ES2543739T3 - Poliesterpolioles de ácido tereftálico y oligo óxidos de alquileno - Google Patents

Poliesterpolioles de ácido tereftálico y oligo óxidos de alquileno Download PDF

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ES2543739T3
ES2543739T3 ES10711844.0T ES10711844T ES2543739T3 ES 2543739 T3 ES2543739 T3 ES 2543739T3 ES 10711844 T ES10711844 T ES 10711844T ES 2543739 T3 ES2543739 T3 ES 2543739T3
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acid
terephthalic acid
mol
alkylene oxides
polyol
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Hartmut Nefzger
Erika Bauer
Uwe Künzel
Jürgen SCHLOSSMACHER
Lutz Brassat
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Bayer Intellectual Property GmbH
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    • 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
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    • C08G18/40—High-molecular-weight compounds
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    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/141—Hydrocarbons
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    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/06—Polyurethanes from polyesters
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
    • Y10T428/1376—Foam or porous material containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Poliesterpoliol con una concentración de grupos éter en el intervalo entre 9,0 mol/kg de poliesterpoliol y 16 mol/kg de poliesterpoliol, que se produce a partir de una mezcla que comprende (A) ácido tereftálico, (A) (B) oligoetilenglicol de fórmula H-(OCH2CH2)n-OH con una cantidad numérica media de grupos oxietileno n en el intervalo entre 3,0 y 9,0, y (C) al menos un ácido dicarboxílico alifático seleccionado del grupo constituido por ácido succínico, ácido glutárico, ácido adípico, ácido sebácico, ácido subérico, ácido azelaico, ácido decanodicarboxílico, ácido dodecanodicarboxílico y ácido omega-hidroxicaproico.

