Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
2001-02-28
2002-02-05
Acquah, Samuel A. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S307000
Reexamination Certificate
active
06344534
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel polyester polymer and a production process thereof. Specifically, the present invention relates to a polyester polymer having a high heat resistance and a low water absorption property, a low optical anisotropy, and a satisfactory formability (moldability), and to a production process of the polyester polymer. The polyester polymer is useful as, for example, an optical material, electronic information material, and medical device material.
2. Description of the Related Art
Intensive research and development on the application of a plastic to an optical material, electronic information material, and medical device material have been conducted in recent years. Such a plastic for use as an optical material or electronic information material must have a low optical anisotropy in addition to a high transparency, a low water absorption property and a high heat resistance. Likewise, a plastic for use as a medical device material must have satisfactory compatibility with blood, mechanical strength, and resistance to hydrolysis.
Poly(methyl methacrylate), polycarbonates, and amorphous polyolefins are used as the optical materials. However, poly(methyl methacrylate) has a high hygroscopicity to cause deformation such as warpage and has an insufficient heat resistance, although it is excellent in transparency and is low in optical anisotropy. A polycarbonate is high in optical anisotropy, although it is excellent in heat resistance. An amorphous polyolefin is insufficient in formability (moldability) and adhesive property, although it is low in optical anisotropy and is excellent in heat resistance.
Separately, attempts have been made to use a polyester polymer as an optical material or electronic information material. For example, Japanese Unexamined Patent Application Publication No. 1-138225 discloses a polyester resin obtained by using a diol or dicarboxylic acid having an aromatic ring in a side chain. Japanese Unexamined Patent Application Publication No. 2-38428 discloses a polyester copolymer obtained by using diphenyldicarboxylic acid as a dicarboxylic acid component. Japanese Unexamined Patent Application Publication No. 11-35665 discloses a polyester composed of a 2,2-norbornanedimethanol derivative, terephthalic acid, and other components. However, these resins do not always sufficiently have a high heat resistance, low water absorption property, and satisfactory optical characteristics.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide a novel polyester polymer which has a high heat resistance, a low water absorption property, and satisfactory optical characteristics and is excellent in formability, and to provide a production process of the polyester polymer.
After intensive investigations to achieve the above objects, the present inventors found that a polyester resin having a specific structure, specifically, a polyester resin having a tricyclo[5.2.1.0
2,6
]decane ring have a high heat resistance, low water absorption property, excellent optical characteristics, and satisfactory formability. The present invention has been accomplished based on these findings.
Specifically, the present invention provides, in an aspect, a polyester polymer which is a condensation product of a diol component and a dicarboxylic acid component. In the polyester polymer, (i) the diol component includes at least one tricyclo[5.2.1.0
2,6
]decanedimethanol represented by the following formula (1):
wherein two hydroxymethyl groups are bound to carbon atoms constituting tricyclo[5.2.1.0
2,6
]decane ring and wherein each of carbon atoms constituting the ring may have at least one additional substituent, or (ii) the dicarboxylic acid component includes at least one tricyclo[5.2.1.0
2,6
]decanedicarboxylic acid represented by the following formula (2):
wherein two carboxyl groups are bound to carbon atoms constituting tricyclo[5.2.1.0
2,6
]decane ring and wherein each of carbon atoms constituting the ring may have at least one additional substituent.
The polyester polymer includes, for example, a polyester polymer which is a condensation product of a diol component including at least one tricyclo[5.2.1.0
2,6
]decanedimethanol represented by the formula (1) with a dicarboxylic acid component, or a reactive derivative thereof, including at least one tricyclo[5.2.1.0
2,6
]decanedicarboxylic acid represented by the formula (2).
In another aspect, the present invention provides a process for producing a polyester polymer including the step of subjecting a diol component and a dicarboxylic acid component or a reactive derivative thereof to polycondensation. In the process, (i) a diol component including at least one tricyclo[5.2.1.0
2,6
]decanedimethanol represented by the formula (1) is used as the diol component; or (ii) a dicarboxylic acid component including at least one tricyclo[5.2.1.0
2,6
]decanedicarboxylic acid represented by the formula (2) or a reactive derivative thereof is used as the dicarboxylic acid component.
In an embodiment of the production process, a diol component including at least one tricyclo[5.2.1.0
2,6
]decanedimethanol represented by the formula (1) and a dicarboxylic acid component, or a reactive derivative, including at least one tricyclo[5.2.1.0
2,6
]decanedicarboxylic acid represented by the formula (2) are subjected to polycondensation.
As the diol component, a diol component can be used which includes at least one tricyclo[5.2.1.0
2,6
]decanedimethanol selected from among a tricyclo[5.2.1.0
2,6
]decane-3,8-dimethanol, a tricyclo[5.2.1.0
2,6
]decane-3,9-dimethanol, and tricyclo[5.2.1.0
2,6
]decane-4,8-dimethanol represented by the following formulae (1a) to (1c):
wherein each of carbon atoms constituting a ring may have at least one substituent. As the dicarboxylic acid component, a dicarboxylic acid component can be used, which includes at least one tricyclo[5.2.1.0
2,6
]decanedicarboxylic acid or a reactive derivative thereof selected from among a tricyclo[5.2.1.0
2,6
]decane-3,8-dicarboxylic acid, a tricyclo[5.2.1.0
2,6
]decane-3,9-dicarboxylic acid, and a tricyclo[5.2.1.0
2,6
]decane-4,8-dicarboxylic acid represented by the following formulae (2a) to (2c):
wherein each of carbon atoms constituting a ring may have at least one substituent.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
In tricyclo[5.2.1.0
2,6
]decanedimethanols represented by the formula (1), two hydroxymethyl groups indicated in the formula may be bound to any of carbon atoms constituting tricyclo[5.2.1.0
2,6
]decane ring (carbon atoms at the bridgehead position or at the non-bridgehead position). For example, assuming that the tricyclo[5.2.1.0
2,6
]decane ring is divided into a norbornane ring and a cyclopentane ring, the two hydroxymethyl groups may be bound to carbon atoms constituting the norbornane ring or may be bound to carbon atoms constituting the cyclopentane ring. Alternatively, it is acceptable that one hydroxymethyl group is bound to a carbon atom consisting the norbornane ring and the other is bound to a carbon atom constituting the cyclopentane ring. Each of these position isomers can be used alone or in combination. There are endo form and exo form in the tricyclo[5.2.1.0
2,6
]decanedimethanols represented by the formula (1), and either one or a mixture of these forms can be used in the present invention.
In the formula (1), each of carbon atoms constituting the ring (carbon atoms at the bridgehead position or at the non-bridgehead position) may have at least one substituent in addition to the two hydroxymethyl groups. Such additional substituents include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, decyl, and other alkyl groups (e.g., C
1
-C
10
alkyl groups, and preferably C
1
-C
4
alkyl groups
He Shougang
Teranishi Tadashi
Acquah Samuel A.
Daicel Chemical Industries Ltd.
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