Polyhydric phenol resin, glycidyl ether of polyhydric phenol resin, and uses thereof

Patent metadata

Field	Value
Publication number	US-11629216-B2
Application number	US-202217577517-A
Country	US
Kind code	B2
Filing date	Jan 18, 2022
Priority date	Mar 29, 2021
Publication date	Apr 18, 2023
Grant date	Apr 18, 2023

Abstract

A polyhydric phenol resin is provided. The polyhydric phenol resin comprises a polyhydric phenol resin component and a first component. When the polyhydric phenol resin is characterized in a high-performance liquid chromatography (HPLC), the first component is eluted at a retention time ranging from 27.1 minutes to 28.0 minutes, and based on the total area of the chromatographic peaks of the polyhydric phenol resin, the area percentage of the chromatographic peak of the first component at the corresponding retention time in the spectrum ranges from 1.0% to 20%.

First claim

What is claimed is:

1. A polyhydric phenol resin, which comprises a polyhydric phenol resin component and a first component, wherein when the polyhydric phenol resin is characterized by high-performance liquid chromatography (HPLC), the first component is eluted at a retention time ranging from 27.1 minutes to 28.0 minutes, and based on the total area of the chromatographic peaks of the polyhydric phenol resin, the area percentage of the chromatographic peak of the first component at the corresponding retention time in the spectrum ranges from 1.0% to 20.0%,
wherein the HPLC analysis is performed under the following conditions: a detector applying 254 nm wavelength ultraviolet light; an octadecylsilane (ODS) column which is 250 mm in length and 4.6 mm in inner diameter and has fillers with a particle size of 5 μm; a column temperature of 40° C.; a detector temperature of 35° C.; a mobile phase flow rate of 1.0 mL/min; a sample which is formulated with acetonitrile (ACN) as a solvent and has a sample concentration of 0.5 wt % in ACN; an injection amount of 15 μL; and a composition of mobile phase as follows: from 0 minutes to the 10 th minute of the washing time, the mobile phase is a mixture of 40 vol % of water and 60 vol % of acetonitrile; from the 10 th minute to the 30 th minute of the washing time, the mobile phase changes from a mixture of 40 vol % of water and 60 vol % of acetonitrile to 100 vol % of acetonitrile in a linear gradient manner with respect to time, and from the 30 th minute to the 50 th minute of the washing time, the mobile phase is 100 vol % of acetonitrile,
wherein when the polyhydric phenol resin is characterized by gas chromatography-mass spectrometry (GC-MS), the first component is eluted at a retention time ranging from 18.000 minutes to 21.000 minutes, and a fragmentation pattern of the first component comprises one or more signals at a mass-to-charge ratio (m/z) selected from the group consisting of 51, 65, 77, 89, 91, 115, 130, 165, 178, 193, and 208.

2. The polyhydric phenol resin of claim 1 , wherein when the polyhydric phenol resin is characterized by carbon-13 nuclear magnetic resonance ( 13 C-NMR), the “C-NMR spectrum of the polyhydric phenol resin has an integral value A of signals from 145 ppm to 160 ppm and an integral value B of signals from 28 ppm to 38 ppm, and the ratio of A to B (A/B) ranges from 0.5 to 3.0, wherein the solvent used in the 13 C-NMR is dimethyl sulfoxide, and the reference substance used in the 13 C-NMR is tetramethylsilane.

3. The polyhydric phenol resin of claim 1 , wherein the polyhydric phenol resin is styrenated polyhydric phenol resin.

4. The polyhydric phenol resin of claim 1 , wherein the polyhydric phenol resin has a hydroxyl equivalent weight ranging from 150 g/eq to 320 g/eq.

5. The polyhydric phenol resin of claim 1 , wherein the softening point temperature of the polyhydric phenol resin ranges from 30° C. to 70° C., wherein the softening point temperature is measured in accordance with JIS K 2207 ring and ball method.

