USOO8945706B2

(12) UnIted States Patent (10) Patent N0.: US 8,945,706 B2

Wang (45) Date of Patent: Feb. 3, 2015

(54) POLYMERIC COMPOSITION FOR 5,770,319 A * 6/1998 Franich et al. .............. .. 428/528
CELLULOSIC MATERIAL BINDING AND 5,895,804 A * 4/ 1999 Lee at al~ ~~~~~ ~~ ~~ 525/543
2003/0074741 A1 * 4/2003 Sivik et al. ..... . . . . . .. 8/137
MODIFICATIONS 2004/0048541 A1 * 3/2004 Offord et al. ............... .. 442/364
_ _ 2004/0077517 A1 4/2004 Boekh et al.
(76) Inventorr Yln Wang, Belllngham, WA (US) 2004/0261961 A1 * 12/2004 Aitta et al. .................... .. 162/76
2006/0252855 A1 * 11/2006 Pisanova et al. .............. .. 524/47
(*) Notice: Subject to any disclaimer, the term of this 2007/0082187 A1 4/2007 Wang et a1.
patent is extended or adjusted under 35
U_s_c_ 15403) by 1185 days_ FOREIGN PATENT DOCUMENTS
. WO PCT 1/2009
(21) Appl.No.. 12/164,062 [Enos/068691
(22) Filed: Jun. 29, 2008
OTHER PUBLICATIONS
(65) Prior Publication Data _ _ _
Ruffo et al., Moderate to HIgh Dose of Maltodextnn Before Exerclse
Us 2009/0011214 A1 Jan- 8, 2009 Improves Glycogen Availability in Soleus and Liver After Prolonged
_ _ Swimming in Rats, Journal of Exercise Physiology, 2009, vol. 12, pp.
Related U.S. Appllcatlon Data 3068 *
(60) Provisional application No. 60/947,649, ?led on Jul. 2, Random House Dictionary, De?nition 0fOlig0mer, 2014, Random
2007. House Inc., p. 1.*
WikipediazAbout (Retrieved May 16, 2014).*
(51) Illt- Cl- International Search Report for PCT Application No. US2008/
B32B 3/26 (2006.01) 068691 dated Oct. 1, 2008.
B05D 3/02 (2006.01)
B05D 3/12 (2006.01) * cited by examiner
C08G 63/00 (2006.01)
B2 7K 3/15 (2006.01) _
305D [/18 (200601) Primary Examiner * Callie Shosho
3051) 3/04 (200601) Assistant Examiner i Patrick English
(52) US. Cl. (74) Attorney, Agent, or Firm * Tianhua Gu; Global IP
CPC B27K3/15 (2013.01); B05D 1/18 (2013.01); Sefivces
B05D 3/0493 (2013.01); B05D 2203/20
(2013.01)
USPC ....... .. 428/305.5; 427/297; 428/533; 527/300 (57) ABSTRACT
(58) Field Of ClaSSi?cation searCh / A polymer composition suitable for wood treatment or bind
USPC .... ........... ............ 428 305.5 mg comprises a reaction product of at least a polyol and at
see app Icanon e or comp ete seam lstory' least a crosslinking agent. The crosslinking agent has at least
(56) References Cited 2 carboxylic acid groups per molecule. A wood product com
prising a wood substrate and a polymer composition as well
U.S. PATENT DOCUMENTS as a wood treatment process are also disclosed.

4,147,679 A * 4/1979 Scriven et al. .............. .. 523/404

5,162,394 A * 11/1992 Trocino et al. .............. .. 523/208 15 Claims, No Drawings
 US 8,945,706 B2
1 2
POLYMERIC COMPOSITION FOR the process embodiments described herein are not con
CELLULOSIC MATERIAL BINDING AND strained to a particular order or sequence. Additionally, some
MODIFICATIONS of the described embodiments or elements thereof can occur
or be performed at the same point in time.
