Bull. Mater. Sci., Vol. 16, No. 2, April 1993, pp. 137-150. (~ Printed in India.

Studies on structure and properties of CNSL novolac resins prepared

with succinic acid catalyst

K SATHIYALEKSHMI
Department of Chemistry,Sree Devi Kumari Women's~ollege,Kuzhithurai,Kanyakumari
District 629 163, India
MS received29 August 1991; revised 17 July 1992
Almtmet. Cashewnut shell liquid (CNSL)was used to prepare a glass fabriclaminate.Two
fast curingmodel resins were prepared usingcardanol and formaldehydein the presence of
suceinic acid catalyst.The resins possess ortho-ortho and ortho-para linkages.The curing
kinetics of the resins showed that the resin prepared with mole ratio 0"8 possesses good
curingcharacteristics.The IR spectra of cured resin showedresponsesfor high ortho linkage.
ACNSLhighortho novolacresin was preparedwithmoleratio 0-8.The glassfabriclaminates
prepared with CNSL resin showed good mechanicalproperties and dimensionalstability.
It is suggestedthat the candidatelaminatecan be used as secondaryload bearing structures
or panels.
Keywords. Novolac resins; succinic acid; cashew nut shell liquid; curing; glass fabric
laminate.

1. Introduction

Phenolic resins are a class of synthetic materials that have found increasing applica-
tions in recent years. Due to the decline in supply and price fluctuations in petroleum
raw materials, the use of natural products from renewable sources is gaining importance.
Cashew nut shell liquid (CNSL) obtained from cashew-tree nuts (Anacardium occiden-
tale) is used to develop a variety of industrial products. The production of cashew
nut, which has grown steadily in the last two decades, should yield 25~ of the
by-product technical CNSL though processing losses result in smaller yield (Dhler
1979). CNSL is obtained during isolation of the kernels by roasting the raw nuts or
by the hot oil process. The principal components of natural CNSL are anacardic
acid, cardol, 2-methylcardol and anacardol (Tyman 1979): On heating, anacardic acid
is decarboxylated to cardanol. The thermally treated CNSL contains a mixture of
cardol, cardanol and a small amount of self-polymerized CNSL. Cardanol is a n-
pentadecadienyl phenol, the aliphatic side chain usually consists of mixtures of one,
two and three double bonds in a linear chain with saturated side chain 5.4~, monolefin
48.5~, diolefin 16-89/o and triolefin 29.33~ (Murthy et al 1968).
Substituted phenols used for preparation of substituted phenolic resin (Redfarn
1942; Freeman and Traylar 1961) differ in their reactivity with formaldehyde. Therefore,
it is of interest to study the formylation of cardanol and curing of methylolated
cardanol in the presence of acid catalyst. It has been found that the use of certain
metal salts e.g. zinc, magnesium or calcium acetate etc. under an intermediate alkaline
pH 4-7 and 15-309/0 molar excess of phenol over formaldehyde results in the formation
of novolac that have a disproportionately high concentration of ortho-ortho repeat
units (Bender et al 1949). The unique properties displayed by high ortho novolacs
are cure speed and rheological properties. However, the effect of metta-substituted

137
138 K Sathiyalekshmi

long chain in cardanol on curing characteristics of high ortho CNSL based novolac
resin is one aspect which needs further studies. Jayabalan and Rajadurai (1985)
prepared high ortho cardanol-based novolac resin using m-cresol, a trifunctional
accelerator (crosslinker) and alkali catalyst (pH 9). Studies on the formylation of
cardanol leading to high ortho novolac and curing of such novolac in the absence
of accelerator are scarce.
Oxalic acid has been used as an acid catalyst to produce novolac phenolic resin
with a pH range of 0.5 to 1.5. It is known that acids in which there are two carbonyl
groups separated by a chain of more than 5 carbon atoms, have different properties.
The acid strength of the dicarboxylic acid as measured by the first dissociation
constant K1 decreases with increasing number of bonds between the two carbonyl
groups. K~ values at 25°C being 6"6 x 10 -5 for succinic acid, 4.7 × I0 -s for glutaric
acid and 3"7 x 10-5 for adipic acid. With the low acid strength which falls in the pH
range 4-7, the higher aliphatic dicarboxylic acid can influence formylation and
orientation of cardanol. Information on the catalytic effect of aliphatic dicarboxylic
acid on the formylation of cardanol and curing, as high ortho novolac resin, is scarce.
Attempts have therefore been made to study the use of an aliphatic dicarboxylic acid
such as succinic acid as a catalyst. This paper deals with studies on the formylation
of cardanol, curing characteristics of formylated product and preparation of CNSL
resin and laminate.

