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 I:
wherein:
L is alkylenyl which is optionally interrupted with one or more oxygen or sulfur atoms;
X 1 is absent;
PG 1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;
R 1 and R 2 are independently H, alkyl, alkenyl, aryl, —C(O)R 3 , —C(O)OR 3 , —C(O)NHR 3 , or R 1 and R 2 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, wherein the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms.
2. The compound of claim 1 , wherein PG 1 is —OC(O)C(R 4 )=CH 2 , —OC(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.
3. 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.
4. The compound of claim 1 , wherein PG 1 is —C(O)CH=CH 2 .
5. The compound of claim 1 , wherein R 1 is H and R 2 is H.
6. The compound of claim 1 , wherein R 1 is C 1 -C 6 alkyl and R 2 is C 1 -C 6 alkyl.
7. The compound of claim 1 , wherein L is C 1 -C 10 alkylenyl.
8. A polymer comprising a polymerization product of a compound of Formula I:
wherein:
L is alkylenyl which is optionally interrupted with one or more oxygen or sulfur atoms;
X 1 is absent;
PG 1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;
R 1 and R 2 are independently H, alkyl, alkenyl, aryl, —C(O)R 3 , —C(O)OR 3 , —C(O)NHR 3 , or R 1 and R 2 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, wherein the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms.
9. The polymer of claim 8 , 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.
10. The polymer of claim 8 , wherein PG 1 is —C(O)C(R 4 )=CH 2 and R 4 is a C 1 -C 8 alkyl.
11. The polymer of claim 8 , wherein PG 1 is —C(O)CH=CH 2 .
12. The polymer of claim 8 having a weight average molecular weight of about 5,000 g/mol to about 2,000,000 g/mol.
13. A process of preparing a wood-polymer borinane composite material comprising:
contacting a cellulosic material with a compound of Formula I; and
polymerizing the compound of Formula I to form the wood-polymer borinane composite material;
wherein:
Formula I is:
wherein:
L is alkylenyl which is optionally interrupted with one or more oxygen or sulfur atoms;
X 1 is absent;
PG 1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;
R 1 and R 2 are independently H, alkyl, alkenyl, aryl, —C(O)R 3 , —C(O)OR 3 , —C(O)NHR 3 , or R 1 and R 2 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, wherein the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms.
14. The process of claim 13 , wherein the polymerizing comprises activating the polymerizable group.
15. The process of claim 14 , wherein the activating comprises heating the polymerizable group, 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 14 , wherein the activating the polymerizable group comprises adding a thermal initiator to the polymerizable group 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.
17. The process of claim 14 , wherein activating the polymerizable group comprises 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.
18. The process of claim 14 , wherein activating the polymerizable group comprises heating the polymerizable group to a temperature of about 40° C. to about 120° C.
19. An article comprising the polymer of claim 13 and a cellulosic material.
20. The article of claim 19 which is a railroad tie, a pole for supporting cable, or a building member.