CROSS-REFERENCE TO RELATED There is no limitation on the wood substrate suitable for
APPLICATIONS treatment according to the invention. The term wood sub
strate herein includes any solid cellulosic materials that com
This application claims the bene?t of US. Provisional prise ?bers of cellulose and/ or hemicellulose. The wood sub
Application No. 60/947,649, ?led on Jul. 2, 2007. strate may comprise any wood species in any geometric
shapes. Suitable wood species may include, but not limited to,
TECHNICAL FIELD soft wood, hard wood (maple, oak, as examples), bamboo,
corn stalk, sugar cane bagasse, straw stalks (such as rice straw
The ?eld to which the disclosure generally relates includes and wheat straw), seed ?ax stalk and any hybrid wood mate
wood binding and wood treatments. rials. Speci?c examples of wood species may include Radiata
BACKGROUND Pine, Scots Pine, Red Pine, Yellow Pine, Maple, Alder, Birch,
Aspen, Balsawood, and Beech. The wood substrate may be a
Polymer compositions have been used to treat wood mate wood sheet, wood ?bers, green lumber, pre-dried lumber,
rials and to adhesively bind wood materials together. US. Pat. beam, plank, veneer, chip, and wood particles. The wood
Nos. 5,770,319 and 5,162,394 disclosed several wood treat 20 substrate may be polished, steamed, bleached, or etched
ment compositions and processes. before treated according to the invention.
Polyester resins are typically synthesized by reacting a The wood substrate typically includes voids in at least a
monomer containing about 2 hydroxyl groups with another portion of the substrate. Typical voids are cell voids formed
monomer containing about 2 carboxylic acid groups. To yield during the formation of the wood as part of a tree. The voids
a high molecular weight resin with practical mechanical 25 may be interconnected in channels. Soft wood materials tend
strength, the two monomers need to be free of impurities that to include larger size channels, and higher volume fraction of
may cause side reactions, and the molar ratio of hydroxyl voids. Voids may also be created arti?cially by any known
group to carboxylic acid group needs to be approximately 1 to chemical or mechanical processes, such as etching and incis
1. Furthermore, the polymerization reaction needs to reach ing. The size of the voids may range from nanometers to
greater than 99% yield to achieve suf?cient molecular weight, 30
millimeters in terms of the maximal linear dimension of the
necessitating removal of even minute amounts of water, a void cross-section.
by-product of the reaction. Polyester resins have not been A suitable polyol may include any monomeric, oligomeric
widely used as wood adhesives or as resins to modify wood and polymeric molecules having at least 2 hydroxyl groups
materials. per polyol molecule. Examples of suitable polyols may
35
SUMMARY OF EXEMPLARY EMBODIMENTS include, but not limited to, polyvinyl alcohol, polysaccha
OF THE INVENTION rides, beta-hydroxyl polyacrylates, pentaerythritol, chitosan,
oligomers derived from pentaerythritol, and maltodextrin.
A polymer composition suitable for wood treatment or Beta-hydroxyl polyacrylate includes any polyacrylates hav
binding comprises a reaction product of at least a polyol and 40 ing at least 2 [3-hydroxyl acrylate monomer units per polymer
at least a crosslinking agent. The crosslinking agent has at molecule. The polyol may be further modi?ed to include
least 2 carboxylic acid groups per molecule. other chemical groups as long as there are still at least 2
A wood product comprises a wood substrate having voids hydroxyl groups per molecule. Therefore, any derivatives of
and a polymer composition comprising a reaction product of above mentioned polyol examples having at least 2 hydroxyl
at least a polyol and at least a crosslinking agent having at 45 groups per molecule may be used according to the invention.
least 2 carboxylic acid groups per molecule. The polymer A polyol having greater than 2 hydroxyl groups per molecule
composition may be disposed substantially inside the voids. can have greater reactivity toward the crosslinking agent
A process of wood treatment comprises: providing a wood describedbelow. A polyol having, for example, 3 to 1000, 5 to
substrate having voids; impregnating the wood substrate with 1000, 10 to 1000, or 20 to 1000 hydroxyl groups per molecule
a mix composition comprising a polyol and a crosslinking 50 can exhibit high reactivity with the crosslinking agent. Water
agent having at least two carboxylic acid groups; and causing soluble polysaccharides such as maltodextrin are examples of
a chemical reaction between the polyol and the crosslinking such a polyol.
