MXPA99003986A - Functionalised polymers - Google Patents

Abstract

This invention relates to a process for stabilising and at the same time phase compatibilising plastics or plastic compositions by incorporating polymeric compounds obtainable by reacting a compound selected from the group consisting of the sterically hindered phenols, sterically hindered amines, lactones, sulfides, phosphites, benzotriazoles, benzophenones and 2-(2-hydroxyphenyl)-1,3, 5-triazines, which compounds contain at least one reactive group, with a compatibilisator.

Description

FUNCIOMAI-IZADOS POLYMERS The present invention relates to the establishment of plastics and plastic compositions ° (virgin or recycled materials, optionally combined with virgin materials) and at the same time to the improvement of mechanical properties by the incorporation of specific compatibilizers. The preparation of polymer blends is an established method for producing plastics that have novel properties. As is known, however, polymers of different structures usually can not be combined with others, that is, the processing of two different plastics gives a macroscopic mixture having insufficient mechanical properties. To improve the compatibility and therefore also the properties of the plastic combinations, so-called compatibilizers are commercially available. These co-catalysts are polymers, which prevent or reduce the separation of -y systems of two or multiple components or that improve dispersion, producing therefore a homogeneous mixture of different plastics with good mechanical properties. Known compatibilizers are based predominantly on polymers of polar and non-polar structures, which are I > produced by customary polymerization reactions- The compatibilizers are used in virgin plastic compositions and also, increasingly, in recycled. In this case, the production process, or the collection of plastics used, often results in plastic compositions, the mechanical properties of which are only suitable for new applications if campaigners are added to them. In Kunststoffe 83 (1993) r 10, 820-822 and in Kunststoffe 85 (1995) 4, 446, 450, K. Hausmann discusses the problem of recycling incompatible plastics, such as polyethylene / polyethylene terephthalate (PE / PET) and polyamide / polyethylene (PA / PE). For recycling, compatibilizers are used. In Kunststo - re 83 (1993) 5, 369-3T2 R.-Grützner, R. Gártner and H.-G. Hock, published research on similar systems (composite sheets of (PE / PA) R. Mühlhaupt and J. Rósch report phase compatibilizers for polypropylene / polyamide alloys (PP / PA) in iC-mststo-T-fe 84 (1994 9) 1153-1158. In -O --- ststo-í? E 83 (1993) 11, 926-929, G. Obieglo y. Romer also describes compatibilizers to be used in plastic recycling. In Recycle, 91, 8 / 5-1 and Recycle 95, 6 / 4-3, S. Fuzessery present compatibilizers and polymeric modifiers for virgin and recycled thermoplastics. It is known how to join stabilizers to a polymer to obtain a better combination in the product to be established and prevent the migration of the stabilizers thereof. This has been suggested, inter alia, by M. Minaga a in Polymer Degradation and Stabili ty 25 (1989), 121-141 or by H. Yamaguchi, M. Itoh, H. Ishikawa and K. Kasuda in J. M. S. -Puré Appl. Chem., A30 (4), (1993), 287-292. In Die Angewandte Makromolekulare Chemie 158/159 (1998), 221-231, in ñdvances in Polymer Science 101, pages 65-167, Springer-Verlag Berlin Heidelberg, 1991 and in Jan Posplsíl, Peter P. Klemchuck, Oxidation Inhibition in Organic Materials , Vol. 1 (1989), 193-224, Jan Pospisil presents a study of "functionalized polymers", ie polymers containing an antioxidant, antiozonant, metal deactivator, photostabilizer or effective biostabilizer EP-A 306 729 describes the union from antioxidants to polymers, the polymers are obtained by reacting a polymer with anhydride functionalities, with an antioxidant with hydrazide functionalities or with a copolymer consisting of N-substituted imides of α, β-unsaturated cyclic dicarboxylic anhydrides (with antioxidant function) and ethylenic or vinyl aromatic monomers The stabilization of plastic compositions against heat and light has a special problem because, depending on the polarity of the components, a non-uniform distribution of the compounds is obtained. stabilizers in the polyphase polymer system (distribution of the stabilizer). This is described, inter alia, in D.M. Kulich, M.D. olko icz and J.C. ozny in Makromol. Chem., Macromol. Symp. 70/71, 407-418 (1993). The distribution balance of the stabilizers is further influenced by the compatibilizers used, which are, moreover, often the least stable component of the composition. The thermal or photo-oxidative damage of the compatibilizers therefore results in a very rapid breakage of the entire composition due to the damage of the compatibilizing component. Accordingly, it is desirable to provide compounds that improve the compatibility of the components in polymer combinations, as well as the mechanical properties and that also ensure protection against oxidative and photooxidative damage. It has now been found that