KR101743352B1 - Polycarbonate based resin and method for preparing the same - Google Patents
Polycarbonate based resin and method for preparing the same Download PDFInfo
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- KR101743352B1 KR101743352B1 KR1020150093813A KR20150093813A KR101743352B1 KR 101743352 B1 KR101743352 B1 KR 101743352B1 KR 1020150093813 A KR1020150093813 A KR 1020150093813A KR 20150093813 A KR20150093813 A KR 20150093813A KR 101743352 B1 KR101743352 B1 KR 101743352B1
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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
- C08G64/18—Block or graft polymers
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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
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
Abstract
The polycarbonate resin of the present invention comprises a repeating unit represented by the following formula (1); And a repeating unit represented by the following formula (2). The polycarbonate resin is excellent in weather resistance, workability, impact resistance and the like.
[Chemical Formula 1]
R 1 and R 2 are independently an alkyl group having 1 to 10 carbon atoms or a halogen atom, A is a single bond, a hydrocarbon group having 1 to 12 carbon atoms, -CO-, -O-, -S- or -SO 2 -, a and b are each independently an integer of 0 to 4 and the average value of n is 5 to 200;
(2)
In the formula 1, R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a methyl group, Ar is an arylene group having 6 to 12 carbon atoms, m has an average value of 0 to 2, The average value is independently 0 to 1.
Description
The present invention relates to a polycarbonate resin and a method for producing the same. More specifically, the present invention relates to a polycarbonate resin excellent in weather resistance, workability and impact resistance, a method for producing the same, and a molded article comprising the same.
Polycarbonate resins are excellent in mechanical properties, thermal properties, transparency, and are used in a wide range of applications. Polycarbonate resin is also used as an outdoor material. In this case, the color change of the product by ultraviolet (UV) should be small. Thus, in order to improve the weather resistance (reduction of color change due to ultraviolet rays) of the polycarbonate resin, a method of adding an additive such as a UV stabilizer to the resin or blending the resin with another resin is mainly used.
However, a conventional ultraviolet stabilizer is a low molecular weight substance, which may cause gas generation and discoloration at the time of processing the resin, which may lower the chemical resistance and the like. Further, when two or more kinds of resins are blended, the permeability and impact resistance of the resin composition may be lowered due to the lowered compatibility between the resins.
Further, in order to improve the weather resistance and the like, a polyester carbonate copolymer containing an aromatic ester group is synthesized by using an aromatic diol and an aromatic dicarboxylic acid. However, such a copolymer has an excessively high glass transition temperature, There is a possibility that the workability is lowered.
Therefore, development of a polycarbonate resin which is excellent in weather resistance and the like and which is suitable as an outdoor material is demanded without deteriorating impact resistance, workability, chemical resistance, permeability, and the like.
The background art of the present invention is disclosed in U.S. Patent No. 6,143,839.
An object of the present invention is to provide a polycarbonate resin excellent in weather resistance, workability, impact resistance and the like and a method for producing the same.
Another object of the present invention is to provide a molded article comprising the polycarbonate-based resin.
The above and other objects of the present invention can be achieved by the present invention described below.
One aspect of the present invention relates to a polycarbonate-based resin. Wherein the polycarbonate resin comprises a repeating unit represented by the following formula (1); And a repeating unit represented by the following formula (2):
[Chemical Formula 1]
R 1 and R 2 are independently an alkyl group having 1 to 10 carbon atoms or a halogen atom, A is a single bond, a hydrocarbon group having 1 to 12 carbon atoms, -CO-, -O-, -S- or -SO 2 -, a and b are each independently an integer of 0 to 4 and the average value of n is 5 to 200;
(2)
In the formula 1, R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a methyl group, Ar is an arylene group having 6 to 12 carbon atoms, m has an average value of 0 to 2, The average value is independently 0 to 1.
In an embodiment, the polycarbonate resin may include 100 molar parts of the repeating unit represented by the formula (1) and 0.5 to 30 mol parts of the repeating unit represented by the formula (2).
In an embodiment, the weight average molecular weight of the polycarbonate-based resin may be 10,000 to 200,000 g / mol.
In an embodiment, the polycarbonate-based resin may have a yellow index difference (? YI) of 12 or less before and after ultraviolet (UV) irradiation measured according to the following formula 1:
[Formula 1]
Difference in yellow index before and after ultraviolet irradiation (ΔYI) = YI 1 - YI 0
YI 0 is the yellow index of the 2.5 mm thick specimen measured according to ASTM D1925 and YI 1 is the ultraviolet ray (UV) of the specimen at 313 nm and 0.63 W / m 2 at 60 ° C for 24 hours And then measured according to ASTM D1925.
