DIOL COMPOUND, POLYCARBONATE, AND PREPARATION METHOD THEREOF

Abstract

Provided are a diol compound which may be used to prepare a polycarbonate having excellent weather resistance, hardness, heat resistance, transparency, impact resistance, etc. while having excellent mechanical properties, a polycarbonate prepared by using the same, and a preparation method thereof.

Claims

1. A diol compound represented by Chemical Formula 1: ##STR00021## wherein, in Chemical Formula 1, X is —O— or —S—, R is C.sub.6-60 arylene unsubstituted or substituted with C.sub.1-10 alkyl, and n is an integer of 1 to 100.

2. The diol compound of claim 1, wherein the diol compound represented by Chemical Formula 1 is one of the compounds represented by Chemical Formula 1-1 to Chemical Formula 1-3: ##STR00022## wherein, in Chemical Formulae 1-1 to 1-3, X, R, and n are the same as defined in Chemical Formula 1.

3. A polycarbonate comprising: a repeating unit derived from a diol compound represented by Chemical Formula 1; a repeating unit derived from a compound represented by Chemical Formula 2; and a carbonate precursor-derived repeating unit: ##STR00023## wherein, in Chemical Formula 1, X is —O— or —S—, R is C.sub.6-60 arylene unsubstituted or substituted with C.sub.1-10 alkyl, and n is an integer of 1 to 100, ##STR00024## wherein, in Chemical Formula 2, R.sub.1 to R.sub.4 are each independently hydrogen, C.sub.1-10 alkyl, C.sub.1-10 alkoxy, or halogen, Z is C.sub.1-10 alkylene unsubstituted or substituted with phenyl, C.sub.3-15 cycloalkylene unsubstituted or substituted with C.sub.1-10 alkyl, O, S, SO, SO.sub.2, or CO.

4. The polycarbonate of claim 3, wherein the diol compound represented by Chemical Formula 1 is one of the compounds represented by Chemical Formula 1-1 to Chemical Formula 1-3: ##STR00025## wherein, in Chemical Formulae 1-1 to 1-3, X, R, and n are the same as defined in Chemical Formula 1.

5. The polycarbonate of claim 3, wherein R.sub.1 to R.sub.4 are each independently hydrogen or C.sub.1-4 alkyl.

6. The polycarbonate of claim 3, wherein a weight ratio of a repeating unit derived from the compound represented by Chemical Formula 1 to a repeating unit derived from the compound represented by Chemical Formula 2 is 5:95 to 50:50.

7. The polycarbonate of claim 3, comprising a repeating unit represented by Chemical Formula 3: ##STR00026## wherein, in Chemical Formula 3, X, R, and n are the same as defined in Chemical Formula 1.

8. The polycarbonate of claim 3, comprising a repeating unit represented by Chemical Formula 4: ##STR00027## wherein, in Chemical Formula 4, R.sub.1 to R.sub.4, and Z are the same as defined in Chemical Formula 2.

9. The polycarbonate of claim 3, wherein pencil hardness of the polycarbonate is B or HB, as measured under a load of 1 kg at an angle of 45 degree in accordance with ASTM D3363.

10. The polycarbonate of claim 3, wherein weather resistance (ΔE value) measured according to Equation 1 is 1 to 11:
ΔE=√{square root over (((L′−L).sup.2+(a′−a).sup.2+(b′−b).sup.2))}  [Equation 1] wherein, in Equation 1, L, a, and b are values of a specimen having a thickness of ⅛ inch, measured in accordance with ASTM D7869 method, and L′, a′ and b′ are values measured again after leaving the corresponding specimen under 2250 hr weather resistance.

11. A method of preparing a polycarbonate, the method comprising a step of: polymerizing a composition including a diol compound represented by Chemical Formula 1, an aromatic diol compound represented by Chemical Formula 2, and a carbonate precursor: ##STR00028## wherein, in Chemical Formula 1, X is —O— or —S—, R is C.sub.6-60 arylene unsubstituted or substituted with C.sub.1-10 alkyl, and n is an integer of 1 to 100, ##STR00029## wherein, in Chemical Formula 2, R.sub.1 to R.sub.4 are each independently hydrogen, C.sub.1-10 alkyl, C.sub.1-10 alkoxy, or halogen, and Z is C.sub.1-10 alkylene unsubstituted or substituted with phenyl, C.sub.3-15 cycloalkylene unsubstituted or substituted with C.sub.1-10 alkyl, O, S, SO, SO.sub.2, or CO.

