Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
2~3~2
Impact Resistant Polycarbonate Mouldiny C~positions
This invention relates to thermoplastic moulding compositions
composed of polycarbonates with high heat distortion
temperatures, graft polymers and hydrogenated, randomly
structured nitrile rubbers or ethylene/vinyl acetate co-
polymers and to the use of the thermoplastic moulding
compounds for the manufacture of moulded products of
various kinds.
Thermoplastic moulding compositions obtained from polycarbonates
with high heat distortion temperatures and modifiers for
improving the toughness of the polycarbonates are known and
are described in German Patent application P 3 833 953.6 A
Moulded articles produced from these moulding compounds,
however, generally have insufficient toughness at low
temperatures and resistance to organic solvents so that they
are only of limited use for example for the external parts
of motor vehicles.
It is therefore an object of the present invention to
avoid the above described disadvantages of these moulding
` 20 compounds and to provide improved thermoplastic moulding
compounds based on polycarbonates having high heat
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distortion temperatures.
The present invention therefore relates to thermoplastic
mould-ng ~ompositions containing
A) from 20 to 97 parts by weight, preferably from 40 to
95 parts by weight, of a polycarbonate based on
substituted dihydroxydiphenyl cycloalkanes corres-
ponding to formula (I)
R~ Rl
H ~ H (I) ,
R~ ~4
wherein
Rl and R2 denote, independently of one another,
hydrogen, halogen, preferably chlorine or bromine,
Cl to Cg alkyl, Cs to C6 cycloalkyl, C6 to C10
aryl, preferably phenyl, and C7 to Cl2 aralkyl,
preferably phenyl-Cl to C4 alkyl, in particular
benzyl,
m denotes an integer with a value from 4 to 7,
preferably 4 or 5,
R3 and R4 are selected individually for each X and
denote , independently of one another, hydrogen
or Cl to C6 alkyl, and
X denotes carbon, under the condition
that on at least one carbon atom denoted by X,
both R3 and R4 are alkyl groups,
-2-
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B) from 3 to 80 parts by weight, preferably from 5 to 60
parts by weight, of a graft polymer of resin-forming
monomers (graft monomers) on a rubber (graft basis) and
C) from 1 to 50 parts by weight, preferably from 3 to 40
parts by weight, of a hydrogenated, randomly
structured nitrile rubber, A ~ s ~ C adding up in each
case to 100 parts by weight.
Ethylene/vinyl acetate copolymers may be used instead of
the nitrile rubber of component C). The quantity of the
ethylene/vinyl acetate copolymers is from 1 to 50 parts by
weight, preferably from 3 to 40 parts by weight, the sum
of A ~ B + C adding up to 100 parts by weight.
In formula (I), R3 and R4 are preferably both alkyl on
one or two of the carbon atoms denoted by X, more preferably
on only ~ne carbon atom X. The preferred alkyl group is
methyl; the X atoms in the a position to ~he diphenyl-
substituted carbon atom (C-l) are preferably not dialkyl
substituted but alkyl disubstitution is preferred in the
~ position to C-l.
Dihydroxydiphenyl cycloalkanes having 5 or 6 ring carbon
atoms in the cycloaliphatic group (m = 4 or 5 in formula
(I)) are preferred, e.g. the diphenols corresponding to
the formulae (IIa) to (IIc):
Rl Rl
H ~ ~ ~ ~IIa~
R2 ~ ~3 R2
H3CCH~
-3-
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Rl Rl
}~o~ ~ c - ~OH (IIb)
R2 H3C~<CH3 R2
H3C C~3
Rl R
Hu 5 z~ ;r H ( I Ic )
CH3
C~3;
among which, 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethyl-
cyclohexane (formula IIa with Rl and R2 both denoting H)
is particularly preferred.
