatic finish, to be able to perform the formation of nonwoven materials with acceptable speed.
35 La patente de EE.UU. 4 988 449 describe composiciones hidrofilizantes que contienen dietanolamidas, asf como tensioactivos no ionicos, alquilfosfatos, sales de amonio cuaternarias y/o sales de alquilimidazolio, y se utilizan como agentes que confieren permeabilidad a los lfquidos para no tejidos de poliolefina.35 U.S. Patent No. 4,988,449 describes hydrophilizing compositions containing diethanolamides, as well as non-ionic surfactants, alkyl phosphates, quaternary ammonium salts and / or alkylimidazolium salts, and are used as agents that confer liquid permeability to polyolefin nonwovens.
Por el documento US 5 258 129 se conocen composiciones hidrofilizantes que contienen polidimetilsiloxanos 40 modificados con polioxialquileno solos o en combinacion con tensioactivos no ionicos, alquilfosfatos, sales de amonio cuaternarias y/o sales de alquilimidazolio.From US 5 258 129, hydrophilizing compositions containing polydimethylsiloxanes modified with polyoxyalkylene alone or in combination with non-ionic surfactants, alkyl phosphates, quaternary ammonium salts and / or alkylimidazolium salts are known.
El documento EP 410 485 B1 da a conocer un procedimiento para la hidrofilizacion de materiales no tejidos de fibra de poliolefina mediante la aplicacion de una mezcla acuosa de tensioactivos alcoxilados sobre la superficie de las 45 fibras, donde la composicion esta constituida o bien por hasta al menos el 80 % de trigliceridos alcoxilados de acidos grasos C18, presentando estos trigliceridos una gran proporcion de ricinolefna alcoxilada o ricinolefna alcoxilada e hidrogenada, o bien hasta al menos el 80 % de una mezcla de ricinolefna alcoxilada o alcoxilada e hidrogenada, un polidimetilsiloxano soluble en agua modificado con polialquileno y un compuesto antiestatico, pudiendo ser el ultimo, por ejemplo, un ester de acido fosforico neutralizado, un fosfato alcoxilado, sal de potasio, sal de amonio o una sal 50 de amonio alquioxilada.EP 410 485 B1 discloses a process for the hydrophilization of nonwoven polyolefin fiber materials by applying an aqueous mixture of alkoxylated surfactants on the surface of the fibers, where the composition is constituted or by up to minus 80% of alkoxylated triglycerides of C18 fatty acids, these triglycerides having a large proportion of alkoxylated ricinolefna or alkoxylated and hydrogenated ricinolefna, or up to at least 80% of a mixture of alkoxylated or alkoxylated and hydrogenated ricinolefna, a soluble dimethyl siloxane water modified with polyalkylene and an antistatic compound, the latter being, for example, a neutralized phosphoric acid ester, an alkoxylated phosphate, potassium salt, ammonium salt or an alkyloxylated ammonium salt.
Por el documento EP 0 839 947 A2 se conocen composiciones hidrofilizantes que contienen tensioactivos no ionicos en combinacion con un polidimetilsiloxano modificado con polioxialquileno y/o un compuesto de amonio cuaternario.From EP 0 839 947 A2, hydrophilizing compositions containing non-ionic surfactants in combination with a polyoxyalkylene modified polydimethylsiloxane and / or a quaternary ammonium compound are known.
55 El documento EP 1 600 532 B1 describe composiciones hidrofilizantes que estan constituidas por una glicerina alcoxilada esterificada con un acido graso y una ricinolefna alcoxilada o alcoxilada e hidrogenada esterificada con un acido graso.EP 1 600 532 B1 describes hydrophilicizing compositions that are constituted by an alkoxylated glycerin esterified with a fatty acid and an alkoxylated or alkoxylated and hydrogenated ricinolephine esterified with a fatty acid.
Aunque estas composiciones conocidas confieren a las fibras y materiales no tejidos de fibra asf tratados oAlthough these known compositions confer on treated fibers and nonwoven fibers asf or
acabados propiedades hidrofilas permanentes, son caras en la produccion y necesitan ser mejoradas en lo referente a la velocidad a la que el lfquido se conduce a traves del material no tejido en la capa de absorcion. Ademas, existe la necesidad de composiciones para el acabado hidrofilizante de fibras y materiales no tejidos que sean resistentes a una migracion de los constituyentes de la preparacion en el estado seco y/o humedo a zonas de material no tejido 5 hidrofobo adyacentes.Finished permanent hydrophilic properties are expensive in production and need to be improved in relation to the speed at which the liquid is conducted through the nonwoven material in the absorption layer. In addition, there is a need for compositions for the hydrophilizing finish of fibers and nonwoven materials that are resistant to a migration of the constituents of the preparation in the dry and / or wet state to adjacent non-woven areas of hydrophobic material.
Por lo tanto, la invencion se basa en el objetivo de proporcionar una composicion con buenas propiedades hidrofilizantes permanentes, asf como una rapida capacidad de transito y una tendencia mas baja a la migracion en zonas de material no tejido hidrofobo adyacentes.Therefore, the invention is based on the objective of providing a composition with good permanent hydrophilizing properties, as well as rapid transit capacity and a lower tendency to migrate in areas of adjacent non-woven hydrophobic material.
1010
Este objetivo se alcanza segun la invencion por una composicion para la hidrofilizacion permanente de fibras y filamentos de poliolefina y estructuras textiles planas fabricadas a partir de los mismos como materiales no tejidos y otros productos textiles no tejidos (no tejidos) de acuerdo con la reivindicacion 1.This objective is achieved according to the invention by a composition for permanent hydrophilization of polyolefin fibers and filaments and flat textile structures manufactured therefrom as nonwoven materials and other nonwoven (nonwoven) textile products according to claim 1 .
