CA1068437A - Stabilised epoxy resins - Google Patents

Abstract

Stabilised epoxy resins Abstract of the Disclosure Epoxy resins stabilised by at least one sterically hindered cyclic amine of the formula I

Description

lQ6~437 Stabilised ePOxy resins The present invention relates to new stabilised epoxy resins the stabiliser being a sterically hindered cyclic amine.
Epoxy resins, that are polyepoxide compounds, are increasingly employed in numerous field Or use because of their well-balanced mechanical properties and their excellent processing properties. ~hey are also being used increasingly for external applications.
However, an obstacle to the general and broad application of these resins iB their inadequate light stability. Epoxy resins are deteriorated under outdoor exposure. This deterioration causes a decrease of tbe mechan-ical properties of the resin as well as discolourQtion, A sufficient light stabilisation of epox~ resins is an unsolved problem of today.
It has now been found that epoxy resins can e~fectively be stabi-lised by the addition o~ a sterically hindered cyclic amine.
Thus, the invention relates to epoxy resins stabilised by at least one sterically hindered cyclic amine of the formula I

~ 2 rc\
X N _ _Y (I) /c\
3 4 q and salts thereof in which g is 1 or 2, X represents an organicgrouping which complements the nitrogen-containing ring to give a 5-membered, 6-membered or 7-membered ring, Rl and R2 represent methyl or together represent -(CH2)5-, R3 represents methyl, R4 represents alkyl with 1-5 carbon ~toms or together with R3 represents the radicals -(CH2)4-~ -(CH2)5-~ -CH2-C(CH3~2-NH-C(CH3)2-CH2- or -CH2-C(CH3)2-N(0 )-C(CH3)2-CH2- and, if q is 1, Y denotes hydrogen, -0 , hydroxyl, alkyl, substituted alkyl, alkenyl, alkynyl, aralkyl, substituted aralkyl or acyl or, if q is 2, Y denotes alkylene, alkenylene, alkynylene, - 1 - ~3~

cycloalkylene or aralkylene.
By the above sterically hindered cyclic amine the weathering resistance of epoxide resins is improved in an unexpectedly lasting manner.
Examples of sterically hindered cyclic amines of the formula I
which are suitable for the stabilised system according to the invention, correspond to the following formulae:

R3 ~ H
yl ~ II

Rl R2 O ~ 5 III

Rl R2 n Ll ~ ~;~R6 R ~ CH3 ~ H3 Yl~ ~Y

Rl R2 3 3 ~`
1 ~ N _ O _ _ R7 VI

Rl R2 P

lQ68437 3 ~4 R

Yl ~`Rg VII

r 3$CR_CO--E~ Rlo VIII

Rl R2 I n r 3~4 Ll ~CH2 CO--El--Rlo IX

Rl R2 n ~R13 Rl R12 R3 ~4 Yl j~<p/ OR14 XI

Rl R2 ¦ ¦\o 3\/ 4 ~OR16 XII

Rl R2 106~437 1 ~ OR16 XIII

Rl R2 R3 ~ R4 OR

Yl N ~ XIV
~ OR18 3 ~ 4 IRl9-Yl _ ~ N = C _R20 XV

1 2 _ s and E ~2c32 ~Rl3 ~

Rl R2 in ~hich formulae Yl represents hydrogen, -O , hydro.xyl, alkyl, substituted aIXyl, alkenyl, alkinyl, araIkyl, substituted aralkyl or acyl, Rl and R2 represent methyl or together represent -(CH2)5-, R3 represents methyl, R4 represents alkyl with 1-5 carbon atoms or together with R3 represents the (CH2)4 , (CH2)5-, -cH2-c(cH3)2-NH-c(cH3)2-cH2- or -CH2-C(CH3)2-N(O )-C(CH3)2-CH2-, s represents 1, 2 or 3, p represents 1 to 3, n represents 1 to 4, R5 represents hydrogen, a s~turated or unsaturated, unsubstituted or substituted aliphatic, cycloaliphatic or araliphatic radical, an unsubstituted or substituted aromatic radical, a novalent to tetravalent acyl radical which is derived from an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic monobasic or polybasic carboxylic acid, from a carbonic acid or from a monobasic or polybasic phosphoric, sulphuric, boric or silicic acid, an s-triazinyl radical or a group of the formula <CH3 -Y XVII

R6 represents hydrogen, a saturated or unsaturated, unsubstituted or sub-stituted aliphatic, cycloaliphatic or araliphatic radical, a substituted or unsubstituted aromatic radical, or a monacyl radical derived from a monobasic carboxylic acid or csrbonic acid, A represents oxygen or -N-R24, wherein R24 $s hydrogen, alkyl, substituted alkyl, alkenyl, alkinyl or aralkyl, B
represents ~CeO, ~ G-S, alkylidene, substituted alkylidene or aralkyl-idene, D represents oxygen, sulphur or NH, R7 represents hydrogen, alkyl, aralkyl or a monoacyl, diacyl or triacyl radical derived from a monobasic to tribasic carboxylic acid, or a carbonic acid radical, R8 and Rg indepen-dently of one another represent alkoxycarbonyl, acyl, nitrile or phenyl, Rlo represents a saturated or unsaturated, unsubstituted or substituted, aliphatic, cycloaliphatic or araliphatic radical, an unsubstituted or sub-stituted aromatic radical or a group of the formula XVII, E represents oxygen, sulphur or ~ N-R25, wherein R25 is hydrogen, alkyl, cycloalkyl or ar~lkyl, Rll represents hydrogen or alkyl, R12 represents hydrogen, alkyl, cycloalkyl or aralkyl, R13 represents hydrogen, a saturated or unsaturated, unsubstituted or substituted aliphatic, cycloaliphatic or araliphatic radical, an unsubstituted or substituted aromatic radical, a monovalent or divalent acyl radical derived from an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic monobasic or dibasic carboxylic acid, from a carbonic acid or from a monobasic or polybasic phosphoric acid or sulphuric acid, an s-triazinyl radical, a radical of the formula XVII or, together with R12, an alkylene radical which can be interrupted by hetero-atoms, R14 and R15 independently of one another represent alkyl, cycloalkyl or aralkyl or to-gether represent alkylene, R16 represents hydrogen or acyl, with the ring Z
representing a benzene or cyclohexane ring which is unsubstituted or sub-stituted by 1-3 alkyl, cycloalkyl or aralkyl groups, R17 and Rlô represent the same alkyl group or together represent unsubstituted or substituted 1,2-ethylene, 1,3-propylene, 1,2-phenylene or a group of the formula CH ~ CH3 X o ~ XVIII

R19 represents h~drogen, alkyl, alkenyl, ar~lkyl, aryl or substituted aryl and R20 represents unsubstituted or substituted alkyl, alkenyl, arslkyl, un-substituted or substituted aryl, or a heterocyclic radical, or Rlg and R20 together represent cycloalkylidene, or correspond to one of the ~ollowing ~ormulae:

Y`~
Y2 - N ~ O XIX

Rl R2 ~2 ~ ~ Ya XX

Rl R2 w - R3 ~ -10 Y2 - N N - Ya XXI
/\
_ Rl R2 w ~ l

2 ~--NH --r 21 Rl R2 s ~ ~ ] XXIII

Rl 2

3 ~ 4 R ~ --R23 XXIV

p Y' R3 3~3y D~V

Rl R2 ~2 ~ 26 XiVl 3 ~ 4 R28 Y--~ COOR27 XXVII

in ~hich formulae Y2 denotes hydrogen, -O or methyl, s, p~ Rl, R2, R3 and R4 denote what has been mentioned above, R21 denotes a monovalent or divalent acyl radical derived from a monobasic or dibasic carboxylic acid or carbonic acid R22 denotes hydrogen, alkyl, alkoxycarbonylalkyl, aralkyl, alkylene, aralkylene or arenetriyl-tris-alkyl, R23 denotes the same as R22 or denotes a monoacyl or diacyl radical or -(CH2)1 12-COOMe, Me being hydrogen or Me l/z and Me being a dialkyl tin residue or a metal residue and z being 1-4 and the valence of that residue Me, R26 denotes alkyl, cycloalkyl, aralkyl, aryl, arylamino, alkylene, cycloalkylene or arylene, R27 denotes alkyl and R28 denotes hydrogen or alkyl with 1-5 carbon atoms, or correspond to the ~ormula R3 ~ 4 Y3 - ~ OR29 XXIX

Rl R2 wherein Rl, R2, R3 and R~ have the above mentioned meaning, Y3 repre~ents hydrogen or methyl and R29 represents alkyl, cyclo~lkyl or ara~syl, Ya iB for w bein~ 1 alkyl, substituted alkyl, alkenyl, alkinyl, aralkyl or substituted aralk~l, Ya is Por w being 2 alkylene,interrupted alkylene, alkenylene, alkinylene or bis-alkylene arene, Ya is for w being 3 T[OOC-(CH2)X-~3 with x being 1-4 and T being a trivalent hydrocarbon residue, or Ya is ~or w being

4 Q[OOC-(CH2)X-]4 with x being 1-4 and Q being a tetravalent hydrocarbon residue, or in a compound XX Ya is -CO-XXX-R , X being 0 or NH and R
being a hydrocarbyl residue having from 1-20 C-atoms and w is 1 or 2 or cor-responds to the ~or~ula z ~o---NH - Rxxx ~ N ~ XXX

L _ i xxx 1 or 2 as well as salts thereo~, wherein YXxx is 0 , hydrogen or alkyl with 1-4 csrbon atoms, RXxx is optionally substituted hydrocarbyl residue with 1-20 carbon atoms and Z is S or pre~erably 0, or corresponds to the formula Rb ~ Rb XXXI

XXXl wherein YXxxi is hydrogen, hydroxy, 0 , alkyl, alkenyl, alkinyl or alkoxy-alkyl, Rb is alkyl and Rc is alkyl or phenethyl, or corresponds to the ~or-mula ~068437 3 ~ 3 OH ~ CH
XXXlll N ~ XXXlll XXXIII
/ ~ HO CH3 RXXX111 and RXXX111~ being same or different and each hydrogen, alkyl, ~lkenyl, alki~yl, aralkyl, hydroxyalkyl, alkoxyalkyl~ aliphatic or aromatic acyloxyalkyl, cyanoalkyl,-halogenoalkyl, epoxyalkyl, alkoxycarbonylalkyl, aliphatic acyl, alkoxycarbonyl or aralkoxycarbonyl, or corresponds to the ~ormula Rxxxl~ ~ XXXIV

