ES2661713T3 - Composiciones de polietileno y cierres para botellas - Google Patents

Composiciones de polietileno y cierres para botellas Download PDF

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ES2661713T3
ES2661713T3 ES12833326.7T ES12833326T ES2661713T3 ES 2661713 T3 ES2661713 T3 ES 2661713T3 ES 12833326 T ES12833326 T ES 12833326T ES 2661713 T3 ES2661713 T3 ES 2661713T3
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ethylene copolymer
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melt index
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Xiaochuan Wang
Yves Lacombe
Mark Edmund Weber
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Nova Chemicals International SA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing more than three carbon atoms
    • C08L23/0815—Copolymers of ethene with aliphatic 1-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/02—Ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/001—Multistage polymerisation processes characterised by a change in reactor conditions without deactivating the intermediate polymer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/62—Refractory metals or compounds thereof
    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
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    • C08F4/64—Titanium, zirconium, hafnium or compounds thereof
    • C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
    • C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/06—Properties of polyethylene
    • C08L2207/062—HDPE

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  • Polymers & Plastics (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Casting Or Compression Moulding Of Plastics Or The Like (AREA)
  • Closures For Containers (AREA)

Abstract

Un cierre para botellas, comprendiendo dicho cierre una composición de polietileno bimodal que comprende: (1) del 10 al 70 % en peso de un primer copolímero de etileno que tiene un índice de fusión I2, inferior a 0,4 g/10 min; una distribución del peso molecular Mw/Mn, inferior a 3,0; y una densidad de 0,920 a 0,955 g/cm3; y (2) del 90 al 30 % en peso de un segundo copolímero de etileno que tiene un índice de fusión I2, de 100 a 10,000 g/10 min; una distribución del peso molecular Mw/Mn, inferior a 3,0; y una densidad superior a la densidad de dicho primer copolímero de etileno, pero inferior a 0,967 g/cm3; en donde el peso molecular promedio en peso Mw del primer copolímero de etileno es superior al peso molecular promedio en peso Mw del segundo copolímero de etileno; la densidad de dicho segundo copolímero de etileno es menos de 0,037 g/cm3 mayor que la densidad de dicho primer copolímero de etileno; la relación (SCB1/SCB2) del número de ramificaciones de cadena corta por mil átomos de carbono en dicho primer copolímero de etileno (SCB1) y el número de ramificaciones de cadena corta por mil átomos de carbono en dicho segundo copolímero de etileno (SCB2) es superior a 0,5; y en donde la composición de polietileno bimodal tiene una distribución del peso molecular Mw/Mn, de 3 a 11; una densidad de al menos 0,949 g/cm3; un índice de fusión I2, de 0,4 a 5,0 g/10 min; un Mz inferior a 400.000; una condición B de ESCR (10 % de IGEPAL) de al menos 20 horas, calculado de acuerdo con la norma ASTM D1693; y satisface la siguiente relación: Log10[l6/l2]/Log10[6,48/2,16] < 1,50 en la que I2 es el índice de fusión medido de acuerdo con la norma ASTM D1238 a 190 ºC usando un peso de 2,16 kg, e I6 es el índice de fusión medido de acuerdo con la norma ASTM D1238 a 190 ºC usando un peso de 6,48 kg.

