CA2057581A1 - Piperidine compounds containing silane groups for use as stabilisers for organic materials - Google Patents

Abstract

Novel piperidine compound containing silane groups for use as stabilisers for organic materials Abstract of the Disclosure The present invention relates to novel piperidine compounds of the formula (I) (I) in which A is e.g. a group of the formula (I) where R4 is e.g. hydrogen or methyl, X3 is e.eg. -O- or -NH- and R5' is e.g. ethylene, propylene or deca?ethylene, R1 is e.g. methyl, methoxy, ethoxy or OH, R2 and R3 are e.g.
methyl, m + n is e.g. a number from 1 to 40, n varies e.g. from zero to 50 % of the sum m + n, X1 is e.g. as defined for R1 or is a group and X2 is e.g. hydrogen, methyl, ethyl, a group (CH3)3Si- or a group

Description

~ ~v3 A- 1 X4 ~7/A CHM 57 Novel r)i~)eridine eoml oun_l~s co~ lini~ silane ~r )ul~s ror use as ~stabilisens for or~anie materials The present invention rela~e~s to novel pip(,l idille eompollnds conlaining silalle groups, to their use as ~stabilisers ror orgarlic malerial.s, in l-al ticlllar ~synthetie polym~ls, again~st light, heat and oxidation, and to organic materi.ll~s tl-us stabilised.

TllC U.SC ol 2,2,6,6-tCtrallletllylpir)('li(lillC dCliV~l~iVCS COll~lillillg ~SilallC ~'r()llllS, SIICIl IS
lhosc rcl~orlc(l in U~'; I'a~( lll.s Nos. 4 177 I X() all(l 4 X5() 75'), I~,P L,ai(l Open l'rints No~s. 162 524, I X2 415, 244 ()26, 263 S(~l, 343 717 alld 35X 2()() and DD l~ltents Nos. 234 6X2.Ind 234 6X3, a~s sLIbilisers ror synthelic polymers is known.

The l~re~sent invention rel~ltes to novel compolln(l~s Or lllc genelal lollllllla (1) t ~ t (I) in whicll A is one ol llle Inolll)s ol lll( lolnnll(le (111l) (lld) l13~ 0 ~ ~ o 1~ N ~ X:~ ( t '~ N~,~- N--( '--()--1~7--" (,k~ , "~ 6 (11~1) (111~) ~ ~ ~f ~

H3C CIS3 0113C CH3 0 ~/R10 )L~ ~ R9-->~ ~ . ~ _ k~ ~ 8R4 ~ Nk~ N \~
113C C~13 0tl3C C}13 0 (llc)(lId) in which R4 is hydrogcn, C1-C8alkyl, 0 ,011, NO, Cl12CN, Cl-C1xalkoxy, Cs-CI2cyclo-a1koxy, C3-Cfialkcnyl, C7-C9phenyl;l1kyl which is unsl1bstit-1te(1 or mono-, di- or lri-substitutcd on thc p!lcny1 by (`1-C"a1ky1; or C1-C8acy1, X3 iS -O- or >N-Rl2 where Rl2 is hy(lrogen, Cl-Clxa1ky1, Cs-C12cyc10a1ky1 which is uns11bstitllted or mono-, di- or tri-xl1bstitl1tc(1 hy C1-C,~;11ky1; C7-(~ )hcnyh11kyl which is unsl1bstitl1tc(1 or mono-, di- or ~ri-sul-s~i~u~c(l 0n ~l1c ~ lly1 by C`1 -C,1.11kyl; or ~c1r.111y(llofl1r1l1ry1~ C2-C,1.11ky1 substitl1te(1 h1 lhc 2-, ~- or 4-posilio11 by C1-C'~;11koxy, by (1i--(('1-C,~;11ky1)-.11ni1lo or by a group of the fonllula (111) A

X,~ N- (1ll) \J
whcrc X~ is .1 (lirc~l boll(l, -O-, -('1 l2-, -('I 12CI 12- or l 13C-N<, or R12 is a gro11p of the f'ol~ ll;l (IV), 11s(~ s Nk~ ( I V ) s~ ( I1s wi~ 1)ov~,01 1~12i~011~or ~ gl0111)!.0rI~ rO,"~ ;l. (v;l)-(v(l) I11( (IIS I1S( (I1, Y \ Y-\ ~\
Nk~--XS--(( 112):3 , 1~,~--N~N ~N--(C112)2 13(. ~1ls 113( ( 113 (V;l) (V~) 3 -- ~ O
1-13C Cl13 ~13C C113 o Y \ / \ )~\ ~
R4--N~ N ~ Cl 12-- R4--Nk~ N~rl (Vc) (Vd) where R4 is as defined above, X5 iS -O- or >N-CTT3 and X6 is -CTI2CH2-, -CO-, -COCO-or -COCI 12CO-, or X3 iS a I ,4-piper1~inediyl group7 p is 1, 2 or 3 an(l, when p is I, Rs is C2-CI8alkanediyl and, when p is 2, Rs i~s C2-C2()l1kaneLriyl~ Cs-C7cycloalkane~riyl or C7-C9bicycloalkanetriyl or a group - C~l -X7-RI3- where X7 is -O- or >N-RI4 with Rl4 -(C~-12)~, being Cl-Cxlcyl or (C l-Cx11k()xy)c.~ yl~ s Cl-CI2l1kllle(1iyl ,~ 1 is () or 1, and, when p i.s ~3, Rs i~s C'3-C(,I1kane~elllyl~ R~; is 1S del`ine(l ahOve l`or Rl2, R7 hs C2-CI2llkane-diyl, Rx is hydrogen or melhyl, R(~ i~s 1 direcl hond, Cl-CIxalkanediyl or 1 group -X7-RI3-wilh X7 and Rl3 as defined above, Rl(~ is hydrogerl or methyl and Rll is -CH2- or -CH2CH2-, Rl is Cl-C8alkyl, phenyl, Cl-C8alkoxy or OH, R2 and R3 which are iclelltical or different are Cl-C8alkyl or phenyl, or R2 is 11S() hydro~en~ n is 1 number lrom I to 100, n varies from ~ero to ~)() % ol the sum ol' nl + n, Xl i~s 1S derine~ f()r Rl or is 1 group (Rls)3Si()- wilh Rl~; being C~-C8alkyl or phenyl, X2 is hydrogell, Cl-C8alkyl, a group Rl (l~l5)3Si- or when 1~1 1n~1 Xl 1re Cl-Cxl1kyl or phenyl, X2 is 1(~ i()tl111y 1 ~r()Ufl -~;;i-XI, an(l, when m -~ n i~s 1 llUlllhCI' 1'1'0111 ~ (), X I illld X~ lO~!,CIIlCmlllSO 1'01'111 11 dil'CCI b011~1.

Tllc l;()lllll()un~l~s ol Illc lolllllll.l (1) C()1111ill ~SII'llCllll'1l llllilS ()I Illc ll)l'llllll(l (1(l) ()1' 1 c()lllbill1ti()11 ()I lllC l()rMUI1C (11) 111~
(~ t (11) (Ih) When lhc collll~ound~s of lhe p r~selll invelllioll al'C pOIynlcl s or cop()lylller~s, elch of lhe s A, 1~ 2 .u~ llc ill(liVidllll rcclllri~ slrllclur11 lllliLs (11) 1rld (Ib) of the ~ ~ 3 fonnula (I) can be identical or different.

When the compoullds of the present invention iare copolymers, the sin~le structural units (la) and (Ib) of the fonnula (I) can be distribllted lherein at random or in blocks.

Examples of alkyl having not more than 1 X carbon atoms are methyl, ethyl, propyl, isopropyl, blltyl, 2-butyl, isobutyl, t-b~ltyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, t-octyl, nonyl, decyl, Imdecyl, dodecyl, tridecyl, tetr.ldecyl, hexadecyl and octadecyl.

Examples of C2-C"alkyl sllbstit~lte(l by Cl-C8alkoxy are 2-me~hoxyetllyl, 2-ethoxyethyl, 3 metl1oxyplopyl, 3-elh(lxyplol)yl~ 3-b;ltoxyprorlyl, 3-oetoxypropyl alld 4-metlloxyb~ltyl.
~-Mcthoxypropyl all(l 3-c(llo~yyplopyl ;Irc prcl'crlc(l.

Exarnples of C2-C4alkyl s~lbslit~lte(J by di- (Cl-C4alkyl)-amillo, preferably by dimethyl-amino or dielhylamino, are 2-dimelhyl.lminoethyl, 2-diethylaminoethy!, 3-dimethylamino-propyl, 3-diethylaminopropyl, 3-dibutyl.lmillopropyl and 4-(liclhyl;llllitlob~llyl.

Examples of C2-C,~alkyl substil-lted by a ~roup of fomlula (111) are 2-pyrrolidinoethyl, 2-morpholinoetllyl, 3-morpllolilloplol?yl~ 2-piperidinoethyl, 3-piperidinopropyl and 2-(4-mclhylpipcra;~.illo)-elhyl. 3-Morl)holillol)rol)yl is prcfcrlcd.

Examples of alk(lxy conl;lil~ not nlolc tll;lll I X c;lrl~On atolllS ;IIC nlcllloxy~ Clll()xy~
propoxy, isopropoxy~ h~lloxy, iSObn~OXy, pcn(Oxy, isopcllloxy, hcxoxy, llcploxy, octoxy, decyloxy, (lodeeyloxy, le~r;ldecyloxy, hex;l(lecyloxy all(J oc~a(lecyloxy.

I~epresel1l,llive examl-l-s ol Cs-(`l2cycloalkyl l~("ln(l Rl2, wlliell is uns~lbsli~ e(l or 1110110-, (li- or lri-s~lbstitlltc(l l-y C~ ;llkyl, ;Irc cyclopclltyl, mctllylcyclopentyl, dilllclllylcyclopelllyl, cyclohcxyl, nlclllylcyclollexyl~ (limelllylcyclohcxyl~ trimctllyl-cyclohcxyl, t-b~ltylcyclollexyl, cyclooctyl, cyclo(lccyl ;IIld cyclo(lo(lccyl; ulls-lbstitute(l or Cl-C4alkyl-s~lbstilulc(l cyclollcxyl is pleferrc(l.

Examples of Cs-Cl2cycloalkoxy are cyeloi~entoxy, cyclohcxoxy, cycloheptoxy, cyclo-octoxy, cyclo(lccyloxy ;m(J cyclo-lo(lecyloxy. Cyclopclltoxy ;IIld cyclollcxoxy .Irc prercrrc(l.

- s -Examples of C3-C6alkenyl are allyl, 2-methylallyl, 2-butenyl and 2-hexenyl. Allyl is preferred.

Examples of C7-C9phenylalkyl which is unsubstituted or mono-, di- or tri-substituted on the phenyl by Cl-C4alkyl are benzyl, methylbenzyl, dimethylbcnzyl, trimethylbenzyl, t-butylbcnzyl and 2-phenylcthyl. Bcnzyl is preferred.

Examples of Cl-C8acyl are formyl, acetyl, propionyl, butyryl, pentanoyl, hcxanoyl, hcptanoyl, octanoyl, bcnzoyl, acryloyl and crolonyl. Cl-C8alkanoyl, C3-C8alkenoyl and benzoyl arc prcfcrred. Acetyl is espccially prefcrred.

Rcllrcsent;ltive cxalllplcs Or C2-C~x;llk;lllc(liyl 1~5, whcll p is 1, arc cthylcl1c, ctllylidcne, propylcl1e, propyli(lcnc, trimctl1ylcnc, mcthyltrirllethylcllc, tctrametllylene, penta-rllctllylene, hcxylene, decamethylcnc or ~roups of the formula Cl-13(CI12)7-C~I-(CH2)8- or Cl-13(CI-12)X-Cl ~-I-(C~I2)7- .

Rcprcsclllativc cxarllplcs of C2-Cl2alk;lllc(1iyl R7 arc cthylcrle, trimctllylcllc, methyltri-mcthylcnc, tctrarnctllylcllc, pcrlt.lmcthylcne and un(lec.lmcthylcne.

Rcprcscllt,ltivc exalllplcs of Cl-Clxalk.lllc(liyl R9 arc mctllylcllc, cthylcllc, trilllctllylcllc or .1 lincar or brancllc(l C,~-C~xalkilllc(liyl, for CX;IIIll~lC l~Utylcllc~ pelllylell(~ hcxylcllc, o~:tyl~llc, (I(~cyl~ , (Io(l~yl(l~ cy~ x;l~ yl~ ;1ll(1 o~ ( ylcll~.

C3-CI2Alkallc(liyl Rl-~ is, I'or cxamplc, trimctllylcllc, nlctllyllr pclltalllctllylcllc, hcx.llllclllylcne or lul(lec.llllclllylcllc.

I~cplciiclll;llivc ex;lllllllcs of C2-C2(~;l1k;lllcll iyl l~5, whcll p is 2, alc ctll,lllctriyl, prop;lllctriyl~ l~ul;lllelliyl or a ~rollp -(`I l-Rj,- wh(rc R;, is lincar or br;lllcllcd (~1 1 C3-CIxalk;lllc(liyl, for cx;llllplc trimclllylcllc, blllylcllc, pclllylcl1e, hcxylcl1c, octylene, dccylcnc, dodccylcllc, tclr;ldccylcrlc, hcx;ldccylcnc or ocladccylcne.