3 H3 Rq xxxly g RXXX111 and Rm, Rn, Ro, Rp and R being same or dif-ferent and bydrogen or alkyl.
An s-tria~inyl radical can be substituted by halogen, alkylamino, alkylthio or a group of formula XVII.
Preferably, in the formulae given for sterically hindered cyclic amines as defined above Yl denotes hydrogen, -O , alkyl with 1-8 carbon atoms, halogenoalkyl with 1-5 carbon atoms, cyanoalkyl with 1-5 carbon atoms, epoxyaIkyl with 3-4 carbon atoms, hydroxyalkyl with 8-12 carbon atoms, acyloxyaIkyl with 4-20 carbon atoms, aminoalkyl with 2-4 carbon atoms, acyl-amino uith 2-18 carbon atoms, alkoxycarbonylalkyl with 3-21 carbon atoms, alkoxyalkyl with 3-20 carbon atoms, aralkyl with 7-20 carbon atoms, alkenyl with 3-6 carbon atoms or alkinyl with 3-6 carbon atoms, Rl and R2 denote methyl, R3 and R~ denote methyl or together denote -(CH2)5 or -CH2-C(CH3)2-NH-C(CH3)2-CH2-, s denotes 1, p denotes 1, n denotes 1 or 2, R5 denotes hydrogen, alkyl with 1-12 carbon atoms, alkenyl with 3-4 carbon atoms, cycloalkyl w~th 6-8 car~on atoms, aralkyl with 7-9 carbon atoms, aryl with 6-10 carbon atoms, an acyl group which i~ derived from an aliphatic car-boxylic acid with 1-20 carbon atoms, from an unsaturated carboxylic acid with _ g _ 3-12 carbon atoms, from a cycloaliphatic carboxylic acid with 7-12 carbon atoms, from an araliphatic carboxylic acid with 8-12 carbon atoms, from a hydroxyphenylalkylcarboxylic acid with 9-16 carbon atoms, from an aliphatic carboxylic acid with 3-21 carbon atoms of which the carbon chain is inter-rupted by sulphur or oxygen, from an aromatic carboxylic acid with 7-12 car-bon Atoms~ fro~ a hydroxyphenylcarboxylic acid with 7-15 carbon atoms, from carbonic acid, from an aliphatic dicarboxylic acid with 2-20 carbon atoms, fro~ an aliphatic dicarboxylic acid 4-8 carbon atoms o~ which tbe chain is i~lterrupted by oxygen or sulphur, from an aromstic dicarboxylic acid with 8-12 carbon atoms or from a carba~ic or thiocarbamic acid which is sub-stituted at the nitro~en by alkyl with 1-18 carbon atoms, cycloalkyl with 6-ô carbon atoms, aralkyl with 7-9 carbon atoms or aryl with 6-10 carbon atoms, R6 denotes hydrogen, alkyl with 1-20 carbon atoms, alkenyl with 3-6 carbon atoms, alkinyl with 3-6 carbon atoms, cycloaIkyl with 6-8 carbon atoms, alkylcycloalkyl with 7-10 carbon atoms, aralkyl with 7-12 carbon atoms, aryl with 6-10 carbon atoms, alkylphenyl with 7-10 carbon atoms, epoxyalkyl with 3-5 carbon atoms, halogenoalkyl with 1-5 carbon atoms, hydroxyalkyl with 2-5 carbon atoms, alkoxyalkyl with 3-20 carbon atoms, alkoxycarbonylalkyl with 3-21 carbon atoms, acyloxyalkyl with 4-21 carbon atoms, alkylene with 4-8 carbon atoms, 3-oxapentamethylene, 3-thiapenta-methylene, phenylene, alkylphenylene or p-xYlylene, A denotes , NH or _ N-R24, wherein R24 denotes hydrogen, alkyl with 1-6 carbon atoms, glycidyl, alkenyl with 3-4 carbon atoms, alkinyl with 3-~ carbon atoms or aralkyl with 7-9 carbon atoms, B denotes ~ C=0, /C=S or alkylidene with 5-18 carbon atoms, D denotes oxygen or ~ NH, R7 denotes hydrogen, alkyl with 1-8 carbon atoms, araIkyl with 7-9 carbon atoms, an acyl group which is derived from an aliphatic carboxylic acid with 2-12 carbon atoms, from benzoic acid or from a carbamic acid which is substituted at the nitrogen by alkyl with1-18 car-bon atoms, benzyl or phenyl, R8 and Rg independently of one another denote alkoxycarbonyl with 2-6 carbon atoms, benzoyl, nitrile or phenyl, Rlo denotes alkyl with 1-18 carbon atoms, cycloalkyl with 6-8 carbon atoms, aralkyl with 7-12 carbon atoms, aryl with 6-10 carbon atoms, alkylene with 2-18 carbon 1~68437 atoms, aralkylene with 8-12 carbon atoms, arylene with ~-12 carbon atoms, 2,2,6,6-tetramethyl piperidinyl-4 or 1,2,2,6,6-pentamethylpiperidinyl-4, E denotes oxygen, sulphur or ~N-R25, wherein R25 is hydrogen, alkyl with 1-12 carbon atomsl cyclohexyl or benzyl, Rll denotes hydrogen or alkyl with 1-12 carbon atoms, R12 denotes hydrogen, alkyl with 1-8 carbon atoms, cyclo-hexyl or benzyl, R13 denote~ hydrogen, alkyl with 1-8 carbon atoms, alkenyl with 3-4 carbon atoms, cycloalkyl with 6-8 carbon atoms, aralkyl with 7-9 carbon atoms, phenyl, ~lkylphenyl with 7-12 carbon atoms, or an acyl group which is deri~ed from an aliphatic monocarboxylic acid with 1-20 carbon stoms, from an unsaturated carboxylic acid with 3-12 carbon ~toms, from an aliphatic carboxylic acid with 3-21 carbon atoms which is substituted by alkoxy or alkylthio groups, from an aromatic carboxylic acid with 7-10 carbon atoms or from a carbamic or thiocarbamic acid which is substituted at the nitrogen by alkyl with 1-18 carbon atoms, cycloalkyl with 6-ô carbon atoms, aralkyl with 7-9 carbon atoms or aryl with 6-12 carbon atoms, R14 and ~ 5 denote alkyl with 1-12 carbon atoms, cyclohexyl, benzyl, halogenoalkyl with 2-5 carbon atoms or, together, ethylene or 1,2-propylene, R16 denotes hydro-gen or the radical of an acyl group which is derived from an aliphatic car-boxylic acid with 2-18 carbon atoms, from an aromatic carboxylic acid with 7-10 carbon atoms or from a carbamic acia substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, with the ring Z representing a benzene or cyclohexane ring which is not substituted further or is substitut-ed further by 1-2 alkyl groups with 1-5 carbon atoms, R17 and R18 denote alkyl with 1-8 carbon atoms, alkylene with 2-5 carbon atoms, 1,2-phenylene or a ~roup of the formula ~~
XXXV

Rlg denotes hydrogen, alkyl with 1-4 carbon atoms, alkenyl with 3-4 carbon atoms, benzyl or phenyl, R20 denotes alkyl with 1-12 carbon atoms, alkenyl with 3-4 carbon atoms, aralkyl with 7-9 carbon atoms, aryl with 6-10 carbon atoms, alkoxyaryl with 7-9 carbon atoms, furyl, thienyl or, together with Rlg, -(CH2)5-, R21 denotes an acyl group which is derived from an aliphatic carboxylic acid with 1-20 carbon atoms, from an aliphatic carboxylic acid with 3-20 carbon atoms Or which the chain is interrupted by oxygen or sulphur atoms, rrom a cyclosliphatic carboxylic acid with 7-12 carbon atoms, ~rom an araliphatic carboxyllc ac~d with ~-12 carbon atoms, from an bydroxyaraliphatic monocarboxylic scid with 9-16 carbon atoms, from an aromatic carboxylic acid with 7-15 carbon ~toms or from a hydroxybenzoic acld with 7-15 carbon atoms, 1~ R22 denotes hydrogen, alkyl with 1-20 carbon atoms, benzyl, alkylene with 1-20 carbon atoms or alkoxycarbonylalkyl with 2-26 carbon atoms, R23 denotes the same as R22 or denotes an acyl group which is derived from an aliphatic carboxylic acid with 2-20 carbon atoms, ~rom benzoic acid or from a carbamic acid substituted at the nitrogen by alkyl with 1-24 carbon atoms or phenyl, R26 denotes alkyl with 1-16 carbon atoms, cycloalkyl with 6-8 carbon atoms, araLkyl with 7-12 carbon atoms, aryl with 6-10 carbon atoms or arylamino with 6-10 carbon atoms, R27 denotes alkyl with 1-8 carbon atoms, R28 denotes hydrogen or methyl, R29 denotes alkyl with 1-18 carbon atoms, cycloalkyl with

