Note: Descriptions are shown in the official language in which they were submitted.
1333430
~ 1- 72736-36D
This is a divisional application of Canadian Patent
Application Ser. No. 613,801 filed September 27, 1988.
RACXGROUND OF TH~ INV~NTION
This invention relates to thermoplastic resin
compositions which are mainly composed of polyarylate resins,
polyamide resins and epoxy resins and have excellent impact
strength, heat and solvent resistances and moldability.
Compositions made of polyarylate resins and polyamide
resins have good heat and solvent resistances and good
moldability. For instance, Japanese Patent Publication No.
56-14699 discloses a resin composition made of a polyarylate
and a polyamide, and Japanese Laid-open Patent Application
No. 52-100552 discloses a resin composition which is made of
a polyarylate-based resin composed of a mixture of a
polyarylate and polyethylene terephthalate, and a polyamide.
Since polyarylates and polyamides are substantially
immiscible with each other, the composition obtained by melt
kneading exhibits a phase separation structure wherein the
adhesion strength at the interface between the polyarylate
phase and the polyamide phase is so weak, with the attendant
disadvantage of the resulted composition that the impact
strength becomes small, thus leading to brittleness.
Attempts have been made to improve the impact strength of
the resin compositions made of polyarylates and polyamides by
addition, as the third ingredient, of a miscibility improver
or an impact strength improver. For instance, in Japanese
Laid-open Patent Application, there is used an N-substituted
amido-containing polymer as the third ingredient. As the
third ingredient, there are used polyalkylene phenylene
esters containing a group of sulfonate salt in Japanese Laid-
open Patent Application No. 59-105050, glycidyl group-
containing olefin copolymers in Japanese Laid-open Patent
- Application No. 61-183353, mixtures of epoxy group-containing
- 1333430
-2- 72736-36D
ethylene copolymers and acid anhydride-containing olefin
copolymer in Japanese Laid-open Patent Application Nos. 62-
277462 and 62-283146.
However, the resin compositions disclosed in the Japanese
Laid-open Patent Application Nos. 58-67749 and 59-105050 are
far from satisfactory in improving the impact strength. With
the resin compositions disclosed in the Japanese Laid-open
Patent Application Nos. 61-183353, 62-277462 and 62-283146,
the effect of improving the impact strength starts to develop
when the content of the third ingredient exceeds about 5 wt%.
For obtaining satisfactory impact strength, the third
ingredient has to be added in amount ranging from 10 to
30 wt%. Such resin compositions are unfavorably apt to
undergo thermal decomposition in the cylinder of an extruder
or injection molding machine, with attendant disadvantages
such as gelation, coloration, a ~owering of mechanical
strength, and defects in appearance of the resultant moldings
such as flow mark, silver streak and silver blister.
Moreover, since olefin polymers are formulated in large
amounts, the resulting resin compositions is improved in the
impact strength but is considerably lowered with respect to
the tensile strength, bending strength, modulus of elasticity
and heat resistance.
A resin compositions made of a polyarylate resin, a
polyethylene terephthalate resin and a polyamide resin has
excellent heat and solvent resistances and moldability and is
disclosed, for example, in Japanese Patent Publication No.
58-50260. However, this resin composition has such problems
as involved in the compositions made of polyarylate resins
and polyamide resins. More pa~ticularly, although
polyarylates and polyethylene terephthalate are miscible with
each other, polyamide is incompatible with these resins. The
composition obtained by melt kneading of these resins
exhibits a phase separation structure wherein the adhesion
strength at the interface between the polyarylate and
1333~30
- 3 - 72736-36D
polyethylene terephthalate phases and the polyamide phase is weak,
so that the composition has inconveniently a small impact strength
and is brittle.
In order to improve the impact strength of the above
composition, Japanese Laid-open Patent Application No. 52-100552
proposed an improved process, but satisfactory mechanical strength
has not yet been obtained.
Japanese Patent Public Disclosure NQ. 187761/1987
discloses a thermoplastic resin composition comprising polycarbon-
ate, poly(ester carbonate) and polyamide, in which bisphenol A
diglycidyl ether is contained as a compatibilizer having an epoxy
group.
However, the composition disclosed in Japanese Patent
Public Disclosure No. 187761/1987 is chiefly composed of poly-
carbonate. Polycarbonate is decomposed easily by heat in the
presence of even a small quantity of basic substance. In kneading
process of polycarbonate and polyamide, therefore, polycarbonate
is decomposed during thermal melting caused by the amide bond and
terminal amino group of polyamide. In addition, since a monomer
such as bisphenol A diglycidyl ether is used as the compatibilizer,
it is difficult to knead such a liquid monomer with resins which
are solid at normal temperatures.
