Flame retardants

Abstract

The invention relates to flame retardants comprising atriazine compound according to Formula 1: (1) with R=phosphite substituted with alkyl, functionalized alkyl, aryl, functionalized aryl, except halogen-substituted alkyl or aryl; R′=alkylene, arylene, alkoxy or aryloxy, all unsubstituted or functionalized, except halogen-substituted; X.sub.1 and X.sub.2=hetero atoms and X.sub.1=X.sub.2 or X.sub.1 not=X.sub.2 and to specific triazine compounds as such. ##STR00001##

Claims

1. A water- or lacquer-based coating for a flammable material comprising 10-30% of a compound according to Formula 1: ##STR00007## with R=phosphite substituted with alkyl, functionalized alkyl, aryl, functionalized aryl, except halogen-substituted alkyl or aryl; R′=alkylene, arylene, alkoxy or aryloxy, all unsubstituted or functionalized, except halogen-substituted; X.sub.1 and X.sub.2=hetero atoms and X.sub.1 and X.sub.2 are the same or different.

2. The coating as claimed in claim 1, wherein R comprises one or more of the following: ##STR00008## wherein Z comprises methyl, ethyl, propyl, butyl, tert-butyl, isobutyl, isopropyl, or phenyl; wherein R′ comprises one or more of the following: ##STR00009## wherein X.sub.1 and X.sub.2 are the same or different and each comprises O or NH.

3. The coating of claim 1 comprising a compound according to Formula 2: ##STR00010##

4. The coating of claim 1, comprising a compound according to Formula 3: ##STR00011##

5. The coating of claim 1, comprising a compound according to Formula 4: ##STR00012##

6. The coating of claim 1, comprising a compound according to Formula 5: ##STR00013##

7. A solid wood or plastic material comprising a compound according to Formula 1: ##STR00014## with R=phosphite substituted with alkyl, functionalized alkyl, aryl, functionalized aryl, except halogen-substituted alkyl or aryl; R′=alkylene, arylene, alkoxy or aryloxy, all unsubstituted or functionalized, except halogen-substituted; X.sub.1 and X.sub.2=hetero atoms and X.sub.1 and X.sub.2 are the same or different.

8. The solid material of claim 7, wherein R comprises one or more of the following: ##STR00015## wherein Z comprises methyl, ethyl, propyl, butyl, tert-butyl, isobutyl, isopropyl, or phenyl; wherein R′ comprises one or more of the following: ##STR00016## wherein X.sub.1 and X.sub.2 are the same or different and each comprises O or NH.

9. The solid material of claim 7, comprising a compound according to Formula 2: ##STR00017##

10. The solid material of claim 7, comprising a compound according to Formula 3: ##STR00018##

11. The solid material of claim 7, comprising a compound according to Formula 4: ##STR00019##

12. The solid material of claim 7, comprising a compound according to Formula 5: ##STR00020##

13. The solid material of claim 7, comprising the compound of Formula 1 at a concentration above 1 wt. % based on total wt. of the product.

14. The solid material of claim 7, comprising the compound of Formula 1 at a concentration above 2 wt. % based on total wt. of the product.

15. The solid material of claim 7, comprising the compound of Formula 1 at a concentration above 5 wt. % based on total wt. of the product.

16. The solid material of claim 7, comprising the compound of Formula 1 at a concentration above 10 wt. % based on total wt. of the product.

17. The coating as claimed in claim 1, wherein when X.sub.1 and X.sub.2=NH, if R is phosphite substituted with Et, R′ is not phenylene; 2-methyl-1,3-phenylene; 2,4,6-trimethyl-phenylene; 1,3-xylylene; diphenylmethane-4,4′-diyl; 1,2-ethylene; 1,3-propylene; 1,6-hexylene; 1,8-(3,6-dioxa octylene) or pyrid-2,6-diyl; if R is phosphite substituted with Me, R′ is not 1,3-phenylene or dimethyl-1,3-propylene, and if R is phosphite substituted with iPr, R′ is not 1,3-phenylene or 1,12-dodecylene.

18. The solid material as claimed in claim 7, wherein when X.sub.1 and X.sub.2=NH, if R is phosphite substituted with Et, R′ is not phenylene; 2-methyl-1,3-phenylene; 2,4,6-trimethyl-phenylene; 1,3-xylylene; diphenylmethane-4,4′-diyl; 1,2-ethylene; 1,3-propylene; 1,6-hexylene; 1,8-(3,6-dioxa octylene) or pyrid-2,6-diyl; if R is phosphite substituted with Me, R′ is not 1,3-phenylene or dimethyl-1,3-propylene, and if R is phosphite substituted with iPr, R′ is not 1,3-phenylene or 1,12-dodecylene.

