Discloses compositions of urea dissolved in aqueous, polymerizable phenolic resole resins, wood-product laminated composite products produced with such resins, with or without the urea, and methods for the production of wood-product laminated composites with such resins. The resins contain the alkaline polymerization product of (a) formaldehyde polymerized with phenol and aliphatic hydrocarbylphenol or (b) aliphatic hydrocarbylphenol dissolved in the resin containing the polymerization product of phenol and formaldehyde, wherein the hydrocarbylphenol has from 9 to 17 carbon atoms in the hydrocarbyl group and the quantity of hydrocarbylphenol is from about 0.2% to 5% based on the weight of the aqueous resole resin. Wood-product laminate composites bound with the above resole resin, after curing, exhibit unexpectedly low water absorption, good internal bond strength and reduced thickness swell properties.

BACKGROUND OF THE INVENTION 
This invention relates to phenolic resole resins which contain small 
quantities of aliphatic hydrocarbylphenol having from 9 to 17 carbon atoms 
in the hydrocarbyl group, their manufacture and use for making 
wood-product laminated composites and such composites manufactured from 
the resins. The resins will generally contain urea in a quantity 
sufficient to lower the viscosity of the resin and to scavenge 
formaldehyde. By the term "hydrocarbyl" we mean a monovalent group 
containing only the elements of hydrogen and carbon. 
It has been found that from about 0.2 to about 5% of an aliphatic 
hydrocarbylphenol having from 9 to 17 carbon atoms in the hydrocarbyl 
group when polymerized with formaldehyde and phenol in an aqueous alkaline 
medium to form a phenolic resole resin or when post-added to an alkaline 
phenol-formaldehyde aqueous resin solution provides adhesives for the 
manufacture of wood-product laminated composites wherein the resulting 
composites have improved internal bond strengths, durability, decreased 
water absorption and thickness swell properties in comparison with 
phenolic resole resins which do not contain the specified 
hydrocarbylphenols in the indicated quantities of this invention. 
Phenol-formaldehyde resole resins represent a large portion of the adhesive 
binders used in the manufacture of wood-product laminated composites. 
Phenol-formaldehyde resole resins are frequently used as laminate binders 
in the manufacture of wood-product laminated composites such as veneer 
products, e.g., plywood and LVL (laminated veneer lumber), as well as 
wood-particle composites, e.g., particleboard, waferboard, and OSB 
(oriented strand-board). In most cases, the laminated composites are in 
the form of panels. 
Liquid phenolic resole resins bind as thermosets which are typically cured 
via hot pressing. Hot pressing is done under pressure with heat supplied 
via platens heated by hot oil, electricity, or steam. Phenolic thermoset 
curing methods include RF-curing (radio frequency) and steam injection 
pressing. 
Traditionally, liquid phenol-formaldehyde resole resins constituted the 
predominant type of adhesive used as wood-product binders for products 
such as OSB and plywood. Recently, isocyanates such as PMDI 
(poly(methylenediphenyl-4,4'-diisocyanate)) have come into use as 
wood-product laminate composite adhesives for manufactured products. 
Isocyanates offer faster cure speeds, reduced tendency for water 
absorption, and lower overall manufacturing costs in comparison with 
phenolic resole resins. Also, less of the isocyanate is required. 
A draw-back of wood product laminated composites bound with isocyanates is 
that they are prone to degradation because of lower rigidity and moisture 
induced internal panel stresses as well as health risks in the mill. This 
is particularly the case with non-veneer laminated composites. Isocyanates 
are especially prone to this form of degradation since they lack the 
durability of three-dimensional network crosslinking density inherent with 
phenol-formaldehyde resins. In order to further improve liquid phenolic 
resins and make them more competitive against isocyanates we began 
researching ways to improve such resins. We have found that the 
incorporation of certain small amounts of hydrocarbylphenol having from 9 
to 17 carbon atoms in the hydrocarbyl group when polymerized with aldehyde 
and phenol in the manufacture of the resin polymer or when added to a 
preformed phenol-aldehyde resin which is eventually coated on wood 
products and bound under heat and pressure to form composite panels impart 
improved properties to the wood-product laminated composites. 
The prior art shows the use of aldehydes reacted with various phenolics 
such as phenol, naphthol, and various hydrocarbylphenols and mixtures 
thereof for use in the manufacture of resole resins as well as the use of 
certain of the resole resins for the manufacture of composite panels and 
other materials. The prior art also shows the use of urea dissolved in 
certain resole resins for the manufacture of composite panels. However, 
the prior art does not show or suggest that the small quantities of the 
aliphatic hydrocarbylphenols used in this invention when polymerized with 
phenol and an aldehyde as part of the manufacture of a 
phenol-formaldehyde-hydrocarbylphenol resole resin or when such 
hydrocarbylphenols are simply dissolved in a preformed phenol-aldehyde 
resole resin provide superior and unexpected properties in the manufacture 
of composite panels, with or without urea. 
BRIEF SUMMARY OF THE INVENTION 
In one aspect, this invention relates to curable phenolic resole resins 
prepared by polymerizing phenol, aldehyde and aliphatic hydrocarbylphenol 
in an alkaline aqueous medium. The resin containing the polymerized 
phenol, aldehyde and aliphatic hydrocarbylphenol will further contain from 
about 0.2% to 18% by weight of urea dissolved therein, The quantity of 
polymerized hydrocarbylphenol is from 0.2% to 5% by weight of the aqueous 
resin wherein the hydrocarbylphenol has from 9 to 17 carbon atoms in the 
hydrocarbyl group. 
In still another aspect of this invention, an aliphatic hydrocarbylphenol 
having 9 to 17 carbon atoms in the hydrocarbyl group is added to a curable 
aqueous, alkaline phenolic resole resin. The quantity of 
hydrocarbylphenol, based on the weight of the resin which includes 
hydrocarbylphenol will be from about 0.2% to 5%. Additionally the resin 
will include from about 0.2% to 18% by weight of urea dissolved therein 
either before or after the addition of the hydrocarbylphenol. 
In yet another aspect of this invention, the above novel phenolic resins 
are used as binding adhesives, with or without dissolving urea in the 
resin, for the manufacture of wood-product laminated composites such as 
strand-board and plywood. 
In a further aspect of the invention, wood-product laminated composites are 
prepared by coating wood components with the above curable phenolic resole 
resins, with or without urea dissolved therein, and then bonding the 
components under heat and pressure. 
Other aspects of this invention are concerned with methods for manufacture 
of the phenolic resole resins of this invention as well as methods for the 
manufacture of wood-product composites such as strand-board and plywood 
bound with the novel phenolic resole resin. 