15 Formas de realizacion ventajosas adicionales se especifican en las reivindicaciones dependientes que opcionalmente pueden combinarse entre sLAdditional advantageous embodiments are specified in the dependent claims that can optionally be combined between sL
La composicion segun la invencion para la hidrofilizacion permanente de fibras y filamentos de poliolefina y estructuras textiles planas fabricadas a partir de los mismos contiene:The composition according to the invention for the permanent hydrophilization of polyolefin fibers and filaments and flat textile structures manufactured therefrom contains:
20twenty
(A) 15 al 50% en peso de al menos un tensioactivo no ionico, donde el tensioactivo no ionico se selecciona del siguiente grupo de compuestos que presentan respectivamente una o varias cadenas de hidrocarburo C6-C18 ramificadas o de cadena lineal, saturadas o insaturadas en su molecula: alcoholes grasos C6-C18 alcoxilados, aminas C6-C18 alcoxiladas, amidas C6-C18 alcoxiladas, acidos C6-C18 grasos alcoxilados,(A) 15 to 50% by weight of at least one non-ionic surfactant, wherein the non-ionic surfactant is selected from the following group of compounds that respectively have one or more branched or straight-chain C6-C18 hydrocarbon chains, saturated or unsaturated in its molecule: alkoxylated C6-C18 fatty alcohols, alkoxylated C6-C18 amines, alkoxylated C6-C18 amides, alkoxylated C6-C18 fatty acids,
25 esteres de acidos grasos C6-C18 alcoxilados y alquilfenoles C8-C18 alcoxilados;25 esters of alkoxylated C6-C18 fatty acids and alkoxylated C8-C18 alkylphenols;
(B) 15 al 50% en peso de al menos un compuesto de amonio cuaternario de formula general (I):(B) 15 to 50% by weight of at least one quaternary ammonium compound of general formula (I):
[R1-C(=O)-X-(CH2)n-NR2R3-(CH2)m-X-C(=O)-R1]+ Y' (I)[R1-C (= O) -X- (CH2) n-NR2R3- (CH2) m-X-C (= O) -R1] + Y '(I)
dondewhere
R1 significa un grupo alquilo con 1 a 22 atomos de C o un grupo alquenilo con 2 a 22R1 means an alkyl group with 1 to 22 atoms of C or an alkenyl group with 2 to 22
atomos de C,C atoms,
R2 y R3, independientemente entre sf, un grupo alquilo con 1 a 22 atomos de C, hidroxietilo o unR2 and R3, independently from each other, an alkyl group with 1 to 22 C atoms, hydroxyethyl or a
resto de poliglicol,rest of polyglycol,
X un atomo de oxfgeno, NH, N-CH3 o un grupo (OC2H4)z con z = 1 a 10,X an atom of oxygen, NH, N-CH3 or a group (OC2H4) z with z = 1 to 10,
Y' uno de los aniones CH3OSO3", C2H5OSO3", CH3C0O', Cl-, fosfato, lactato, citrato, yAnd 'one of the anions CH3OSO3 ", C2H5OSO3", CH3C0O', Cl-, phosphate, lactate, citrate, and
m y n, independientemente entre sf, un numero entero de 1 a 6;m and n, independently of each other, an integer from 1 to 6;
donde el compuesto de amonio cuaternario esta presente como solido a temperatura ambiente (20 °C);where the quaternary ammonium compound is present as a solid at room temperature (20 ° C);
40 (C) 15 al 50% en peso de al menos un ester de acido fosforico neutralizado de formula general (II):40 (C) 15 to 50% by weight of at least one neutralized phosphoric acid ester of general formula (II):
P(=O)(OR4)(OR5)(OR6) (II)P (= O) (OR4) (OR5) (OR6) (II)
3030
3535
45Four. Five
50fifty
5555
dondewhere
R4, R5 y R6 , independientemente entre sf,R4, R5 and R6, independently between sf,
(i) significan un grupo alquilo alcoxilado con 3 a 22 atomos de C en la cadena de hidrocarburo o un grupo alquenilo alcoxilado con 3 a 22 atomos de C en la cadena de hidrocarburo, en los que el numero de grupos alcoxi por grupo alquilo o alquileno asciende a de 1 a 10, y en los que los grupos alquilo o grupos alquenilo pueden ser respectivamente ramificados o lineales, saturados o insaturados;(i) means an alkoxylated alkyl group with 3 to 22 C atoms in the hydrocarbon chain or an alkoxylated alkenyl group with 3 to 22 C atoms in the hydrocarbon chain, in which the number of alkoxy groups per alkyl group or alkylene amounts to 1 to 10, and in which the alkyl groups or alkenyl groups can be respectively branched or linear, saturated or unsaturated;
(ii) significan un grupo alquilo con 3 a 22 atomos de C o un grupo alquenilo con 3 a 22 atomos de C, que pueden ser respectivamente ramificados o lineales, saturados o insaturados, y/o(ii) means an alkyl group with 3 to 22 C atoms or an alkenyl group with 3 to 22 C atoms, which can be respectively branched or linear, saturated or unsaturated, and / or
(iii) significan hidrogeno,(iii) mean hydrogen,
donde por lo menos uno de los restos R4, R5 y R6 no es hidrogeno.where at least one of the residues R4, R5 and R6 is not hydrogen.
Como agente de neutralizacion para el ester de acido fosforico pueden usarse todas las bases adecuadas como, por ejemplo, LiOH, NaOH, KOH, NH3, mono-, di- o trietanolamina.As the neutralizing agent for the phosphoric acid ester, all suitable bases such as, for example, LiOH, NaOH, KOH, NH3, mono-, di- or triethanolamine can be used.
La composicion segun la invencion posee excelentes propiedades hidrofilizantes permanentes, una excelente capacidad de transito y una buena resistencia a la migracion de los constituyentes de la preparacion a zonas de material no tejido hidrofobo adyacente.The composition according to the invention has excellent permanent hydrophilizing properties, excellent transit capacity and good resistance to the migration of the constituents of the preparation to areas of adjacent non-woven hydrophobic material.
5 Estas composiciones pueden usarse especialmente bien en dilucion acuosa como preparaciones de fibra para el acabado hidrofilo permanente de fibras de poliolefina, filamentos de poliolefina y no tejidos fabricados a partir de los mismos, especialmente materiales no tejidos.5 These compositions can be used especially well in aqueous dilution as fiber preparations for permanent hydrophilic finishing of polyolefin fibers, polyolefin filaments and nonwovens manufactured therefrom, especially nonwoven materials.
El tensioactivo no ionico en el componente (A) de la composicion segun la invencion esta seleccionado 10 preferiblemente del grupo de alcoxilatos de alcohol graso con 6 a 18 atomos de C en la cadena de hidrocarburo. Se prefieren especialmente alcoxilatos de alcohol graso con 8 a 16 atomos de C en la cadena de hidrocarburo.The nonionic surfactant in component (A) of the composition according to the invention is preferably selected from the group of fatty alcohol alkoxylates with 6 to 18 C atoms in the hydrocarbon chain. Especially preferred are fatty alcohol alkoxylates with 8 to 16 C atoms in the hydrocarbon chain.
Los alcoxilatos de alcohol graso pueden presentar terminalmente un grupo hidroxilo o uno alquilo, o alquenil eter. Se prefieren especialmente alcoxilatos de alcohol graso terminados con grupos hidroxi.The fatty alcohol alkoxylates may terminally have a hydroxyl group or an alkyl group, or alkenyl ether. Especially preferred are fatty alcohol alkoxylates terminated with hydroxy groups.
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El numero de grupos alcoxi en el tensioactivo no ionico del componente (A) asciende preferiblemente a de 1 a 10, preferiblemente de 2 a 8, y con especial preferencia de 2 a 6. Los grupos alcoxi son preferiblemente grupos etil(en)oxi (EO) y/o propil(en)oxi (PO), con especial preferencia grupos EO.The number of alkoxy groups in the non-ionic surfactant of component (A) is preferably from 1 to 10, preferably from 2 to 8, and especially preferably from 2 to 6. Alkoxy groups are preferably ethyl (en) oxy groups ( EO) and / or propyl (en) oxy (PO), with particular preference EO groups.
20 En el compuesto de amonio cuaternario del componente (B), los restos R1 a R3 en la formula (I) significan preferiblemente grupos alquilo como se derivan de aceites vegetales y mezclas de aceites. Con especial preferencia, los restos R1, R2 y R3 se derivan de aceites vegetales con una alta proporcion de acidos grasos saturados, especialmente de aceite de palma o aceite de semilla de palma.In the quaternary ammonium compound of component (B), residues R1 to R3 in formula (I) preferably mean alkyl groups as derived from vegetable oils and oil mixtures. With particular preference, residues R1, R2 and R3 are derived from vegetable oils with a high proportion of saturated fatty acids, especially palm oil or palm kernel oil.
