Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
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PLASTICS COMPOSITION HAVING IMPROVED
WEATHER RES T S'T'ANCE
The invention relates to a plastics
composition containing a polymer and at least one
hindered-amine light stabilizer.
In what follows below, a hindered-amine
light stabilizer will be referred tc as a HALS
compound.
A plastics composition containing a polymer
and at least one HALS compound ,is disclosed in US-A-
3,904,581. Patent Specif,ycation US-A-3,904,581
describes a plastics composition which contains a
polymer and a 4-aminopiperidine compound, which is a
HALS compound, as a resu'_t of which the plastics
composition is stabilized against degradation caused by
heat and light. It is generally known that the
stabilization of a plastics composition against
degradation caused by heat and light, in particular
against degradation caused by UV radiation, improves
the weather resistance of the plastics composition, as
a result of which the plastics composition becomes
suitable for particular applications, for example for
outdoor applications.
Although a plastics composition which
contains a polymer and at least one HA.LS compound
already has a good weather resistance, there is a need
for a plastics composition which has improved weather
resistance.
The object of the invention is to provide a
plastics composition which has such improved weather
resistance.
This object is achieved, according to the
invention, in that the plastics composition according
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to the invention contains a polymer, at least one HALS
compound and at least one bridged amine compound having
at least one N-bridgehead.
Surprisingly, it has in fact been tound
that a plastics composition which contains a polymer,
at least one HALS compound and at least one bridged
amine compound having at least one N-bridgehead has a
weather resistance which is appreciably better than
that cf the known plastics composition which does not
contain the bridged amine compound having at least one
N-bridgehead. It has also been found t:~at a plastics
composition which contains a polymer, at least one F-iALS
compound and at least one bridged amine compound having
at least one N-bridgehead has a weather resistance that
is better than would be expected on the basis of the
sum of the contributions of the HALS compound and the
bridged amine compound. This is all the more surprising
because it has also been found that a plastics
composition which contains a polymer and only one
bridged amine compound is hardly stabilized against
degradation caused by heat and light. Thus, with
certain choices of the components of the plastics
composition according to the invention, it was found
that the weather resistance of the plastics composition
according to the invention could have a weather
resistance which was more than double the weather
resistance of the known plastics compositions.
DE 2637193 describes that compounds having the
general formula
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N=C- F
,w ~ ,
N
tI~
protect organic polymers against the influence of
sight. In Formula I, if n = 1, R is an alkyl or
isoalkyl group having 1-17 C atoms, a phenylalkyl group
having 1-4 C atoms in the alkyl chain, a phenyl or a
naphthyl group, which may be substituted by 2 chlorine
atoms, a hydroxyl group or by at most 3 alkoxy or alkyl
l0 groups having 1-4 C atoms, or represents a heterocyclic
5- or 6-ring with an N or 0 atom, while, if n = 2, R
stands for an alkylene group having 2 to 6 C atoms or a
phenylene group. DE 2637193 describes that the
aforementioned compounds (I) are also effective in the
presence of the usual stabilizers such as antioxidants,
W absorbers, light stabilizers, phosphate stabilizers,
metal compounds, epoxy stabilizers, polyhydric
alcohols, antistatic agents, flame retardants and
pigments. Sterically hindered piperidine compounds are
mentioned as examples of the W absorbers and/or light
stabilizers. It is nowhere apparent from DE 2637193
that compounds having the general formula (I) would
improve the effect of the usual stabilizers, let alone
that there would be a synergistic effect between
compounds having the general formula (I) and HALS
stabilizers. Compounds having the general formula (I)
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are excluded from the plastics composition according to
the invention.
Within the scope of this invention, a xenon
test is employed as a measure of the weather
resistance. The xenon test determines a plastics
composition's resistance to degradation when e:~posed to
light from a filtered (borosilicate glass) xenon lamp
at a black panel temperature of 62°C having an intensity
of 0.35 W~m-'~nm-1, at a wavelength of 340 nm and a
1C relative humidity of 55% by volume in a wet/dry cycle
of 18 minutes wet and 102 minutes dry. The degradation
of the plastics composition is measured as the
difference in the carbonyl absorption at 1713 cm-1 and
the absorption at 1860 cm-1 as a function of the time
for which the plastics composition is subjected to said
combination of light, temperature and humidity. The
weather resistance is expressed as the time for which a
plastics composition is subjected to said combination
of light, temperature and humidity and at which the
difference between the measured carbonyl absorptions is
less than a certain value to be chosen beforehand. In
the xenon test employed here, this value is 0.10 for
the films and 0.50 for plates.
'Hindered-amine light stabilizers' are
understood to be compounds having the following general
formulas:
~I
3a ~- \ ~\Rz
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F~-O-
10
~- N\ - F'~s
~a
and combinations hereof.
R1 up to and including RS are herein
independent substituents; examples of suitable
substituents are hydrogen, ether, ester, amine, amide,
alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl and aryl
groups, which substituents may in turn contain
functional groups; examples of functional groups are
alcohols, ketones, anhydrides, imines, siloxanes,
ethers, carboxyl groups, aldehydes, esters, amides,
imides, amines, nitriles, ethers, urethanes and any
combination thereof. A hindered-amine light stabilizer
may also form part of a polymer.