agent to form a water insoluble polymer. Maltodextrin is referred to herein as a polysaccharide
Other exemplary embodiments of the present invention derived from (x-l .4 linked (x-D- glucose. Maltodextrin may be
will become apparent from the detailed description provided 55 prepared by hydrolysis of a starch. Maltodextrin may have a
hereinafter. It should be understood that the detailed descrip DE (dextrose equivalent) less than about 20. DE is a measure
tion and speci?c examples, while disclosing exemplary of reducing power compared to a dextrose standard of 100.
embodiments of the invention, are intended for purposes of The higher the DE, the greater the extent of starch depoly
illustration only and are not intended to limit the scope of the merization with a resulting smaller average molecule size.
invention. 60 Maltodextrins having any chain length as well as any stereo
isomer con?gurations may be used. Non-limiting examples
DETAILED DESCRIPTION OF EXEMPLARY of maltodextrin include maltotetraose, maltohexaose, and
EMBODIMENTS maltodecaose. Maltodextrin having a dextrose equivalent
value in the range of1 to 25 or 2 to 12 may be used as a polyol
The following description of the embodiment(s) is merely 65 material.
exemplary in nature and is in no way intended to limit the A maltodextrin may be used alone or in combination with
invention, its application, or uses. Unless speci?cally stated, one or more other maltodextrins or combined with other
 US 8,945,706 B2
3 4
water-soluble carbohydrates such as starch hydrolysates groups, may be combined with a crosslinking agent having at
including other dextrins, modi?ed carbohydrates, and other least 2, 3, 4, or 5 carboxylic acid groups. In one particular
polymer resins. example, maltodextrin and citric acid are included in the mix
The terms maltodextrin and polysaccharide herein composition. The molar ratio of citric acid to maltodextrin
may also include any derivatives of maltodextrins and may range from 2:1 to 30:1, or 5:1 to 30:1. In both ranges of
polysaccharides modi?ed by, for example, acetylation, sul those ratios, the corresponding carboxylic acid group to
fonation, dehydration, alkoxylation, or any other chemical hydroxyl group molar ratio is greater than 1:10. In the mix
means as long as there are at least 2 hydroxyl groups per formulation, the carboxylic acid group of the crosslinking
derivative molecule. agent can also react with the hydroxyl group of the wood
The crosslinking agent may include any chemical com substrate, resulting in covalent attachment to the cellulose
pounds having at least 2 carboxylic acid groups or 2 groups ?bers of the wood substrate. Such strong covalent bonding to
having reactivity equivalent to carboxylic acid groups per the wood substrate can further enhance the properties (such as
molecule. Carboxylic acid herein includes carboxylic acid, hardness, dimension stability, rot resistance . . . etc.) of the
carboxylic anhydride, carboxylic acid methyl or ethyl ester, treated wood. The mix composition typically has low viscos
and carboxylic acid halide groups (including acid ?uoride, ity, about 20 to 800 centipoises, and it can diffuse or migration
acid chloride, acid bromide and acid iodide) due to their readily through the channels and voids in a wood substrate.
similar abilities to react with a hydroxyl group to form an In one exemplary process, a wood substrate (such as a solid
ester linkage. The crosslinking agent thus is capable of react wood or a wood veneer) having voids is put under reduced
ing with the polyol described above to form crosslinking ester pressure (vacuum). The mix composition is subsequently
linkages, rendering the reaction product insoluble in water. 20 brought in contact with the wood substrate. Due to the
Non-limiting examples of the crosslinking agent include cis, reduced pressure, the mix composition tends to drawn into the
trans-butenedioic acid, ethylene-diamine-tetraacetic acid voids by ?ow, migration and/or diffusion. The mix composi
(EDTA), citric acid, citraconic acid, mesaconic acid, butane tion can be forced to further ?ow, migrate or diffuse into the
tetracarboxylic acid (BTCA), tartaric acid, fatty acids, suc voids when an elevated pressure is subsequently applied. Any
cinic acid, itaconic acid, polyacrylic acid and resins having 25 desired evacuationipressure schedule including evacuation
acrylic or methacrylic acid monomer unit. and/or elevated pressure and/or cycles of evacuation-pressur
Optionally, the crosslinking agent may further comprise a ization, or other impregnation processes known in the art may
vinyl group, represented by the chemical structural unit, be used. In one example, the wood substrate is evacuated at
more than 60% vacuum, immersed in the mix composition,
30 and subsequently pressurized at a pressure from about 50 psi
to 250 psi (about 345 kilopascal to about 1,724 kilopascal).