12. The method of claim 11, wherein the diol compound represented by Chemical Formula 1 is one of the compounds represented by Chemical Formula 1-1 to Chemical Formula 1-3: ##STR00030## wherein, in Chemical Formulae 1-1 to 1-3, X, R, and n are the same as defined in Chemical Formula 1.

13. The method of claim 11, wherein the aromatic diol compound represented by Chemical Formula 2 is one or more compounds selected from the group consisting of bis(4-hydroxyphenyl)methane, bis(4-hydroxyphenyl)ether, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl)sulfoxide, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxyphenyl)ketone, 1,1-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), 2,2-bis(4-hydroxyphenyl)butane, 1,1-bis(4-hydroxyphenyl)cyclohexane (bisphenol Z), 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3-bromophenyl)propane, 2,2-bis(4-hydroxy-3-chlorophenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, and 1,1-bis(4-hydroxyphenyl)-1-phenylethane.

14. A molded article comprising the polycarbonate of claim 3.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0083] FIG. 1 shows a 1H-NMR graph of a compound prepared in Example 1;

[0084] FIG. 2 shows a 1H-NMR graph of a copolycarbonate prepared in Example 1;

[0085] FIG. 3 shows a 1H-NMR graph of a compound prepared in Example 2;

[0086] FIG. 4 shows a 1H-NMR graph of a copolycarbonate prepared in Example 2;

[0087] FIG. 5 shows a 1H-NMR graph of a compound prepared in Example 7;

[0088] FIG. 6 shows a 1H-NMR graph of a copolycarbonate prepared in Example 7;

[0089] FIG. 7 shows a 1H-NMR graph of a compound prepared in Example 8; and

[0090] FIG. 8 shows a 1H-NMR graph of a copolycarbonate prepared in Example 8.

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0091] The present invention will be described in more detail with reference to the following exemplary embodiments. However, the following exemplary embodiments are for illustrative purposes only, and the scope of the present invention is not intended to be limited by the following exemplary embodiments.

EXAMPLE

Example 1

[0092] (1) Preparation of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate

##STR00013##

[0093] Furan-2,5-dicarboxylic acid (8 g) was placed in a 250-mL round bottom flask, dissolved in an MC solvent, and then oxalyl chloride (14.31 g) and DMF (0.3 mL) were added dropwise at room temperature, followed by stirring at room temperature for about 4 hours. When the reaction product became transparent, the solvent was removed using a rotary evaporator to obtain a chlorinated solid compound.

[0094] Thereafter, 4-hydroxybenzoic acid (21.23 g) was placed in a 500-mL round bottom flask, and dissolved in a 2 M NaOH aqueous solution (105 mL). A solution obtained by dissolving the previously obtained solid compound in tetrachloroethane solvent was added dropwise to the reaction flask for 1 hour using a dropping funnel. Thereafter, the mixture was further stirred for about 4 hours, and the reaction was terminated using a hydrochloric acid solution (35%). The resulting white solid was obtained through filtration under reduced pressure and washed with water and methaneol during filtration. The obtained solid was dried overnight in an oven at 60° C., and recrystallized several times with acetone to obtain a white dicarboxylic acid intermediate with a purity of 98%.

[0095] The dicarboxylic acid intermediate (10 g) was placed in a 250-mL round bottom flask, dissolved in an MC solvent, and oxalyl chloride (9.64 g) and DMF (0.2 g) were added dropwise at room temperature, followed by stirring at room temperature for about 4 hours. When the reaction product became transparent, the solvent was removed using a rotary evaporator to obtain a chlorinated solid compound.