25 Los compuestos de amonio cuaternarios estan presentes a temperatura ambiente como solidos segun la invencion.The quaternary ammonium compounds are present at room temperature as solids according to the invention.
Segun una forma de realizacion especialmente preferida de la composicion segun la invencion, los compuestos de amonio cuaternarios presentan un punto de fusion de 25 a 80 °C, con especial preferencia un punto de fusion de 30 a 50 °C.According to a particularly preferred embodiment of the composition according to the invention, quaternary ammonium compounds have a melting point of 25 to 80 ° C, especially a melting point of 30 to 50 ° C.
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Por lo menos uno de los restos R4, R5 y R6 en la formula (II) del ester de acido fosforico neutralizado del componenteAt least one of the residues R4, R5 and R6 in formula (II) of the neutralized phosphoric acid ester of the component
(C) es preferiblemente un grupo alquilo o alquenilo alcoxilado con 6 a 18 atomos de C en la cadena de hidrocarburo y 1 a 6 grupos alcoxi, con especial preferencia un grupo alquilo o alquenilo alcoxilado con 10 a 18 atomos de C en la cadena de hidrocarburo y 1 a 4 grupos alcoxi. Los grupos alcoxi son preferiblemente grupos etil(en)oxi (EO) y/o 35 propil(en)oxi (PO), con especial preferencia grupos EO.(C) is preferably an alkoxylated alkyl or alkenyl group with 6 to 18 C atoms in the hydrocarbon chain and 1 to 6 alkoxy groups, especially preferably an alkoxylated alkyl or alkenyl group with 10 to 18 C atoms in the chain of hydrocarbon and 1 to 4 alkoxy groups. The alkoxy groups are preferably ethyl (en) oxy (EO) and / or propyl (en) oxy (PO) groups, especially preferably EO groups.
Segun otra forma de realizacion preferida, por lo menos uno de los restos R4, R5 y R6 en la formula (II) es un grupo alquilo o un grupo alquenilo con 6 a 18 atomos de C, con especial preferencia con 10 a 18 atomos de C.According to another preferred embodiment, at least one of the residues R4, R5 and R6 in formula (II) is an alkyl group or an alkenyl group with 6 to 18 atoms of C, especially preferably with 10 to 18 atoms of C.
40 Adicionalmente, la composicion segun la invencion puede contener como componente (D) opcionalmente aditivos adicionales del grupo de los agentes de cohesion, lubricantes, inhibidores de la corrosion y emulsionantes.Additionally, the composition according to the invention may optionally contain as component (D) additional additives from the group of cohesion agents, lubricants, corrosion inhibitors and emulsifiers.
La composicion segun la invencion esta constituida preferiblemente por los componentes (A), (B) y (C), asf como opcionalmente por uno o varios de los aditivos segun el componente (D). Con especial preferencia, el componente 45 (A) esta presente en una proporcion del 20-35 % en peso, el componente (B) en una proporcion del 25-35 % en peso y el componente (C) en una proporcion del 35-45 % en peso, respectivamente referido al peso total de los componentes (A), (B) y (C).The composition according to the invention is preferably constituted by components (A), (B) and (C), as well as optionally by one or more of the additives according to component (D). With particular preference, component 45 (A) is present in a proportion of 20-35% by weight, component (B) in a proportion of 25-35% by weight and component (C) in a proportion of 35- 45% by weight, respectively referred to the total weight of the components (A), (B) and (C).
Los aditivos adicionales del componente (D) pueden anadirse tanto a la composicion segun la invencion constituida 50 por los componentes (A), (B) y (C), como tambien al lfquido de aplicacion.Additional additives of component (D) can be added both to the composition according to the invention constituted by components (A), (B) and (C), as well as to the application liquid.
Como agentes de cohesion se usa preferiblemente un alcoxilato de ricino, por ejemplo, Emulsogen EL 360 de Clariant, o un alcoxilato de ricino con hasta 10 unidades de etoxi y hasta 3 de propoxi. La proporcion de agente de cohesion en la composicion segun la invencion asciende preferiblemente a del 1 al 10% en peso, referido al peso 55 total de la composicion.As cohesion agents a castor alkoxylate is preferably used, for example, Clariant Emulsogen EL 360, or a castor alkoxylate with up to 10 ethoxy units and up to 3 propoxy units. The proportion of cohesion agent in the composition according to the invention preferably amounts to 1 to 10% by weight, based on the total weight of the composition.
El agente de cohesion se anade preferiblemente posteriormente al lfquido de aplicacion.The cohesion agent is preferably added subsequently to the application liquid.
El lubricante es preferiblemente un etoxilato de acido graso, con especial preferencia un alquioxilato de acido grasoThe lubricant is preferably a fatty acid ethoxylate, especially preferably a fatty acid alkoxylate
de coco como, por ejemplo, Genagen C100 de Clariant, un acido graso de coco con hasta 10 unidades de etoxi, o un acido graso de coco con hasta 10 unidades de etoxi y 3 de propoxi. La proporcion de lubricante en la composicion segun la invencion asciende preferiblemente a del 1 al 10% en peso, referido al peso total de la composicion.of coconut, such as Geniant C100 from Clariant, a coconut fatty acid with up to 10 units of ethoxy, or a coconut fatty acid with up to 10 units of ethoxy and 3 units of propoxy. The proportion of lubricant in the composition according to the invention preferably amounts to 1 to 10% by weight, based on the total weight of the composition.
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Con especial preferencia, el lubricante se anade posteriormente al lfquido de aplicacion.With special preference, the lubricant is subsequently added to the application liquid.
Como inhibidores de la corrosion para la proteccion de las piezas metalicas de las maquinas de hilado y de las otras maquinas de procesamiento, por ejemplo de las cardas, se usa preferiblemente un derivado de amina de acido 10 graso. Especialmente preferido, el inhibidor de la corrosion es un sarcosinato de oleflo. La proporcion de inhibidor de la corrosion en la composicion segun la invencion asciende preferiblemente a del 0 al 2 % en peso, referido al peso total de la composicion.As corrosion inhibitors for the protection of the metal parts of the spinning machines and other processing machines, for example of the cards, a fatty acid amine derivative is preferably used. Especially preferred, the corrosion inhibitor is an oleflo sarcosinate. The proportion of corrosion inhibitor in the composition according to the invention preferably amounts to 0 to 2% by weight, based on the total weight of the composition.
Preferiblemente, el inhibidor de la corrosion se anade posteriormente al lfquido de aplicacion.Preferably, the corrosion inhibitor is subsequently added to the application liquid.
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Como emulsionante tambien se usa preferiblemente un etoxilato de acido graso, con especial preferencia un alquioxilato de acido graso de coco como Genagen C100 de Clariant, un acido graso de coco con hasta 10 unidades de etoxi, o un acido graso de coco con hasta 10 unidades de etoxi y 3 de propoxi. La proporcion de emulsionante en la composicion segun la invencion asciende preferiblemente a del 1 al 50 % en peso, referido al peso total de la 20 composicion.As an emulsifier, a fatty acid ethoxylate is also preferably used, especially a coconut fatty acid alkoxylate such as Clariant Genagen C100, a coconut fatty acid with up to 10 units of ethoxy, or a coconut fatty acid with up to 10 units of ethoxy and 3 of propoxy. The proportion of emulsifier in the composition according to the invention preferably amounts to 1 to 50% by weight, based on the total weight of the composition.