The substituted dihydroxydiphenyl cyc].oalkanes corres-
ponding to formula (I) and the correspondirlg polvcarbonates
(component A) may be prepared according to German Patent
lS application DE-A 38 32 396. The polycarbonates used are
high molecular weight, tfiermoplastic, aromatic poly-
carbonates with weight average molecular weights Mw of at
least 10,000, preferably from-20,000 to 300fO00.
.
According to the invention there may be used either one
diphenol corresponding to formula (I) to form homopoly-
carbonates or several diphenols corresponding to formula (I) ~.
to form copolycarbonates.
;~ :
Further, the diphenols corresponding to formula (I) may
also be used as mixtures with other known diphenols (such
25 as those described, for example, in D~-A 38 32 396) for the
preparation of high molecular weight, thermoplastic
aromatic polycarbonates used as component A.
Known branching agents may be used for the preparation of ~:
_4_ .
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.
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.
2~3r3~ ~2
t.~e polycarbonates put into the process, as well as chain
terminators for regulating the molecular weight; see in this
connection again DE-A 38 32 396. The said DE-A 38 32 396
also mentions the quantities of other diphenols which may be
used as well as the quantities of chain terminators and
branching agents.
The graft polymers used as component B may be polymers of
resin-forming monomers prepared in the presence of rubbers.
They include, for example, graft copolymers with rubbery
elastic properties which have been prepared from at least
two of the following monomers: chloroprene, butadiene~l,3),
isoprene, styrenes, acrylonitri~es, ethylene, propylene,
vinyl acetate and (meth)acrylic acid esters having 1 to 8
carbon atoms in the alcohol component; in other words,
polymers such as those described, for example, in "Methoden
der Organischen Chemie" (Houben-Weyl), Volume 14/1, Georg
Thienle--Ver~ag, Stuttgart 1961, pacles 393 to 406, and in
C.B. Bucknall, "Toughened Plastics", Applied Science
Publishers, London 1977. The preferred polymers B are
partially cross-linked and have gel contents above 20% by
weight, preferably above 40% by weight, most preferably
above 60% by weight.
Preferred graft polymers B are obtained by the polymer-
isation of:
25 B.l from 5 to ~() partC by weight, preferably from 30
to 80 parts by weight, of a mixture of
B.l.l from '0 to ~l5 parts by weight of styrene,
~--methyl styrene, styrenes halogenated or methyl
substituted in the nucleus, methyl methacrylate
or mixtures of these compounds and
B.1.2 from 5 to 50 parts by weight of acrylonitrile,
--5--
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.
2~3'~ ~ 8~
met:hacrylonitrile, methyl methacrylate, maleic
acid anhydride, Cl to C4 alkyl-substituted or
phenyl-N-substituted maleimidesor mixtures of
these compounds in the presence of
5 B.2 from 10 to 95 parts by weight, preferably from
20 to 70 parts by weight, of rubber, i.e. polymers
having a glass transition temperature below -10C.
Examples of preferred graft polymers B include polybutadiene
which have been grafted with styrene and/or acrylonitrile
and/or tmeth)acrylic acid alkyl esters, butadiene/styrene
copolymers and acrylate rubbers;. i.e. copolymers of the
type described in DE-OS 1 694 173; polybutadienes grafted
with acry].ic or methacrylic acid alkyl esters, vinyl
acetate, acrylonitrile, styrene and/or alkyl styrenes,
15 butadiene/styrene copolymers or butadiene/acrylonitrile
copolymers, polyisobutenes and polyisoprenes as described
e.g. in DE-OS 2 348 377 (corresponding to US-P 3,919,353).
ABS polymers such as those described in DE-OS 2 035 390 or
in DE-OS 2 248 242(corresponding to US-P 3,644,574 and ~ -
4, O 13, 613 ) are particularly preferred polymers B.
