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Compound having silsesquioxane skeleton and its polymer

a technology of silsesquioxane and polymer, which is applied in the direction of silicon organic compounds, group 4/14 element organic compounds, synthetic resin layered products, etc., can solve the problems of poor compatibility of polyorganosiloxane, prone to cloudiness, and prone to whitening of coating film obtained from the coating agen

Inactive Publication Date: 2005-01-13
JNC PETROCHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In general, however, these polymers do not have a good compatibility with polyorganosiloxane.
Accordingly, there have been the problems that the coating agent is liable to become cloudy by blending polyorganosiloxane, and that a coating film obtained from the coating agent is liable to be whitened.
However, in the foregoing organic polymer having a polyorganosiloxane structure, such a high improving effect as expected has not been provided to the characteristics such as heat resistance, water repellency, weatherability and electric insulating property.

Method used

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  • Compound having silsesquioxane skeleton and its polymer
  • Compound having silsesquioxane skeleton and its polymer
  • Compound having silsesquioxane skeleton and its polymer

Examples

Experimental program
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example 1

<Production of Compound (1-3-7)>

Compound (1-3-7) was produced via the following route:

First Stage: Production of Allyl p-nitrophenyl Ether

Potassium carbonate (49.7 g, 0.36 mol) was added to an N,N-dimethylformamide (250 ml) solution of p-nitrophenol (25.0 g, 0.18 mol) under nitrogen atmosphere and suspended, and 3-bromopropene (21.7 g, 0.18 mol) was dropwise added thereto. After finishing dropwise adding, the solution was stirred at a room temperature for 5 hours, and then extracting practice with diethyl ether was carried out after adding water to the solution. The organic layer was washed with water and then dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue thus obtained was refined by means of silica gel chromatography (eluent solvent: toluene). Toluene was distilled off under reduced pressure, and then the resulting residue was recrystallized from ethanol to obtain allyl p-nitrophenyl ether (25.7 g).

Second St...

example 2

<Production of Compound (1-1-4)>

Compound (1-1-4) was produced via the following route:

THF (150 ml) was added to the compound (a) (50.0 g, 43.3 mmol) under nitrogen atmosphere and suspended, and a platinum-divinylsiloxane complex (3 wt % toluene solution, 320 μl) was added thereto and heated to 90° C. Allylsuccinic anhydride (14.5 g, 103.5 mmol) was dropwise added thereto in 5 minutes, and the solution was heated for 7 hours while refluxing. After standing to cool, the solvent was distilled off under reduced pressure, and then methanol (150 ml) was added to the resulting residue and stirred at a room temperature for 2 hours. The resulting solid matter was filtered and dissolved in THF (150 ml), and activated carbon (6 g) was added thereto, followed by stirring the mixture at a room temperature for 2 hours. After filtering off the activated carbon, THF was distilled off under reduced pressure to obtain Compound (1-1-4) 55.9 g.

1H-NMR (solvent: CDCl3): δ (ppm); 0.32 (s, 6H), 0...

example 3

<Production of Compound (1-1-1)>

Compound (1-1-1) was produced via the following route:

First Stage: Production of Compound (d)

3-Acetoxypropylmethyldichlorosilane (5.4 g, 25 mmol) was added to a mixture of a compound (c) (11.6 g, 10 mmol), triethylamine (2.5 g, 25 mmol) and THF (200 ml) under nitrogen atmosphere, and the solution was stirred at a room temperature for 3 hours. Toluene (200 ml) and water (100 ml) were added thereto and stirred, and the organic layer was washed with water and then dried on anhydrous magnesium sulfate. Toluene was distilled off under reduced pressure, and the residue thus obtained was washed with methanol and recrystallized from ethanol / ethyl acetate (100 ml) to obtain a compound (d) 6.51 g.

1H-NMR (solvent: CDCl3): δ (ppm); 0.31 (s, 6H), 0.72-0.75 (t, 4H), 1.70-1.74 (m, 4H), 1.88 (s, 6H), 3.91-3.94 (t, 4H), 7.18-7.52 (m, 40H). 29Si-NMR (solvent: CDCl3): δ (ppm); −17.8 (d, 2Si), −78.4 (s, 4Si), −79.3 (t, 4Si).

Second Stage: Production of Compo...

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Abstract

The present invention relates to a compound represented by Formula (1) and a polymer obtained using the compound: wherein R1 is phenyl which may have substituents, Q1 is hydrogen, halogen, alkyl having 1 to 10 carbon atoms, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl or phenyl in which optional hydrogen may be replaced by halogen or alkyl having 1 to 5 carbon atoms, and Q2 is a group represented by Formula (2) wherein the code < represents a bonding point with silicon, l, m, n and p are independently 0, 1, 2 or 3, A1 to A4 are independently a single bond, 1,4-cyclohexylene, 1,4-cyclohexenylene, a condensed ring group having 6 to 10 carbon atoms which is a divalent group, or 1,4-phenylene, Z0 to Z3 are independently a single bond, —CH═CR—, —C≡C—, —COO—, —OCO—, or alkylene having 1 to 20 carbon atoms, and Z4 is a single bond, —CH═CH—, —C≡C—, —COO—, —OCO—, or alkylene having 1 to 20 carbon atoms. And Y1 in Formula (1) is the group defined in Claim 1.

Description

FIELD OF THE INVENTION The present invention relates to a compound having a silsesquioxane skeleton, a polymer obtained using the compound, and uses of the polymer. BACKGROUND OF THE INVENTION Polyorganosiloxane has excellent heat resistance, weatherability and surface-modifying function, and therefore it is used for semiconductor insulating protective films, flame retardants and coating material additives. For example, a coating agent prepared by blending an organic polymer with polyorganosiloxane can provide the surface of a material coated with the agent with functions such as water repellency. The representative examples of the organic polymer are acryl resins, polyurethanes and alkid resins. In general, however, these polymers do not have a good compatibility with polyorganosiloxane. Accordingly, there have been the problems that the coating agent is liable to become cloudy by blending polyorganosiloxane, and that a coating film obtained from the coating agent is liable to be...

Claims

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Application Information

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IPC IPC(8): B32B27/00C07B61/00C07F7/21C08F30/08C08G59/30C08G63/695C08G69/42C08G73/10C08G77/04C08G77/42C08G77/455C08G85/00C09D5/00C09D133/08C09D133/10C09D163/00C09D167/00C09D177/00C09D179/08C09D183/14
CPCC07F7/21C08G59/306C08G63/695C09D183/14C08G77/045C08G77/42C08G77/455C08G69/42Y10T428/31663
Inventor INAGAKI, JYUN-ICHISASADA, YASUYUKIKATO, TAKASHI
Owner JNC PETROCHEM CORP
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