5-6 carbon atoms or aralkyl with 7-12 carbon atoms. In a compound Or form~la III R5 is also a residue -0-C0-Rx-CO-OMe, Me beinB as above hydrogen or Me l/z and z being 1-4 and the valence Or the metal residue Me, and Rx is alkylene, oxa-alkylene or thiaalkylene.
In a compound Or formula X R13 is also a residue -NH-C0-Rx-CO-OMe, Me being as above hydrogen or Me l/z and z being 1-4 and the valence o~ the metal residue Me, and Rx is alkylene, oxa-alkylene or thioalkylene.
Yl is above all hydrogen, -0 , alkyl ~ith 1-8 C atoms or alkenyl ~ith 2-7 C atoms, especially hydrogen, 0 , methyl or allyl.
Particularly preferentially, in the formulae given for sterically hindered cyclic amines and in the formulae II-VIII, Yl denotes hydrogen, -O
or methyl, Rl, R2, R3 and R4 denote methyl, s denotes 1, p denotes 1, n denotes 1 or 2, R5 denotes hydrogen, or an acyl group which is derived from an aliphatic carboxylic acid with 1-18 carbon atoms, from acrylic acid or methacrylic acid, from benzoic acid or from sn alkylbenzoic acid with ô-ll carbon atoms, from salicylic acid, from an aliphatic dicarboxylic acid with 4-14 carbon atoms, from terephthalic acid, from isophthalic acid or from a csrba~ic or thiocarbamic acid which is substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, ~6 denotes alkyl with 1-12 carbon atoms, allyl, benzyl, cyclohexyl, glycidyl, hydroxyethyl, alkoxyalkyl with 3-10 carbon atoms, alkoxycsrbonylalkyl with 3-14 carbon atoms, hexamethylene or 3-oxapentamethylene, A denotes ~ NH or ~ N-R24, wherein R24 is bydrogen, methyl, ethyl or benzyl, B denotes ~ C=0, D denotes oxygen, R7 denotes hydro-gen, methyl, benzyl, benzoyl or p~lenylcarbamoyl, R8denotes nitrile, Rg denotes ethoxycarbonyl, phenyl or benzoyl, Rlo denotes alkyl with 6-8 carbon stoms, cyclohexyl, benzyl, alkylene with 4-12 carbon atoms, xylylene, phenyl-ene or 2,2,6,6-tetramethyl-piperidinyl-4, E denotes oxygen or ~MH, Rll denotes hydrogen, R12 denotes hydrogen or methyl, R13 hydrogen or an acyl group which is derived from an aliphatic carboxylic acid with 1-18 carbon atoms, from acrylic or methacrylic acid, from a benzoic acid with 7-10 carbon atoms, from salicylic acid or from a carbamic or thiocarbamic acid which i9 substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, R14 and R15 denote alkyl with 4-8 carbon atoms, benzyl or chloroethyl, R16 denotes hydrogen or the radical of an acyl group which is derived from an aliphatic carboxylic scid with 2-12 carbon atoms, from benzoic acid or from a N-slkyl-carbamic acid with 2-8 carbon atoms, with the ring Z repre-senting a benzene ring which is substituted further by 1-2 methyl, isopropyl or tert.-butyl groups, ~ 7 snd R18 denote methyl, ethylene, 1,3-propylene or a group of the formuls XXXV, Rlg denotes hydrogen, R20 denotes alkyl with 1-8 carbon atoms, benzyl, phenyl, alkoxyphenyl with 7-10 carbon atoms or to-gether with Rlg~ -(CH2)5-, R21 denotes an acyl group which is derived from an aliphatic monocarboxylic acid with 3-18 carbon atoms of which the chain can be interrupted by sulphur atoms, from phenylacetic acid, from benzoic acid or from salicylic acid, R22 denotes hydrogen, alkyl with 6-18 carbon atoms or benzyl, R23 denotes the same as R22 or an acyl group which is derived from an aliphatic carboxylic acid with 3-18 carbon atoms, from benzoic acid or 1~68437 from a carbamic acid which is substituted at the nitrogen by alkyl with 1-12 carbon atoms or phenyl, R24 denotes hydrogen, methyl, ethyl or benzyl, R26 denotes alkyl with 4-18 carbon atoms, benzyl or phenyl, R27 denotes alkyl with 1-4 carbon atoms, R28 denotes hydrogen, R29 denotes alkyl with 4-18 carbon atoms or benzyl.
f Y Y R R R R R R R R R R R R
I ~ 1' 4' 5' 6' 7' 10' 11' 12' 13' 14' 17' 18' 19' R R R R24, R25, R26~ R27~ R2g, R2g, Ya~ Rxx' xxx' xxx xxx d f' xxxlll' Rxxxlll " Rm~ Rn~ Ro, Rp and Rq denote alkyl, then this is, for example, within the scope of the indicated limits, methyl~ ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, octadecyl, eicosyl, iso-propyl, iso-butyl, tert~-butyl, iso-pentyl, tert~-amyl, iso-octyl or tert~-octyl.
If Y, Yl, R5, R6, R13, Rlg, R20~ Ya~ Rxx~ Rxxx~ Yxxxl~ Rxxx R xxlll' and RXXX1V' denote alkenyl and/or alkinyl, this is, for example, within the scope of the indicated limits, allyl, methallyl, 3-hexenyl, 4-octenyl, 10-undecenyl, propargyl, but-l-inyl, but-2-inyl or l-hexinyl~
1 5 6 7' 10' 12' 13' R14- R15, Rlg, R20~ R22~ R23 R24, R25, R26~ R2g, Ya~ Rxx~ Yxxx' Rxxxlll' Rxxxlll' xxxlv aralkyl or hydroxyaralkyl, this,is, for example, within the scope of the 2Q indicated limits, benzyl, -methylben2yl, ,~-dimethylben2yl, naphthyl-l- methyl or 2-hydroxy-2-phenylethyl~
5' 6' Rlo' R12' R13~ R14~ Rls, R2s, R26 and R29, denote cyclo-alkyl or alkylcycloalkyl, this is, for example, cyclohexyl, cyclooctyl, 4-methylcyclohexyl or 4-tert~-butylcyclohexyl~
If Yl~ R6~ R14~ Rls. Rxxxlll~ Rxxxlll- and Rxxxlv denote halogen-alkyl, this is, for example, 2-chloroethyl, 2-bromoethyl, 2-chloropropyl, 3-bromopropyl, 4-chlorobutyl or 2-chloro-2-phenylethyl~
f Yl ' Rxxxl 11' Rxxxlll' and Rxxxlv denotes cyanoalkyl, this is, for example, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl or 4-cyanopentyl~
If Yl, R6, Rxxx~ Rxxxill~ Rxxxlv denote epoxyalkyl, this is, for example, glycidyl, 2,3-epoxy-3-methylpropyl, 3,4-epoxy-n-butyl or 4,5-epoxy-n-pentyl~

1' 6' Rxxxll~' Rxxxlll' and Rxxxlv denote hydroxyalkyl, this is, for example, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxypentyl.
If Yl, R6, Rxxxlll' Rxxx~ and Rxxxlv denote alkoxyalkyl, this is, for example, 2-methoxy-ethyl, 2-ethoxyethyl, 2-propoxyethyl, 3-methoxy-propyl, 2-butoxyethyl, 4-methoxypentyl, 2-octoxyethyl, 2-dodecyloxyethyl or ~oct~decyloxyethyl.
I~ Yl among others are acyloxyalkyl, this is e.~. 2-acetoxyethyl, 2-acetoxypropyl, 3-acetoxypropyl, 4-propionyloxybutyl, 2-(methylcarbamoyloxy)-ethyl, 2-(ethylcarbamoyloxy)ethyl, 2-(phenylcarbamoyloxy)ethyl, 2-(alkyl-thiocarbamoyloxy)ethyl, 4-propionyloxy-pentyl or 2-octadecanoyloxyethyl.
If Yl denotes aminoalkyl, this is, for example, 2-aminoethyl, 2-dimethylaminoethyl, 3-dimethylaminopropyl or 2-octylaminoethyl.
If Y, R6, R22 and others are alkoxycarbonylPlkyl, this is, for example, within the scope o~ the indicated limits, 2- methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylethyl, hexyloxycarbonylmethyl, methoxycarbonylpropyl, 2-dodecyloxycarbonylethyl, 2-octadecyloxycarbonylethyl or 2-eicosyloxycarbonylethyl.
If R5, R6, Rlo and others denote aryl, this is, for example, within the scope of the indicated limits, phenyl or naphthyl.
If R5 and R13 denote alkylphenyl, this is, for example, within the scope of the indicated limits, tolyl, 2,4-xylyl, 2,~-xylyl, 4-tert.-butyl-phenyl, 4-tert.-octylphenyl, methylnaphthyl or dimethylnaphthyl.
If Y, R6, Rlo, R17, R18 and others denote alkylene, this is, for example, within the scope of the indicated limits, methylene, ethylene, propylene, butylene, hexamethylene, octamethylene, dodecamethylene or octa-decamethylene.
If Rlo and R22 denote aralkylene, this is, for example within the scope of the indicated limits, p-xylylene, 1,4-bis(ethylene)phenylene or dimethyl-p-xylylene.
If B denotes alkylidene, this is, for example, within the scope of the indicated limits, l-pentylidene, l-hexylidene, l-octylidene, l-dodecyl-idene or l-octadecylidene.
If Rlo denotes alkanetriyl or slkanetetrayl, this is, for example, within the scope of the indicated limits, one of the radicals of the formulae XXXVI

l H2_ l H2_ l H2_ CH3-C-CH2- CH3CH2-C-CH2- CH3cH2cH2-c-cH2 XXXVI
ltl2_ CH~- CH2-C~-C-CH2- or -~H2-C-CH2-0-CH2-1 CH2 If R6, Rlo and R26 denote arylene,this is, for example, within the scope of the indicated limits, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,4-naphthylene, 1,5-naphthylene, 2,6-nsphthylene, dimethyl-phenylene or dimethylnaphthylene.
If R22 denotes al~ylene-bis-toxycarbonylalkyl), this is, for example, within the scope of the indicated limits, ethylene-bis-(oxycarbonyl-methyl~, ethylene-bis-(oxycsrbonylethyl), 1,2-propylene-bis-loxycarbonyl-ethyl), 1,4-tetramethylene-bis-(oxycarbonylpropyl) or 1,6-hexamethylene-bis-(oxycarbonylethyl).
If Y. ~1~ R5, R7, R13, R16 and others denote an acyl group which is derived from an aliphatic, unsaturated, cycloaliphatic or araliphatic carboxy-lic acid or from an aliphatic or aromatic carboxylic acid interrupted by sulphur or oxygen, this is, for example, within the scope of the indicated limits, formyl, acetyl, propionyl, butyroyl, hexanoyl, heptanoyl, octanoyl, 2-ethyl-hexanoyl, 2,2,4-trimethylpentanoyl, decanoyl, dodecanoyl, tetradecanoyl, hexa-decanoyl, octadecanoyl, eicosoyl, acryloyl, methacryloyl, crotonoyl, 10-un-decenoyl, 9-octadecenoyl, phenylacetyl, ~-phenylpropionyl, ~-trimethylphenyl-propionyl, (4-hydroxy-3,5-di-tert.-butyl-phenyl)acetyl, ~-~4-hydroxy-3,5-di-tert.-butyl-phenyl)propionyl, ~-(3-tert.-butyl-4-hydroxy-5-methyl-phenyl) propionyl, cyclohexanecarbonyl,4-tert.-butyl-cyclohexanoyl, ~-methylthio-propionyl, methylthioacetyl, ~-octylthiopropionyl, ~-dodecylthiopropionyl, ~-octadecylthiopropionyl, butylthioacetyl, octylthioacetyl, cinnamoyl, benzoyl, o-, m- or p-toluoyl, m-chlorobenzoyl, p-tert.-butylbenzoyl, 3,5-di-tert.-butyl-4-hydroxybenzoyl or 2,4-dimethylbenzoyl.
If R5, ~ , R13, R16, R21 and others denote an acyl ~roup which is derived from an aliphstic dicarboxylic acid oP which the chain can be inter-rupted by oxy~en or sulphur, or is derived from sn aromatic dicarboxylic acid, this is, for example, ~ithin the scope of the indicated limlts, the div~lent radical of oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic or sebacic acid, 1,12-dodecanedicarboxylic ~cid or l,lô-octadecanedicarboxylic acid, thiodiacetic acid, thiodipropionic acid, oxy-dipropionic acid, phthalic acid, isophthalic acid, terephthalic acid, dimethylterephthalic acid, tetrahydrophthalic acid or hexahydrophthalic acid.
If R5, R7, R13, R16 and R23 denote the radical of a carbamic acid or thiocarbamic acid, this is, for example, within the scope of the indicated limits, carbamoyl, N-methyl-, N-ethyl-, N-propyl-, N-isopropyl-, N-butyl-, N-pentyl-, N-octyl-, N-decyl-, N-dodecyl-, N-octadecyl-, N-allyl-, N-methallyl-, N-undecenyl-, N-cyclohexyl-, N-methylcyclohexyl-, N-benzyl-, N-(~-phenethyl)-, N-phenyl-, N-o-tolyl-, N-p-tolyl-, N-2,4-xylyl-, N,N-dimethyl-, N-methyl-N-ethyl-, N,N-diethyl-, N,N-diisopropyl- or N,N-di-n-butyl-carbamoyl or the corresponding thiocarbamoyl radicals.
If R23 denotes the radical of an alkylene- or arylene-bis-carbamic acid, this is, for example, within the scope of the indicated limits, ethylene-bis-carbamoyl, hexamethylene-bis-carbamoyl, 1,4-phenylene-bis-carbamoyl or tolylene-bis-carbamoyl. If R5 denotes an s-triazinyl radical, this is, for example, within the scope of the indicated limits, the s~
triazinyl group itself, l-chloro-s-triazinyl, 1,3-dichloro-s-triazinyl, 1-ethylamino-s-triazinyl, l-isopropylamino-s-triazinyl ~nd 1,3-dimethylthio-s-triazinyl radicals".

