ES2549139T3 - Copolicarbonatos, sus derivados y el uso de los mismos en composiciones de recubrimiento duro de silicona - Google Patents

Copolicarbonatos, sus derivados y el uso de los mismos en composiciones de recubrimiento duro de silicona Download PDF

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Publication number
ES2549139T3
ES2549139T3 ES12708216.2T ES12708216T ES2549139T3 ES 2549139 T3 ES2549139 T3 ES 2549139T3 ES 12708216 T ES12708216 T ES 12708216T ES 2549139 T3 ES2549139 T3 ES 2549139T3
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okay
phc
oligomer
copolycarbonates
derivatives
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Christoph Hilgers
Anantharaman Dhanabalan
Narayana Padmanabha Iyer
Shayne Joseph Landon
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Momentive Performance Materials Inc
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Momentive Performance Materials Inc
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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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/0266—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/06—Polyurethanes from 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31507—Of polycarbonate
    • 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Un copolicarbonato que comprende unidades de repetición A y B respectivamente de las fórmulas:**Fórmula** y en la que la relación molar de unidades (A) a unidades (B) está en el intervalo de 9:1 a 1:9, y en la que R1 es un grupo alicíclico C8 a C12 divalente, R2 es un grupo divalente seleccionado del grupo que consiste en etileno y propileno, n es un número entero que varía de 4 a 40.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
E12708216
02-10-2015
8
Oligómero 6 parcialmente sililado preparado de acuerdo con el ejemplo 2 (se sililaron el 60 % en moles de los grupos hidroxilo en el oligómero 6 con isocianatopropiltrimetoxisilano)
9
Poliuretano preparado de acuerdo con el ejemplo 3 excepto que el diol usado era TCDDM-PPG425 (oligómero 6)
10
Poliuretano sililado completamente preparado de acuerdo con el ejemplo 4 excepto que el poliuretano usado era el oligómero 9
Tabla 3
PHC 5871 (% p9 de MTMS8)
Oligómero Cantidad de Oligómero (% p)9 Ensayo de Kaercher Δ turbidez3 500 ciclos Elongación a rotura 4 (%) Resistencia a la lana de acero 5 Ensayo de cinta (10d)6
Referencia 7 (comparativa) 100
0 F4 4,5 1,5 OK OK
90
1 10 Grietas
95
1 5 F0 5,1 1,8 OK OK
90
2 10 F0 6,2 2,1 OK OK
90
3 10 F0 6,3 2,3 OK OK
95
4 5 F0 4,5 1,5 OK OK
90
4 10 F0 2,0 1,8 OK OK
95
5 5 F0 1,6 1,8 OK OK
90
5 10 F0 1,6 1,8 OK OK
95
6 5 F0 1,8 1,8 OK OK
90
6 10 F0 1,8 1,9 OK OK
95
7 5 F0 2,3 1,8 OK OK
90
7 10 F0 2,4 1,8 OK OK
95
8 5 F0 1,6 1,8 OK OK
90
8 10 F0 2,4 1,8 OK OK
95
9 5 F0 2,3 1,8 OK OK
90
9 10 F0 2,5 1,8 OK OK
95
10 5 F0 1,8 1,7 OK OK
90
10 10 F0 2,2 1,7 OK OK
1 PHC 587 sin promotor de adherencia 2 Medido de acuerdo con DIN 55662:2009 3 Se midió la abrasión Taber de acuerdo con la ASTM D-1044. La resistencia a la abrasión se determinó mediante el cambio de turbidez después de unos ciclos taber predeterminados. Un bajo delta de turbidez indica una buena resistencia a la abrasión. 4 Ensayo de flexión en tres puntos para medir la elongación hasta agrietarse (estrés de extensión externa) de acuerdo con DIN EN ISO 178 convencional. 5 La resistencia a la lana de acero de la muestra se examinó al usar lana de acero para frotar la muestra. OK significa que se causó ningún rasguño o un rasguño aceptable al rozar la muestra con la lana de acero. 6 Adherencia medida de acuerdo con la ASTM D3359. 7 PHC 587 convencional que contiene un promotor de adherencia poliol acrílico. 8 MTMS se refiere a metil trimetoxi silano 9 El porcentaje se basa en el peso total de MTMS y el oligómero.
Tabla 4
PHC 5871 (% p5 de MTMS4)
Oligómero Cantidad del Oligómero (% p)5 Ensayo de Karcher2 (5 CF) Ensayo de Karcher2 (10 CF)
Referencia 13 (comparativa) 100
0 F4 -
Referencia 24 (comparativa) 100
0 F4 -
97,5
1 2,5 F0 F3
95
1 5 F0 F2
92,5
1 7,5 F0 F0
90
1 10 F5 -
97,5
3 2,5 F0 F0
95
3 5 F0 F0
92,5
3 7,5 F0 F0
90
3 10 F0 F2
10
E12708216
02-10-2015
1 PHC 587 sin promotor de adherencia 2 Medido de acuerdo con DIN 55662:2009, tras 5 y 10 ciclos CF. 3 PHC 587 convencional que contiene un promotor de adherencia poliol acrílico 4 PHC 587 sin ningún promotor de adherencia 5 MTMS se refiere a metil trimetoxi silano 6 El porcentaje se basa en el peso total de MTMS y el oligómero.
Tabla 5
Tiempo en horas1
kj PHC 5875 con 2,5 % p de Oligómero 1 PHC 5875 con 2,5 % p de Oligómero 3 PHC 587 convencional6 (comparativo)
y.i.2
Turbidez3 Transm4 y.i.2 Turbidez3 Transm4 y.i.2 Turbidez3 Transm4
0
0
-0,77 0,38 90,2 -1,07 0,38 90,3 0,45 0,2 89,6
550
1490 -1,1 0,36 90,6 -1,36 0,75 90,5 0,14 0,31 90,1
1100
2980 0,03 1,02 90,7 -0,25 0,59 90,9 0,1 0,42 90,2
1650
4470 0,59 1,01 90,5 0,52 1,3 90,5 0,21 0,63 90,3
2200
5960 0,54 0,46 90,5 0,58 0,75 90,8 0,27 0,42 90,3
2750
7450 1,39 0,59 90,8 1,16 0,99 91,1 0,88 0,67 89,9
3300
8940 2,88 1,49 90,9 3,07 2,71 90,3 1,68 0,82 89,9
1 ASTM G155 mod (0,75 W/m2 @ 340 nm) 2 De acuerdo con la ASTM E313 3 De acuerdo con la ASTM D 1003 4 De acuerdo con la ASTM D 1003 5 PHC 587 sin promotor de adherencia 6 PHC 587 con promotor de adherencia poliol acrílico convencional
11