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Preferably, the HATS compound chosen is a
compound derived from a substituted piperidine
compound, in particular any compound which is derived
from an alkyl-substituted piperidyl, piperidinyl or
piperazinone compound and substituted alkoxypiperidinyl
compounds. Examples of such compounds are:
- 2,2,6,6-tetramethyl-4-piperidone;
- 2,2,6,6-tetramethyl-4-piperidinol;
- bis-(1,2,2,6,6-pentamethylpiperidyl',-(3',5'-di-tert-
l0 butyl-4'-hydroxybenzyl) butylmalonate;
- di-(2,2,6,6-tetramethyl-4-piperid~rl) sebacate
(Tinuvin~ 770 ) ;
- oligomer of N-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-
piperidinol and succinic acid (Tinuvin9 622);
- oligomer of cyanic acid and N,N-di(2,2,6,6-
tetramethyl-4-piperidyl) hexamethylene diamine;
- bis-(2,2,6,6-tetramethyl-4-piperidinyl) succinate;
- bis-(1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl)
sebacate (Tinuvin~ 123);
- bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate
(TinuvinD 765 ) ;
- tetrakis-(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-
butane tetracarboxylate;
- N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl) hexane-
1,6-diamine (Chimassorb~ T5);
- N-butyl-2,2,6,6-tetramethyl-4-piperidinamine;
- 2,2'-[(2,2,6,6-tetramethylpiperidinyl)imino]-bis-
[ethanol] ;
- poly((6-morpholine-S-triazine-2,4-diyl)(2,2,6,6-
tetramethyl-4-piperidinyl)-iminohexamethylene-(2,2,6,6-
tetramethyl-4-piperidinyl)-imino) (Cyasorb~ UV 3346);
- 5-(2,2,6,6-tetramethyl-4-piperidinyl)-2-cyclo-
undecyloxazole) (Hostaviri N2o);
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-
- 1,1'-(1,2-ethanediyl)-bis-(3,3',5,5'-tetramethyl-
piperazinone);
- e-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triaza-
spiro(4,5)decane-2,4-dione;
- polymethylpropyl-3-oxy[4(2,2,6,6-tetramethyl)-
piperidinyl)siloxane (Uvasil~ 299);
- 1,2,3,4-butanetetracarboxylic acid-1,2,3-
tris(1,2,2,6,6-pentamethyl-4-piperidinyl)-4-tridecyl
ester;
l0 - copolymer of a-methylstyrene-T3-(2,2,6,6-tetramethyl-
4-piperidinyl)maleimide and N-stearylmaleirnide;
- 1,2,3,4-butanetetracarboxylic acid, polymer w,.~th
beta, beta, beta',beta'-tetramethyl-2,4,8,10-
tetraoxaspiro[5.5]undecane-3,9-diethanol, 1,2,2,6,6-
pentamethyl-4-piperidinyl ester (Mark LA63)
- 2,4,8,10-tetraoxaspiro[5.5]undecane-3,9-
diethanol,beta,beta,beta',beta'-tetramethyl-, polymer
with 1,2,3,4-butanetetracarboxylic acid, 2,2,6,6-
tetramethyl-4-piperidinyl ester (MarkR LA68)
- D-glucitol, 1,3:2,4-bis-O-(2,2,6,6-tetramethyl-4-
piperidinylidene)- (HALS 7)
- oligomer of 7-oxa-3,20-
diazadispiro[5.1.11.2]heneicosan-21-one,2,2,4,4-
tetramethyl-20-(oxiranylmethyl) (Hostavina N30)
- propanedioic acid, [(4-methoxyphenyl)methylene] -
bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester
( Sanduvor~ PR 31 )
- formamide, N,N'-1,6-hexanediylbis[N-(2,2,6,6-
tetramethyl-4-piperidinyl (Uvinul~ 4050H).
- 1,3,5-triazine-2,4,6-triamine, N,N~~ -[1,2-
ethanediylbis [[[4,6-bis[butyl(1,2,2,6,6-pentamethyl-4-
iperidinyl)amino]-1,3,5-triazine-2-yl]imino]-3,1-
propanediyl]]-bis[N',N' -dibutyl-N~,N' -bis(1,2,2,6,6-
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pentamethyl-4-piperidinyl) (Chimassorby 119)
- 1,5-dioxaspiro (5,5) undecane 3,3-dicarboxylic acid,
bis (2,2,6,6-tetramethyl-4-peridinyl) ester (Cyasorb~~~
UV-500)
- 1,5-dioxaspiro (5,5) undecane 3,3-dicarboxylic acid,
bis (1,2,2,6,6-pentamethyl-4-peridinyl) ester (CyasorbR
UV-516)
- N-2,2,6,6-tetramethyl-4-piperidinyl-N-amino-oxamide;
- 4-acryloyloxy-1,2,2,6,6-pentamethyl-4-piperidine;
- 1,5,8,12-tetrakis[2',4'-bis(1",2",2",6",6"-
pentamethyl-4"-piperidinyl(butyl)amino)-1',3',5'-
triazin-6'-yl]-1,5,8,12-tetrazadodecane.
HALS PB-41 (Clariant Huningue S.A.)
Nylostab~ S-EED (Clariant Huningue S.A.)
3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)-
pyrrolidin-2,5-dione
Uvasorb« HA88
1,1'-(1,2-ethane-di-yl)-bis-(3,3',5,5'-tetra-methyl-
piperazinone) (Good-rite° 3034)
1,1~,1~ -(1,3,5-triazine-2,4,6-triyltris
((cyclohexylimino)-2,1-ethanediyl)tris(3,3,5,5-
tetramethylpiperazinone); (Good-rite' 3150)
1,1~,1~ -(1,3,5-triazine-2,4,6-
triyltris((cyclohexylimino)-2,1-
ethanediyl)tris(3,3,4,5,5-tetramethylpiperazinone)
(Good-rite° 3159)
Preferably use is made of di-(2,2,6,6-
tetramethyl-4-piperidyl) sebacate, (also known under
the tradename of TinuvinR 770), oligomer of N-(2-
hydroxyethyl)-2,2,6,6-tetramethyl-4-piperidinol and
succinic acid (Tinuvin° 622); bis-(1-octyloxy-2,2,6,6-
tetramethyl-4-piperidinyl) sebacate (Tinuvin° 123);
bis-(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate
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- g _
(Tinuvin'"~ 765); N,N'-bis-(2,2,6,6-tetramethyl-4-
piperidyl)-hexane-1,6-diamine (Chimassorb'"-~ TS);
poly((6-morpholine-S-triazine-2,4-diyl)(2,2,6,6-
tetramethyl-4-piperidinyl)-iminohexamethylene-(2,2,6,6-
tetramethyl-4-piperidinyl)-imino) (Cyasorb°' UV 3346);
5-(2,2,6,6-tetramethyl-4-piperidinyl)-2-cyclo-undecyi-
oxazoi) (HostavinG N20);
polymethylpropyl-3-oxy-[4(2,2,6,6-tetramethyl)-
piperidinyl)-siloxane (Uvasil~' 299),
l0 - 1,2,3,4-butanetetracarboxylic acid, polymer ~~ri~h
beta,beta,beta',beta'-tetrameth~.~l-2,4,8,10-
tetraoxaspiro(5.5]undecane-3,9-diethanol, 1,2,2,6,6-
pentamethyl-4-piperidinyl ester (Marl:"' LA63)
- 2,4,8,10-tetraoxaspiro(5.5]undecane-3,9-
diethanol,beta,beta,beta',beta'-tetramethyl-, polymer
with 1,2,3,4-butanetetracarboxylic acid, 2,2,6,6-
tetramethyl-4-piperidinyl ester (Marks LA68)
- D-glucitol, 1,3:2,4-bis-O-(2,2,6,6-tetramethi~l-4-
piperidinylidene) (HALS 7)
- oligomer of 7-oxa-3,20-
diazadispiro(5.1.11.2]heneicosan-21-one,2,2,4,4-
tetramethyl-20-(oxiranylmethyl) (Hostavin~' N30)
- propanedioic acid, [(4-methoxyphenyl)methylene]-
bis(1,2,2,6,6-pentamethyl-4-piperidinyl) ester
(Sanduvor° PR 31)
- formamide, N,N'-1,6-hexanediylbis(N-(2,2,6,6-
tetramethyl-4-piperidinyl (Uvinul° 4o50H).