[0096] In a separate 250-mL round flask, bisphenol A (11.81 g) was stirred in pyridine (7.98 g) and MC solvent. The previously completed compound without a separate purification process was slowly added to the bisphenol A solution prepared in the flask. After the addition, the reaction was allowed overnight at room temperature. After the reaction was completed, 1N—HCl was used to terminate the reaction, and after washing with Water/MC three times, the residual moisture in the organic layer was removed using MgSO.sub.4, and the organic solvent was removed using a rotary evaporator. A yellow liquid final compound with viscosity (weight average molecular weight: 4,900 g/mol, n=8-9) was obtained in a final yield of 79%.

[0097] .sup.1H-NMR (DMSO-d.sub.6) of the compound is shown in FIG. 1.

[0098] (2) Preparation of Polycarbonate Resin

[0099] 620 g of water, 112.46 g of bisphenol A, 14.09 g of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate prepared in (1), 102.5 g of 40% by weight of NaOH, and 200 ml of MeCl.sub.2 were added to a 2-L main reactor equipped with a nitrogen purge device and a condenser and enabling maintenance at room temperature using a circulator, followed by stirring for several minutes.

[0100] Nitrogen purging was stopped, 62.8 g of triphosgene and 120 ml of MeCl.sub.2 were placed in a 1-L round bottom flask, triphosgene was dissolved therein, and the dissolved triphosgene solution was slowly added to the main reactor. After the addition was completed, 2.7 g of PTBP (p-tert-butylphenol) was added and stirred for 10 min. After stirring was completed, 99.8 g of 40% by weight of a NaOH aqueous solution was added, and 1.5 ml of TEA as a coupling agent was added. At this time, reaction pH was maintained at 11 to 13. After the reaction solution was allowed to stand for a time for sufficient reaction, pH was decreased to 3-4 by addition of HCl to complete the reaction. Then, stirring was stopped, the polymer layer was separated from the aqueous layer, the aqueous layer was removed, and the residue was washed with pure H.sub.2O again, and this process was repeated a total of 3 to 5 times.

[0101] After the washing was completely carried out, only the polymer layer was extracted, and polymer crystals were obtained by re-precipitation using a non-solvent of methanol, H.sub.2O, etc. In this regard, a weight average molecular weight of the prepared polycarbonate was 48,000 g/mol, in terms of PS standard.

[0102] Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 10 wt %, based on the weight of the total repeating units.

[0103] .sup.1H-NMR (CDCl.sub.3-d.sub.1) of the compound is shown in FIG. 2.

Example 2

[0104] (1) Preparation of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate

##STR00014##

[0105] Synthesis was performed in the same manner as in (1) of Examples 1, except that 8.82 g of thiophene-2,5-dicarboxylic acid was used instead of 2,5-Furandicarboxylic acid of Example 1.

[0106] The final compound, bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate (weight average molecular weight: 3,500 g/mol, n=5˜6) was obtained in a final yield of 72%.

[0107] .sup.1H-NMR (DMSO-d.sub.6) of the compound is shown in FIG. 3.

[0108] (2) Preparation of Polycarbonate Resin

[0109] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that 14.03 g of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate prepared in (1) was used instead of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate of Example 1, and 112.55 g of bisphenol-A was used. In this regard, a weight average molecular weight of the prepared polycarbonate was 46,400 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 10 wt %, based on the weight of the total repeating units.

[0110] .sup.1H-NMR (CDCl.sub.3-d.sub.1) of the compound is shown in FIG. 4.

Example 3

[0111] (1) Preparation of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate

##STR00015##

[0112] The same compound as in (1) of Example 1 was used.

[0113] (2) Preparation of Polycarbonate Resin

[0114] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that 6.74 g of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate of Example 1 and 114.55 g of bisphenol-A were used. In this regard, a weight average molecular weight of the prepared polycarbonate was 45,200 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 5 wt %, based on the weight of the total repeating units.

Example 4

[0115] (1) Preparation of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate

##STR00016##

[0116] The same compound as in (1) of Example 2 was used.

[0117] (2) Preparation of Polycarbonate Resin

[0118] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that 6.75 g of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate of Example 2 was used instead of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate and 114.59 g of bisphenol-A was used. In this regard, a weight average molecular weight of the prepared polycarbonate was 47,800 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 5 wt %, based on the weight of the total repeating units.