Description

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estequiométricas con respecto al complejo de titanio. El metilaluminoxano (MAO) disponible comercialmente se incluyó como secuestrante en una Al:Ti de aproximadamente 40:1. Además, se añadió 2,6-di-terc-butilhidroxi-4etilbenceno para eliminar el trimetilaluminio libre dentro de la MAO en una relación de AI:OH de aproximadamente 0,5:1.
5 Las condiciones de polimerización usadas para preparar las composiciones de la invención se proporcionan en la Tabla 1.
Las propiedades de la composición de polietileno de la invención y comparativa se describen en las tablas 2.
10 Las propiedades calculadas para el primer copolímero de etileno y el segundo copolímero de etileno para composiciones de polietileno determinadas comparativas y de la invención, obtenidas a partir de estudios de desconvolución de GPC-FTIR, se proporcionan en la Tabla 3.
15 Las propiedades de las placas prensadas hechas a partir de composiciones de polietileno comparativas y de la invención se proporcionan en la Tabla 4.
Las composiciones de polietileno comparativas (ejemplos comparativos 1-5) se preparan usando un catalizador de fosfinimina de sitio único en un proceso de disolución de doble reactor y tienen un ESCR en la condición B10 de 20 menos de 24 horas y una relación SCB1/SCB2 de 0,50 o menos.
La composición de polietileno comparativa (ejemplo comparativo 6) es una resina disponible comercialmente de Dow Chemical, DMDA-1250 NT 7 y tiene una ESCR en la condición B-10 de más de 150 horas y un Mz de más de
400.000.
25 Las composiciones de polietileno de la invención (ejemplos de la invención 1-9) se preparan utilizando un catalizador de fosfinimina de sitio único en un proceso de solución de reactor doble como se ha descrito anteriormente y tienen un ESCR en la condición B10 de más de 20 horas y una relación SCB1/SCB2 mayor que 0,50. Estos ejemplos de la invención también tienen valores de Mz de menos de 400.000.
30
TABLA 1
Condiciones del reactor de los ejemplos de la invención
N.º de ejemplo
Ejemplo comparativo 1 Ejemplo comparativo 2 Ejemplo comparativo 3 Ejemplo comparativo 4 Ejemplo comparativo 5
Reactor 1
Etileno (kg/h)
35,6 38,1 35,7 36,7 37,5
Octeno (kg/h)
4,9 4 5,3 4,1 4,8
Hidrógeno (g/h)
0,51 0,58 0,51 0,50 0,50
Disolvente (kg/h)
319,2 329 296,5 296,8 286,8
Temperatura de entrada de alimentación en el reactor (°C)
30 30 30 30 30
Temperatura del reactor (°C)
138,2 140,5 141,1 143,8 149,2
Catalizador de titanio (ppm)
0,14 0,10 0,12 0,1 0,1
Reactor 2
Etileno (kg/h)
43,6 51,6 43,6 44,9 45,9
Octeno (kg/h)
0 0 0 0 0
Hidrógeno (g/h)
22,2 13,46 22,2 16,4 21
Disolvente (kg/h)
106,7 137,2 129,1 127,5 135
Temperatura de
30 30 30 31,3 29,8
17
entrada de alimentación en el reactor (°C)
Temperatura del reactor (°C)
186,9 192,1 186,3 190,9 194
Catalizador de titanio (ppm)
0,29 0,23 0,21 0,21 0,24
TABLA 1 CONTINUACIÓN Condiciones del reactor de los ejemplos de la invención
N.º de ejemplo
Ejemplo comparativo 6 Ejemplo comparativo 7 Ejemplo comparativo 8 Ejemplo comparativo 9
Reactor 1
Etileno (kg/h)
35,7 35,6 35,7 38,4
Octeno (kg/h)
2,6 4,7 4,9 1,5
Hidrógeno (g/h)