- 1,3,5-triazine-2,4,6-triamine, N,N~~ -[1,2-
ethanediylbis (((4,6-bis(butyl(1,2,2,6,6-
pentamethyl-4-iperidinyl)amino]-1,3,5-triazine-2-
yl] imino] -3 , 1-propanediyl] ] -bis [N' ,N" -dibutyl-N~ , N' -
bis(1,2,2,6,6-pentamethyl-4-piperidinyl) (Chimassorb°
119 )
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- 1,5-dioxaspiro (5,5) undecane 3,3-dicarboxylic acid,
bis (2,2,6,6-tetramethyl-4-peridinyl) ester (Cyasorb°
UV-500)
- 1,5-dioxaspiro (5,5) undecane 3,3-dicarboxylic acid,
bis (1,2,2,6,6-pentamethyl-4-peridinyl) ester (Cyasorb~"'
UV516)
- mixtures of esters of 2,2,6,6-tetramethyl-4-
piperidinol and fatty acids (Cyasorbv UV 3853);
HALS PB-41 (Clariant Huningue S.A.)
Nylostab'J S-EED (Clariant Huningue S.A.)
3-dodecyl-1-(2,2,6,6-tetramethyl-4-piperidyl)-
pyrrolidine-2,5-dione
Uvasorb~~ HA88
1,1'-(1,2-ethane-di-yl)-bis-(3,3',5,5'-tetra-methyl-
piperazinone) (Good-rites' 3034)
1,1~,1~ -(1,3,5-triazine-2,4,6-triyltris
((cyclohexylimino)-2,1-ethanediyl)tris(3,3,5,5-
tetramethylpiperazinone); (Good-rite' 3150)
1,1~,1~ -(1,3,5-triazine-2,4,6-
triyltris((cyclohexylimino)-2,1-
ethanediyl)tris(3,3,4,5,5-tetramethylpiperazinone)
(Good-rites 3159).
The bridged amine compound having at least
one N-bridgehead that can be used within the scope of
this invention is preferably a compound derived from a
compound having the general formula 1 or 2 (see formula
sheet), where M1 to M4 are bridgeheads and each
bridgehead is chosen independently of one another from
carbon, nitrogen, silicon or phosphorus, with the
3o proviso that at least one bridgehead should always be a
nitrogen atom and carbon and silicon may be
substituted; an N-bridgehead is defined as a bridgehead
which is a nitrogen atom; D1, Dm, Dn, Do, Dp and Dq here
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each stand for a chain having a length of 1 to 20
atoms, the number of atoms of which the chains are made
up being equal to 1, m, n, o, p and q, each number of
atoms and type of atom to be chosen independently of
one another, and the chains being capable of having
different lengths and being capable of being made up of
different types of atoms. The c:-wins may also contain
side groups, the number cf atoms in tre side groups not
being included in the number of atoms of the chain.
Suitable choices for the atoms cf which the chairs are
made up are carbon, nitrogen, cxygen, silicon and
phosphorus. Preferably the chains are made up of 1 to 3
carbon atoms.
Preferably the bridged amine compound
having at least one N-bridgehead is used with a HALS
compound in a ratio, relative to the amount of ziALS
compound, of between approximately 1:20 (m:m) and
approximately 20:1 (m:m), more preferably in a ratio of
between approximately 1:10 (m: m) and approximately 1C:1
(m: m), most preferably in a ratio of between
approximately 1:5 (m: m) and approximately 5:1 (m: m).
Within the limits of the latter ratios the weather
resistance is better than is expected on the basis of
the amounts of the bridged amine compound having at
least one N-bridgehead and the HALS compound present.
The amount of bridged amine compound having
at least one N-bridgehead that can be used in the
plastics composition may vary within a wide range,
which can be easily determined by an average person
skilled in the art. The range may vary depending on for
example the type of polymer, the type of FiALS compound,
the other additives in the additives package, the
weather resistance to be realized or in general the
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type of plastics composition, its properties and its
specific application.
It is for example possible for the bridged
amine compound having at least one N-bridgehead to be
S present in the plastics composition in an amount,
relative to the amount of polymer in the plastics
composition, of, preferably, between approximately
0.01% by weight and approximately 10.0% by weight, more
preferably in an amount of between 0.05% by weight and
l0 5% by weight, most preferably in an amount of between
0.1% by weight and 2.5% by weight.
Preferably the bridged amine compound
having at least one N-bridgehead is chosen so that a
plastics composition is obtained having a weather
15 resistance measured with the aid of the xenon test
which is higher than approximately 500 hours, more
preferably higher than approximately 750 hours, and
most preferably higher than approximately 1000 hours.
Suitable choices for the bridged amine
20 compound having at least one N-bridgehead are:
- derivatives of 7-nitro-1,3,5-triazadamantane and 7-
amino-1,3,5-triazadamantane,
- derivatives of 7-amino-1,3,5-triazadamantane having
the general structure II or III:
R
N~ ~N
N
(II)
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~R
N- G
S 'R
I
,N'~ ~.N
i
~/ N',
(III)
where R and R' are independent substituents; examples
of suitable substituents are hydrogen, ether, ester,
amine, amide, alkyl, alkenyl) alkynyl, aralkyl,
cycloalkyl and aryl groups, which substituents may in
turn contain functional groups; examples of functional
groups are alcohols, ketones, anhydrides, imines,
siloxanes, ethers, carboxyl groups, aldehydes, esters,
amides, imides, amines, nitriles) ethers, urethanes and
any combination thereof.