The most:preerred gr.aft polymers B are those which may
be prepared by a grafti.ng reaction of
a~ from 10 to 70% by weight, preEerably from 15 to 50%
by weight, especially from 20 to 40% by weight, based
on graft product B, of at least one acrylic or meth-
acrylic acid ester, or from 10 to 70% by weight,
preferably from 15 to 50% by weight, especially from
20 to 40% by weight, of a mixture of from 10 to 50%
by weight, preferably from 20 to 35% by weight, based
on the mixture, of acrylonitrile or acrylic acid ester
or methacrylic acid ester and ~rom 50 to 90~ by weight,
preferably from 65 to 80% by weight, based on the .
-6-
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mixt`ure, of styrene (graft basis B.l) on
. from 30 to 90% by weight, preferably from 50 to 85%
by weight, in particular from 60 to 80% by weight,
based on graft product B, of a hutadiene polymer
containing at least 50~ by weight, based on ~ , of
butadiene groups (graft basis B.2),
the gel content of the butadiene polymer ~ preferably
amounting to at least 70% by weight (determined in toluene),
the degree of grafting G of the graft polymer preferably
being from 0-15 to 0-55 and the average particle diameter
d50 of the graft polymer B preferably being from 0-05 to
2 ~m, more preferably from 0-1 to 0-6 ~m.
Acrylic acid esters and methacrylic acid esters (~) are
esters of acrylic acid or methacrylic acid and monohydric
alcohols having 1 to 8 carbon atoms.
Methyl, ethyl and propyl methacrylates, n butyl acrylate
and t-butyl (meth)acrylate are preferred.
In addition to its butadiene groups, the butadiene polymer
(~) may contain up to 50% by weight, based on (~), of
residues of other ethylenically unsaturated monomers such
styrene, acrylonitrile, esters of acrylic or methacrylic
acid having 1 to 4 carbon atoms in the alcohol component
(such as methyl acrylate, ethyl acrylate, methyl meth-
acrylate or ethyl methacrylate), vinyl esters and/or vinyl
ethers. Pure polybutadiene is preferred.
Since, as is known, the graft monomers are not completely
grafted on the grat basis in the grafting reaction, the
term "graft: polymers B" usecl in the present invention are
understood to be products obtained by the polymerisation of
graft monomers B.l in the presence of the graft basis B.2.
--7--
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,: ' ~ : ,' . : ,
The degree of qrafting G denotes the ratio by weight of
grafted graft monomers to the graft basis and has no
dimension.
The average particle diameter d50 is the diameter which is
greater than that of 50% by weight of the particles and
smaller than that of the remaining 50~ by weight of
particles. It may be determined by ultracentrifuge
measurement (W. Scholtan, H. Lange, Kolloid, Z. und Z.
Polymere 250 (1972), 782-796).
Another group of very highly preferred polymers B are the
graft polymers obtained
. from 20 to 90% by weight of acrylate rubber having a
glass transition temperature below -20C as graft
basis B.2 and
~. from 10 to 80% by weight of polymerisable, ethylen-
ically unsaturated monomers whose homopolymers or co-
polymers have a glass transition temperature above
25C, used as graft monomers B.l.
The acrylate rubbers (~) in this graft polymer B are
preferably obtained from acrylic acid alkyl esters,
optionally with up to 40% by weight, based O~ ), of
other polymerisable, ethylenically unsaturated monomers.
The preferred polymerisable acrylic acid esters include
Cl to Cg alkyl esters, for example, methyl, ethyl, butyl,
n-octyl and 2-ethyl-hexyl esters; halogenated alkyl esters,
preferably halogeno-Cl-C8-alkyl esters such as chloroethyl
acrylate, and mixtures of these monomers.
For cross-linking, monomers having more than one polymer-
isable double bond may be copolymerised. Examples of cross-
linking monoiners :inc`.u~e esters of unsaturated mono-
-8-
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::
~ ` , ` '
carboxylic acids having 3 to 8 car~on atoms and unsaturated
monohydric alcohols having 3 to 12 carbon atoms or
saturated polyols having 2 to 4 OH groups and 2 to 20 carbon
atoms, e.g. ethylene glycol dimethacrylate or allyl meth-
S acrylate; multiunsaturated heterocyclic compounds such astrivinyl and triallyl cyanurate; polyfunctional vinyl
compounds such as di- and trivinyl benzenes; and triallyl
phosphate and diallyl phthalate.