Rcplcsclll.llivc cx;llllplcs ol Cs-C7cyclo;l1kllllclriyl or C7-C~)bicycloalk.llletriyl Rs are thc ~I'Olll)S

~ ~ cj~

Rel-re.sen~ative examT)le~s Or C3-C(,cllkanele~r~lyl Rs are ~ropanetetrayl, butalleletrayl and -cntanctctrayl.

Representiltive example.s Or (Cl-Cxalk()xy)carl-ollyl are melhoxycal bonyl, ellloxyearbonyl, l~ropoxycarhollyl, i.sopropoxyc.lrh()nyl, huloxycall)otlyl1 i~ol-ul,()xycalb()llyl, pcnloxy-carbonyl, isopcntoxycarb(?llyl, hcxoxyc~nhol~yl, hcploxyc~llhollyl all(l octoxycarbonyl.

1`he prererred (Ierinition~s Or R" are hy(ll o~en~ Cl-C~alkyl, ()11, C6-C~2alkoxy~ Cs-C8CyC10-alk()xy, ~IIlyl, I?Cll;~,yl ora~clyl, ill p~lllic~ ll hy(llo~cll 01 nlc~llyk TtlOSC COlllpOUll(L'; ol tllC rOrmUhl (I) ~Ir(` plclcl rc~ in whicll A i~i onc of lhc ~roups of lhe l'onnulae (11a)-(11~) in which X3 iS -()- ur >N-R~2 whcrc R12 i~i hydro~cn, Cl-C12alkyl, Cs-Cxcycloalkyl which is unsubstiluled ()r m(~no-, di- or tri-sub~titute(3 by Cl-C4alkyl;
hen~,yl which i~s unsub~stiluted or mono-, (li- or Iri-.~ b~slilule(l hy C~-C,I~llkyl;
elrahy(lrorurruryl, C2-C3~llkyl suh~;lilllle(l in lhe 2- or ~-po~iilioll by Cl-C4alkoxy, by li-(C'I-C'"~Ilkyl)-amillo or by a l-pylroli(lyl, I-pipeli(lyl (!1' 4-morl-ll()linyl group, or Rl2 is a ~rollp ot' lhe l'ormula (IV) or one Or the ~ro~lp~ ol' lhe l'orlllulae (Va)-(V(I) in which X5 iS
-O- or >N-CI13 an(l X6 is -C:1-12CI12-, -C'()- or -C()C'()-, ()r X 3 hs a I ,~-pipCla~/.inC(Ii ,~roul~, p k~; 1, 2 or ~ all(l, when p i.~i I . R~ i~; (,2-(:, l2~llk.lnc(liyi ~nl(l, wllc n 1~ is ?,, Rs is C~2-C~ llk~lnelliyl~ C'(,-C,7cy~10~llk~ iyl~ "I)i~"y(lo~,ll;;lll~,lliyl ol ~1 l'l0~
-Cll-X7-RI~-wlleleX~ -()-ol >N-RI~willl l~l,ll-~hl~ "l(ylol ((Il-C'(,(Ilkoxy)--(Cl-12)(1 C~llbOrlYI~ Rl3 j~; C3 CI laIkarIC(I;YI al1(l (I j~ ~CIO 01 1, .11~(~, WII~I1 P j~ S j.~ C'3 C'4~1lk~
lCllaYI~ R() jS a~; (ICI`;I1C(I ~IhOV( I'or Rl2. R7 i~ '2-(ll l illkal~( (liyl, RN j~S l1Y(Ir()~CI1 Ul mClhYI~
R., k'; a (lil'('Cl b011(1, Cl-C1 2illkilll(~(liyl 01 il ~,1 0nl) -X7-R l 3- wilh X7 illl(l Rl3 a~ ~ICI ;nC(I
ill)OVC~ RI() ;h; l1Y(IrO~CI1 01 111Cll1YI il(1(1 R 11 ;S -( '1 12-, R 1 j~ ;llkYI~ PI~CnYI~ Cl-C~,alk()xy 2 iII1(I R3 wllicll i"~ i~clllicill 01 (1;~ -(: "illkyl 01 ~ "YI ", R2 is also ~, m ~ llllllbcr ~10lll I lo X() ill"l 11 V~ 10 lo ()() ~Yo "r th~ sumIn t- n~ x~ h~; a~ clïllc(l 1()1 Rl Or is ~ roul~ (RIS)3~S;()- willl Rl5 hC;I-~ Cl C~ alkyl, X2 is hY(IIO~CI1, CI-C (~illkYI~ a ~IOUP (RIS)I~;- Or, Wl1CI1 Rl ~In(l Xl arC Cl C(~illkYI Or ]~l1CnY]~

2 ~

X2 is additionally a group -Si-X1, and, when m ~- n is a number from 3 to 10, Xl and X2 A
together also form a direct bond.

Those compounds of the forn)ula (1) arc parlicularly preferred in which A is one of the groups of the formulae (lla)-(lkl) in which X3 is -O- or >N-RI2 where Rl2 is hydrogen, C1-CIOalkyl, cyclohexyl which is unsubstituted or mono-, di- or trisllbstituted by Cl-C4alkyl; benzyl, tetrahydrofllrf~lryl~ C2-C3~1kyl substituted in the 2- or 3-position by methoxy, by ethoxy, by dimethylc~ o, by diethylamino or by 4-morpholinyl, or Rl2 is a group of the formul.l (IV) or one of the groups of the formulae (Va)-(Vd) in which Xs is -O- or >N-CI-13 and Xfi is -(`112CI 12- or -CO-, or X3 is a 1,4-piperazirle(liyl gro~lp, p is 1, 2 or 3 all(l, whel1 p is l, Rs ix C2~ lk;lne(liyl alld, when p i!i 2, Rs is C2-CI4alkllletriyl~
cyclohexllnelriyl or bicyelollel)lallelriyl or a groIlp - Cl l -X7-RI3- where R7 is -O- or -(C} 12)~, >N-RI4 with Rl4 being CI C"acyl or (Cl-C4alkoxy)c.lrbotlyl, Rl3 is trimethylene all(l q is zero or 1, and, when p is 3, R5 is propanetetrayl, R6 is as defillc(l above for Rl2, R7 is C2-CIlalk.lncdiyl, Rx is hy(lrogcn or melllyl, R9 is a direcl bon(t, Cl-CI2alk;lnediyl or a grollp -X7-RI3- willl X7 ;Ind Rl ~ t)eing as defincd above, Rlo is hydrogen or methyl and Rll is -Cl12-, Rl is Cl-C,~alkyl, plle1lyl, Cl-C"illkoxy or 01-1, R2 and R3 which are identicial or different are Cl-C~illkyl or pllellyl, or 1~2 is also 11y(1rogen, m + n is a nllmber from 1 to ~() and tl v.lries rrom zero lO ')() ~, ol l!le .~;nlll 1~1 -t- n, XI i~ ; dcl'illc d l`or Rl 01 ks a glollp 5)3SiO- wi~ s l~ g C ~ 1k~1, X~ ly(ll()~ll, Cl-( ,~;llkyl, ;l ~ ls) l l whell 1~1 ;In(l Xl ilre C`~ lkyl or pl)ellyl, X2 is ild(li~iollally a gro~ -Si-XI, an(l, wlle 1ll ~- 1l i~i .I rlllllll~r ~lolll :~ lo 1 () X I illl(~ X2 to~ c~ o ~orlll ;1 (lircc~

'I'llose collll~oll~ ol 1~1~ rollll~ll;~ (1) ;~1~ ol ~ ;l ill wlli~ll A i~ lolll~ of II-e forllllll;l (11.1) 01' (111~) in whi(:ll X ~ is -O- or >N-R,2 wllcrc Rl2 is llydlogcn, C~-Cxalkyl, cyclollexyl, hellzyl, Iell ;Illydlollll I nl-yl~ a group Or the fonlllllll (IV) or a group of the fonllula (V~) or (Vb) in whicll Xs is -O- or >N-('l 13 and X6 is -Cl 12CI 12- or X3 is a 1,4-pipelllzille(1iyl groul), p is 1 or 2 all(l, whell p is 1, Rs is C2-CI()alk.ule(liyl ;In(l, whell p is 2, Rs is C`2-Cl,1alk;lllell iyl~ R(, is lls dcrll,c(l at~ovc for R 12, R7 is ( 2-C ,~alk.lllc(liyl, Rlis Cl-C~.Ilkyl, Cl-C'-~alkoxy or 01 l, R2 ;In(l R3 ale Cl-C`~alkyl or R2 is also hydrogell~ m ~ n ~ ~J `3 ~

is a number from 1 to 50 and n varies from zero to 75 % of the sum m + n, Xl is as defined for Rl or is a group (Rls)3SiO- with Rls being Cl-C3alkyl, X2 is hydrogen, Cl-C3alkyl, a group (Rls)3Si- or, when Rl and Xl are Cl-C3alkyl, X2 is additionally a group -Si-Xl, and, A
when m + n is a number from 3 to 10, Xl and X2 together also form a direct bond.
l hose compounds of the formula (I) are of particular interest in which A is a glOUp of the formula (lla) or (llb) in which R4 is hyclrogen or methyl, X3 is -O- or -NH-, p is I or 2, and when p is 1, Rs is C2-C]()alkanediyl and, when p is 2, Rs is C2-CI~alkanetriyl, Rfi is hycirogcll, Cl-C,,~alkyl, 2,2,6,()-~ctralTIctllyl-4-pil)criciyl or 1,2,2,6,6-pcntalllethyl-4-piperi(lyl anci R7 is trimetllylene~ K 1 is snetllyl, metl1oxy~ etlloxy or Ol l, R2 and R3 are met11yl, 111 -t 11 i.5 a nlllllber from I to 4(), n varies froln %ero to 5() % of the sum m + n, X
is as defillecl ror Rl or is a group (C1-13)3SiO- an(l X2 is hyclrogen, methyt, ethyl, a group (Cl-13)3Si- or, when R] and Xl are methyl, X2 i5 .ICI(iitiOllally a group -Si-CH3, and, when A
m ~ n is a nlJmber fro~ll 3 to 1(), Xl .IllCi X2 tOgCthCr alSO fOl'ltl ~I ciirect bond.

In the compounds of the formu]a (I) A i.5 preferably a group of the formula cl 1 3 N~ X 3 ~ 5 1 13c ~ I 13 whcrc 1~4 is hy(Jrogcll or mctllyl, X3 is -O- or -Nl 1- all(l R~' is cthylcllc, p ropylelle or dccalnctllylcllc.

A furtl1er preferre(l meal1il1g of A is the glollp of tllc lorlllllla ~i7~

3C`~

R4--N ~--X3 - C--R5''--\ )~ /
1 13C Cl 13 where R4 iS hydrogen or me~hyl, X3 iS -O- or -NH- and Rs" is a group -CH2-CH< or>CH-(C~-~2)3~

An especially preferr~(l meaning Or A ks lhe roup of thc lormula Il (' ('11 ~' li ~4 .. N~ N ~ 12) 3 1 13(- ( 1 13 where R4 i.s hydrogen or melhyl an(l R6 i.s hy~llog~ll or ('I-C4il1kyl.

rho.se compo~m(ls ol llle lorrllllla (1) ale also ol plllliculill in~lesl, in wllicll A is a group ol thc l(?~ UI~IC (Ihl), (llh) Or (llc) in WhiCIl R" is hy~lrogen ()I me~llyl, X3 iS -O- or >N-RI2 where Rl2 is hy(lrogen or Cl-C4~1kyl, p hx I or 2 all~l, WhCIl p iS 1, Rs hs C2-CI(~alkanediyl atld, when p hs 2, Rs is C2-CI,lalkallc~liyl, R(, i~s (IS (Ielill(~(l al)ove lor l~ 12, 1~7 i~s C2-c4~llk~lll(~(liyl~ l~X i~ ~ly(lro~ll 01 ll~ yl, 1~ ('I,,;Ilk(lll~(liyl, 1~1 i.~; (`I-('IIIIkyl, C~-C'~Ilkoxy ~ 01l, 1~2 ~ Ir~ .llkyl ~ 2 i~ o lly(llo~ lllllh~
r10,.. I ,0 s() ~ 1 " v.lri~ ro ~o 7~ ol 111(~ .li(llll lll ~ lll X I i.~ ;l~; (I~I ill~(l lol l~l ()l~ is a glOllp (Rls)3~$i()- willl I~ls heillg C'~-('3.l1kyl, X2 i.s hy(llogell, C'l-C3alkyl, a ~r()u l l (Rl~)3~i- or~ wh~ll Rl .In(l Xl .Irc~ ('I-( lall;yl, X2 i.s ll(kli~ioll.llly a gloul~ -~Si-XI, and, wh~n 1 he compoull(ls ol lhe l~r~.sell~ inv(~nlion clln h(~ pl(~p,ll(~d hy ~liVCl.';C pl0C(~SSCS known per ~s~. .