The substituent may moreover connect
several of the I and/or II compounds to one another.
- derivatives obtained in a reaction of 7-amino-1,3,5-
triazadamantane with compounds containing one or more
functional groups. Examples of these functional groups
are: aldehydes, acids, esters, amides, ketones,
anhydrides and isocyanates.
- triazadamantane derivatives that are bound to a
polymer (preferably a polyolefin) with the aid of an
imide functionality;
- polymer-bound compounds obtained by the reaction of
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7-amino-1,3,5-triazadamantane with a polymer
(preferably a polyolefin) functionalized with malefic
anhydride;
- hexamethylenetetramine (HMTA),
diazabicyclo[2.2.2]octane (DABC01 or derivatives
thereof. HMTA and DABCO are easy to obtain comme~:cially
or are easy to prepare using generally known processes.
HMTA, for example, can easily be prepared from the
cheap and easily obtainable basic raw materials ammonia
and formaldehyde.
The bridged amine compound having at least
one N-bridgehead is preferably used as a salt, more
preferably as an ammonium salt. Preferably a carboxylic
acid is chosen as the salt-forming agent. Examples of
suitable carboxylic acids are aliphatic carboxylic
acids, aliphatic dicarboxylic acids and aromatic
carboxylic acids. Suitable choices are stearic acid,
sebacic acid, cyclohexanedicarboxylic acid and
benzenetricarboxylic acid. Preferably the bridged amine
compound having at least one N-bridgehead is not used
as a salt if the salt-forming agent contains a halogen
or sulphur, for it is generally known that halogen-
containing or sulphur-containing compounds can reduce
the effect of the HALS stabilizer.
The bridged amine compound having at least
one N-bridgehead is preferably substituted with at
least one substituent having a molecular weight of
preferably at least 50, more preferably at least 100.
Surprisingly, it has been found that, as a
result of using the bridged amine compound having at
least one N-bridgehead either in its salt form, or
substituted with at least one substituent having a
molecular weight greater than approximately 50, or in
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its salt form and substituted with at least one
substituent having a molecular weight greater than
approximately 50, a plastics composition is obtained
which has still better weather resistance.
The plastics composition according to the
invention preferably contains a thermoplastic polymer
chosen from the group of polyolefins and styrene
polymers. Suitable choices are, for example: -
propylene polymers) such as propylene homopolymer)
ethylene-propylene random copolymer, ethylene-propylene
block copolymer and mixtures hereof. Also defined as
propylene polymers within the scope of this invention
are mixtures containing at least 50% by weight of one
of the aforementioned propylene polymers with, for
example, polyethylene or ethylene-propylene-dime
copolymers;
- ethylene polymers, such as low-density polyethylene
(LDPE), high-density polyethylene (HDPE), very-low-
density polyethylene (VLDPE), linear-low-density
polyethylene (LLDPE) or ultra-high-molecular-weight
polyethylene (UHMWPE);
- butylene polymers, such as poly(1-butylene).
Suitable choices of styrene polymers are, for example,
polystyrene, high-impact-resistant polystyrene (HIPS),
styrene-acrylonitrile copolymer (SAN), acrylonitrile-
butadiene-styrene copolymer (ABS), styrene-malefic
anhydride copolymer (SMA) and styrene-maleimide
copolymer (SMI).
More preferably, the polymer is a propylene polymer or
an AHS, still more preferably a propylene polymer.
The bridged amine compound having at least
one N-bridgehead can be introduced into the plastics
composition with the aid of one of the many standard
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methods known to a person skilled in the art at any
desired time before making a plastic article, for
example a moulded part, sheet, film, fibre, coating,
foam, tape, latex or powder, from the plastics
composition.
According to a first method, the bridged
amine compound having at least one N-bridgehead is
mixed, for example in the form of a powder, solution,
emulsion or suspension, with the other components of
the plastics composition which are in the form of, for
example, a powder or a melt.
According to a second method, the bridged
amine compound having at least one N-bridgehead is
first mixed with at least one HALS compound and
optionally with other additives in a so-called
additives package, for example in the form of a powder,
solution, emulsion or suspension, and said package is
then added to the plastic, for example in the form of a
powder or as a melt.
The plastics composition containing a
polymer, at least one HALS compound and at least one
bridged amine compound having at least one N-bridgehead
may also contain other additives, for example
antioxidants, thermal and UV stabilizers, metal
deactivators, fillers, pigments, flame retardants,
optical whiteners and similar additives which are used
in plastics compositions.
The invention will be explained further by
reference to the examples without being limited hereto.
Exa~les
In the examples, the following general
processes were followed.
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Dreparar;on of the various bridq-ed amines
DABCO stearate:
A solution of 28.45 grams (0.1 mol) of
stearic acid in ethanol was added, drop by drop, at
room temperature, with stirring, to a solution o~ 11.2
grams (0.1 mol) of DAHCO in ethancl. The mixture was
evaporated with the aid of a Rotavap.
HMTA stearate:
A solution of 28.45 grams (0.1 mol) of
stearic acid in ethanol was added, drop by drep, with
stirring, to a solution of 14 grams (0.1 mol) c~ DABCO
in ethanol. The mixture was evaporated with the aid of
a Rotavap.
DABCO sebacate:
A solution of 20.2 grams (0.1 mol) of
sebacic acid in methanol was added, drop by drop, at
room temperature, with stirring, to a solution of 22.4
grams (0.2 mol) of DABCO in methanol. The mixture was
evaporated with the aid of a Rotavap.
DABCO benzene tricarboxylate:
A solution of 21 grams (0.1 mol) of benzene
tricarboxylic acid in absolute ethanol was added, drop
by drop, at room temperature, with stirring, to a
solution of 33.6 grams (0.3 mol) of DABCO in absolute
ethanol. The salt was precipitated from the solution.
