Dioxaborinanes and uses thereof
View Patent ↗A dioxaborinane compound, or salt thereof, where boron has two oxy substituents, each independently substituted with H, alkyl, alkenyl, aryl, —C(O)R 3 , —C(O)OR 3 , —C(O)NHR 3 , or the two oxy substituents, together with the oxygen atoms to which they are bonded, join to form a 5- or 6-membered ring; and R 3 is H, alkyl, alkenyl, or aryl, where the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms; and where boron also has the substituent -L-X 1 -PG 1 ; where L may be absent, or alkylenyl, alkenylenyl, or arylene, where the alkylenyl and alkenylenyl are optionally interrupted with one or more oxygen or sulfur atoms; X 1 is absent, or is amino, oxo, thio, or phosphino; and PG 1 is a polymerizable group. The dioxaborinane compound can be used as a wood preservative.
1. A compound of Formula IA:
wherein:
L is absent, or is alkylenyl, alkenylenyl, or arylene, wherein the alkylenyl and alkenylenyl are optionally interrupted with one or more oxygen or sulfur atoms;
X 1 is absent, or is amino, oxo, thio, or phosphino;
PG 1 is a polymerizable group;
R 5 and R 6 are independently H, alkyl, alkenyl, aryl, or —C(O)R 7 ; and
R 7 is alkyl, alkenyl, or aryl.
2. The compound of claim 1 , wherein PG 1 is acrylyl, methacrylyl, epoxyl, isocycanyl, styrenyl, vinyl, oxyvinyl, thiovinyl, ketovinyl, ketoalkyl, ketoalkoxy, ketoaryl, or cycloalkenyl.
3. The compound of claim 1 , wherein PG 1 is —C(O)C(R 4 )═CH 2 , —C(O)CH═CH 2 , —O—CH═CH 2 , —S—CH═CH 2 , —N═C═O,
or
and R 4 is a C 1 -C 8 alkyl.
4. The compound of claim 1 , wherein PG 1 is —C(O)C(R 4 )═CH 2 and R 4 is a C 1 -C 8 alkyl.
5. The compound of claim 1 , wherein PG 1 is —C(O)CH═CH 2 .
6. The compound of claim 1 , wherein X 1 is —NH—, —O—, —S—, or —PH—.
7. The compound of claim 1 , wherein L is C 1 -C 10 alkylene.
8. The compound of claim 1 , wherein R 5 is —C(O)alkyl and R 6 is —C(O)alkyl.
9. The compound of claim 1 , wherein X 1 is —O—.
10. A polymer comprising a polymerization product of the compound of claim 1 .
11. A composition comprising the compound of claim 1 and a cellulosic material.
12. The composition of claim 11 , wherein the cellulosic material is wood, and the composition is a wood-polymer borinane composite material.
13. A process of preparing a wood-polymer borinane composite material comprising:
contacting a cellulosic material with a compound of Formula IA; and
polymerizing the compound of Formula IA to form the wood-polymer borinane composite material;
wherein:
Formula IA is:
L is absent, or is alkylenyl, alkenylenyl, or arylene, wherein the alkylenyl and alkenylenyl are optionally interrupted with one or more oxygen or sulfur atoms;
X 1 is absent, or is amino oxo, thio, or phosphino;
PG 1 is a polymerizable group;
R 5 and R 6 are independently H, alkyl, alkenyl, aryl, or —C(O)R 7 ; and
R 7 is alkyl, alkenyl, or aryl.
14. The process of claim 13 , wherein the contacting comprises employing a pressure process, a full cell process, or a fluctuation pressure process.
15. The process of claim 13 , wherein the polymerizing comprises-activating the polymerizable group with UV, visible, or near-IR radiation, adding a thermal initiator to the polymerizable group, or adding a photochemical initiator to the polymerizable group.
16. The process of claim 13 , wherein the polymerizing comprises adding a thermal initiator that is 4,4-azobis(4-cyanovaleric acid), 1,1′-azobis(cyclohexanecarbonitrile), 2,2′-azobisisobutyronitrile, benzoyl peroxide, tert-butyl peracetate, lauroyl peroxide, or dicumyl peroxide, or adding a photochemical initiator to the polymerizable group that is 3-butyl-2-[5-(1-butyl-3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-penta-1,3-dienyl]-1,1-dimethyl-1H-benzo[e]indolium triphenylbutylborate, 3-butyl-2-[5-(3-butyl-1,1-dimethyl-1,3-dihydro-benzo[e]indol-2-ylidene)-penta-1,3-dienyl]-1,1-dimethyl-1H-benzo[e]indolium triphenylbutylborate, or 6-hydroxy-2,4,5,7-tetraiodo-3-oxo-9,9a-dihydro-3H-xanthene-9-carbonitrile.
17. An article comprising the composition of claim 12 .
18. The article of claim 17 which is a railroad tie, a pole for supporting cable, or a building member.
19. A method of preparing a compound of Formula IA, the method comprising:
contacting a precursor compound with a compound of Formula III to form the compound of Formula IA;
wherein:
Formula IA is:
the precursor compound is:
Formula III is PG 1 -Y;
L is absent, or is alkylenyl, alkenylenyl, or arylene, wherein the alkylenyl and alkenylenyl are optionally interrupted with one or more oxygen or sulfur atoms;
X 1 is absent, or is —O—, —NH—, —S—, or —P(R 3 )—;
R 5 and R 6 are independently H, alkyl, alkenyl, aryl, or —C(O)R 7 ;
R 7 is alkyl, alkenyl, or aryl
PG 1 is acrylyl, methacrylyl, epoxyl, isocycanyl, styrenyl, vinyl, oxyvinyl, thiovinyl, ketovinyl, ketoalkyl, ketoalkoxy, ketoaryl, or cycloalkenyl; and
Y is a leaving group.