2. Experimental

2.1 Materials

CNSL was procured from local sources. Cardanol was obtained from M/s Card-chem
Industries, Hyderabad. Formaldehyde (40~ solution) (BDH) was used for formylation.
Succinic acid (E-Merck) was used as a catalyst and methanol (BDH) was used to
dissolve the catalyst. Hexamine was used for curing the resin.

2.2 Analyses of cardanol and CNSL

Cardanol and CNSL were subjected to extensive analyses such as determination of

saponification value, iodine value, viscosity test, specific gravity, volatile matter at
200°C, moisture content and insoluble matter in toluene following standard procedures
(ISI Standard 840-1964).

2.3 Synthesis of eardanol-formaldehyde model novolac resin

Novolac resins with two different mole ratios i.e. 1:0.6 and 1:0-8 of cardanol to
formaldehyde were prepared using succinic acid as the catalyst. Catalyst (1~) based on
cardanol was dissolved in 2ml methanol under warm conditions. Cardanol was
weighed into a three-necked flask fitted with a Leibig's condenser, ground joint
thermometer and mercury seal stirrer. Formaldehyde (40~) solution was added to
cardanol through a dropping funnel along with the catalyst. The pH of the reaction
mixture was noted using a pH meter. The reaction mixture was heated to 120 + 5°C
 Studies on CNSL novolac using succinic acid catalyst 139

under constant stirring for 3 h. The reaction mixture (I ml) was withdrawn for deter-
mining formaldehyde to check the completion of methylolation reaction (Urbanski
et al 1977). The final pH of the mixture was noted. The reaction product was cooled
and dried under vacuum at 60°C overnight before purification by column chromato-
graphy. A resin solution prepared with n-hexane was charged to the silica gel column.
Chromatographic purification was adopted mainly to remove unreacted components,
impurities, etc. from the methylolated cardanol. Purification was effected using the
elutant mixture of ethylacetate/benzene (60:40). The purified resin was analyzed by
ultraviolet spectral analysis (as 0"05~o n-hexane solution), IR spectral analyses (as
resin smear on sodium chloride window) and proton NMR spectral analyses (as
carbon tetrachloride solution).

2.4 Curing kinetics and IR spectral analysis of cured (B-stage) resin

The oven-dried model cardanol-formaldehyde resin was treated with 18~ hexame-
thylene tetramine and blended well using mortar and pestle. Approximately 5 mg of
blended resin was taken to study the curing kinetics of the resin by differential thermal
analysis. A thermal analyser 990 Dupont was used with reference thermocouple
loaded with micro glass beads. The glass beads were wetted with silicone oil to nullify
the high thermal conductivity of the resin. Initially DTA cell was heated isothermally
at 25°C for 15 min. The cell was then heated up to a maximum temperature of 200°C
at 10°C/min under nitrogen atmosphere. The curing kinetics curve appeared as a
function of change in enthalpy with temperature. In a separate experiment the
hexamine-blended resin was cured at 157°C under nitrogen atmosphere for 1 h in a
baking oven. The cured product (B-stage) was then taken for IR spectral analysis.