La composicion segun la invencion esta presente preferiblemente en forma de una dispersion acuosa o pasta, cuyo residuo de secado a 105 °C asciende a entre el 5 y el 95 % en peso.The composition according to the invention is preferably present in the form of an aqueous dispersion or paste, whose drying residue at 105 ° C amounts to between 5 and 95% by weight.
25 La composicion segun la invencion se usa preferiblemente como preparacion de fibra hidrofilizante permanente para fibras de poliolefina o filamentos de poliolefina o bien como agente para el acabado hidrofilo permanente de estructuras textiles planas no tejidas (no tejidos) fabricadas a partir de fibras de poliolefina o filamentos de poliolefina.The composition according to the invention is preferably used as a preparation of permanent hydrophilicizing fiber for polyolefin fibers or polyolefin filaments or as an agent for permanent hydrophilic finishing of flat nonwoven (nonwoven) textile structures made from polyolefin fibers or polyolefin filaments.
30 Como poliolefina puede utilizarse preferiblemente homo- o copolfmeros basados en etileno o propileno.As the polyolefin, homo- or copolymers based on ethylene or propylene can preferably be used.
Ejemplos de aquellas poliolefinas son polietilenos como HDPE (polietileno de alta densidad), LDPE (polietileno de baja densidad), VLDPE (polietileno de densidad muy baja), LLDPE (polietileno lineal de densidad baja), MDPE (polietileno de densidad media), UHMPE (polietileno de peso molecular ultra-alto), VPE (polietileno reticulado), 35 HPPE (polietileno de alta presion); polipropileno como polipropileno isotactico; polipropileno sindiotactico, polipropileno fabricado catalizado por metaloceno, polipropileno modificado con resistencia al impacto; copolfmeros al azar basados en etileno y propileno, copolfmeros de bloque basados en etileno y propileno; ePm (poli[etileno-co- propileno]); EPDM (poli[etileno-co-propileno-dieno conjugado]).Examples of those polyolefins are polyethylenes such as HDPE (high density polyethylene), LDPE (low density polyethylene), VLDPE (very low density polyethylene), LLDPE (linear low density polyethylene), MDPE (medium density polyethylene), UHMPE (ultra-high molecular weight polyethylene), VPE (cross-linked polyethylene), HPPE (high pressure polyethylene); polypropylene as isotactic polypropylene; syndiotactic polypropylene, fabricated metallocene catalyzed polypropylene, modified impact resistant polypropylene; random copolymers based on ethylene and propylene, block copolymers based on ethylene and propylene; ePm (poly [ethylene-co-propylene]); EPDM (poly [ethylene-co-propylene-conjugated diene]).
40 Poliolefinas adecuadas adicionales son, por ejemplo, poliestireno; poli(metilestireno); poli(oximetileno); copolfmeros de alfa-olefina o cicloolefina catalizados con metaloceno como copolfmeros de norborneno-etileno; copolfmeros que contienen hasta al menos el 60 % de etileno y/o estireno y hasta menos del 40 % de monomero como acetato de vinilo, esteres de acido acrflico, esteres de acido metacrflico, acido acrflico, acrilonitrilo o cloruro de vinilo. Ejemplos de tales polfmeros son poli(etileno-co-acrilato de etilo), poli(etileno-co-acetato de vinilo), poli(etileno-co-cloruro de 45 vinilo) y poli(estireno-co-acrilonitrilo).Additional suitable polyolefins are, for example, polystyrene; poly (methylstyrene); poly (oxymethylene); alpha-olefin or cycloolefin copolymers catalyzed with metallocene such as norbornene-ethylene copolymers; Copolymers containing up to at least 60% ethylene and / or styrene and up to less than 40% monomer such as vinyl acetate, acrylic acid esters, methacrylic acid esters, acrylic acid, acrylonitrile or vinyl chloride. Examples of such polymers are poly (ethylene-ethyl co-acrylate), poly (ethylene-co-vinyl acetate), poly (ethylene-co-vinyl chloride) and poly (styrene-co-acrylonitrile).
Son adecuados ademas copolfmeros de injerto, asf como mezclas de polfmeros, es decir, mezclas de polfmeros en las que estan contenidas, entre otros, los polfmeros previamente mencionados, por ejemplo, mezclas de polfmeros basadas en polietileno y polipropileno. Ademas, pueden usarse fibras bicomponente con estructura de 50 nucleo/envoltura como biopolfmeros de PE/PP y PP/PET.In addition, graft copolymers are suitable, as well as mixtures of polymers, that is, mixtures of polymers in which the aforementioned polymers are included, for example, mixtures of polymers based on polyethylene and polypropylene. In addition, bicomponent fibers with a 50 core / shell structure can be used as PE / PP and PP / PET biopolymers.
La composicion segun la invencion puede aplicarse en forma de una emulsion acuosa o en forma de una dispersion acuosa sobre las fibras, filamentos o no tejidos, y concretamente preferiblemente en una cantidad del 0,1 al 2 % referido al peso seco del producto respetivo (fibra, filamento, material no tejido).The composition according to the invention can be applied in the form of an aqueous emulsion or in the form of an aqueous dispersion on the fibers, filaments or nonwovens, and particularly preferably in an amount of 0.1 to 2% based on the dry weight of the respective product ( fiber, filament, nonwoven material).
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La aplicacion de la composicion se realiza, como conoce el experto, mediante varillas dosificadoras, rodillos de recubrimiento inferior, banos de inmersion o mediante pulverizacion. Mediante la dilucion de la composicion con agua puede ajustarse la viscosidad deseada para la forma de aplicacion respectiva.The application of the composition is carried out, as the expert knows, by means of dosing rods, lower coating rollers, immersion baths or by spraying. By diluting the composition with water, the desired viscosity can be adjusted for the respective application form.
Por tanto, tambien son objeto de la invencion fibras y filamentos de poliolefina que se acaban o tratan de forma hidrofila permanente con la composicion segun la invencion.Therefore, polyolefin fibers and filaments that are finished or treated permanently with the composition according to the invention are also subject to the invention.
La invencion tambien comprende un acabado doble y tratamiento de fibras y filamentos de poliolefina y no tejidos, en 5 los que inicialmente las fibras o filamentos se acaban de forma hidrofila permanente y a continuacion el no tejido o material no tejido fabricado a partir de estos se acaba en total de nuevo de forma hidrofila permanente con una composicion segun la invencion.The invention also comprises a double finish and treatment of fibers and filaments of polyolefin and nonwovens, in which initially the fibers or filaments are finished in a permanent hydrophilic manner and then the nonwoven or nonwoven material manufactured therefrom is finished. in total again in a permanent hydrophilic way with a composition according to the invention.
En el caso de los materiales no tejidos acabados segun la invencion se trata con especial preferencia de materiales 10 no tejidos de fibra de orientacion aleatoria no comprimidos o de qufmicamente o ffsicamente fijados, por ejemplo, agujeteados o termofijados.In the case of finished nonwoven materials according to the invention, special preference is given to non-woven, non-compressed or chemically or physically fixed non-woven fiber materials, for example, punched or thermofixed.
La invencion se explica a continuacion mediante algunas formas de realizacion preferidas que, sin embargo, no deben entenderse en un sentido limitante.The invention is explained below by some preferred embodiments, which, however, should not be understood in a limiting sense.