The wood substrate is thus effectively impregnated with the
mix composition in this process. The impregnation process
may be conducted at room temperature or at elevated tem
that is capable of undergoing free radical coupling reaction, 35 peratures. The mix composition may further include water,
polymerization, and/or crosslinking reactions. Unsaturated especially when the polyol and crosslinking agent chosen are
polycarboxylic acids such as maleic acid and unsaturated water soluble or water dispersible. Water can facilitate the
fatty acid having at least 2 carboxylic acid groups, for migration of the mix composition into the interior voids of the
example, can react with the hydroxyl groups of maltodextrins wood substrate. An organic solvent may also be used in place
to form a polyester. The resulting polyester may be further 40 of or in addition to water in the mix composition. Examples of
crosslinked by causing the vinyl groups of the unsaturated organic solvents may include methanol, ethanol, acetone,
acid to couple with each other via heating, oxidation, high glycols, glyco-ethers, glyco-esters, and the like. The mix
energy irradiation or other reaction conditions. A free radical composition may partially ?ll or completely ?ll the voids in
initiator may be included in the mix composition to initiate the wood substrate depending on the particular wood struc
the crosslinking and/or polymerization reaction of the vinyl 45 ture and desired level of treatment.
groups. Examples of a free radical initiator may include After impregnation into the wood substrate, the polyol and
AIBN (2,2'-azobisisotyronitrile), acetyl peroxide, benzyl per crosslinking agent in the mix composition are caused to react
oxide, and sodium persulfate. A metal catalyst or oxidizing with each other to form a substantially insoluble product. To
agent (such as oxygen) may be used to facilitate the reaction facilitate such a reaction, the impregnated wood substrate
of the vinyl group. Organic metal salts of lead, cobalt, zirco 50 may be subjected to a temperature from ambient temperature
nium, zinc, calcium, and iron, for examples, can be used to to about 150 C. Other temperature ranges such as 40-105o
catalyze the oxidative crosslinking of the vinyl group. High C., and about 55-100o C. may also be used to cause an
energy irradiation may include UV (ultraviolet), electron effective reaction between the polyol and the crosslinking
beam, y-ray and ultrasonic radiations. agent. The mix composition inside the wood substrate may be
The polyol and the crosslinking agent may be mixed 55 allowed to react for minutes up to days depending on the
together to form a mix composition. The mix composition dimension of the wood and the speci?c polyol/crosslinking
may further include water or organic solvents. The polyol and agent combination. The wood may also be further dried to a
the crosslinking agent may be included in the mix composi desired moisture level. The crosslinking reaction may be car
tion such that the molar ratio of the carboxylic acid group in ried out in a conventional or high temperature wood season
the crosslinking agent to the hydroxyl group in the polyol is at 60 ing kiln, or in a hot pressing process of laminating impreg
least 1:10. Ratios ranged from 1:10 to 30:1, or 1:5 to 30:1, nated veneers to another substrate, for example. Hot-pressing
may be used accordingly. Effective reactions can take place may also be used to bind impregnated or treated wood sub
within the above ranges, yielding suf?cient amounts of strates together. The polyol and crosslinking agent react with
insoluble reaction product for desired treatment effects of the each other readily under the conditions described above. A
wood substrate. Various combinations of polyols and 65 wide range of carboxylic acid group to hydroxyl group ratios
crosslinking agents can be used to form the mix formulation. (1 : 10 to 30: 1) may be used to achieve effective crosslinking
A polyol having at least 3, 5, 10, 20, 30, 40, 50, or 60 hydroxyl reaction to form insoluble polymer products inside the wood