DETAILED DESCRIPTION OF THE INVENTION 
The Phenolic Components 
The first phenolic component used in the synthesis of the phenolic resole 
resins of this invention is phenol. The second phenolic component is an 
aliphatic hydrocarbylphenol wherein the hydrocarbyl group has from 9 to 17 
carbon atoms, preferably 10 to 17 carbon atoms and particularly 12 to 15 
carbon atoms. The hydrocarbyl group can be branched chain, straight chain, 
or cycloaliphatic. The hydrocarbylphenols having 10 or more carbon atoms 
give substantially better results for use as bonding agent for wood 
product laminate composites as compared to nonylphenols. Hydrocarbylphenol 
reactants having a straight chain hydrocarbyl group such as alkyl or 
straight chain mono-, di-, or triethylenically unsaturated hydrocarbyl 
groups and mixtures thereof are preferred. 
The hydrocarbyl group can be in the para-, ortho-, and preferably in the 
meta- position on the phenolic nucleus. The hydrocarbyl group can be a 
saturated hydrocarbyl group, i.e., alkyl or the hydrocarbyl group can be 
an olefinic mono- or poly-unsaturated hydrocarbyl group. Illustrative of 
the saturated aliphatic hydrocarbylphenols there can broadly be mentioned: 
nonylphenol, decylphenol, undecylphenol, dodecylphenol, tridecylphenol, 
tetradecylphenol, pentadecylphenol, hexadecylphenol and heptadecylphenol. 
Illustrative of specific hydrocarbylphenols there can be mentioned 
p-nonylphenol, o-decylphenol, m-undecylphenol, o-dodecylphenol, 
m-tridecylphenol, p-tetradecylphenol, m-pentadecylphenol, 
o-pentadecylphenol, p-pentadecylphenol, o-hexadecylphenol, and 
p-heptadecylphenol, mixtures of the foregoing and cashew nut shell liquid. 
Various ethylenic unsaturated hydrocarbyl groups can be attached to the 
phenol nucleus but preferably the unsaturated hydrocarbylphenols are that 
of cashew nut shell liquid (CNSL). CNSL is obtained by special heat 
treatment and decarboxylation of cashew nut shells. CNSL is a mixture of 
phenolic compounds with a major amount being straight chain monofunctional 
(monohydroxylic) meta substituted hydrocarbylphenols with the hydrocarbyl 
group having 15 carbon atoms with ethylenic unsaturation such as that of 
cardinol triene, cardinol diene, and cardinol monoene. CNSL also contains 
about 12% of difunctional (dihydroxylic) phenolic such as cardol diene, 
cardol triene, and cardol monoene. Smaller quantities of additional mono- 
or difunctional mononuclear phenols, mostly with a hydrocarbyl in the 
meta-position are also present. 
The hydrocarbylphenols of this invention can be represented by the formula 
##STR1## 
(C.sub.6 H.sub.4 OHR) wherein R is hydrocarbyl of 9 to 17 carbon atoms, 
e.g., dodecyl, pentadecyl, and the like. 
The quantity of the aliphatic hydrocarbylphenol used in the manufacture of 
the phenol-aldehyde-hydrocarbylphenol resole resin as well as for the 
addition of hydrocarbylphenol to a preformed phenol-aldehyde resole resin 
is about 0.2 to 5%, preferably 0.2 to 3% and particularly 0.4 to 2% based 
on the weight of the aqueous resin medium which includes the 
hydrocarbylphenol. Quantities of the hydrocarbylphenol of less than about 
0.2% based on the weight of the aqueous medium have minimal to no 
effectiveness whereas quantities substantially greater than about 3% do 
not appear to impart significant additional desirable properties. 
Additionally, quantities of the hydrocarbylphenol greater than about 5% by 
weight of the aqueous resin medium are difficult to dissolve and can form 
suspensions, including gummy dispersions which are deleterious for use in 
the manufacture of wood product laminated composites. Additionally, when 
quantities of greater than about 5% are used for manufacture of the 
aldehyde-phenol-hydrocarbylphenol polymer or by simply adding such 
quantities to a preformed phenol-aldehyde resole resin and the resin is 
subsequently stored at low temperature, which is conventional with 
phenolic resole resins, there is a tendency for unstable suspensions and 
gummy deposits to be formed in the resin. Generally, smaller quantities of 
hydrocarbylphenol are required to obtain a product of improved properties 
as the number of carbons in the hydrocarbyl group increase from 9 to 17 
carbon atoms. 
Although post addition of hydrocarbylphenol to a preformed phenol-aldehyde 
resole resin provides panels with desirable properties, an advantage of 
polymerizing the hydrocarbylphenol initially with phenol and aldehyde is 
that post-addition of the free hydrocarbylphenol provides environmentally 
undesirable volatile organic components to the resin, particularly on 
curing, and furthermore the hydrocarbylphenols have topical toxicity and 
have recently been added to the list of potential endocrine disrupter 
suspects. 
The 0.2 to 5% range of hydrocarbylphenol polymerized or dissolved as part 
of the resole resin converts to about 0.5% to 20% by weight of 
hydrocarbylphenol based on the total weight of polymerized phenol and 
hydrocarbylphenol or based on the total weight of polymerized phenol and 
dissolved hydrocarbylphenol in the resin, generally not more than 15% and 
preferably from about 1.2 to 8% by weight of hydrocarbylphenol based on 
both the phenol and hydrocarbylphenol. The amount of free phenol in the 
resin solution, e.g. when used as a binder, is generally less than 1% and 
preferably less than 0.5% by weight of the resin. The free aldehyde, e.g., 
formaldehyde, in the resin will typically be less than about 0.3% and 
preferably less than about 0.1% by weight of the resin. 
The Aldehyde. 
The aldehyde reacted with the phenolic components can include any of the 
aldehydes heretofore employed in the formation of phenolic resins such as 
formaldehyde, acetaldehyde, propionaldehyde, furaldehyde and benzaldehyde. 
In general, the aldehydes contemplated have the formula R.sup.1 CHO 
wherein R.sup.1 is hydrogen or a hydrocarbyl group of 1 to 8 carbon atoms. 
The preferred aldehyde is formaldehyde or wherein only a portion, such as 
less than 25%, of the formaldehyde is substituted with another aldehyde. 
Aldehyde donors such as formalin, para formaldehyde, 
alpha-polyoxymethylene, hexamethylenetetramine, etc. can also be used as 
the aldehyde. 
The Resole Resin. 
By the term "resole" we mean a polymer obtained by alkaline reaction of 
phenol and aldehyde wherein the mole ratio of phenolic component to 
aldehyde varies from about 1:1 to 1:3. The phenolic component in this mole 
ratio includes hydrocarbylphenol in addition to phenol. 
