COMPOUND AND COMPOSITION CONTAINING THE SAME
TECHNICAL FIELD
[0001] This invention relates to a novel composition or compound
improving an adhesion durability to a metal reinforcing material such
as a steel cord used for rubber products such as a pneumatic tire, an
industrial belt and the like. More particularly, this invention relates
to a compound having a specific structure capable of improving a
workability of a rubber composition obtained by compounding with
rubber and of stably developing an initial adhesion and a humidity-
aged adhesion to a metal reinforcing material regardless of the storage
period of the rubber composition, as well as a composition mainly
containing the above-mentioned compound,
BACKGROUND ART
[0002] In the rubber products particularly requiring the strength
such as tires for automobiles, conveyor belts, hoses and the like, a
composite material formed by covering a metal reinforcing material
such as a steel cord with a rubber composition is used for the purpose
of reinforcing rubber to improve the strength and durability. In order
that the rubber-metal composite material develops a high reinforcing
effect to provide a reliability, a stable adhesiveness not depending on
conditions of mixing, compounding, storage and so on is required
between the rubber and the metal reinforcing material. In order to
obtain such a composite material, there is widely used a so-called
direct vulcanization adhesion, in which the metal reinforcing materials
such as steel cords or the like plated with zinc, brass or the like are
embedded in the rubber composition containing sulfur and adhered
thereto at the same time as the vulcanization of rubber during the
vulcanization by heating. Until now, there are made various
investigations for improving the adhesiveness, particularly the
humidity-aged adhesion between the rubber and the metal reinforcing
material in the direct vulcanization adhesion.

[0003] For example, there is reported a rubber composition in which
a resorcin or a resorcin-formaldehyde resin (hereinafter abbreviated as
"RF resin") obtained by the condensation of resorcin and formalin is
compounded for improving the humidity-aged adhesion (see JP-A-
2001-234140). The humidity-aged adhesion between the steel cord
and the rubber is certainly improved by compounding the RF resin.
[0004] However, the resorcin or the RF resin is poor in the
compatibility with rubber because the polarity is very high, and the
precipitation of the resorcin or the RF resin or so-called blooming is
caused in accordance with conditions of mixing, compounding, storage
and so on, so that there is a fear of damaging an appearance of the
rubber product. And also, when the rubber composition is stored over
a long time of period ranging from the compounding to the vulcaniza-
tion adhesion, a problem of deteriorating the adhesiveness is caused by
blooming, so that it is necessary to rapidly conduct the vulcanization
adhesion of the rubber composition containing the resorcin or the RF
resin, which may detract the productivity of the rubber product.
[0005] Also, an adhesive material made from a mixed polyester
having a resorcin skeleton with a weight average molecular weight of
3000-45000 is reported (see JP-A-7-118621). Although the mixed
polyester having a high molecular weight is more compatible with the
rubber as compared with the RF resin, the compatibility can not still
be satisfied. Moreover, when the mixed polyester having a high
molecular weight is compounded with rubber, the viscosity of the
compounded rubber is increased to cause a problem of lowering the
workability, and the humidity-aged adhesion is not sufficient.
SUMMARY OF THE INVENTION
[0006] It is, therefore, an object of the invention to provide a
compound having a specific structure capable of suppressing the
blooming, which was seen in the compounding of the resorcin or the
RF resin, as far as possible while maintaining the workability and high
humidity-aged adhesion of the rubber composition at the time of
compounding with rubber, and reducing the deterioration of the

adhesiveness during the storage of the rubber composition, and
developing an excellent adhesion stability, as well as a composition
containing the above-mentioned compound as a main component.
[0007] The inventors have made various studies in order to achieve
the above object, and found that when the compound having a specific
structure or the composition containing the compound as a main
component is compounded with rubber, the workability of the rubber
composition, which is a problem in the compounding of the resorcin or
RF resin with rubber, can be improved while maintaining the humidity-
aged adhesion equal to or more than that of the resorcin or RF resin
containing system to suppress the occurrence of the blooming and an
excellent adhesion stability can be attained without depending on the
conditions of compounding, storage and so on, and as a result the
invention has been accomplished.
[0008] That is, the invention is concerned with (I) a compound
represented by the following general formula (1)