In an embodiment, the polycarbonate-based resin may have a glass transition temperature of 120 to 170 캜.
In an embodiment, the polycarbonate-based resin may have an Izod impact strength of 70 to 100 kgf · cm / cm for a 1/8 "thick specimen measured according to ASTM D256.
Another aspect of the present invention relates to a method for producing the polycarbonate-based resin. The method comprises reacting a polycarbonate resin having a weight average molecular weight of 2,500 to 50,000 g / mol and a repeating unit represented by the following formula (3) and a compound represented by the following formula (4)
(3)
[Chemical Formula 4]
Wherein R 1 , R 2 , R 3 , R 4 , A, Ar, a and b are as defined in the above formulas (1) and (2).
In an embodiment, the reaction may be carried out by reacting 0.5 to 30 parts by mol of the compound represented by the formula (3) with 100 parts by mol of the polycarbonate resin.
In embodiments, the reaction may be carried out at 150 to 350 < 0 > C.
In an embodiment, the reaction may be by melt polymerization.
Another aspect of the present invention relates to a molded article formed from a resin composition containing the polycarbonate-based resin.
The present invention has the effect of providing a polycarbonate resin excellent in weather resistance, workability and impact resistance, a method for producing the same, and a molded article comprising the same.
Hereinafter, the present invention will be described in detail.
The polycarbonate resin according to the present invention is characterized by comprising a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2).
[Chemical Formula 1]
(2)
Wherein R 1 and R 2 are each independently an alkyl group having 1 to 10 carbon atoms or a halogen atom such as methyl, ethyl, propyl, butyl, pentyl, hexyl, Cl, F or Br, R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a methyl group, A is a single bond, a hydrocarbon group having 1 to 12 carbon atoms, -CO-, -O-, -S- Or -SO 2 -, for example, a single bond, an alkylene group of 1 to 10 carbon atoms, an alkylidene group of 2 to 10 carbon atoms, a cycloalkylene group of 5 to 12 carbon atoms, or a cycloalkylidene group, And a and b are each independently an integer of 0 to 4, and the average value of n may be 5 to 200, for example, 10 to 180, specifically 20 to 150, and the average value of m is 0 To 2, such as 0 to 1, specifically 0, and the average values of p and q are each independently 0 to 1, Surface may be 0.1 to 0.9 days.
In a specific example, the polycarbonate resin comprising the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) includes a repeating unit represented by the following formula (1a), a repeating unit represented by the following formula , And a repeating unit represented by the following formula (1d), but is not limited thereto.
[Formula 1a]
[Chemical Formula 1b]
[Chemical Formula 1c]
≪ RTI ID = 0.0 &
In the above formulas (1a), (1b), (1c) and (1d), n is as defined in the above formula (1).
The polycarbonate resin according to one embodiment of the present invention is produced by reacting a polycarbonate resin having a weight average molecular weight (Mw) of 2,500 to 50,000 g / mol and a repeating unit represented by the following formula (3) Can be manufactured.
(3)
[Chemical Formula 4]
Wherein R 1 , R 2 , R 3 , R 4 , A, Ar, a and b are as defined in the above formulas (1) and (2).
In an embodiment, the polycarbonate resin is a conventional aromatic polycarbonate resin having a weight average molecular weight of 2,500 to 50,000 g / mol, such as 5,000 to 35,000 g / mol, for example, a poly Carbonate resin. In the weight-average molecular weight range, a polycarbonate resin improved in weatherability and the like can be obtained without deteriorating the physical properties of the conventional polycarbonate resin.
In an embodiment, the polycarbonate resin may be prepared by reacting an aromatic diol compound with phosgene in the presence of a molecular weight modifier and a catalyst, or by reacting an aromatic diol compound with an aromatic carbonic ester compound such as diphenyl carbonate Precursor) can be prepared by transesterification.
In an embodiment, the aromatic diol compound may be a diol compound represented by the following formula (5).
[Chemical Formula 5]
Wherein R 1 , R 2 , A, a and b are the same as defined in the above formula (1).
In an embodiment, the aromatic diol compound is selected from the group consisting of 2,2-bis (4-hydroxyphenyl) propane (hereinafter referred to as bisphenol A), 4,4'-biphenol, bis Bis (3-methyl-4-hydroxyphenyl) propane, 2,2-bis (3,5-dimethyl-4-hydroxyphenyl) propane Bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) sulfone, bis Ether, 2,2-bis (3,5-dibromo-4-hydroxyphenyl) propane, combinations thereof, and the like.
