Curable phosphorus-containing compounds and preparation method therefor
AssigneeUFC Corporation
InventorsJen-Hai LIAO, Cheng-Fang CHIANG
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Abstract
Provided are a series of novel curable phosphorus-containing compounds having a bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) structure and the preparation methods thereof. The curable phosphorus-containing compounds can cross-link with other vinyl-containing monomers by the unique design of dual reactive ends thereon, and thus can be used as reactive halogen-free flame retardants. The novel phosphorus-containing compounds are represented by the General Formula (1).
Claims14
A curable phosphorus-containing compound having a bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) structure represented by General Formula (1),
- wherein,
- A1 and A2 are each independently selected from the group consisting of hydrogen atom, hydroxy, cyano, halo, alkoxy, alkyl with a carbon number between 1-8, cycloalkyl with a carbon number between 3-8, aryl, heteroaryl and arylalkyl;
- R1 and R2 are each independently selected from the group consisting of hydrogen atom, alkyl with a carbon number between 1-8, cycloalkyl with a carbon number between 3-8, aryl, heteroaryl and arylalkyl;
- X represents a single bond, (CH2)n, CR3R4, C═O, or SO2, wherein R3 and R4 are respectively selected from the group consisting of hydrogen atom, fluorine atom, fluorine-containing alkyl, alkyl with a carbon number between 1-8, cycloalkyl with a carbon number between 3-8, aryl, heteroalkyl, and arylalkyl, and n is an integer of 1-12;
- each Y independently represents
- wherein * represents a bonding position;
- and
- each Z independently represents
- wherein * represents a bonding position.
A preparation method of a curable phosphorus-containing compound having a bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) structure represented by General Formula (1), comprising:
- (1) performing a nucleophilic addition reaction of bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide) with an aldehyde or ketone compound in the presence of a solvent to obtain a diol intermediate;
- and
- (2) performing an esterification reaction of the diol intermediate with an acylating reagent, and a solvent, and optionally a catalyst or an acid-neutralizing agent,
- wherein the steps (1) and (2) above are represented by the reaction scheme shown below:
- wherein,
- A1 and A2 are each independently selected from the group consisting of hydrogen atom, hydroxy, cyano, halo, alkoxy, alkyl with a carbon number between 1-8, cycloalkyl with a carbon number between 3-8, aryl, heteroaryl and arylalkyl;
- R1 and R2 are each independently selected from the group consisting of hydrogen atom, alkyl with a carbon number between 1-8, cycloalkyl with a carbon number between 3-8, aryl, heteroaryl and arylalkyl;
- X represents a single bond, (CH2)n, CR3R4, C═O, or SO2, wherein R3 and R4 are respectively selected from the group consisting of hydrogen atom, fluorine atom, fluorine-containing alkyl, alkyl with a carbon number between 1-8, cycloalkyl with a carbon number between 3-8, aryl, heteroalkyl, and arylalkyl, n is an integer of 1-12;
- each Y independently represents
- wherein * represents a bonding position;
- each Z independently represents
- wherein * represents a bonding position;
- R5 represents hydrogen atom or methyl;
- and
- R6 represents chlorine atom, acryloxy, or methacryloxy.
Dependencies are inferred from the claim text.