2.5 Synthesis of CNSL-formaldehyde resin

CNSL novolac resin was prepared using CNSL and formaldehyde in the ratio of
1.0:0.8 with succinic acid as catalyst (1~o based on CNSL). CNSL and formaldehyde
were allowed to react at 90-95°C for 2 h. The temperature was then raised to 120-130°C
and kept for l h. The reaction product was cooled, dried under vacuum at 60°C
overnight and used for fabrication of glass fabric laminate.

2.6 Fabrication of glass fabric laminate

CNSL novolac resin was dissolved in benzene/methanol (1 : 1) mixture to get a syrup

and mixed with 18~o hexamine and stirred well to get a homogeneous mixture. The
glass fabric woven cloth (E glass, satin weave, 15 mil, 8 hardness) was cleaned well
with methanol and dried in an oven at 100°C for 30 min. It was then uniformly coated
with resin syrup using a brush. The resin-coated glass fabric cloth (prepreg) was then
air-dried overnight. The prepreg was trimmed to get a rectangular sheet (12 x 8 cm).
Four sheets were stacked in a hand press and compressed manually. The hand press
was kept in an air oven set at 200°C for 1 h. The hand press was then taken out,
cooled to room temperature and the pressure released. The cured sheets were cut
into rectangular coupons for tensile tests and water absorption.
140 K Sathiyalekshmi

2.7 Tensile tests of glass fabric laminate

The laminates were tested for tensile properties (ASTM standard D3039-76) using
an Instron Universal testing machine. The gauge length of the specimen was 127 mm
and the area of cross-section 0.2 cm 2. The cross-head and chart speeds were both
100mm/min. Six specimens were tested for each sample and the average value
computed,

2.8 Tests for water absorption

The laminates were cut into square specimens (1 square inch), cleaned with distilled
water and dried. After weighing, the samples were immersed in distilled water. The
water absorption was determined by measuring the sample weight increase
periodically.

3. Results and discussion

3.1 Analysis of cardanol and CNSL

CNSL is usually obtained in India by a crude thermal process and the technical
CNSL contains large amounts of ash and other charred products of cashew. Analysis
of cardanol and CNSL is therefore desirable for phenolic resin preparation. The
analytical data of cardanol and CNSL are presented in table 1 and the values
compared with that of standard technical CNSL oil. The lesser viscosity of the

Table 1. Properties of cardanol and cashew nut shell liquid.

Standard*
technical
Properties Cardanol CNSL CNSL

Colour Dark brown Dark brown Dark brown

Smell Mild phenolic Smokyand mild Smokyand mild
odour phenolic odour phenolicodour
Specificgravity
(g/cc) at 30°C 0'873 0.962 0.960
Viscosity (CPS)
at 30°C 38.2 228 550
Saponification
value ,,22.4 121 --
Iodine value 274.8 278 250
Volatile matter
at 200°C (%) 4.0 4.2 2.0
Moisture content
at 100°C(%) 2-6 2"1 1"0
Insoluble matter
in toluene (%) if6 1"3 1"0

*ISI standard 840-1964

 Studies on CNSL novolac using succinic acid catalyst 141

Table 2. Formulation of model cardanol-formaldehyde resin.

Resin K - I Resin K - I I
Mole ratio of
formaldehyde Cardanol Formalde- Succinic Cardanol Formalde- Succinic
to cardanol (g) hyde (g) acid (g) (g) hyde (g) acid (g)

0"6 87'6 13.5 0.876 -- -- --

0"8 -- -- -- 75.5 15"0 0.755

cardanol indicates lesser ash content and non-self-polymerization. The iodine value
represents the degree of unsaturation. Cardanol exists in three different olefinic forms
with varied degrees of unsaturation in the long aliphatic side chain. The higher iodine
value ofcardanol and CNSL indicates the higher degree of unsaturation in comparison
to the standard CNSL oil.

