ES2662017T3 - Poliésteres alifático-aromáticos biodegradables - Google Patents
Poliésteres alifático-aromáticos biodegradables Download PDFInfo
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- 229920000728 polyester Polymers 0.000 title description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 16
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract description 4
- 229920001634 Copolyester Polymers 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 2
- 150000002009 diols Chemical class 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 238000005227 gel permeation chromatography Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
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- 238000005303 weighing Methods 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
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- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
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- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
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Abstract
Película que comprende un copoliéster alifático/aromático (AAPE) biodegradable que comprende: a) un componente ácido que comprende unidades repetitivas de: 1. del 50 al 60 % molar de un ácido aromático polifuncional; 2. del 40 al 5 50 % molar de un ácido alifático, al menos el 90 % de este es un ácido dicarboxílico de cadena larga (LCDA) de origen natural seleccionado de ácido azelaico, ácido sebácico, ácido brasílico o mezclas de los mismos; b) al menos un componente de diol; teniendo dicho ácido dicarboxílico alifático de cadena larga (LCDA) y dicho componente de diol (b) un número de átomos de carbono según la fórmula siguiente: (CLCDA * YLCDA) /2 + Cb * Yb > 7,5 en donde: - CLCDA es el número de átomos de carbono del LCDA y puede ser 9, 10 o 13; - YLCDA es la fracción molar de cada LCDA sobre el número total de moles del LCDA; - Cb es el número de átomos de carbono de cada componente de diol; - Yb es la fracción molar de cada diol sobre el número total de moles del componente de diol (b) teniendo dicho AAPE: - una biodegradabilidad después de 90 días superior al 70 %, con respecto a la celulosa pura según la Norma ISO 14855 Modificación 1; - una densidad, medida con una máquina para el pesado Mohr-Westphal, igual o inferior a 1,20 g/cc; - un peso molecular promedio en número Mn, determinado mediante cromatografía de permeación en gel, de 40.000 a 140.000; - una viscosidad intrínseca, medida con viscosímetro Ubbelhode para disoluciones en CHCl3, de una concentración de 0,2 g/dl a 25ºC) de 0,8 a 1,5.
Description
isocianuratos, etc.
La viscosidad intrínseca de tales copolímeros de bloque puede estar comprendida entre 0,3 y 1,5 dl/g, más preferiblemente entre 0,45 y 1,2 dl/g. La cantidad de sustancia compatibilizadora en la mezcla de copoliésteres alifático-aromáticos y ácido poliláctico puede estar comprendida en el intervalo entre el 0,5 y el 50 %, más preferiblemente entre el 1 y el 30 %, más preferiblemente entre el 2 y el 20 % en peso.
Los poliésteres según la presente invención pueden mezclarse ventajosamente también con cargas tanto de naturaleza orgánica como inorgánica. La cantidad preferida de cargas está comprendida en el intervalo entre el 0,5 y el 70 % en peso, preferiblemente entre el 5 y el 50 % en peso.
En cuanto a las cargas orgánicas, pueden mencionarse polvo de madera, proteínas, polvo de celulosa, residuos de uvas, salvado, cáscaras de maíz, compost, otras fibras naturales, polvos de cereales con y sin plastificantes, tales como polioles.
En cuanto a las cargas inorgánicas, pueden mencionarse las sustancias que son capaces de ser dispersadas y/o de ser reducidas a laminillas con dimensiones submicrónicas, preferiblemente inferiores a 500 nm, más preferiblemente inferiores a 300 nm y aún más preferiblemente inferiores a 50 nm.
Son particularmente preferidos las zeolitas y los silicatos de varios tipos, tales como wollastonitas, montmorillonitas, hidrotalcitas funcionalizadas también con moléculas capaces de interactuar con el almidón y/o el poliéster específico. El uso de tales cargas puede mejorar la rigidez, la permeabilidad al agua y al gas, la estabilidad dimensional y mantener la transparencia.
El proceso de producción de los poliésteres según la presente invención puede realizarse según cualquiera de los procesos conocidos en el estado de la técnica. En particular, los poliésteres pueden obtenerse ventajosamente con una reacción de policondensación.