Description

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E10711844
27-07-2015
Aparatos usados: Viscosímetro: MCR 51 de la empresa Anton Paar Métodos de análisis usados: Índice de hidroxilo: según Houben Weyl, Methoden der Organischen Chemie, volumen XIV/2
5 Makromolekulare Stoffe, página 17, Georg Thieme Verlag; Stuttgart 1963.
Índice de acidez: según Houben Weyl, Methoden der Organischen Chemie, volumen XIV/2 Makromolekulare Stoffe, página 17 y siguientes, Georg Thieme Verlag; Stuttgart 1963
A) Preparación de los poliesterpolioles
10 Ejemplo 1 (según la invención):
En un matraz de 4 bocas de 4 litros, equipado con manto calefactor, agitador mecánico, termómetro interno, columna de relleno de 40 cm, cabeza de columna, condensador intensivo descendente, así como bomba de vacío de membrana se colocaron previamente 2280 g (11,4 mol) de PEG 200 bajo atmósfera de nitrógeno a 100 ºC. En el transcurso de aproximadamente 5 minutos se mezclaron 732 g (4,41 mol) de ácido tereftálico y se le añadieron 83
15 mg de dicloruro de estaño dihidratado. Se calentó durante 2 horas hasta 230 ºC, separándose mediante destilación el agua y desapareciendo la turbidez de la mezcla de reacción. Entonces se añadieron 314 g (2,34 mol) de ácido glutárico técnico y se calentó durante otros 90 minutos hasta 230 ºC. Después se añadieron otros 83 mg de dicloruro de estaño dihidratado y se aplicó vacío, por último 30 mbar. En estas condiciones se dejó condensar otras 5,5 horas. Se enfrió y se determinaron las siguientes propiedades:
20 Análisis del poliéster:
Índice de hidroxilo: 160 mg de KOH/gÍndice de acidez: 2,0 mg de KOH/g Viscosidad: 1620 mPas (25 ºC), 310 mPas (50 ºC), 110 mPas (75 ºC)
Tabla 1: Composición y propiedades de poliesterpolioles según la invención y no según la invención
Ejemplo:
1 2 3(C) 4(C) 5(C) 6(C) 7(C) 8 9(C)
Ácido tereftálico
[g] 732 999 1052 1204 1112 1052 887 2465
PEG 200
[g] 2280 2176 1341 1499 1302 967 5263 2191
PEG 180
[g] 2041
Ácido glutárico técnico
[g] 314 160 325 333 505 919 104
Etilenglicol
[g] 471 387 505 644 552
PSA
[g] 791 834
Dicloruro de estaño dihidratado
[mg] 160 160 160 64
Tetrabutilato de titanio
[mg] 235 235 235 235 610
Índice de hidroxilo
[mg de KOH/g] 160 159 159,7 160 160 160 155,5 162,7 159,9
Índice de acidez
[mg de KOH/g] 2,0 1,9 0,2 0,2 0,2 0,3 0,4 1,5 0,5
Viscosidad, 25 ºC
[mPas] 1620 3510 2750 sólido sólido sólido sólido 3030 1960
Porcentaje de ácido tereftálico con respecto a todos los componentes
[% en peso] 22,0 31,2 32,6 35,9 33,4 31,3 27,0 28,2 0
Porcentaje de grupos éter de oligoetilenglicol
[mol/kg de éster] 11,6 10,4 11,4 7,0 7,8 6,8 5,1 9,8 11,5
Porcentaje de etilenglicol
[% en peso] 0 0 0 14,1 11,6 15,0 19,6 6,3 0
Porcentaje de PSA
[% en peso] 0 0 0 0 0 0 24,0 0 26,6
C = Ejemplo de comparación
25
El ejemplo 3(C) no es según la invención porque para la producción no se usa ningún componente (C) (en este caso en los ejemplos: ácido glutárico técnico). El ejemplo 4(C) no es según la invención, porque el porcentaje de los grupos éter de oligoetilenglicoles se encuentran por debajo de 9 mol/kg de éster y porque el porcentaje de componentes que no son (A), (B) ni (C), se encuentra por encima del 10 % en peso, en el caso concreto se utiliza el 30 14,1 % en peso de etilenglicol. Lo mismo sirve para los ejemplos 5(C), 6(C) y 7(C). Además, la tabla 1 muestra que
7
E10711844
27-07-2015
los poliesterpolioles 4(C), 5(C), 6(C) y 7(C) no según la invención a temperatura ambiente se encuentran de manera desventajosa en estado sólido, mientras que los poliesterpolioles 1, 2, 3 y 8 según la invención son líquidos de manera ventajosa. Si bien 9(C) satisface este criterio, no contiene sin embargo ácido tereftálico, lo que resulta por lo demás desventajoso en el comportamiento frente al fuego.
5 Materias primas para espumas rígidas de PUR/PIR:
a.) Poliéster de los ejemplos 1, 2, 3, 8, 9(C)
Aditivos para espumas, compuestos por b.) -d.):
