Flame-retardant compound, flame-retardant particle, resin composition and resin formed body

Abstract

A flame-retardant compound has a structure represented by formula (1): —X-A 1 (-O—CO—O—Ar 1 ) m   (1) wherein A 1 represents a substituted or unsubstituted aromatic group, X represents a divalent group represented —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —; Ar 1 represents a substituted or substituted phenyl group; and m represents an integer of 1 to 3.

1 . A flame-retardant compound that has a structure represented by formula (1):
   —X-A 1 (-O—CO—O—Ar 1 ) m    (1)   wherein A 1  represents a substituted or unsubstituted aromatic group;   X represents a divalent group represented by —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —;   Ar 1  represents a substituted or unsubstituted phenyl group; and   m represents an integer of 1 to 3.   
   
   
       2 . The flame-retardant compound according to  claim 1 ,
 wherein A 1  represents an aromatic group having at least one substituent selected from the group consisting of an alkyl group having a carbon number of 1 to 10, a phenyl group, an alkoxyl group, an amino group, an amido group, an aryl group, an acyl group, a vinyl group, an allyl group, a hydroxy group, an ester group and a carboxyl group.   
   
   
       3 . The flame-retardant compound according to  claim 1 ,
 wherein X represents a divalent group selected from the group consisting of —S—, —CN—, —SO— and —SO 2 —.   
   
   
       4 . The flame-retardant compound according to  claim 1 ,
 wherein Ar 1  represents a phenyl group having at least one substituent selected from the group consisting of an alkyl group having a carbon number of 1 to 10, a phenyl group, an alkoxyl group, an amino group, an amido group, an aryl group, an acyl group, a vinyl group, an allyl group, a hydroxy group, an ester group and a carboxyl group.   
   
   
       5 . The flame-retardant compound according to  claim 1  that has a structure represented by formula (2):
   (Ar 2 —O—CO—O-) n A 2 -X-A 1 (—OCO—O—Ar 1 ) m    (2)   wherein A 1  and A 2  each independently represents a substituted or unsubstituted aromatic group;   X represents a divalent group represented by —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —;   Ar 1  and Ar 2  each independently represents a substituted or unsubstituted phenyl group; and   m and n each independently represents an integer of 1 to 3.   
   
   
       6 . The flame-retardant compound according to  claim 5 ,
 wherein A 1  and A 2  each independently represents an aromatic group having at least one substituent selected from the group consisting of an alkyl group having a carbon number of 1 to 10, a phenyl group, an alkoxyl group, an amino group, an amido group, an aryl group, an acyl group, a vinyl group, an allyl group, a hydroxy group, an ester group and a carboxyl group.   
   
   
       7 . The flame-retardant compound according to  claim 5 ,
 wherein Ar 1  and Ar 2  each independently represents a phenyl group having at least one substituent selected from the group consisting at an alkyl group having a carbon number of 1 to 10, a phenyl group, an alkoxyl group, an amino group, an amido group, an aryl group, an acyl group, a vinyl group, an allyl group, a hydroxy group, an ester group and a carboxyl group.   
   
   
       8 . A flame-retardant particle that has a structure represented by formula (1) introduced into a surface thereof:
   —X-A 1 (-O—CO—O—Ar 1 )   (1)   wherein A 1  represents a substituted or unsubstituted aromatic group;   X represents a divalent group represented by —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —;   Ar 1  represents a substituted or unsubstituted phenyl group, and   m represents an integer of 1 to 3.   
   
   
       9 . The flame-retardant particle according to  claim 8 , comprising:
 a core particle containing at least one selected from the group consisting of an inorganic material, an inorganic material complex, an organic polymer, a dendrimer, clay, fullerene or carbon nanotube.   
   
   
       10 . The flame-retardant particle according to  claim 9 ,
 wherein the core particle has at least one functional group selected from the group consisting of a hydroxyl group, a carboxyl group, an amino group, an aldehyde group, a vinyl group, a carbonyl group, a nitro group, a sulfo group, an ether group, an ester group, an amide group, an isocyanate group, a halogen group, an alkyl group and a cyano group on a surface thereof.   
   
   
       11 . The flame-retardant particle according to  claim 8 , which has a volume average particle diameter of from 500 nm to 5 μm. 
   