The mixture was evaporated with the aid of a Rotavap
and dried in a vacuum drying stove.
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DABCO distearate:
A solution of 56.9 grams (0.2 mol) of
stearic acid in ethanol was added, drop by drop, at
room temperature, with stirring, to a solution of 11.2
grams (0.1 mol) of DABCO in ethanol. The mixture was
evaporated with the aid of a Rotavap and dried in a
vacuum drying stove.
7-Nitro-1,3,5-triazadamantane:
A mixture of 56.8 ml (1.0 mol) of
nitromethane and 45 ml (1.2 mol) of formic acid was
added, drop by drop, to a solution of 140.2 grams (1.0
mol) of hexamethylenetetramine in 500 ml of ethanol
(80%), with constant stirring and refluxing. The
mixture was refluxed for 4 hours and set aside for one
night. The separated crystalline product was washed a
few times with water and ethanol. After
recrystallization in water, the product (white needles)
was dried in the vacuum drying stove. (Literature:
Czechoslov. Chem. Commun Collection [vol. 40J, 1975,
pp. 2179-82).
7-Amino-1,3,5-triazadamantane:
15.0 grams of 7-nitro-1,3,5-
triazadamantane, 100 ml of methanol and 1.5 grams of
wet Raney cobalt as a catalyst were introduced into a
Parr autoclave (volume 160 ml) fitted with a stirrer
and baffles. The hydrogenation was carried out for an
hour at maximum speed, beneath hydrogen at 80 bar
pressure and 80°C. After removal of the catalyst through
filtration, the methanol was removed by means of the
rotavapor. The crystalline product was dried in a
vacuum drying stove.
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7-Dodecylideneamino-1,3,5-triazadamantane:
8.4 grams of 7-amino-1,3,5-triazadamantane,
10.0 grams of dodecanal, 85 ml of methanol, 10 ml of
toluene and 2.0 grams of wet Raney cobalt as a catalyst
were introduced into a Parr autoclave (volume 160 ml)
fitted with a stirrer and baffles. The reaction was
carried out for an hour in a nitrogen atmosphere (2
bar) at maximum speed and 80°C. After removal of the
catalyst through filtration, the filtrate was
evaporated witr. the aid of a Rotavapc~ and dried in a
vacuum drying stove.
PP-MA-7-amino-1,3,5-triazadamantane:
0.8 grams of 7-amino-1,3,5-triazadamantane in 75 ml of
solvent was added, drop by drop, with constant
stirring, at 160-165°C, to a solution of 10.0 grams of
PP-MA (Hostaprime~HCS) (PP grafted with approximately
2.8% malefic anhydride) in 150 ml of inert solvent.
After cooling to approx. 90°C, the product was
precipitated using 100 ml of acetone. The separated
product was dried in a vacuum drying stove, after which
it was compressed to form a plate at 210°C. The latter
was cryogenically ground to a powder.
p~paration of a plastics composition
A polymer powder (PP or ABS) was mixed with
a solution containing an amount of a HALS compound.
This mixture was dried in an oven (Hereaus Vacutherm)
for 24 hours at a temperature of 28°C and a pressure of
approximately 20 mm Hg. Then a solution of the bridged
amine compound having at least one N-bridgehead was
CA 02280158 1999-08-10
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- 20 -
added to the plastics composition. This plastics
composition was also dried in the same way as described
above. Plastics compositions (blanks) in which the
amount of HALS compound and/or bridged amine compound
S having at least one N-bridgehead in the solution was
zero were also prepared using this process.
production of PP f~lms and g~a s
The PP composition was compressed to form a
film using a Fontijne press (type TP200, 5 minutes
pressureless preheating at 190°C, followed by the
application of a pressure of 100 - 120 kNewton,
followed by 10 minutes cooling at said pressure). The
thickness was checked using a Heidenhain electronic
meter. On average, thicknesses of 120 - 150 ~Zm were
obtained for the films and 1 mm for the plates.
Production of ABS films and plates
The ABS composition was compressed to form
a film using a Fontijne press (type TP200, 5 minutes
preheating at a pressure of 50 kNewton and 210°C,
followed by the application of a pressure of 100-120
kNewton, followed by l0 minutes cooling at said
pressure). The thickness was checked using a Heidenhain
electronic meter. On average, thicknesses of 120 - 150
~m were obtained for the films and 1 mm for the plates.
Production of PE films
The PE compositions were produced by means
of compounding at 160°C. Next, films with a thickness of
150 ~m were blown at the same temperature.
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DerPrmination of the weather resistance
The weather resistance of a plastics
composition was determined in a weather-resistance test
performed in an Atlas Material Testing Technology
Weather-O meter (type Ci65) according to the method
described in the preceding description. The degradation
was measured with the aid of F'='-IR. The weather
resistance is then expressed as the amount of time (the
number of hours) for which a plastics composition is
l0 subjected to said combinatio~: of light, tempera:.ure and
humidity and at which the difference between the
measured carbonyl absorptions is less than 0.10 before
and after ageing in the case of the films and less than
0.5 in the case of the plates.
In some cases the change in colour as a
result of ageing was characterized with the aid of a
calorimeter according to ASTM standard 1925.
In the examples, the following
abbreviations and tradenames were used:
PE: polyethylene
PP: polypropylene
ABS: acrylonitrile-butadiene-styrene copolymer
Tinuvin 770: di-(2,2,6,6-tetramethyl-4-piperidyl)
sebacate
Tinuvin~622: oligomer of N-(2-hydroxyethyl)-2,2,6,6-
tetramethyl-4-piperidinol and succinic acid
Tinuviri 123: bis-(1-octyloxy-2,2,6,6-tetramethyl-4-
piperidinyl) sebacate
Chimassorb~ 944: oligomer of cyanic acid and N,N
di(2,2,6,6-tetramethyl-4-piperidyl)-hexamethylene
diamine
Chimassorb~ 119: 1,3,5-triazine-2,4,6-triamine, N,N~~ -
[1,2-ethane-diylbis[[[4,6-bis[butyl(1,2,2,6,6-
CA 02280158 1999-08-10
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- 22 -
pentamethyl-4-iperidinyl)amino]-1,3,5-triazine-2-
yl] imino) -3 , 1-propanediyl] ] -bis (N~ , 2d~ -dibutyl-N~ , N~ -
bis(1,2,2,6,6-pentamethyl-4-piperidinyl)
Hostavin9 N30: oligomer of 7-oxa-3,20-diazadispiro
15.1.11.2]-heneicosan-21-one,2,2,4,4-tetramethyl-20-
(oxiranylmethyl)
DABCO: diazabicyclol2.2.2]octane
HMTA: hexamethylenetetramine
DABCO stearate: monosalt of stearic acid and DABCO
DABCO distearate: salt of DABCO containing two stearic
acid molecules
DABCO sebacate: salt of sebacic acid (diacid)
containing two DABCO molecules
DABCO benzenetricarboxylate: salt of
benzenetricarboxylic acid containing three DABCO
molecules
HMTA stearate: monosalt of stearic acid and DABCO
Atade: 7-amino-1,3,5-triazadamantane
Dodecylidene-atade: 7-dodecylideneamino-1,3,5-
triazadamantane.