Allyl methacrylate, ethylene glycol dimethacrylate, diallyl
phthalate and heterocyclic compounds containing at least
3 ethylenically unsaturated groups are preferred cross-
linking monomers.
The cvclic monomers, triallyl cyanurate, triallyl iso-
cyanurate, trivinyl cyanurate, triacryloyl hexahydro-s-
triazine and triallyl benzenes are particularly preferredcross-linking monomers.
The quantity of cross-linking monomers is preferably from
0-02 to 5% by weight, in particular from 0-05 to 2% by
weight, based on graft basis (I).
When cyclic cross-linking monomers having at least 3
ethylenic~lly unsaturated groups are used, the quantity
is advantageously limited to below 1~ by weight of the
graft basis (~).
Preferred ''other~l polymerisable, ethylenically unsaturated
monomers which may be used for the preparation of the
graft basis (I) in addition to the acrylic acid esters
include, for example, acrylonitrilel styrene, a-methyl
styrene, acrylamides, vinyl-Cl-C6-alkyl ethers, methyl
methacrylate and butadiene. Emulsion polymers having a
gel content of at least 60% by weight are preferred
acrylate rubbers used as graft basis (~
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~37~32
Silicone rubbers having graft active points as described in
DE-OS 3 704 657, DE-OS 3 704 655, DE-OS 3 631 540 and DE-OS
3 631 539 are also suit~ble as graft basis as defined under
B.2.
The gel content of the graft basis B. 2 is determined in
dimethyl formamide at 25C (M. Hoffmann, H. Kromer, R. Kuhn,
Polymeranalytik I and II, Georg Thieme-Verlag, Stuttgart
1977).
The hydrogenated nitrile rubbers used as component C are
products obtained by the hydrogenation of randomly
structured copolymers of from 90 to 45% by weight,
preferably from 85 to 50% bv weight, especially from 82
to 52~ by weight, of at lei~st one conjugated diene, from
10 to 55~ by weight, prefera:bly from 15 to 50% by weight,
i5 especially from 18 to 48% by weight, of at least one
unsaturated nitrile and from 0-to 10% by weight, preferably
from 0 to 8% by weight, of at least one other monomer which
is copolymerisable with conjugated dienes and unsaturated
nitriles.
Examples of suitable conjugated dienes include butadiene-
(1,3), 2-methylbutadiene-(1,3), 2,3-dimethylbutadiene-(1,3)
and pentadie.ne-(1.3); acrylonitrile and methacrylonitrile
are suitable unsaturated nitriles.
Aromatic vinyl compounds,(meth)acrylic acid esters having
from 1 to 12 carbon atoms in the alcohol component and
a, ~-unsaturated mono- or di-carboxylic acids may be used
as further monomers.
The following are specific examples: aromatic vinyl
compounds such as styrene, substituted styrenes, e.g. o-,
m- and p-methvl styrene, ethyl styrene, vi.nyl naphthalene
and vinyl pyridine; (m~ h)acry:l.ic acid esters such as methyl
:
--10--
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(meth)acrylate, ethyl (meth)acrylate, n-~utyl (meth)-
acrylate, 2-ethylhexyl (meth)acrylate and 2-hydroxypropyl
(meth)acrylate; among the unsaturated carboxylic acids,
~,~ -unsaturated monocarboxylic acids having 3 to 5 carbon
atoms, such as acrylic acid, methacrylic acid and crotonic
aeid and a,~-unsaturated dicarboxylie aeids having 4 to 5
earbon atoms, sueh as maleie, fumarie, eitraeonie and
itaeonie aeid; further, semiesters of ~,~-unsaturated
diearboxylic acids, such as maleic acid-n-dodeeyl semi-
esters and fumarie aeid-n-butyl semiesters.