 US 8,945,706 B2
5 6
voids. In addition, effective level of reactions can be achieved an insoluble crosslinked product, the synergistic components
without having to remove excessive amount of water as would are substantially ?xed into the wood substrate. Coordinating
be required for a conventional polyester polymerization. metal compounds, such as organic and inorganic compounds
As an illustration, a chemical reaction between a polyol of titanium, tin, zinc, antimony, copper, and zirconium, can
having plurality of hydroxyl groups and a crosslinking agent also improve the reaction ef?ciency of the mix composition
when incorporated as a synergistic component. Examples of
having 3 carboxylic acid groups per molecule, for an wood preservatives may include commercially available
example, is shown in the following chemical reaction organic and inorganic wood preservative systems, silver, cop
scheme. The reaction yields a crosslinked polymer having per and zinc compounds, sorbic acid, boric acid and their
ester linkages and a by-product water. salts. Flame retardants may include ammonium phosphate,
aluminum oxide, antimony oxide, magnesium oxide, pen
taerythritol, nitrogen containing compounds such as
on on HOOC melamine, urea, dicyanodiamide, and their derivatives or
HO OH coon salts. Various dyes and pigments may be incorporated into the
+ >
on mix composition to provide desirable color to the wood sub
coon strate. Water and UV protectors may include any known
on waxes, silicones, ?uorocarbons, UV absorbers, UV inhibi
no tors, free radical scavengers, and antioxidants. Various metal
O 000 salts, oxides, nanoparticles and hydroxides, when incorpo
o rated into the mix composition, are effective in improving the
c coon 20 hardness and abrasion resistance of the crosslinked polyester
reaction product and the treated wood substrate. Examples of
metal salts may include calcium formate, acetate, oxide,
hydroxide, carbonate, citrate; magnesium oxide, formate,
acetate, citrate; zinc acetate, citrate, zinc oxide, zirconium
25 carbonate, titanium alkoxide, organotin compounds, and the
like. The term nanoparticle is herein referred to as any
particulate materials having a dimension between about 1
nanometer to about 100 nanometers. The nanoparticle may be
The polyol and/or the crosslinking agent may further incorporated into the mix composition as a dispersion or
include a vinyl group in their chemical structures. Further 30 suspension. Due to their small sizes, the nanoparticle can be
more, a vinyl monomer, oligomer or polymer may be added to effectively carried into the voids in the wood substrate by the
the mix composition. After impregnation of the mix compo mix composition in an impregnation process. The nanopar
sition into a wood substrate, the vinyl group in the mix com ticle thus is intimately embedded into the crosslinked poly
position may be caused to react with each other or with other mer product to provide a reinforcing effect. Nanoparticles
reactive groups in the mix composition to form additional 35 and nanoparticle dispersions may include nanoparticles of
crosslinkages or to further increase the molecular weight of carbon black, silica, alumina, zirconium oxide, titanium
the reaction product. The reaction of vinyl groups may oxide, and antimony oxides.
include free radical polymerization, free radical coupling, Any combinations of wood substrate, mix composition
oxidative coupling, or other addition reactions. The reaction comprising any polyol and crosslinking agent, and wood
may be initiated or facilitated by heating and/ or high energy 40 treatment process may be used.
irradiation. Maleic acid, for example, may be used as a The treatment composition and treated wood products
crosslinking agent. The carboxylic acid groups in maleic acid according to this invention may be used in various products
can react with the hydroxyl groups of the polyol to form a such as wood veneer, wood ?oor, interior and exterior wood
crosslinked polyester, while the vinyl group in the maleic acid furniture, particle boards, plywood and wood laminates.