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Ejemplo 1Example 1
Componente AComponent A
20 34,2 % en peso de eter de polietilenglicol de alcohol graso C10-4EO (tensioactivo no ionico)20 34.2% by weight of C10-4EO fatty alcohol polyethylene glycol ether (non-ionic surfactant)
Componente BComponent B
28,2 % en peso de di-(palmcarboxietil)-hidroxietil-metilamonio-metosulfato (de compuesto de amonio cuaternario 25 derivado de aceite graso de palma; punto de fusion a partir de 35 °C)28.2% by weight of di- (palmcarboxyethyl) -hydroxyethyl-methylammonium-methosulfate (of quaternary ammonium compound 25 derived from palm oil; melting point from 35 ° C)
Componente CComponent C
37,6 % en peso de ester de acido mono- y di-alquil (C12-C18)-fosforico, sal de potasio 3037.6% by weight of mono- and di (C12-C18) -phosphoric acid ester, potassium salt 30
Los componentes A, B y C se mezclaron cuidadosamente entre si, se homogeneizaron y opcionalmente se neutralizaron. Luego, la composicion asf obtenida se diluyo con agua destilada o desmineralizada con formacion de una dispersion que contuvo 5 % en peso de la composicion.Components A, B and C were carefully mixed together, homogenized and optionally neutralized. Then, the composition thus obtained was diluted with distilled or demineralized water with the formation of a dispersion containing 5% by weight of the composition.
35 Ejemplo 235 Example 2
Componente AComponent A
24.1 % en peso de eter de polietilenglicol de alcohol graso C12-C14-(3EO)24.1% by weight of C12-C14- (3EO) fatty alcohol polyethylene glycol ether
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Componente BComponent B
32,0 % en peso de di-(palmcarboxietil)-hidroxietil-metilamonio-metosulfato 45 Componente C32.0% by weight of di- (palmcarboxyethyl) -hydroxyethyl-methylammonium-methosulfate 45 Component C
43,9 % en peso de ester de acido mono- y di-alquil (C12-C18)-fosforico, sal de potasio43.9% by weight of mono- and di (C12-C18) -phosphoric acid ester, potassium salt
Los componentes A, B y C se mezclaron cuidadosamente entre si, se homogeneizaron y opcionalmente se 50 neutralizaron. Luego, la composicion asf obtenida se diluyo con agua destilada o desmineralizada con formacion de una dispersion que contuvo 5 % en peso de la composicion.Components A, B and C were carefully mixed together, homogenized and optionally neutralized. Then, the composition thus obtained was diluted with distilled or demineralized water with the formation of a dispersion containing 5% by weight of the composition.
Ejemplo comparativo 1Comparative Example 1
55 Componente A55 Component A
34.2 % en peso de bis-isooctilsulfosuccinato de sodio (tensioactivo ionico)34.2% by weight of sodium bis-isooctylsulfosuccinate (ionic surfactant)
Componente BComponent B
28.2 % en peso de di-(palmcarboxietil)-hidroxietil-metilamonio-metosulfato28.2% by weight of di- (palmcarboxyethyl) -hydroxyethyl-methylammonium-methosulfate
Componente C 5Component C 5
37.6 % en peso de ester de acido mono- y di-alquil (C12-C18)-fosforico, sal de potasio37.6% by weight of mono- and di-C (C12-C18) -phosphoric acid ester, potassium salt
Los componentes A, B y C se mezclaron cuidadosamente entre si, se homogeneizaron y opcionalmente se neutralizaron. Luego, la composicion asf obtenida se diluyo con agua destilada o desmineralizada con formacion de 10 una dispersion que contuvo 5 % en peso de la composicion.Components A, B and C were carefully mixed together, homogenized and optionally neutralized. Then, the composition thus obtained was diluted with distilled or demineralized water with formation of a dispersion containing 5% by weight of the composition.
Ejemplo comparativo 2Comparative Example 2
Componente A 15Component A 15
24,0 % en peso de eter de polietilenglicol de alcohol graso C12-C14-6EO (tensioactivo no ionico)24.0% by weight of C12-C14-6EO fatty alcohol polyethylene glycol ether (non-ionic surfactant)
Componente BComponent B
20 32,5 % en peso de di-(oleilcarboxietil)-hidroxietil-metilamonio-metosulfato (compuesto de amonio cuaternario; punto de fusion inferior a 20 °C)20 32.5% by weight of di- (oleylcarboxyethyl) -hydroxyethyl-methylammonium-methyl sulfate (quaternary ammonium compound; melting point below 20 ° C)
Componente CComponent C
25 43,5 % en peso de ester de acido mono- y di-alquil (C12-C18)-fosforico, sal de potasio43.5.5% by weight of mono- and di-alkyl (C12-C18) -phosphoric acid ester, potassium salt
Los componentes A, B y C se mezclaron cuidadosamente entre si, se homogeneizaron y opcionalmente se neutralizaron. Luego, la composicion asf obtenida se diluyo con agua destilada o desmineralizada con formacion de una dispersion que contuvo 5 % en peso de la composicion.Components A, B and C were carefully mixed together, homogenized and optionally neutralized. Then, the composition thus obtained was diluted with distilled or demineralized water with the formation of a dispersion containing 5% by weight of the composition.
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Ejemplo comparativo 3Comparative Example 3
Componente AComponent A
35 34,2 % en peso de bis-isooctilsulfosuccinato de sodio (tensioactivo ionico)35 34.2% by weight of sodium bis-isooctylsulfosuccinate (ionic surfactant)
Componente BComponent B
28.2 % en peso de di-(oleilcarboxietil)-hidroxietil-metilamonio-metosulfato 4028.2% by weight of di- (oleylcarboxyethyl) -hydroxyethyl-methylammonium-methosulfate 40
Componente CComponent C
37.6 % en peso de ester de acido mono- y di-alquil (C12-C18)-fosforico, sal de potasio37.6% by weight of mono- and di-C (C12-C18) -phosphoric acid ester, potassium salt
45 Los componentes A, B y C se mezclaron cuidadosamente entre si, se homogeneizaron y opcionalmente se neutralizaron. Luego, la composicion asf obtenida se diluyo con agua destilada o desmineralizada con formacion de una dispersion que contuvo 5 % en peso de la composicion.The components A, B and C were carefully mixed together, homogenized and optionally neutralized. Then, the composition thus obtained was diluted with distilled or demineralized water with the formation of a dispersion containing 5% by weight of the composition.
Ejemplo comparativo 4Comparative Example 4
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Como muestra adicional se uso una preparacion de fibra hidrofilizante permanente de Schill + Seilacher GmbH, Boblingen, que puede obtenerse en el comercio con la denominacion Silastol PHP 20 y esta constituida esencialmente por una mezcla de antiestaticos cationicos, emulsionantes no ionogenos y humectantes especiales.As an additional sample, a permanent hydrophilicizing fiber preparation from Schill + Seilacher GmbH, Boblingen was used, which can be obtained commercially under the name Silastol PHP 20 and is essentially constituted by a mixture of cationic antistatics, non-ionogenic emulsifiers and special humectants.
55 Ejemplo comparativo 555 Comparative Example 5
Se produjo una preparacion de fibra segun las composiciones descritas en el documento US 4 988 449 que estuvo constituida por una alquildietanolamida, una sal acida de un ester de acido alquifosforico, un tensioactivo no ionico y un polidimetilsiloxano modificado cuaternario.A fiber preparation was produced according to the compositions described in US 4 988 449 which was constituted by an alkyldiethanolamide, an acid salt of an alkylophosphoric acid ester, a non-ionic surfactant and a quaternary modified polydimethylsiloxane.