(wherein R is a divalent aliphatic group having a carbon number of
1-16);
(II) a compound according to the item (I), wherein the compound
represented by the general formula (1) is a compound represented by
the following general formula (2)

(wherein R is a divalent aliphatic group having a carbon number of
1-16); and
(III) a composition comprising 60-100 wt% of the compound
represented by the general formula (2), 0-20 wt% of a compound
represented by the following general formula (3) in which n is 2,

0-10 wt% of a compound represented by the following general formula
(3) in which n is 3 and 0-10 wt% of a compound represented by the
following general formula (3) in which n is 4-6, provided that the
composition does not include a pure material consisting of 100 wt% of
the compound represented by the general formula (2):

(wherein R is a divalent aliphatic group having a carbon number of
1-16, and n is an integer of 2-6).
[0009] According to the invention, there can be provided compounds
capable of suppressing the blooming, which is observed in the
compounding of the resorcin or the RF resin, as far as possible while
maintaining the workability and high humidity-aged adhesion of the
rubber composition obtained by compounding with rubber, reducing
the deterioration of the adhesiveness during the storage of the rubber
composition and stably developing the adhesiveness as well as the
composition containing the above-mentioned compound as a main
component.
BEST MODE FOR CARRYING OUT THE INVENTION
[0010] The invention will be described in detail below. The com-
pound of the invention is represented by the general formula (1).
R in the general formula (1) is a divalent aliphatic group having a
carbon number of 1-16. As the compound represented by the general
formula (1) are mentioned, for example, compounds represented by the
general formula (2). R in the general formula (2) is the same
meaning as R in the general formula (1).
[0011] As the divalent aliphatic group having a carbon number of
1-16 are mentioned, for example, linear or branched alkylene groups
such as methylene group, ethylene group, butylene group, isobutylene
group, octylene group, 2-ethylhexylene group and the like; linear or
branched alkenylene groups such as vinylene group (ethenylene group),

butenylene group, octenylene group and the like; a substituted alkylene
group or a substituted alkenylene group in which hydrogen atom in the
above-mentioned alkylene or alkenylene group is substituted with
hydroxyl group, amino group or the like; and a cycloaliphatic group
such as cyclohexylene group or the like. Among them, an alkylene
group having a carbon number of 2-10 is preferable for reasons of
availability, and ethylene group, butylene group and octylene group
are particularly preferable.
[0012] As a concrete example of the compound represented by the
general formula (1) are mentioned bis(2-hydroxyphenyl) malonate,
bis(2-hydroxyphenyl) succinate, bis(2-hydroxyphenyl) fumarate, bis(2-
hydroxyphenyl) maleate, bis(2-hydroxyphenyl) malate, bis(2-
hydroxyphenyl) itaconate, bis(2-hydroxyphenyl) citraconate, bis(2-
hydroxyphenyl) adipate, bis(2-hydroxyphenyl) tartrate, bis(2-
hydroxyphenyl) azelate, bis(2-hydroxyphenyl) sebacate, bis(2-
hydroxyphenyl) cyclohexanedicarboxylate, bis(3-hydroxyphenyl)
malonate, bis(3-hydroxyphenyl) succinate, bis(3-hydroxyphenyl)
fumarate, bis(3-hydroxyphenyl) maleate, bis(3-hydroxyphenyl) malate,
bis(3-hydroxyphenyl) itaconate, bis(3-hydroxyphenyl) citraconate,
bis(3-hydroxyphenyl) adipate, bis(3-hydroxyphenyl) tartrate, bis(3-
hydroxyphenyl) azelate, bis(3-hydroxyphenyl) sebacate, bis(3-
hydroxyphenyl) cyclohexanedicarboxylate, bis(4-hydroxyphenyl)
malonate, bis(4-hydroxyphenyl) succinate, bis(4-hydroxyphenyl)
fumarate, bis(4-hydroxyphenyl) maleate, bis(4-hydroxyphenyl)
itaconate, bis(4-hydroxyphenyl) citraconate, bis(4-hydroxyphenyl)
adipate, bis(4-hydroxyphenyl) tartrate, bis(4-hydroxyphenyl) azelate,
bis(4-hydroxyphenyl) sebacate, bis(4-hydroxyphenyl)
cyclohexanedicarboxylate and the like.
[0013] Among them, bis(3-hydroxyphenyl) malonate, bis(3-
hydroxyphenyl) succinate, bis(3-hydroxyphenyl) fumarate, bis(3-
hydroxyphenyl) maleate, bis(3-hydroxyphenyl) malate, bis(3-
hydroxyphenyl) itaconate, bis(3-hydroxyphenyl) citraconate, bis(3-
hydroxyphenyl) adipate, bis(3-hydroxyphenyl) tartrate, bis(3-

