Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
  • A01N55/08—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing boron
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
  • C07F5/02—Boron compounds
  • C07F5/025—Boronic and borinic acid compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F130/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F130/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
  • C08F130/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing boron
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F30/04—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
  • C08F30/06—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing boron

Definitions

• the present technology relates to dioxaborinane compounds for use as wood preservatives.
• Wood preservatives are used to deter or kill organisms that degrade wood
• wood bearings e.g., wood bearings, utility poles, railroad ties, landscape timbers, docking and marine structures.
• wood preservatives such as heavy metals or copper naphthenates are fully toxic to wood destroying organisms (e.g., bacteria, fungi, wood boring beetles, termites, marine organisms, and animals such as rodents), but have the disadvantage of also being generally toxic to the environment.
• wood preservatives must penetrate into the wood interior. To do so, many wood preservatives are formulated as l iquids that are impregnated into wooden structures. The l iquids typically remain fluid even after they are forced into the wood and are thus prone to leakage from the wood. Leakage of toxic wood preservatives impacts the environment and can raise maintenance costs due to the need for additional labor and materials for the upkeep necessary to reprotect wooden structures.
• the present technology provides for compounds having a pendant dioxaborinane moiety that deters or kills organisms that degrade wood, and a polymerizable moiety that allows the compound to be polymerized in situ after being impregnated into wood products. As such, the compound is effectively fixed within treated wood to deter seepage from the wood and minimize environmental risks.
• Processes for treating wood and wood products with the compound having a pendant dioxaborinane moiety are also provided.
• Wood is coated or impregnated under pressure with the compound having a pendant dioxaborinane moiety, which compound is polymerized on the surface of the wood and/or within the interior of the wood. Whether the wood is surface treated or impregnated, the polymerized compound is effectively fixed.
• pressure and vacuum may be applied in selected sequence to promote impregnation, and heat, blowing air, oxygen, ultraviolet light, and other agents may be employed to promote polymerization of the compound used to surface-treat or impregnate the wood.
• Additional additives may be used to prevent pest infestations and the growth of fungi, or to promote the migration of the compound having a pendant dioxaborinane moiety into the wood.
• a compound is provided as represented by Formula I, or a salt thereof:
• L may be absent, or alkylenyl, alkenylenyl, or arylene, where the alkylenyl and alkenylenyl are optional ly interrupted with one or more oxygen or sulfur atoms;
• X 1 is absent,
• PG is a polymerizable group
• R and R are independently H, alky], alkenyl, aryl, -C(0)R 3 , -C(0)OR 3 , -C(0)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
• R 3 is H, alkyl, alkenyl, or aryl, where the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms.
• R 5 and R 6 are independently H, alkyl, alkenyl, aryl, or -C(0)R 7 ; and R 7 is alkyl, alkenyl, or aryl.
• R 3 is -C(0)alkyl and R 6 is -C(0)alkyl.
• R 5 is -C(0)(C
• a polymer in yet another aspect, includes a polymerization product of the compound as represented by Formula I.
• the polymer has a weight average molecular weight of about 5,000 to about 2,000,000 g/mol.
• a composition in another aspect, includes the compound as represented by Formula I and a cellulosic material.
• the composition includes cellulosic material that is wood, and the composition is a wood-polymer borinane composite material.
• a process is provided of preparing a wood-polymer borinane composite material comprising the steps of: contacting a cellulosic material with a compound as represented by Formula I; and polymerizing the compound as represented by Formula I to form the wood-polymer borinane composite material.
• a method is provided of preparing a compound as represented by Formula I, the method including a first step of contacting a compound of Formula II with a compound of Formula I I I to form the compound of Formula I where Formula I is:
• Formula II I is PG ' -Y.
