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Weatherable polycarbonate comprising N, N'-oxanilide structural units, its preparation method, and products made therefrom

A polycarbonate, structural unit technology, applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of no prompt, dark color, etc.

Inactive Publication Date: 2008-02-06
SABIC INNOVATIVE PLASTICS IP BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the N,N'-oxalanilide itself produced by the method suggested therein is very dark
And there is no suggestion that polycarbonate can be derived from such N,N'-oxanilide

Method used

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  • Weatherable polycarbonate comprising N, N'-oxanilide structural units, its preparation method, and products made therefrom
  • Weatherable polycarbonate comprising N, N'-oxanilide structural units, its preparation method, and products made therefrom
  • Weatherable polycarbonate comprising N, N'-oxanilide structural units, its preparation method, and products made therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067]

[0068] Synthesis of Compound (XII): To a cold (0°C) solution of freshly distilled anthranil (2.61 milliliters [ml], 20 millimoles [mmol]) in anhydrous dichloromethane (50 ml), add anhydrous Triethylamine (4.2ml, 30mmol) was followed by ethyl oxalyl chloride (2.25ml, 20.4mmol) dropwise over about 10 minutes. The reaction can be allowed to warm to room temperature and stir for 1 hour. Thin layer chromatography (TLC) with hexane / ethyl acetate indicated complete conversion of starting material. The reaction mixture was washed twice with 1N hydrochloric acid, twice with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the oxamate, compound (XII), with a purity greater than 99% by high performance liquid chromatography (HPLC) as a pale yellow with GC-MS: m / e 237.2 (M+) crystals.

Embodiment 2

[0070]

[0071]Synthetic compound (VI); Ar=2,2-(4,4'-phenylene) propyl (also known as compound (VIII)): oxamate, compound (XII), (2.415g, 10.18 mmol) and 2-(4-aminophenyl)-2-(4'-hydroxyphenyl)propane (2.545g, 11.2mmol) were suspended in o-dichlorobenzene (10ml), degassed, and heated to reflux 20 hours. TLC indicated complete conversion of oxamate. The reaction mixture starting material was concentrated under reduced pressure, taken up in dichloromethane, and filtered through a plug of silica gel. The product was recrystallized from hexane / dichloromethane and filtered again through silica gel to yield the desired N,N'-oxanilide as fine white crystals.

Embodiment 3

[0073] Synthetic compound (VI); Ar=4-phenylene: in a 25ml flask, add oxamate, compound (XII) (4.65g, 19.6mmol), pure p-aminophenol (3g, 27.5mmol), o-dichloro Benzene (12ml) and N,N-dimethylacetamide (2ml). The contents of the flask were degassed with a stream of nitrogen and then heated to 150°C for 10 hours. TLC indicated complete conversion of oxamate. The reaction mixture was concentrated under reduced pressure. Excess p-aminophenol was removed by trituration with ethyl acetate, and the remaining brown powder was recrystallized from ethyl acetate / methanol to give the crude product as a light brown powder.

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Abstract

In one embodiment the preset invention is a polycarbonate comprising structural units derived from at least one dihydric phenol, a carbonate precursor, and at least one member selected from the group consisting of an oxanilide-comprising compound, an oxamate-comprising compound, and mixtures thereof. In another embodiment the present invention is a method for making a polycarbonate comprising structural units derived from at least one dihydric phenol and at least one member selected from the group consisting of an oxanilide-comprising compound, an oxamate-comprising compound, and mixtures thereof, which comprises the step of contacting under reactive conditions at least one dihydric phenol, a carbonate precursor, and at least one member selected from the group consisting of an oxanilide-comprising compound, an oxamate-comprising compound, and mixtures thereof. In still another embodiment the present invention is an article comprising a policarbonate comprising oxanilide structural units. In still another embodiment the present invention is a method for making a symmetrical or unsymmetrical oxanilide-comprising dihydric phenol which comprises the step of contacting at least one aromatic amine bearing a hydroxy group with a diaryl oxalate or a dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group. In still another embodiment the present invention is a method for making an oxamate-comprising monohydric phenol which comprises the step of contacting an aromatic amine bearing a hydroxy group with a diaryl oxalate or a dialkyl oxalate bearing alkyl groups each substituted with at least one electron-withdrawing group.

Description

Background of the invention [0001] The present invention relates to weather-resistant polycarbonate, and more particularly, the present invention relates to weather-resistant polycarbonate containing N,N'-oxanilide structural unit, its manufacturing method, and the products produced therefrom. [0002] Polycarbonates are a widely used class of polymers, in part due to their excellent physical properties, including high impact strength. However, polycarbonate's resistance to changes upon exposure to atmospheric phenomena (commonly referred to as "weathering") is not ideal. In particular, the long-term stability of the color is an issue, since polycarbonate is prone to yellowing, which damages the clarity and charm of the polymer. Polycarbonate yellowing is primarily caused by the action of ultraviolet light, which is why this yellowing is often referred to as "photoyellowing". A number of methods have been used and proposed for inhibiting photoyellowing and other detrimental ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G64/12C07C233/56C07C231/02C07C69/36C07C69/63C07C233/24
CPCC07C69/63C08G64/12C07C233/24
Inventor 詹姆斯·E·皮克特泰比里厄·M·西克洛万约瑟夫·A·苏里亚诺丹尼尔·J·布鲁内里
Owner SABIC INNOVATIVE PLASTICS IP BV
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