ES2525146T5 - Resina de poliéster insaturada - Google Patents
Resina de poliéster insaturada Download PDFInfo
- Publication number
- ES2525146T5 ES2525146T5 ES10710043.0T ES10710043T ES2525146T5 ES 2525146 T5 ES2525146 T5 ES 2525146T5 ES 10710043 T ES10710043 T ES 10710043T ES 2525146 T5 ES2525146 T5 ES 2525146T5
- Authority
- ES
- Spain
- Prior art keywords
- resin
- unsaturated polyester
- polyester resin
- nmr
- mpa
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- 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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- 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]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- 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]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- 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]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
- Y10T428/1393—Multilayer [continuous layer]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
Description
Se controló el curado mediante equipo de tiempo de gel clásico. Esto quiere decir que tanto el tiempo de gel (Tgel o T25->35°C) como tiempo máximo (Tmáxima o T25 ->máxima) se determinaron mediante mediciones de exotermas según el método de DIN 16945 cuando se cura la resina con el peróxido como se indica.
Determinación de propiedad mecánica
5 Para la determinación de las propiedades mecánicas se prepararon piezas fundidas de 4 mm. Después de 16 h se liberaron las piezas fundidas del molde y se postcuraron usando 24 h a 60°C seguido por 24 h a 80°C.
Las propiedades mecánicas de los objetos curados se determinaron según ISO 527-2. Se midió la Temperatura de Distorsión Térmica (HDT) según ISO 75-A.
Se determinó la viscosidad de la resina disuelta a 23°C usando un instrumento Physica.
10 Se determinó la dureza Barcoll según DIN EN59.
Ejemplo 1-3
A continuación del procedimiento de síntesis clásico se prepararon diversas resinas usando un total de 732 g de ácido itacónico, citracónico y mesacónico como materiales de partida junto con 471 g de 1,3-o 1,2-propanodiol. El análisis de RMN de 1H (Varian 300 MHz) reveló la relación entre los diversos componentes en la resina preparada. A
15 continuación se diluyó la resina con estireno y se determinaron el contenido en sólido y la viscosidad. Se curaron las resinas después de dilución usando 0,5% en peso de una disolución de cobalto (NL-49P) seguido por 2% en peso de Trigonox 44B como peróxido y se determinaron las propiedades mecánicas.
Tabla 1
- Ejemplo 1
- Ejemplo 2 Ejemplo 3 (NO SEGÚN LA INVENCIÓN)
- diol
- 1,3-propanodiol 1,2-propanodiol 1,2-propanodiol
- Itacónico en resina (RMN) (%)
- 78 56 18
- Citracónico en resina (RMN) (%)
- 10 18 32
- Mesacónico en resina (RMN) (%)
- 12 25 50
- Sólidos (%)
- 65 65 66
- Viscosidad @23°C (mPa.s)
- 668 747 258
- Tiempo de gel (min)
- 320 136 60,6
- Tiempo máximo (min)
- 334 151 85
- Temperatura máxima (ºC)
- 143 135 108
- Resistencia a la tracción (MPa)
- 63 79 57,4
- Módulo de tracción (GPa)
- 3,0 3,4 3,0
- Elongación en la rotura (%)
- 3,1 4,0 2,3
- Resistencia a la flexión (MPa)
- 90 107 113
- Módulo de flexión (GPa)
- 2,8 3,2 2,8
- HDT (ºC)
- 105 96 65
- Dureza Barcol
- 43 40 43
20 Los Ejemplos 1 y 2 demuestran claramente que empleando poliésteres insaturados con la relación de itacónico/citracónico y mesacónico según una realización preferida de la invención, se puede obtener la mejor combinación de propiedades mecánicas, es decir, alta estabilidad térmica como se indica por HDT junto con una flexibilidad aumentada cuando se mide con la elongación en la rotura. Además, estos ejemplos demuestran que se pueden usar diversos dioles sin que afecte de manera negativa a las propiedades mecánicas favorables de la resina
25 especialmente la HDT del material compuesto curado. En general, estos ejemplos demuestran la idoneidad de la combinación según la invención para la preparación de resinas de poliéster insaturado adecuadas para fines de construcción.