SUMMARY OF THE INVENTION
An object of the invention is to provide a resin
composition which has remarkably improved impact strength without
a sacrifice of good solvent and heat resistances, good moldability,
1333~30
- - 4 - 72736-36D
high rigidity and good thermal stability inherent to thermoplas-
tic resin compositions predo~;~Antly made of polyarylates and
polyamides.
According to the present invention, there is provided
a thermoplastic resin composition which comprises:
[A] 100 parts by weight of a resin mixture consisting
essentially of not less than 10 wt% of a polyarylate resin, not
less than 20 wt% of a polyamide resin and from 3 to 60 wt% of
polyethylene terephthalate resin; and
[B] from 0.1 to 15 parts by weight of an epoxy resin of
the following formula:
133~0
72736-36D
~ ~ R I ~
C~ - CH-CH2-(-o ~ X ~ 0H
11 R R
--~X~ o
R R R 11
(whereln X represents a dlrect bond, a lower alkylene
group havlng frou 1 to ~ carbon atou~, a lover alkylldene group
havlng up to ~ carbon aton~,
;
-SO2-, -O- or -S-, where a part or all of the hydrogen
atoms of X may be substituted with halogen atoms when X represents
any hydrocarbon defined above, R's independently represent a
hydrocarbon atom, a halogen atom, a lower alkyl group having from
1 to 4 carbon atoms, and n is an integer of 1 or over).
DETAILED DESCRIPTION OF THE INVENTION
The polyarylate resin used in the present invention is
prepared from a bisphenol and/or its derivative, terephthalate
acid and/or its derivative and isophthalic acid and/or its deri-
vative and consists of these three ingredients.
1333430
- b - 72736-36D
Terephthalic acid and isophthalic acid have, respec-
tively, the following formulae
HOC ~ -COH ~ - COH
O O , O
HOC
The derivatives of terephthalic acid and isophthalic
acid include acid halide compounds such as terephthalic acid
dichloride, isophthalic acid dichloride and the like, and diester
compounds such as dimethyl terephthalate, dimethyl isophthalate,
diphenyl terephthalate, diphenyl isophthalate and the like.
Terephthalic acid, isophthalic acid and derlvatives
thereof may be substituted, at part or all of the hydrogen atoms
of the phenylene group, with a halogen atom or a lower alkyl group.
The bisphenols and derivatives thereof are represented
by the following formula [2~
R R R R
HO ~ Y ~ OH [2]
R R
wherein Y represents a lower alkylene group havino fro~
1 to 4 carbon atoms, an alkylidene group having up to 4 carbon
atoms,
1333130
- 7 - 72736-36D
CN
-CH- -C-
, CN
-SO2-, -O-, -S- or -C-, wherein part or all of the
o
hydrogen atoms in Y, if any, may be substituted with a halogen
atom, and R's independently represent a hydrogen atom, a halogen
atom or a lower alkyl group having from 1 to 4 carbon atoms.
Examples of the bisphenols of the formula [2] include
2,2-bis(4-hydroxyphenyl)propane, bis(4-hydroxyphenyl)methane,
4,4'-dihydroxydiphenyl ether, bis(4-hydroxyphenyl)sulfide,
bis(4-hydroxyphenyl)sulfone, bis(4-hydroxyphenyl)ketone,
bis(4-hydroxy-3-methylphenyl)methane, bis(4-hydroxy-3,5-dibromo-
phenyl)methane, l,l-bis(4-hydroxyphenyl)ethane, 2,2-bis(4-hydroxy-
3-methyl-phenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)
propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis
(4-hydroxy-3,5-dibromophenyl)propane, 2,2-bis(4-hydroxyphenyl)
butane, bis(4-hydroxyphenyl)phenylmethane, bis(4-hydroxyphenyl)
diphenylmethane, bis(4-hydroxyphenyl)difluoromethane and the like.
Of these, 2,2-bis(4-hydroxyphenyl)propane which is usually called
bisphenol A is preferred because of the ease in availability of
starting materials. If necessary, a small amount of aromatic
dihydroxy compounds such as, for example, 4,4'-bisphenol, 2,6-
: 1333~30
72736-36D
naphthale~ediol, hydroquinone, chlorohydroquinone and the like,
may be used in combination with the bisphenols.
The polyaryl resins may be prepared by any methods
including an interfacial polymerization method, a solution poly-
merization method and a melt polymerization method.