In an embodiment, the polycarbonate resin may have the form of a linear polycarbonate resin, a branched polycarbonate resin, or the like.
In an embodiment, the polycarbonate resin may comprise a terminally modified polycarbonate resin comprising a tert-butylphenoxy group end. The terminal-modified polycarbonate resin can be produced according to a conventional polycarbonate resin production method, except that tert-butylphenol is added in the production of polycarbonate resin. In the case of including the terminal-modified polycarbonate resin, the content of the tert-butylphenoxy group in the entire polycarbonate resin may be 0.1 to 80 mol%, for example, 20 to 60 mol%. The impact resistance and the like of the polycarbonate resin in the above range can be improved.
(2-hydroxyethyl) terephthalate, bis (2-hydroxyethyl) naphthalate, bis (2-hydroxyethyl) Hydroxypropyl) naphthalate, and the like, but are not limited thereto.
In the embodiment, the polycarbonate resin reacts with the polycarbonate resin and the compound represented by Chemical Formula 4 as shown in Reaction Scheme 1 below to form an unstable intermediate, and carbon dioxide and / or cyclic alkylene carbonate (Ethylene carbonate or propylene carbonate). Herein, the compound represented by Formula 4 may form a repeating unit represented by Formula 2 with an average value of m exceeding 0 by the reaction between compounds, and R 5 and R 6 in Formula 2 may be the same as Formula 4 Of R < 3 > or R < 4 >. In addition, the following Reaction Scheme 1 shows the case where m in Formula 2 is 0, but it is not limited thereto.
[Reaction Scheme 1]
R 1 , R 2 , R 3 , R 4 , A, Ar, a and b are as defined in the above formulas (1) and (2).
In an embodiment, the reaction may be carried out by reacting 0.5 to 30 moles, for example, 1 to 20 moles, of the compound represented by the formula (4) per 100 moles of the polycarbonate resin. The impact resistance, weather resistance and the like can be improved without lowering the processability of the polycarbonate resin within the above range.
In an embodiment, the reaction may be by melt polymerization. For example, the reaction may be conducted at a temperature of 150 to 350 ° C, for example, 160 to 310 ° C, under a nitrogen atmosphere. In the above range, the reaction rate is fast, and carbon dioxide and / or cyclic alkylene carbonate (ethylene carbonate or propylene carbonate) is escaped from the intermediate as a by-product, and a polycarbonate resin containing an ester bond in the main chain can be produced. Further, the reaction can be carried out under atmospheric pressure or reduced pressure. For example, under a reduced pressure of 760 torr or 100 torr or less, and may be carried out step by step with different temperatures and pressures. The reaction can be carried out for 10 minutes or more, for example 15 minutes to 24 hours.
In embodiments, the reaction may be carried out in the presence of a catalyst. The catalyst may be an alkali metal catalyst, an alkaline earth metal catalyst, or the like. Examples of the alkali metal catalyst include, but are not limited to, LiOH, NaOH, and KOH. These may be used alone or in combination of two or more. The amount of the catalyst to be used may be 0.0001 to 0.01 mole based on 100 moles of the polycarbonate resin, but is not limited thereto. Sufficient reactivity can be obtained in the above range.
In an embodiment, the polycarbonate resin may have a weight average molecular weight measured by gel permeation chromatography (GPC) of 10,000 to 200,000 g / mol, for example, 12,000 to 150,000 g / mol. In the above range, the polycarbonate resin may have excellent weather resistance, workability, impact resistance, physical properties and the like.
In the specific examples, the polycarbonate resin may have a yellow index difference (DELTA YI) of 12 or less, for example, 0.1 to 11 before and after ultraviolet (UV) irradiation, In the above range, the polycarbonate resin may have excellent weather resistance.
[Formula 1]
Yellow index difference (ΔYI) = YI 1 - YI 0
YI 0 is the yellow index of the 2.5 mm thick specimen measured according to ASTM D1925 and YI 1 is the ultraviolet ray (UV) of the specimen at 313 nm and 0.63 W / m 2 at 60 ° C for 24 hours And then measured according to ASTM D1925.
In an embodiment, the polycarbonate-based resin may have a glass transition temperature of 120 to 170 占 폚, for example, 130 to 150 占 폚. Within the above range, the polycarbonate resin can have excellent processability and heat resistance.