If R8, Rg and others denote alkoxycarbonyl, this is, for example, within the scope of the indicated limits, methoxy-, ethoxy-, propoxy-, butoxy-, iso-butoxy-, pentyloxy-, hexyloxy-, octoxy- or dodecyloxy-carbonyl.

1~68437 If any of the above radicals denotes aIkoxy, this is, for example, within the scope o~ the indicated limits, methoxy, ethoxy, propoxy, butoxy, ~-methoxyethoxy, pentyloxy, iso-butyloxy, octoxy, dodexyloxy, tetradecyloxy, octadecyloxy or eicosyloxy.
Furthermore, acyloxy is, for example, within the scope o~ the indicated limits, acetoxy, propionyloxy, butyroyloxy, 2-ethylhexanoyloxy or lauroyloxy.
If R26 denotes arylamino, this is, ~or example, within the scope o~ the indicated limits, phenylamino, p-tolylamino or p-tert.-butylphenyl-amino.
I~ Y and others denote acylamino, this is, for example, within the scope of the indicated limits, acetyl-, propionyl-, butyroyl-, pentanoyl-, 2-ethylhexanoyl-, lauroyl-, stearoyl-, phenylacetyl-, acryloyl-, methacryloyl-or cyclohexylcarbonyl-amino.
Examples o~ compounds of the formula I are:
I. 1. 4-Benzoyloxy-, I. 2. 4-Salicyloyloxy-, I. 3. 4-Capryloyloxy-, I. 4. 4-Stearoyloxy-, I. 5. 4-(~-3,5-di-tert.-butyl-4-hydroxyphenyl-propionyloxy)- and I. 6. 4-(3,5-di-tert.-butyl-4-hydroxybenzoyloxy)-2,2,6,6-tetramethyl-piperidine, I. 7. 4-Benzoyloxy-, I. 8. 4-Salicyloyloxy-, I. 9. 4-Stearoyloxy- and I. 10. 4-tert.-butylbenzoyloxy-1,2,2,6,6-pentamethylpiperidine.
I. 11. Bis-(2,2,6,6-tetramethyl-4-piperidyl)-sebacate.
I. 12. Bis-(2,2,6,6-tetramethyl-4-piperidyl)-suberate.
I. 13. Bis-(2,2,6,6-tetramethyl-4-piperidyl)-dodecanedioate.
30 I. 14. Bis-(1,2,2,6,6-pentamethyl-4-piperidyl)-sebacate.
I. 15. 4-Capryloyloxy-l-propyl-2,2,6,6-tetramethylpiperidine.
I. 16. 4-Capryloyloxy-l-allyl-2,2,6,6-tetramethylpiperidine.

I. 17. 4-Benz~ylamido-, I. lô. 4-Acryloylamido- and I. 19. 4-Stearoylamido-2,2,6,6-tetramethylpiperidine.
I. 20. N,N'-Bis(2,2,6,6-tetramethyl-4-piperidyl)oxalamide.
I. 21. N-(2,2,6,6-Tetramethyl-4-piperidyl)cyclohexanoneimine.
I. 22. (2,2,6,6-Tetramethylpiperidin-4-one)-aæine.
I. 23. 3-n-Butyl-, I. 24. 3-n-Butyl-8-methyl-, I. 25. 3-n-Octyl-, I. 26. 3-n-Octyl-8-methyl-, I. 27. 3-Allyl-, I. 28. 3-Allyl-8-methyl-, I. 29. 3-Glycidyl-, I. 30. 3-Glycidyl-8-methyl-, I. 31. 3-Octadecyl-, I. 32. 3-Cyclohexyl-, I. 33. 1,3,8-Trimethyl-, I. 34. 1,8-Dimethyl-3-hexamethylene-bis-, I. 35. 1,8-Dimethyl-3-(3-oxapentamethylene-bis)-, I. 36. 8-Methyl- and I. 37. 3-n-Octyl-8-benzyl-7,7,9,9-tetramethyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione.
I. 38. 1,3,8-Triaza-2-n-undecyl-4-oxo-7,7,9,9-tetramethyl-spiro[4.5]decane.
I. 39. 2,4,6-Tris-(2,2,6,6-tetramethyl-4-piperidyloxy)-s-triazine.
I. 40. 2,4,6-Tris-(1,2,2,6,6-pentamethyl~4-piperidyloxy)-s-triazine.
I. 41. 2,4,6-Tris-(2,2,6,6-tetramethyl-4-piperidylamino)-s-triazine.
I. 42. 2,2,6,6-Tetramethyl-4-~-cyanoethoxy-piperidine.
I. 43. 1,2,2,6,6-Pentamethyl-4-lauroyloxy-piperidine.
I. 44. Triacetone-amine-oxime.
I. 45. Ethyl (2,2,6,6-tetramethylpiperidinylidene-4)-acetate.
I. 46. (2,2,6,6-Tetramethylpiperidinyl-4-)acetic acid octadecyl ester.

I. 47. Ethyl (1,2,2,6,6-pentamethylpiperidinyl-4)-acetate.
I. 48. 2,2,6,6-Tetramethyl-4-hydroxy-(2,2,6,6-tetramethylpiperidinyl-4-acetate).
I. 49. N,N'-Bis-(2,2,6,6-tetramethylpiperidinyl-4-acetyl)-ethylene-diamine.
I. 50. 2,2,6,6-Tetramethy1-4-(~-capryloylamino-ethyl)-piperidine.
I. 51. N,N'-Bis-~-(2,2,6,6-tetramethylpiperidinyl-4)-ethyl]-oxalamide.
I. 52. 2,6-Dimethyl-4-(2,2,6,6-tetramethylpiperidinyl-4)-phenol.
I. 53. Bis-(2,2,6,6-tetramethylpiperidinyl-4)-adipoyldihydrazone.
I. 54. 2,2,6,6-Tetramethylpiperidinyl-4-capryloyl-hydrazone.
I. 55. 2,2,7,7-Tetramethyl-hexahydro-5H-1,4-diazepin-5-one.
I. 56. 5,5,7,7-Tetramethylpiperidino[5.4-C]-~3-thiazoline-2-spiro-4'-(2',2',6',6'-tetramethylpiperidine).
I. 57. Cyclohexane-l-spiro-2'-(4'-oxoimidazolidine)-5'-spiro-1"-cyclo-hexane.
I. 58. 7,15-Diazadispiro]5,1,5,3]hexadecane.
I. 59. 4-n-Octadecyl-2,2,6,6-tetramethyl-3,5-diketopiperazine.
I. 60. 15,15'-Sebacoyl-bis(7,15-diazadispiro]5,1,5,3]hexadecane).
I. 61. l-n-Octyl-, I. 62. l-n-Dodecyl-, I. 63. l-~-Stearoyloxyethyl- and I. 64. 1-n-Octoxycarbonylmethyl-2,2,6,6-tetramethylpiperidine.
I. 65. 2,2,6,6-Tetramethyl-4-benzoylpiperidin-1-oxyl.
I. 66. Bis-(2,2,6,6-tetramethyl-4-piperidinyl-1-oxyl)-I. 67. 7,14-Diaza-15-oxo-dispiro[5.1.5.2]pentadecan, I. 68. 1,3,5-Tris(1,2,2,6,6-pentamethyl-4-piperidinylamino)-s-triazine, I. 69. 1-Chloro-3,5-bis(2,2,6,6-tetramethyl-4-piperidinylamino)-s-triazine, I. 70. 1-Chloro-3,5-bis(2,2,6,6-tetramethylpiperidinyloxy)-s-triazine, I. 71. N-cyclohexyl-(2,2,6,6-tetramethylpiperidinyl-4-)acetamide, I. 72. N-cyclohexyl-(1,2,2,6,6-pentamethylpiperidinyl-4)acetamide.
Preferred are amine stabilisers of formula II, III, IV, IX~X, XI~, XIX, XX, XXI, XXIII, XXIV, XXVII, XXX, XXXI, XXXII, XXXIII and XXXIV, and of these especially II, III, IV, XIV, XIX, XX, XXI, XXXIII and XXXIV.
Especially preferred are sterically hindered cyclic amines of the formula CH ~ ~ R6 XXXVII
3 H3 - in iA which Yl denotes hydrogen, -0' or methyl, R6 denotes alkyl with 1-12 car-bon atoms, allyl, benzyl, cyclohexyl, glycidyl, hydiroxyethyl, alkoxyalkyl with 3-10 carbon atoms, alkoxycarbonylal~yl with 3-14 carbon atoms, hexa-methylene or 3-oxapentamethylene, R24 denotes hydrogen, methyl, ethyl or benzyl, and n denotes 1 or 2, or of the formula . y )~ i 1 - ~ 0_ ~ R5 XXXVIII

H3C CH3 - in in which Yl denotes hydrogen, -0 or methyl, R5 denotes an acyl group which is derived from an aliphatic carboxylic acid with 1-18 carbon atoms, from acrylic acid or methacrylic scid, from a benzoic acid with 7-11 carbon atoms, from salicylic acid, from an aliphatic dicarboxylic acid with 6-14 carbon atoms, from terephthalic acid, from isophthalic acid, from ~-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionic acid or from 3,5-di-tert.-butyl-4-hydroxy-benzoic acid and n denotes 1 or 2. R5 also denotes an s-triazinyl radical which has a chlorine substituent and n is 2.