can undergo a free radical coupling reaction to further 45
crosslink the polyester. Additionally, a vinyl monomer or EXAMPLE 1
polymer may be included in the mix composition. The vinyl
monomer and/ or polymer may copolymerize or co-crosslink 5.0 kg butanetetracarboxylic acid, 20.0 kg citric acid and
with the maleic acid vinyl group. 15.6 kg maltodextrin are mixed in 80.0 kg of water until the
The mix composition may comprise more than one polyol 50 solution becomes clear to form a mix composition. A few
and more than one crosslinking agent. The mix composition solid Aspen wood blocks are placed in an autoclave, and
may also include other synergistic components such as poly evacuated to about 80% vacuum. The mix composition is then
acrylates and vinyl polymers, especially polyacrylate or vinyl transferred into the autoclave. When the autoclave is ?lled
polymers synthesized using acrylic acid or methacrylic acid with the mix composition liquid, an elevated pressure is
as a co-monomer. Examples of polyacrylate and vinyl poly 55 applied to the system for about 3 hours. The impregnated
mers may include copolymers produced from at least two of wood blocks are allowed to dry in an oven heated at 100 C.
ethylene, vinyl acetate, vinyl alcohol, vinyl chloride, for about 24 hours to allow the mix composition to react to
vinylidene chloride, methyl methacrylate, butyl acrylate, form a crosslinked polymer. The resulting treated wood has a
ethyl acrylate, acrylic acid, methacrylic acid, maleic acid, speci?c density of about 0.6 gram/milliliter comparing to
styrene, and the like. 60 about 0.32 gram/milliliter of the corresponding untreated
Other synergistic additives that may be included in the mix wood. The treated wood exhibits improved mechanical prop
composition may include preservatives, insecticides, ?ame erties.
retardants, wood colorants, water and UV protectors, nano
particles and metal compounds. The synergistic components EXAMPLE 2
can be readily incorporated into the low viscosity mix com 65
position, and be carried into the voids of wood substrate. After 5 kg butanetetracarboxylic acid, 20 kg citric acid, 1 kg
the polyol and crosslinking agent are caused to react and form itaconic acid, 18 kg maltodextrin, and 5 kg of a 20% by weight
 US 8,945,706 B2
7 8
aqueous polyvinyl alcohol 5000 solution are mixed with 0.5 7. A wood product comprises: a wood substrate having
kg Zinc acetate, 0.4 kg boric acid and 80 kg water to form a voids and a polymer composition disposed at least partially
mix composition. A few solid radiate pine wood blocks are inside said voids; said polymer composition consisting essen
placed in an autoclave at about 80% vacuum. The mix com tially of a reaction product of at least a polyol comprising
position is then transferred into the autoclave. When the auto maltodextrin having a dextrose equivalent value between 2
clave is ?lled with the mix composition liquid, an elevated and 12 and at least a crosslinking agent having at least 2
pressure is applied to the system for about 3 hours. The carboxylic acid groups per molecule and optionally sorbic
impregnated wood blocks are allowed to dry and heated in an acid orboric acid, optionally a metal compound selected from
oven at about 100 C. for about 24 hours. The resulting treated the group consisting of Zinc acetate, Zinc citrate, calcium
wood has a speci?c density of about 0.7 gram/milliliter com formate, calcium acetate, magnesium acetate, magnesium
paring to about 0.45 gram/milliliter of the corresponding citrate, magnesium formate, and Zirconium carbonate, and
untreated wood. Janka hardness of the treated wood reaches optionally at least one of ammonium phosphate, aluminum
about 1600 pound-force. oxide, magnesium oxide, melamine, dicyanodiamide, and
The above description of embodiments of the invention is urea; wherein said crosslinking agent is cis- or trans-butene
merely exemplary in nature and, thus, variations thereof are dioic acid, EDTA, citric acid, citraconic acid, butanetetracar
not to be regarded as a departure from the spirit and scope of boxylic acid (BTCA), maleic acid, maleic anhydride, tartaric
the invention. acid, succinic acid, mesaconic acid, unsaturated fatty acid,
What is claimed is: itaconic acid or any mixtures thereof; and wherein said wood
1. A polymer composition suitable for wood treatment or substrate has been impregnated with said polyol and said
binding consists essentially of a reaction product of at least a 20 crosslinking agent, and said polymer composition is formed
polyol and at least a crosslinking agent and a solvent; said from the polyol and the crosslinking agent after the impreg
crosslinking agent having at least 2 carboxylic acid groups nation.