b.) Agente reticulante de la empresa Evonik c.) Tegostab, estabilizador de la empresa Evonik
10 d.) DMCHA, N,N-dimetilciclohexilamina de la empresa Rheinchemie e.) TCPP, fosfato de tris(1-cloro-2-propilo) de la empresa Lanxess f.) n-Pentano, empresa Kraemer & Martin g.) Agua, desmineralizada h.) Activador: Desmorapid VP.PU 1792, empresa Bayer MaterialScience
15 i.) Desmodur VP.PU 44V40L, poliisocianato de la empresa Bayer MaterialScience
Tabla 2: Composición y propiedades de espumas de PUR/PIR a base de poliesterpoliol según la invención y no según la invención
Ejemplo
10 11 12 13 14(C) 15 16(C)
Poliol del ej. 2
[g] 90,0 90,0
Poliol del ej. 1
[g] 90,0 90,0
Poliol del ej. 3(C)
[g] 90,0
Poliol del ej. 8
[g] 91,0
Poliol del ej. 9(C)
[g] 96,0
Aditivos para espumas
[g] 2,4 2,4 12,3 12,3 12,3 2,4 12,3
TCPP
[g] 15,0 15,0 15,0 15,0 15,0 15,0 15,0
Agua
[g] 1,1 1,1 1,1 1,1 1,1 1,2 1,1
Desmorapid 1792
[g] 2,6 2,6 2,5 2,5 2,5 2,6 2,5
n-Pentano
[g] 17,0 17,0 17,0 17,0 17,0 17,0 18,0
Desmodur 44V40 L
[g] 200 200 200 200 200 200 200
Índice
354 352 239 239 239 340 232
Propiedades:
Densidad aparente del núcleo hallada
[kg/m3] 34,1 33,7 34,0 34,1 34,7 33,3 33,3
Tiempo de curado
[s] 43 40 28 27 24 44 27
Tiempo libre de pegajosidad
[s] 90 68 55 40 35 90 40
Adherencia tras 24 horas
[nota] 1 2 1-2 1 1 2 1
Clasificación KBT
B2 B2 B2 B2 B2 B2 B2
Ø Altura de la llama
[mm] 115 105 120 123 120 115 154
Estabilidad dimensional: Almacenamiento 24 h a -22 ºC
[%, dirección x] -0,1 0,1 0,1 -0,3 0,0 -0,1 -0,1
[%, dirección y]
-0,1 0,0 -0,2 -0,1 -0,2 -0,1 0,0
[%, dirección z]
0,0 0,0 0,0 0,1 0,1 0,0 0,0
Estabilidad dimensional: Almacenamiento 24 h a 80 ºC
[%, dirección x] -0,1 -0,1 0,1 -0,3 0,3 -0,7 -0,6
[%, dirección y]
0,0 0,4 0,4 0,3 -0,1 -0,3 -0,4
[%, dirección z]
-0,5 -0,5 0,0 -0,4 -0,1 -0,6 -0,3
Índice designa la razón molar de todos los grupos isocianato con respecto a todos los átomos de hidrógeno activos 20 Zerewitinoff.
Se pesan en un vaso de cartón todas las materias primas de la formulación de espuma rígida a escala de laboratorio a excepción del componente de poliisocianato, se templan a 23 ºC, se mezclan por medio de un mezclador de laboratorio Pendraulik (por ejemplo de tipo LM-34 de la empresa Pendraulik) y se añade dado el caso agente expansivo volatilizado (pentano). A continuación se añadió con agitación el componente de poliisocianato
25 (igualmente templado hasta 23 ºC) a la mezcla de poliol, se mezcló éste intensamente y se coló la mezcla de reacción en moldes de madera revestidos con papel. Durante el proceso de formación de espuma se determinaron el tiempo de curado y el tiempo libre de pegajosidad. Tras 24 horas, se cortaron a partir de la pieza en bruto de espuma probetas de ensayo en forma de dado de 9 cm de longitud de arista.
Se determinaron las siguientes propiedades:
30 Estabilidad dimensional: se determina, determinándose el cambio dimensional de probetas de ensayo en
8
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Claims (1)

  1. imagen1
ES10711844.0T 2009-04-09 2010-03-27 Poliesterpolioles de ácido tereftálico y oligo óxidos de alquileno Active ES2543739T3 (es)

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US9062158B2 (en) 2010-12-02 2015-06-23 Basf Se Polyester polyols based on aromatic dicarboxylic acids
US10472454B2 (en) 2012-01-18 2019-11-12 Basf Se Preparing rigid polyurethane foams
BR112014017049A8 (pt) 2012-01-18 2017-07-04 Basf Se processo para preparar espumas rígidas de poliuretano ou espumas rígidas de poli-isocianurato, espuma rígida de poliuretano ou poli-isocianurato, uso da espuma rígida de poliuretano ou poli-isocianurato, e, componente de poliol
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US8334035B2 (en) 2012-12-18
MX2011009917A (es) 2011-10-06
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KR101699098B1 (ko) 2017-02-01
RU2011145065A (ru) 2013-05-20
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