I'rocess 1 - Whcll m k~ 1, n i.s ~.~ro, Rl i.s ('I-(`~lllkyl or Cl-C'xlllkoxy, Xl i.s Cl-Cxalkyl, Cl-C8alkoxy or a ~roup (R~s)3SiO- an(l X2 is Cl-C8alkyl, a group (R~s)3Si- or a group Rl Xl-Si- with Rl and Xl being Cl-C8alkyl or phenyl, the eompounds of the formula (1) ean A
bc prepared, for examplc, in aceor(lancc with schcme 1 by reacting an alkene, eapable of forming a ~roup A as derlne(i above, with a sil.lne of the formula (V1) Kl K~
\ /
Xl--Si--()--X2 -~ C=C ~ Xl--Si--O--X2 Il A
(Vl) (Vll) lc I
'I'hc hydrosilyla~ion reaetiol1 (scc Spcier, J.A.C.S. 79, 974, (1957)) is in partielllar e~rricd o~lt in thc prcsenec of a cat~llytic ~]I~;lntity of Pd, I't, Rh or dcriv;ltivcs thercof, prcrcr;ll)ly of Yt ancl Rh eomplcxes, in p~lrtieul~lI 1121'tCI6 ;Ind thc l~t( 12(1'h-( 1 I=(,l 12)2 conlpIcx, opcr;ltill~ ill thc ;Ibscllcc ol' solvellt or ill ~111 incrt solvcnt, ror cx;nnl)lc tctr~lhy(lrol'llr;lll, (liox~nlc, hcx~lnc, hept~lllc, cycIohcx~ c, tolncl-c or xylcnc, ~It tcmper~ltllrcs bctwecn 6()C
;n1(1 15()C, prcrer~bly bctwccIl X()C ~In(l 13()C.

I'roccss 2 -13y tot;ll or p;lIti;ll hy(IIolysis ol th( colnpolllI(ls ol ~hc lonI~ (Vll) COllt;lillill~

I)~illL~ ;It l~;lst 2 ;1I1(1 I1 l~ .cIo ~ ol~t;liIl~(l by coll(l~Ils;llioll l~ liOII~.

'I'llC hy(lrOIySiS ~111(l COlldCllS~ltiO11 I'C;lCtiOll!i ~IrC pl'CI'cl'~lbly CllrriC(l 011l Silllllll;111CO~lSIy, by Irc;lliIl~ Ihc comI)ollll(Is ol Ihc lorllllII;l (Vll) coIllllillill~ ;llkoxysil~lnc ~rolIps with W~ltCI' ill ~1 (IU;llllity 01' ~ll IC;I!;t ()..'i 11101 pCI' ;llkOXy ~I'Ollp it1 IhC pl'CSC11CC 01' ~1 C;l~;lly.';t, pl'Cferllbly ;111 inor~lIlic ;~ci(l, lor CX;1111pl~ CI, I 12~;04 or 11~1'0,~, or .In or~;lnic ;Ici(I, lor cx;lmplc formic or ~ICctiC ~Icid, oper~ltiIl~ ;lt tell1pCl';)tlll'CS 11~tWeC11 -l()"C ;In(l 5()"(', pler~l;,bly bctween ()C
ilnd 3()C.

WI1CI1 tl~c hy(ll'OIy.';iS/COll(lCll!~;;lti(~ll rC;IC~iOIl i`; (,;lrl'iC(I Oll~ ill tlle pl'CSellCC ()1- Ippl'Opri-ltC
tilics Orll (I;S;IOX;II1C ~ 2()~ IhC COlllpOllll(lS ol thc l'Ol'111lll;1(1) with 111 bein~ ~It ~7~5~` L

least 2 and n being zero, in which Xl is a group (Rl5)3SiO- and X2 is a group (Rl5)3Si-, can be obtained.

The hydrolysis/condensation reactions are preferably carried out in water or in the same solvent as that used for the preparation of the compounds of the formula (VII).

Process 3 - When m is at least 2 and n is othcr than 7.cro, thc compoullds of the formula (1) can be prepared by hydrolysis/condensation of mixturcs in thc appropriate ratios of compounds of the formula (Vll) and of compounds of the formula (Vlll) or (IX) Il 2 / K7 K16~ 6 ~ r K3 K3 r (Vlll) (IX) in which R2 an~ R3 arc ~IS (ICrincd ilbovc, l~lfi is Cl-C8alkoxy an(l r i~ 3 or 4, if desired in thc prescllcc of .Ipplopriil~c ~U.IIltitiCS of thc disilox,lnc l(Rl5)3Si]20 as chain terminator, operating under thc con(litions indicatc(l in proccss 2.

Process 4 - COI11I)O~II1(IS of thc for~ ll;l (I) W;II1111 l~cin~, .It lc;lsl 2 ~111(111 I~Cill~ C(~ 10 01' other th.ln 7ero, call also l)e prcp;llc(l l~y rc~lclill~ a COIIIpOllll(l ol' Ih( ~ 1 nllll~l (X) xl t ~ 0-~X2 (X~

whcre Xl, X2, ~ 2 .nld 1~3 ,Ire as (Iclille(l .IbOVC, CX(:Iu~ 2 ~Iefillc(J as hydrogcll, witl appropri.llc qu.llltilics of all alkcllc cal).lblc ol fornlill~ a group ~ as dcrille(l above, opcr~ltin~ ~s staled ull(ler process 1.

In this rc.lclion, i~ is possiblc to h;lvc a lotal or p;lrli.ll SUt)Stit(ltiOII of thc hydro~en atoms boull(l lO thc silicoll .IIOlllS, bllt llOt ]CSS th.ll. 3() ~Yo of Ihcory.

~ ~ 3 As -mentioned at the outset, the compounds of the fo~nula (I) are hi~hly effective in improving the light stability, heat st~bility and oxidation stability of organic materials, in particular synthetic polymers and copolymers Examples of such organic materials which can be stabilised are:

1 Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybutene-l, polymethylpentenc-l, polyisoprene or polybut,l(licne, as well as polymers of cycloolefins, for instance of cyclopentenc or norbornenc, polycthylenc (which optionally can be crosslinked), for example high dcnsity polyethylene (I-IDI'E), low density polyethylene (LDPE), lincar low dcl-sity polyctl-ylene (LLDPE), branched low density polycthylene (BLDI'E) 2 Mixtl-rcs of thc polymers mcn(iorlc(l ull(lcr 1), for CX.llllplC mixl~lrcs of polypropylene with polyisobutylene, polypropylcnc with polyc~hyletlc (for cxiample PP/~IDPE, PP/LDPE) and mixtures of different typcs of polyethylene (for example LDPE/HDPE) 3. Copolymers of monoolefines and diolcfines witl1 cllch other or with other vinyl monomers, such as, for cxample, ethylcllc/propylcne, lincar low dcnsity polyethylene (1J1~DPE) an(l ;'S mixturcs with low dcllsity polycthylene (LDI'E), propylene/b~ltene-l, etllylenc/hexcl-e, cthylene/cthylpcntcnc, cthylcne/t-eptcne, cthylene/octcne, propylene/iso-b~ltylene, ethylene/bu~ene-l~ propylcnc/bllta(licne, isohutylcne/isoprcnc, cthylene/alkyl acrylates, cthylcnc/alkyl mclhacryl;ltcs, cthylcllc/villyl acelatc copolylllel s a~ heir copolymcrs witll calbon monoxi(le or ctllylcl1c/;lclylic aCi(l ('OpOIylnCrS ;111(l thCil' ~ tS
(ionolllcrs) an(l tcrpolymers Of ctllylcllc with plol)ylcrlc al-(l a dicnc, SIICIl as hcxa(licllc, dicyclopcllta(licllc or cthyliclene-llorbol ncnc; as wcll as mixtllrcs ol' sllch copolymers alld tllcir mixtures Witll polymcrs mcntionc(l in 1) al-ovc, for cxalllplc polypropylcnc/c~hylcllc-propylellc-col)olylllcrs, l,l)l'l~'/cthylcnc-vinyl acctate copolylllcrs (l~,VA), I,l)l'l~/ethylellc-,lclylic aci(l copolyll1cls (I~AA), l,I I)l'I /PVA, I_l,Dl'L~ AA alld St;ltiStiCIll or altcl nlltillg polyalkylclle/c;lrboll nlolloxi(lc-copolylllcrs as wcll as tllcir mixtures with othcr polymcls, for cxalllplc polyallli(le 3a 1 Iydrocarbon rcsins (for examl)lc Cs-C9) an(l hy(lrogcn~ltc(l modirications thereof (for example tackyfiers) and mixtures of polyalkylcnes and starch 4 l'olystyrcnc, poly-(p-lnctllylslylcnc), poly-(a-mcthylstyrcne)~

~ ~ 13 }~

5. Copolymers of styrene or c~-methylstyrene with dienes or aerylie derivatives, sueh as, for example, styrene/butadiene, styrene/aerylonitrile, styrene/alkyl methaerylate, styrene/maleie anhydride, styrene/butadiene/alkyl aerylate, styrene/butadiene/alkyl methaerylate styrene/aerylonitrile/methyl aerylate; mixtures of high impaet strength from styrene eopolymers and another polymer, sueh as, for example, from a polyaerylate, a diene polymer or an ethylene/propylene/diene tcrpolymer, and block copolymers ofstyrene, sueh as, for example, styrene/butadiene/styrene, styrene/isoprcnc/styrene, styrene/ethylene/butylene/styrene or styrenc/ethylene/propylene/ styrcne.

6. Graft copolymers of styrcne or (x-mcthylslyrene sueh as, for example, styrene on polybuta(licllc, s~yrcnc on polybllt.l(ficllc-styrcnc or polybll~.ldicllc-.lerylollitrile; styrene and aerylonilrilc (or mclll,lcrylol1ilrilc) on polybut,ldicllc; slyrenc all(t malcie anhydride or malcimide 011 polybut.l(liclle; styrcnc, acrylonitrilc and malcie anllydri~fe or maleimide on polybutadiene; styrene, acrylonitrile and methyl methacrylate on polybutadiene, styrene and alkyl acrylates or methacrylates on polybutadiene, styrene and aerylonitrile on ethylene/propylene/dienc tcrpolymers, styrene and aerylonitrilc on poly,lerylates or polymethacrylatcs, styrcne and acrylonitrile on acryl.lte/but.l(licne copolymers, as well as mixturcs thereof wilh thc eopolymers listed under ~), for inst.lnce the coyolymer mixtllres known as ABS-, MBS-, ASA- or AES-polymers.

7. Halogen-containing polymers, SllCIl IS pOIyClllOroprcllc~ CIllOrinll~C(l rUbllel'S, chlorinatcd or sulfochloril1;llc(1 polyelllylcrlc, copolylllels oi ctl1ylel1c ,llld ChlOrirlatCII
cthylenc, cpichlorolly(lrill h~;nllo- ;IIId copolylllcls~ polylllcls l'roln h;llogcll-coll~.lillillg vinyl eompoun(ls,.ls lor cxamplc, poly- vinylclllori(le, polyvillyli(lcllc clllori(lc, polyvinyl fluoride, polyvinyli(lcne fluoride"ls well as copolymcrs tl-ercol, as lor cxalllple, vinyl ChlOri(lC/Vinyli(lelle ChlOri(lC, Villyl ChlOri(lC/Villyl .lCCt.ltC or VillylidCIlC ClllOri(JC/Vill acct.llc copolylllcrs~

X. Polylllcrs whicll arc dcrivc(l from (~ -lllls~ltlll~llc(l ;ICidS .Illd dc rivalivcs therco~, such as polyacrylatcs all(l polymctll;lcryl.ltcs, with bulyl acryl.llc inlp.lcl rcsist,lllt modi~led polymcthyl mcthacryl.ltc, polyacrylalllidc and polyacrylonitrile.

9. Copolymcrs frOltl thc rllOllOltlCrS IllClltiOllCd lm(ler X) with CaCIl o~hcr or wilh other llll!UltUr.ltCd IllO110111CrS, SllCIl .IS, f'or ill.';t.lllCC, .ICrylOllitrilC/ bllt;ldiCIlC, ;lClylOllitrile/
aclyl;lte, acrylollitl ilc/alkoxy;llkyl acryl.ltc or acrylonilrilc/vinyl h,llo(Tcllidc eopolymers or acrylonitrile/ alkyl methacrylate/butadiene terpolymers.

10. Polymers which are derived from unsaturatcd alcohols and amines, or acyl derivatives thereof or acetals thereof, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl ben~oate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate orpolyallylmelamine; as well as their copolymers with olefins mentioned in 1) above.

11. Homopolymers and copolymers of cyclic ethers, such as polyalkylene glycols, polyethylene oxide, polypropylene oxidc or copolymers thereof with bis-glycidyl ethers.

12. Polyacetals, such as polyoxymethylcne and those polyoxymethylenes which contain et11ylene oxitle as ia comonorncr; polyllcct.lls motlific(l Wittl thcrmopl.lstic polyurethanes, acryl~lles or Ml3S.