The reaction in the manufacture of the phenolic resole resins of this 
invention with aldehyde and the two phenolic components takes place in an 
aqueous alkaline medium at elevated temperatures, e.g., 60.degree. C. to 
105.degree. C. or even higher if the reaction vessel is pressurized. The 
alkalinity can be provided by the presence of alkaline materials such as 
sodium hydroxide, potassium hydroxide, ammonia, sodium sulfite and the 
like. When the hydrocarbylphenol is polymerized together with phenol and 
formaldehyde in making the resin, such process is referred to herein as 
having the hydrocarbylphenol cooked in the resin. 
The resole resins of this invention are referred to as aqueous solutions 
since the solids are dissolved in water or water together with minor 
amounts, e.g., less than about 3% or 9% by weight of a non-reactive 
solvent. Some of the resins of this invention form clear solutions whereas 
others appear to have some turbidity. 
A typical resin containing the phenol-aldehyde-hydrocarbylphenol polymer is 
made by charging a reactor with phenol, an aliphatic hydrocarbylphenol 
having from 9 to 17 carbon atoms in the hydrocarbyl group, water and 
caustic soda (50% NaOH) to form an aqueous alkaline solution of the phenol 
and hydrocarbylphenol, followed by the slow addition of formaldehyde. 
Additional caustic soda is generally added after the formaldehyde has 
reacted. The resulting reaction mixture is then heated under vacuum and 
condensed to the desired end-point. The extent of reaction (and subsequent 
molecular weight) is typically monitored by refractive index (RI) or by 
Gardner tube viscosity. When the desired extent of reaction is attained, 
the reaction mixture is cooled and generally urea is added and dissolved 
in the resin as a thinning agent and free formaldehyde scavenger. 
A typical resin of this invention wherein the hydrocarbylphenol is 
post-added to a preformed phenol-aldehyde resin is simply prepared by 
dissolving the hydrocarbylphenol in an alkaline phenol-aldehyde resin. The 
phenol-aldehyde resin is prepared in a manner similar to that of the 
terpolymerized resin containing hydrocarbylphenol with the omission of the 
hydrocarbylphenol. 
The resins of this invention have an alkalinity content, i.e., contain a 
base, in the range of 0.5% to about 15%, and preferably 1% to 12%, based 
on the weight of the resin solution, when the base is sodium hydroxide. 
Thus, the term "alkalinity content" or simply "alkalinity" is based on 
sodium hydroxide solids. When a different base is used, the alkalinity 
content is proportionally equivalent on a molar weight basis. For example, 
to attain a 4% sodium hydroxide equivalent weight alkalinity content, it 
requires 4 grams of sodium hydroxide in 100 grams of resin solution, but 
5.61 grams of potassium hydroxide in 100 grams of the resin are required 
to attain the same alkalinity content. Additional base can be added to a 
resole resin after manufacture in order to bring it to the desired 
alkalinity content, target viscosity, or both. The pH of the resole resin 
will be at above 8, preferably above 9, and particularly above 10. 
The resins of this invention will have a resin pan solids content of about 
20% to 75% by weight and preferably about 45% to 60%. The water content of 
the resin at the time of manufacture of the resin will generally vary from 
about 80% to 25% and preferably from about 40% to 55% by weight of the 
entire aqueous alkaline resin. Generally, the viscosity should be such as 
to permit the solution to be sprayed on the cellulosic components such as 
flakes or strands or to otherwise be applied to the components such as 
veneer. Thus, the viscosity of the resin will generally vary from about 50 
to about 1,000 centipoise at 25.degree. C. as determined by a Brookfield 
RVF viscosimeter with a number 2 spindle at 20 revolutions per minute at 
25.degree. C. and preferably from about 100 to 300 cps at 25.degree. C. 
when used with particulate components such as wood strands. 
The number average molecular weight of the resins of this invention is 
preferably greater than about 700, more preferably greater than about 
1,000, and most preferably within the range of about 1,000 to 2,200 for 
use with wood particle panels such as particleboard and OSB with a special 
preference for weights between about 1,000 and 1,888. The resins used with 
plywood should also have a number average molecular weight in excess of 
about 700, preferably weights between about 1350 and 3,000, most 
preferably between about 1,500 and 2,500. 
Although liquid resins are preferred for use in the manufacture of the 
laminated composite products of this invention, the resins can be spray 
dried and used as powders by conventional techniques, e.g. see U.S. Pat. 
No. 5,047,275 of Sep. 10, 1991 to S. Chiu which is incorporated herein by 
reference in its entirety. 
The resins of this invention may be used as is or may be extended by mixing 
the resin with extenders such as flour or other suitable fillers. The "as 
is" resins are typically used for composition panels while the extended 
resins are used for plywood. 
Additives 
Suitable additives can be used in the resin for coating the raw wood 
components. Thus, from 0.25 to 3% by weight, based on the weight of the 
oven dry wood of the board product, of molten slack wax as well as 
emulsified wax can be used. Still further, from 5% to 20% by weight, based 
on the weight of the oven dry wood in the board product, of a suitable 
plasticizer may be included. Suitable plasticizers include glycol esters, 
glycerine esters, phosphate esters and the like. 
Thickeners such as the various gums, starches, protein materials and clays 
may be used together with the resins. The resins can have additives 
dissolved therein. Illustratively urea is often dissolved in the resin in 
order to decrease the resin viscosity. When urea is used, its quantity can 
vary over a broad range such as from about 0.2% to 18% based on the weight 
of the resin solution containing the urea, preferably from about 2% to 14% 
thereof and particularly from about 8 to 12% thereof. In addition to 
reducing viscosity, the urea also acts as a formaldehyde scavenger for the 
resin. 
Anti-foam agents can also be helpful for use in the manufacture of the 
resins of this invention. Illustrative of such anti-foam agents there can 
be mentioned silicone anti-foam agent designated as Q2-3183A of 
Dow-Corning of Midland Mich.; and Colloid 581B and Colloid 999 which are 
products of Rhone-Poulanc having an office at Prospect Plains Road, 
Cranberry, N.J. 08512-7500. When anti-foam agents are used the quantity 
thereof will vary from about 0.001% to 0.3%, depending on the type of 
anti-foam agent used, preferably about 0.001 to 0.1% and particularly 
about 0.002 to 0.05% based on the weight of aqueous resin including the 
anti-foam agent. Smaller quantities of anti-foam agent are used with the 
more efficient anti-foam agents such as the silicones. 
