A dioxaborinane compound, or salt thereof, where boron has two oxy substituents, each independently substituted with H, alkyl, alkenyl, aryl, —C(O)R3, —C(O)OR3, —C(O)NHR3, 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
A dioxaborinane compound, or salt thereof, where boron has two oxy substituents, each independently substituted with H, alkyl, alkenyl, aryl, —C(O)R3, —C(O)OR3, —C(O)NHR3, 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 R3 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-X1-PG1; 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; X1 is absent, or is amino, oxo, thio, or phosphino; and PG1 is a polymerizable group. The dioxaborinane compound can be used as a wood preservative.
대표청구항▼
1. A compound of Formula I: wherein: L is alkylenyl which is optionally interrupted with one or more oxygen or sulfur atoms;X1 is absent;PG1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;R1 and R2 are independently H, alkyl, alkenyl, aryl, —C(O)R3, —C(O)OR
1. A compound of Formula I: wherein: L is alkylenyl which is optionally interrupted with one or more oxygen or sulfur atoms;X1 is absent;PG1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;R1 and R2 are independently H, alkyl, alkenyl, aryl, —C(O)R3, —C(O)OR3, —C(O)NHR3, or R1 and R2 together with the oxygen atoms to which they are bonded join to form a 5- or 6-membered ring; andR3 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 PG1 is —OC(O)C(R4)=CH2, —OC(O)CH=CH2, —O—CH=CH2, —S—CH=CH2, —N=C=O, or and R4 is a C1-C8 alkyl. 3. The compound of claim 1, wherein PG1 is —C(O)C(R4)=CH2 and R4 is a C1-C8 alkyl. 4. The compound of claim 1, wherein PG1 is —C(O)CH=CH2. 5. The compound of claim 1, wherein R1 is H and R2 is H. 6. The compound of claim 1, wherein R1 is C1-C6 alkyl and R2 is C1-C6 alkyl. 7. The compound of claim 1, wherein L is C1-C10 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;X1 is absent;PG1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;R1 and R2 are independently H, alkyl, alkenyl, aryl, —C(O)R3, —C(O)OR3, —C(O)NHR3, or R1 and R2 together with the oxygen atoms to which they are bonded join to form a 5- or 6-membered ring; andR3 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 PG1 is —C(O)C(R4)=CH2, —C(O)CH=CH2, —O—CH=CH2, —S—CH=CH2, —N=C=O, or and R4 is a C1-C8 alkyl. 10. The polymer of claim 8, wherein PG1 is —C(O)C(R4)=CH2 and R4 is a C1-C8 alkyl. 11. The polymer of claim 8, wherein PG1 is —C(O)CH=CH2. 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; andpolymerizing 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;X1 is absent;PG1 is an acrylyl, methacrylyl, epoxyl, isocyanyl, oxyvinyl, thiovinyl, or cycloalkenyl group;R1 and R2 are independently H, alkyl, alkenyl, aryl, —C(O)R3, —C(O)OR3, —C(O)NHR3, or R1 and R2 together with the oxygen atoms to which they are bonded join to form a 5- or 6-membered ring; andR3 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.
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