• L is absent, or is 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 -0-, -Ni l-, -S-, or -P(R 3 )-;
• R 1 and R 2 are independently H, alkyl, alkenyl, aryl, -C(0)R 3 , -C(0)OR 3 , -C(0)N H R 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;
• R 3 is H, alkyl, alkenyl, or aryl, where the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms;
• PG 1 is acrylyl, methacrylyl, epoxyl, isocycany
• a reference to “a cell” includes a plurality of cells
• a reference to “a molecule” is a reference to one or more molecules.
• Alkyl groups include straight chain, branched chain, or cyclic alkyl groups having 1 to 24 carbons or the number of carbons indicated herein. In some embodiments, an alkyl group has from 1 to 16 carbon atoms, from 1 to 1 2 carbons, from 1 to 8 carbons or, in some embodiments, from 1 to 6, or 1 , 2, 3, 4 or 5 carbon atoms.
• straight chain alkyl groups include groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups.
• branched alkyl groups include, but are not limited to, isopropyl, iso-butyl, sec-butyl, tert-butyl, neopentyl, isopentyl, and 2,2-dimethylpropyl groups.
• the alkyl groups may be substituted alkyl groups.
• Cycloalkyl groups are cyclic alkyl groups having from 3 to 1 0 carbon atoms.
• the cycloalkyl group has 3 to 7 ring members, whereas in other embodiments the number of ring carbon atoms range from 3 to 5, 3 to 6, or 5, 6 or 7.
• Cycloalkyl groups further include monocyclic, bicyclic and polycyclic ring systems.
• Monocyclic groups include, e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups.
• Bicyclic and polycyclic cycloalkyl groups include bridged or fused rings, such as, but not limited to, bicyclo[3.2. 1 ]octane, decalinyl, and the l ike.
• Cycloalkyl groups include rings that are substituted with straight or branched chain alkyl groups as defined above. In some embodiments, the cycloalkyl groups are substituted cycloalkyl groups.
• alkenyl groups may be mono-substituted or substituted more than once, such as, but not limited to, mono-, di- or tri-substituted with substituents such as those listed above.
• Representative substituted alkyl groups may be mono-substituted or substituted more than once, such as, but not limited to, mono-, di- or tri-substituted with substituents such as those listed above.
• Alkenyl groups include straight and branched chain alkyl groups as defined above, except that at least one double bond exists between two carbon atoms.
• Representative substituted alkenyl groups may be mono-substituted or substituted more than once, such as, but not lim ited to, mono-, di- or tri-substituted with substituents such as those listed above.
• alkylene cycloalkylene
• alkenylene alone or as part of another substituent means a divalent radical derived from an alkyl, cycloalkyl, or alkenyl group, respectively, as exemplified by -CH2CH2CH2CH2-.
• alkylene, cycloalkylene, and alkenylene linking groups no orientation of the linking group is implied.
• amine refers to -NHR and -NRR' groups, where R, and R' are independently hydrogen, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl group as defined herein.
• R, and R' are independently hydrogen, or a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl group as defined herein.
• amino groups include
• oxo refers to a divalent oxygen group. While the term includes doubly bonded oxygen, such as that found in a carbonyl group, as used herein, the term oxo explicitly includes singly bonded oxygen of the form -O- which is part of a polymer backbone. Thus, an oxo group may be part of an ether l inkage (-0-), an ester l inkage (-0- C(OH. a carbonate linkage (-O-C(O)O-), a carbamate linkage (-O-C(O)N H- or -O- C(O)NR-), and the like.
• Substituted refers to a chemical group as described herein that further includes one or more substituents, such as lower alkyl (including substituted lower alkyl such as haloalkyl, hydroxyalkyl, aminoalkyl), aryl (including substituted aryl), acyl, halogen, hydroxy, amino, alkoxy, alkylamino, acylamino, thioamido, acyloxy, aryloxy, aryloxyalkyl, carboxy, thiol, sulfide, sulfonyl, oxo, both saturated and unsaturated cyclic hydrocarbons (e.g., cycloalkyl, cycloalkenyl) , cycloheteroalkyls and the l ike.
