Phosphorus compounds, synthesis method thereof, and polycarbonate resin composition including them

Patent metadata

Field	Value
Publication number	US-10538663-B2
Application number	US-201816106180-A
Country	US
Kind code	B2
Filing date	Aug 21, 2018
Priority date	Sep 4, 2017
Publication date	Jan 21, 2020
Grant date	Jan 21, 2020

Abstract

The present disclosure relates to a phosphorus compound represented by the following Chemical Formula 1.

In the above Chemical Formula 1, Ar is aryl and R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently H, substitutable linear or branched C 1 -C 20 alkyl and substitutable C 6 -C 20 aryl, the aryl includes a member selected from the group consisting of phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, pyrene, fluoranthen, chrysene, benzofluoranthen, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophen, dibenzofuran, and combinations thereof, and the substitution is substitution with C 1 -C 6 alkyl or C 6 -C 20 aryl, but may not be limited thereto.

First claim

We claim:

1. A phosphorus compound represented by the following Chemical Formula 1:

(wherein in the above Chemical Formula 1,
Ar is aryl and R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently H, substitutable linear or branched C 1 -C 20 alkyl and substitutable C 6 -C 20 aryl,
the aryl includes a member selected from the group consisting of phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, pyrene, fluoranthen, chrysene, benzofluoranthen, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophen, dibenzofuran, and combinations thereof, and
the substitution is substituted with C 1 -C 6 alkyl or C 6 -C 20 aryl).

2. The phosphorus compound of claim 1 ,
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently H or substitutable linear or branched C 1 -C 20 alkyl, and
the substitution is substituted with C 1 -C 6 alkyl or C 6 -C 20 aryl.

3. The phosphorus compound of claim 1 ,
wherein the phosphorous compound includes the following compound:

4. A synthesis method of a phosphorous compound of claim 1 , comprising:
reacting a compound represented by the following Chemical Formula 2 with a compound represented by the following Chemical Formula 3:

(wherein in the above Chemical Formula 2,
R 1 , R 2 , and R 3 are each independently H, substitutable linear or branched C 1 -C 20 alkyl and substitutable C 6 -C 20 aryl,
the substitution is substituted with C 1 -C 6 alkyl or C 6 -C 20 aryl, and
X includes one or more halogen elements selected from the group consisting of F, Cl, Br, and I); and
HO—Ar—OH  [Chemical Formula 3]

(wherein in the above Chemical Formula 3,
Ar is aryl, and
the aryl includes a member selected from the group consisting of phenyl, biphenyl, naphthalene, fluorene, anthracene, phenanthrene, pyrene, fluoranthen, chrysene, benzofluoranthen, perylene, quinoline, indenoanthracene, indenophenanthrene, hydroanthracene, dibenzothiophen, dibenzofuran, and combinations thereof).

5. The synthesis method of a phosphorous compound of claim 4 ,
wherein the aryl is biphenyl.

6. A polycarbonate resin composition, comprising:
a phosphorous compound of claim 1 ;
a polycarbonate resin; and
a non-halogenated flame retardant.

7. The polycarbonate resin composition of claim 6 ,
wherein the non-halogenated flame retardant includes a phosphate flame retardant.

8. The polycarbonate resin composition of claim 7 ,
wherein the phosphate flame retardant is a flame retardant selected from the group consisting of resorcinol bis(diphenyl phosphate) (RDP), bisphenol A bis(diphenyl phosphate) (BDP), triphenyl phosphate (TPP), aromatic phosphate, aromatic diphosphate, aromatic triphosphate, aromatic polyphosphate, trimethyl phosphate (TMP), triethyl phosphate (TEP), tricresyl phosphate (TCP), trixylenyl phosphate (TXP), and combinations thereof.

9. The polycarbonate resin composition of claim 6 ,
wherein the polycarbonate resin composition contains 0.1 part by weight to 50 parts by weight of the phosphorous compound and 0.1 part by weight to 50 parts by weight of the non-halogenated flame retardant relative to 100 parts by weight of the polycarbonate resin.

10. The polycarbonate resin composition of claim 6 ,
wherein the polycarbonate resin includes a compound represented by the following Chemical Formula 4:

(wherein in the above Chemical Formula 4, n is 50 or more).

11. The polycarbonate resin composition of claim 6 ,
wherein the polycarbonate flame retardant resin composition further includes a material selected from the group consisting of a lubricant, an antioxidant, a photostabilizer, a chain extender, a catalyst, a release agent, a pigment, a dye, an anti-static agent, an antimicrobial agent, a processing aid, a metal deactivator, an anti-burning agent, an inorganic filler, glass fiber, an anti-friction agent, an antiwear agent, a coupling agent, and combinations thereof.

Assignees

• Research & Business Found Sungkyunkwan Univ

Inventors

• Kim Jinhwan
• Kang Soo-Jung
• Hai Vo Thi
• Park Sang-Won

Classifications

• C08L2201/02

  Flame or fire retardant/resistant · CPC title

• C08K5/521

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title

• C07F9/65746

  the molecule containing more than one cyclic phosphorus atom · CPC title

• C08K5/523

  with hydroxyaryl compounds · CPC title

• C07F9/65748 Primary

  the cyclic phosphorus atom belonging to more than one ring system · CPC title