The new stabilised systems according to the invention make it pos-sible e~fectively to protect epoxide polymers, against the harmful influence of W radiation, heat and oxygen, without discolouration.
In principle, all classes of epoxide compounds, provided that they contain more than one epoxide group in the molecule, are suitable for the invention.
Suitable polyepoxide compounds are, in particular, such compounds having on average more than one glycidyl group or ~-methylglycidyl group bound to a hetero atom (e.g. sulphur, preferably oxygen or nitrogen); special mention may be made of di- or polyglycidyl ethers of polyvalent aliphatic alcohols such as 1,4-butanediol, or polyalk~lene glycols such as poly-propylene glycols; di- or polyglycidyl ethers of cycloaliphatic polyols such as 2,2-bis-(4'-hydroxycyclobexyl)-propane; di- or polyglycidyl ethers of polyvalent phenols such as resorcin, bis-(p-hydroxyphenyl)-methane, 2,2-bis-(p-hydro.Yyphenyl)-propane (= diomethane), 2,2,-bis-(~'-hydroxy-3',5'-dibromo-phenyl)-propane, 1,1,2,2-tetrakis-(p-hydroxyphenyl)-ethane; or of conden~a-tion products of phenols with formaldehyde obtained under acid conditions, such as phenol/novolaks and cresol/novolaks; di- or poly-(~-methylglycidyl)-ethers of the above mentioned polyvalent alcohols or polyvalent phenols;
polyglycidyl esters of polyvalent carboxylic acids such as phthalic acid, terephthalic acid, ~ -tetrahydrophthalic acid and hexahydrophthalic acid;
N-glycidyl derivatives of amines, amides and heterocyclic nitrogen bases such as N,N-diglycidylaniline, N,N-diglycidyl-toluidine, N,N,N',N'-tetra-glycidyl-bis-(p-aminophenyl)-methane; triglycidylisocyanurate; N,N'-diglycidylethyleneurea; N,N'-diglycidyl-5,5-dimethylhydantoin, N,N'-diglycidyl-5-isopropylhydantoin; N,N'-diglycidyl-5,5-dimethyl-6-isopropyl-5,

6-dihydrouracil, 1-glycidyloxymethyl-3-glycidyl-5,5-dimethyl-5,6-dihydro-uracil, l-glycidyl-3-(~-glycidyloxyethyl)-5,5-dimethylhydantoin, bis-(3-glycidyl-5,5-dimethylhydantoinyl-1)-methane and 1,6-bis-(1'-glycidyl-5',5'-dimethylhydantoinyl-3')-hexane.
Of the particularly suitable cycloaliphatic epoxide compounds, mention may be made, for example, of those compounds of the formulae:

~CH2 ~ /CH2 o~lH Hl - C - O - CH2 - CH HC\ XXXIX

C ~ HC

CH2 ~ 22 ~ CH2 ( = 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, ~CH2 ~CH2 /CH Hf cl - 0 - CH2 - CH HC~

( = 3,4-epoxy-6-methylcyclohexylmethyl-3',4'-epoxy-6'-methylcyclohexane-carboxylate), and / CH2~ ~CH2--O ~ ~CH2 CH C \ /CH CH HC
o ¦ ¦ CH2-- ¦ ¦ b XLI
CH CH C ~ HC

( = 3,4-epoxyhexahydrobenzal-3',4'-epoxycyclohexane-1',1'-dimethanol).
~ he epoxide compounds together with the stabiliser as defined above react with customary curing agents for polyepoxide compounds and can there-fore be crosslinked or cured by addition of such curing agents, analogously to other polyfunctional epoxide compounds or epoxide resins. Possible curing agents of this nature are basic or acid compounds, especially anhydride com-pounds.
As examples of suitable curing agents there may be mentioned:
amines or amides, such as aliphatic, cycloaliphatic or aromatic, primary, secondary and tertiary amines, for example monoethanolamine, ethylenediamine, hexamethylanediamine, trimethylhexamethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N,N-dimethylpropylenediamine-1,3, N,N-diethylpropylenediamine-1,3, bis-(4-amino-3-methyl-cyclohexyl)-methane, 3,5,5-trimethyl-3-(aminomethyl)-cyclohexylamine ("isophorone-diamine"), Mannich bases, such as 2,4,6-tris-(dimethylaminomethyl)-phenol;
m-phenylenediamine, p-phenylenediamine, bis-(4-aminophenyl)-methane, bis-(l~-aminophenyl)-sulphone and m-xylylenediamine; N-(2-aminoethyl)-piperazine;

adducts of acrylonitrile or monoepoxides, such as ethylene oxide or propylene oxide, to polyaIkylenepolyamines, such as diethylenetriamine or triethylene-tetra~ine; adducts of polyamines, such as diethylenetriamine or triethylene-tetramine in excess, and polyepoxides, such as diomethanepolyglycidyl-ethers;
ketimines, ~or example from acetone or methyl ethyl ketone and bis(p-amino-phenyl)-methane; adducts of monophenols or polyphenols and polyamines; poly-a~ides, especially those ~rom aliphatic polya~ines, such as diethylene-triamine or triethylenetetramine, and dimerised or trimerised unsaturated ~atty aQids, such as dimerised linseed oil fatty acid;polymeric polysulphides;
dicyandiamide, aniline-formaldehyde resins, polyhydric phenols, for example resorcinol, 2,2-bis-(4-hydroxyphenyl)-propane or phenol-formaldehyde resins;
boron tri~luoride and its complexes with organic compounds, such as BF3-ether complexes and BF3-amine complexes, for example BF3-monoethylamine complex;
acetoacetanilide-BF3 complex; phosphoric acid; triphenylphosphite; polybasic carboxylic acids and their anhydrides, for example phthalic anhydride, ~ -tetrahydrophthalic anhydride, hexahydrophthalic anhydride, 4-methylhexa-hydro~hthalic anhydride, 3,6-endomethylene-~ -tetrahydrophthalic anhydride, methyl-3,6-endomethylene-~ -tetrahydrophthalic anhydride (= methylnadic anhydride), 3,4,5,6,7,7-hexachloro-3,6-endomethylene-~4-tetrahydrophthalic anhydride, succinic anhydride, adipic anhydride, azelaic anhydride, sebacic anhydride, maleic anhydride, dodecenyl-succinic anhydride; pyromellitic dianhydride or mixtures of such anhydrides.
Of these curing agents the polybasic carboxylic acids and their anhydrides are especially suitable.
Curing accelerators can furthermore be employed in the curing reaction; when using polyamides, dicyandiamide, polymeric polysulphides or polycarboxylic acid anhydrides as curing agents, suitable accelerators are, for example, tertiary amines, their salts or quaternary ammonium compounds, for example 2,4,6-tris-(dimethylaminomethyl)-phenol, benzyldimethylamine, 2-ethyl-4-methyl-imidazole, 4-amino-pyridine and triamylammonium phenolate, and also alkali metal alcoholates, such as, for example, sodium hexane-triolate. In the amine curing reaction, monophenols or polyphenols, such as phenol or diomethane, salicylic acid or thiocyanates, can for example be 10~8437 employed as accelerators.
The term "curing" as used here denotes the conversion of the above-mentioned diepoxides into insoluble and infusible, crosslinked products, and in particular, as a rule, with simultaneous shaping to give mouldings, such as castings, pressings or lamlnates and the like, to to give "sheet-like structures", such BS coatings, coverin~s, lac~uer films or the like.
Depending on the choice of the curing agent, the curing reaction can be carried out at room temperature, (18-25C) or at elevated temperature (for example 50-18QC).
The curing can, i~ desired, also be carried out in 2 stages, by first prematurely stopping the curing reaction or carrying out the first stage at only moderately elevated temperature, whereby a still fusible and soluble, curable precondensate (a so-called "B-stage") is obtained from the epoxide component and the curing agent component. Such a precondensate can, for example, be used for the manufacture of "Prepre~s", compression moulding compositions or sintering powders.
The polyepoxides stabilised as above or their mixtures with other polyepoxide compounds and/or curing agents can *urthermore be mixed, in any stage before curing, with customary modifiers, such as extenders, fillers and reinforcing agents, pigments, dyestuffs, organic solvents, plasticisers, flow control agents, aKents for con*erring thixotropy, flame-proofing sub-stances and mould release agents.
As extenders, reinforcing agents, fillers and pigments which can be employed in the curable mixtures according to the invention there may, for example, be mentioned: coal tar, bitumen, textile fibres, glass fibres, asbestos fibres, boron fibres, carbon fibres, cellulose, polyethylene powder and polypropylene powder; quartz powder; mineral silicates, such as mica, asbestos powder and slate powder; kaolin, aluminium oxide trihydrate, chalk powder, gypsum, antimony trioxide, bentones, silica aerogel, lithopone;
baryte, titanium dioxide, carbon black, graphite, oxide pigments, such as iron oxide, or metal powders, such as aluminium powder or iron powder.

Suitable organic solvents for modifying the curable mixtures are, for example, toluene, xylene, n-propanol, butyl acetate, acetone, methyl ethyl ketone, diacetone-alcohol, ethylene glycol monomethyl etber, mono-ethyl ether and monobutyl ether.
As plasticisers for modifying the curable mixtures, dibutyl phthalate, dioctyl phthalate and dinonyl phthalate, tricresyl phosphate, trixylenyl phosphate and also polypropylene glycol can, ~or example, be employed.
As Plow control agents when employing the curable mixtures, especially in surface protection, silicones, cellulose acetobutyrate, poly-vinylbutyral, waxes, stearates and the like twhich in part are al~o used as mould release agents) may, for example, be sdded.
Particularly for use in the lacquer field, the diepoxide compounds can furthermore be partially esterified in a known manner with carboxylic acids such as, in particular, higher unsaturated fatty acids. It is further-more possible to add other curable synthetic resins, for example phenoplasts or aminoplasts, to such lacquer resin formulations.
The curable mixtures according to the invention can be manufactured in the usual manner, with the aid of known mixing equipment (stirrers, kneaders, rolls and the like).
The amine stabilisers are added to the carrier materials in a con-centration of 0,01-10% by weight, based on the carrier material. Preferably, 0,05-4%, and particularly preferentially 0,05-2,5%, are added.
Further possible additives which are added, con~ointly with the amine stabiliser, to the epoxide compounds, are: antistatic agents, lubri-cants, pigments, flameproofing agents, blowing agents, fillers and anti-oxidants, preferably phenolic antioxidants, as well as other light stabi-lisers, such as W-absorbers, as well as phosphites.
Suitable co-stabilisers are e.g. light stabilisers of the benzoat type, such as 3,5-Di-tert.-butyl-4-hydroxy-benzoic acid esters of alkanols or option~lly alkylated phenols, such as of 2,4-di-tert.-butyl-phenol or 2,4,6-tri-tert.-butyl-phenol, or compounds of the formula N~ L6 XLIII