The polyamide resins used in the present invention are
those of the following general formula,
~ C - R - NH t or t C - R - C - N H - R3 - NH t
ll ll ll
O O O
wherein Rl, R2 and R3 are independently an alkylene group having
from 2 to 16 carbon atoms, and are prepared by condensation
reaction between diamines and dibasic acids, self-condensation
of amino acids, or ring opening polymerization of lactams.
For instance, there can be mentioned nylon 6 prepared
from ~-caprolactam or ~-aminocaproic acid, nylon 6-6 prepared
from hexamethylenediamine and adipic acid, nylon 6-10 prepared
from hexamethylenediamine and sebacic acid, nylon 6-12 prepared
from hexamethylenediamine and dodecanoic acid, nylon 11 prepared
from ~-aminoundecanoic acid, nylon 12 prepared from ~-laurolactam
or ~-aminododecanoic acid, nylon 4-6 prepared from 1,4-diamino-
butane and adipic acid, and the like. In view of the easy avail-
ability of the starting materials, nylon 6 and nylon 6-6 are
preferred.
The epoxy resin used in the present invention is re-
presented by the following general formula:
1333~30
- 9 - 72736-36D
R R R R
C ~ /CH CH2-~ ~ X ~ OCH21HCH2 t~n
R R R R
R R R R
-O--~X_~OCH2CH fH2 [1]
R R R R
wherein X represents a direct bond, a lower alkylene
group having from 1 to 4 carbon atoms, an alkylidene group having
up to 4 carbon atoms,
,~
-CH- CN ~
--C-- --C--
, CN
-S02-, -O-, or -S- wherein part or all of the hydrogen
atom~ of X may be substituted with halogen atoms when X
represents any hydrocarbon defined above, R's independently re-
present a hydrogen atom, a halogen atom, a lower alkyl group having
from 1 to 4 carbon atoms, and n is an integer of 1 or over. This
epoxy resin is obtained by a bisphenol and an epihalohydrin such
as epichlorohydrin. Examples of the bisphenol are those of the
formula [2] set forth above with respect to the polyarylate resin.
Of these, 2,2-bis(4-hydroxyphenyl)propane or bisphenol A is
1333430
- 10 - 72736-36D
preferred because of the ease in availability of the starting
materials.
In the formula ~1], n which indicates the number of
the repeating units in the formula should be 1 or over. If n is
equal to zero, the adverse influence of the terminal epoxy group
is apt to develop, with the tendency that the resultant resin
composition is gelled, colored or decomposed. Especially, the
melting temperature and viscosity increase considerably and thus,
the molding becomes difficult. In order to bring out the effect
of satisfactorily improving the impact strength, it is preferred
that the terminal epoxy groups and the repeating polyether polyol
units are present at an appropriate ratio. In this sense,a pre-
ferred range of n is up to 28, more preferably from about 6 to 20.
A preferred range of epoxy equivalents is from about 1000 to 3000
for bisphenol A-type epoxy resins.
The epoxy resins used in the present invention may
contain, as copolymerized, a small amount of diols other than
bisphenols, including aromatic diols such as 2,6-naphthalenediol,
hydroquinone and the like, and aliphatic diols such as 1,4-
butanediol, propylene glycol, ethylene glycol and the like.
The polyethylene terephthalate resin used in the
invention is one which is prepared, by any known technique, from
terephthalic acid and/or its derivative and ethylene glycol.
The polyarylate resin, polyethylene terephthalate
resin and polyamide resin are, respectively, used in amounts of not
less than 10 wt%, from 3 to 60 wt%, and not less than 20 wt%,
1333~3~
- 11 - 72736-36D
_
each based on the total amount of these three resins. If the
amount of the polyarylate resin is less than 10 wt%, the heat
resistance and impact strength of the resultant resin composition
become low. If the amount of the polyamide resin is less than
20 wt%, the moldability and solvent resistance are lowered. If
the amount of the polyethylene terephthalate resin is less than
3 wt%, the moldability and rigidity (modulus of elasticity) of the
resultant composition are lowered. Over 60 wt%, the heat resis-
tance and impact strength are lowered.
An increasing amount of the polyarylate component
results in an increase in the impact strength and heat resistance
of the resultant composition. When the polyamide component in-
creases in amount, better moldability and solvent resistance are
obtained. If the polyethylene terephthalate component increases
in amount, the moldability becomes better with an increase in
rigidity. A preferable composition capable of imparting well-
balanced properties such as heat resistance, impact strength,
moldability, rigidity and solvent resistance comprises from 15 to
45 wt% of the polyarylate resin, from 45 to 65 wt% of the poly-
amide resin, and from 7 to 35 wt% of the polyethylene terephthalate.