Ejemplo comparativo 6Comparative Example 6
Como muestra adicional se uso una preparacion de fibra hidrofilizante permanente basada en esteres de 5 polietilenglicol de acido graso, que puede obtenerse en el comercio con la denominacion Stantex™ S 6327 (Pulcra Chemicals).As an additional sample, a permanent hydrophilicizing fiber preparation based on fatty acid polyethylene glycol esters was used, which can be obtained commercially under the designation Stantex ™ S 6327 (Pulcra Chemicals).
Investigacion de propiedades hidrofilizantesInvestigation of hydrophilizing properties
10 Todas las preparaciones anteriormente descritas se ajustaron a una dispersion con 5 % en peso de componentes activos mediante la dilucion con agua destilada o desmineralizada. La dispersion activa al 5 % en peso de las composiciones segun los Ejemplos 1 y 2, asf como los Ejemplos comparativos 1 a 6, se usaron como preparacion de fibra para el acabado hidrofilo permanente de un material no tejido hilado de polipropileno (PP) con un gramaje de 15 g/m2. El peso aplicado de sustancia activa (OPU u Oil Pick Up), referido al peso seco del material no tejido de PP, 15 ascendio a del 0,45 al 0,65 %.10 All the preparations described above were adjusted to a dispersion with 5% by weight of active components by dilution with distilled or demineralized water. The active dispersion at 5% by weight of the compositions according to Examples 1 and 2, as well as Comparative Examples 1 to 6, were used as fiber preparation for the permanent hydrophilic finish of a spunbonded non-woven polypropylene (PP) material with a weight of 15 g / m2. The applied weight of active substance (OPU or Oil Pick Up), referred to the dry weight of the PP nonwoven, amounted to 0.45 to 0.65%.
Para la prueba de las composiciones junto con el sustrato textil mencionado se realizaron las investigaciones descritas a continuacion.For the test of the compositions together with the mentioned textile substrate, the investigations described below were carried out.
20 Tiempo de penetracion (Strike through)20 Penetration time (Strike through)
Segun el procedimiento de EDANA ERT 150.2-93, se mide el tiempo que necesitan 5 ml de una disolucion de orina sintetica para penetrar en un material no tejido preparado y llegar a la capa de absorcion de papel de filtro que se encuentra debajo. Para probar si el acabado hidrofilizante se elimina o realmente es permanentemente hidrofilizante, 25 la medicion se realiza sucesivamente cinco veces en el mismo material no tejido, renovandose respectivamente el papel de filtro de absorcion. Los cinco valores de medicion se especifican en segundos.According to the EDANA ERT 150.2-93 procedure, the time needed for 5 ml of a synthetic urine solution to penetrate a prepared nonwoven material and reach the filter paper absorption layer below is measured. To test whether the hydrophilizing finish is removed or is actually permanently hydrophilizing, the measurement is carried out successively five times on the same nonwoven material, the absorption filter paper being renewed respectively. The five measurement values are specified in seconds.
Re-mojado (Wetback)Re-wet (Wetback)
30 Segun el procedimiento de EDANA ERT 151.0-93, se mide la cantidad (en gramos) de lfquido que vuelve a fluir en un papel de filtro seco dispuesto encima a una carga de un material no tejido impregnado por un peso de 4 kg.30 According to the procedure of EDANA ERT 151.0-93, the quantity (in grams) of liquid that flows back into a dry filter paper arranged above a load of a non-woven material impregnated by a weight of 4 kg is measured.
Prueba de escurrimientoRunoff test
35 Siguiendo el ejemplo del procedimiento de EDANA 152.0-99, se dispone un material no tejido hilado de PP con una inclinacion de 45° sobre un papel de filtro que sirve de capa de absorcion. Se determina la longitud de recorrido que se necesita hasta que una cantidad definida de una disolucion de urea sintetica se condujo completamente por el material no tejido a la capa de absorcion que se encuentra debajo. Para pasar la prueba se necesita alcanzar una longitud de goteo maxima de 30 mm.35 Following the example of the EDANA 152.0-99 procedure, a spun nonwoven PP material with an inclination of 45 ° is arranged on a filter paper that serves as an absorption layer. The path length that is needed is determined until a defined amount of a synthetic urea solution was completely conducted by the nonwoven material to the absorption layer below. To pass the test you need to reach a maximum drip length of 30 mm.
4040
Prueba de diez gotasTen drops test
En la prueba de diez gotas segun un procedimiento de prueba interno de la empresa, una plantilla de metal con 10 huecos se dispone encima de un trozo de material no tejido como capa de absorcion. En cada hueco de la plantilla 45 de metal se pipetean sucesivamente 1 gota de una disolucion de orina sintetica. Un campo de prueba cuenta como pasado si la cantidad de lfquido ha sido absorbida por la capa de absorcion que se encuentra debajo en el transcurso de 2 segundos. Para obtener una declaracion sobre la permanencia de una preparacion de fibra, la prueba se repite respectivamente despues de un tiempo de espera de 3 minutos sin intercambio de la capa de absorcion. El resultado de la prueba especifica el numero de campos de prueba existentes.In the ten-drop test according to an internal test procedure of the company, a metal template with 10 holes is arranged on top of a piece of non-woven material as an absorption layer. In each hollow of the metal template 45, 1 drop of a synthetic urine solution is successively pipetted. A test field counts as if the amount of liquid has been absorbed by the absorption layer below within 2 seconds. To obtain a statement about the permanence of a fiber preparation, the test is repeated respectively after a waiting time of 3 minutes without exchange of the absorption layer. The test result specifies the number of existing test fields.
