Bioderived biphenyl-containing compounds and their conversion to polymers and macromonomers
US-11174343-B2 · Nov 16, 2021 · US
US9765184B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9765184-B2 |
| Application number | US-201114345459-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 13, 2011 |
| Priority date | Sep 21, 2011 |
| Publication date | Sep 19, 2017 |
| Grant date | Sep 19, 2017 |
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A polycarbonate resin of the present invention is characterized by comprising repeating units represented by Formula 1, Formula 2, Formula 3 and Formula 4, respectively.
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The invention claimed is: 1. A polycarbonate comprising repeating units represented by Formula 1, Formula 2, Formula 3 and Formula 4, respectively: wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, and a and b are each independently an integer from 0 to 4; wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, and a and b are each independently an integer from 0 to 4; wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, R 3 is substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C7 to C20 aralkyl group, a and b are each independently an integer from 0 to 4, and n is 0 or 1; and wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, R 3 is substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C7 to C20 aralkyl group, a and b are each independently an integer from 0 to 4, and n is 0 or 1. 2. A polycarbonate containing about 1˜50 mol % of repeating units of Formula 4 based on the whole repeating units, and having a glass transition temperature of about 130 to about 190° C., a flame retardancy of V-0, as measured on a 3.2 mm thick specimen according to the UL-94, a notched IZOD impact strength of about 25 to about 120 kg·cm/cm, as measured on a ⅛″ thick specimen at room temperature according to ASTM D256, and a transmittance difference (ΔT) of about 12% or less, as calculated by the following Equation 1: wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom; R 3 is substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C7 to C20 aralkyl group, a and b are each independently an integer from 0 to 4, and n is 0 or 1, Δ T = T 0 - T 1 T 0 × 100 [ Equation 1 ] wherein, T 0 is initial visible light transmittance of a 2.5 mm thick sample, and T 1 is visible light transmittance of the sample obtained by immersing the sample in a solution consisting of methyl isobutyl ketone, cyclohexanone and 2-ethoxy ethanol for 2 minutes and then drying the sample at 80° C. for 30 minutes. 3. The polycarbonate as claimed in claim 1 , wherein the polycarbonate comprises repeating units of Formula 1 (M1), Formula 2 (M2), Formula 3 (M3) and Formula 4 (M4) in mole ratio of M1:M2:M3:M4=about 20˜90 mol %:about 5˜50 mol %:about 1˜50 mol %:about 1˜50 mol %: wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, and a and b are each independently an integer from 0 to 4; wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, and a and b are each independently an integer from 0 to 4; wherein, R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, R 3 is substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C7 to C20 aralkyl group, a and b are each independently an integer from 0 to 4, and n is 0 or 1; and wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, R 3 is substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C6 to C12 aryl group, substituted or unsubstituted C7 to C20 aralkyl group, a and b are each independently an integer from 0 to 4, and n is 0 or 1. 4. A method of preparing polycarbonate, comprising transesterifying diols comprising Formula 1-1 and Formula 2-1 with carbonate ester and phosphate ester: wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl group or halogen atom, and a and b are each independently an integer from 0 to 4; and wherein R 1 and R 2 are each independently substituted or unsubstituted C1 to C6 alkyl group, substituted or unsubstituted C3 to C6 cycloalkyl group, substituted or unsubstituted C6 to C12 aryl grou
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