Apart from the small quantities of anti-foam agents, other emulsifiers are 
preferably avoided since they adversely affect the resin moisture 
responses and bonding properties. Thus, the compositions of this invention 
will preferably be substantially free of emulsifiers. By substantially 
free we mean the use of no more than about 1%, preferably no more than 
about 0.5% and particularly no more than about 0.2% based on the weight of 
the resin, including the emulsifier. Other components such as fillers 
and/or extenders may also be added to the resole resins of this invention. 
The curing rate of the resin may be accelerated by contacting the resin or 
wood components with a curing agent. The curing agent may be a 
conventional curing accelerator such as a carboxylic acid ester, a 
lactone, an organic carbonate or a resorcinol-glutaraldehyde resin such as 
is disclosed in U.S. Pat. No. 5,498,647 of Mar. 12, 1996 to D. Shiau et 
al. The amount of curing agent can vary over a wide range such as that of 
about 1% to 20% of the resin solids. 
Application of the Resinous Adhesive 
As is conventional in the art, the adhesive, i.e. resin together with any 
additives is applied to wood product fibers, flakes, chips, strands and 
the like by various spraying techniques whereas it is generally applied to 
veneers by coaters. Resin applied to the wood components is referred to 
herein as a coating even though it may be in the form of small resin 
particles such as atomized particles which do not form a continuous 
coating. 
The range of resin solids in the resole resin before curing which are 
applied to the wood components can vary from about 1% to 15% and 
preferably 2% to 8% by weight of the wood components on dry finished panel 
weight depending of the quality of the panel product desired. 
Hot pressing conditions for the panels utilizing the resinous adhesive of 
this invention will depend on the thickness of the board, the type of 
board, as well as on the resin characteristics. Generally, the platen 
temperatures can vary from about 240.degree. F. (115.degree. C.) to 
450.degree. F. (232.degree. C.) with applied pressures which can range up 
to about 1200 psi for about 2 to 10 minutes. 
The Wood Components 
The wood components which are the basic raw materials for the wood-product 
laminate composites which can be made with the adhesives of this invention 
may be derived from various species of wood in the form of wood fibers, 
chips, shavings, strands, flakes, particles and veneers. These materials 
which are used to prepare the laminated composites are referred to 
generally herein as wood components. The manufactured products include 
hardboard, particleboard, fiberboard, waferboard, strand-board and the 
like as well as plywood, and LVL. The internal bond strength of these 
products will be at least about 30 pounds per square inch (psi). 
Methods for making plywood, cellulosic board, oriented strand-board (OSB) 
and the like are described in prior art as for instance in U.S. Pat. Nos. 
4,758,478 to Daisy et al and 4,961,795 to Detlefsen et al., which patents 
are incorporated herein by reference in their entirety. For example, when 
producing a composition panel such as particle board or oriented 
strand-board by a mat process, wood flakes, strands or particles can be 
sprayed with a solution of the resin of this invention. The sprayed pieces 
of wood components may be passed through a forming head to make a mat. Hot 
pressing conditions for the mat will depend upon the target thickness for 
the board product as well as on the characteristic of the binder. 
This invention is particularly useful in the manufacture of plywood and 
oriented strand-board. Plywood is composed of a multiple layer of wood 
veneers. The veneers are usually arranged so that the wood grain direction 
is perpendicular in adjacent veneers. 
The plywood process requires straight logs cut to length, and conditioned 
in heated vats containing water and surfactants to increase the heating 
efficiency of the vats. The heated logs are then "peeled" wherein a veneer 
of predetermined thickness is removed continuously until the log diameter 
is reduced to a certain point, usually 5-8 inches (12.7-20.3 cm.) The 
veneer is than clipped into strips, sorted and dried to a moisture content 
of 15% or less. 
After drying, the veneers are graded and assembled into plywood panels. The 
adhesive is applied to the veneers at this stage of manufacture. The 
adhesive is usually composed of the liquid resin and fillers that include 
inorganic and organic flours, such as wheat flours, wood flours, and 
clays. The adhesives are specially formulated for individual user mills 
depending on manufacturing equipment, type of wood to be glued, type of 
product to be made, and ambient environment conditions at the time of 
panel manufacture. The adhesive is usually applied to the veneers by roll 
coater, curtain coater, sprayline or foam extruder. The adhesive usually 
contains the resin at a level of 20% to 40% resin solids by weight. The 
adhesive is normally used with spread levels of 50 pounds to 55 pounds 
(27.2-25 Kg) when spread on one side. 
After the adhesive is applied to the wood veneers and the panels are 
assembled, they are consolidated under heat and pressure. This is usually 
done in a steam hot press using platen temperatures of about 
240-350.degree. F. (115-176.5.degree. C.) and pressures of 74-250 pound 
per square inch (5.2-17.6 Kg/sq cm) 
Oriented strand-board or OSB is manufactured by orienting wood strands to 
increase strength and stability whereas waferboard consists of flakes 
randomly oriented and pressed into panels. Oriented strand-board uses wood 
strands longer than they are wide, which makes it possible to orient them 
in a specific direction. Placement and orientation is accomplished 
mechanically, generally through the use of a forming machine. Typically, 
OSB panels have 3 or 5 layers. To optimize panel stiffness, top and bottom 
layers of the panels have strands oriented length-wise. Strands in the 
core layer are oriented randomly or in some cases perpendicular to the 
face orientation. This orientation strategy increases panel stiffness, 
strength, and dimensional stability. Typical OSB process stages are as 
follows: (a) logs are delivered; (b) logs are stored in woodyard; (c) logs 
are soaked in heated vats; (c) logs are debarked; (d) logs are flaked into 
strands and dried to a moisture content of about 1 to 15%; (e) screens are 
used to remove fines; (f) strands are blended with resin and wax with the 
quantity of resin typically being about 2 to 5.5% and the quantity of wax 
being from about 0.5 to 2%, both based on the weight of the dried strands; 
(g) blended strands are dropped into a formline to orient the strands and 
form mats; (h) mats are pressed, typically for about 4 to 7 minutes at a 
temperature of about 240 to 450.degree. F. (115-232.degree. C.) into 23/32 
inch thickness panels; (i) panels are cut to desired dimensions, stacked 
into units and then loaded onto trucks and shipped. 
The most common thicknesses for the OSB panels vary from about 7/16 of an 
inch to 23/32 of an inch (1.1-1.8 cm). The dimensions of the strands used 
in making oriented strand-board typically vary from between a length of 
about 2.5 to 6 inches (0.4 to 15 cm), a thickness of about 0.025 to 0.15 
inches (0.063-0.38 cm) and widths of about 1 to 4 inches (2.54-10.2 cm). 