13. Polyphenylene oxides and sulfitles, and mixtures of polyphenylelle oxides with polystyrene or polyamides.

14. Polyurc~hanes which are derivcd from polyethers, polyesters or polybutadienes with terminal hydroxyl groups on the one side and alipllatic or aromatic polyisocyanates on the othcr sidc, ~s wcll as precursors thcreof (polyisocyanates, polyols or prepolymers).

15. Polyamides and copt)lyami(les which are dcrive(l frotll di;llllines an(l dicarboxylic acids and/or from aminociarboxylic aci(ls or thc collc~ spoll(lill~ lact~ ls, such a~
polyamitle 4, polyalni(lc fi, polyallli(lc ~)/(), ~1/l(), ()/~), ()/12, 4/(), 12/12 polyan1itlc 1 1, polyamidc 12, aromiltic polyallli(lcs obtaille(l by contlcllslltiorl Or m-xylene diamine and atlil)ic acid; polyamides prcparcd from hcxlllllctllylcllc(liillllinc alld isophthalic or/and terephthialic acid an(l oplionally all cl.lstoltlcr as nlo(lificr, for exarnple poly-2,4,4,-trimcthylhex,lmctllylcnc tcrcphttl,ll,ll)li(lc or poly-lll-l)llcllylcllc isophttn,llamide. I~urther copolylllcrs of the afolclTlentiolletl p(lly,llrli(lcs wi(h polyolcrills, olcfin copolymers, ionomers or chelllically bolldcd or gr.ll'(c(l el.ls(olllcls; or wi(h polyc(llcrs, such as for instance, with polyethylenc glycols, polyprol)ylclle glycols or polytetralncthylene glycols.
I'olyamides or copolyamides mo(lificd wi(h I I'I)M or ~\13S. I'olyamitlcs condensed during processing (RlM-polyamide systems).

16. I'olyurc.ls, polyillli(lcs al-(l polyallli(lc-illli(les~

17. Polyesters which are derived from dicarboxylic acids and diols andl[ch]or from hydroxycarboxylic acids or the corresponding lactones, such as polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate, poly-[2,2,-(4-hydroxyphenyl)- propane1 terephthalate and polyhydroxybenzoates as well as block-copolyether-esters derivcd from polyethers having hydroxyl end groups.

18. Polycarbonates and polyester-carbonates.

19. Polysulfones, polyethcr-sulfoncs and polycther-ketones.

20. Crosslinked polymcrs which are dcrived from aldehydes on the one hand and phenols, ureas and melamines on Ihe other halld, such as phenol/formaldehydc resins, urca/formal(lchy(lc rcsills al-~l mcl;llllirlc/formal(lclly(lc rcsins.

2l. Drying all(l non-dryitlg alkyd rcsins.

22. Unsaturated polyester resins which are derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslinking aL~ents, and also halogcn-containillg mo(lifiC.Itiolls tl)crCof of low inflamm.lbility.

23. l hermosetlin~ acrylic rcsins, dcrived from substitllted acrylic cstcrs, SUCIl as cpoxy-aclylatcs, urcthanc-;lcrylatcs or polycstcr-acrylatcs.

24. Alkyd resinS, polycs~cr rCSillS or ;ICIyl;ltC rCSillS ill ;IdllliX.IllrC wi~h 111Chlrl1inC rCSil1S, ure~ resins, polyisocyan;ltcs or cpoxi(le rcsins as crosslil1killg agCI1tS.

25. Crosslinkcd CpoXi(lC ICSillS WlliCh IIC dCriVC(I frOnl polycpoxidcs, for CXalllplC rrOIll bis-~lycidyl ctllcrs or fionl cycloalipl);ltic dicpoxi(lcs.

26. Natur,ll polyll1cl s, sllCII as ccllulosc, rul)l-cr, gcl.l~ille al1(1 dcriv;ltivcs thcrcor WlliC11 arc cllcmic,llly modified in a polyll1cr-llol1lologolls m;l~lllcr~ such as CCIlUlOSC acetatcs~
ccllulose propion.ltes and ccllulose bulyr;lles, or tl1c cellulose etl1ers, SUCIl as mcthylcellulose; rosins ~md tllcir dcrivativcs.

27. Mixlurcs Of polylllcrs as mcl1liollc(1 al10vc~ for cx;l~ )lc l'l~/EI'DM7 I'olyamide 6/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylales, POM/~hermoplaslic PUR, PC/lhermoplasLic PUR, POM/acrylatc, POM/MBS, PPE/H~PS, PPE/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPE.

28. Na~urally occurring and synthelic organic matcrials which arc pure monomeliccompounds or mixlurcs of such compounds, for exatnl71e mineral oils, animal and vegctable fats, oil and waxcs, or oils, fats and waxe.s base(l on .synthetic eslcrs (e.g.
phthala~cs, adipatc.s, phosphatcs or trimellithates) alld also mixturcs ol synthetic csters with mineral oils in any weight ratio.;, whieh ma~erials may be used a.s plasticizer for polymcrs or a.s tcxtilc .spinning oils, as wcll .IS a(lllCOU.S ClllUI.siOrl.s 0f .SllCIl Ill.ltCli.llS, 2'). A(lucolls ellllll.;ion.; ol n.ltlll.ll omsynth~Li~ rul-l-el, c.~. n llul.ll lalcx or laticcs of calhoxyhltc(l stylcllc/hu~a(licllc copolymcls.

Thc eompoun(is of thc formula (I) arc partieularly ~suit.lble for iml7rovillg tlle light ~stabili~y, hca~ .stabili~y and oxidation ~st.lbili~y ol p01yolerin.s, e.;pecially polyctllylellc all(l 70lYprol7ylcnc~

I-hc coml70ull(1s ol Ille lorlllul a (I) can bc u.i~(l in mixlulcs willl or~ anic materi.lls in various propol~ion.s dcl7cn(1ing on the natulc of the maleri,ll to hc .slabili.se~l, on Ille Cn(l USC
an(l 011 ~hc i7lcscn(;c ol' olhcr a(l(iitivc.s.

Ill gCllCI.II, iI iS ~ 171()i71i;11(' 1() ll~SC, 1()1 CX111l1111C, ().()1 l() S ~ 17y wci;,llI ()I lllC C()11117()lll1(1S
of lllC iO111lUIa (1), ICIaliVC Io tllC WCiglll 01 lllC 111.1~(Ui~ll lo hc .'ikll~ili.';C~I, pl( Icl.lhly bclwccll ().().~ all(l 1 'Y,.

11l L~llcl.ll, ~ (,ol~ ollll(l. ol' ~ 1'olll11~ O lll~ l~olylllcli~ llcli~ s Thc colllpoull(is ol Illc lollllul.l (1) C.lll I-c illCOli7()ralC(I ill thc ~)OIynlCliC m,ltcri IIS in thc 17~ 01111 01 (~ llC(l il~ W~IX(~S, oil~s 01 i701yl~ 1S.

T~ ollll~ollll(l.~; ol lll~ ~()1lllll1.l (1) ~.1ll 1~ ill~l)ll~ol~ olylll~ lls 17y }

~ 17 ~

various processes, such as dry mixing in the fonn of powder, or ~et mixing in the form of solutions or suspensions or also in the form of a masterbatch; in such operations, the polymer can be used in the fonn of powder, granules, solutions, suspensions or in the form of latices.

The materials stabilised with the products of the formula (I) can be used for the produetion of mouldings, films, tapes, monof1laments, rlbres, surf.lce coatings and the like.

If desired, olher conventional additivcs for synthetic polymers, such as ,mtioxidants, UV
absorbers, nickel stabilisers, pigmcnts, fillcrs, pl"sticisers, antistatic agents, flarneproofing agents, lubricants, corrosion inhibitors and metal dcactivators, can be added to the mixt~lres of the co-npou1lds of the formllla (1) witl- the or~anic materi,lls.

Particul.lr examples of ~dditives WiliCIl Cllll bc lI.';C t ill mixtlJre with the compounds of the formul.t (I) are:

1. Antioxidants 1.1 Alkylilt dmonop er_ols,forexilmple2,6-di-tert-butyl-4-methyl-phenol,2-tert-bl1tyl-4,6-dimetllylpllcnol~ 2,6-di-~ert-butyl-4-etllylphcllol~ 2,6-cli-tert-butyl-4-n-butyl-phcnol, 2,6-di-tcrt-butyl-4-i.i;o-b~ltylphenol~ 2,6-(ticyclopcntyl-4-mcthylphenol, 2-(o~-methylcyclohexyl)-4,6-(timetllylpllellol, 2,fi-(liocta(lecyl-4-methylplle1lol, 2,4,fi-tri~
cyclohexyl-ptlellol, 2,6-di-te1t-b~tyl--4-lnetlloxyllletllyl1)llellol~ 2,6 di-llol1yl-4~ elllyl-p~lCI101, 2,4-(lilllCt~ly~ lyl-~ yl~ '11()l7 2,~ t~lyl-()-( l -111~1~1yl=
hcptiadcc- 1 '-yl)-phellol, 2,4-dilllctllyl-()-( 1 '-mc~llyl- lri(lcc- I '-yl)-pllcllol ;~n(l mixl~lres t~lel of.

1.2. Alkylthiome1hyll?llellol~s~ f'or ex;llllple 2,4-dioctylthiomethyl-6-tert-b~ltylphcnol~
2,4-diocty1tllionlethyl-6-1lletllyll)llellol~ 2,4-~lioctyltllio1lletllyl-6-etllylpllcnol~ 2,fi-di-(lo-dccyltlliolllctllyl-4-rlollyll)llellol.

1.3. t-lydlo(LIinones "nd alkyl1lted lly(llo(lllill(?llest l'or ex;~ ple 2,6-di-tert-butyl-4-methoxy-phenol, 2,5-di-telt-butyllly~il-o(l~1illolle~ 2,5-di-tcrt-amylllydroq~1inone, 2,6-di-phcllyl-4-octilctccyloxyphcllol~ 2,6-di-tcrt-l)~llyl-hy(Jro(lllinonc~ 2,5-di-tert-blltyl-4-hy(lroxy.lllisolc, 3,5-di-tcrt-butyl-1-hy(lroxyllllisolc, 3,5-di-tcrt-butyl-4-hydroxy-pllcllyl-stc;lrlltc, bi.s-(3,5-(li-tcrt-butyl-4-lly(lroxypllcllyl)adipatc.

1.4. Hydroxylated thiodiphcnyl ethers, for example 2,2'-thiobis(6-tert-butyl-4-methyl-phenol), 2,2'-thiobis(4-octy]phenol), 4,4'-thiobis(o-tert-butyl-3-methylphenol), 4,4'-thio-bis(6-tert-butyl-2-methylphcnol), 4,4'-thio-bis-(3,6-di-sec-amylphenol), 4,4'-bis-(2,6-dim-ethyl-4-hydroxyphenyl)-disulrlde.

1.5. Alkyliden b~phenolsl for example 2,2'-mcthylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebisj4-1netllyl-6-(c~-mettlyl-cyclohexyl)phenolJ, 2,2'-methylencbis(4-methyl-6-cyclohexylphenol), 2,2'-mcthylene-bis(6-nonyl-4-methylphcnol), 2,2'-methylenebis(4,6-di-ten-butylphenol), 2,2'-ethyl-idenebis(4,6-di-ten-butylphcllol), 2,2'-ethylidcnebis(6-tert-blltyl-4-isobutylpllellol), 2,2'-mctllylcnebisl6-((x-mclhylhcllzyl)-4-1lotlylpllclloll, 2,2'-mcthylcnebislfi~-(a,a-dimcthylbcn%yl)-4-nollylpll( n01 l, 4,~t'-mcll)ylellcbi~(2,6-di-tcrt-b~ltylpllenol), 4,4'-methylcnebis((~-tcrl-butyl-2-1llclllylpllcllol), 1,1-bis(5-tern-butyl-4-hydroxy-2-methylphenyl)butanc, 2,6-bis(3-ten-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tlis(5-ten-bl~tyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycol bisl3,3-bis-(3'-tert-butyl-4'-hydroxyphcnyl)butyratel, bis(3-tcn-butyl-4-hydroxy-5-1netllyl-phenyl)dicyclopent;ldicnc, bisl2-(3'-tert-b-ltyl-2'-hy(lroxy-5'-metllylbcnzyl)-6-tert-butyl-4-mcthylpllcnyl Itcrcplltl-al;ltc, 1, I -bis-(3,5-dimctllyl-2-hydroxyphenyl)blltan, 2,2-bis-(3,5-di-tcrt.-butyl-4-hy~lroxyphcnyl)-propan, 2,2-bis-(5-tert.-butyl-4-hydroxy-2-me(hylphcnyl)-4-1l-do(lccyllncrc;lplo-bllt;ln~ 1,1,5,5-tctl;l-(5-tcrt.-butyl-4-lly(lroxy-2-methylphcnyl)-l~cl~

1 6. 0-~ N- .In~ S-l)cll~yl co!n~olmds, for exall1plc 3,5,3',5'-lclr;l-tclt.-butyl-4,4'-(lihy(lroxy-dibenzylethcr, octa(lecyl-4-hy(lroxy-3,5-dillletllylbenzyl-rllcrc;lpto;lcctate~ tris-(3,5-di-tcrt.-butyl-4-lly(lroxybcllzyl) ;IlllillC~ bis-(4-tcrt.-b~ltyl-3-llydroxy-2,fi-dimcthylbcnzyl)-dillliotclcplltll;ll;ltc, bis-(3,~-(li-tcrt.-b(ltyl-4-lly(lroxybcllz,yl)-slllfidc, isooctyl-3,5-di-tclt.-bu(yl-4-lly(lloxybcllzyl-1llclc;ll)lo;lcct;ltc~

1.7. 1 lv r( xyb~ !lzyl;lt~ d M.!lonl!tcs, lor cxalllplc diocta(lccyl-2~2-bis-(3,5-~li-tcrt.-bulyl-2-llydloxybcn7.yl)-malon,lte, di-octadecyl-2-(3-tcrt.-butyl-4-lly(lroxy-S-mctllylbcn7.yl)-m;lloll;ltc, ~li-dodecylmcrcaptoethyl-272-bis-(3,5-di-tcn.-butyl-4-hydroxybcnzyl)-m;llon;ltc, 1)i-l4-(l~l~3,3-tctratllcthylbutyl) 2,2-bis-(3,5-di-tcrt.-blltyl-4-lly~lroxybcllzyl)-rllaloll;ltc.