Examples of further monomers inelude vinyl ehloride,
vinylidene ehloride, N-methylol aerylamide, vinyl alkyl
ethers having 1 to 4 earbon atoms in the alkyl group and
vinyl esters of earboxylie aei~s having 1 to 18 earbon
atoms, sueh as vinyl aeetate or vinyl stearate.
Speeifie examples of eopolymers to be hydrogenated inelude
aerylonitrile/isoprene eopolymers, aerylonitirle/isoprene/
butadiene terpolymers, aerylonitrile/butadiene/n-butyl
aerylate terpolymers, aerylonitrile/butadiene/2-hydroxy-
propyl methaerylate terpolymers and aerylonitrile/butadiene/methaerylie aeid terpolymers. Aerylonitrile/butadiene
eopolymers are partieularly preferred.
The proaration of hvdrogenated nitrile rubbers with
preservation of the nitrile groups is known, e.g. from
25 ~-OS 3 32S 974.
The degree of hydrogenation (pereentage of hydrogenated
C-C double bonds, based on the total number of C-C double
bonds orgiinally present in the polymer) of the polymer
used as eomponent C is determined by IR or NMR speetroscopy
and amQunts to at least 80%, preferably at least 90%,
espeeially 95%.
LeA 27 ~76
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The hydrogenated polymers used as component C are gel free
and soluble in ketones such as acetone or butanone, in
ethers such as tetrahydrofuran or dioxane and in chlorinated
hydrocarbons such as dichloromethane or chlorobenzene. The
molecular weights of the hydrogenated nitrile rubbers are
from 500 to 800,000 (g/mol) preferably from 10,000 to
600,000 ~g/mol), especially from 30,000 to 400,000 (g/mol)
(Mn, number average, determined by gel permeation chroma-
tography).
The ethylene/vinyl acetate copolymers to be used instead of
hydrogenated nitrile rubbers contain from 10 to 90% by
weight, preferably from 20 to 85~ by weight, of vinyl
acetate, based on the total quantity of copolymers. The
preparation of co?o]ymers is known and is described in,
for example, "Encyclopedia of Polymer Science and
Technology", Volume 15, 577 to 677 (1971), EP 0 078 122,
DE 1 815 337, DE 1 914 756 and DE 3 000 009.
The moulding compounds according to the invention may
contain the usual quantities of additives conventionally
used ~or polycarbonates and graft polymers, such as
stabilizers, pi~ments, mould release agents, flame
retardant; and antistatic agents.
The moulding compounds according to the invention may be
prepared by mixing the components in known manner and melt
compounding or melt extruding them at elevated temperatures,
preferably at 200 to 350C, in the usual apparatus such as
internal kneaders, extruders or double shaft screws.
The cc~mponents may be mixed together in succession or
simuItaneously.
The moulding compounds according to the invention may be
used for the production of mouided articles of all kinds,
-12-
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- -
,
~ ~ 3 ~ 2
e.g. by injection moulding. The following are examples of
moulded articles: housing parts (e.g. for domestic
appliances such as juice presses, coffee machines, mixers),
cover plates for the building industry and motor vehicle
parts. They are also used for electrical apparatus, e.g.
for multipoint connectors, on account of their excellent
electrical properties.
Moulded articles may also be produced by deep drawing
previously produced boards or films.
The invention further relates to the use of the moulding
compounds described for the production of moulded articles.
The thermoplastic moulding compounds according to the
invention are distinguished by their very good notched
impact strength even at low temperatures, improved solvent
resistance (ESC characteristics) and high dimensional sta-
bility under heat.