In an embodiment, the polycarbonate-based resin has an Izod impact strength of 70 to 100 kgf · cm / cm, for example, 75 to 95 kgf · cm / cm at a room temperature according to ASTM D256 The impact resistance and the like of the polycarbonate resin in the above range can be excellent.
The molded article according to the present invention may be formed from a resin composition containing the polycarbonate-based resin. Since the polycarbonate resin is excellent in weather resistance, workability and impact resistance, the polycarbonate resin can be used alone without any other additive. However, as long as it does not impair the effect of the present invention, Can be further added. Examples of the additives include, but are not limited to, fillers, reinforcing agents, stabilizers, colorants, antioxidants, antistatic agents, flow improvers, release agents, and nucleating agents. When the additive is used, the content thereof may be 25 parts by weight or less, for example, 10 parts by weight or less, based on 100 parts by weight of the polycarbonate resin, but not limited thereto.
In a specific example, the resin composition containing the polycarbonate resin may be prepared by using the polycarbonate resin alone or, if necessary, other additives, etc., by a conventional method, and then melt-extruded using a twin-screw extruder or the like, . ≪ / RTI > The produced pellets can be made into various molded articles through known molding methods such as injection molding, extrusion molding, vacuum molding, cast molding and the like.
The molded article of the present invention can be applied to various fields to which the thermoplastic resin composition is applied, and includes a polycarbonate resin excellent in weather resistance, impact resistance and the like, and thus is useful as an outdoor material or the like requiring such properties.
Hereinafter, the configuration and operation of the present invention will be described in more detail with reference to preferred embodiments of the present invention. It is to be understood, however, that the same is by way of illustration and example only and is not to be construed in a limiting sense.
The contents not described here are sufficiently technically inferior to those skilled in the art, and a description thereof will be omitted.
Example
Manufacturing example 1 to 7: Polycarbonate series Manufacture of resin
(A) a bisphenol A type polycarbonate (PC) resin and (B) bis (2-hydroxyethyl) terephthalate (BHET) were added to the polycarbonate resin (A) To 100 parts by mol of KOH, 0.001 part by mol of KOH was added to the reactor, and then nitrogen was used to remove oxygen in the reactor. Next, the temperature of the reactor was raised to 290 DEG C, held at a pressure of 760 torr for 1 hour, lowered to 100 torr and maintained for 2 hours to prepare a molten polycarbonate resin. Using 1 H-NMR, it was confirmed that the produced polycarbonate resin contained repeating units represented by the following formulas (1a), (1b), (1c) and (1d) 1d: 25 molar parts), a weight average molecular weight (Mw) and a glass transition temperature (Tg) were measured, and the results are shown in Table 1 below.
[Formula 1a]
[Chemical Formula 1b]
[Chemical Formula 1c]
≪ RTI ID = 0.0 &
Property evaluation method
(1) Weight average molecular weight (unit: g / mol): Measured using gel permeation chromatography (GPC).
(2) Glass transition temperature (unit: 占 폚): Measured using a differential scanning calorimeter (DSC). A DSC Q20 measuring instrument was used, and 5 to 10 mg of a sample was vacuum-dried at 80 DEG C for 4 hours (moisture of 3,000 ppm or less), and then heated at 30 DEG C to 300 DEG C at a rate of 10 DEG C / min in a nitrogen atmosphere , The temperature was maintained at 300 ° C for 1 minute, the temperature was further reduced from 300 ° C to 30 ° C at a rate of 10 ° C / min, the temperature was maintained at 30 ° C for 1 minute, The resulting transition temperature was measured.
It can be seen from the results of Table 1 that the polycarbonate resin of the present invention has a glass transition temperature of 142 to 148 DEG C even though the weight average molecular weight is 14,000 to 34,000 g / mol, and the conventional polyester resin having the weight average molecular weight in the same range (Manufactured from bisphenol A and terephthaloyl chloride, Tg: about 200 ° C), it is possible to process at a low temperature and it is possible to reduce deterioration of physical properties due to high temperature.
Example 1 to 7 and Comparative Example 1-2
(A1), (A2), (A3), (A3), and (A3) prepared in Production Examples 1, 2, 3, 4, 5, 6 and 7, (B) a bisphenol A type polycarbonate resin having a weight average molecular weight of 22,000 g / mol and (C) a UV stabilizer (Tinuvin 329 from BASF) Extruded at a temperature of 270 占 폚 in a twin-screw extruder having L / D = 36 and? = 32, and pelletized using a pelletizer. The pellets were dried in an oven at 120 ° C. for 4 hours and injection molded at an extruder (manufactured by Dongshin Hydraulic Co., Ltd., DHC 120WD) at a molding temperature of 290 ° C. and a mold temperature of 70 ° C. to prepare specimens. The properties of the prepared specimens were measured by the following methods, and the results are shown in Table 2 below.