PP-MA-atade: MA-grafted polypropylene modified with
atade, synthesized according to the above
specification.
Examples I-II and Comparative Experiments A-D: Weather
resistance of various plastics compositions
A series of plastics compositions was
prepared using the process described above. In this
process, the composition of the plastics composition
was varied. Di-(2,2,6,6-tetramethyl-4-piperidyl)
sebacate (tradename: Tinuvin 770, Ciba-Geigy, Basel)
was chosen as the HALS compound.
CA 02280158 1999-08-10
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PP (Stamylanm, type P83m18, DSM, the Netherlands) was
chosen as the polymer. Films were produced from the
plastics compositions using the process described
above. The films were subjected to a weather-resistance
test and the weather resistance was determined as
described above. The results are summarized in Table 1.
CA 02280158 1999-08-10
WO 98/36023 PCT/NL98/00088
-24-
a~
U
1J
.,-i cn u1 u1 tn o 0
V1 ~-I I~ t~ t~ tI1 o I~
w r~, o
~ o
v
rt
a~
3
p I v N
p b t~ ~ rd
?-~rd
p ~ b ~ ~ ~r
v b ~ it
p a~ ~ y v
~ cn ~ ~n
O N
O ~ O x
U t~
a~ a x a
b 3 3 3 3
O' b ~
N ~
p aw aw ow ow
m o m o
0 0 0 0
w
O
2s .- 3 3 3
U ~ O ~ i i i ~7
ow ow ow
p ~ rl rl r-1
U o o O
N
H H H H H H
W W L1 ~ G1~ G3~
v r~ C4 ~ W C4 W W
O
3 p,
v
ri '~' ~(,'(.T~U A H H
,La W H
H
CA 02280158 1999-08-10
- WO 98136023 PCT/NL98/00088
- 25 -
Examt~les III VII and Comparative Experiments E and F:
Weather resistance of Mastics comn~~itions having
various concentrations of HALS compound and bridged
amine compound
Example I was repeated, the concentrations
of the HALS stabilizer chosen and the bridged amine
compound having at least one N-bridgehead being varied.
The results are summarized in Table 2. From this it can
be concluded that a plastics composition containing
amounts of 0.1% by weight to 0.5% by weight of a
bridged amine compound exhibits improved weather
resistance, which increases as more bridged amine
compound is used. It was thus possible to more than
double the weather resistance (Example F versus ViI).
CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
-26-
H
t-~ CrJ C C5'
c c H H x
H H 'T1 C
H Q N
..
ro a
ro ro ro ro ro ro ro
Q G r~
ro ro ro ro ro ro ro
H H H H H H H (D
(D
H H H H H H H ~"~ ~fj
a.
ri
O O O O O O O
n n
N N N F~ I-' N H' W O 1-~-
I d o\ d ~ d a\ d N.
d O 'C7
'C 'G "G "G "G ~ ~ ~ ~ lD
'G tL
rt G
- a a.
rr c~ rr rr rT rr 7
rr n
~~
O
I G
j
O O O ~ ~ ~ ~ O f1~
N V-' ~ N 1-~ ~ 1-'-
d U1 d O O
tr' d tr'
t~' tT G ~D G n
"G 'G tr'~C '~G ~ Q.
~G ~n
n
n C ~c3
O O O O N-
O O
-- ~
~n cn ~n m N-
U~ O
c-t (-t c-r rr w
fD (D rr fD (D G rr
tv W (D tv N p O
rt f-S W n ft , G
iv H ~ s~ I--'
rr ~t W rr c"r m
(D fD n fD (D (D
fD W G'
~ C
~.
O G
G
fD
z w
n
m n o
f.,_
G
rr . cn
w
~n
n
n x o
c~
o n ~ n
0o N o o J .~ a, G (D a fD
N W N W 00 ~7 O ~'t UI
0 0 0 0 0 0 0 0111-' H
N
rr W
W rr
n o
m
0
rn
CA 02280158 1999-08-10
WO 98/36023 PCT/NL98/00088
- 27 -
Examples IX-XII : Trleather rebsistance of Mastics
compositions containing various bridged amine compounds
having at least one N-bridgehead
Example I was repeated using a plastics
composition containing 0.2% of a HATS (Tinuvir.~ 770),
the type of bridged amine compound having at least one
N-bridgehead being varied. The results are summarized
in Table 3.
CA 02280158 1999-08-10
WO 98/36023 PCT/NL98/00088
-28-
H
x
x H
H H x x ~ rn
n
0
~ ro
ro ro ro 0 o c~
ro G
ro ro ro ro
H H H H fD
H H H H
H H H H
n
0 0 0 0 C
_ n r- m
N N N N W O
do prodo pro
O 'L7 ~-' fD
E G
V . (D
rt rr rr rt o
w
i U7 M
ro
0
w
ca m
m o
t7 t~ co z n
d d ~ o ~
m n n o n
~ '~ r-r, O
O r, C7 O O w ~ Q.
fn cn rr O n ~ 'b
N- O cT lD N- G 1-~-G' O
a, n m tr' o ~ A.
n~ ~ ~ ~ a. Cl. tY
1~- nt ~i n (D
m a' w w i p., O
rt p fT t'r ~
m x cn m
w o
n
rt rt ~ ~ O
c~
w
f.,.