1.8. Hydroxybenzyl-Arom~ltics, for example 1,3,5-tris-(3,5-di-tert.-butyl-4-hydroxy-benzyl)-2,4,6-trimethylbenzene, 1,4-bis-(3,5-di-tert.-butyl-4-hydroxybenzyl)-2,3,5,6-tetra-methylbenzene, 2,4,6-tris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-phcnol.

1.9. Triazine Compounds, ~or example 2,4-bis-octylmercapto-6-(3,5-di-tert.-butyl-4-hydroxyanilino)- 1 ,3,5-triazine, 2-octylmcrcapto-4,6-bis-(3,5--di-tert.-b~ltyl-4-hydroxyanilillo)- 1 ,3,5-triazine, 2-octylmercapto-4,6-bis-(3,5-di-tert.-butyl-4-hydroxypllclloxy) - I ,3,5-triazine, 2,4,6-tris-(3,5-di-tert.-b~ltyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-~ris-(3,5-di-tert.-butyl-4-hydroxybenzyl)-isocy.lnuratc, 1,3,5-tris-(4-lcrt.-blltyl-3-hydroxy-2,6-di-mcthylbcnzyl)-isocyanur~lte, 2,4,~ rh.-(3,5-(li-tcrt.-blltyl-4-lly('lloxy~ cnylcthyl)-1,3,5-tria~.inc, 1,3,5-tris-(3,5-(li-tcrt.blllyl-~J-hy(froxy~ cllylplopiollyl)-llcxahydro-I ,3,5-trhl;!inc, 1 ,3,5-tl is-(3.,5-dicyclol-cxyl-4 lly(froxybcllzyl)-isocy.lllllr(ltc.

1.1(). Benzylphosphonates, for cxample dimethyl-2,5-di-tert.-butyl-4-llydroxybenzyl-phosphonate, diethyl-3,5-di-tert.-butyl-4-hydroxybenzylphosphollate, dioctaclecyl-3,5-di-tert.-butyl-4-hydroxybenzylphospllon~ltc, dioct~l(lccyl-5-tclt.-butyl-4-lly(lroxy-3-methylbcll~.ylpllosphonate~ Gl-salt of thc 3,5-(li-tcr~.-b~l~yl-4-lly(lroxyl)cn~yl-pllospllollic acid rnonoethylcstcr.

~ cylarn_(?phen(?!r.~ f or examl)lc lallric aci(l 4-hy(lroxyallili(lc~ stc;lric aci(l 4-hy(froxyanili(fc, octyl N-(~,~-di-tert-l)lllyl-4-hy(lroxyl)llcllyl)-c;lll);llll;llc.

! 1 2._E~tcr~ofl3-(3~ c~ yl~I-llY(ll~oxy~ lyl)l~rol~ (lwi~ lollo-polyhy(lric alcohols~ e.~. Wittl nlctll;lllol, ctll;lllol, octa-lcc;ll-ol, I ,(~-hcx;lllc(liol, I ,')-noll;lnc-diol, cthylcllc L~lycol, I ,2-propallc(fiol~ ncopclltyl L~lycol, tlli()(lictllylcrlc ~Iycol, dictllylcllc ulycol, tricthylcnc ~Iycol, pclltacrytllli~ol, tris(lly(lroxyctllyl) isocy~ lrate~
N,N'-bi~(hy(froxyc~llyl)oxalic aci(l di;lllli(lc, '.~-~hi,lull(l( callol~ .-tlli;lpcllta(lecanol, tri-nlctllylllcxanc(liol, tl inlctllyloll)lol);lllc~ ~1-lly(lroxylllctllyl- 1 -pllosl)11;l-2~6~7-trioxabicyclo-l2 2.21-oct;lllc _13. Esters_of l3-(5-tcrt-t)lltyl-4- lydroxy- 3-m tllylphcllyl)~ i(?llic a_d with mono- or polyhy(lric alcollol~i, C.~. witll methanol, ethallol, octa(lccanol, i ,6-llcxallediol, I ,~)-non~ne-diol, ctllylcllc ~Iycol, 1,2-prol)~lllc(fiol~ ncol)clltyl ~Iycol, thio(lictllylcl)c ~Iycol, diethylenc ~Iycol, trictllylcllc ~,lycol, pclltacrytlllitol, tliS(ily(llOXyC~llyl) isocyallllrate~
N,N'-bi' (lly(lrOXyCtllyl)ox;llic aCi(l dialTli(lC, 3-thhlUn(lCCallOI, 3-thiapelltadeCanOI, tTi-?

methylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabieyelo-~2.2.2]-oetane.

1.14 Esters of 13-(3,5-dieyelohexyl-4-hydroxYphenyl)propiol~ic acld with mono- or polyhydrie alcohols, e.g. with methanol, ethanol, octadeeanol, 1,6-hexanediol, 1,9-nonane-diol, ethylene glyeol, 1,2-propanediol, neopentyl glyeol, thiodiethylene glyeol, diethylene glyeol, triethylene glyeol, pentaerythritol, tris(hydroxyethyl) isoeyanurate, N,N'-bis(hydroxyethyl)oxalie aeid diamide, 3-thiaundeeanol, 3-thiapentadeeanol, tri-methylhexanediol, trimethylolpropane, 4-hydroxymethyl- 1 -phosplla-2,6,7-trioxabieyelo-2.2.2J-octane.

1.15 r~sters of 3,5-di---tert.-butyl-4-hy(lroxyplteny! acetie ilcid with mono- or polyhydrie aleollols, e.g. with meth;lllol, ethallol, ocla(lec;ltlol, l,(~-hex.ltle(liol, I,'~-noll;lllediol, cthylelle glycol, 1,2-plop;lne(liol, ncopelltyl glycol, ~hiodietllylene glycol, diethylene glycol, triclhylcne glycol, pcntaerythritol, tris(hydroxycthyl) isocyanurate, N,N'-bis(hydroxyethyl)oxalie aeid diamide, 3-thiaundeeanol, 3-thiapentadeeanol, tri-methylhexanediol, trimethylolpropane, 4-hydroxymethyl- 1 -phospha-2,6,7-trioxabieyelo-[2.2.2h~ctane.

1.16. A_d s of 13 (325-(!i-tert-blltyl-4-!ly(Jt-oxy~ lenyl)pr ~eionie acid e.g. N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexall1etllylene-(liamine~ N,N'-bis(3,5-di-tcrt-butyl-4-hydroxyphcnylpropil)nyl)tri-mctllylcllc-(liillllillc~ N,N'-bis(3,5-(li-1cr~-butyl-4-hydroxypllcnylpropiollyl)-lly(lr.l~ c.

2._JV ;I~)~0l11~r~ ;Itld li~ s-t~ se!~

2.1. 2_(2'-1 Iydroxyp-lc-yl~c!l70trilli~0lcs~ for CX;IIlll)lC the 5'-metllyl, 3',5'-~li-tert-blltyl, S'-tcrt-butyl, 5'-(1,1,3,3-tctl;llllctllyll)lltyl), S-cll10lo-3',5'-di-tel-t-l)utyl~ S-chloro-3'-tcrt-butyl-5'-1llclllyl, 3'-sec-blltyl-5'-tcrt-l)lltyl, 4'-octoxy, 3',5'-di-tcrt-amyl al-d 3',5'-bis((x,a- dhlletllylbelli~.yl), Illixture of S-clllOIo-3'-tert.-l)lltyl-5~-(2-octyloxyc;lrbollyl-cthyl)- arl(l S-chloro-3'-tcl t.-butyl-S'-I 2-(2-ctllylllcxyloxy)-cal bollylctllyl 1-~ 5-chloro-3'-tcrt.-butyl-5'-(2-mcthoxyc;lrbollylctllyl)-, 3'-tcrt.-butyl-5'-(2-mctlloxyc;lrbonylcthyl)-, 3'-tcrt.-butyl-5'-(2-octyloxyc;lrb()nylctllyl)-, 3'-tcrt.-butyl-5'-12-(2-etllylllcxyloxy)-carbonylethyll-, 3'-do(lecyl-5'-1lletllyl- alld 3'-tert.-butyl-5'-(2-isooctyloxycarbonylethyl)-2'-hydroxypllcnyl-211-l)e~ .tri;l~.olc(2), 2,2'-mctllylcllc-bisl4-(1,1,3,3-tctr;llllcthylblJtyl)-~-ben~ .ole-2-yl-pllelloll; prodllct ol ester in~ercll;lrlge of 2-l3'-tert.-butyl-5'-2 ~ u~ -~

(2-methoxycarbollylettlyl)-2'-hydroxy-pllenyl]-2~1-benztriazole with polyethylene glycol 300; [R-CI-12CI ~2-COO(CH2)3~ with R=3'-tert.-butyl-4'-hydroxy-5'-2H-benzotri-azole-2-yl-phenyl .

2.2. 2-~ydroxybenzophenones~ for example the 4-hydroxy, 4-methoxy, 4-octoxy, 4-decyl-oxy, 4-dodeeyloxy, 4 benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxyderivatives.

_ 3. Esters of substituted a ld unslll?st l ed benzoi a ids, as for example 4-tert.butyl-phenyl sillicylate, phenyl salicyl;lte, octylpllenyl salicylate, dibenzoylresorcinol, bis-(4-tcrt.butylbcllzoyl)-rcsorcitlol, hcllzoylrcsorcinol~ 2,4-di-tcrt.blltylphcllyl 3~5-(]i-lcrl~l)(ltyl-4-lly(lloxyhcllzo;l~ cx;l(lccyl 3,5-di-tcrt.butyl-4-llydroxybenzoatc, ~ctadecyl 3,5-di-tert.-bll~yl-4-lly(lloxybell%o;lte~ 2 methyl-4,6-di-tert.-butylphenyl 3,5-di-tcrt.-blltyl-4-hy(lroxybcnzo;ltc 2.4. Acrvlates, for ex~mple ethyl a-cyano-~ )llellylacrylate~ is(~ctyl a-cyallo-~,~-diphenylacrylate, methyl a-carl)omethoxycillnam;lte~ methyl a-cyallo-~ lethyl-p-methoxy-cinn;lm;lte, butyl a-cyano-~3-1lletllyl-p-methoxy-cinn;lm;lte~ nlethyl a-carbo-mctlloxy-p-Tncthoxycinll;llnatc ;Ind N-(l~-carbolllctlloxy-~3-cyanovinyl)-2-mcthylindolinc.