0,45 0,46 0,46 0,62
Disolvente (kg/h)
256,6 259,1 258,9 346,3
Temperatura de entrada de alimentación en el reactor (°C)
30 30 30 30
Temperatura del reactor (°C)
152,5 151 147 141,1
Catalizador de titanio (ppm)
0,08 0,13 0,10 0,10
Reactor 2
Etileno (kg/h)
43,6 43,6 43,6 51,9
Octeno (kg/h)
O 0 0 0
Hidrógeno (g/h)
10,2 21,59 16,21 15,07
Disolvente (kg/h)
171,6 167 167,1 121,7
Temperatura de entrada de alimentación en el reactor (°C)
30 30 30 30
Temperatura del reactor (°C)
185,7 186,2 186,4 192,8
Catalizador de titanio (ppm)
0,13 0,22 0,20 0,31
TABLA 2 Propiedades de la resina
N.º de ejemplo
Ejemplo comparativo 1 Ejemplo comparativo 2 Ejemplo comparativo 3 Ejemplo comparativo 4 Ejemplo comparativo 5
Densidad (g/cm3)
0,9534 0,9523 0,9526 0,952 0,953
Propiedades de reología/flujo
Índice de fusión I2 (g/10 min)
1,88 0,625 1,42 1,92 0,68
Índice de fluidez (l2ι/l2)
56,9 51,2 50,5 77,1 73,2
Exponente de tensión
1,41 1,38 1,36 1,38 1,38
I21 (g/10 min)
107 33,1 71,3 146,0 49,8
I5 (g/10 min)
4,23
18
I21/I5
16,86
Viscosidad de cizalladura a 105 s -1 (240 °C, Pa-s)
5,8
relación de la viscosidad de cizalladura η(10s-1)/η(1000s 1) a 240 °C
12,0
Datos de DMA (190 °C)
η* = 5832 Pa*s a G* = 2,099 kPa; η* = 5591 Pa*s a G* = 2,795 kPa
GPC
Mn
14393 22392 17827 9891 12424
Mw
91663 109626 105289 77319 104353
Mz
325841 299470 282159 245479 327007
Índice de polidispersidad (Mw/Mn)
6,37 4,9 5,91 7,82 8,4
Mz/Mw
3,55 3,56 2,68 3,17 3,13
Frecuencia de ramificación -FTIR (sin corregir para el extremo de cadena -CH3)
SCB sin corregir/1.000 C
2,2 2 2,2 3,7 2,5
Contenido de comonómeros sin corregir (% mol)
0,4 0,4 0,4 0,7 0,5
ID del comonómero
Octeno octeno octeno octeno octeno
% mol del comonómero medido mediante RMN de 13C
Ramificaciones de hexilo+(≥ 4 átomos de carbono), % mol
0,3 0,2 0,28
CTREF lenta
CDBI50 (%)
63
DSC
Pico de fusión primario (ºC)
128,3 129,7 129,11 126,8 128,42
Calor de fusión (J/g)
204,7 198,2 207,7 200,3 213,80
Cristalinidad (%)
70,58 68,34 71,61 69,08 73,72
Otras propiedades
Extraíbles en hexano (% en p)
0,44 0,46 0,32 0,73 0,57
VICAT oft. Pt. (°C) -Placa
126 127 127,3 122 125
Temperatura de deflexión térmica [C] a 66 PSI
72 71 68,2 68 71
19
TABLA 2 CONTINUACIÓN Propiedades de la resina
N.º de ejemplo
Ejemplo comparativo 6 Ejemplo comparativo 1 Ejemplo comparativo 2 Ejemplo comparativo 3 Ejemplo comparativo 4
Densidad (g/cm3)
0,955 0,9529 0,9524 0,9524 0,9523
Propiedades de reología/flujo
Índice de fusión I2 (g/10 min)
1,5 1,57 2,94 1,69 1,5
Índice de fluidez (l2ι/l2)
66 58 44,1 61 54,8
Exponente de tensión
1,58 1,38 1,36 1,38 1,4
l2ι (g/10 min)
99 90 129 104 82,3
I5 (g/10 min)
5,31 4,72 4,94 4,5
I21/I5
18,64 19,07 21,05 18,29
Viscosidad de cizalladura a 105 s -1 (240 °C, Pa-s)
6,2 5,1 6,2 4,8 5,8
relación de la viscosidad de cizalladura η(10s-1)/η(1000s-1) a 240 °C
11,3 13,5 8,1 13,0 14,8
Datos de DMA (190 °C)
η* = 5294 Pa*s a G* = 2,647 kPa; η* = 5106 Pa*s a G* = 3,547 kPa η* = 4889 Pa*s a G* = 2,445 kPa; η* = 4739 Pa*s a G* = 3,292 kPa
GPC
Mn
10240 10524 15679 10579 13309
Mw
106992 83712 74090 86319 88295
Mz
533971 256210 215369 291056 278141
Índice de polidispersidad (Mw/Mn)
10,45 7,95 4,73 8,16 6,63