19. A method of making a flame-retardant coating material, the method comprising: incorporating a compound according to Formula 1 in a coating composition, ##STR00021## with R=phosphite substituted with alkyl, functionalized alkyl, aryl, functionalized aryl, except halogen-substituted alkyl or aryl; R′=alkylene, arylene, alkoxy or aryloxy, all unsubstituted or functionalized, except halogen-substituted; X.sub.1 and X.sub.2=hetero atoms and X.sub.1 and X.sub.2 are the same or different.

20. The method of claim 19, wherein the method comprises incorporating the compound according to Formula 1 in a lacquer.

21. The method of claim 19, wherein the method comprises incorporating the compound according to Formula 1 in a paint.

22. The method of claim 19, wherein when X.sub.1 and X.sub.2=NH, if R is phosphite substituted with Et, R′ is not phenylene; 2-methyl-1,3-phenylene; 2,4,6-trimethyl-phenylene; 1,3-xylylene; diphenylmethane-4,4′-diyl; 1,2-ethylene; 1,3-propylene; 1,6-hexylene; 1,8-(3,6-dioxa octylene) or pyrid-2,6-diyl; if R is phosphite substituted with Me, R′ is not 1,3-phenylene or dimethyl-1,3-propylene, and if R is phosphite substituted with iPr, R′ is not 1,3-phenylene or 1,12-dodecylene.

23. A method of making a flame-retardant solid material, the method comprising: incorporating a compound according to Formula 1 in a solid composition, ##STR00022## with R=phosphite substituted with alkyl, functionalized alkyl, aryl, functionalized aryl, except halogen-substituted alkyl or aryl; R′=alkylene, arylene, alkoxy or aryloxy, all unsubstituted or functionalized, except halogen-substituted; X.sub.1 and X.sub.2=hetero atoms and X.sub.1 and X.sub.2 are the same or different.

24. The method of claim 23, wherein the method comprises incorporating the compound according to Formula 1 in a wood-based material.

25. The method of claim 23, wherein the method comprises incorporating the compound according to Formula 1 in a plastic material.

26. The method of claim 23, wherein when X.sub.1 and X.sub.2=NH, if R is phosphite substituted with Et, R′ is not phenylene; 2-methyl-1,3-phenylene; 2,4,6-trimethyl-phenylene; 1,3-xylylene; diphenylmethane-4,4′-diyl; 1,2-ethylene; 1,3-propylene; 1,6-hexylene; 1,8-(3,6-dioxa octylene) or pyrid-2,6-diyl; if R is phosphite substituted with Me, R′ is not 1,3-phenylene or dimethyl-1,3-propylene, and if R is phosphite substituted with iPr, R′ is not 1,3-phenylene or 1,12-dodecylene.

Description

EMBODIMENT EXAMPLES

(1) A. In a 5 liter four-necked flask equipped with nitrogen feed, reflux condenser, mechanical stirrer, blower counter and thermometer, 481.1 g of tris (2,4,6-diethylphosphite)-s-triazine, in abs. Ethanol, 28.13 g of ethylenediamine are added dropwise at RT. After the addition was complete, the mixture was stirred at RT for 3 h. Subsequently, the batch was concentrated under vacuum and the solid residue was filtered off. Further solid was recovered by cooling overnight and re-filtering. The combined solid fractions were washed with heptane and dried under vacuum at 60° C.

(2) The product was the compound shown in Formula 2.

(3) Analysis:

(4) Cumulative formula C.sub.24H.sub.46N.sub.8O.sub.12P.sub.4

(5) Molecular weight 762.57105

(6) Elemental Analysis C, 37.80; H, 6.08; N, 14.69; O, 25.18; P, 16.25

(7) The product obtained is a free-flowing white powder, which can be admixed in usual commercially available coatings and bulk materials without any problems. B. HEPT (13.9 Kg) was dissolved in absolute ethanol (50 L). Ethylene diamine (845.14 g) was then added dropwise by dropping funnel at ambient temperature. After complete addition, the reaction mixture was stirred at ambient temperature for 4 h, affording a yellow solution. The volatiles were then completely removed under vacuum, resulting in yellow viscous oil. Toluene (30 L) was then added with vigorous stirring. While stirring, the product formed as white powder which was collected by filtration, washed with Toluene (20 L) and then dried in vacuum at 60° C. Yield: 8.19 Kg (75.6%).

(8) The product corresponds to Formula 2.