6. A glycidyl ether of polyhydric phenol resin, which comprises a component of glycidyl ether of polyhydric phenol resin and a first component, wherein:
when the glycidyl ether of polyhydric phenol resin is characterized by high-performance liquid chromatography (HPLC), the first component is eluted at a retention time ranging from 27.1 minutes to 28.0 minutes, and based on the total area of the chromatographic peaks of the glycidyl ether of polyhydric phenol resin, the area percentage of the chromatographic peak of the first component at the corresponding retention time in the spectrum ranges from 1.0% to 20.0%,
wherein the HPLC analysis is performed under the following conditions: a detector applying 254 nm wavelength ultraviolet light; an octadecylsilane (ODS) column which is 250 mm in length and 4.6 mm in inner diameter and has fillers with a particle size of 5 μm; a column temperature of 40° C.; a detector temperature of 35° C.; a mobile phase flow rate of 1.0 mL/min; a sample which is formulated with acetonitrile (ACN) as a solvent and has a sample concentration of 0.5 wt % in ACN; an injection amount of 15 μL; and a composition of mobile phase as follows: from 0 minutes to the 10 th minute of the washing time, the mobile phase is a mixture of 40 vol % of water and 60 vol % of acetonitrile; from the 10 th minute to the 30 th minute of the washing time, the mobile phase changes from a mixture of 40 vol % of water and 60 vol % of acetonitrile to 100 vol % of acetonitrile in a linear gradient manner with respect to time, and from the 30 th minute to the 50 th minute of the washing time, the mobile phase is 100 vol % of acetonitrile,
wherein when the glycidyl ether of polyhydric phenol resin is characterized by gas chromatography-mass spectrometry (GC-MS), the first component is eluted at a retention time ranging from 18.000 minutes to 21.000 minutes, and a fragmentation pattern of the first component comprises one or more signals at a mass-to-charge ratio (m/z) selected from the group consisting of 51, 65, 77, 89, 91, 115, 130, 165, 178, 193, and 208.

7. The glycidyl ether of polyhydric phenol resin of claim 6 , wherein when the glycidyl ether of polyhydric phenol resin is characterized by carbon-13 nuclear magnetic resonance ( 13 C-NMR), the 13 C-NMR spectrum of the glycidyl ether of polyhydric phenol resin has an integral value A of signals from 145 ppm to 160 ppm and an integral value B of signals from 28 ppm to 38 ppm, the ratio of A to B (AB) ranges from 0.5 to 3.0, wherein the solvent used in the 13 C-NMR is dimethyl sulfoxide, and the reference substance used in the 13 C-NMR is tetramethylsilane.

8. The glycidyl ether of polyhydric phenol resin of claim 6 , wherein the glycidyl ether of polyhydric phenol resin is glycidyl ether of styrenated polyhydric phenol resin.

9. The glycidyl ether of polyhydric phenol resin of claim 6 , wherein the glycidyl ether of polyhydric phenol resin has an epoxy equivalent weight (EEW) ranging from 200 g/eq to 400 g/eq.

10. The glycidyl ether of polyhydric phenol resin of claim 6 , wherein the glycidyl ether of polyhydric phenol resin comprises 300 ppm or less of hydrolyzable chlorine (HyCl).

11. The glycidyl ether of polyhydric phenol resin of claim 6 , wherein the glycidyl ether of polyhydric phenol resin has a hydroxyl value (HV) ranging from 0.040 eq/100 g to 0.10 eq/100 g.

12. The glycidyl ether of polyhydric phenol resin of claim 6 , wherein the glycidyl ether of polyhydric phenol resin comprises 0.003 meq/g to 0.015 meq/g of a-glycol.

13. A curable composition, which comprises (a1) the glycidyl ether of polyhydric phenol resin of claim 6 , and (b1) a hardener.

14. A copper-clad laminate, which comprises: (a2) a dielectric layer, which comprises a dielectric material obtained by curing the curable composition of claim 13 ; and (b2) a copper foil, which is disposed on the surface of the dielectric layer.

15. A curable composition, which comprises (a1) the glycidyl ether of polyhydric phenol resin of claim 7 , and (b1) a hardener.

16. A copper-clad laminate, which comprises: (a2) a dielectric layer, which comprises a dielectric material obtained by curing the curable composition of claim 15 ; and (b2) a copper foil, which is disposed on the surface of the dielectric layer.

17. A curable composition, which comprises (a1) the glycidyl ether of polyhydric phenol resin of claim 8 , and (b1) a hardener.

18. A copper-clad laminate, which comprises: (a2) a dielectric layer, which comprises a dielectric material obtained by curing the cur

Assignees

• Chang Chun Plastics Co Ltd

Inventors

• Hong Chian Wen
• Chung Sung-Kuang
• Tu An-Pang

Classifications

• B32B2260/046

  Synthetic resin · CPC title

• C08G59/20

  characterised by the epoxy compounds used · CPC title

• C08G8/28

  Chemically modified polycondensates · CPC title

• C08G8/08

  of formaldehyde, e.g. of formaldehyde formed in situ · CPC title

• B32B2307/306

  Resistant to heat · CPC title