• substituents such as lower alkyl (including substituted lower alkyl such as haloalkyl, hydroxyalkyl, aminoalkyl), aryl (including substituted aryl),
• These groups may be attached to any carbon or substituent of the alkyl, alkenyl, alkynyl, aryl, cycloheteroalkyl, alkylene, alkenylene, alkynylene, arylene, hetero moieties. Additionally, the substituents may be pendent from, or integral to, the carbon chain itself.
• wood or “wood product” include any wood and wood-based materials, including but not limited to wood bearings, utility poles, rai lroad ties, landscape timbers, docking and marine structures, logs, dried lumber, green lumber, fiberboards, strand board, laminated veneer lumber, wood composites, cellulosic composites, plastic wood composites, and engineered wood formed from wood chips.
• the wood may be softwood or hardwood.
• the softwood may include pine species and spruce species, for example, heartwood or sapwood.
• the present technology provides for compounds having a pendant dioxaborinane moiety that deters or ki lls organ isms that degrade wood, and a polymerizable moiety that allows the compound to be polymerized in situ after being impregnated into wood or wood products. As such, the compound is effectively fixed within treated wood to deter seepage from the wood and minimize environmental risks.
• a compound is provided as represented by Formula I, or a salt thereof:
• 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;
• PG 1 is a polymerizable group;
• K 1 and R 2 are independently H, alkyl, alkenyl, aryl, -C(0)R 3 , -C(0)OR 3 , -C(0)NH R 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, where the alkyl and alkenyl are optionally interrupted with one or more oxygen or sulfur atoms.
• L is C ⁇ -C ⁇ o alkylenyl and X ' is absent. In some embodiments, L is C
• PG ' may be acrylyl, methacrylyi, epoxyl, isocycanyl, styrenyi, vinyl, oxyvinyl, thiovinyl, ketovinyl, ketoalkyl, ketoalkoxy, ketoaryl, or cycloalkenyl.
• PG 1 is
• R 4 j s a C, -C 8 alkyl
• L is C , - C 8 alkylenyl and X is absent.
• Illustrative groups for X include -NH-, -0-, -S-, and -PH-
• R 1 is H and R 2 is H.
• R l is Cj -
• R 2 is Ci -C 6 alkyl.
• L is Ci -Cio alkylene.
• L is C
• X is absent
• R and R are independently H or C
• L is C
• X 1 is oxo
• R 1 and R 2 are independently H or C1-C6 alkyl.
• the compound of Claim 1 may be a compound represented by Formula IA :
• 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;
• PG 1 is a polymerizable group, and R 5 and R 6 are independently H, alkyl, alkenyl, aryl, or -C(0)R 7 ; and R 7 is alkyl, alkenyl, or aryl.
• R 5 is -C(0)alkyl and R 6 is -C(0)alkyl.
• R 5 is - C(0)(Ci5-C 2 o alkyl) and R 6 is -C(O)(Ci 5 -C 20 alkyl).
• R 4 is a Ci -C 8 alkyl.
• PG 1 is
• L is C
• a polymer in another aspect, includes a polymerization product of the compound as represented by Formula I.
• the polymer has a weight average molecular weight of about 5,000 to about 2,000,000 g/mol.
• the polymer may have a weight average molecular weight of about 1 00,000 to about 1 ,000,000 g/mol.
• compositions that include the compound as represented by Formula I and a cellulosic material.
• the composition includes cellulosic material that is wood, anji the composition is a wood-polymer borinane composite material.
• the composition may include an article such as, but not limited to, a railroad tie, a pole, or a building member.
• a process is provided of preparing a wood-polymer borinane composite material, the process including contacting a cellulosic material with a compound represented by Formula I ; and polymerizing the compound:
• the contacting step may include employing a pressure process, a full cell process, or a fluctuation pressure process to impregnate the compound into the cel lulosic material.
• a pressure process for example, cellulosic materials such as woods typical ly are porous and the compounds may be forced into the porous structure by pressuring the system.
