Flame-proofing agents
View Patent ↗Compounds of formula (I) or (II), wherein R 1 is C 1 –C 18 alkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups, and the radicals R 2 to R 13 are each independently of the others hydrogen; —NO 2 ; dialkylamino; alkylthio; alkylsulfonyl; halogen; C 1 –C 18 alkyl; C 1 –C 18 alkoxy; C 1 –C 18 alkoxyalkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups, are suitable as flame-proofing agents for thermoplastic or thermosetting polymers
1. A compound of formula I or II
wherein R 1 is C 1 –C 18 alkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups and the radicals R 2 to R 13 are each independently of the other hydrogen; —NO 2 ; dialkylamino; alkylthio; alkylsulfonyl; halogen; C 1 –C 18 alkyl; C 1 –C 18 alkoxy; C 1 –C 18 alkoxyalkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alky groups or C 1 –C 6 alkoxy groups.
2. A compound of formula I or II according to claim 1 , wherein R 1 is C 1 –C 12 alkyl or C 6 –C 10 aryl.
3. A compound of formula I or II according to claim 1 , wherein R 1 is isopropyl, n-pentyl or phenyl.
4. A compound of formula I or II according to claim 1 , wherein the radicals R 2 to R 13 are hydrogen.
5. A compound of formula I or II according to claim 1 , wherein at least two of the radicals R 3 , R 4 , R 7 and R 8 are alkoxy, —NO 2 , dialkylamino, alkylthio, alkylsulfonyl or halogen.
6. A compound of formula I or II according to claim 1 , wherein R 3 and R 8 are alkoxy or dialkylamino.
7. A compound of formula I or II according to claim 1 , wherein none of the radicals R 2 to R 13 is a halogen.
8. A process for the preparation of a compound of formula I or II according to claim 1 , wherein a compound of formula III or IV
wherein R 1 is C 1 –C 18 alkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups and the radicals R 2 to R 13 are each independently of the other hydrogen; —NO 2 ; dialkylamino; alkylthio; alkylsulfonyl; halogen; C 1 –C 18 alkyk; C 1 –C 18 alkoxy; C 1 –C 18 alkoxyalkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups is reacted with formaldehyde.
9. A process according to claim 8 wherein the reaction is carried out in an organic solvent at a temperature of from 40° C. to 160° C.
10. A process according to claim 8 wherein the reaction is carried out in an organic solvent at a temperature of from 60° C. to 100° C.
11. A compound of formula III or IV
wherein R 1 is C 1 –C 18 alkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups and the radicals R 2 to R 13 are each independently of the other hydrogen; —NO 2 ; dialkylamino; alkylthio; alkylsulfonyl; halogen; C 1 –C 18 alkyl; C 1 –C 18 alkoxy; C 1 –C 18 alkoxyalkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups.
12. A composition comprising
(a) an epoxy resin; and
(b) a hardener comprising a compound of formula I, II, III or IV
wherein the compound of formula I or II has at least two active hydrogen atoms and wherein R 1 is C 1 –C 18 alkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups and the radicals R 2 , to R 13 are each independently of the other hydrogen; —NO 2 ; dialkylamino; alkylthio; alkylsulfonyl; halogen; C 1 –C 18 alkyl; C 1 –C 18 alkoxy; C 1 –C 18 alkoxyalkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups.
13. A composition comprising
(a) a thermoplastic or thermosetting resin and
(b) a compound of formula I, II, III or IV
wherein R 1 is C 1 –C 18 alkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups and the radicals R 2 to R 13 are each independently of the other hydrogen: —NO 2 ; dialkylamino; alkylthio; alkylsulfonyl; halogen; C 1 –C 18 alkyl; C 1 –C 18 alkoxy; C 1 –C 18 alkoxyalkyl; C 5 –C 12 cycloalkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; C 5 –C 22 aryl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups; or C 7 –C 30 aralkyl that is unsubstituted or substituted by one or more C 1 –C 6 alkyl groups or C 1 –C 6 alkoxy groups.
14. A composition according to claim 13 , wherein component (b) is present in an amount from 5% to 60% by weight based on the total amount of components (a) and (b).
15. A composition according to claim 13 , wherein component (b) is present in an amount from 10% to 50% by weight based on the total amount of components (a) and (b).
16. A composition according to claim 13 , wherein component (b) is present in an amount from 15% to 40% by weight based on the total amount of components (a) and (b).
17. A composition according to claim 13 wherein component (a) is an epoxy resin or an oxazine resin.
18. A composition according to claim 13 , wherein component (a) is an epoxy resin, component (b) optionally comprises other flame-proofing agents in addition to those recited in claim 13 , and further comprising component (c) a hardener for the epoxy resin.
19. A composition according to claim 18 , wherein the component (b) is present in an amount from 5% to 60% by weight based on the total amount of components (a), (b), and (c).
20. A composition according to claim 18 , wherein the component (b) is present in an amount from 10% to 50% by weight based on the total amount of components (a), (b), and (c).
21. A composition according to claim 18 , wherein the component (b) is present in an amount from 15% to 40% by weight based on the total amount of components (a), (b), and (c).
22. A composition according to claim 18 comprising as component (a) a diglycidyl ether of a bisphenol, an epoxy novolak, a cycloaliphatic epoxy resin or a poly(N-glycidyl) compound.
23. A composition according to claim 18 comprising as component (a) a diglycidyl ether of a bisphenol A, a diglycidyl ether of bisphenol F, an epoxyphenol novolak, an epoxycresol novalak, 3,4-epoxycyclohexylmethyl 3′,4′-epoxycyclohexanecarboxylate or N,N,N′,N′-tetraglycidyldiaminodiphenylmethane.
24. A composition according to claim 18 , wherein the hardener is an anhydride or dicyandiamide.
25. A composition according to claim 18 , wherein the hardener is tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, dicyandiamide, or a novolak.
26. A composition according to claim 18 , wherein the hardener is a compound of formula III or IV.
27. A cured product obtained by curing a composition according to claim 13 .