hydroxyphenyl) azelate, bis(3-hydroxyphenyl) sebacate and bis(3-
hydroxyphenyl) cyclohexanedicarboxylate are preferable, and bis(3-
hydroxyphenyl) succinate, bis(3-hydroxyphenyl) adipate and bis(3-
hydroxyphenyl) sebacate are particularly preferable.
[0014] The production method of the compound represented by the
general formula (1) is not particularly limited, but is produced, for
example, by reacting a dicarboxylic acid halide represented by the
following general formula (4):

(wherein R is a divalent aliphatic group having a carbon number of
1-16, and X is a halogen atom) with a compound represented by the
following general formula (5):

in the presence or absence of a base.
[0015] In the general formula (4), R is the same meaning as R in the
general formula (1), and X is a halogen atom. As the halogen atom, a
chlorine atom and a bromine atom are preferable.
[0016] As the compound represented by the general formula (4) are
mentioned aliphatic dicarboxylic acid dichlorides such as malonyl
dichloride, succinyl dichloride, fumaroyl dichloride, maleoyl dichloride,
glutaryl dichloride, adipoyl dichloride, suberoyl dichloride, azelaoyl
dichloride, sebacoyl dichloride, 1,10-decanedicarbonyl dichloride,
1,12-dodecanedicarbonyl dichloride, 1,16-hexadecanedicarbonyl
dichloride and the like; cycloaliphatic dicarboxylic acid dichlorides
such as cyclohexanedicarbonyl dichloride, cyclohexenedicarbonyl
dichloride and the like; aliphatic dicarboxylic acid dibromides such as
malonyl dibromide, succinyl dibromide, fumaroyl dibromide, maleoyl
dibromide, glutaryl dibromide, adipoyl dibromide, suberoyl dibromide,
azelaoyl dibromide, sebacoyl dibromide, 1,10-decanedicarbonyl

dibromide, 1,12-dodecanedicarbonyl dibromide, 1,16-
hexadecanedicarbonyl dibromide and the like; and cycloaliphatic
dicarboxylic acid dibromides such as cyclohexanedicarbonyl dibromide,
cyclohexenedicarbonyl dibromide and the like. Among them, malonyl
dichloride, succinyl dichloride, adipoyl dichloride, azelaoyl dichloride,
sebacoyl dichloride, malonyl dibromide, succinyl dibromide, adipoyl
dibromide, azelaoyl dibromide and sebacoyl dibromide are preferable.
[0017] On the other hand, as the compound represented by the
general formula (5) are mentioned catechol, resorcin and hydroquinone.
[0018] As the base used in the reaction of the compound represented
by the general formula (4) with the compound represented by the
general formula (5) are usually used organic bases such as pyridine, (3-
picoline, N-methylmorpholine, dimethylaniline, diethylaniline,
trimethylamine, triethylamine, tributylamine and the like.
[0019] When the compound represented by the general formula (4)
is reacted with the compound represented by the general formula (5), a
molar ratio of the compound represented by the general formula (4) to
the compound represented by the general formula (5) is usually 1:4 -
1:30.
[0020] When the compound represented by the general formula (4)
is reacted with the compound represented by the general formula (5), a
solvent may be used for the purpose of dissolving the starting
materials. As the solvent may be used the above-mentioned organic
bases as it is and other organic solvents not obstructing the reaction.
As the latter solvent is mentioned ether such as dimethyl ether,
dioxane or the like.
[0021] When the compound represented by the general formula (4)
is reacted with the compound represented by the general formula (5),
the reaction temperature is usually -20°C - 100°C.
[0022] The compound represented by the general formula (1) and
obtained from the above-mentioned reaction can be isolated from the
reaction mixture by a well-known method. There are mentioned a
method in which the organic base and the compound represented by the