However, the strand dimensions can vary depending on the contemplated end 
use of the product. Thus, for some applications strands are as much as 12 
inches (30.5 cm) long. 
The invention will be demonstrated by the following examples. In these 
examples and elsewhere through the specification, parts and percentages 
are by weight unless expressly indicated otherwise. Unless indicated 
otherwise, the quantity of the aliphatic hydrocarbylphenol is expressed as 
a percentage based on the weight of the aqueous, alkaline phenolic resole 
resin. The aqueous alkaline phenolic resole resin, also simply referred to 
as the resin or resin solution, includes all of the ingredients in the 
resin such as water, any free phenol or formaldehyde, polymerized 
phenol-formaldehyde, alkalizing agent and the hydrocarbylphenol, the 
phenol-formaldehyde-hydrocarbylphenol and urea when urea is part of the 
resin. Also, the term "resin solids" refers to pan solids according to an 
industry accepted test where one gram of resin is placed in an aluminum 
pan and heated in a forced air oven at 125.degree. C. for one hour and 45 
minutes. 
A large number of variables are involved in the testing of laminate 
composites for bond strength and effects of moisture so that direct 
comparisons are difficult to make from example to example. Nevertheless, 
comparisons can be made within any single example and also the relation of 
test results of the control sample, i.e. resin without polymerized or 
dissolved hydrocarbylphenol, in comparison to test results for other 
samples in various examples can be validly compared. Illustrative of 
variables are: the furnish can be from different sources but even if from 
the same source, the furnish can differ due to the mix of different wood 
species and wood density; constituents in the wood can differ, e.g. a tree 
grown on the shady side of a hill will have different percentages of 
various constituents as compared to a tree grown on the sunny side of the 
hill; the relative humidity may vary from time to time; and the use of 
different operators at different stages of the preparation of samples for 
testing, particularly in the felting operation can produce somewhat 
different results because of varying board density, among other factors. 
While the invention has been described in connection with specific 
embodiments thereof, it will be understood that it is capable of further 
modifications. This application is intended to cover any variations, uses 
or adaptations of the invention following, in general, the principles of 
the invention, and including such departures from the present disclosure 
as come within known and customary practices within the art to which the 
invention pertains.

EXAMPLE 1 
Typical Preparation of the Phenolic Resole Resin of Phenol and 
Hydrocarbylphenol Polymerized with Formaldehyde 
Charge a five liter 3-neck round bottom flask (kettle) with 1185.2 parts of 
phenol, 21.8 parts of 4-dodecylphenol, 50.8 parts of sodium hydroxide, and 
462.5 parts of water. Then begin heating the kettle. When the temperature 
reaches about 60.degree. C. begin slowly charging 492 parts of 
formaldehyde in an aqueous solution into the reaction mixture. The 
formaldehyde solution is preheated to about 50.degree. C. before being 
charged into the reaction mixture. The formaldehyde is charged slowly over 
the course of thirty minutes while maintaining the temperature at 
98.degree. C. After all of the formaldehyde has been added, maintain the 
temperature at about 98.degree. C. such as by ref lux reaching an 
equilibrium between heat and vacuum for ninety minutes. The reaction 
mixture is then cooled to about 94.degree. C. and begin charging 985.8 
parts of additional formaldehyde slowly over the course of thirty minutes 
while maintaining the temperature at 94.degree. C. Cool the reaction 
mixture to 92.degree. C. such as by using vacuum, cold water or removal of 
the heat source and monitor the reaction progress. Condense the mixture to 
Gardner-Holt D-E viscosity. Cool the reaction mixture to 80.degree. C. and 
condense to Gardner-Holt T-U viscosity. Cool the reaction mixture to 
75.degree. C. and condense to Gardner-Holt W-X viscosity. Cool the 
reaction mixture to 72.degree. C. and charge an additional 238.5 parts of 
sodium hydroxide. At 72.degree. C. condense the reaction mixture to 
Gardner-Holt X-Y viscosity. Begin "full cool" of the reaction mixture such 
as by using a water shower over the reaction flask. When the reaction 
mixture cools to 40.degree. C. or below, add 198.9 parts of sodium 
hydroxide. At or below 30.degree. C. add 363.7 parts of urea. All parts 
herein are by weight. The calculated theoretical value of this resin is 
that of: a total of 4,000 parts; F/P ratio of 2.47 to 1; solids of 49.67%; 
alkalinity of 6.10; with 0.6% of 4-dodecylphenol polymerized together with 
phenol and formaldehyde in the resin. 
A typical terpolymerized resin of this invention containing 0.6% of 
4-dodecylphenol will have an alkalinity of 6.31%; free formaldehyde of 
0.08%; fresh viscosity of 280 cps at 25.degree. C.; surface tension of 
32.1 dynes/cm at 25.degree. C.; a boiling water gel of 19 minutes and 18 
seconds; a refractory index of 1.4816 at 25.degree. C. and a number 
average molecular weight of 1333. 
EXAMPLE 2 
The test results for resin performance in the manufacture of the laminated 
composite panels of this invention is obtained by the manufacture of 15 
inch(38 cm) by 15 inch (38 cm) OSB test panels, preferably of three 
quarters of an inch (1.9 cm) thickness. These panels are made using a 
Washington Ironworks hot oil press. The furnish, (wood strands for 
strand-board) is first conditioned to a pre-selected moisture content of 3 
to 4%. Next, the resins are sprayed onto the furnish, following an initial 
treatment with wax. The resin-coated strands are then oriented into a mat, 
placed between 2 caul-plates and hot-pressed with platens heated at about 
400.degree. F. (204.degree. C.) After the boards are made, they are 
allowed to cool for a time, and then are cut-up and tested using ASTM 
standard test method D1037 except that the method was modified to the 
extent of using samples having dimensions of 5 inches (12.7 cm) by 5 
inches (12.7 cm) instead of 6 inches (15.2 cm) by 6 inches (15.2 cm). Some 
erratic results can be obtained in these tests due to the relatively small 
panels, i.e., the 15 inch (38 cm) by 15 inch (38 cm) panels which are then 
cut into the smaller samples and furthermore the preparation of these 
panels involves many physical and some chemical steps. 
In the following Tables 2A, 2B, 2C, 2D, and 2E, the following abbreviations 
have the following meanings: 
"IB" is internal bond strength expressed as pounds per square inch and also 
converted to kilograms per square centimeter. 
"WA" is water absorption as percent change from the samples original 
weight. 
"TS" is thickness swell as percent change from the samples original 
thickness. 