3.2 Synthesis of eardanol-formaldehyde model resin

The methylolation of cardanol was carried out initially according to the formulation
shown in table 2. Succinic acid was used as a catalyst. The acid strength of this
dicarboxylic acid was lower than that of the oxalic acid. The pH of the reaction
mixtures for the model resins K-I and K-II was 4 during initiation of the reaction
indicating that the succinic acid imparts intermediate alkaline pH under the present
formulations of reaction mixtures as per the norms of pH of phenolic resins suggested
by Finn and Murty (1950). The methylolation reactions were carried out with 0"6
and 0-8 mole ratio of formaldehyde to cardanol. Therefore under this experimental
condition the complete formylation is expected to yield resin with high ortho-ortho
linkage as observed by Fraser et al (1957) for phenolic novolac resins.
The completion of the methylolation reaction was checked by periodic withdrawal
of reaction mixture to analyse formaldehyde using hydroxylamine hydrochloride
(Urbanski et al 1977). The final pH of the reaction mixture was 2. The decrease of
pH in the methylolated cardanol is ascribed to the monohydroxyl substituted
cardanol. Sperling (1954) found that methylolated phenol favours hydrogen bonding
with o-methylol and hydroxyl groups and releases hydrogen ion leading to increase
in acidity.
The newly prepared resins K-I and K-II are liquids and are soluble in n-hexane
and methanol.

3.3 Spectral analyses of model cardanol-formaldehyde resins, K - I and K - I I

The ultraviolet spectrum of the cardanol is given in figure 1, and those of K-I and
K-II resins in figure 2. The UV spectral data are given in table 3. The spectra of the
resins indicate a shift of peak towards the lower wavelength. The shift of the peak
from 247 to 228 in the case of K-I resin and to 237 in the case of K-II resin is due
to ortho substitution in cardanol. Such a shift was also observed in phenol with alkyl
substitution in ortho position (Silverstein et al 1981).
IR spectral analyses of K-I and K-II resins are given in table 4. The IR spectrum
 Absorbonce
0
o do 0~ o .~ ~ ~
I I I I I I I
I~0
0
0
o
~. :r
o "~
'- 3
0
0
Absorbonce
0 0 .-. Pa I'~ Po
I I I I I I" I
0
c 0
o
D ._._~
s
tf
,,L ~" I
I
3 I
v /
I
I
I
!
!
I
!
0 I
0
 Studies on C N S L novolac usin9 succinic acid catalyst 143

Table 3. UV spectral data of model cardanol-

formaldehyde resins.

UV absorption (wavelength in nm)

Responses Cardanol K-I K-II

Substitution 247 228 237

Aromatic 278 272 272
(doublet) 282 280 280

Table 4. IR spectral data of model cardanol formaldehyde

resins.

Peak cm - i Response K-I K-II

3700-3100 -CH2OH, - O H and S S

broad p e a k hydrogen bonding
centering 3370
3020 -CH stretching S S
aromatic-hydrogen
stretching
2915-2860 -CH stretching S S
from - C H 2
1720 C - O stretching from W M
CH2OH
1600 Unsaturation (un- S S
conjugated)
1450 Alcoholic - O H S S
deformation
1250 and 1150 C - O stretching S M
1100 C - O stretching W W
from CH2OH
975,950 Substitution at W W
benzene nuclei
785,705 3 adjacent hydrogen M M
atoms in the benzene
nucleus

S = strong, W = weak, M = medium.

of cardanol is given in figure 3 and those of K-I and K-II resins in figure 4. A shift
of a weak peak from 1050 to 1100 cm- 1 and appearance of peak at 1720 cm- 1 were
observed in methylolated cardanol due to the CO stretching from CH2OH. The
bands at 975 and 950 also indicate the substitution at cardanol. Substitution at ortho
position is exhibited by the weak band at 725 cm-~ in K-I and K-II resins.
The NMR spectrum of cardanol is given in figure 5 and that of resins in figure 6.
The appearance of a peak at 2"8 6 of K-I and K-II is due to the benzylic protons
of the CH2OH group formed during methylolation. The peaks at 6"7 and 6-8 6 are
due to the aryl protons. The peaks around the region 6.46 are for the phenolic
144 K Sathiyalekshmi

80

~60
c
o

.g
g4o

20

I I I I I I
3600 2800 2000 1600 1200 800
Wove number (cr'n-1)

Figure 3. IR spectrum of cardanol.