general formula (5) used for the reaction and further an organic
solvent if it is used for the reaction are evaporated and dried by an
operation of a vacuum distillation or the like, a method in which a
poor solvent for the compound represented by the general formula (1)
is added to the reaction mixture to conduct re-precipitation, a method
in which a water and a water immiscible organic solvent are added to
the reaction mixture to extract into an organic phase, and so on.
Moreover, in some cases, it may be purified by recrystallization.
[0023] As the poor solvent for the compound represented by the
general formula (1) is usually used a water. Moreover, as the water
immiscible organic solvent are used esters such as ethyl acetate, butyl
acetate and the like; and ketones such as methyl isobutyl ketone,
diisobutyl ketone and the like.
[0024] When resorcin is used as the compound represented by the
general formula (5), a composition composed mainly of the compound
represented by the general formula (2) and comprising the compound
represented by the general formula (2) and the compound represented
by the general formula (3) can be obtained.
[0025] R in the general formula (3) is the same meaning as R in the
general formula (1), and n is an integer of 2-6.
[0026] For example, the composition obtained by using resorcin in
the above-mentioned reaction and comprises the compound represented
by the general formula (2) and the compound represented by the
general formula (3) usually includes 60-100 wt% of the compound
represented by the general formula (2), 0-20 wt% of the compound
represented by the general formula (3) wherein n is 2, 0-10 wt% of the
compound represented by the general formula (3) wherein n is 3, and
about 10 wt% in total of the compounds represented by the general
formula (3) wherein n is 4-6. The ratio of these compounds can be
controlled by adjusting a molar ratio of the compound represented by
the general formula (4) to resorcin.
[0027] The composition comprising the compound represented by
the general formula (2) and the compound represented by the general

formula (3) can be also isolated from the reaction mixture containing
them in the same manner as in the isolation method of the compound
represented by the general formula (1).
[0028] In case of the composition containing not less than 60 wt%
of the compound represented by the general formula (2), the humidity-
aged adhesion when being compounded with rubber and adhered is
improved. In view of the improvement of the humidity-aged adhesion,
the content of the compound represented by the general formula (2) is
more preferably 70-100 wt%, further preferably 80-100 wt%.
[0029] The compound according to the invention and the
composition containing such a compound as a main component have a
characteristic of easily mixing with a rubber component as compared
with resorcin or the RF resin. Therefore, the rubber composition
comprising the compound according to the invention and the
composition containing such a compound as a main component tends to
hardly cause the blooming as compared with the rubber composition
comprising resorcin or the RF resin. This is presumed due to the fact
that the compound according to the invention and the composition
containing such a compound as a main component are low in the
polarity as compared with resorcin and the RF resin. Furthermore,
the rubber composition comprising the compound according to the
invention and the composition containing such a compound as a main
component is excellent in the adhesion stability irrespectively of the
storage period. Therefore, the compound according to the invention
and the composition containing such a compound as a main component
are useful as an adhesion improver.
[0030]
The invention will be described in detail with reference to
the following examples, referential examples and comparative
examples, but the invention is not limited to these examples.
[0031] (Example 1)
A solution of 330.6 g (3.0 mol) of resorcin in 600.0 g of
pyridine is kept below 15°C on an ice bath, and 54.9 g (0.30 mol) of

adipoyl chloride is gradually dropped into the solution. After the
dropping, the temperature of the resulting reaction mixture is raised to
room temperature and left to stand over a whole day and night to
complete the reaction. From the reaction mixture is distilled off
pyridine under a reduced pressure, and the resulting residue is added
with 1200 g of water and cooled on ice to precipitate a deposit.
The precipitated deposit is filtered and washed with water, and the
thus obtained wet body is dried under vacuum to obtain 84 g of a
white-light yellow powder. The powder is treated by a liquid
chromatography provided with a preparative unit under the following
conditions to batch off an elute containing a primary component.
A crystal precipitated by the concentration of the elute is recovered by
filtration and dried under vacuum to obtain a crystal having a melting
point of 140-143°C. As a result of a HPLC analysis, this crystal is
bis(3-hydroxyphenyl) adipate having a purity of 98%.
[0032] The conditions of the preparative HPLC are shown as follows:
Column : Shim-pack PREP-ODS (made by SHIMADZU Corporation)
Column temperature : 25°C
Eluting solution : methanol/water mixed medium (85/15(w/w%))
Flow rate of eluting solution : 3 ml/min
Detector : UV detector (254 nm).
[0033] Moreover, the identification data of bis(3-hydroxyphenyl)
adipate are shown as follows:
Datum of MS Spectrum
EI(Pos.) m/z=330
Data of IR Spectrum
3436 cm-1 : hydroxyl group
2936 cm-1 : alkyl
1739 cm-1 : ester
Data of NMR spectra are shown in Table 1-1 and Table 1-2.