2..S. Nickel collll~ollll(!s, ror ex~llllple nickel colnl)lexes ol 2,2'-tl~io-his-1~-( 1,1,~,~-tetr;lmetllylblltyl)pllelloll~ sllcll a5 Ille 1:1 ol 1:2 conll)lex~ willl or withollt ;I(I(lilion;ll lig;lll(ls SIICIl ;1.5 Il-t)lltyl;ll~ c, tlielll;lll()l;llllille ol N cycl~ exyl(lictll;~ 1;ltl1ine~ t1iekel dibutyl(litllioc;lrb;lln;ltc, nickcl .5.l1ts ol'4-lly(lloxy-3,5-(li-tcrt-blltylbcllzyl-~ osphonic ;ICi( nlollo;llkyl e~sters, e.g. or the mell~yl or etllyl estcr, nickcl conlplexe~s or ketoximes, e.g. or 2-hydroxy-4-metllyl-pllellyl ulldccyl kctoxillle, nickel conll)lexe.s or 1-phenyl-4-l;luroyl-5-hy(lroxyl)yrll-zolc~ wilh 01' willloul .Id(li~ioll;ll li~all(l5 2.6. ~;tetic;llly hil!(!ere(l ;Inlille~ for cx;ulll)le bis(2,2,6,6-tctl;lllletllyl-pil~el-idyl) seb;lcate, bis-(2,2,6,6-tetrallletllyl-pil)eri(lyl) SUCcill;ltC, bis(l,2,2,6,~-pelltllllletllylpiperi(lyl) sebacate, bis(l,2,2,6,6-pcllt;llllctllylpipcri(lyl) n-blltyl-3,5-(li-tcrl-bulyl-4-llydroxy-bcnzylmalonatc, the condcns;ltion product Or 1-(2-hydroxyctllyl)-2,2,6,6-tctr;lrnctllyl-4-hyclroxypipcridinc an(l succinic ;ICi(l, ttlC con(lcns;ltioll pro(lllct ol' N,N'-bis(2,2,6,6-1ctlillllctllyl-4-pipcri(lyl)-llex;lllletllylelle(li;llllill(; ;ul(l 4-telt-oclyl;llllino-2~()-(licl~loro-1,3,5-tri;lzine, tris(2,2,fi,6-te-tr;llllctllyl-4-pil)cri(lyl) nitlilotli;lccl;llc~ Iclr;lkis(2.2,~),6-lctl;llllcttlyl-4- pipcr-2~7~

idyl)-1,2,3,4-butane-tetracarboxylate, 1,1'-(1,2-cthanediyl)bis-(3,3,5,5-tetrametllyl-piperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethyl-piperidine, bis-(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert.-butyl-benzyl) malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8-triazasprio~4.5ldecan-2,4-dion, bis-(1-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis-(1-octyloxy-2,2,6,6-tetra-methylpiperidyl) succinate, product of condensation of N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)-hexamethy]ene diamine and 4-morpholino-2,6-dichloro-1,3,5-triazine,product of condensation of-chloro-4,6-di-(4-n-butylamirlo-2,2,6,fi-tetr.lmethylpiperidyl)-1,3,5-triazine and 1,2-bis-(3-aminopropylamino)cthanc, product s~f condensation of 2-chloro-4,6-di-(4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl)-1,3,5-triazine and 1,2-bis-(3-aminopropylamino)ethane, ~-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspirol4.5 Idccanc-2,4-dion, 3-dodccyl- 1 -(2,2,6,6-tclrametllyl-4-piperidyl)pyrrolidin-2,5-(lion, 3-do(lccyl- 1-( I ,2,2,6,6 pcllt;llllctllyl-4-pipcl idyl)-pyrrolidin-2~5-dion.

2.7. Oxalic acid diarrlides, for examplc 4,4'-dioctyloxyoxanilide, 2,2'-dioctyloxy-S,S'-di-tert-butyloxanilide, 2,2'-didodecyloxy-5,5'-di-tcrt-butyloxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylamino-propyl)oxalalllidc, 2-ctlloxy-5-tert-butyl-2'-cthyloxanilidc and its mixturc with 2-cthoxy-2'-ctllyl-5,4'-(li-lett-blltyloxallilide and mixtllrcs of or~ho- alld para-mclhoxy-dis~lbstit~ltcd oxallilidcs and mixt~lrcs of o- and p-cthoxy-disllbstitutcd oxallilidcs.

2.8. 2~2-1-lydro_yphcnyl)- l~,~tria7.incsl for cxalnplc 2,4,~) tris(2-hydroxy-4 octyloxy-phcnyl)-1,3,5-tria7,inc, 2-(2-hydroxy-4-octyloxy-11llcllyl) 4,()-l)is(2,4~ lctllyll)llellyl)~
l,3,5-triazillc, 2-(2,4-dilly(lroxy-ptl~llyl)-4,()-bis(2,4 (linlc~llylpll- nyl)-1,3,~=lrhl~inc, 2,4-bis(2-hy(lroxy-4-plopyk)xypllellyl)-6~(2,4-dill,clllylpllcllyl)- 1 ,3,~-tl ia%ille, 2-(2-hy-droxy-4-oclyloxypllcllyl)-4~6-bis(4-lllclllylphcllyl)-1~3~5- tria;zillc, 2-(2-hydroxy-4-dodccyloxypllcllyl)-4,(-bis(2,4-dimclllylpllcllyl)-1,3,~-tlia%illc, 2-l2-hydroxy-4-(2-hy(lroxy-3-butyloxy-prol~yloxy)pllellyl 1-4,6-his(2,4-(lilllelhyl)- 1 ,3,5-tria%inc, 2-12-lly(lloxy-4-(2-l)y(lloxy-3-octyloxy-plol)yloxy)l)llcllyl~-4,(i-bis(2,4-dimetllyl)-t,3,5-tri-;!i' l llC .

3. Mctal dcactlvat )rs, lor cxalllplc N,N'-dil)llellyloxalic aci(l dhlmide, N-salicylal-N'-salicyloylhydra%inc~ N,N'-bis(salicyloyl)llydrazinc, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropiollyl)llydra%ine, 3-salicyl-oyl.lmino- 1,2,4-triazolc, bis(benzylidenc)-oxalo(lillydrazi(lc, Oxanilidc, i~iopllthalic aci(l dillydrazidc, scb.lcic aci(l-bis-pl)cnyl-hydr.l%ide, N,N'-di;lcetal-a(lil~ ic aci(l dilly(ll.lzidc, N,N'-bis-salicyloyl-oxalic acid dihydrazide, N,N'-bis-salicyloyl-thiopropiollic acid dihydrazide.

4. Phosl)hites and~hos ?honites~ for example triphenyl phosphite, diphenyl alkylphosphites, phenyl dialkyl phosphites, tris(nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, diiso- decyl pentilerythritol dipl-ospllite, bis(2,4-di-tert.-butylphenyl) pentaerythritol diphosphite, bis-(2,6-di-tert.-butyl-4-methylphenyl)-pentaeryt hritol diphosphite, bis-isodecyloxy-pentaerythritol dil)hospllite, bis-(2,4-di-tert.-butyl-6-methyl-phenyl)-pentaerythritol diphosphite, bis-(2,4,6-tri-tert.-butylphenyl)-pentaerythritol diphsophite, tristearyl sorbitol triphosphile, tetrakis(2,4-di-tert-butylphenyl) 4,4'-bi-phenylene diphosphonite, 6-isooctyloxy-2,4,X, I O-tetril-tert. -butyl- I 211-dibenz[d,gl -I ,3,2-dioxaphospllocin, (~-fluoro-2,~1,~, 1 ()-tctra-tcrt.-blJtyl- ] 2-rllctllyl-(libell~J[
,2-(liox;ll~lo~l)llocill.

5. I'eroxide scave~ersl for examl)le es~crs of ~-thiodipropionic acid, for example the lauryl, stearyl, myristyl or ~ridecyl esters, mercal)tobenzimi(t;lzole or the zinc salt of 2-mereaptobenzimidazole, zinc dibutyldithiocarbamate, diocta(lecyl disulfide, pentacrythritol tetrakis(~-dodccyl-mcrcapto)plopioll;ltc.

6._~olva i_e stabilisersl for examl)le, copper salts in combination with iodides and/or pllosphorus compounds and salts o~' div.llellt m;lllg;lnese.

7. 13~1slc co-st.lbilisers, for ex;lllll)le, nlel;llllille, polyvillylpylroli(lolle~ dicy~ (liullli(le, tri;lllyl Cy;lnur;llc~ llrC;l dl~riViltiVCS, lly(ll;l'~,illC deriV;lliVCS, ;IlllilleS, pOIyilllli(lCS, polyuretll;lnes, alk;lli met;ll salts al-(l alk;llille eartll met(ll s.llts of higller talty aci(ls l'or example Ca stear;lte, ~,n steilrate, Mg bellellilte~ Mg S~e;ll.lte, Na ricinole;lte all(l K
p;llmit;ltc, alltimony pyrocatccllol;ltc or i',illC pyrocatccllol.ltc~

X. Nllc!eatill.~ a~l~!s, tor cx;llllplc, ~ crl bll~yl-l)cll~oic aci(l, a(lil)ic aci(l, dil hcllyl;lcc~ic ;lc i(t.

9. I~_llers an(l r i_( rcil!g a,ell~s, for exallll)le, calcillm carbona~e, silicates, glass flbres, asbestos, talc, kaolin, mica, barilllll sul('.lte, metal oxides and hydroxy(les, carboll black, graphitc.

1(). Other a(l(lit v~ s, fOr ex;llllple, plas~icisels, lubric(lllts, emlllsifiers, pigments, optical 2 ~

brighteners, flameproofing agents, antistatic agents and blowing agents.

The compounds of the formula (I) can also be used as stabiliscrs, espccially as light stabilisers, for almost all materials known in the art of photographic reproduction and other reproduction techniques as e.g. described in Research Disclosure 1990, 31429 (page 474 to 480).

Several examples of thc prep~ration and usc of the compoullds of thc rormula (I) are reported for a more dctailed illustration of thc prcsent invcntioll; thc~c examples are given solely for illustrative purposes and do not imply any restriction.

Thc COlllpOUn(]S Or l~xalnr)lcs I, 4, 1 1, 12 ;Itld 13 arc Or p.ll~iclll;lr intcrc~t.
EXAMI'I,E 1: I`'repar;ltioll Or tl-c compoulld Or ~hc fomllll;l ,_ . .

1~3C Cl 13 I INk~ ~t C l (cl 12) ~--~ii(()C21 1s)2 1 13C (' I 13 70 g (0.165 mol) of bis(2,2,6,6-1ctr;llllctllyl-4-r)ipcri(lyl) allyllll;llol~ c, 2X.9 L~ (().215 ItlOI) of (iicthoxymcthylsil;lnc ;In(J ~4 mg Or l't( 12(1~1lCI l=-C I 12)2 ;IrC hc.l~ 01 2 h()llt S ;It )() (, ~ (l for 2 1lollr~ 12()(' ill ;l (~lo~ s ~ ol. /~ lo x()~ x( ~s~
djCII1OXYIT1C~I1YI~; jI;IIIC i:; IClllOVC(I ;I( thi.'i ICII11~('l;lllllC ill V;ICU0 (21 Illh.lr). 'I'llC rcskluc i~;
dissolve(l in 1 X() ml Or ;, 2:1 (by volulllc) (c~r;llly(lrorur;lll/ll-llcx;lllc IlliXllllC, .Illd lhe solulion is filtere(l ovcr silic;l gel. Allcr cv.lpor;ltioll of Ihc solvclll nlixlllrc in V;lelJO, ;l ligllt-colollrc(l Vi~iCOllS oil is obt;lillc(l, An;llysis lor C2()1 I~f,N2()(1Si Calclll;ltc(l: C-(~2.55(Yo; 11-1().14~Y~; N=5.()3%
I-oulld: C = (~2.24 %; 11 = 1().()4 ~; N =5.()8 %

rJxAM~ r~ ol10willg thc l)roccdllrc dcsclihc(l in l xalllplc 1, u~;illg 115 g (().255 mol) Or bis(l ,2,2,fi,~-pclll;l~ tllyl-4-pi~)cli(lyl) allyllll;lloll;l~c~ 44.5 ~ i l mol) ol di(tlloxylllclllylsil;lllc .ul(l 1()() nlg ol l)lCI2(1~1l(`11=Cl-12)2, thc conll)oLIn(l of thc formula ~l ~ t.'.~ 7 .

113C Cl-13 ~ \ C1113 11 (`--N~--~'t Cl-l--(C112)3--Si(OC21l5)2 1-~3(' C113 / 2 is prcparcd ~s a li~ht-colourc~l viscous oil.
Analysi~s r~r C3l1-l,,oN20,,Si Gllcul~lcd: C = 63.()5 'YO; 11 = 10.34 ~/,,; N = 4.79 %
F~und: C = (~.5X 'Y,; }-I = 1().29 ~/.,; N = 4.~1 %

EXAMI'EE, ~: Ptcp~ iull ol ~h(~ ~ompoul1(1 Of thc lormukl 1 13C Cl 13 \~ Cl 13 IIN~_> N C00--((112)~ i(()( 2~ )2 (,,~1 1"
I 1 ~( ( I 1.~

5().1 g (().1 f)') mol) ,r ~IIlyl N- hutyl-N-(2~2~ f~-tcll~lm~ttlyl-4 pipcri(lyl)-C~Ilh~ ltc~ 29 4 (().219 m()l) Or dicthoxylnc~llyl~ c lln(l 5() Itl~', ol 1)(( '1 ,(1>ll~ ?),~ ;11(' h('.ll(`(l 101' ?.
hollr~s ~l~ ')()"C ~Ill(l lol 2 llolll~ 17()"~' ill (1 ~10.`;('(l ~ lOl, 'I'll(` ('X~
ol 1 t-y (li~ ioll: l~oil ill~ p(~i ll l 1 72- 1 7 1"('/(). 1 Illl-.ll .
An.llysis lor C22~ ,N2(),l~i (`.ll~llhlt~(l: C' = f I .~5 '~ I ().77 '~; N = f .5() 'Yo;
l~oull(l: (' = (-().X5 ~"; 11 = I().()X '~,; N = (1.4(~ 'Y, I XAMPI,E~S 4-1(): lioll()win~ Illc prou~(llllc (Ic.~ulil-c(l in l x.ulll~lc ~ .nl(l usin~, lhc ~Ipplopri.l~ I'C.I~,(`ll~.'i, ~h(` I'ollowin~, uolllr)olln~ i .II'C ol-~.lin~