80

~D

g 60
u

E
~g 4o
l!\;I/ hVp,7'/,/i
" ,,"~Vll " "; "~"' ' "
_ ,, .,, ,.,
20
',
0 I I I I I I ',
3600 2800 2000 1600 1200 800
Wove number (cm- 1 )
Figure 4. IR spectra of K - I and K - I I (A-stage).

hydroxyl. The peak at 5.1 6 is due to the methylene proton of long alkyl side chain
originally present in cardanol. The peaks between 0-8 and 2.4 6 are due to the aliphatic
long chain-CzsH27 group of the cardanol. The small peak at (}86 represents the
terminal methyl group of the chain. The strong peak at 1.3 3 is attributed to the
long chain (> 5 member) of the side chain.
Spectral studies indicate that the initial formylation of cardanol leads to methylola-
 Studies on CNSL novolac using succinic acid catalyst 145

I I 1 I I I
7 6 .5 4 3 2 1 0

Figure 5. H' NMR spectrum of cardanol (60 M Hz).

s"

J
i r

iI
iI

TMS

i
slII
s

/ S

L
j /t

\
~I'" I " '. . . . ~ ...... ~" I

7 6 5 4 3 2 1 0

Figure 6. H' NMR spectrum of K-I and K-II (A-stage)(60MHz).

146 K Sathiyalekshmi

OH

Cardanol~ C l 5 H27
+
HCHO

~CHzOH
OH
HOH2C~cH2OH
OH
HOH2~CHzOH
OH

Cl5H27 v -CI5H2? ~"ClsH27

CHzOH
Methyloloted ¢ordonols
Schemel.
tion under the present experimental conditions ranging from single to triple
substitution as shown in scheme 1.

3.4 Kinetics of curing reaction of model cardanol-formaldehyde

resins, K - I and K - I I

The kinetics of the curing reaction of the present methylolated cardanol are different
from the initial reaction of cardanol with formaldehyde. This is not only due to the
influence of metta-substituted long chain but also because the pH of the methylolated
cardanol is reduced from 4 to 2. Therefore, further reaction occurs as an acid-catalysed
novolac condensation. The differential thermal analysis scans of the curing reactions
are given in figure 7. The methylolated phenol condenses rapidly with phenol or
phenol-ended polymer molecules, in the presence of an acid catalyst (Kakiuchi and
Otsu 1952). This condensation rate is five to eight times as fast as the initial addition
reaction (Kakiuchi and Otsu 1952). According to Little (1962) the overall reaction
rate is a function of the acidity; the lower the pH, the faster the reaction. A different
trend has been observed with metta-substituted phenol where substitution increases
reactivity at ortho and para positions. Therefore the initial formylation of metta-
substituted phenol is quite fast. However the subsequent curing rate is slower than
that of the unsubstituted phenol (Redfarn 1942).
The present curing reaction is depicted by the appearance of exothermic peak in
DTA scan when assessed (figure 7). The curing temperatures of K-I and' K-II resins
are given in table 5 where both the resins exhibit two exothermic peaks. The first
peak for K-II appeared at 74°C indicating low temperature reactivity. K-II was
prepared with mole ratio 0.8 and therefore the availability of formaldehyde for the
initial methylolation reaction is greater in comparison to K-I prepared with the mole
ratio 0"6. The higher mole ratio leads to varied degrees of methylolation ranging
from single substitution in ortho position to triple substitution in both ortho and
para positions; the fraction of single substituted cardanol may be the lowest. The
 Studies on C N S L novolac using succinic acid catalyst 147

74

E
(D
AZ
O
LO

<3

I l I I I
20 60 100 140 180
Yemperoture I°C)
Figure 7. Curing reaction thermograms of K-I and K-II (DTA).