50fifty
Migracion en secoDry migration
En la migracion en seco segun un procedimiento de prueba interno de la empresa se simula una migracion de los constituyentes de la preparacion de fibra hidrofila en el material no tejido hidrofobo de alrededor. Para esto, se apilan 55 capas hidrofilas e hidrofobas alternas y se almacenen bajo presion (carga de apoyo 10 kg) a temperatura elevada de 60 °C durante 48 h. Las capas de material no tejido hidrofobo se disponen en una disolucion sintetica de orina y se evalua la humectacion de las capas de material no tejido. Idealmente no tiene lugar humectacion del material no tejido hidrofobo. La evaluacion se realiza mediante los siguientes criterios:In the dry migration according to an internal test procedure of the company simulates a migration of the constituents of the preparation of hydrophilic fiber in the surrounding non-woven hydrophobic material. For this, 55 hydrophilic layers and alternate hydrophobes are stacked and stored under pressure (support load 10 kg) at an elevated temperature of 60 ° C for 48 h. The layers of hydrophobic nonwoven material are arranged in a synthetic urine solution and the wetting of the layers of nonwoven material is evaluated. Ideally, there is no wetting of the hydrophobic nonwoven material. The evaluation is carried out using the following criteria:
Nota 1: no es visible humectacionNote 1: no moisture is visible
Nota 2: visibles como maximo 5 sitios de humedecimiento con <2 mm de diametro Nota 3: visibles 6 a 15 sitios de humedecimiento con <2 mm de diametroNote 2: visible at most 5 wetting sites with <2 mm in diameter Note 3: visible 6 to 15 wetting sites with <2 mm in diameter
Nota 4: visibles mas de 15 sitios de humedecimiento con <2 mm de diametro, o visibles sitios de humedecimiento 5 con >2 mm de diametroNote 4: visible more than 15 wetting sites with <2 mm in diameter, or visible wetting sites 5 with> 2 mm in diameter
Migracion en humedoWet Migration
En la migracion en humedo segun un procedimiento de prueba interno de la empresa se prueba el desprendimiento 10 de la preparacion de fibra y su transferencia de zonas hidrofilas a hidrofobas en contacto con un lfquido. Para esto, se dispone un trozo de material no tejido hidrofilo acabado con una preparacion de fibra en una placa de Petri con orina sintetica y encima se dispone un trozo de material no tejido hidrofobo. Despues de 30 segundos se evalua el humedecimiento del material no tejido hidrofobo. Idealmente no tiene lugar hidrofilizacion del material no tejido hidrofobo. La evaluacion se realiza mediante la especificacion de la superficie recubierta en porcentaje.In the wet migration according to an internal test procedure of the company, the detachment 10 of the fiber preparation and its transfer from hydrophilic to hydrophobic zones in contact with a liquid are tested. For this, a piece of hydrophilic nonwoven material finished with a fiber preparation in a Petri dish with synthetic urine is arranged and a piece of hydrophobic nonwoven material is disposed on top. After 30 seconds the wetting of the hydrophobic nonwoven material is evaluated. Ideally, there is no hydrophilization of the hydrophobic nonwoven material. The evaluation is carried out by specifying the surface covered in percentage.
15fifteen
Los resultados de las investigaciones realizadas obtenidos para las composiciones segun los Ejemplos 1 y 2, asf como los Ejemplos comparativos 1 a 6, se especifican en la siguiente Tabla 1, donde los valores teoricos se comparan con los valores de medicion respectivamente obtenidos. La prueba se considera pasada cuando todos los valores medidos se encuentran en el intervalo de los valores teoricos.The results of the investigations carried out for the compositions according to Examples 1 and 2, as well as Comparative Examples 1 to 6, are specified in the following Table 1, where the theoretical values are compared with the measured values respectively obtained. The test is considered passed when all measured values are in the range of theoretical values.
20twenty
Los Ejemplos 1 y 2 segun la invencion, que contienen un tensioactivo no ionico junto con un compuesto de amonio cuaternario y una mezcla de ester de acido fosforico neutralizado, cumplen los requisitos de una hidrofilizacion rapida y permanente del material no tejido de poliolefina sin migracion.Examples 1 and 2 according to the invention, which contain a non-ionic surfactant together with a quaternary ammonium compound and a neutralized phosphoric acid ester mixture, meet the requirements of a rapid and permanent hydrophilization of the nonwoven polyolefin non-migrated material.
25 Los Ejemplos comparativos 1 a 3, asf como los Ejemplos comparativos 4 a 6 comercialmente disponibles, no cumplen al menos uno de los requisitos teoricos.25 Comparative Examples 1 to 3, as well as commercially available Comparative Examples 4 to 6, do not meet at least one of the theoretical requirements.
Tabla 1: Resultados de investigacion para los Ejemplos 1 y 2, asf como los Ejemplos comparativos 1 a 6Table 1: Research results for Examples 1 and 2, as well as Comparative Examples 1 to 6
- Ejemplos Examples
- Componente A OPU [%1 Penetracion multiple [s1 Re-mojado Component A OPU [% 1 Multiple penetration [s1 Re-wet
- Teorico Theoretical
- 2/<3/<3/<3/<3 Max. 0,3 2 / <3 / <3 / <3 / <3 Max. 0.3
- Ejemplo 1 Example 1
- no ionico 0,45 1,35/2,21/2,29/2,29/2,23 0,23 non-ionic 0.45 1.35 / 2.21 / 2.29 / 2.29 / 2.23 0.23
- Ejemplo 2 Example 2
- no ionico 0,55 1,22/2,11/2,23/2,27/2,41 0,16 non-ionic 0.55 1.22 / 2.11 / 2.23 / 2.27 / 2.41 0.16
- Ejemplo comparativo 1 Comparative Example 1
- anionico 0,55 1,33/2,48/2,57/2,51/2,51 0,23 anionic 0.55 1.33 / 2.48 / 2.57 / 2.51 / 2.51 0.23
- Ejemplo comparativo 2 Comparative Example 2
- no ionico 0,45 1,24/2,18/2,56/4,20/2,63 0,22 non-ionic 0.45 1.24 / 2.18 / 2.56 / 4.20 / 2.63 0.22
- Ejemplo comparativo 3 Comparative Example 3
- anionico 0,54 1,53/2,61/2,80/2,60/2,51 0,18 anionic 0.54 1.53 / 2.61 / 2.80 / 2.60 / 2.51 0.18
- Ejemplo comparativo 4 Comparative Example 4
- — 0,65 1,65/3,07/5,29/4,82/2,75 3,9 - 0.65 1.65 / 3.07 / 5.29 / 4.82 / 2.75 3.9
- Ejemplo comparativo 5 Comparative Example 5
- — 0,57 1,41/2,45/4,37/5,58/4,66 No determinado - 0.57 1.41 / 2.45 / 4.37 / 5.58 / 4.66 Not determined
- Ejemplo comparativo 6 Comparative Example 6
- — 0,51 1,86/4,70/5,68/8,75/8,41 0,12 - 0.51 1.86 / 4.70 / 5.68 / 8.75 / 8.41 0.12
30 Tabla 1: Continuacion30 Table 1: Continuation
- Ejemplos Examples
- Escurrimiento a 45° [mml Prueba de diez orificios Migracion en seco Nota Migracion en humedo [%] Runoff at 45 ° [mml Ten-hole test Dry migration Note Wet migration [%]
- Teorico Theoretical
- Max. 30 10/10/10 1 Max. 15 Max. 30 10/10/10 1 Max. fifteen
- Ejemplo 1 Example 1
- 23 10/10/10 1 8 23 10/10/10 1 8
- Ejemplo 2 Example 2
- 29 10/10/10 1 6 29 10/10/10 1 6
- Ejemplo comparativo 1 Comparative Example 1
- 27 10/10/10 1 45 27 10/10/10 1 45