• a vacuum/pressurization process may be used, where a vacuum is drawn on the cellulosic material to withdraw some gases or low boiling point compounds from the cellulosic material and a subsequent pressurization forces the compound of Formula I into the cellulosic material.
• the polymerizing step may also include activating the polymerizable group.
• the activating of the polymerizable group may includes heating the
• the thermal initiator may include, but is not limited to, 4,4-azobis(4-cyanovaleric acid), l , l '-azobis(cyclohexanecarbonitrile), 2,2'- azobisisobutyronitrile, benzoyl peroxide, tert-buXy ⁇ peracetate, lauroyl peroxide, or dicumyl peroxide.
• the activating the polymerizable group includes adding a photochemical initiator to the polymerizable group
• the initiator may include, but is not l imited to, 3-butyl-2- [5-( l -butyl-3,3-dimethyl- l ,3-dihydro-indol-2-ylidene)-penta- l ,3
• the step of activating the polymerizable group includes heating the polymerizable group to a temperature of about 40 °C to about 1 20 °C.
• a process for treating wood and wood products with the compound having a pendant dioxaborinane moiety may include applying a compound of Formula I, or a preservative solution thereof, into wood under a pressure regime to infuse the compound into the wood. Such methods of infusion may optionally further include the selective application of increased pressure or vacuum. In further embodiments, methods are provided that involve an additional step of polymerizing, in-situ, the compound of Formula I within the wood. Both steps, which are described more thoroughly below, can be conducted separately or simultaneously.
• the wood Before applying the preservative solution of a compound of Formula 1, the wood may optionally be seasoned unti l a substantial fraction of free water has been removed from the cell spaces, with the resulting seasoned wood having its moisture content reduced by at least 25%, or at least 50%, or at least 75%, varying slightly with different species of wood.
• decreasing the moisture content of the wood creates more space to apply the preservative solution of a compound of Formula I into the wood, and decreases the likelihood that splits will develop in the applied wood.
• cutting, machining, and/or boring of the wood is conducted before the preservative solution of a compound of Formula I is applied.
• the preservative solution of a compound of Formula I may be appl ied to wood by dipping, soaking, spraying, brushing, injecting, or any other well known means.
• the preservative solution of a compound of Formula I may be applied at ambient temperature, but advantageously, can also be heated to assist penetration of the compound into the wood.
• methods are provided in which the preservative solution of a compound of Formula I is applied to the wood by impregnating it into the wood.
• the preservative solution of a compound of Formula I is applied as a surface coat which is polymerized to encapsulate the wood.
• the preservative solution of a compound of Formula I wi ll be present in the final wood product in an amount of about 0.01 wt. % to about 1 0.0 wt. %.
• This may include from about 0.10 wt. % to about 3.0 wt. %, or from about 0. 1 0 wt. % to about 2.0 wt. %, or from about 0. 1 0 wt. % to about 1.0 wt. %, or from about 0.10 wt. % to about 0.50 wt. %, or from about 0. 1 0 wt. % to about 0.30 wt. %.
• Specific examples of weight percent include about 0.01 wt.
• the wood may also be treated with one or more additives either before, after, or simultaneously upon treatment with the preservative solution of a compound of Formula 1.
• additives may include solvents such as glycol-based solvents, water repellents, such as waxes, resins, or polymers, fire retardants, such as phosphates, mildewicides, insecticides, mouldicides, or pigments.
• solvents such as glycol-based solvents, water repellents, such as waxes, resins, or polymers
• fire retardants such as phosphates, mildewicides, insecticides, mouldicides, or pigments.
• phosphates such as glycol-based solvents
• water repellents such as waxes, resins, or polymers
• fire retardants such as phosphates, mildewicides, insecticides, mouldicides, or pigments.
• a vacuum or decreased pressure can be appl ied to degas the wood sample and maximize pore sizes within the wood prior to the application of the preservative solution of a compound of Formula I.
• Vacuum and/or pressure techniques may also be used to impregnate the wood, including both the "Empty Cell” process and the “Full Cell” process, both of which are well known to those skilled in the art.