LeA 27 476
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Examples
Component A 1
Polycarbonate based on bisphenol A/l,l-bis-(4-hydroxy-
phenyl)-3,3,5-trimethylcyclohexane (molar ratio 55:45):
1,436-4 g (6~3 mol) of bisphenol A (2,2-bis-(4-hydroxy-
phenyl)propane, 2,387-0 g (7-7 mol) of 1,1-bis-(4-hydroxy-
phenyl)-3,3,5-trimethylcyclohexane, 7,476-0 g (84 mol)
of 45% NaOH and 33O7 litres of water were dissolved in an
inert gas atmosphere with stirring. A solution of 36-9 g
~0-392 mol) of phenol in 11 litres of methylene chloride
and 13 litres of chlorobenzene were then added. 2,772 g
(28 mol) of phosgene were introduced into the thoroughly
stirred solution at pH 13 to 14 and at 21 to 25C. 14 ml
of ethyl piperidine were then added and the reaction mixture
was stirred for a further 45 minutes. The aqueous phase,
which was free from bisphenolate,was separated off and the
organic phase was washed free from electrolyte with water
after acidification with phosphoric acid and freed from
solvent. The polycarbonate had a relative solution viscosity
of 1-30. The glass temperature of the polymer was found
to be 206C (DSC).
_omponent A 2
P~lycarbonate based on bisphenol A/l,l-bis-(4-hydroxyphenyl)-
3,3,5-trimethylcyclohexane (molar ratio 65:35). Preparation
as under A 1.
Component B 1
Graft polymer of 50 parts by weight of a copolymer of
styrene and acrylonitrile in the ratio of 72:28 on 50 parts
by weight of particulate cross-linked polybutadlene rubber
(average particle diameter d50 = 0O4 ~m) prepared by
-14-
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emulsion polymerisation.
Component B 2
Graft polymer of 50 parts by wei.ght of a copolymer of
styrene and acrylonitrile in the ratio of 90:10 on 50 parts
by weight of particulate, cross-linked polybutadiene rubber
(average particle diameter d50 = 0-4 ~m) prepared by
emulsion polymerisation.
Component C 1
Hydrogenated nitrile rubber on a randomly structured
acrylonitrile/butadiene copolymer having an acrylonitrile
content of 34-1% by weight, a degree of hydrogenation
above 99-2% (determined by infrared spectroscopy) and a
Mooney vi.scosity ML 1 + 4 ~l00C) of 70 (determined
according to DIN 53 523).
Component C ~
Copolymer of ethylene/vinyl acetate in a ratio by weight
of ethylene to vinyl acetate of 30:70.
Preparation and testing of the moulding compounds according
to the invention
_ _
Components A, B and C were melted at temperatures of from
250 to 300^ in a 1-3 litre internal kneader and homogenised.
Rods measuring 80 x 10 x 4 mm (processing temperature 280C)
were produced ~rom the moulding compounds in an injection
moulcling machi.ne ar.d used for testing the notched impact
strengt:h (b~ met:hod ISO 180 lA) at the temperature indicated
in Ta.ble 2.
The ESC characteri.stic was t~ted on rods measuring 80 x 10
-lS-
LeA 27 476
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x 4 mm (mass temperature 280C). A mixture of 50 volumes~
of toluene/50 volumes~O of isooctane and 42-5 voluMes% of
toluene/42~5 volumes% of isooctane/1~ volumes~ of methanol
was used as fuel simulator. The samples were prestretched
by means of a template in the form of a circular arc and
kept in the fuel simulator for 5 minutes at room temperature.
The amount of prestretching ~x was 0-4 to 2~4~. The
tension crack response was assessed over the breakage
in dependence upon the amount af prestretching.
The vicat softening temperature (method A/120) was determined
` according to DIN 53 460 on rods measuring 80 x 10 x 4 mm.
-16-
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As Table 2 shows, the addition of graft polymer/hydrogenated
nitrile rubber or of graft polymer/ethylene-vinyl acetate
copolymer to polycarbonates based on substit~ted cyclo-
alkanes results in a marked improvement in notched impact
strength at room temperature and at lower temperatures. In
addition, the solvent resistance of injection moulded parts
is increased.
-20-
LeA 27 476
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