[0035] (Example 2)
As a result of HPLC analysis on 84 g of a powder obtained
by conducting the same reaction as in Example 1, a content of bis(3-
hydroxyphenyl) adipate in the powder is 89 wt%. The powder further
contains 7 wt% of a compound of n=2 in a compound represented by
the following formula (6) (hereinafter may be referred to as an
oligomer), 2 wt% of a compound of n=3 in the compound represented
by the formula (6), and 2 wt% of resorcin as a starting material.
The compound represented by the formula (6) is identified by LC-MS.


[0036] The measurement conditions of the MS spectrum are shown
as follows:
Range of mass : 200-2000 amu (1.98+0.02 sec)
Ionization method : ESI (Electrospray)
Mode : positive
Capillary : 3.15 kV
Cone : 35V
S. B. Tmp. : 150 °C
Deslv. tmp. : 400 °C
Multi : 650 V
N2 : 750 L/hr
n=2 : 551.1 [M+H]+, 568.2 [M+NH4] +
n=3 : 771.2 [M+H]+, 788.2 [M+NH4] +
n=4 : 1008.3 [M+NH4] +
n=5 : 1228.3 [M+NH4] +
[0037] The analytical conditions of the HPLC are shown as follows:
1. Analysis of bis(3-hydroxyphenyl) adipate and resorcin
Column : A-312 ODS from YMC Company
Column temperature : 40°C
Eluting solution : methanol/water = 7/3 (pH is adjusted to 3
with phosphoric acid)
Detection : UV (254 nm).
[0038] 2. Analysis of the oligomer
Column : A-312 ODS from YMC Company
Column temperature : 40°C
Eluting solution : acetonitrile/water = 8/2 (pH is adjusted to
3.5 with acetic acid)
Detection : UV (254 nm).
[0039] (Example 3)
The same procedure as in Example 1 is repeated except that
the amount of resorcin is 176.2 g (1.6 mol), the amount of pyridine is
400 g and the amount of adipoyl chloride is 73.2 g (0.40 mol) to obtain
118.6 g of powder. As a result of the HPLC analysis, the powder

contains 73.4 wt% of bis(3-hydroxyphenyl) adipate, 13.9 wt% of the
compound of n=2 represented by the formula (6), 3.0 wt% of the
compound of n=3 represented by the formula (6), 0.8 wt% of the
compound of n=4 represented by the formula (6), 0.2 wt% of the
compound of n=5 represented by the formula (6) and 2.9 wt% of
resorcin as a starting material.
[0040] (Example 4)
A solution of 440.4 g (4.0 mol) of resorcin in 405.0 g of
pyridine is kept below 15°C on an ice bath, and 62.0 g (0.4 mol) of
succinyl dichloride is gradually dropped into the solution. After the
dropping, the temperature of the resulting reaction mixture is raised to
room temperature and left to stand over a whole day and night to
complete the reaction. From the reaction mixture is distilled off
pyridine under vacuum, and the resulting residue is added with 1800 g
of water and cooled on ice, during which the liquid becomes clouded
wholly and separates into two phases. The extraction is carried out
by adding 200 g of water and 600 g of ethyl acetate to an oil phase.
The resulting organic phase is washed five times with cold water and
then dried with magnesium sulfate. Thereafter, ethyl acetate is
distilled off to obtain a viscous body, which is crystallized by adding
500 g of toluene, filtered, washed with toluene and then subjected to
sludging twice with 1L of water. The resulting wet body is dissolved
into 100g of methanol, re-precipitated by adding 1L of water, filtered,
washed and dried to obtain 82.3 g of light yellow powder. As a result
of the HPLC analysis, a primary component of the powder is found to be
a component having 91.0 area%. Also, the powder contains 0.7 wt%
of resorcin. As a result of structural analysis, the primary component
of the powder is found to be bis(3-hydroxyphenyl) succinate.
[0041] Moreover, identification data of bis(3-hydroxyphenyl)
succinate are shown as follows:
Datum of MS Spectrum
EI(Pos.) m/z=302
Data of IR Spectrum