W
C
w w
rr n
m O
v G' ~-i G
O
N G ni
N J U1 ~D ~"~fD
N N O N U1 U1
O O O O '-'h'-
O
W
,7 O
(y M
fD
n
!~-
.
l~
(D
CA 02280158 1999-08-10
WO 98/36023 PCTlNL98/00088
- 29 -
Example XIII and Comparative Experiment G: Weather
~PSistance of PE films
Example I was repeated using two plastics
compositions, both composed of PE (LDPE, type 2304
AN00, DSM, the Netherlands) and 0.05% by weight of HALS
compound (Tinuvin~ 770), with 0 and 0.06% by weight,
respectively, of DABCO added thereto. The plastics
compositions were processed tc form blown films 150 Ecm
thick. The films were exposed to light in a Suntester.
The weather-resistance treatment was performed in a
borosilicate glass vessel according to a method
described in Po~ytn Deq_ & Stab., 39, 225-233 (i993).
The weather resistance was determined as described
above; however, in this case, a change in the carbonyl
absorption of 0.05 units was employed as deterr,:ir.ing
the weather resistance. The weather resistance of the
film without DABCO (Comparative Experiment G) was 2700
hours and the degradation increased considerably from
2400 hours onwards; the weather resistance of the film
containing DP.BCO was more than 3500 hours and the
degradation showed a constant profile at 0.03 units.
Example XIV and Comparative Experiments H and I:
WPatheY resistance of ABS films
Example I was repeated using three plastics
compositions composed of ABS (Ronfaliri , type 356**,
DSM, the Netherlands), ABS and 0.5% by weight of HALS
compound (Tinuvin~ 770) and ABS, 0.5% by weight of HALS
compound and 0.5% by weight of DABCO stearate,
respectively. The degradation was measured as a colour
change using a colorimeter and the weather resistance
was determined according to ASTM standard 1925 as the
amount of time (the number of hours) for which a
CA 02280158 1999-08-10
- WO 98136023 PCT/NL98/00088
- 30 -
plastics composition is subjected to said weather-
resistance test and at which the measured colour change
is less than 5 units. The results are summarized in
Table 4.
CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
-31-
I
x x
H H x
c
ro
0
c~
H H H f'S ~-
j
~i
O O
n
tn tn N O fT
d d O ~
c o r
G ~
..-
0
I
o ~~ ~ ~ rd
0
d ~ w
~ o
cr
.C i ~ rr n
m
w
0
b
0
m
r-
rr
O
G
m
O N
G ~"T
n ?
U1 fD
n
fi
N fD
H J J N
wn o N-
N
rr
G
n
m
CA 02280158 1999-08-10
WO 98/36023 PCTML98/00088
- 32 -
Examples XV XVII and Comrarat-ive Experiment. J:
Weather resistance of ABS films
A series of plastics compositions was
prepared using the process described above. In this
process the composition of the plastics composition was
varied. Di-(2,2,6,6-tetramethyl-4-piperidyl) sebacate
(tradename: TinuvinD 770, Ciba-Geigy, Basel) was chosen
as the HALS compound. ABS (Ronfalin~, type 356**, DSM,
the Netherlands) was chosen as the polymer. Elates were
to produced from the plastics compositions using the
process described above. The degradation was measured
as a change in colour using a colorimeter and the
weather resistance was determined according to ASTM
standard 1925 as the amount of time (the number of
hours) for which a plastics composition is subjected to
said weather-resistance test and at which the measured
change in colour is less than 5 units. The results are
summarized in Table S.
CA 02280158 1999-08-10
WO 98/36023 PC'T/NL98/00088
-33-
H
w
rr
H C C ~-i >C (D
H H V1
fD
w
O
t!~ (l Wl1(O E"' lD
H H H H
H H H H
N
N.
fT
w
O O O H G
cn v, u, o
d d d d ~ ~ 'x
O n7 ~ O
CJ' CJ' t~ L3' C O C r"h
"G 'G 'G ': C C U~
rr G
-' C1
(-r rt r t'r
b
I
_
O 3 H c-r
f"f
m ~y ~ ~ ~ m
f'T w U1 ~ ~ M O
~ rr
w ~ m w ~ ~ O
cn n. ly ~ b N.
fD w ~~ ~ a. rr
Ct C. C lLl
(D fD ~ ~ ~ y
i
N
_ (D
V V V ~
H H O ~, w
O O O ll1 C ~ f"r
O O O ~ r't
O O O O U1
n '~
CA 02280158 1999-08-10
WO 98/36023 PCT/NL98/00088
- 34 -
Examples XVIII - XXIII and Comparative E~cperiments K -
Weather resistance of ~lasti~-s comz~ositions
~ontaininq various bridged amine compounds having at
least one r1-bridgehead
Examples III - VIII were repeated, the type
o~ bridged amine compound having at least one N-
bridgehead being varied. The results are summarized in
Table 6.
CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
-35-
x
x H ~ ~r o z .~ r x x
DC H
H
b ro
ro b ro ~o ro ro ro w b o E
ro ro ro ro ro ro ro ro ro 0
a
C C C C C C C C C n
n
w
n
'
C
(
J
H..
0 0 0 ~ ~ o o b m
0 I o r ~
E.-~N N 0 0 ~ m
d d d ~ N d ~ (~ rr
o\ o\ d N d
tr' ~ ~ '~ d ,~ ,~ ~ ro f'f
~ "',.J
E r~r r~r ~ E rT C
n
rr rr rr rr rr ~ m
i rr ~ m
' a ~
O
Cn
rn
rr
w
I
tr'
3 ~ rr 3 p rr J ~ n m cn
\: ~- ~ ~ O ~"t
N- ~ ~ hj p ~ ~
m ~ ~' cn n ~ w rr B
0 0 ~ ~ ~ ~'
r-r ~ ~ ~ 0 0 _ ~u _ o
a o w ~ ~ ~ ~ ~ O ~
fD ~ (D ~ F-~ (D fD (D ~ G ~ r~
r~-~a' ri r~-~~ W Q, ~ N
w v w w
~ 1-, ~ rt , n a. Q'
~T ~ ~,.~ rT ~ ~ o w rr
fD fD (D N ~. .
~ ~
tn
~ i
n
O
fr
d cD p)
N.
'.~
fr.