Mz/Mw
4,99 3,06 2,91 3,37 3,15
Frecuencia de ramificación -FTIR (sin corregir para el extremo de cadena -CH3)
SCB sin corregir/1.000 C
2,3 3 1,8 3 2,1
Contenido de comonómeros sin corregir (% mol)
0,5 0,6 0,4 0,6 0,4
ID del comonómero
hexeno octeno octeno octeno octeno
% mol del comonómero medido mediante RMN de 13C
Ramificaciones de hexilo+(≥ 4 átomos de carbono), % mol
0,4 0,4 0,3
CTREF lenta
CDBI50(%)
63,4 81,8 86,2 80,4 76,5
DSC
Pico de fusión primario (ºC)
130,06 127,3 128,8 127,5 129
20
Calor de fusión (J/g)
217,4 203,8 206,1 207,3 209
Cristalinidad (%)
74,98 70,27 71,08 71,48 72,08
Otras propiedades
Extraíbles en hexano (% en p)
0,36 0,36 0,22 0,42 0,25
VICAT oft. Pt. (°C) -Placa
126,8 125,2 126,8 124,8 126,4
Temperatura de deflexión térmica [C] a 66 PSI
73 68 74,1 76 67,3
TABLA 2 CONTINUACIÓN Propiedades de la resina
N.º de ejemplo
Ejemplo comparativo 5 Ejemplo comparativo 6 Ejemplo comparativo 7 Ejemplo comparativo 8 Ejemplo comparativo 9
Densidad (g/cm3)
0,9532 0,9527 0,9534 0,9522 0,9568
Propiedades de reología/flujo
Índice de fusión I2 (g/10 min)
1,78 1,29 2,05 1,31 1,68
Índice de fluidez (l21/l2)
55,6 44,1 55 64 54,2
Exponente de tensión
1,37 1,35 1,34 1,39 1,40
I21 (g/10 min)
99,1 57 113 83 91
I5 (g/10 min)
5,33 6,21
I21/I5
18,59 18,20
Viscosidad de cizalladura a 105 s -1 (240 °C, Pa-s)
5,1 6,3 5,0 5,8 6,0
relación de la viscosidad de cizalladura η(10s-1)/η(1000s-1) a 240 °C
13,3 11,6 12,1 14,8 11,2
Datos de DMA (190 °C)
η* = 6707 Pa*s a G* = 2,413 kPa; η* = 6465 Pa*s a G* = 3,232 kPa η* = 6688 Pa*s a G* = 2,407 kPa; η* = 6472 Pa*s a G* = 3,236 kPa
GPC
Mn
9716 18449 11145 14021 15110
Mw
84943 93080 80630 93175 85227
Mz
288665 272788 243944 303823 287035
Índice de polidispersidad (Mw/M„)
8,74 5,05 7,23 6,65 5,64
Mz/Mw
3,40 2,93 3,03 3,26 3,37
Frecuencia de ramificación -FTIR (sin corregir para el extremo de cadena -CH3)
SCB sin corregir/1.000 C
2,5 1,7 2,8 2,2 1,3
Contenido de comonómeros sin corregir (% mol)
0,5 0,3 0,6 0,4 0,3
ID del comonómero
Octeno octeno octeno octeno octeno
21
% mol del comonómero medido mediante RMN de 13C
Ramificaciones de hexilo+(>= 4 átomos de carbono), % mol
CTREF lenta
CDBI50(%)
75,2 86,2 79,7 80,4 77,8
DSC
Pico de fusión primario (ºC)
128,3 129,8 127,9 128,4 130,7
Calor de fusión (J/g)
207,3 208,5 211,1 205,4 213,8
Cristalinidad (%)
71,48 71,9 72,8 70,82 73,73
Otras propiedades
Extraíbles en hexano (% en p)
0,33 0,25 0,38 0,27 0,24
VICAT oft. Pt. (°C) -Placa
125,4 128,2 125,2 126,2 128,4
Temperatura de deflexión térmica [C] a 66 PSI
69,8 68,2 66,8 69 77,6
22
imagen16
imagen17
imagen18
imagen19
imagen20

Claims (1)

  1. imagen1
    imagen2
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CN103917592B (zh) 2016-04-06
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CA2752407A1 (en) 2013-03-19
US20130072632A1 (en) 2013-03-21
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BR112014006344A2 (pt) 2017-04-04
DK2751193T3 (en) 2018-03-05
JP6054970B2 (ja) 2016-12-27
EP2751193A1 (en) 2014-07-09
WO2013040676A1 (en) 2013-03-28
CA2752407C (en) 2018-12-04
CL2014000670A1 (es) 2015-01-09
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