[0043] (Example 5)
A solution of 330.3 g (3.0 mol) of resorcin in 303.7 g of
pyridine is kept below 15°C on an ice bath, and 71.7 g (0.3 mol) of
sebacoyl dichloride is gradually dropped into the solution. After the
dropping, the temperature of the resulting reaction mixture is raised to
room temperature and left to stand over a whole day and night to
complete the reaction. From the reaction mixture is distilled off
pyridine under vacuum, and the resulting residue is added with 250 g
of water and cooled on ice to precipitate a deposit. The precipitated
deposit is filtered and washed with water, and the resulting wet body is
dried under vacuum to obtain 102.8 g of a white-light yellow powder.
As a result of the HPLC analysis, a primary component of the powder is

found to be a component having 98.7 area%. Also, the powder contains
0.2 wt% of resorcin. As a result of structural analysis, the primary
component of the powder is found to be bis(3-hydroxyphenyl) sebacate.
[0044] Moreover, identification data of bis(3-hydroxyphenyl)
sebacate are shown as follows:
Datum of MS Spectrum
EI(Pos.) m/z=386
Data of IR Spectrum
3380 cm-1 : hydroxyl group
3000-2800 cm-1 : long chain alkyl
1732, 1749 cm-1 : ester
Data of NMR spectra are shown in Table 3-1 and Table 3-2.


[0046] (Reference Examples 1-5)
Each of the compositions produced in Examples 1-5 is used
as a test compound and mixed and milled with rubber according to a
compounding recipe shown in Table 4 to prepare an unvulcanized
rubber composition, and then the resistance to blooming, Mooney
viscosity, adhesiveness just after the compounding and adhesiveness
after the leaving of compounded rubber are measured and evaluated.
The results are shown in Table 4.
[0047] (Resistance to blooming)
After the unvulcanized rubber composition is stocked at
40°C for 7 days, it is visually observed whether the compounding
ingredient is separated out on the surface of rubber, which is judged by
O, ∆ and x.
O : The compounding ingredient is not separated out on the
surface.
∆ : The compounding ingredient is partially separated out on the
surface.
x : The compounding ingredient is separated out on the whole
surface.
[0048] (Mooney viscosity)
ML(1+4)130°C of the unvulcanized rubber composition is
measured according to JIS K6300-2001. The smaller the numerical
value, the better the result.
[0049] (Adhesion test)
Steel cords (1x5 structure, wire diameter : 0.25 mm) plated
with brass (Cu : 63 mass%, Zn : 37 mass%) are arranged in parallel to
each other at an interval of 12.5 mm and coated with each of the
rubber compositions from both sides thereof and immediately
vulcanized at 160°C for 15 minutes to prepare a sample having a width
of 12.5 mm. After the steel cord is pulled out from the sample
according to ASTM-D-2229 for the following adhesiveness, the rubber
coated state is visually observed and represented by a value of 0-100%
as an indicator of the adhesiveness. The larger the value, the better

the property. The initial adhesion is measured just after the
vulcanization. The humidity-aged adhesion is measured by aging at
70°C and a humidity of 100% RH for 4 days after the vulcanization.
[0050] (Test for adhesion stability)
A steel cord-rubber composite body of an unvulcanized state
formed by coating steel cords with each of the rubber compositions is
left to stand in a constant temperature and humidity chamber of 40°C
and 80% RH for 7 days and then vulcanized at 160°C for 15 minutes to
measure an initial adhesion as an indicator of the adhesion stability.
[0051] (Comparative Example 1)
A rubber composition is prepared according to the same
compounding recipe as in the reference examples except that the compo-
sition according to the invention is not used as a test compound and
the properties thereof are evaluated. The results are shown in Table 4.
[0052] (Comparative Example 2)
A rubber composition is prepared according to the same
compounding recipe as in the reference examples except that 2 parts
by mass of resorcin is compounded in the base rubber formulation as a
test compound and the properties thereof are evaluated. The results
are shown in Table 4.
[0053] (Comparative Example 3)
A rubber composition is prepared according to the same
compounding recipe as in the reference examples except that 2 parts
by mass of RF resin is compounded in the base rubber formulation as a
test compound and the properties thereof are evaluated. The results
are shown in Table 4. Moreover, the RF resin is prepared by the
following method.
[0054] At first, 1100 g of water, 1100 g (10 mol) of resorcin and
1.72 g (10 mmol) of p-toluenesulfonic acid are charged into a four-
necked flask equipped with a cooling tube, a stirrer, a thermometer,
a dropping funnel and a tube for introduction of nitrogen, and then
heated to 70°C. 477g (5.9 mol) of a 37% formalin solution is added
dropwise over 2 hours and the temperature is kept for 5 hours to