Ejemplo 4 y 5
7
- Mesacónico en resina (RMN) (%)
- 43 11 15 16
- Sólidos (%)
- 65 65 65 65
- Viscosidad @23°C (mPa.s)
- 382 447 596 525
- Tiempo de gel (min)
- 71 42 134 152
- Tiempo máximo (min)
- 102 80 147 159
- Temperatura máxima (ºC)
- 65 79 163 147
- Resistencia a la tracción (MPa)
- 58 53 63 60
- Módulo de tracción (GPa)
- 2,5 3,5 3,2 3,3
- Elongación en la rotura (%)
- 3,8 1,7 2,6 2,2
- Resistencia a la flexión (MPa)
- 102 114 106 106
- Módulo de flexión (GPa)
- 2,5 3,3 3,1 3,5
- HDT (ºC)
- 52 100 111 109
- Dureza Barcol
- 39 50 49 48
La comparación del Ejemplo 6 con el Ejemplo 7 muestra que las propiedades mecánicas del objeto curado se pueden ajustar con la relación isomérica en la resina de poliéster insaturado. Además, se usa preferiblemente para obtener una alta HDT, una relación de itaconato de 50 a 80% en moles, citraconato de 5 a 20% en moles y mesaconato de 10
5 a 30% en moles de unidades de éster. Además, la comparación de los ejemplos 7, 8 y 9 muestra sorprendentemente que la alta HDT se determina más por la relación isomérica que por los dioles usados.
Ejemplos 10-13
Después del procedimiento de síntesis clásico se prepararon diversas resinas usando un total de 732 g de ácido itacónico, citracónico y mesacónico como materiales de partida junto con x g de diversos dioles. El análisis de RMN
10 de 1H (300 MHz) reveló la relación entre los diversos componentes en la resina. A continuación se diluyó la resina con estireno y se determinaron el contenido en sólidos y la viscosidad. Se curaron las resinas después de dilución usando 0,5% en peso de una disolución de cobalto (NL-49P) seguido por 2% en peso de Trigonox 44B como peróxido y se determinaron las propiedades mecánicas. Véase la Tabla 4.
Tabla 4
- Ejemplo 10
- Ejemplo 11 Ejemplo 12 Ejemplo 13
- Diol usado
- 1,2-propanodiol (g)
- 164,8 235,5 253,2
- 1,3-propanodiol (g)
- 235,5
- 2,3-butanodiol (g)
- 362,6 557,8
- Isosorbida (g)
- 226,14
- Itacónico en resina (RMN) (%)
- 45 52 76 66
- Citracónico en resina (RMN) (%)
- 15 14 9 11
- Mesacónico en resina (RMN) (%)
- 40 34 15 23
- Sólidos (%)
- 64 65 64 65
- Viscosidad @23°C (mPa.s)
- 496 744 735 780
- Tiempo de gel (min)
- 124 124 189 130
- Tiempo máximo (min)
- 142 142 212 141
- Temperatura máxima (ºC)
- 110 110 107 149
- Resistencia a la tracción (MPa)
- 70 50 65 76
- Módulo de tracción (GPa)
- 3,7 3,7 3,1 3,5
9
Claims (1)
-
imagen1
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09156137 | 2009-03-25 | ||
EP09156131 | 2009-03-25 | ||
EP09156142 | 2009-03-25 | ||
EP09156130 | 2009-03-25 | ||
EP09156130 | 2009-03-25 | ||
EP09156131 | 2009-03-25 | ||
EP09156137 | 2009-03-25 | ||
EP09156139 | 2009-03-25 | ||
EP09156139 | 2009-03-25 | ||
EP09156142 | 2009-03-25 | ||
PCT/EP2010/053850 WO2010108965A1 (en) | 2009-03-25 | 2010-03-24 | Unsaturated polyester resin |
Publications (2)
Publication Number | Publication Date |
---|---|
ES2525146T3 ES2525146T3 (es) | 2014-12-18 |
ES2525146T5 true ES2525146T5 (es) | 2018-04-12 |
Family
ID=42124624
Family Applications (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES10709856.8T Active ES2477891T3 (es) | 2009-03-25 | 2010-03-24 | Composición de resina poliéster insaturada |
ES10710044.8T Active ES2499190T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
ES10709858.4T Active ES2567166T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
ES10710043.0T Active ES2525146T5 (es) | 2009-03-25 | 2010-03-24 | Resina de poliéster insaturada |
ES10710042.2T Active ES2524373T3 (es) | 2009-03-25 | 2010-03-24 | Poliéster insaturado |
ES10709857T Active ES2555218T5 (es) | 2009-03-25 | 2010-03-24 | Resina de poliéster insaturado |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES10709856.8T Active ES2477891T3 (es) | 2009-03-25 | 2010-03-24 | Composición de resina poliéster insaturada |
ES10710044.8T Active ES2499190T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
ES10709858.4T Active ES2567166T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES10710042.2T Active ES2524373T3 (es) | 2009-03-25 | 2010-03-24 | Poliéster insaturado |
ES10709857T Active ES2555218T5 (es) | 2009-03-25 | 2010-03-24 | Resina de poliéster insaturado |
Country Status (8)
Country | Link |
---|---|
US (6) | US20120157618A1 (es) |
EP (6) | EP2411444B1 (es) |
JP (6) | JP2012521466A (es) |
CN (6) | CN102361905B (es) |
BR (6) | BRPI1011743B1 (es) |
DK (3) | DK2411443T4 (es) |
ES (6) | ES2477891T3 (es) |
WO (6) | WO2010108968A1 (es) |
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