5~ ~,NH-CO-CO-NH ~ ,Llo XLIV

15 ~ OH XLV

COO ~ 14 16 ~ L17 COOL18 XLVI

19 ~ }>----- / COOL18 XLVII

L20~{~ l ~CH3 XLVIII

l =C\clll wherein Ll denotes hydrogen, alkyl, alkenyl or aralkyl, L2 denotes hydrogen, alkyl or chlorine, L3 denotes hydrogen, hydroxyl, carboxyl, alkoxy or alkyl, L~ denotes hydrogen, hydroxyl, alkoxy, alkenyloxy, aralkoxy or alkyl, L5 denotes hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, acylamino, acylaminoalkyl or halogen, L6 denotes hydrogen, alkyl, hydroxyl, alkoxy or acylamino, L7 denotes hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy, halogen, carboxyl, alkoxycarbonyl, alkoxycarbonylalkyl or acylamino, L8 denotes hydrogen, alkyl~ hydroxyl, alkoxy, halogen, acylamino, carboxyl, alkoxycarbonyl, acyloxy, carbamoyl, alkoxysulphonyl, aryloxysulphonyl or ~lphonamido, Lg denotes ~ydrogen, alkyl or halogen, Llo and L12 independently of one another denote hydrogen, alkyl, alkoxy, alkenyloxy, aralkoxy, aryloxy, halogen or alkoxycarbonyl, Lll and L13 independently of one another denote hydrogen or alkyl, L14 and L15 independently of one another denote hydrogen, alkyl, cycloalkyl or aralkyl, L16 denotes hydrogen, alkoxy or aralkoxy, L17 denotes alkyl or aryl, Llô denotes alkyl, cycloalkyl or aralkyl, Llg denotes alkyl or aralkyl, L20 denotes hydrogen, alkyl, alkoxy or halogen, L21 denotes nitrile or alkoxycarbonyl and L22 denotes hydrogen or alkyl.
Preferably Ll denotes hydrogen, alkyl with 1-18 carbon atoms, allyl, methallyl or benzyl, L2 denotes hydrogen, L3 denotes hydrogen or hydroxyl, L~ denotes hydrogen, hydroxyl, alkoxy with 1-20 carbon atoms, allyloxy, methallyloxy or benzyloxy, L5 denotes hydrogen, alkyl with 1-12 carbon atoms, alkenyl with 3-12 carbon atoms, cyclohexyl, aralkyl with 7-11 carbon atoms, phenyl, acylamino with 2-12 carbona toms, acylaminomethyl with 3-13 carbon atoms, chlorine or bromine, L6 denotes hydrogen, methyl, hydroxyl, alkoxy with 1-12 carbon atoms or acylamino with 2-12 carbon atoms, L7 denotes hydrogen, alkyl with 1-12 carbon atoms, aralkyl with 7-11 carbon atoms~
cyclohexyl, phenyl, alkoxycarbonylethyl with ~-15 carbon atoms, alkoxy with 1-12 carbon atoms, chlorine, bromine, carboxyl, alkoxycarbonyl with 2-13 carbon atoms or acyla~ino with 2-12 carbon atoms, L8 denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxy with 1-12 carbon atoms, chlorine, bromine, acylamino with 2-12 carbon atoms, carboxyl, alkoxycarbonyl with 2-13 carbon atoms, acyloxy with 2-12 carbon atoms, carbamoyl with 3-17 carbon atoms, alkoxysulphonyl with 1-12 carbon atoms, phenoxysulphonyl or sulphonamido with 2-16 carbon atoms, Lg denotes hydrogen, methyl, chlorine or bromine, Llo and L12 independently of one snother denote alkyl with l-ô carbon atoms, alkoxy with 1-12 carbon atoms, allyloxy, methallyloxy, phenoxy, benzyloxy, chlorine, bromine or alkoxycarbonyl with 2-13 carbon atoms, Lll and L13 independentl~ of one another denote bydrogen or alkyl with 1-8 carbon atoms, L14 ~nd L15 independently o~ one another denote bydrogel or alkyl with 1-12 carbon atoms, L16 denotes slkoxy with 1-12 carbon atoms, L17 denotes alkyl with 1-3 carbon atoms or phenyl, L18 denotes alkyl with 1-12 carbon atoms, Llg denotes alk~l with 1-12 csrbon atoms, L20 denotes hydrogen, alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms or chlorine, L21 denotes nitrile or alkoxycarbonyl with 2-20 carbon atoms and L22 denotes hydrogen or alkyl with 1-3 csrbon atoms.
Most preferably, Ll denotes hydrogen, alkyl with 1-12 carbon atoms or benzyl, L2 denotes hydrogen, L3 denotes hydrogen or hydroxyl, L4 denotes hydrogen, hydroxyl or alkoxy with 1-12 carbon atoms, L5 denotes hydrogen, alkyl with 1-8 carbon atoms, allyl, methallyl, phenyl, benzyl, ~-phenethyl, -phenylisopropyl, acylaminomethyl with 3-9 carbon atoms or chlorine, L6 denotes hydrogen, methyl, hydroxyl or alkoxy with 1-8 carbon atoms, L7 denotes hydrogen, alkyl with 1-8 carbon atoms, cyclohexyl, phenyl, benzyl, -phenethyl, -phenylisopropyl or chlorine. L8 denotes hydrogen, methyl or chlorine, Lg denotes hydrogen, Llo and L12 independently of one another denote alkyl with 1-4 carbon atoms, alkoxy with 1-8 carbon atoms or chlorine, Lll and L13 independently of one another denote hydrogen or alkyl with 1-4 carbon atoms, L14 denotes hydrogen or alkyl with 1-8 carbon atoms, L15 denotes hydrogen, L16 denotes alkoxy with 1-4 carbon atoms, L17 denotes methyl or phenyl, L18 denotes alkyl with 1-8 carbon atoms, Llg denotes alkyl with 1-4 carbon atoms, L20 denotes hydrogen, L21 denotes alkoxycarbonyl with 2-5 carbon atoms and L22 denotes hydrogen.
The residues have preferably the above mentioned meaning.
Examples of compounds of the formula XLII are:

II. 1. 2,4-Dihydroxy-, 10~8437 II. 2. 2-Hydroxy-4-methoxy-, II. 3. 2-HydrQxy-4-octoxy-II. 4. 2-Hydroxy-4-dodecyloxy-, II. 5. 2-Hydroxy-4-benzyloxy-, II. 6. 2-Hydroxy-4,4'-dimethoxy-, II. 7~ 2,4,4'-trihydroxy-, II. 8. 2,2'-Dihydroxy-4,4'-dimethoxy-, II. 9. 2,2',4,4'-Tetrahydroxy-, II. 10. 2,2'-Dihydroxg-4-methoxy-, II. 11. 2-Hydroxy-2'-carboxy-4-methoxy-, II. 12. 2,2'-Dihydroxy-4-octoxy- snd II. 13. 2,2'-Dihydroxy-4-dodecyloxy-benzophenone.
Examples of compounds o~ the formuls XLIII are:
III. 1. 2-(2'-Hydroxy-5'-methylphenyl)-, III. 2. 2-(2'-Hydroxy-5'-tert.-butylphenyl)-, III. 3. 2-(2'-Hydroxy-5'-tert.-octylphenyl)-, III. 4. 2-(2'-Hydroxy-3'-tert.-butyl-5'-methylphenyl)-, III. 5. 2-(2'-Hydroxy-3'-tert.-butyl-5'-methylphenyl)-5-chloro-III. 6. 2-(2'-Hydroxy-3',5'-di-tert.-butylphenyl)-, III. 7. 2-(2'-Hydroxy-3',5'-di-tert.-butylphenyl)-5-chloro-, III. 8. 2-(2'-Hydroxy-3',5'-di-tert.-amylphenyl)-, III. 9. 2-(2'-Hydroxy-3',5'-di-tert.-amylphenyl)-5-chloro-, III. 10. 2-(2'-Hydroxy-3'-sec.-butyl-5'-tert.-butylphenyl)-, III. 11. 2-(2'-Hydroxy-3'-tert.-butyl-5'-sec.-butylphenyl)-, III. 12. 2-(2',4'-Dihydroxyphenyl)-III. 13. 2-(2'-Hydroxy-4'-methoxyphenyl)-, III. 14. 2-(2'-Hydroxy-4'-octoxyphenyl)-, III. 15. 2-(2'-Hydroxy-3'--phenylethyl-5'-methylphenyl)- Qnd III. 16. 2-(2'-Hydroxy-3'--phenylethyl-5'-methylpheny1)-5-chloro-benztriazole.
Examples of compounds of the rormula XLIV are:
IV. 1. 2-Ethyl-2'-ethoxy-, IV. 2. 2-Ethyl-2'-ethoxy-5'-tert.-butyl-, IV. 3. 2-Ethyl-4-tert.-butyl-2'-ethoxy-5'-tert.-butyl-, IV. 4. 2,2'-Dimethoxy-, IV. 5. 2,2'-Diethoxy-, IV. 6. 4,4'-Dimethoxy-, IV. 7. 4,4'-Diethoxy-, IV. 8. 2,4'-Dimetboxy-, IV. 9. 2,4'-Diethoxy-, IV. 10. 2-Methoxy-2'-ethoxy-, IV. 11. 2-Methoxy-4'-ethoxy-, IV. 12. 2-Ethoxy-4'-methoxy-, IV. 13. 2,2'-Dioctoxy-5,5'-di-tert.-butyl-, IV. 14. 2,2'-Didodecyloxy-5,5'-di-tert.-butyl-, IV. 15. 2-Ethyl-2'-octoxy-, IV. 16. 4,4'-Di-octoxy-, IV. 17. 2-Etbyl-2'-butoxy- and IV. lô. 4-Methyl-4'-methoxy-oxalanilide.
Examples of compounds of the formula XLV are:
V. 1. Salicylic acid phenyl ester.
V. 2. Salicylic acid 4-tert.-butylphenyl ester.
V. 3. Salicylic acid 4-tert.-octylphenyl ester.
Examples o~ compounds of the formula XLVI are:
VI. 1. -Cyano-~-methyl-4-methoxycinnamic acid methyl ester.
VI. 2. -Cyano-~-methyl-4-methoxycinnamic acid butyl ester.
VI. 3. -Cyano-~-phenyl-cinnamic acid ethyl ester.
VI. 4. -Cyano-~-phenyl~cinnamic acid isooctyl ester.
Examples of compounds of the formula XLVII are:
VII. 1. 4-Methoxy-benzylidenemalonic acid dimethyl ester.
VII. 2. 4-Methoxy-benzylidenemalonic acid diethyl ester.
VII. 3. 4-Butoxy-benzylidenemalonic acid dimethyl ester.
Examples of compounds of the formula XLVIII are:

VIII. 1. N-(~-Cyano-~-carbomethoxyYinyl)-2-methylindoline.

VIII. 2. N~ Cyano-~-carbooctoxyvinyl)-2-methylindoline.
VIII. 3. N-(~-Cyano-~-carbethoxyvinyl)-2-methylindoline.
VIII. 4. N-(~-Cyano-~-carboisooctoxyvinyl)-2-methylindoline.
The manufacture cf most of the above compounds is known from the literature.
Compounds of the formula I can be ~anufactured according to F.
Asinger, Nbnatshe~te ~, 1436-1451 (1968), German Offenlegungsschrirten 2,040,975, 2,110,298, 2,128,757, 2,146,692 and 2,203,447, United States Patents 3,513,170, 3,639,409, 3,640,g28 and 3,663,558, British Patents 1,196,958, 1,202,299 and 1,262,234, Belgian Patents 778,381 and 778,676 and Jap~nese Patent 600,043.
Further compounds of the formula I can be manufactured as follows:
Compounds of the general formula XV by condensation of the cor-responding 4-aminopiperidines with aldehydes or ketones, according to known methods;
compounds of the general ~ormuls XVI by condensation of the cor-responding 4-piperidinones with cyanoacetic acid or its esters by the Knoevenagel method, decarboxylation, catalytic hydrogenation of the unsaturat-ed nitrile and alkylation or acylation of the resulting primary amine;
compounds of the general formula VI by oximation of the correspond-ing 4-piperidinones and optionally subsequent alkylation or acylation accord-ing to known methods, compounds of the general formulae XII (B) and XIII (A) by condensa-tion of the corresponding 4-piperidinones with phenols in the presence of acid catalysts to give compounds of the formula A and subsequent catalytic hydrogenation to give compounds of the formula B;
compounds of the general formulae XXIII(C) and XXIV(D) by condensa-tion of the corresponding aminocyanohydrins according to R. Sudo, Bull. Chem.
Soc. Japan 36, 34 (1963), subsequent hydrolysis according to E.F.J. Duynstee, Rec. 87, 945 (1968) and optional alkylation to give compounds of the formula C which can in turn be reduced with lithium aluminium hydride to give com-pounds of the formula D.