Table 5. Data on curing reactions (kinetics) of model cardanol formaldehyde resins.

First exotherm Second exotherm

I curing temperature II curing temperature

(°C) I curing (°C) II curing
time time
Resin Initial Peak Terminal (min) Initial Peak Terminal (min)

K-I 101 113 117 9.0 117 132 137 11-0

K-II 54 74 77 5.0 118 134 168 11-0

methylotated cardanol having substitution only at ortho position leads to faster

condensation at lower temperature to complete the methylolation in other positions
of cardanol. The curing time associated with the first exothermic peak for K-II is
lesser than that of K-I (table 5). The second exothermic peak for K - I and K-II
resins is attributed to the condensation of methylolated (ortho, ortho and para-
substituted) cardanol to give a linear structure.
During the initial curing of methylolated phenol with hexamine, three reactions
are possible (Sprung and Gladstone 1949; Hoyt et al 1958): (i) Formation of ether
linkage between two phenol rings, (ii) formation of methylene linkage between two
phenol rings and (iii) formation of quinonoid structure.
The linear structures expected to form with the present methylolated cardanol are
shown in scheme 2. From the kinetics of curing reaction it is inferred that K-II is
initially fast reactive in comparison to K-I.
148 K Sathiyalekshmi

OH OH OH _ OH

"F C~sHz7 "F c ~ T c~Hz~ T c l ~

CH2OH CH2OH CH2OH CH20H
1. Formation of ether linkage

OH OH
.O.~C,~CH~OH + [~,c.2o.

CH2OH CHzOH
CH2
HOHzC'~ ~ cHZOH

y "C~H~ y "C~H2?
CH2OH CH2OH
2 .Formation of methykme linkage

(-)
OH 0 0

L°l "C151"12"/
L°].
y "C'E,Hz'7
I~ ol"C15H27
CH20H CH20H CH20H

3 .Formation of quinonoid structure

Scheme 2.

3.5 Curing and characterization of model cardanol-formaldehyde resin

The characterization of cured resin was aimed at finding out the structure of the
linear polymer formed during preliminary curing. The IR spectra of the cured B-stage
resins are given in figure 8. The intensity of the bands for the -CH 2OH (3332 cm-1 ),
alcoholic-OH of CH2OH (1450cm-z), and - O H (1250 and 1150cm-1), reduced
appreciably in K - I resin. Interestingly in K-II cured resin small peaks appeared at
950-975 and 1225cm -1 intensity. There was a new band at 825cm -I. The weak
band at 725 cm-z became more clear and distinct. These bands are attributed to the
increased substitution at ortho and para positions. The band at 725 c m - t indicates
the presence of ortho-ortho linkage in this partially cured resin. Phenolic novolac
resins showed absorbance at 760cm -1 for ortho-ortho and 825-840cm -1 for
ortho-para linkages. The intensity of the former was higher for high ortho novolac
(Fraser et al 1957). Cardanol novolac showed these absorbances in lower level due
to substitution in metta position.

3.6 Development and testing of glass fabric laminates

IR spectral studies on the model cardanol-formaldehyde B-stage resin indicate that

methylolated cardanol condenses with formaldehyde in ortho-ortho and ortho-para
positions with higher degree of ortho-ortho linkage. Such resins are expected to give
 Studies on CNSL novolac using succinic acid catalyst 149

80 - K II

"---'~,, .j \ / • . v r', ~, l ~

o
u 60
i ~I. I
g
I I
E
c 40
0

20

I I I I I I
3600 2800 2000 1600 1200 800
Wove number (cm-1)

Figure & IR spectra of cured K-I and K-II resin (B-stage, 18% hexamine).

Table 6. Water absorption of CNSL Nov olac

laminate.