"CON" is a phenol-formaldehyde resole resin suitable for binding laminated 
composites having a formaldehyde to phenol molar ratio of 2.4 and having 
9.1% of urea dissolved therein. Various resins were compared with CON 
resin by reacting a mixture of hydrocarbylphenol and phenol with 
formaldehyde in the same manner as with the preparation of the CON 
(Control) resin which did not contain hydrocarbylphenol. The 
hydrocarbylphenol, in the amounts indicated in the Table, replaced a 
portion, by weight, of the phenol used in the preparation of the CON 
phenol-formaldehyde resin. Phenol, similar to that used to obtain the 
results in these tables was analyzed for any long chain or short chain 
hydrocarbylphenol impurity. A maximum impurity in the phenol of 0.15% was 
found and such impurity was predominantly that of o-cresol. Therefore, 
hydrocarbylphenols other than O-cresol are not present in any significant 
level. 
"A-DDP" is a resin having substantially the same composition and method of 
manufacture as resin CON except that a portion of the phenol used in its 
manufacture, as indicated in the table entries, has been replaced with 
4-dodecylphenol of the Aldrich Chemical Company. 
"A-PDP" is a resin having substantially the same composition and method of 
manufacture as resin CON except that a portion of the phenol used in its 
preparation has been replaced with 3-pentadecylphenol of Aldrich Chemical 
Company in the amount indicated in the table. 
"S-OCT" is a resin having substantially the same composition and method of 
manufacture as resin CON except that a portion of the phenol used in its 
preparation has been replaced with 4-octadecylphenol of Schenectady 
International in the amount indicated in the table. 
"V-DDP" is a resin having substantially the same composition and method of 
manufacture as resin CON except that a portion of the phenol used in its 
preparation has been replaced with 4-dodecylphenol, in the concentration 
shown in the tables, and wherein the dodecylphenol is a product of the 
Vilax Chemical Company. 
"CARD" is a resin having substantially the same composition and method of 
manufacture as resin CON except that a portion of the phenol used in its 
preparation has been replaced with cashew nut shell liquid of the 
Cardolite Company, namely, Cardolite NC-700. 
The laminated composites tested in this example are those of OSB (oriented 
strand-board) 
In the following tables, under the designation of "%*" is the percent by 
weight of the aliphatic hydrocarbylphenol which was substituted for phenol 
in the terpolymerization of the resin, based on the weight of the aqueous 
resin composition during the manufacture of the resin. The "WA % IMP" and 
"TS % IMP" is the percent of improvement in water absorption or thickness 
swell, respectively, of the indicated sample in relation to the CON resin 
which did not contain hydrocarbylphenol polymerized therein. 
TABLE 2A 
______________________________________ 
IB, IB, WA % TS % 
Resin %* lb/in.sup.2 
Kg/cm.sup.2 
WA % IMP TS % IMP 
______________________________________ 
CON 0 41.0 2.88 76.0 31.5 
A-DDP 0.5 46.4 3.26 76.4 -0.5 27.9 11.4 
A-DDP 1.0 33.5 2.36 80.9 -6.1 32.8 -4.0 
A-DDP 2.0 36.4 2.56 64.3 15.4 26.2 16.8 
A-PDP 0.5 45.1 3.17 60.1 20.9 20.0 36.5 
______________________________________ 
It can be seen from Table 2A above that at the test concentrations, the 
hydrocarbylphenols offer improvement in properties in comparison with the 
Control (CON)resin when used as binders in the preparation of oriented 
strand-board. 
TABLE 2B 
______________________________________ 
IB, IB, WA % TS % 
RESIN %* lb/in.sup.2 
Kg/cm.sup.2 
WA % IMP IMP TS % 
______________________________________ 
CON 0 35.3 2.48 77.8 30.7 
S-OCT 1.0 26.0 1.83 81.2 -4.2 1.0 30.4 
A-DDP 0.5 38.5 2.71 61.5 21.0 27.0 22.4 
A-DDP 1.0 38.0 2.67 66.3 14.8 28.7 21.9 
A-PDP 1.0 44.3 3.11 50.5 35.1 46.6 16.4 
______________________________________ 
From the above Table 2B it can be seen that the S-OCT resin with its 18 
carbon hydrocarbyl group was not as effective as the hydrocarbyl phenols 
having from 12 or 15 carbon atoms. 
TABLE 2C 
______________________________________ 
IB, IB, WA % TS % 
RESIN %* lb/in.sup.2 
Kg/cm.sup.2 
WA % IMP IMP TS % 
______________________________________ 
CON 0 29.1 2.04 74.3 29.4 
A-DDP 0.5 26.0 1.83 54.4 26.8 35.0 19.1 
A-DDP 1.0 41.5 2.92 56.3 24.2 20.4 23.4 
V-DDP 0.5 32.6 2.29 50.8 31.6 43.2 16.7 
V-DDP 1.0 31.2 2.19 40.9 45.0 59.9 11.8 
______________________________________ 
From the above Table 2C and the following Tables 2D and 2E, it can be seen 
that the hydrocarbylphenols in the concentrations employed offer improved 
properties when used as binders in the preparation of OSB panels when 
compared with the Control (CON) resin which did not contain 
hydrocarbylphenol. 
TABLE 2D 
______________________________________ 
IB, IB, WA % TS % 
RESIN %* lb/in.sup.2 
Kg/cm.sup.2 
WA % IMP IMP TS % 
______________________________________ 
CON 0 49.3 3.46 59.1 20.6 
V-DDP 0.5 34.1 2.40 53.2 10.0 0 20.6 
V-DDP 1.0 35.3 2.48 54.8 7.3 14.1 17.7 
CARD 0.5 38.4 2.70 58.7 0.7 9.7 18.6 
CARD 1.0 37.7 2.65 42.8 27.6 37.4 12.9 
______________________________________ 
TABLE 2E 
______________________________________ 
IB, IB, WA % TS % 
Resin %* lb/in.sup.2 
Kg/cm.sup.2 
WA % IMP IMP TS % 
______________________________________ 
CON 0 46.5 3.27 71.3 26.7 
A-DDP 0.5 46.5 3.27 59.2 17.0 31.1 18.4 
A-DDP 1.0 45.5 3.20 60.5 15.1 30.7 18.5 
A-DDP 3.0 40.7 2.86 73.3 -2.7 -0.7 26.9 
A-DDP 5.0 44.3 3.11 45.6 36.0 4.5 25.5 
______________________________________ 
EXAMPLE 3 
Phenol-formaldehyde resole resin IN703A, a product of Borden Chemical, 
Inc., of 180 East Broad Street, Columbus, Ohio 43215, was compared with a 
resin made the same way as IN703A and having the same composition except 
that 1% of phenol starting material was substituted with 1% of Cardolite 
NC-700 in the polymerization with formaldehyde. Resin IN703A has a 
formaldehyde to phenol mole ratio of 2.2. The resin containing the 
Cardolite was designated IN703B. Both the standard resin (IN703A), also 
referred to as CONTROL RESIN and resin IN703B, also referred to as the 
TEST RESIN included 14.7% of urea dissolved in the resin. Resin IN703A is 
a conventional oriented strand-board resin having a solids content of 53%. 