• existing processes are used to impregnate the wood with the preservative solution of a compound of Formula I, including the Bethell, Lowry, Reuping, and SU processes.
• the Bethel l process involves using an initial vacuum to remove air from the wood cells and then flooding a cylinder loaded with the wood under vacuum with a preservative solution of a compound of Formula I. Positive pressure of, for example, about 1400 kPa is then applied for a predetermined time, the preservative solution of the compound of Formula I is drained and a final vacuum is drawn.
• Positive pressure of, for example, about 1400 kPa is then applied for a predetermined period, the cylinder is then drained and a final vacuum drawn.
• the net uptake of the preservative solution of a compound of Formula 1 is lower because the air is not removed from the wood cells but is compressed during treatment, thus resulting in kickback of the preservative solution of a compound of Formula 1 when pressure is released and the timber evacuated.
• the Reuping process involves applying an initial air pressure of, for example, about 350 kPa to the wood in the cylinder and then flooding the cylinder with a solution of the preservative solution of a compound of Formula I while holding this initial air pressure. Increased pressure of, for example, about 1000 kPa is then applied and, after a predetermined time, the pressure is released and the cylinder drained. A final vacuum is then drawn. This process has a lower net uptake of the preservative solution of a compound of Formula I than both the Bethell and Lowry processes.
• the MSU process is a modification of the Reuping process.
• the Reuping process is carried out but the cylinder is drained while maintaining a pressure of, for example, about 300 kPa. Heat is then applied by steaming the wood. After the steaming period, kickback is allowed to occur by reducing the pressure and a final vacuum is drawn.
• pre- and post- impregnation vacuum application may be employed or eliminated.
• the preservative solution of a compound of Formula 1 may be preheated to accelerate impregnation and to increase the level of penetration into the wood as well as to promote polymerization of the compound of Formula I during the impregnation process.
• the polymerization prevents, or at least minimizes, later leaching of the compound of Formula I, and the preservative solution thereof, from the wood.
• the method provides a polymerized solid surface coat of the preservative solution of the compound of Formula I.
• In-situ polymerization of the compound of Formula I during and after impregnation of the wood can be promoted by conventional means.
• the in-situ polymerization includes activating the polymerizable group.
• activating the polymerizable group includes heating, activating the
• Electromagnetic radiation includes radiation from the
• activating the polymerizable group includes activating the polymerizable group with ultraviolet (UV), visible, or near-infrared (FR) radiation.
• UV radiation has a wavelength from about 1 0 nm to about 390 nm.
• Visible radiation has a wavelength from about 390 nm to about 750 nm.
• Near-IR radiation has a wavelength from about 750 nm to about 3 ⁇ .
• the in-situ polymerization is promoted through the application of heat.
• the in-situ polymerization is promoted by adding a thermal initiator.
• the amount and duration of heat to be applied varies depending, for example, upon the size of the wood under treatment or the nature of the wood.
• in-situ polymerization of the compound of Formula I serves to fix the compound of Formula 1 within the wood, or at least increase the compound's viscosity within the wood, together with any additives from the preservative solution.
• in-situ polymerization of the compound of Formula I is promoted through the application of UV radiation. In certain embodiments, in-situ polymerization of the compound of Formula I is promoted by adding a photochemical initiator:
• methods are provided to surface treat the wood with a layer of the preservative solution of a compound of Formula I and polymerize the surface layer to encapsulate the wood.
• the surface layer of the compound of Formula I is polymerized with the application of heat or ultraviolet radiation.
• a method is provided of preparing a compound as represented by Formula 1, the method including a first step of contacting a compound of Formula II with a compound of Formula III to form the compound of Formula I where
• Formula III is PG' -Y.
• PG 1 may be a group as described above and Y is a leaving group.
• Step 1 Synthesis ofbis-esters and ethers of pentaerythritol (Scheme 1 ).