El proceso de polimerización del copoliéster puede ponerse en práctica ventajosamente en presencia de un catalizador adecuado. Como catalizadores adecuados, pueden mencionarse, a modo de ejemplo, compuestos metalo-orgánicos de estaño, por ejemplo, los derivados del ácido estannoico, compuestos de titanio, por ejemplo, titanato de ortobutilo y compuestos de aluminio, por ejemplo, aluminio de triisopropilo, compuestos de antimonio y compuestos de zinc.
Ejemplos
En los ejemplos proporcionados a continuación en el presente documento, se adoptaron los siguientes métodos de ensayo:
-MFR se midió en las condiciones previstas en la norma ASTM D 1238-89 a 150 ºC y 5 kg o a 190 ºC y 2,16 kg; -las temperaturas de fusión y cristalización y las entalpías se midieron con un calorímetro de barrido diferencial DSC7 de Perkin Elmer, funcionando con el siguiente perfil de temperatura:
1ª exploración desde -30 ºC hasta 200 ºC a 20 ºC/min
2ª exploración desde 200 ºC hasta -30 ºC a 10 ºC/min
3ª exploración desde -30 ºC hasta 200 ºC a 20 ºC/min -Tm1 se midió como valor endotérmico del pico de la 1ª exploración, y Tm2 como el de la 3ª exploración; Tc se midió como valor exotérmico del pico de la 2ª exploración.
-Densidad. La determinación de la densidad según el método Mohr Westphal se realizó con una balanza analítica AC 120S de Sartorius equipada con un kit YDK 01 de Sartorius. El kit estaba provisto de dos cestillas. Una vez montado el kit, se introdujo etanol en el cristalizador. La balanza se mantuvo a temperatura ambiente.
Cada ensayo se realizó con aproximadamente 2 g de polímero (una o más pellas). La densidad d se determinó según la fórmula siguiente: D = (Wa/G) \ dfl en donde: Wa: peso de la muestra en aire Wfl: peso de la muestra en alcohol
8
G = Wa-Wfl
dfl = densidad del etanol a temperatura ambiente (valores leídos en las tablas proporcionadas por la empresa Sartorius con el kit). El error experimental de los valores de la densidad está comprendido en el intervalo de ± 2, 5 x 10-3 .
5 -ηin se ha determinado según el método de la ASTM 2857-87 -Mn se ha determinado en un sistema GPC de la serie Agilent 1100, con cloroformo como eluyente y niveles de poliestireno para la curva de calibración.
Ejemplo 1
Un reactor de acero de 25 l, provisto de un agitador mecánico, una entrada para el flujo de nitrógeno, un 10 condensador y una conexión a una bomba de vacío se cargó con:
-2.890 g de ácido tereftálico (17,4 mol),
-3.000 g de ácido sebácico (14,8 mol),
-3.500 g butanodiol (38,9 mol),
-6,1 g de ácido butilestannoico.
15 El porcentaje molar de ácido tereftálico con respecto a la suma de los moles de los componentes ácidos fue del 54,0 % molar.
La temperatura del reactor se aumentó, a continuación, hasta 200 ºC, y se aplicó un flujo de nitrógeno. Después de destilarse aproximadamente el 90 % de la cantidad teórica de agua, la presión se redujo gradualmente hasta que se alcanzó un valor inferior a 3 mm Hg, y la temperatura se aumentó hasta 240 ºC.
20 Después de aproximadamente 3 horas, el producto fusionado se vertió en el reactor, se enfrió en un baño de agua y se granuló. Durante las últimas operaciones fue posible observar cómo el producto comienza a solidificarse rápidamente y puede ser granulado fácilmente. El producto obtenido tenía una viscosidad intrínseca (medida en cloroformo a 25 ºC, c = 0,2 g/dl), ηin = 0,93 (dl/g), MFR (190 ºC; 2,16 kg) = 20 g/10 min, Mn = 52.103 y una densidad de 1,18 g/cm3.
25 A partir del análisis por H-RMN, se halló un porcentaje de unidades aromáticas del 53,5 ± 0,5 %.
Ejemplo 1A
El reactor, según el Ejemplo 1, se cargó con los mismos ingredientes del Ejemplo 1: -2.890 g de ácido tereftálico (17,4 mol), -3.000 g de ácido sebácico (14,8 mol),
30 -3.500 g butanodiol (38,9 mol), -6,1 g de ácido butilestannoico.