Example 5

[0119] (1) Preparation of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate

##STR00017##

[0120] The same compound as in (1) of Example 1 was used.

[0121] (2) Preparation of Polycarbonate Resin

[0122] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that 30.43 g of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate of Example 1 and 107.8 g of bisphenol-A were used. In this regard, a weight average molecular weight of the prepared polycarbonate was 49,500 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 20 wt %, based on the weight of the total repeating units.

Example 6

[0123] (1) Preparation of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate

##STR00018##

[0124] The same compound as in (1) of Example 2 was used.

[0125] (2) Preparation of Polycarbonate Resin

[0126] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that 30.44 g of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate of Example 2 was used instead of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate of Example 1 and 107.96 g of bisphenol-A was used. In this regard, a weight average molecular weight of the prepared polycarbonate was 44,100 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 20 wt %, based on the weight of the total repeating units.

Example 7

[0127] (1) Preparation of bis(3-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate

##STR00019##

[0128] Synthesis was performed in the same manner as in (1) of Example 1, except that 3-hydroxybenzoic acid was used in an equal amount, instead of 4-hydroxybenzoic acid of Example 1. The final compound, bis(3-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate (weight average molecular weight: 3,500 g/mol, n=5-6) was obtained in a final yield of 80%.

[0129] .sup.1H-NMR (DMSO-d.sub.6) of the compound is shown in FIG. 5.

[0130] (2) Preparation of Polycarbonate Resin

[0131] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that bis(3-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate prepared in Example 1 was used instead of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate of Example 1. In this regard, a weight average molecular weight of the prepared polycarbonate was 47,200 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 10 wt %, based on the weight of the total repeating units.

[0132] .sup.1H-NMR (CDCl.sub.3-d.sub.1) of the compound is shown in FIG. 6.

Example 8

[0133] (1) Preparation of bis(3-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate

##STR00020##

[0134] Synthesis was performed in the same manner as in (1) of Example 1, except that 3-hydroxybenzoic acid was used in an equal amount, instead of 4-hydroxybenzoic acid of Example 1, and 8.82 g of thiophene-2,5-dicarboxylic acid was used, instead of 2,5-Furandicarboxylic acid. The final compound, bis(3-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate (weight average molecular weight: 4,700 g/mol, n=7-8) was obtained in a final yield of 79%.

[0135] .sup.1H-NMR (DMSO-d.sub.6) of the compound is shown in FIG. 7.

[0136] (2) Preparation of Polycarbonate Resin

[0137] A polycarbonate was prepared in the same manner as in the method of preparing a polycarbonate of Example 1, except that 14.03 g of bis(3-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) thiophene-2,5-dicarboxylate prepared in (1) was used instead of bis(4-((4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)carbonyl)phenyl) furan-2,5-dicarboxylate of Example 1, and 112.55 g of bisphenol-A was used. In this regard, a weight average molecular weight of the prepared polycarbonate was 47,400 g/mol, in terms of PS standard. Further, the results of NMR analysis confirmed that the repeating unit derived from the compound (1) was included in an amount of 10 wt %, based on the weight of the total repeating units.

[0138] .sup.1H-NMR (CDCl.sub.3-d.sub.1) of the compound is shown in FIG. 8.

Comparative Example 1

[0139] 619 g of water, 116.5 g of bisphenol A, 102.5 g of 40% by weight of NaOH, and 195 ml of MeCl.sub.2 were placed in a 2-L main reactor equipped with a nitrogen purge device and a condenser and enabling maintenance at room temperature using a circulator, followed by stirring for several minutes.

