Flame retardant and polymer composition using the same
A flame retardant suitable for manufacturing a polymer composition is provided. The polymer composition is used for forming a cured film in which a balance among flame retardancy, adhesion, chemical resistance, heat resistance, and elasticity, and so on, is provided. A flame-retardant polymer composition with an excellent balance among the above properties is also provided. The flame retardant of the invention has a structure of Formula (1), (2), or (3): (in which, R 1 is hydrogen or methyl, R 2 is C2-20 alkylene or C2-20 alkylene in which any —CH 2 — is replaced by —O—, R 3 and R 4 are C1-20 alkyl, phenyl, and phenyl substituted by C1-5 alkyl or phenyl, R 3 and R 4 may also be an integrally-formed cyclic group, and p and q are 0 or 1).
1. A compound of Formula (1), (2), or (3),
wherein R 1 is hydrogen or methyl, R 2 is C2-20 alkylene R 3 and R 4 are independently C1-20 alkyl, phenyl, phenyl with at least one hydrogen replaced by C1-5 alkyl, or phenyl with at least one hydrogen replaced by phenyl, R 3 and R 4 are also an integrally-formed cyclic group, and p and q are independently 0 or 1.
2. A compound of Formula (4), (5), or (6),
wherein R 1 is hydrogen or methyl, and R 2 is C2-20 alkylene or C2-20 alkylene with at least one —CH 2 — being replaced by —O—.
3. A thermosetting composition, comprising: a flame retardant (A) selected from the compound according to claim 1 , and a compound (B) with two or more oxirane rings or oxetane rings.
4. A thermosetting composition, comprising: a flame retardant (A) selected from the compound according to claim 2 , and a compound (B) with two or more oxirane rings or oxetane rings.
5. A thermosetting inkjet ink, comprising: a flame retardant (A) selected from the compound according to claim 1 , and a compound (B) with two or more oxirane rings or oxetane rings.
6. A thermosetting inkjet ink, comprising: a flame retardant (A) selected from the compound according to claim 2 , and a compound (B) with two or more oxirane rings or oxetane rings.
7. A photo-curable composition, comprising: a flame retardant (A) selected from the compound according to claim 1 , multi-functional (meth)acrylate (C), and a photo-polymerization initiator (D).
8. A photo-curable composition, comprising: a flame retardant (A) selected from the compound according to claim 2 , multi-functional (meth)acrylate (C), and a photo-polymerization initiator (D).
9. A photo-curable inkjet ink, comprising: a flame retardant (A) selected from the compound according to claim 1 , multi-functional (meth)acrylate (C), and a photo-polymerization initiator (D).
10. A photo-curable inkjet ink, comprising: a flame retardant (A) selected from the compound according to claim 2 , multi-functional (meth)acrylate (C), and a photo-polymerization initiator (D).
11. The thermosetting composition according to claim 3 , wherein the compound (B) with two or more oxirane rings or oxetanes rings is a compound of Formula (7), (8), (9), or (10),
wherein in Formula (7), n is an integer of 0-10.
12. The thermosetting composition according to claim 4 , wherein the compound (B) with two or more oxirane rings or oxetane rings is a compound of Formula (7), (8), (9), or (10),
wherein in Formula (7), n is an integer of 0-10.
13. The photo-curable composition according to claim 7 , wherein the multi-functional (meth)acrylate (C) is a compound of Formula (11),
wherein in Formula (11), a number “r” of R 5 among the six R 5 -groups are groups of Formula (11-1), a number “s” of R 5 among the six R 5 -groups are groups of Formula (11-2), r is an integer of 1-5, s is an integer of 1-5, r+s is 6, and R 1 is hydrogen or methyl.
14. The photo-curable composition according to claim 8 , wherein the multi-functional (meth)acrylate (C) is a compound of Formula (11),
wherein in Formula (11), a number “r” of R 5 among the six R 5 -groups are groups of Formula (11-1), a number “s” of R 5 among the six R 5 -groups are groups of Formula (11-2), r is an integer of 1-5, s is an integer of 1-5, r+s is 6, and R 1 is hydrogen or methyl.