complete the reaction. After the completion of the reaction, 4g of an
aqueous solution of 10% sodium hydroxide is added and neutralized,
and thereafter the cooling device is substituted with a Dean-Stack type
reflux condenser. Then, the temperature is raised to 150°C while
distilling off water, and further water is removed under a reduced
pressure of 20 mmHg over 1 hour to obtain the RF resin. The thus
obtained RF resin has a softening point of 124°C and a residual
resorcin content of 17%.
[0055] (Comparative Example 4)
A rubber composition is prepared according to the same
compounding recipe as in the reference examples except that 2 parts
by mass of a mixed polyester described in JP-A-7-118621 is
compounded in the base rubber formulation as a test compound and the
properties thereof are evaluated. The results are shown in Table 4.
Moreover, the mixed polyester is prepared according to Example 1 of
the above-described publication.
[0056] Into a 300 ml four-necked flask equipped with a reflux
condenser and a thermometer are charged 108.9 g (0.99 mol) of
resorcin, 131.4 g (0.90 mol) of adipic acid, 222.0 g (2.175 mol) of
acetic anhydride and 0.54 g (0.5 wt % to resorcin) of pyridine, and the
inside of the flask is purged with nitrogen, and then the mixture is
stirred at room temperature for 15 minutes and heated to 100°C and
acetylated at this temperature for 2 hours. Thereafter, the system is
heated while distilling off a by-product acetic acid from the system,
and maturated at 140°C for 1 hour and further at 240°C for 2 hours.
Then, the maturation is continued at 240°C under a reduced pressure
(50 mmHg). The resulting reaction mixture is discharged onto a
porcelain dish to obtain 195.6 g of ocher candy-like body. The candy-
like body is gradually crystallized by kneading with a glass rod. As a
result of the analysis, the crystal contains 0.1 wt% of resorcin, 0.5 wt%
of resorcin monoacetate and 0.8 wt% of resorcin diacetate. As a
result of the measurement on the molecular weight through GPC, the
weight-average molecular weight is about 30000 (conversion to PS).

We claim:
1. A compound represented by the following general formula (2):

(Wherein R represents a divalent aliphatic group having a carbon
number of 1-16).
2. A compound as claimed in claim 1, wherein R in the general
formula (2) is an alkylene group having a carbon number of 2-10.
3. A compound as claimed in claim 1, wherein R in the general
formula (2) is ethylene group butylene group or octylene group.
4. A composition comprising 60-100 wt % of the compound
represented by the general formula (2), 0-20 wt % of a compound

represented by the following general formula (3) in which n is 2, 0-
10 wt % of a compound represented by the following general formula
(3) in which n is 3 and 0-10 w % of a compound represented by the
following general formula (3) in which n is 4-6:

(Wherein R represents a divalent aliphatic group having a carbon
number of 1-16),

(wherein R is a divalent aliphatic group having a carbon number of 1-
16, and n is an integer 2-6).

5. A composition as claimed in claim 4, wherein R in the general
formula (2) and the general formula (3) is an alkylene group
having a carbon number of 2-10.
6. A composition as claimed in claim 4, wherein R in the general
formula (2) and the general formula (3) is ethylene group,
butylenes group or octylene group.

This invention provides a compound represented by the following
general formula (1) and capable of suppressing the blooming, which
is observed in the compounding of the resorcin or the RF resin, as far
as possible while maintaining the workability and high humidity-aged
adhesion of the rubber composition obtained by compounding with
rubber, reducing the deterioration of the adhesiveness during the
storage of the rubber composition and stably developing the
adhesiveness as well as the composition containing the above-
mentioned compound as a main component:

(Wherein R represents a divalent aliphatic group having a carbon
number of 1-16).