[0140] Nitrogen purging was stopped, 62.81 g of triphosgene and 120 ml of MeCl.sub.2 were placed in a 1-L round bottom flask, triphosgene was dissolved therein, and the dissolved triphosgene solution was slowly added to the main reactor containing dissolved BPA. After the addition was completed, 2.7 g of PTBP (p-tert-butylphenol) was added and stirred for 10 min. After stirring was completed, 99.4 g of 40% by weight of a NaOH aqueous solution was added, and 1.04 g of TEA as a coupling agent was added. At this time, reaction pH was maintained at 11 to 13. After the reaction solution was allowed to stand for a time for sufficient reaction, pH was decreased to 3-4 by addition of HCl to complete the reaction. Then, stirring was stopped, the polymer layer was separated from the aqueous layer, the aqueous layer was removed, and the residue was washed with pure H.sub.2O again, and this process was repeated a total of 3 to 5 times.

[0141] After the washing was completely carried out, only the polymer layer was extracted, and polymer crystals were obtained by re-precipitation using a non-solvent of methanol, H.sub.2O, etc. In this regard, a weight average molecular weight of the prepared polycarbonate was 46,000 g/mol, in terms of PS standard.

Experimental Example: Evaluation of Physical Properties of Polycarbonate

[0142] Characteristics of injection specimens of the polycarbonates prepared in Examples and Comparative Examples were measured by the following methods, and the results are shown in Table 1. [0143] Weight average molecular weight (g/mol): 200 mg of the polymer resin was diluted with 200 ml of a tetrahydrofuran (THF) solvent to prepare a sample of about 1000 ppm, of which molecular weight was measured using an Agilent 1200 series GPC system through an RI detector at a flow rate of 1 ml/min. To calculate the molecular weight of the sample, eight PS standards were used to prepare a calibration curve, and based on the curve, the molecular weight of the sample was determined. [0144] Measurement of weather resistance (ΔE): L, a, and b values of a specimen having a thickness of ⅛ inch were measured in accordance with ASTM D7869 method, and the corresponding specimen was left under 2250 hr weather resistance condition in a Weather-Ometer® instrument, and then L′, a′ and b′ values were measured again. Weather resistance ΔE was calculated therefrom according to the following Equation 1.

ΔE=√{square root over (((L′−L).sup.2+(a′−a).sup.2+(b′−b).sup.2))}  [Equation 1] [0145] Measurement of pencil hardness: In accordance with ASTM D3363, pencil was fixed at an angle of 45 degree in a pencil hardness tester, and pencil hardness was measured with pencils of 2B, B, and HB under a load of 1 kg. [0146] Transparency: In accordance with ASTM D1003, transmittance was measured in the range of about 350 nm to 1050 nm using UltraScan PRO (manufactured by HunterLab). [0147] Yellow Index (YI): In accordance with ASTM D1925, YI value was measured at room temperature (20° C.) using a UltraScan PRO (manufactured by HunterLab).

TABLE-US-00001 TABLE 1 Kind of repeating Weight unit of average Chemical molecular Weather Trans- Formula 1/ weight resistance Pencil parency Weight ratio (g/mol) (ΔE) hardness (%) YI Example 1 Chemical 48,000 6.9 B 89.1 2.8 Formula 1-1 (X═O), 10 wt % Example 2 Chemical 46,400 6.9 B 89.2 3.3 Formula 1-1 (X═S), 10 wt % Example 3 Chemical 45,200 7.4 B 89.1 2.6 Formula 1-1 (X═O), 5 wt % Example 4 Chemical 47,800 7.6 B 89.3 2.8 Formula 1-1 (X═S), 5 wt % Example 5 Chemical 49,500 4.7 HB 89.2 3.0 Formula 1-1 (X═O), 20 wt % Example 6 Chemical 44,100 5.2 HB 88.9 3.5 Formula 1-1 (X═S), 20 wt % Example 7 Chemical 47,200 6.3 HB 89.2 3.1 Formula 1-2 (X═O), 10 wt % Example 8 Chemical 47,400 6.6 B 89.0 3.4 Formula 1-2 (X═S), 10 wt % Comparative 100% BPA 46,000 12 2B 89.9 2.0 Example 1 PC

[0148] Referring to Table 1, the polycarbonates of all Examples including the repeating units of the present invention showed the effects of having remarkably improved weather resistance and pencil hardness while having similar transparency and yellow index, as compared with the general BPA polycarbonate of Comparative Example 1.