Compounds of formulae XLII-XLVIII can be manufactured according to United States Patents 3,006,959 and 3,043,797, Swiss Patent 355,947, British Patent 1,177,095, French Patent 1,318,102, German Auslegeschrift 1,087,902 and Netherlands Patent Application 67/08,332.
Example 1 50 parts Or a bisphenol A-epoxide resin which is liquid at room temperature, with an epoxide equivalent weight o~ 175-200 and which was man-u~actured by condensation of eplchlorohydrin with bis-(p-hydroxyphenyl)-diphenylmethane in the presence of alkali (~ormula below, where n has a velue of about 0,2) CH2 ~ H-CH2 ~ ~ -CH2- CH-CH~ 0 ~ 0-CH2-CH ~ 2 and 17 parts of bis-(4-amino-3-methylcyclohexyl)-methane were thoroughly mixed, after which 33 parts of titanium dioxide were added, o,66 parts of one of the stabili~ers of the following table were dissolved in 6,6 parts of Xylene and stirred into the mixture.
The compositions were then spread onto 10x15 cm steel plates and cured in an oven during 5 hours at 40 C and subsequently during 2 weeks at 20C.
The thus coated plates were then weathered artificially in a Weatherometer and the chalking of the surface caused by weathering is record-ed periodically. A coating with no incorporated stabilizer is used for com-parison purposes. For the rating of chalking an empirical scale is used in which the meanings of the figures are as folloNs:

O No chaIking 1 Trace chalking 2 Moderate chalking 3 Very severe chalking 10~8437 Chalking ratings aMer hours of weathering Stabilizer 300 400 500 8so looo 1250 None 0 1-2 2 2 2-3 3 _ _ 0 0 0 1-2 1-2 2 Stabllizer A: N-Cyclohexyl-(2,2,6,6-tetramethylpiperidinyl-4)-acetamide Stabilizer B: N-Cyclohexyl-(1,2,2,6,6-pentamethylpiperidinyl-4)-acetamide.
Example 2 54 parts of a bisphenol A-epoxide resin which is solid at room temperature, with an epoxide equivalent weight of 870-1020 and which was ma~ufactured by condensation of epichlorohydrin with bis-(p-hydroxyphenyl)-diphenylmethane in the presence of alkali (as a Xylene-Butyl acetate solu-tion, formula below, where n has a value of about 6) 10 CH2 ~H-CH2~o4~o-CH2-CH-cH~-o~--CH C/ \

were pigmented by adding 35 parts of titanium dioxide, after which 16 parts of Hexahydrophthalic anhydride were added, o.66 parts of one of the stabi-lizers of the following table were dissolved in the above mixture.
The compositions were then brushed onto lOx15 cm steel plates and cured in an oven during one hour at 120 and subsequently during 15 Minutes at 170C.

The thus coated plates were then weathered artificially in a ~eatherometer and the chalking of the surface caused by weathering is record-ed periodically. A coating with no incorporated stabilizer is used for com-parison purposes. For the rating of chalking an empirical scale is used in which the meanings of the figures are as follows:

O No chalking 1 Trace chalking 2 Moderate chalking 3 Very severe chalking.

Chalking ratings a~ter hours o~ arti~icial Stabilizer weatherlng None O 0 0 0 O1 1-2 22-3 . _ _ _ . C__ O O O O O O O O 1 .

Stabilizer A: N-Cyclohexy1-(2,2,6,6-tetramethylpiperidinyl-4)-acetamide Stabilizer B: N-Cyclohexyl-(1,2,2,6,6-pentamethylpiperidinyl-4)-acetamide Stabilizer C: 3-n-Octyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4,5]decan-2,4-dion Stabilizer D: l-Chloro-3,5-Bis-(2,2,6,6-tetramethylpiperidinylamino-4)-S-Triazine.
At the same time, the plates were exposed to natural weathering, 45 South, in Manchester, England, and the degree of chalking of the sur~ace recorded monthly. For the rating, the same empirical scale is used, Chalking ratings after Stabilizer months of natural weathering None 00 1 2 2 3 __ _ _ Example 3 50 parts of the diglycidyl ether of 2.2-bis-(4-hydroxycyclohexyl)-propane having formula:

0\ CH3 0 CH2 CH - CH2 - 0 ~ C ~ 0 - CH2 CH CH2 were pigmented by adding 42 parts of titanium dioxide after which 35 parts of Hexahydrophthalic anhydride were sdded, 0.ô5 parts of one of the stabilizers of the following table were dissolved in 8.5 parts of a Xylene-Butyl acetate mixture and added. The compositions were then spread onto 10 x 15 cm steel plates and cured in an oven during one hour at 120C and subsequently during 15 minutes st 170C.
The thus coated plates were then weathered artificially ln a weatherometer and the chalking of the surface caused by weathering is record-ed periodically. Coating with no incorporated stabilizer is used for com-parison purposes. For the rating of chalking an empirical scale is used in which the meanings of the ff gures are as follows:
0 No chalking 1 Trace chalking 2 Moderate chalking 3 Very severe chalking Chalking ratings after hours of articial weathering Stabilizer 300 400 500 850 1000 1250 1500 1750 2000 .. _ . ... _ None 0 0 0 1 1 1-2 2-3 3 3 . .__ . .

Stabilizer A: N-Cyclohexyl-(2,2,6,6-tetramethrlpiperidinyl-4) acetamide Stabillzer B: N-Cyclohexyl-(1,2,2,6,6-pentamethylpiperidinyl-4) acetamide At the same time, the plates were exposed to natural weathering.

45 South, in Manchester, England, and the degree of chalking of the surface recorded monthly. For the rating, the same empirical scale i8 used.

. Chalking ratings after months of natural weathering Stabilizer 2 4 6 8 10 12 ..
None 0 0 0 1 1 2 _ . ._ .

.__ . .. .
Example 4 35 parts o~ a bisphenol A-epoxide resin which is solid at room temperature, with an epoxide equivalent weight of 1660-2000 and which was manufactured by condensation of epichlorohydrin with Bis-(p-hydroxyphenyl)-diphenylmethane in the presence of alkali (as a Xylene-Butyl acetate solu-tion, formula belo~, where n has a value of about 11) CH2--CH_cH2~o~0-CH2~CH~CH2~

were pigmented by adding 40 parts of titanium dioxide after which 15 parts o~ a butylated melamine-~ormaldehyde resin were added. 0.5 parts o~ one of the stabilizers o~ the following table ~ere dissolved in 5 parts of XYlene-Butylacetate mixture and added.
~ he compositions were then brushed onto lO x 15 cm steel plates and cured in an oven during one hour at 180C.
The thus coated plates were then exposed to natural weatherine, South, in Manchester, England, and the degree o~ chaIking o~ the surface recorded monthly. A coating with no incorporated stabilizer is used for comparison purposes. For the rating o~ chalking an empirical scale is used, in which the meanin~s o~ the figures are as follows:
O no chalking 1 trace chalking 2 moderate chaIking 3 very severe chaIking Chalking ratings a~ter months o~ natural weathering Stabilizer 2 4 6 8 lO
.. . ,,_ None 0 l l l 2 .._ A 0 0 0 l .. _ .. _ Stabilizer A: N-Cyclohexyl-(2,2,6,6-tetramethylpiperidinyl-4) acetamide Stabilizer B: N-Cyclohexyl-(1,2,2,6,6-pentamethylpiperidinyl~4) acetamide

Claims (9)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. Epoxy resins stabilised by at least one sterically hindered cyclic amine of the formula I

(I) and salts thereof in which q is 1 or 2, X represents an organic grouping which complements the nitrogen-containing ring to give a 5-membered, 6-membered or 7-membered ring, R1 and R2 represent methyl or together represent -(CH2)5-, R3 represents methyl, R4 represents alkyl with 1-5 carbon atoms or together with R3 represents the radicals -(CH2)4-, -(CH2)5-, -CH2-C(CH3)2-NH-C(CH3)2-CH2- or -CH2-C(CH3)2-N(O?)-C(CH3)2-CH2- and, if q is 1, Y denotes hydrogen, -O?, hydroxyl, alkyl, hydroxyalkyl, acyloxyalkyl, alkenyl, alkynyl, aralkyl or acyl or, if q is 2, Y denotes alkylene, alkenylene, alkynylene, cycloalkylene or aralkylene.