   
       12 . The flame-retardant particle according to  claim 8 , comprising:
 a surface coat layer on the core particle, the surface coat layer containing the structure represented by formula (1).   
   
   
       13 . The flame-retardant particle according to  claim 12 ,
 wherein a coverage of the surface coat layer is 5 mass % or more of the entire flame-retardant particle.   
   
   
       14 . The flame-retardant particle according to  claim 12 ,
 wherein the core particle is a porous particle, and   pores of the porous particle are filled with a constituent material of the surface coat layer.   
   
   
       15 . The flame-retardant particle according to  claim 12 , further comprising:
 a layer other than the surface coat layer on the core particle.   
   
   
       16 . A resin composition, comprising:
 a resin; and   at least one of:   a flame-retardant compound that has a structure represented by formula (1):
   —X-A 1 (-O—CO—O—Ar 1 ) m    (1) 
   wherein A 1  represents a substituted or unsubstituted aromatic group;   X represents a divalent group represented by —S—, —O—, —CO—, —CN—, -CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —;   Ar 1  represents a substituted or unsubstituted phenyl group; and   m represents an integer of 1 to 3; and   
     a flame-retardant particle that has a structure represented by formula (1) introduced into a surface thereof:
   —X-A 1 (-O—CO—O—Ar 1 ) m    (1) 
 wherein A 1  represents a substituted or unsubstituted aromatic group; 
 X represents a divalent group represented by —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —; 
 Ar 1  represents a substituted or unsubstituted phenyl group; and 
 m represents an integer of 1 to 3. 
 
   
   
       17 . The resin composition according to  claim 16 ,
 wherein a total content of the at least one of the flame-retardant compound and the flame-retardant particle is from 1 to 100 parts by mass, per 100 parts by mass of the resin.   
   
   
       18 . The resin composition according to  claim 16 , further comprising:
 a flame retarder other than the at least one of the flame-retardant compound and the flame-retardant particle.   
   
   
       19 . The resin composition according to  claim 18 ,
 wherein the flame retarder is at least one selected from the group consisting of a phosphorus-based flame retarder, a bromine-based flame retarder, a silicone-based flame retarder and an inorganic particle-based flame retarder.   
   
   
       20 . The resin composition according to  claim 18 ,
 wherein a total content of the flame retarder is 10 mass % or less based on an entire solid content of the resin composition.   
   
   
       21 . A resin formed body, comprising:
 a resin; and   at least one of:   a flame-retardant compound that has a structure represented by formula (1):
   —X-A 1 (-O—CO— 0 —Ar 1 ) m    (1) 
   wherein A 1  represents a substituted or unsubstituted aromatic group;   X represents a divalent group represented by —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —;   Ar 1  represents a substituted or unsubstituted phenyl group; and   m represents an integer of 1 to 3; and   
     a flame-retardant particle that has a structure represented by formula (1) introduced into a surface thereof:
   —X-A 1 (-O—CO—O—Ar 1 ) m    (1) 
 wherein A 1  represents a substituted or unsubstituted aromatic group; 
 X represents a divalent group represented by —S—, —O—, —CO—, —CN—, —CH 2 —, —C(CH 3 ) 2 —, —CH(CH 3 )—, —NH—, —SO— or —SO 2 —; 
 Ar 1  represents a substituted or unsubstituted phenyl group; and 
 m represents an integer of 1 to 3. 
 
   
   
       22 . The resin formed body according to  claim 21 ,
 wherein a total content of the at least one of the flame-retardant compound and the flame-retardant particle is from 1 to 100 parts by mass, per 100 parts by mass of the resin.   
   
   
       23 . The resin formed body according to  claim 21 , further comprising:
 a flame retarder other than the at least one of the flame-retardant compound and the flame-retardant particle.   
   
   
       24 . The resin formed body according to  claim 23 ,
 wherein the flame retarder is at least one selected from the group consisting of a phosphorus-based flame retarder, a bromine-based flame retarder, a silicone-based flame retarder and an inorganic particle-based flame retarder.   
   
   
       25 . The resin formed body according to  claim 23 ,
 wherein a total content of the flame retarder is 10 mass % or less based on an entire solid content of the resin formed body.