• 2,2-Bis(benzyloxymethyl)-l ,3-propanediol was prepared by combining pentaerythritol (10.36 g, 100 mmol) and dibutyltin oxide (50.00 g, 200 mmol) under reflux in methanol for four hours. The solvent was then removed by evaporation and the glassy residue was dried by keeping for 1 day at 40 °C under diminished pressure, and then by co-evaporation with toluene. The product was stored in a desiccator. [0060] A suspension of the above stannylene derivative (6.00 g, 1 0 mmol) in toluene
• Each of the possible compounds of varying R groups may be prepared by substituting the appropriate diol for the 2,2-bis(benzyloxymethyl)- l ,3-propanediol as described for Step 2, above.
• Example 2 Synthesis of fatty acid acrylic-acrylic-dioxaborinane wood preservatives (Scheme 4).
• Octadecanoic acid 2-[3-(2-methyl-acryloyloxy)-propyl]-5 -octadecanoyloxymethyl-[ l ,3,2]dioxaborinan-5-ylmethyl ester was synthesized from stearic acid using the procedures outlined above.
• Dioxaborinane compounds were likewise prepared from other saturated fatty acids, such as lauric and palmitic acid, and unsaturated fatty acids, such as oleic, ricinoleic, linoleic, and linolenic acid.
• Example 3 Pressure Treatment Process. Pressure treatment ensures that the acrylic-dioxaborinanes completely impregnates the wood. The treatment of the wood is carried out in closed vessels where the wood is exposed to the acrylic-dioxaborinanes and then pressure and/or vacuum is applied. The acrylic-dioxaborinane penetrates deeply and uniformly into the wood. The conditions under which the acrylic-dioxaborinane is applied can be controlled to vary the degree to which the acrylic-dioxaborinane penetrates the wood and is retained. The pressure processes can be further adapted for large-scale protection of railroad ties, telephone poles, bui lding members, and structural materials.
• Example 4 Full-cell Process.
• the full-cell process is used as a variation of the pressure treatment process. However, in the full-cell process it is preferable to keep as much of acrylic-dioxaborinane preservative absorbed into the wood during the pressure period as possible. The desired retention of the acrylic-dioxaborinane preservative is achieved by changing the concentration of the solution.
• Example 5 Fluctuation Pressure Process.
• the fluctuation process is another variation of the pressure process.
• the fluctuation process is a "dynamic" process because the conditions under which the acrylic-dioxaborinane is applied are constantly changing.
• the pressure inside the preservative application cylinder changes between vacuum and high pressure within a few seconds in the fluctuation process. This process is used for woods that can split or otherwise fail under other pressure application procedures. General ly, as a result of this fluctuation process, penetration depths of the preservatives may be limited.
• Example 6 Polymerization in wood. The acrylic wood preservative was polymerized once it was within the wood structure (Scheme 5).
• This step fixed the wood preservative into the wood structure, preventing it from leaching out of the wood, and further served to strengthen the wood.
• This step is optional as the acrylic-dioxaborinane preservative can be used to preserve wood without polymerizing the preservative.
• the acrylic- dioxaborinane preservative was introduced into the wood structure by means of pressure, as described above, where it filled the fine grains and voids located within the wood. A fter the acrylic-dioxaborinane preservative was introduced into the wood structure, it was heated to 65-75°C, causing the acrylic-dioxaborinane preservative to polymerize into a solid form.
• acrylic-dioxaborinane preservative Once the acrylic-dioxaborinane preservative is polymerized within the wood structure it will not readily flow to the base of the wood structure and leak into the surrounding environment. Rather, the polymerized acrylic-dioxaborinane preservative will generally remain fixed throughout the treated wood structure and thereby persist within the wood structure for longer periods of time relative to existing l iquid preservatives.
• al l ranges disclosed herein also encompass any and all possible subranges and combinations of subranges thereof. Any listed range can be easily recognized as sufficiently describing and enabl ing the same range being broken down into at least equal halves, thirds, quarters, fifths, tenths, etc. As a non-limiting example, each range discussed herein can be readily broken down into a lower third, middle third and upper third, etc.

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