- Ejemplo comparativo 2 Comparative Example 2
- 53 9/10/10 1 13 53 10/9/10 1 13
- Ejemplo comparativo 3 Comparative Example 3
- 25 10/10/10 1 30 25 10/10/10 1 30
- Ejemplo comparativo 4 Comparative Example 4
- 24 10/10/9 4 100 24 10/10/9 4 100
- Ejemplo comparativo 5 Comparative Example 5
- 31 7/10/10 1 64 31 10/7/10 1 64
- Ejemplo comparativo 6 Comparative Example 6
- 152 8/98 1 15 152 8/98 1 15
Claims (16)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102012021742 | 2012-11-06 | ||
| DE102012021742.0A DE102012021742A1 (en) | 2012-11-06 | 2012-11-06 | Composition for the permanent hydrophilization of polyolefin fibers and their use |
| PCT/EP2013/072678 WO2014072210A1 (en) | 2012-11-06 | 2013-10-30 | Composition for permanently hydrophilizing polyolefin fibers and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2613880T3 true ES2613880T3 (en) | 2017-05-26 |
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| ES13786214.0T Active ES2613880T3 (en) | 2012-11-06 | 2013-10-30 | Composition for permanent hydrophilization of polyolefin fibers and their use |
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| EP (1) | EP2917398B1 (en) |
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| ES (1) | ES2613880T3 (en) |
| IL (1) | IL238665B (en) |
| MY (1) | MY185896A (en) |
| SA (1) | SA515360388B1 (en) |
| WO (1) | WO2014072210A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102014111881A1 (en) | 2014-08-20 | 2016-02-25 | Klaus Schmitt Beteiligungsgesellschaft Mbh | Aqueous waterproofing agent for fabrics of hydrophobic thermoplastic materials and products made therefrom |
| CN106715786B (en) * | 2014-12-17 | 2020-07-24 | 花王株式会社 | Liquid film cracking agent |
| DE102014119332A1 (en) * | 2014-12-22 | 2016-06-23 | Schill + Seilacher Gmbh | Composition for permanent hydrophilic finishing of textile fibers and textile products |
| CN105316944B (en) * | 2015-11-26 | 2017-10-10 | 常州市灵达化学品有限公司 | The multiple hydrophilizing agent of polyolefm non-woven cloth longtitudinal dispersion type |
| CN105332278B (en) * | 2015-11-26 | 2017-12-05 | 常州市灵达化学品有限公司 | The environmentally friendly multiple hydrophilic finishing agent of polyolefm non-woven cloth |
| CN105714555A (en) * | 2015-12-28 | 2016-06-29 | 福建恒安集团有限公司 | Polypropylene spunbonded nonwoven after going through surface hydrophilic treatment |
| CN105714561A (en) * | 2015-12-28 | 2016-06-29 | 福建恒安集团有限公司 | Finishing agent of emulsion composition for polypropylene spunbonded nonwoven |
| CN108611852A (en) * | 2018-05-08 | 2018-10-02 | 浙江理工大学 | A kind of ES fibers are without the multiple hydrophilic finish of silicon |
| CN108611697A (en) * | 2018-05-08 | 2018-10-02 | 浙江理工大学 | A kind of multiple hydrophilic finish of ES fibers |
| KR102106060B1 (en) | 2018-06-22 | 2020-04-29 | 한국에너지기술연구원 | Method of hydrophilic surface modification for hydrophobic polylefin and use thereof |
| CN108998889A (en) * | 2018-08-17 | 2018-12-14 | 绩溪袁稻农业产业科技有限公司 | A kind of preparation process of ES hydrophilic fibers non-woven fabrics |
| KR102420139B1 (en) | 2020-10-16 | 2022-07-12 | 도레이첨단소재 주식회사 | Highly absorbent composite fiber, highly absorbent non-woven fabric and article including the non-woven fabric |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5789669A (en) * | 1980-11-14 | 1982-06-04 | Teijin Ltd | Spinning oil agent for polyester fiber |
| JPS646176A (en) | 1987-06-25 | 1989-01-10 | Takemoto Oil & Fat Co Ltd | Treating agent for hydrophilizing cotton of polyolefinic fiber |
| US5258129A (en) | 1987-12-02 | 1993-11-02 | Takemoto Yushi Kabushiki Kaisha | Fluid-permeable agent for non-woven sheets of polyolefin fibers and method of application thereof |
| US5045387A (en) | 1989-07-28 | 1991-09-03 | Hercules Incorporated | Rewettable polyolefin fiber and corresponding nonwovens |
| EP0550361B1 (en) * | 1991-12-31 | 1996-10-16 | Stepan Europe | Surface active quaternary ammonium compounds, processes for their preparation and softening compositions derived from them |
| DE19645380B4 (en) | 1996-11-04 | 2008-04-17 | Schill + Seilacher Ag | Composition for the permanent hydrophilization of polyolefin fibers, and use of the composition |
| JP4411667B2 (en) * | 1998-07-10 | 2010-02-10 | チッソ株式会社 | Durable hydrophilic fiber and fiber molded body using the same |
| JP4089996B2 (en) * | 1999-06-22 | 2008-05-28 | 竹本油脂株式会社 | Processing agent and processing method for polyolefin fiber for manufacturing nonwoven fabric by dry method |
| JP3404555B2 (en) * | 1999-09-24 | 2003-05-12 | チッソ株式会社 | Hydrophilic fibers and nonwoven fabrics, processed nonwoven fabrics using them |
| DE112004000559B4 (en) * | 2003-04-01 | 2014-05-28 | Matsumoto Yushi-Seiyaku Co., Ltd. | Water-permeable agent and fiber to which the water-permeable agent has been applied |
| EP1600532B1 (en) | 2004-05-26 | 2007-06-13 | Dr. Th. Böhme KG Chem. Fabrik GmbH & Co. | Hydrophilising of polyolefin- and/or polyester-containing materials |
| JP5159534B2 (en) * | 2008-09-18 | 2013-03-06 | 松本油脂製薬株式会社 | Water permeability imparting agent, water permeable fiber to which it is attached, and method for producing nonwoven fabric |
| JP5277131B2 (en) * | 2009-09-29 | 2013-08-28 | 松本油脂製薬株式会社 | Water permeability imparting agent, water permeable fiber, and method for producing nonwoven fabric |
-
2012
- 2012-11-06 DE DE102012021742.0A patent/DE102012021742A1/en not_active Withdrawn
-
2013
- 2013-10-30 CN CN201380058160.5A patent/CN104903509B/en not_active Expired - Fee Related
- 2013-10-30 EP EP13786214.0A patent/EP2917398B1/en not_active Not-in-force
- 2013-10-30 ES ES13786214.0T patent/ES2613880T3/en active Active
- 2013-10-30 KR KR1020157013146A patent/KR102106115B1/en active IP Right Grant
- 2013-10-30 DK DK13786214.0T patent/DK2917398T3/en active
- 2013-10-30 JP JP2015540107A patent/JP6241829B2/en not_active Expired - Fee Related
- 2013-10-30 MY MYPI2015701324A patent/MY185896A/en unknown
- 2013-10-30 WO PCT/EP2013/072678 patent/WO2014072210A1/en active Application Filing
- 2013-10-30 US US14/439,280 patent/US20150292144A1/en not_active Abandoned
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2015
- 2015-05-05 SA SA515360388A patent/SA515360388B1/en unknown
- 2015-05-06 IL IL238665A patent/IL238665B/en active IP Right Grant
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| Publication number | Publication date |
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| IL238665A0 (en) | 2015-06-30 |
| SA515360388B1 (en) | 2016-02-25 |
| US20150292144A1 (en) | 2015-10-15 |
| KR20150082329A (en) | 2015-07-15 |
| EP2917398A1 (en) | 2015-09-16 |
| IL238665B (en) | 2019-02-28 |
| DK2917398T3 (en) | 2017-03-06 |
| WO2014072210A1 (en) | 2014-05-15 |
| MY185896A (en) | 2021-06-14 |
| EP2917398B1 (en) | 2016-12-07 |
| JP6241829B2 (en) | 2017-12-06 |
| CN104903509A (en) | 2015-09-09 |
| DE102012021742A1 (en) | 2014-05-08 |
| KR102106115B1 (en) | 2020-05-04 |
| JP2015533391A (en) | 2015-11-24 |
| CN104903509B (en) | 2018-07-03 |
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