El porcentaje molar de ácido tereftálico con respecto a la suma de los moles de los componentes ácidos fue del 54,0 % molar. La reacción se ha realizado en el tiempo necesario para obtener un producto que tiene una viscosidad intrínseca
35 (medida en cloroformo a 25 ºC, c = 0,2 g/dl), ηin = 1,03 (dl/g), MFR (190 ºC; 2,16 kg) = 14,8 g/10 min, Mn = 58.097 y una densidad de 1,18 g/cm3.
Ejemplo 2 (comparativo)
El reactor, según el Ejemplo 1, se cargó con: -2.480 g de ácido tereftálico (14,9 mol),
40 -3.400 g de ácido sebácico (16,8 mol), -3.430 g butanodiol (38,1 mol), -6,1 g de ácido butilestannoico.
9 5
10
15
20
25
30
35
40
El porcentaje molar de ácido tereftálico con respecto a la suma de los moles de los componentes ácidos fue del 47 % molar.
La temperatura del reactor se aumentó, a continuación, hasta 200 ºC, y se aplicó un flujo de nitrógeno. Después de destilarse aproximadamente el 90 % de la cantidad teórica de agua, la presión se redujo gradualmente hasta que se alcanzó un valor inferior a 3 mm Hg, y la temperatura se aumentó hasta 240 ºC.
Después de aproximadamente 3 horas, se obtuvo un producto con viscosidad intrínseca (medida en cloroformo a 25 ºC, c = 0,2 g/dl), ηin = 1,00 (dl/g), MFR (190 ºC; 2,16 kg) = 13 g/10 min.
A partir del análisis por H-RMN, se halló un porcentaje de unidades aromáticas del 47,0 ± 0,5 %.
Ejemplo 3 (comparativo)
El reactor, según el Ejemplo 1, se cargó con: -2.770 g de tereftalato de dimetilo (14,3 mol), -3.030 g de adipato de dimetilo (17,4 mol), -3.710 g butanodiol (41,2 mol), -0,7 g de ortotitanato de tetraisopropilo (disuelto en n-butanol)
El porcentaje molar de contenido aromático con respecto a la suma de los moles de los componentes ácidos fue del 45 % molar.
La temperatura del reactor se aumentó, a continuación, hasta 200-210 ºC. Después de destilarse al menos el 95 % de la cantidad teórica de metanol, la presión se redujo gradualmente hasta que se alcanzó un valor inferior a 2 mm Hg, y la temperatura se aumentó a 250-260 ºC.
Después de aproximadamente 4 horas, se obtuvo un producto con viscosidad intrínseca (medida en cloroformo a 25 ºC, c = 0,2 g/dl), ηin = 0,92 (dl/g), MFR (190 ºC; 2,16 kg) = 20 g/10 min. A partir del análisis por H-RMN, se halló un porcentaje de unidades aromáticas del 47,0 ± 0,5 %.
Ejemplo 4 (comparativo)
El proceso del Ejemplo 1 se repitió con: -3.623,9 g de tereftalato de dimetilo (18,68 mol), -3.582,5 g butanodiol (39,81 mol), -2.244,7 g de ácido azelaico (11,94 mol).
El porcentaje molar de contenido aromático con respecto a la suma de los moles de los componentes ácidos fue del
61 % molar. Se obtuvo un producto con viscosidad intrínseca (medida en cloroformo a 25 ºC, c = 0,2 g/dl), ηin = 0,95 (dl/g), densidad 1,21 g/cc y MFR (190 ºC; 2,16 kg) = 5,5 g/10 min.
Ejemplo 5
El proceso del Ejemplo 1 se repitió con: -3.476,48 g de tereftalato de dimetilo (17,92 mol), -3.493,80 g butanodiol (38,82 mol), -2.411 g de ácido sebácico (11,94 mol).
El porcentaje molar de contenido aromático con respecto a la suma de los moles de los componentes ácidos fue del
60 % molar. Se obtuvo un producto con Mn = 56.613, Mw/Mn = 2,0364 viscosidad intrínseca (medida en cloroformo a 25 ºC, c = 0,2 g/dl), ηin = 0,97 (dl/g), densidad 120 g/cc y MFR (190 ºC; 2,16 kg) = 7,8 g/10 min.
10
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