Some foaming was experienced during the manufacture of the TEST RESIN and 
about 0.2% of Colloid 999 was used to control the foaming. Colloid 999 is 
a product of Rhone-Poulanc having an office at Prospect Plains Road, 
Cranberry, N.J. 08512-7500. 
Each of the IN703A and IN703B resins were used to make oriented 
strand-boards of 3/8 (0.95 cm), 7/16 (1.1 cm), and 23/32 (1.8 cm) 
thickness by the same conventional techniques. The tests were run in 
substantially the same way as in Example 2. The results, as averages, for 
change in edge swell and change in center thickness, expressed as percent, 
due to moisture are shown in Table 3 below. Table 3 below also shows the 
density of the sample and this is expressed as pounds per cubic foot 
(lb/ft.sup.3) and it is further converted to kilograms per cubic meter 
(Kg/m.sup.3) 
It can be seen from Table 3 below that a 34% improvement in edge swell and 
a 25% improvement in center thickness was obtained in comparison with the 
standard test resin by use of IN703B which contained the terpolymerized 
Cardolite NC-700. 
TABLE 3 
______________________________________ 
Density Density Edge Center 
Product (lbs/ft.sup.3) 
(Kg/M.sup.3) 
Swell Thickness 
______________________________________ 
TEST RESIN 43.1 690 12.4% 11.3% 
CONTROL RESIN 
43.6 698 18.9% 15.1% 
______________________________________ 
EXAMPLE 4 
This example shows tests on OSB samples wherein Control (CON) resin Borden 
303K, a phenol-formaldehyde resole resin having a formaldehyde to phenol 
mole ratio of 2.4 and including 9.5% of urea was used as the core resin 
and Borden IN703A phenol-formaldehyde resin was used as the face-resin for 
oriented strand-board samples, designated "B" in Table 4 in comparison 
with samples treated in the same manner wherein by use of the face-resin 
and the same core resin but: sample 303K resin was modified by having 0.5% 
of 4-dodecylphenol substituted for an equal weight to phenol and cooked in 
the resin, i.e. terpolymerized with the phenol and formaldehyde, this is 
designated as "A" in Table 4; 0.5% of linseed oil was back-added to the 
303K resin and this is designated as "C" in Table 4; and 0.5% of 
4-dodecylphenol was back-added to the 303K resin and this is designated as 
D in Table 4. The IN703A resin used as a face-resin was not modified by 
cooking in or back-adding any of the modifiers of the 303K resin. The 303K 
resin contained 9.5% of urea in all instances whereas resin IN703A 
contained 14.7% of urea, by weight of the resin. The procedure set forth 
in Example 2 was used for testing the resins in this example. 
The control parameters for this example included: 3.5% resin treatment on 
the wood particles; a 3.5 minute press cycle for 2 and 7/16 inch (6.2 cm) 
boards; 1% wax treatment; a 3% moisture content for the wood flake 
starting material; and pressing at 400.degree. F. (204.degree. C.). 
The tests were run in duplicate. Results, as averages of the duplicate runs 
are shown in Table 4. 
It can be seen from Table 4 below that the 0.5% addition of 
4-dodecylphenol, post-added, to the standard resin (Control) as well as 
the use of 0.5% of dodecylphenol substituted for an equal amount of phenol 
and polymerized in with the phenol and formaldehyde showed good 
improvement in internal bond (IB) strength over the Control. The percent 
water absorption (WA)and thickness swell (TS) values showed little 
difference between the Control and the resins which included the 
hydrocarbylphenol and this is believed to be due to the lack of 
hydrocarbylphenol in the face-resin. The Table also shows the percent 
improvement in the water absorption (WA % IMP.) and percent improvement in 
thickness swell (TS % IMP.) in relation to the Control. The use of linseed 
oil back added to the 303K resin resulted in internal bond strengths 
comparable to the resins using the hydrocarbylphenol however, the water 
soaks suffered greatly. 
TABLE 4 
______________________________________ 
IB, Den- Den- WA TS 
Sam- IB, Kg/ sity sity % % 
ple lb/in.sup.2 
cm.sup.2 
lb/ft.sup.3 
Kg/m.sup.3 
% WA IMP. IMP. % TS 
______________________________________ 
A 83.5 5.87 43.1 690 38.4 4.5 11.1 25.7 
CON 67.4 4.74 42.8 680 40.2 28.9 
C 78.9 5.55 44.7 716 64.5 -62.9 
-52.6 44.1 
D 79.8 5.61 43.3 694 36.4 9.5 0.0 28.9 
______________________________________ 
EXAMPLE 5 
Samples of OSB panels made from phenol-formaldehyde resole resin FC-23B 
(Control), a product of Borden Chemical, Inc., was compared with panels 
wherein 1%, 3%, 5% and 7% of nonylphenol was substituted for an equal 
amount of phenol in polymerization of phenol and nonylphenol with 
formaldehyde during the manufacture of the resins. Resin FC-23B has a 
formaldehyde to phenol mole ratio of 2.4, 9.1% urea dissolved therein and 
51% total solids. The resins were manufactured in the manner of Example 1 
except that the FC-23B, the Control, did not contain nonylphenol and the 
other resins contained the below designated quantities of the nonylphenol. 
The samples were tested in accordance with the method of Example 2. The 
results of the tests are shown, as averages of 4 tests for the Control and 
each level of concentration of nonylphenol as shown in Table 5. Table 5 
shows the percent water absorption and percent thickness swell of each 
sample, as well as the percent improvement(IMP) of water absorption (WA) 
and thickness swell (TS) of samples containing the nonylphenol in 
comparison to the Control which did not contain nonylphenol. It can be 
seen from Table 5 that the only samples which outperformed the Control 
were those wherein the resin had 3% of nonylphenol cooked therein. It can 
also be seen that the samples containing more than 3% of the nonylphenol 
and the sample containing 1% of the hydrocarbylphenol were less effective 
than the Control. 