The amount of the epoxy resin is generally in the
range of from 0.1 to 15 parts by weight per 100 parts by weight of
the mixture of the polyarylate resin, polyamide resin and poly-
ethylene terephthalate resin. If the amount is less than 0.1 part
by weight, the impact strength is not improved satisfactorily.
Over 15 parts by weight, the resultant composition lowers in heat
133~130
~ - 12 - 72736-36D
resistance, and the melting temperature and viscosity increase,
making it difficuIt to mold such a composition. A preferable
amount is in the range of from 2 to lO parts by weight.
For the production of the composition of the inven-
tion, any method of melt kneading the polyarylate resin, the
polyamide resin, polyethylene terephthalate and the epoxy resin
may be used without limitation. For instance, the melt kneading
may be carried out by use of a two-roll mill, Banbury mixer,
single-screw extruder, twin-screw extruder and the like. Alter-
natively, while kneading in an in]ection molding machine, the
composition may be molded. Preferably, the single or twin-screw
extruder of the high kneading type is used for kneading and
molding. The kneading order of the respective ingredients for
obtaining the composition of the invention is not critical. For
instance, the polyarylate, polyamide, polyethylene terephthalate
and epoxy resin may be simultaneously kneaded. Alternatively, two
or more of the four components may be first kneaded, to which the
other components are subsequently added. The optimum kneading
order is such that the polyarylate and polyethylene terephthalate
are first melt kneaded, followed by melt kneading the mixture,
polyamide and epoxy resins.
Additives and/or fillers may be further added to the
resin composition of the invention. The additives may be anti-
oxidants and thermal stabilizers such as copper halides, hindered
phenols and the like, phosphorus working stabilizers, benzo-
triazole and hindered amine light stabilizers, plasticizers such
1333~30
- 13 - 72736-36D
as paraffins, higher fatty acids and esters thereof, metal salts
and the like, lubricants such as silicone resins, fluorine resins
and the like, flame retardants such as decabromodiphenyl ether,
tetrabromobisphenol A, tetrachlorobisphenol A, aluminium
hydroxide, antimony trioxide, ammonium phosphate, tricresyl
phosphate, triethyl phosphate and the like, pigments, dyes and
the like. The fillers may be talc, calcium carbonate, mica,
wollastonite, ferrite, magnet powder of rare earth elements, glass
fibers, carbon fibers, asbestos fibers, metallic fibers, aramide
fibers, potassium titanate whiskers, and the like.
EXAMPLES
The present invention is more particularly described
by way of example, which should not be construed as limiting the
present invention. Comparative examples are also shown.
First, starting materials used in the examples and
comparative exampes are illustrated.
1. Polyarylate resin
PAR-l: polyarylate resin obtained from a 1:1 mixture
of terephthalic acidand isophthalic acid and bisphenol A(U-
Polymer U-100, available from Unichika ~o., Ltd.). The inherent
viscosity was 0.65 when determined using a solvent of phenol and
tetrachloroethane at a ratio by weight of 60:40 at a concentra-
tion of 0.25 g/dl at 23C.
2. Polyamide resins (PA-l to PA-2)
PA-l: nylon 6 (Amiran** CM1017, available from Toray
Limited).
**Trade-mark
1333~30
14 - 72736-36D
PA-2: nylon 6-6 (A~iran CM3001, available from Toray
Limited).
3, Third Ingredients (CP-l to CP-8)
CP-l to CP-6: epoxy resins (available from Danippon
Ink and Chemicals, Inc.).
CH
CH~ - CHCH2 (
O CH3
-CH2-~HCH2 )n ~ C -
CH3
~ OCH2 CH / CH2
Abbrevia- Commercial Epoxy Approximate Melting
tion Name Equiva- Number of n Point
lent* (C)
CP-l Epichlon**840180 n - 0 liquid~900
poises at 25C)
CP-2 Epichlon 1050450 n - 2 70
CP-3 Epichlon 4050955 n ~- 5 - 6 102
CP-4 Epichlon 70501809 n - 12 130
CP-5 Epichlon 90552600 n - 17 152
CP-6 Epichlon 91554070 n - 28 155
**Trade-mark
1333~3~
_,
- 15 - 72736-36D
*) The epoxy equivalents in the epoxy resin was
quantitatively determined by titration with perchloric acid
to obtain the weight (g) of the resin per equivalent of the
epoxy group.
CP-7: phenoxy resin (phenoxy PKHH, available from Union
Carbide Co., Ltd.) H3
:H~-:HCH2 ~o ~ .