~ W
C
'D N F-~ ~t J f'' W 01 J (,~,. N
fD
o op ~''~o m m J o O N W G
0 tn ui o G ~ rr
r-S p~ m
~'
N (~7
~
fD rr
(D
N
O
M
r3'
~i
N.
Q.
W
fD
CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
-36-
x
x x
H x x x
H H H '
H H
ro
ro ro ro ro o
ro b ro ro
H H H H
C C C C
O O O
O
o\ N N N W
e\ o\ \
O n
b
rr '~ G
rr rr ~T
n H
0
n cn
3 3 ~ N- ~ O
w
n ~ n
O ~ ~
CT
cn ~n a. ~ rt 3
N o b
N.
rr rr iv N.
(D (D ~ ~ N O G C1
~
w n~ w - ~ ~
~, r
u
w w n ~ ~"' ~'
n p.
o
N f-'-
d~ (D
N N 1-~p 1-''
J W W W
T
W O O~ W ~- ~
OD ~P 01 j
n
(D
CA 02280158 1999-08-10
WO 98/36023 PCT/NL98/00088
- 37 -
E~camples XXIV - XXIX~ Weath r resistance of Mastics
compositions containina various bridaed amine compounds
havina at least one t1-bridgehead
Examples III - VIII were repeated, the
concentration of 7-amino-1,3,5-triazadamantane being
varied. The results are summarized in Table 7.
CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
-38-
H
x
x x r tr
x c x ~ x
~ x '~
x H H H C C n
H .'~
~1
~,
..
b i fD
ro ro ro ro b ro W
rr
ro ro ro ro b ro
C C C C C C ~p O
n
m
w
M
~
o 0 0 0 0 0
N N N N I~ N w n
d d d o\ o\ d O n Er
CT CT' b' CT CT'CT G ~ N
.C ~ "C 'G 'G "G rGr 'C G.
~ ~ I
~ ~ rb
rr r' ~ rt rT G
rr I) G m
G
I r
r
~
rn
~
r' ~1 O
0 0 ~ 0 0 0 ~ ~~ ~ b
0 O
Ut N Ui N N W ~ N UI
do d N o\ d I ~ Er.
do d O t~. O rr
N
N
'-' ~ w U1
c~r rr rr ~r
rr c-r yn
C
W
C
w
n
O
_ ~ ~ G
m ~ cn
'a ~,",~ .a m ~ N.
O ~ ~ n
a o o tn a~ J G
o o ~ ~ ~ O
- G H n
n (D
iD G
rr
fi
N.
O
m
O
rn
CA 02280158 1999-08-10
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- 39 -
Examples XXX LXXXV and Comparative E~tneriments R -
A7 Weather resistance of various plastics
~~mpositions.
A series of plastics compositions was
prepared using the process described above. In this
process the composition of the plastics composition was
varied. Di-(2,2,6,6-tetramethyl-4-piperidyl) sebacate
(Tinuvin"' 770), oligomer of N-(2-hydroxyethyl)-2,2,6,6-
tetramethyl-4-piperidinol and succinic acid (Tinuvir.~'
l0 622), bis-(1-octyloxy-2,2,6,6-tetramethyl-4-
piperidinyl) sebacate (Tinuvin''-' ~.23) , oligomer of
cyanic acid and N,N-di(2,2,6,6-tetramethyl-4-piperidyl)
hexamethylene diamine (ChimassorbU 944), 1,3,5-
triazine-2,4,6-triamine, N,N~~ -[1,2-ethane-
diylbis[[[4,6-bis[butyl(1,2,2,6,6-pentamethyl-4-
iperidinl~1) amino] -1, 3, 5-triazine-2-yll iminol -3, 1-
propanediyll]-bis[N~,N~ -dibutyl-N~,N~ -bis(1,2,2,6,6-
pentamethyl-4-piperidinyl) (Chimassorb~ 119) and
oligomer of 7-oxa-3,20-diazadispiro [5.1.11.21-
heneicosan-21-one,2,2,4,4-tetramethyl-20-
(oxiranylmethyl)- (Hostavin N30) were chosen as the
HAhS compounds. HMTA stearate, 7-dodecylideneamino-
1,3,5-triazadamantane and PP-MA-7-amino-1,3,5-
triazadamantane were chosen as the bridged amines.
PP (Stamylan9, type P83m18, batch VI DSM, the
Netherlands) was chosen as the polymer. Films were
produced from the plastics compositions using the
process described above. The films were subjected to a
weather-resistance test and the weather resistance was
determined as described above. The results are
summarized in Tables 8 - 20.
CA 02280158 1999-08-10
- WO 98!36023 PCT/NL98/00088
-40-
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
WO 98/36023 PC'r/NL98/00088
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CA 02280158 1999-08-10
- WO 98136023 PCT/NL98/00088
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CA 02280158 1999-08-10
- WO 98!36023 PCT/NL98/00088
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
-50
m O 3 ~ ~ tr'H
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
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CA 02280158 1999-08-10
WO 98136023 PCT/NL98/00088
-52-
m o 3 ~ o
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CA 02280158 1999-08-10
- WO 98/36023 PCT/NL98/00088
- 53 -
arative ~'xperiments AK - ~.R~ Weather resistance of ,
various M astics compositions
A series of plastics compositions was
prepared using the process described above. In this
process the composition of the plastics composition was
varied using various non-HAZS stabilizers. 2-hydroxy-4-
n-octoxy-benzophenone (ChimassorbT 81), 2-(2'-hydroxy-
3',5'-di-tert-butyl-phenyl)-5-chloro-benzotriazol
(Tinuvin~ 327) and octadecyl-3-(3,5-di-tert-butyl-4-
hydroxy-phenyl)-propionate (Irganoxc 1076) were chosen
as the non-HALS stabilizers. DABCO stearate and HMTA
stearate were chosen as the bridged amines having an N-
bridgehead.
PP (Stamylanp, type P83m18, DSM, the Netherlands) was
chosen as the polymer. Films were produced from the
plastics compositions using the process descr'_bed
above. The films were subjected to a weather-resistance
test and the weather resistance was determined as
described above. The results are summarized ir. Table
21.
CA 02280158 1999-08-10
- WO 98/36023 FCT/NL98/00088
-54-
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