TABLE 5 
______________________________________ 
% 
% Water % IMP Thickness 
% IMP 
Resin Absorption in WA Swell in TS 
______________________________________ 
Control 43.2 13.9 
1% Nonylphenol 
42 2.8 19.3 -28.0 
3% Nonylphenol 
34.6 19.9 10.9 21.6 
5% Nonylphenol 
48.9 -11.7 18.2 -23.6 
7% Nonylphenol 
45.4 -4.8 16.9 -17.8 
______________________________________ 
EXAMPLE 6 
Using the resins in Example 5, OSB panels were prepared and tests made to 
determine the Modulus of Rupture (M.O.R.). The test procedure for 
measurements of (M.O.R) is set forth in U.S. Pat. No. 5,498,647 to D. 
Shiau et al of Mar. 12, 1996 which is incorporated herein by reference in 
its entirety. The results of the tests wherein four samples of OSB were 
tested for each of the resins, except as otherwise indicated, are shown in 
Table 6. Table 6 also shows the percent improvement (IMP) in M.O.R. in 
relation to the Control. It can be seen from Table 6 that the only 
modified resin which produced better results than the control was the 
resin containing 3% of nonylphenol. The M.O.R. is expressed in pounds per 
square inch which has been converted to kilograms per square centimeter. 
TABLE 6 
______________________________________ 
M.O.R., M.O.R. % IMP in 
Resin Kg/cm.sup.2 
lb/in.sup.2 
M.O.R. 
______________________________________ 
Control 212.4 3022 
1% of nonylphenol 
187.8 2672 -11.6 
3% of nonylphenol 
229.5 3265* 7.4 
5% of nonylphenol 
172.0 2447 -19.0 
7% of Nonylphenol 
210.5 2994* -0.9 
______________________________________ 
*Only three tests were considered since one of the tests for each resin 
showed results which were not consistent with the other three. 
EXAMPLE 7 
In this example, FC-23B base resin was again used as the control resin and 
it was modified by replacing phenol for the designated quantity of 
hydrocarbylphenol or mixtures of hydrocarbylphenols in the polymerization 
of the resin in substantially the same manner as in Example 1 above. In 
the below Table 7, and Table 7A the abbreviations for the various samples 
designate the following resins: "CONTROL" is Resin FC-23B; whereas the 
remaining resin designations are the same as in Example 2 above. 
In this example OSB samples of the Control resin were compared with OSB 
samples of various modified resins in determination of: M.O.R. in Table 7, 
expressed as pounds per square inch which were also converted to kilograms 
per square centimeter and the percent improvement in M.O.R. in relation to 
the Control; and in Table 7A, water absorption (%) and thickness swell (%) 
as well as the percent improvement in thickness swell (TS) and the percent 
improvement in water absorption (WA) in relation to the Control. The tests 
were run in substantially the same manner as in Example 2. 
It can be seen that in all instances the samples of OSB using the modified 
resins outperformed the CONTROL and some of the modified resin mixtures 
gave better results than each of the modified resins alone. The data shown 
below are averages of 4 separate trials. 
TABLE 7 
______________________________________ 
% IMP in 
Resin M.O.R. lb/in.sup.2 
M.O.R. Kg/cm.sup.2 
M.O.R 
______________________________________ 
CONTROL 3456.8 243 
1% CARD 4137.5 291 16.5 
1% VDDP 3511 247 1.5 
0.5% VDDP + 
4243.2 298 18.5 
0.5% CARD 
0.99% VDDP + 
4393.5 308.9 21.3 
0.99% CARD 
1:1 Mixture 
3925.5 276 11.9 
of 1% ADDP + 
1% CARD 
______________________________________ 
TABLE 7A 
______________________________________ 
% Water % IMP Thickness 
% IMP 
Resin Absorption in WA Swell % in TS 
______________________________________ 
CONTROL 44.7 14.8 
1% CARD 29.4 34.2 7 52.7 
1% VDDP 31.3 30.0 6.4 56.8 
0.5% VDDP + 
28.5 36.2 6.2 58.1 
0.5% CARD 
0.99% VDDP + 
26.4 40.9 5.8 60.8 
0.99% CARD 
1:1 25.4 43.2 5.3 64.2 
Mixture of 
1% ADDP + 
1% CARD 
______________________________________ 
EXAMPLE 8 
In this example, FC-23B base resin was again used as the Control resin. The 
Control resin was also modified by replacing 1% by weight of phenol for 
the designated hydrocarbylphenol set forth in Table 8 in the 
terpolymerization of the indicated resins wherein the procedure for 
preparation of the resins was by substantially the same manner as the 
preparation of the Control resin. 
In Table 8 below, the various resins are abbreviated as follows: Resin 
FC-23B is referred to as "Control"; Cardolite NC-700 is referred to as 
"Cardolite"; 4-nonylphenol is referred to as "Nonyl" 4-tert-octylphenol is 
referred to as "octyl"; and 4-sec-butylphenol is referred to as "butyl". 
In addition to the indicated resin samples, samples were also prepared by 
substituting 1% of 4-dodecylphenol in place of phenol in the manufacture 
of the terpolymer in the same manner as the other terpolymer resins. 
However, errors occurred in the preparation of the dodecylphenol samples 
and the results were inconsistent with 4-dodecylphenol samples run in the 
past and therefor not included in Table 8. 
The samples were tested for modulus of rupture (M.O.R.)and the results are 
reported in Table 8 as pounds per square inch and also converted to 
kilograms per square centimeter. Also, the samples were tested for percent 
water absorption and percent thickness swell due to water exposure in 
comparison with the samples weight or thickness, respectively before being 
subjected to the tests. 
TABLE 8 
______________________________________ 
M.O.R. M.O.R. Water Thickness 
Resin lb/in.sup.2 
Kg/cm.sup.2 
Absorption 
Swell 
______________________________________ 
Control 3443 242 36.9% 12.4% 
1% Cardolite 
3952 278 30% 7.9% 
1% Nonyl 3301 232 34.1% 9.3% 
1% Octyl 3330 234 34.1 9.8% 
1% Butyl 3158 222 38.2 12.1 
______________________________________ 
It can be seen from the above Table 8 that: 
(a) the M.O.R. results for the resin containing terpolymerized Cardolite 
were 16% better than that of the resin containing terpolymerized 
octylphenol or nonylphenol and 20% better than that containing 
terpolymerized butylphenol; 
(b) the water absorption results for the resin containing terpolymerized 
Cardolite were 12% better than the resin containing terpolymerized 
nonylphenol or octylphenol and 21% better than the resin containing 
terpolymerized butylphenol; and 
(c) the thickness swell results for the resin containing terpolymerized 
Cardolite were 19% better than the resin containing terpolymerized 
octylphenol, 15% better than the resin containing terpolymerized 
nonylphenol, and 34% better than the resin containing the terpolymerized 
butylphenol.