Claims (1)

  1. imagen1
    imagen2
ES12708216.2T 2011-02-28 2012-02-27 Copolicarbonatos, sus derivados y el uso de los mismos en composiciones de recubrimiento duro de silicona Active ES2549139T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13/036,307 US8637157B2 (en) 2011-02-28 2011-02-28 Copolycarbonates, their derivatives and the use thereof in silicone hardcoat compositions
US201113036307 2011-02-28
PCT/US2012/026747 WO2012118739A1 (en) 2011-02-28 2012-02-27 Copolycarbonates, their derivatives and the use thereof in silicone hardcoat compositions

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US (1) US8637157B2 (es)
EP (1) EP2681256B1 (es)
JP (1) JP2014508834A (es)
KR (1) KR20140005291A (es)
CN (1) CN103492456B (es)
BR (1) BR112013022004A2 (es)
ES (1) ES2549139T3 (es)
MX (1) MX2013009821A (es)
TW (1) TW201241042A (es)
WO (1) WO2012118739A1 (es)

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US8637157B2 (en) 2014-01-28
MX2013009821A (es) 2014-01-08
CN103492456B (zh) 2016-01-20
BR112013022004A2 (pt) 2016-11-29
KR20140005291A (ko) 2014-01-14
EP2681256A1 (en) 2014-01-08
JP2014508834A (ja) 2014-04-10
CN103492456A (zh) 2014-01-01
TW201241042A (en) 2012-10-16
WO2012118739A1 (en) 2012-09-07
EP2681256B1 (en) 2015-09-16
US20120219802A1 (en) 2012-08-30

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