Phosphorus-containing compound, manufacturing method thereof and flame-retardant thermoset

Patent metadata

Field	Value
Publication number	US-11028109-B2
Application number	US-201916417954-A
Country	US
Kind code	B2
Filing date	May 21, 2019
Priority date	May 21, 2018
Publication date	Jun 8, 2021
Grant date	Jun 8, 2021

Abstract

The present disclosure provides a phosphorus-containing compound, which includes a structure represented by formula (I). Formula (I) is defined as in the specification. The present disclosure further provides a flame-retardant thermoset made by the phosphorus-containing compound including the structure represented by formula (I). The present disclosure also provides a manufacturing method for the phosphorus-containing compound.

First claim

What is claimed is:

1. A phosphorus-containing compound, comprising a structure represented by formula (I):

wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, a trifluoromethyl group, an unsubstituted phenyl group, a substituted phenyl group, an unsubstituted naphthyl group or a substituted naphthyl group, wherein R 1 and R 2 are not the hydrogen at the same time, and the hydrogen on the phenyl group of the substituted phenyl group is substituted by a monovalent organic group, the hydrogen on the naphthyl group of the substituted naphthyl group is substituted by a monovalent organic group, and the monovalent organic group is the alkyl group of 1 to 6 carbon atoms, X and Y are each independently —OH or a group represented by formula (MA):

wherein R 3 is the hydrogen atom or the alkyl group of 1 to 6 carbon atoms.

2. The phosphorus-containing compound of claim 1 , wherein the phosphorus-containing compound comprises a structure represented by formula (IA-OH), formula (IB—OH), formula (IC—OH), formula (IA-MMA), formula (IB-MMA) or formula (IC-MMA):

3. A flame-retardant thermoset made by the phosphorus-containing compound of claim 1 , wherein the flame-retardant thermoset is obtained by copolymerizing the phosphorus-containing compound with an unsaturated resin or an epoxy resin.

4. The flame-retardant thermoset of claim 3 , wherein the phosphorus-containing compound comprises a structure represented by formula (I-MA):

wherein R 1 and R 2 are each independently the hydrogen atom, the alkyl group of 1 to 6 carbon atoms, the trifluoromethyl group, the unsubstituted phenyl group, the substituted phenyl group, the unsubstituted naphthyl group or the substituted naphthyl group, wherein R 1 and R 2 are not the hydrogen at the same time, and the hydrogen on the phenyl group of the substituted phenyl group is substituted by a monovalent organic group, the hydrogen on the naphthyl group of the substituted naphthyl group is substituted by a monovalent organic group, and the monovalent organic group is the alkyl group of 1 to 6 carbon atoms, R 3 is the hydrogen atom or the alkyl group of 1 to 6 carbon atoms.

5. A manufacturing method for a phosphorus-containing compound, comprising:
synthesizing a hydroxyl group-containing compound, wherein an organic phosphorus-containing compound represented by formula (i) is reacted with a carbonyl group-containing compound represented by formula (ii) to obtain a hydroxyl group-containing compound represented by formula (iii):

and
performing an acid-catalyzed reaction, wherein the hydroxyl group-containing compound represented by formula (iii) is reacted with benzenediol at a catalysis of an acid catalyst to obtain a phosphorus-containing compound represented by formula (I—OH):

wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, a trifluoromethyl group, an unsubstituted phenyl group, a substituted phenyl group, an unsubstituted naphthyl group or a substituted naphthyl group, wherein R 1 and R 2 are not the hydrogen at the same time, and the hydrogen on the phenyl group of the substituted phenyl group is substituted by a monovalent organic group, the hydrogen on the naphthyl group of the substituted naphthyl group is substituted by a monovalent organic group, and the monovalent organic group is the alkyl group of 1 to 6 carbon atoms.

6. The manufacturing method for the phosphorus-containing compound of claim 5 , further comprising:
performing an acrylic-functionalized reaction, wherein the phosphorus-containing compound represented by formula (I—OH) is reacted with an acrylic anhydride compound represented by formula (iv) to obtain a phosphorus-containing compound represented by formula (I-MA):

wherein R 1 and R 2 are each independently the hydrogen atom, the alkyl group of 1 to 6 carbon atoms, the trifluoromethyl group, the unsubstituted phenyl group, the substituted phenyl group, the unsubstituted naphthyl group or the substituted naphthyl group, wherein R 1 and R 2 are not the hydrogen at the same time, and the hydrogen on the phenyl group of the substituted phenyl group is substituted by the monovalent organic group, the hydrogen on the naphthyl group of the substituted naphthyl group is substituted by the monovalent organic group, and the monovalent organic group is the alkyl group of 1 to 6 carbon atoms, R 3 is the hydrogen atom or the alkyl group of 1 to 6 carbon atoms.

7. The manufacturing method for the phosphorus-containing compound of claim 5 , wherein the acid catalyst is acetic acid, methanesulfonic acid, oxalic acid, sulfuric acid, p-toluenesulfonic acid or a mixture thereof.

8. A manufacturing method for a phosphorus-containing compound, comprising:
performing an acid-catalyzed reaction, wherein an organic phosphorus-containing compound represented by formula (i) and a carbonyl group-containing compound represented by formula (ii) are reacted with benzenediol at a catalysis of an acid catalyst to obtain a phosphorus-containing compound represented by formula (I—OH):

wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group of 1 to 6 carbon atoms, a trifluoromethyl group, an unsubstituted phenyl group, a substituted phenyl group, an unsubstituted naphthyl group or a substituted naphthyl group, wherein R 1 and R 2 are not the hydrogen at the same time, and the hydrogen on the phenyl group of the substituted phenyl group is substituted by a monovalent organic group, the hydrogen on the naphthyl group of the substituted naphthyl group is substituted by a monovalent organic group, and the monovalent organic group is the alkyl group of 1 to 6 carbon atoms.

9. The manufacturing method for the phosphorus-containing compound of claim 8 , further comprising:
performing an acrylic-functionalized reaction, wherein the phosphorus-containing compound represented by formula (I—OH) is reacted with an acrylic anhydride compound represented by formula (iv) to obtain a phosphorus-containing compound represented by formula (I-MA):

wherein R 1 and R 2 are each independently the hydrogen atom, the alkyl group of 1 to 6 carbon atoms, the trifluoromethyl group, the unsubstituted phenyl group, the substituted phenyl group, the unsubstituted naphthyl group or the substituted naphthyl group, wherein R 1 and R 2 are not the hydrogen at the same time, and the hydrogen on the phenyl group of the substituted phenyl group is substituted by the monovalent organic group, the hydrogen on the naphthyl group of the substituted naphthyl group is substituted by the monovalent organic group, and the monovalent organic group is the alkyl group of 1 to 6 carbon atoms, R 3 is the hydrogen atom or the alkyl group of 1 to 6 carbon atoms.

Assignees

• Univ Nat Chung Hsing

Inventors

• Lin Ching-Hsuan
• Lin Yu-Hsiang
• Yang Po-Chun
• Chiang Yi-Ning
• Chen Wen-Chang

Classifications

• C08G59/1488

  containing phosphorus · CPC title

• C07F9/657172 Primary

  the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: [IMAGE cpc-sch-C07F-1008.gif] (X = O, S) · CPC title

• C08G59/1477

  containing nitrogen · CPC title

• C08G59/1494

  followed by a further chemical treatment thereof · CPC title

• C07F9/3282 Primary

  Esters with hydroxyaryl compounds · CPC title