Example Formula Boiling point (C/mbar) ~ I
4 H3C--N ~ooc--(C112)10 Si(OC2H5)2 200-202/0.08 k )~ C'113 Cl ~13 ~; IINk~oo(~ (ll2--si((X211s)2 2~3-2X5/1()()0 1 13C Cl 13 >~ C113 6 IIN ~-NII--C() (C112)1() Si(oc2~ls)2 222-224/().3 A

1 13(:' Cl I

113C ( 113 7 1 IN~ ()()C (( '11,~ 'ii((X 21 15)2 195- 1 97/().()~5 II ~C (.
~ (j'l1~
X 113C-N ) N('()()((112)~--~;i(()( 2115)2 1~)()-192/().1 k C~,,(, 113C cl13 Ex.~mr)l~ l~omlula Boiling point (C/mbar) IIlC Cl1~ () ~\ ~ rcsin 9 IIN ~N (puriricd hy k ~ (C1l2)3-~i(o( 2ll5)3 chrolllatography) 1 13( Cl 13 o 11~S(' ( 113 resin >~ (puli~ied hy I lN~OO( -( '11 (( 'I ~2)~-Si(()( 2l 15) ~; ~hroma~ography) 1 13(: ( 1 13 11~('~('11~

IIN ) oo~ llZ
I1~(' ( 113 EXAM_L,l~ Prcparation Or a Inolysiloxan~ ~on~ail~ re~llltin~ 'i ol tllC r(~rlllula ~ O _ ((1 112 ~
( 11~ o~ NlI ) 13.5 ~ ((),()2411101) ol Ih(` plOdUCt 110111 EXallll-le I ale (liS.'iolVC~I ill 1()2 111l ol I N I ICI all(l ol~l~iol~ (l lol X l~o~ ,. 1()() 1lll ol (li~l~lolol~ lnc arc a(l(lc(l, all(l Ihc mix~ulc is ne;lll.lli.~;~(l wilh 1()2 ml ol I N Na()ll. Ihe Olg~llliC l~lyer is .';er)aral(`(l oll, W;l~';h('(l wi~h W,lkU, dlie(l OV('I alllly~llOll.'; N~12~ all(l ('Val)Ol'ak~(l ill VaCU().

rh~ l)lo(l~lct ol~ 32~ Illo~ llal w~i~lll ol Mll = lX()O.

EXAMI'II~ !2:I-;OIIOWitl~ )lo~ cli~ illlx~ I-lo(l~lct _ si--o-- _ _ 'l~l2)3 ~ I~<C113 t 113C Cl13 is obtailled as a light-coloured dellse oil of mOICCUI~II wcight Mn = 210().

I~XAMI'Lr 13: l~ollowing the proce(lllle de.~icrille(l ;n I~IXal11PIC 1 1 .In(l ll~ing the compolln(l Ironl l~x.nllr)le 3, a poly~ilox~lne colltaillill~, recull-illg UllitS ol the fomlula - f~l3 _ si o _ ' I~'2)3 ~C113 ()O('--N--_ kN"
C'4 l l(~ 1 13C Cl ,3 is obl(lined as ~1 light-( olollre(l dc ns( oil ol nlole~lll;lr weigll~ Mn --- 17()().

I XAMI'1,1~_14: I;ollowhl~ l.he proee(lllle (Iescl~ibe(l h~ 1 ~allll~le 11 all(l llSill~ lhe pr(~ let rrom l~xalllpl(, 4, a l~olysiloY;Ille eonl.lillillg recllrrillg nllits ol the lorn1llla -- ('11~ __ _ _-si--0-~ _ 'l~l2),(, I~ y~ s C()()--~N-( I 13 113(~ IS

EXAMPLE 15: Following the procedure described in Example 11 and using the produet from Example 5, a polysiloxane eontaining reeurring units of the formula -- Cl~3 _ si--o _ III2 I~CII3 I13C--Cll--COO (~ N 11 Il (' Cll is obtained as a light-eoloured dense oil of moleeular weight Mn = 1()()().

I;XAMT'~ ;OII()W;ng the Pl0C( d~lre descrihe(l in I~Xal11PIC t I ian(l USillg the produet frotn l~xalllpl~ f~, a polysiloxllllc colll;~ lg rccllrrillg UllitS of thc formula - C~13 _ Si O-- _ (~2~ <(113 C()N11-~ N11 _ 113C ~ I13 is obtaille(l ;IS a ligllt-eolollle(l (ICIISe oil Orn~OIcc~,l;" wei~ll, Mll 1~)()().

1~X/~MI'~ 7: POIIOW;IIg tlle PIOCC(IIIIC ~Ieseribc(l ;11 I~Xall1PIC 1 1 al1(l llS;I1g tllC l~rO(IUCt frOI11 I~Xal11l~lC 7, ;I P(1lYSilOX;II1C COIIt;l jl1 jng recllrrillL, ul1its 0I th-~ fOII1111l;1 o _ _ 'y('ll,~
(( 112)~ O(~ NII

2 ~
- 3() -is obtained as a ligh~-coloured dense oil of molecular weighl Mn = 2600.

XAMPLE l 8: Following the procedure described in Example 11 and using ~he produet from Example 8, a polysiloxane containing recurring units of the rormula C~113 _--S i O - __ ~ C113 (Cl 12)30(:)C--N ~N-CI 13 ('411') 113(' ('il:~

is oblail1ed as a light-eolouled dense oil ol moleculal weighl Mn = 2()()().

EXAMPLE 1~: Eollowing the procedure described in Example 11 and using the produet from Example ~, a polysiloxane eontaining reeuning Ul1itS of lhe fOmlula _ ~ _ [ ~ (NI1~

is ohlail1e(1 .IS a whi~e wax ol molee~llal wei;,h~ Mn = 2()()().

I X~ 11`)1,1 2(): I ollowillg lhe l roce(hlle de~iclibed in l`x.lll1ple 11 al1d USil1g Ille plo(lucl l'tol~l l,x~ oly~;ilox~ OIl~.lillit~;, I'~(,~ll'l'ill~, ~Illil~; ol' ~ l'ol lll~

01'1 ~i I ~('113 (C l 12)3--( 'f-l--CO(~ NI I

113(' (`11 i _ ~<('113 C112~ ('()()~7~NII

ainc~ a~ a li~l7l-colourc(l ~l~n~c oil ol molc~llar wci;,lll Mn - 195().

EXAMPLE 21: Prcparalion Or a poly~iloxanc containing rc~urrillg Ullit~; ol lhC lolmulae (( 112)~()()( N~NII 11 12.~) g (().():~ mol) ol lhc pro(lucl llolll l~x~lml)lc ~ (In(l 4.2 g (().()~1 nlol) ol nlclllyl(licllloxy-.~iil.ll1(~ .1l(~ (li.~;li()lvc(l ill 1()() 1lll ()I 1,2~ lclll()xyc~ c. 2.X 1lll ()1 t,'()ll(.lCIlll'.llC(i 11(, (~7 '~'., w/w) .1l(~ .1(1(l(~(1 .1ll(1 lll~ Illixl~ (141~ oolll l~rllr)~l.lllll~ I llc Illi.~t~lr~
(l wi(ll 4() 1lll ol I N N.l( )l l .1ll(1 (~v.l; or~ l ill v,l~lo (~)()C/ I .~ lr)~

rhc rc~i~Juc i~; (lix~iolvc~ 1()() ml ol (`112(`112, W.l~<ihC(I Wilh W.llCI urllil ncllll.lli~.lli()n, (l ov~l .Inlly(lloll~; N.12~$()" .111(l CV;lr~OI~ ill V~l~llO (X()C'/I.~ .lr).

A li~llt-col(-~llc(l (k n~;c oil ol Mn = 1')7() i.~i oi~l~lillc(l.

~7~

In the examples, the number-average molecular weight is determined by means of avapour pressllre osn-ometer (~Gonotcc) as described in EP-A-255,990, page 18, line 54, to page 19, line 15.

EXAMPLE 22: (light-stabilising action in polypropylene fibres): 2.5 g of each of the products indicated in Table 1, 1.0 g of a tris(2,4-di-t-b-ltylphenyl) phosphite, 0 5 g of calcium monoethyl 3,5-di-t-butyl-4-hydroxybenzylphosphonate, 1 g of calcium steilrate and 2.5 g of titanium dioxidc are mixed in a slow n-ixer with 1()()0 g of polypropylene powder of melt index = 12 g/10 minutes (mca~ rcd at 23()C alld 2.16 kg).

The mixtures are extruded at 20()-23()C to ~ivc polymcr ~ranulcs which are thenconvcrtcd inlo rlhrcs usin~ a pilot-lypc app;lr;ltlls (~I,col1ilr(1-SIllllira~o (VA), Iklly) at1d opcratin~ nll(lcr thc lollowin~ con(litiolls:

Ex~ruder telnpcrilturc: 200-230C
13cad temperature: 255-26()C
Stretch ratio: 1:3.5 Count: 11 d~cx pcr rllall1ent l hc fibres thus prcl);lrcd arc exposcll, nloullte(l on a whitc carcl, in a model 65 WR
Wcathcr-O-Mcter (AS I M l ~ 25(5-XS) with a black pancl tcmpcraturc of 63C.

'I hc reSidU;II tCll;lCity i:i IllCa'i~ll'ed 011 S;llllplC.'i tilkC.II ill'tCI' Vill'iOllS ~illlCS ol' CX~ ;llre tO ~
by me;llls or a const;llll-spcc(l lcllsOluctcl, ;111(l IhC CXpO~;lll'C lilllC ill h0111'S (rl~ ) nec~lc~l to ll,llvc tll~ illiti,ll t~ll;l~ity i~ tllcll ~ lll;lt~(l l~ibrcs prcp.lrc(l ulldcr thc silnlc col1(litil)lls as in(lieiltcd al)ovc~ bllt withoul a(llJilioll Or IllC
COlllpOlllll.lS ol- lhC illVCll~iOIl, .II'C CXI)o.`;C(l rOr COlllp~lriSOIl.

I hc rcslllls obt;lillc(l arc ShO\VIl ill 'I';lhlC 1:

Table I
Stahiliser Ts(~ (hours) None 150 Compound from Example 1 1 1350 Compound from Example 12 I 120 Compound from Example 13 1330 _XAMPLE 23: (lighl-stabilising action in polypropylene taitc~s):
1 g of each ol the compounds indicated in Table 2, 1.0 g of tris-(2,4-di- t-butyl-phenyl) phosphite, 0.5 g of pentacrythritol tctrakis-l3-(3,5-di-t-butyl-4-hydroxyphenyl)-propionatcl an(l I g of calcium s~calale alc IlliXCd in a ~slow IlliXCI with 1()0() g Or p()ly-plpylcllc p~wdcr ol mcll in(l(x -- 2g/l() mil1lllc~s (mc~l~sulc(l al 2~()C lllld 2.16kg).

Thc mixturcs are extrudcd at 2()()-2'~()C to givc p olymer granulcs which are ~hen converted into stretched lapes Or 50 ilm thickness and 2.5 mm widlh, using a pilot-type apparalus ((~)Leonard-Sumirago (VA), Ilaly) op~raling under Ihc lollowin~ con~litions:

Exlrudcr lemperal~lre: 21()-2~()(' lleacl Iemi cl.lll.lre: 24()-2()()C
Slrclch ralio: 1:6 Thc lapc~s IhU~S p rcpalC~l are cx, oxc(i, mounlc~l 011 a whilc CIII(I~ in a mo(lcl ()5 Wl~
Wealll( r-()-Melcr (AS I M 1} 2.5~iS-XS) willl ;l hl.l( k p.lll( I lcnlllclal(llc ol (~C.

l hc rc~sidual lcnacily i~s mealiuled On xillnl~lcx lilkull al lcr VIU ioux lhl1e~s ol exp()s~lrc lo lighl lly mealls ol a con~skltll-~s~necd Icn~sol11elcl; lhc CXi10XlllC lilllc (in hollrs) ( 1'5()) needcd lo Tllpc~s p rci arcd un(l~l lh~ xiunc con(lilionx as indicalcd ahov(, hul willloul addilion Or ~slahiliscr, arc cx, o~sc(l I'or ~olnpalixon~

2~3 7~
- ~4 -Tablc 2 Stabiliscr Tso (hours) None 300 Compound of Examplc l 1 3200 Compound Or Example 12 3 I X0 EXAMPLE 24: (light-~stabili~sing aclion in polyl-ropylene pla~lues):
1 g of each Or thc compounds indicalcd in Tablc 3, 1.0 g of ~ris-(2,4-di-t-butylphcnyl)-phosphi~c, 0.5 g of pcnlacrylhrilol lclraki~s-13-(3,5-(li-l-bulyl-4-hy(ll()xy-phetlyl)-plopion.llel, I g ol 131ue Phlhalocycltlitle all(l 1 g Or CalCiUIll ~;learate arc mixcd in a ,<;IOW IlliXCI- wilh 1()()() ~ ol polyplopylelle pow(lel Ol IllCI~ illdCX = 2.1 g/lO minutcs (mcasure(l al 23()C .In(J 2 16 kg).