~H ~H ;H,
:H~
._ OCH2;HCH2 ~tnO~J
~H HJ
OCH2CHCH~
~_v~ I ~ n T 1 0 0
OHOH
CP-8: Epichlon 9055 whose terminal epoxy groups were
modified with diethanolamine
(HOCH2CH2)2N-CH2:HCH2 1~0
~H
H. ~ .H~
_ ~ OCH2,HCH2 ~no ~ J ~ OCH2:HCH2-N(CH2CH20H)2
:HJ ~H ,HJ ~N
n ~ 1 7
4. Polyethylene terephthalate resin (PE-1)
(PET resin TR-4550BH, available from Teijin Co., Ltd.).
The inherent viscosity was 0.70 as determined in the same
manner as with the polyarylate.
The physical properties were evaluated according to the
following methods.
1) Tensile test:the measurement was made according to
ASTM D-638 at a pulling speed of 50 mm/minute to determine a
tensile break strength, a tensile modulus and a tensile break
energy (energy required before breakage).
1333430
`~ - 16 - 72736-36D
2) Izod impact test: th.e measurement Was m.ade according
to ASTM D-256 using a thickness of 1/8 inch.es as notchéd.
3) Heat distortion tempera.ture: after annealing at 150 QC
for 3 hours, the measurement was made according to ASTM D-648
at a thickness of 1/8 inches at a load of 18.6 kg.cm2.
4) Temperature at which the melt viscosity reaches
10,000 poises: the Koka-type flow tester CFT-500, made by-
Shimadzu Corporation, was ùsed to successively measure the vis-
cosity of resin by the use of a 0.5 mm~ x 1.0 mm nozzle under
conditions of a load of 10 kg and a heating rate of 6C/minute
thereby determining a temperature at which the melt viscosity
reaches 10,000 poises. This is a kind of criterion for moldability
of the resin and a criterion for the degree as to how the gelation
reaction proceeds. More particularly, when. the tempera.ture is
lower, a less degree of gelation proceeds with more ea.se in
molding.
Examples 1 to 6 and Comparative Examples 1 and 2
60 parts by weight of a polyarylate resin (PAR-l) and
40 parts by weight of a polyethylene terephthalate resin (PE-l)
were mixed and dried at 110C for 5 hours. Thereafter, the
mixture was melt kneaded and pelletized by means of a twin.-
screw extruder at a cylinder temperature of 300C. 50 parts by
weight of the mixture of the polyarylate resin and polyethylene
terephthalate resin and 50 parts by weight of nylon 6 (PA-1) were
mixed, to which an epoxy resin (CP-5) was added in different amount
per 100 parts by weight of this mixture. ~fter drying the
respective mixtures, each mixture was melt kneaded and pelletized
1333~30
~ - 17 - 72736-36D
by means of a twin-screw extruder at a cylinder temperature of
270C. The resultant pellets were molded by means of an injection
molding machine into l/2 x 1/5 x ll8 inch elongated test pieces
and dumbbell specimens for ASTM tensile test. The physical
properties of the respective moldings were evaluated. The results
are shown in Table 1.
From Table 1, it wiIl be seen that the addition of
small amounts of the epoxy resin results in a remarkable increase
in the Izod impact strength and the tensile break energy. However,
when the content of the epoxy resin exceeds 15 parts by weight,
not only the impact strength and the heat distortion temperature
are lowered, but also the moldability is worsened.
Examples 7 to 11 and Comparative Examples 3 to 8
A polyarylate resin (PAR-l), a polyethylene terephthal-
ate resin (PE-l), nylon 6 (PA-l) and an epoxy resin (CP-5) were
mixed in different mixing ratios indicated in Table 2, followed
by pelletization in the same kneading order and manner as in Ex-
ample 1, injection molding and evaluation of the physical proper-
ties. The results are shown in Table 2.
Examples 12 to 18 and Comparative Examples 9 to 13
Starting materials at different mixing ratios as
indicated in Table 3 were pelletized in the same manner as in
Example 1 wherein the polyarylate resin and polyethylene terephthal-
ate were initially melt kneaded, to which the other two ingredients
were added and melt kneaded for pelletization, followed by in-
~ection molding and evaluation of the physical properties. The
results are shown in Table 3.
13~3 130
-- 18 -
72736--36D
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133343~
- 19 - 72736-36D
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72736-36D
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I333~3~
- 21 - 72736-36D
The resin composition according to the present invention
has especially good moldability, heat resistance, impact
strength, solvent resi~tance and high rigidity and are thus
well balanced in the physical properties. When making use of
these characteristic features, the resin composition of this
aspect has utility optimumly a~ plastics for outer plates of
automobile having the capability of paint baking, switches,
knobs, housings of electronic and electric instruments which
are exposed to intense heat, containers and housing
instruments which are exposed to chemical compounds.
