Processes of synthesizing multi-functional phosphorus-containing epoxy curing agent
A series of curing agents are provided. The curing agents are multi-functional and phosphorus-containing. The curing agents have excellent processability to be used as an epoxy resin curing agent. The curing agents can be cured to obtain a phosphorus-containing epoxy thermoset with flame retardancy characteristic. The epoxy thermosets are very fit for circuit board substrate having high glass transition temperature; semiconductor packaging material; and related materials.
1. A multi-functional phosphorus-containing epoxy curing agent,
wherein said curing agent is selected from a group consisting of a phosphorus compound and a phosphorus mixture;
wherein said curing agent has the following formula (I):
wherein each of R 1 and R 2 is selected from a group consisting of C 1 ˜C 6 alkane, C 3 ˜C 6 alkanecycloalkane group, phenyl group and —CF 3 ;
wherein n is an integer selected from 0 to 10;
wherein each of A and B is selected from a group consisting of —OH and —NH 2 ;
wherein X is a chemical group selected from a group consisting of null,
and
wherein m is an integer selected from 1 to 10.
2. The curing agent according to claim 1 ,
wherein n=1, X is a ether group, R 1 and R 2 are methyl groups, A and B are both —OH and said formula (I) is formula (DMEP 4 ):
3. The curing agent according to claim 2 ,
wherein said formula (DMEP 4 ) is a formula selected from a group consisting of formula (A) and formula (D):
4. The curing agent according to claim 1 ,
wherein n=1, X is a ether group, R 1 and R 2 are methyl groups, A and B are both —NH 2 and said formula (I) is formula (DMEP 4 ).
5. The curing agent according to claim 4 ,
wherein said formula (DMEP 4 ) is a formula selected from a group consisting of formula (A) and formula (D):
6. The curing agent according to claim 1 ,
wherein n=1, X is a ether group, R 1 and R 2 are methyl groups, A and B are separately —OH and —NH 2 and said formula (I) is formula (DMEP 2 A 2 ):
7. The curing agent according to claim 2 ,
wherein said formula (DMEP 4 ) is a formula selected from a group consisting of formula (A) and formula (D):
8. The curing agent according to claim 1 ,
wherein said curing agent has a fabrication method, including obtaining compounds to be reacted with an acid catalyst to obtain said curing agent having said formula (I);
wherein said compounds are organic phosphorous compounds having formula (II), formula (III) and formula (IV):
wherein each of R 1 and R 2 is selected from a group consisting of C 1 ˜C 6 alkane, C 3 ˜C 6 alkanecycloalkane group, phenyl group and —CF 3 ;
wherein n is an integer selected from 0 to 10;
wherein each of A and B is selected from a group consisting of —OH and —NH 2 ;
wherein X is a chemical group selected from a group consisting of null,
and wherein m is an integer selected from 1 to 10.
9. The curing agent according to claim 8 ,
wherein n=1, X is a ether group, R 1 and R 2 are methyl groups, A and B are both —OH and said formula (I), said formula (II), said formula (III) and said formula (IV) are:
10. The curing agent according to claim 9 ,
wherein said formula (II) is 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO), said formula (III) is 4-acetylphenyl ether, said formula (IV) is catechol and said formula (I) is formula (A):
11. The curing agent according to claim 9 ,
wherein said formula (II) is DOPO, said formula (III) is 4-acetylphenyl ether, said formula (IV) is resorcinol and said formula (I) is formula (D):
12. The curing agent according to claim 8 ,
wherein n=1, X is a ether group, R 1 and R 2 are methyl groups, A and B are both —NH 2 and said formula (I), said formula (II), said formula (III) and said formula (IV) are:
13. The curing agent according to claim 12 ,
wherein said formula (II) is DOPO, said formula (III) is 4-acetylphenyl ether, said formula (IV) is o-phenylenediamine and said formula (I) is formula (B):
14. The curing agent according to claim 12 ,
wherein said formula (II) is DOPO, said formula (III) is 4-acetylphenyl ether, said formula (IV) is m-phenylenediamine and said formula (I) is formula (E):
15. The curing agent according to claim 8 ,
wherein n=1, X is a ether group, R 1 and R 2 are methyl groups, A and B are separately —OH and —NH 2 and said formula (I), said formula (II), said formula (III) and said formula (IV) are:
16. The curing agent according to claim 15 ,
wherein said formula (II) is DOPO, said formula (III) is 4-acetylphenyl ether, said formula (IV) is 2-aminophenol and said formula (I) is formula (C):
17. The curing agent according to claim 15 ,
wherein said formula (II) is DOPO, said formula (III) is 4-acetylphenyl ether, said formula (IV) is 3-aminophenol and said formula (I) is formula (F):
18. The curing agent according to claim 8 ,
wherein said acid catalyst is selected from a group consisting of oxalic acid, p-toluenesulfonic acid (pTSA), methanesulfonic acid, trifluoromethane sulfonic acid, sulfuric acid, haloid acid (HX), trifluoroactic Acid (CF 3 COOH), nitric acid (HNO 3 ), and phosphoric acid (H 3 PO 4 ).