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.)
- Active
Links
- 229920006337 unsaturated polyester resin Polymers 0.000 title description 3
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 3
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 101100165342 Arabidopsis thaliana BHLH110 gene Proteins 0.000 description 1
- ZIAATLFARDAYAG-UHFFFAOYSA-N C(C(C)O)O.C(C(C)O)O.C(CCO)O Chemical compound C(C(C)O)O.C(C(C)O)O.C(CCO)O ZIAATLFARDAYAG-UHFFFAOYSA-N 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 229940018560 citraconate Drugs 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
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)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (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 |
|---|---|---|---|
| EP09156131 | 2009-03-25 | ||
| EP09156130 | 2009-03-25 | ||
| EP09156131 | 2009-03-25 | ||
| EP09156130 | 2009-03-25 | ||
| EP09156142 | 2009-03-25 | ||
| EP09156139 | 2009-03-25 | ||
| EP09156137 | 2009-03-25 | ||
| EP09156137 | 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 |
|---|---|---|---|
| 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 |
| ES10710044.8T Active ES2499190T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
| ES10709856.8T Active ES2477891T3 (es) | 2009-03-25 | 2010-03-24 | Composición de resina poliéster insaturada |
| ES10709858.4T Active ES2567166T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
| ES10709857T Active ES2555218T5 (es) | 2009-03-25 | 2010-03-24 | Resina de poliéster insaturado |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10710042.2T Active ES2524373T3 (es) | 2009-03-25 | 2010-03-24 | Poliéster insaturado |
| ES10710044.8T Active ES2499190T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
| ES10709856.8T Active ES2477891T3 (es) | 2009-03-25 | 2010-03-24 | Composición de resina poliéster insaturada |
| ES10709858.4T Active ES2567166T5 (es) | 2009-03-25 | 2010-03-24 | Proceso para preparación de poliésteres insaturados |
| ES10709857T Active ES2555218T5 (es) | 2009-03-25 | 2010-03-24 | Resina de poliéster insaturado |
Country Status (8)
| Country | Link |
|---|---|
| US (6) | US8470926B2 (es) |
| EP (6) | EP2411445B2 (es) |
| JP (6) | JP2012521470A (es) |
| CN (6) | CN102361909B (es) |
| BR (6) | BRPI1011702B1 (es) |
| DK (3) | DK2411442T4 (es) |
| ES (6) | ES2525146T5 (es) |
| WO (6) | WO2010108962A1 (es) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI1011702B1 (pt) * | 2009-03-25 | 2020-10-20 | Dsm Ip Assets B.V. | processo para preparação de uma resina, composição de resina, objeto curado ou peça estrutural e uso dos mesmos e composição de revestimento em pó |
| JP5610194B2 (ja) * | 2010-04-19 | 2014-10-22 | 三菱レイヨン株式会社 | トナー用ポリエステル樹脂およびその製造方法 |
| JP5541522B2 (ja) * | 2010-11-04 | 2014-07-09 | Ｄｉｃ化工株式会社 | 成形材料、成形品、床材及び成形品の製造方法 |
| WO2012130963A1 (en) * | 2011-03-30 | 2012-10-04 | Dsm Ip Assets B.V. | Unsaturated polyester resin composition |
| JP2014509673A (ja) * | 2011-03-30 | 2014-04-21 | ディーエスエム アイピー アセッツ ビー．ブイ． | 不飽和ポリエステル樹脂組成物 |
| US20120296019A1 (en) * | 2011-05-18 | 2012-11-22 | Haseena Aripuram Parakkal | High heat and flame retardant bio-sourced polycarbonate |
| US8933170B2 (en) | 2011-05-18 | 2015-01-13 | Sabic Global Technologies B.V. | Bio-sourced transparent and ductile polycarbonate blends |
| US8841404B2 (en) | 2011-05-18 | 2014-09-23 | Sabic Global Technologies B.V. | Flame retardant bio-based polymer blends |
| CN103059310B (zh) * | 2011-10-21 | 2015-04-29 | 中国科学院化学研究所 | 一种含有双键的可生物降解聚酯多嵌段共聚物及其制备方法 |
| JP2013159715A (ja) * | 2012-02-06 | 2013-08-19 | Panasonic Corp | 不飽和ポリエステル樹脂材料、及び不飽和ポリエステル樹脂材料を成形して成る繊維強化プラスチック成形材料 |
| US20130261254A1 (en) * | 2012-03-30 | 2013-10-03 | Segetis, Inc. | Reactive diluents, methods of reacting, and thermoset polymers derived therefrom |
| JPWO2013183196A1 (ja) * | 2012-06-05 | 2016-01-28 | パナソニックＩｐマネジメント株式会社 | 不飽和ポリエステル樹脂、不飽和ポリエステル樹脂材料、及び不飽和ポリエステル樹脂材料を成形して成る繊維強化プラスチック成形材料 |
| US9290615B2 (en) | 2012-06-13 | 2016-03-22 | Mitsubishi Rayon Co., Ltd. | Toner polyester resin, method for producing same, and toner |
| JP6446781B2 (ja) * | 2012-12-07 | 2019-01-09 | 三菱ケミカル株式会社 | トナー用ポリエステル樹脂、その製造方法、およびトナー |
| CN103351923A (zh) * | 2013-06-19 | 2013-10-16 | 安徽富华电子集团有限公司 | 铜铝拉丝液及其制备方法 |
| CN103351919A (zh) * | 2013-06-19 | 2013-10-16 | 安徽富华电子集团有限公司 | 微乳半合成铜拉丝液组合物及其制备方法 |
| CN103351915A (zh) * | 2013-06-19 | 2013-10-16 | 安徽富华电子集团有限公司 | 一种金属拉丝润滑剂及其制备方法 |
| CN103351918A (zh) * | 2013-06-19 | 2013-10-16 | 安徽富华电子集团有限公司 | 一种水性拉丝润滑剂及其制备方法 |
| CN103351920A (zh) * | 2013-06-19 | 2013-10-16 | 安徽富华电子集团有限公司 | 一种铜线高速细拉丝润滑液及其制备方法 |
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