per molecule and said polyol consists of a maltodextrin or a 8. The wood product as set forth in claim 7, wherein said
derivative of maltodextrin which have a dextrose equivalent wood substrate is one of soft wood, hard wood, Radiata Pine,
value between 2 and 12, wherein said crosslinking agent is 25 Scots Pine, Red Pine, Yellow Pine, Maple, Alder, Birch,
cis- or trans-butenedioic acid, EDTA (ethylenediamine-tet Aspen, Salsa wood, Beech, corn stalk, bamboo, straw stalks,
sugar cane bagasse or any combinations thereof.
raacetic acid), citric acid, citraconic acid, butanetetracar
9. The wood product as set forth in claim 7, wherein said
boxylic acid (BTCA), tartaric acid, succinic acid, maleic acid,
maleic anhydride, mesaconic acid, fatty acids, unsaturated polymer composition is disposed inside said voids.
fatty acid, itaconic acid, or any mixtures thereof. 30 10. The wood product as set forth in claim 7, wherein said
2. A process of wood treatment comprising: polymer composition covalently bonds to at least a portion of
a. Providing a wood substrate having voids; said wood substrate through a chemical reaction between said
b. lmpregnating said wood substrate with the polymer crosslinking agent and said wood substrate.
composition as set forth in claim 1 such that at least a 11. The wood product as set forth in claim 7, wherein the
portion of said voids are at least partially ?lled with said 35 molar ratio of the carboxylic acid groups in said crosslinking
mix composition; and agent to the hydroxyl groups in said polyol is 1:10 or greater.
c. Causing a chemical reaction between said polyol and 12. The wood product as set forth in claim 7, wherein at
said crosslinking agent to form a water insoluble poly least one of said polyol and said crosslinking agent comprises
mer.
a vinyl group that is capable of undergoing a polymerization
3. The process as set forth in claim 2, wherein said impreg 40 or a crosslinking reaction in the presence of heat, free radical
nating comprises exposing said wood substrate to vacuum; initiator, oxidizer or high energy irradiation.
contacting said wood substrate with said polymer composi 13. The wood product as set forth in claim 7, wherein said
tion, and subsequently elevating pressure to cause said poly polyol has between 3 and 1000 hydroxyl groups per molecule
mer composition to migrate into said voids. or a dextrose equivalent between 2 and 12, and said crosslink
4. The process as set forth in claim 2, wherein said chemi 45 ing agent has at least 3 carboxylic acid groups per molecule.
cal reaction is effectuated by heating, high energy irradiation, 14. The wood product as set forth in claim 7, wherein said
hot pressing, or any combination thereof. crosslinking agent is a mixture of a ?rst component and a
5. The process as set forth in claim 2, wherein said polyol second component, the ?rst component is at least one of
has about 3 to 1000 hydroxyl groups per molecule and said EDTA, citric acid, citraconic acid, butanetetracarboxylic acid
crosslinking agent has at least 3 carboxylic acid groups per 50 (BTCA), tartaric acid, succinic acid, mesaconic acid, and the
molecule. second component is at least one of cis- or trans-butenedioic
6. The polymer composition as set forth in claim 1, wherein acid, maleic acid, maleic anhydride, fatty acids, unsaturated
said crosslinking agent is a mixture of at least two of cis- or fatty acid, and itaconic acid.
15. The wood product as set forth in claim 7, wherein the
trans-butenedioic acid, EDTA, citric acid, citraconic acid,
butanetetracarboxylic acid (BTCA), tartaric acid, succinic 55 crosslinking agent is a mixture of butanetetracarboxylic acid
and citric acid.
acid, maleic acid, maleic anhydride, mesaconic acid, fatty
acids, unsaturated fatty acid, and itaconic acid.