2. Epoxy resins as claimed in claim 1, in which the sterically hindered amines of formula I correspond to the following formulae:

II

III

IV

V

VI

VII

VIII

IX

X

XI

XII

XIII

XIV

XV

and XVI

in which formulae Y1 represents hydrogen, -O?, hydroxyl, alkyl, hydroxyalkyl, acyloxyalkyl, alkenyl, alkinyl, aralkyl or acyl, R1 and R2 represent methyl or together represent -(CH2)5-, R3 represents methyl, R4 represents alkyl with 1-5 carbon atoms or together with R3 represents the radicals -(CH2)4-, -(CH2)5-, -CH2-C(CH3)2-NH-C(CH3)2-CH2- or -CH2-C(CH3)2-N(O?)-C(CH3)2-CH2-, s represents 1, 2 or 3, p represents 1 to 3, n represents 1 to 4, R5 represents hydrogen, a saturated or unsaturated aliphatic, cycloaliphatic or araliphatic radical, an aromatic radical, a monovalent to tetravalent acyl radical which is derived from an aliphatic, cycloaliphatic, araliphatic, aromatic or hetero-cyclic monobasic or polybasic carboxylic acid, from a carbonic acid or from a monobasic or polybasic phosphoric, sulphuric, boric or silicic acid, an s-triazinyl radical or a group of the formula XVII

R6 represents hydrogen, a saturated or unsaturated aliphatic, cycloaliphatic or araliphatic radical, an aromatic radical, or a monacyl radical derived from a monobasic carboxylic acid or carbonic acid, A represents oxygen or =N-R24, wherein R24 is hydrogen, alkyl, hydroxyalkyl, acyloxyalkyl, alkenyl, alkinyl or aralkyl, B represents , , alkylidene, alkylidene or aralkylidene, D represents oxygen, sulphur or NH, R7 represents hydrogen, alkyl, aralkyl or a monoacyl, diacyl or triacyl radical derived from a mono-basic to tribasic carboxylic acid, or a carbonic acid radical, R8 and R9 independently of one another represent alkoxycarbonyl, acyl, nitrile or phenyl, R10 represents a saturated or unsaturated aliphatic, cycloaliphatic or araliphatic radical, an aromatic radical or a group of the formula XVII, E represents oxygen, sulphur or , wherein R25 is hydrogen, alkyl, cyclo-alkyl or aralkyl, R11 represents hydrogen or alkyl, R12 represents hydrogen, alkyl, cycloalkyl or aralkyl, R13 represents hydrogen, a saturated or unsatur-ated aliphatic, cycloaliphatic or araliphatic radical, an aromatic radical, a monovalent or divalent acyl radical derived from an aliphatic, cycloalipha-tic, araliphatic, aromatic or heterocyclic monobasic or dibasic carboxylic acid, from a carbonic acid or from a monobasic or polybasic phosphoric acid or sulphuric acid, an s-triazinyl radical, a radical of the formula XVII or, together with R12, an alkylene radical which can be interrupted by hetero-atoms, R14 and R15 independently of one another represents alkyl, cycloalkyl or ar-alkyl or together represent alkylene, R16 represents hydrogen or acyl, with the ring Z representing a benzene or cyclohexane ring which is unsubstituted or substituted by 1-3 alkyl, cycloalkyl or aralkyl groups, R17 and R18 repre-sent the same alkyl group or together represent 1,2-ethylene, 1,3-propylene, 1,2-phenylene or a group of the formula XVIII

R19 represents hydrogen, alkyl, alkenyl, aralkyl, aryl or substituted aryl and R20 represents alkyl, alkenyl, aralkyl, aryl, or a heterocyclic radical, or R19 and R20 together represent cycloalkylidene, or correspond to one of the following formulae:

XIX

XX

XXI

XXII

XXIII

XXIV

XXV

XXVI

XXVII

in which formulae Y2 denotes hydrogen, -O? or methyl, s, p, R1, R2, R3 and R4 denote what has been mentioned above, R21 denotes a monovalent or divalent acyl radical derived from a monobasic or dibasic carboxylic acid or carbonic acid, R22 denotes hydrogen, alkyl, alkoxycarbonylalkyl, aralkyl, alkylene, aralkylene or arenetriyl-tris-alkyl, R23 denotes the same as R22 or denotes a monoacyl or diacyl radical or -(CH2)1-12-COOMe, Me being hydrogen or MeZ l/z and Me being a dialkyl tin residue or a metal residue and z being 1-4 and the valence of that residue Me, R26 denotes alkyl, cycloalkyl, aralkyl, aryl, aryl-amino, alkylene, cycloalkylene or arylene, R27 denotes alkyl and R28 denotes hydrogen or alkyl with 1-5 carbon atoms, or correspond to the formula XXIX

wherein R1, R2, R3 and R4 have the abovementioned meaning, Y3 represents hydrogen or methyl and R29 represents alkyl, cycloalkyl or aralkyl, Ya is for w being 1 alkyl, hydroxyalkyl, acyloxyalkyl, alkenyl, alkinyl or aralkyl, Ya is for w being 2 alkylene, interrupted alkylene, alkenylene, alkinylene or bis-alkylene arene, Ya is for w being 3 T[OOC-(CH2)X-]3 with x being 1-4 and T being a trivalent hydrocarbon residue, or Ya is for w being 4 Q[OOC-(CH2)x-]4 with x being 1-4 snd Q being a tetravalent hydrocarbon residue, or in a compound XX Ya is -CO-Xxx-Rxx, Xxx being O or NH and Rxx being a hydro-carbyl residue having from 1-20 C-atoms and w is 1 or 2 or corresponds to the formula XXX

as well as salts thereof, wherein Yxxx is O?, hydrogen or alkyl with 1-4 carbon atoms, Rxxx is a hydrocarbyl residue with 1-20 carbon atoms and Z is S or O, or corresponds to the formula XXXI

wherein Yxxxi is hydrogen, hydroxy, O?, alkyl, alkenyl, alkinyl or alkoxyalkyl, Rb is alkyl and Rc is alkyl or phenethyl, or corresponds to the formula XXXIII

Rxxxiii and Rxxxiii, being same or different and each hydrogen, alkyl, alkenyl, alkinyl, aralkyl, hydroxyalkyl, alkoxyalkyl, aliphatic or aromatic acyloxyalkyl, cyanoalkyl, halogenoalkyl, epoxyalkyl, alkoxycarbonylalkyl, aliphatic acyl, alkoxycarbonyl or aralkoxycarbonyl, or corresponds to the formula XXXIV

Rxxx being same as Rxxx and Rm, Rn, Ro, Rp and Rq being same or different and hydrogen or alkyl.

3. Epoxy resins as claimed in claim 2, in which in the formulae given for sterically hindered cyclic amines and in the formulae II-VIII, Y1 denotes hydrogen, -O' or methyl, R1, R2, R3 and R4 denote methyl, s denotes l, p denotes l, n denotes l or 2, R5 denotes hydrogen, or an acyl group which is derived from an aliphatic carboxylic acid with 1-18 carbon atoms, from acrylic acid or methacrylic acid, from benzoic acid or from an alkyl-benzoic acid with 8-11 carbon atoms, from salicylic acid, from an aliphatic dicarboxylic acid with 4-14 carbon atoms, from terephthalic acid, from isophthalic acid or from a carbamic or thiocarbamic acid which is substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, R6 denotes alkyl with 1-12 carbon atoms, allyl, benzyl, cyclo-hexyl, glycidyl, hydroxyethyl, alkoxyalkyl with 3-10 carbon atoms, alkoxycarbonylalkyl with 3-14 carbon atoms, hexamethylene or 3-oxapentamethylene, A denotes or , wherein R24 is hydrogen, methyl, ethyl or benzyl, B denotes , D
denotes oxygen, R7 denotes hydrogen, methyl, benzyl, benzoyl or phenylcarbamoyl, R8 denotes nitrile, R9 denotes ethoxy-carbonyl, phenyl or benzoyl, R10 denotes alkyl with 6-8 car-bon atoms, cyclohexyl, benzyl, alkylene with 4-12 carbon atoms, xylylene, phenylene or 2,2,6,6-tetramethyl-piperidinyl-4, E denotes oxygen or , R11 denotes hydrogen, R12 denotes hydrogen or methyl, R13 hydrogen or an acyl group which is de-rived from an aliphatic carboxylic acid with 1-18 carbon atoms, from acrylic or methacrylic acid, from a benzoic acid with 7-10 carbon atoms, from salicylic acid or from a carbamic or thio-carbamic acid which is substituted at the nitrogen by alkyl with 1-12 carbon atoms, benzyl or phenyl, R14 and R15 denote alkyl with 4-8 carbon atoms, benzyl or chloroethyl, R16 denotes hydrogen or the radical of an acyl group which is derived from an aliphatic carboxylic acid with 2-12 carbon atoms, from benzoic acid or from a N-alkyl-carbamic acid with 2-8 carbon atoms, with the ring Z representing a benzene ring which is substituted further by 1-2 methyl, isopropyl or tert.-butyl groups, R17 and R18 denote methyl, ethylene, 1,3-propylene or a group of the formula XXXV, R19 denotes hydrogen, R20 denotes alkyl with 1-8 carbon atoms, benzyl, phenyl, alkoxyphenyl with 7-10 carbon atoms, or together with R19, -(CH2)5-, R21 denotes an acyl group which is derived from an aliphatic monocarboxylic acid with 3-18 carbon atoms of which the chain can be interrupted by sulphur atoms, from phenylacetic acid, from benzoic acid or from salicylic acid, R22 denotes hydrogen, alkyl with 6-18 carbon atoms or benzyl, R23 denotes the same as R22 or an acyl group which is derived from an aliphatic carboxylic acid with 3-18 carbon atoms, from benzoic acid or from a carbamic acid which is substituted at the nitrogen by alkyl with 1-12 carbon atoms or phenyl, R24 denotes hydrogen, methyl, ethyl or benzyl, R26 denotes alkyl with 4-18 carbon atoms, benzyl or phenyl, R27 denotes alkyl with 1-4 carbon atoms, R28 denotes hydrogen, R29 denotes alkyl with 4-18 carbon atoms or benzyl.

4. Epoxy resins as claimed in claim 1, containing sterically hindered cyclic amines of the formula XXXVII

in which Y1 denotes hydrogen, -O? or methyl, R6 denotes alkyl with 1-12 carbon atoms, allyl, benzyl, cyclohexyl, glycidyl, hydroxyethyl, alkoxyalkyl with 3-10 carbon atoms, alkoxy-carbonylalkyl with 3-14 carbon atoms, hexamethylene or 3-oxa-pentamethylene, R24 denotes hydrogen, methyl, ethyl or benzyl, and n denotes 1 or 2, or of the formula XXXVIII

in which Y1 denotes hydrogen, -O? or methyl, R5 denotes an acyl group which is derived from an aliphatic carboxylic acid with 1-18 carbon atoms, from acrylic acid or methacrylic acid, from a benzoic acid with 7-11 carbon atoms, from salicylic acid, from an aliphatic dicarboxylic acid with 6-14 carbon atoms, from terephthalic acid,from isophthalic acid, from .beta.-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionic acid or from 3,5-di-tert.-butyl-4-hydroxy-benzoic acid and n denotes 1 or 2. R5 also denotes an s-triazinyl radical which has a chlorine substituent and n is 2.

5. Epoxy resins as claimed in claim 4, wherein R5 also denotes an s-triazinyl radical which has a chlorine substituent and n is 2.

6. Epoxy resins as claimed in claim 1, derived from epoxy compounds containing more than one epoxide group.

7, Epoxy resins as claimed in claim 1, wherein the amine stabilisers are added to the carrier materials in a concentration of 0,01-10% by weight, based on the carrier material.

8. Epoxy resins as claimed in claim 1, wherein the amine stabilisers are added to the carrier materials in concentrations of 0,05-2,5%, based on the carrier material.

9. Epoxy resins as claimed in claim 1, containing as further additives antistatic agents, lubricants, pigments, flameproofing agents, blowing agents, fillers and antioxidants, phenolic antioxidants, UV-absorbers and/or phosphites.