15. The photo-curable composition according to claims 7 , wherein the photo-polymerization initiator (D) is bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide or 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide.
16. The photo-curable composition according to claims 8 , wherein the photo-polymerization initiator (D) is bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide or 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide.
17. The thermosetting composition according to claims 3 , further comprising monofunctional (meth)acrylate (E).
18. The thermosetting composition according to claims 4 , further comprising monofunctional (meth)acrylate (E).
19. The thermosetting composition according to claim 17 , wherein the monofunctional (meth)acrylate (E) is a compound of Formula (12),
wherein, R 6 is C2-12 alkylene which may have a ring structure, R 1 is hydrogen or methyl, and t is an integer of 1-30.
20. The thermosetting composition according to claim 18 , wherein the monofunctional (meth)acrylate (E) is a compound of Formula (12),
wherein, R 6 is C2-12 alkylene which may have a ring structure, R 1 is hydrogen or methyl, and t is an integer of 1-30.
21. The thermosetting composition according to claim 19 , wherein the monofunctional (meth)acrylate (E) is at least one of 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, and a combination thereof.
22. The thermosetting composition according to claim 20 , wherein the monofunctional (meth)acrylate (E) is at least one of 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, and a combination thereof.
23. The photo-curable inkjet ink according to claim 9 , wherein the flame retardant (A) is at least one of the compound of Formula (4) with R 2 as C3-5 alkylene, the compound of Formula (5) with R 2 as ethylene, and the compound of Formula (6) with R 2 as propylene; the multi-functional (meth)acrylate (C) is the compound of Formula (11); the photo-polymerization initiator (D) is any one of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide or 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide; and the monofunctional (meth)acrylate (E) is 4-hydroxybutyl (meth)acrylate,
wherein in Formulae (4), (5) and (6), R 1 is hydrogen or methyl, and R 2 is C2-20 alkylene or C2-20 alkylene with at least one —CH 2 — being replaced by —O—; and in Formula (11), a number “r” of R 5 among the six R 5 -groups are groups of Formula (11-1), a number “s” of R 5 among the six R 5 -groups are groups of Formula (11-2), r is an integer of 1-5, s is an integer of 1-5, and r+s is 6.
24. The photo-curable inkjet ink according to claim 10 , wherein the flame retardant (A) is at least one of the compound of Formula (4) with R 2 as C3-5 alkylene, the compound of Formula (5) with R 2 as ethylene, and the compound of Formula (6) with R 2 as propylene; the multi-functional (meth)acrylate (C) is the compound of Formula (11); the photo-polymerization initiator (D) is any one of bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide or 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide; and the monofunctional (meth)acrylate (E) is 4-hydroxybutyl (meth)acrylate,
wherein in Formula (11), a number “r” of R 5 among the six R 5 -groups are groups of Formula (11-1), a number “s” of R 5 among the six R 5 -groups are groups of Formula (11-2), r is an integer of 1-5, s is an integer of 1-5, r+s is 6, and R 1 is hydrogen or methyl.
25. The thermosetting composition according to claim 3 , comprising no solvent with a boiling point of 300° C. or less under a normal pressure, or comprising a solvent with a boiling point of 300° C. or less under a normal pressure at a ratio of 10 wt % or less based on a total weight of the composition.
26. The thermosetting composition according to claim 4 , comprising no solvent with a boiling point of 300° C. or less under a normal pressure, or comprising a solvent with a boiling point of 300° C. or less under a normal pressure at a ratio of 10 wt % or less based on a total weight of the composition.
27. An electronic circuit board, using the thermosetting composition according to claims 3 to form a flame-retardant cured film on a substrate.
28. An electronic circuit board, using the thermosetting composition according to claims 4 to form a flame-retardant cured film on a substrate.
29. An electronic component, provided with the electronic circuit board according to claim 27 .
30. An electronic component, provided with the electronic circuit board according to claim 28 .
31. A display device, provided with the electronic component according to 29 .
32. A display device, provided with the electronic component according to 30 .