Property evaluation method
(1) Weatherability: The yellow index difference (? YI) before and after UV irradiation was calculated according to the following formula (1). The smaller the yellow index difference, the better the weatherability.
[Formula 1]
Difference in yellow index before and after ultraviolet irradiation (ΔYI) = YI 1 - YI 0
YI 0 is the yellow index of a 2.5 mm thick specimen measured according to ASTM D1925 and YI 1 is the ultraviolet ray (UV) condition of the specimen at 313 nm and 0.63 W / m 2 at 60 ° C for 48 hours And then measured according to ASTM D1925.
(2) High temperature discoloration resistance: The yellow index difference (? YI) before and after injection stay was calculated according to the following formula (2). The lower the yellow index difference, the better the discoloration at high temperatures.
[Formula 2]
Difference in yellow index before and after injection stay (ΔYI) = YI b - YI a
In the above formula (2), YI a stands for 3 minutes in the extruder cylinder (extruder manufactured by Dongshin Hydraulic Co., Ltd. under the designation DHC 120WD) measured at ASTM D1925 under conditions of a molding temperature of 320 캜 and a mold temperature of 70 캜 YI b is the yellow index of the 2.5 mm thick specimen obtained by injection molding the pellet in the injector cylinder for 30 minutes.
(3) Impact resistance (unit: kgf cm / cm): The notched Izod impact strength of 1/8 "thick specimen was measured at room temperature (25 ° C) according to the evaluation method specified in ASTM D256.
(Parts by weight)
From the results shown in Table 2, it can be seen that the polycarbonate resins of the present invention (Examples 1 to 7) are excellent in both weather resistance, high temperature discoloration resistance and impact resistance.
On the other hand, in the case of the usual polycarbonate resin (Comparative Example 1), it was found that the weather resistance was lowered. When the ultraviolet stabilizer was used for the polycarbonate resin (Comparative Example 2), the weather resistance was good, It can be seen that yellowing may occur during molding.
It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (11)
A polycarbonate resin comprising a repeating unit represented by the following formula (2):
[Chemical Formula 1]
R 1 and R 2 are independently an alkyl group having 1 to 10 carbon atoms or a halogen atom, A is a single bond, a hydrocarbon group having 1 to 12 carbon atoms, -CO-, -O-, -S- or -SO 2 -, a and b are each independently an integer of 0 to 4 and the average value of n is 5 to 200;
(2)
In Formula 2, R 3 , R 4 , R 5, and R 6 are each independently a hydrogen atom or a methyl group, Ar is an arylene group having 6 to 12 carbon atoms, m has an average value of 0 to 2, The average value is independently 0 to 1.
[Formula 1]
Yellow index difference (ΔYI) = YI 1 - YI 0
YI 0 is the yellow index of the 2.5 mm thick specimen measured according to ASTM D1925 and YI 1 is the ultraviolet ray (UV) of the specimen at 313 nm and 0.63 W / m 2 at 60 ° C for 24 hours And then measured according to ASTM D1925.
[Chemical Formula 1]
(2)
(3)
[Chemical Formula 4]
Wherein R 1 and R 2 are each independently an alkyl group having 1 to 10 carbon atoms or a halogen atom and R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom or a methyl group A is a single bond, a hydrocarbon group having 1 to 12 carbon atoms, -CO-, -O-, -S- or -SO 2 -, Ar is an arylene group having 6 to 12 carbon atoms, a and b are independently , The average value of n is 5 to 200, the average value of m is 0 to 2, and the average values of p and q are independently 0 to 1.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6143839A (en) | 1998-09-14 | 2000-11-07 | General Electric Company | Weatherable blends of polycarbonates with arylate polymers |
| KR100709878B1 (en) | 2005-12-30 | 2007-04-20 | 제일모직주식회사 | Polycarbonate/polyester alloy resin composition having excellent impact-resistance, flowability and articles using the same |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6143839A (en) | 1998-09-14 | 2000-11-07 | General Electric Company | Weatherable blends of polycarbonates with arylate polymers |
| KR100709878B1 (en) | 2005-12-30 | 2007-04-20 | 제일모직주식회사 | Polycarbonate/polyester alloy resin composition having excellent impact-resistance, flowability and articles using the same |
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