Period of Weight gain

immersion
o/
(days) grfl /a

7 0.030 + 0.002 3.3 ___0-2

14 0.072 + 0'010 7.98 _+_1'1
21 0.075 + 0-010 8'31 __+1.1
28 0-076 + 0.012 8.42 + 1.3
35 0.076+0.01 8.42+ 1.1

Weight of the sample, 0.9026g; Number of

specimen, 6.

curing speed higher than that of resins with high para linkage (Bender et al 1949).
K-II resin was found to possess superior curing characteristics compared to K-I
with hexamine. Hexamine has been generally used for curing of phenolic resins to
get a thermoset. Hexamine sublimes quite rapidly at 150°C. The three bonds associated
with one of the nitrogen atoms of hexamine molecule opens to react at the end group
of phenol ring of three separate novolac chains. CNSL novolac resin prepared using
K-II formulation was used to prepare glass fabric laminate. The tensile properties
of the laminate were 14"65_+ 2"85 KN/cm 2 (tensile strength) and 3.8+0.8 (%
elongation).
The tensile strength of the candidate laminate is comparatively higher than that
of laminate prepared with high ortho novolac reported earlier. Jayabalan and Rajadurai
(1985) reported a tensile strength of 12-60 _+ 2.5 KN/cm 2 for their laminate prepared
with resin synthesized from CNSL, formalin and m-cresol (accelerator) at pH 8.0 with
mole ratio 0.8. The presence of long chain with unsaturated double bonds can lead
to a certain degree of internal plasticization in the cured thermoset. Such characteristics
can give comparatively low tensile strength but can also give high impact resistance
150 K Sathiyalekshmi

compared to that of phenolic resin. The data of water absorption of the candidate
laminate are given in table 6. Water absorption attained an equilibrium after the
post-immersion period of 14 days with absorption around 8%. The laminate did not
attain delamination even after the post-immersion period of 35 days, thereby
indicating that the laminate possesses good interlaminar adhesion.

4. Conclusion

Succinic acid catalyses the formylation of cardanol. Subsequent curing leads to high
ortho novolac resin.
The model cardanol formaldehyde resin prepared with mole ratio of 0.8 possesses
good curing characteristics. The initial curing rate of this resin is not only influenced
by the presence of long chain in the cardanol and pH of the curing reaction but also
by the level of fraction of singly-substituted formylated cardanol. CNSL resin prepared
with this formulation and the resultant laminate have good mechanical properties
and dimensional stability. These laminates can be used as secondary load-bearing
structures or panels.

References

Bender H L, Farnham A G and Guyer J W 1949 March 15 US Pat. 2, 464, 207

Dhler J G 1979 Cashew (Amsterdam: Royal Tropical Institute) ed. 1, p. 21
Finn S R and Murty J W G 1950 J. Soc. Chem. Ind. (London) 69 549
Fraser D A, Hall R W and Reun J L 1957 J. Appl. Chem. (London) 7 676
Freeman J H and Traylar E J 1961 J. Soc. Plastics Eng. 17 673
Hoyt H E, Keuchel H W and Dean R B 1958 Paint and Varnish Prod. 48 33
Jayabalan M and Rajadurai S 1985 Popular Plastics 30 30
Kakiuchi H and Otsu T 1952 Chem. High Polym. Japan 9 303
Little G E 1962 J. Appl. Chem. (London) 12 196
Murthy B G K, Sivasaraban M A and Aggarwall J S 1968 J. Chromatogr. 32 519
Redfern C A 1942 Br. Plast. 13 481
Silverstein R M, Clayton G and Morrill T C 1981 Spectrometric identification of organic compounds
(New York: John Wiley) ed. 4, pp. 305
Spefling G R 1954 J. Am. Chem. Soc. 76 1190
Sprung M M and Gladstone M T 1949 J. Am. Chem. Soc. 71 2907
Tyman J H P 1979 Chem. Soc. Rev. 8 499
Urbanski J, Czerwinski W, Ianika K, Majewsta F and Zowall H 1977 Handbook of analysis of synthetic
polymers and plastics, (Chichester: Ellis Horwood) p. 179