Thc mixlurcs are cxtrudcd a~ 200-220C lo givc polyMer plaqucs of 2 mm lhickness by in jcc~ion-moulding al 1 9()-230C.

'1'11C r)la(lUCS alC ll1Cn CXP()~;C(I in a Weather-()-Me~er 65 WR (I~Sl`M G 26-77) wilh a hlack p.lllel Iemperalure ol (~3C unlil llle St~ ol superlicial embrittlcmenl (chalking).

For comr)arisoll~ a polypropylcnc pla(luc prcl-alc(l Ull(lCI- Ihc ~SIIIllC C()ll(~ as ill(li(;;llc(l VC, 1~1 WiII1O~II lI1C .I(I(I;I;OI1 0~ 1II(~ ~OII1I)()IIII(I~ 01 1I1(~ ;I1V~ XI)O~

'r~ 'illOW~'; lI1C CXr)O~ O~II~) 1-~(I(I;I-~(I 10 rC~ICI~ C ~ 1 01 ~ CIIiCi~II
clllhri~lcmclll.

1 '1l?l(' ~ - - -Sl.lhiliselEl~ lelllelll time (hn~) Nonc S()() Coml-oul1d ol Example 135(j() C`onlr)oull(J ol Examl-le4 3')X0

Claims (18)

1. A compound of the formula (I) (I) in which A is one of the groups of the formulae (IIa)-(IId) , , (IIa) (IIb) , (IIc) (IId) in which R4 is hydrogen, C1- C8alkyl, O-,OH,NO,CH2CN,C1-C18alkoxy, C5-C12cyclo-alkoxy, C3-C6alkenyl, C7-C9phenylalkyl which is unsubstituted or mono-, di- or tri-substi-tuted on the phenyl by C1-C4alkyl; or C1-C8acyl, X3 is -O- or >N-R12 where R12 is hydrogen, C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C1-C4alkyl; C7-C9phenylalky which is unsubstituted or mono-, di- or tri-substituted on the phenyl by C1-C4alkyl; or tetrahydrofurfuryl, C2-C4alkyl substituted in the 2-, 3- or 4-position by C1-C8alkoxy, by di-(C1-C4alkyl)-amino or by a group of the formulas (III) (III) where X4 is a direct bond, -O-, -CH2-, -CH2CH2-, or H3C-N<, or R12 is a group of the formula (IV), (IV) with R4 as defined above, or R12 is one of the groups of the formulae (Va)-(Vd) , , (Va) (Vb) , (Vc) (Vd) where R4 is as defined above, X5 is -O- or >N-CH3 and X6 is -CH2CH2-, -CO-, -COCO-or -COCH2CO-, or X3 is a 1,4-piperazinediyl group, p is 1, 2 or 3 and, when p is 1, R5 is C2-C18alkanediyl and, when p is 2, R5 is C2-C20alkanetriyl, C5-C7cycloalkanetriyl or C7-C9bicycloalkanetriyl or a group wher X7 is -O- or >N-R14 with R14 being C1-C8acyl or (C1-C8alkoxy)-carbonyl, R13 is C3-C12alkanediyl and q is 0 or 1, and, when p is 3, R5 is C3-C6alkanetetrayl, R6 is as defined above for R12, R7 is C2-C12alkanediyl, R8 is hydrogen or methyl, R9 is a direct bond, C1-C18alkanediyl or a group -X7-R13- with X7and R13 as defined above, R10 is hydrogen or methyl and R11 is -CH2- or -CH2CH2-, R1 is C1-C8alkyl, phenyl, C1-C8alkoxy or OH, R2 and R3 which are identical or different are C1-C8alkyl or phenyl, or R2 is also hydrogen, m + n is a number from 1 to 100, n varies from zero to 90 % of the sum of m + n, X1 is as defined for R1 or is a group (R15)3SiO- with R15 being C1-C8alkyl or phenyl, X2 is hydrogen, C1-C8alkyl, a group (R15)3Si- or, when R1 and X1 are C1-C8alkyl or phenyl, X2 is additionally a group , and, when m + n is a number from 3 to 10, X1 and X2 together also form a direct bond; each of the groups R1, R2, R3 and A have the same definition or different definitions in the recurring structural units contained in formula (I) and, when the compounds of the formula (I) are copolymeric, they have a random distribution or a block distribution of the individual structural units.

2. A compound of the formula (I) according to claim 1, in which R4 is hydrogen, Cl-C4alkyl, OH, C6-C12alkoxy, C5-C8cycloalkoxy, allyl, benzyl or acetyl.

3. A compound of the formula (I) according to claim 1, in which A is one of the groups of the formulae (IIa)-(IId) in which X3 is -O- or >N-R12 where R12 is hydrogen, C1-C12alkyl, C5-C8cycloalkyl which is unsubstituted or mono-, di- or tri-substituted by C1-C4alkyl;
benzyl which is unsubstituted or mono-, di- or tri-substituted by C1-C4alkyl; tetrahydro-furfuryl, C2-C3alkyl substituted in the 2- or 3-position by C1-C4alkoxy, by di-(C1-C4-alkyl)-amino or by a 1-pyrrolidyl, 1-piperidyl or 4-morpholinyl group, or R12 is a group of the formula (IV) or one of the groups of the formulae (Va)-(Vd) in which X5 is -O- or >N-CH3 and X6 is -CH2CH2-, -CO- or -COCO-, or X3 is a 1,4-piperezinediyl group, p is 1, 2 or 3 and, when p is 1, R5 is C2-C12alkanediyl and, when p is 2, R5 is C2-C16,alkane-triyl, C6-C7cycloalkanetriyl, C7-C9bicycloalkanetriyl or a group where X7 is -O- or >N-R14 with R14 being C1-C6acyl or (C1-C6alkoxy)-carbonyl, R13 is C3-C11-alkanediyl and q is zero or 1, and, when p is 3, R5 is C3-C4alkanetetrayl, R6 is as defined above for R12, R7 is C2-C11alkanediyl, R8 is hydrogen or methyl, R9 is a direct bond, C1-C12alkanediyl or a group -X7-R13- with X7 and R13 as defined above; R10 is hydrogen or methyl and R11 is -CH2-, R1 is C1-C6alkyl, phenyl, C1-C6alkoxy or OH, R2 and R3 which are identical or different are C1-C6alkyl or phenyl or R2 is also hydrogen, m + n is a number from 1 to 80 and n varies from zero to 90 % of the sum m + n, X1 is as defined for R1 or is a group (R15)3SiO- with R15 being C1-C6alkyl, X2 is hydrogen, C1-C6alkyl, a group (R15)3Si- or, when R1 and X1 are C1-C6alkyl or phenyl, X2 is additionally a group , and, when m + n is a number from 3 to 10, X2 together also form a direct bond.

4. A compound of the formula (I) according to claim 1, in which A is one of the groups of the formulae (IIa)-(IId) in which X3 is -O- or >N-R12 where R12 is hydrogen, C1-C10alkyl, cyclohexyl which is unsubstituted or mono-, di- or trisubstituted by C1-C4alkyl; benzyl, tetrahydrofurfuryl, C2-C3alkyl substituted in the 2- or 3-position by methoxy, by ethoxy, by dimethylamino, by diethylamino or by 4-morpholinyl, or R12 is a group of the formula (IV) or one of the groups of the formulae (Va)-(Vd) in which X5 is -O- or >N-CH3 and X6 is -CH2CH2- or -CO-, or X3 is a 1,4-piperazinediyl group, p is 1, 2 or 3 and, when p is 1, R5 is C2-C10alkanediyl and, when p is 2, R5 is C2-C14alkanetriyl, cyclohexanetriyl or bicycloheptanetriyl or a group where R7 is -O- or >N-R14 with R14 being C1-C4acyl or (C1-C4alkoxy)-carbonyl, R13 is trimethylene and q is zero or 1, and, when p is 3, R5 is propanetetralyl, R6 is as defined above for R12, R7 is C2-C11alkanediyl, R8 is hydrogen or methyl, R9 is a direct bond, C1-C12alkanediyl or a group -X7-R13- with X7 and R13 being as defined above, R10 is hydrogen or methyl and R11 is -CH2-, R1 is C1-C4alkyl, phenyl, C1-C4alkoxy or OH, R2 and R3 which are identical or different are C1-C4alkyl or phenyl, or R2 is also hydrogen, m + n is a number from 1 to 60 and n varies from zero to 90 % of the sum m + n, X1 is as defined for R1 or is a group (R15)3SiO- with R15 being C1-C4alkyl, X2 is hydrogen, C1-C4alkyl, a group (R15)3Si- or, when R1 and X1 are C1-C4alkyl or phenyl, X2 is additionally a group and, when m + n is a number from 3 to 10, X1 and X2 together also form a direct bond.

5 A compound of the formula (I) according to claim 1, in which A is a group of the folmula (IIa) or (IIb) in which X3 is -O- or >N-R12 where R12 is hydrogen, C1-C8alkyl, cyclohexyl, benxyl, tetrahydrofurfuryl, a group of the formla (IV) or a group of the formula (Va) or (Vb) in which X5 is -O- or >N-CH3 and X6 is -CH2CH2- or X3 is a 1,4-piperazinediyl group, p is 1 or 2 and, when p is 1, R5 is C2-C10alkanediyl and, when p is 2, R5 is C2-C14alkanetriyl, R6 is as defined above for R12, R7 is C2-C4alkanediyl, R4 is C1-C3alkyl, C1-C3alkoxy or OH, R2 and R3 are C1-C3alkyl or R2 is also hydrogen, m + n is a number from 1 to 50 and n varies from zero to 75 % of the sum m + n, X1 is as defined for R1 or is a group (R15)3SiO- with R15 being C1-C3alkyl, X2 is hydrogen, C1-C3alkyl, a group (R15)3Si- or, when R1 and X1 arc C1-C3alkyl, X2 is additionally a group , and, when m + n is a member from 3 to 10, X1 and X2 together also form a direct bond.

6. A compound of the formula (I) according to claim 1, in which A is a group of the formula (IIa) or (IIb) in which R4 is hydrogen or methyl, X3 is -O- or -NH-, p is 1 or 2, and when p is 1, R5 is C2-C10alkanediyl and, when p is 2, R5 is C2-C14alkanetriyl, R6 is hydrogen, C1-C4alkyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl and R7 is trimethylene, R1 is methyl, methoxy, ethoxy or OH, R2 and R3 are methyl, m + n is a number from 1 to 40, n varies from zero to 50 % of the sum m + n, X
is as defined for R1 or is a group (CH3)3SiO- and X2 is hydrogen, methyl, ethyl, a group (CH3)3Si- or, when R1 and X1 are methyl, X2 is additionally a group , and, when m + n is a number from 3 to 10, X1 and X2 together also form a direct bond.

7. A compound of the formula (I) according to claim 1, in which A is a group of the formula where R4 is hydrogen or methyl, X3 is -O- or -NH- and R5' is ethylene, propylene or decamethylene.

8. A compound of the formula (I) according to claim 1, which A is a group of the formula where R4 is hydrogen or methyl, X3 is -O- or -NH- and R5" is a group -CH2-CH< or >CH-(CH2)3-.

9. A compound of the formula (T) according to claim 1, in which A is a group of the formula where R4 is hydrogen or methyl and R6 is hydrogen or C1-C4alkyl.

10. A compound of the formula (I) according to claim 1, in which A is a group of the formulae (IIa), (IIb) or (IIc) in which R4 is hydrogen or methyl, X3 is -O- or >N-R12 where R12 is hydrogen or C1-C4alkyl, p is 1 or 2 and, when p is 1, R5 is C2-C10alkanediyl and, when p is 2, R5 is C2-C14alkanetriyl, R6 is as defined above for R12, R7 is C2-C4alkane-diyl, R8 is hydrogen or methyl, R9 is C1-C12alkanediyl, R1 is C1-C3alkyl, C1-C3alkoxy or OH, R2 and R3 are C1-C3alkyl or R2 is also hydrogen, m + n is a number from 1 to 50 and n varies from zero to 75 % of the sum m + n, X1 is as defined for R1 or is a group (R14)3SiO- with R15 being C1-C3alkyl, X2 is hydrogen, C1-C3alkyl, a group (R15)3Si- or, when R1 and X1 are C1-C3alkyl, X2 is additionally a group , and when m + n is a number from 3 to 10, X1 and X2 together also form a direct bond.

11. A compound according to claim 1, which is or

12. A compound of the formula (I) according lo claim 1, in which n is zero and the repeating structural unit of the formula corresponds to , or .

13. A composition comprising an organic material susceptible to degradation induced by light heat and oxidation and at least one compound of the formula (I) according to claim 1.

14. A composition according to claim 13,wherein the organic material is a synthetic polymer.

15. A composition according to claim 14,which contains other conventional additives for synthetic polymers in addition to the compounds of the formula (1).

16. A composition according to claim 13,in which the organic material is a polyolefin.

17. A composition according to claim 13,in which the organic material is polyethylene or polypropylene.

18. A method for stabilizing an organic material against degradation induced by light heat and oxidation which comprises incorporating into said organic material at least one compound of the formula (I) according to claim 1.

FD 4.2/SR/hdr*