the specific polymers corresponding to the stabilizing side groups possess those properties. Accordingly, this invention relates to a process for establishing and at the same time plastics or plastic compositions that compatibilize the phase by incorporating polymeric compounds obtainable by the reaction of compounds selected from the group consisting of sterically hindered phenols, sterically hindered amines, lactones, sulfides, phosphites, benzotriazoles, benzophenones and 2- (2-hydroxyphenyl) -1,3,5-triazines, compounds which contain at least one functional reactive group, with a compatibilizer. Suitable sterically hindered? -ols containing at least one reactive group and reacting with the compatibilizing compound are the compounds of formula I Ri and R2 are each independently of the other, hydrogen, C?-C25 alkyl, phenyl-C1-C3 alkyl, which is unsubstituted or substituted once or several times in e-1 aromatic ring by OH and / or C1-C4 alkyl, unsubstituted or C1-C alkyl < -substituted C5-C-2cycloalkyl, or phenyl; n is 1, 2, or 3 E is OH, SH, NHR3, S03H, COOH, 4 m is 0 or 1; R3 is hydrogen or C1-C9 alkyl, Rj is C? -C_2 alkyl, or phenyl, which is unsubstituted or substituted by one or more Ci-Q alkyl, halogen and / or C? -C18 alkoxy; A, if E is OH, SH or -CH = CH2, is -C-Ha-, -CH2-S-CH2CH2-, CqH2 < J- (CO) -0-C "H2p-, CqH2q- (CO) -NH-CpH2p- or -C, H2q- (CO) -0-C-H2p-S - ?, H2 - x is a number from 0 to 8 p is a number from 2 to 8; q is a number from 0 to 3; Ri and n are as defined above; or A, if E is -NHR3, is -CxH2j! - or CqH2q- (CO) -NH-CpH2p, where x, p and q have the meanings cited above; or A, if E is COOH or S03H, is -Cx-K2x, -CH2-S-CH2- or CH2S-CH2CH2-, where x has the meaning cited above; or O / \ A, if E is (CH2) m-CH-CH2, it is a direct bond, CqH2q- (CO) m-0- CH2- or -C? H2x-S-CH2-, where q, m , x, Ri and R2 are as defined above; A, if E is is -CH2- The alkyl of C? -C25 is linear or branched and is typically C? -C20 alkyl, Ci? Ci? -, C? -C? _-, C? -C9-, C? -Ce- or C? -C4 alkyl. Typical examples are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, ter- butyl, pentyl, 1,1-dimethylpropyl, hexyl, heptyl, 2,4,4-trimethyl-pentyl, 2-ethylhexyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosilo, docosilo or pentacosilo. C 1 -C 9 alkyl and C 1 -C alkyl have, for example, the meanings mentioned above up to the corresponding number of carbon atoms. The C2-Cs alkenyl radicals may be mono- or polyunsaturated and are typically allyl, methallyl, 1,1-dimethylallyl, 1-butenyl, 3-butenyl, 2-butenyl, 1,3-pentadienyl or 5-hexenyl. Preferred is the allyl-R3 defined as C2-C6 alkenyl is, for example, C2-C4 alkenyl. C 1 -C 4 alkoxy is a straight or branched radical and is methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, sec-butyloxy, iso-butyloxy or tert-butyloxy. E_T phenyl-C 1 -C 3 alkyl is typically benzyl, phenylethyl, α-methylbenzyl or α, o-dimethyl-benzyl. Benzyl is the preferred one. The cycloalkyl of Cs-C ?2 is typically cyclopentyl, cyclohexyl, cyclooctyl, cyclododecyl, in particular cyclopentyl and cyclohexyl, preferably cyclohexyl. The C?-C? 2 substituted C?-C-cycloalkyl alkyl is typically 1-methylcyclohexyl ^ The halogen is fluorine, chlorine, bromine and iodine, in particular chlorine and bromine, preferably chlorine. The mono- or polysubstituted phenyl is typically substituted from one to five times, for example one, two or three times, preferably one or three times, on the phenyl ring. The substituted phenyl is substituted, for example, by Linear or branched C 4 -C 4, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl, or by linear or branched C 1 -C 4 alkoxy, such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy or t-butoxy, or by halogen, such as fluorine, chlorine, bromine or iodine. The phenyl is preferably substituted by, in particular, methyl, t-butyl, methoxy, and chloro. Suitable compounds are those of formula I, wherein Ri and R 2 are C 1 -C 4 alkyl. Other compounds to be mentioned are those of formula I, where Ri and R2 are in the position ortho to the phenolic OH group. Particularly suitable compounds are those wherein A is -C ^ -H ^ -, typically 6-tert-butyl-2,4-d-methyl-3-hydroxymethylphenol, 2,6-di-tert-butyl-4- (3 -hydroxypropyl) phenol or 2,6-di-tert-butyl-4- (2,2-dimethyl-3-hydroxypropyl) phenol. x is typically a number from 0 to 6, preferably from 0 to 4. Those compounds of formula i which also deserve to be mentioned, wherein A is a group -0H2 -? - 0H2 or -CH2-S-CH2CH2-, typically 2,6-di-tert-butyl-4-. { 4-hydroxy-2-t.iabut-1-yl) phenol or 6-tert-butyl-2,4-dimethyl-3- (4-hydroxy-2-thiabut-1-yl) phenol. Other important compounds of formula I are those, wherein A is CqH2q- (CO) -0-CpH2p-, p is a number from 2 to 5, and q is from 1 to 2, such as Other suitable compounds CH2) 20H H ° -V_V- (CH.) I-C-NH-CH.CHJ H- , 2,6-di-tert-butyl-4- (3-ammopropyl) phenol, 2,6-di-tert-butyl-4- (2,2-dimethyl-2-amino-ethyl) phenol or 2 , 4, 6-trimet? L-3-aminomethylphenol. If E is COOH, x is preferably 2 6 3.

Preferred compounds are, for example, 2,6-di-tert-butyl-4- (2-carboxyethyl) phenol, 2-tert-butyl-6-methyl-4- (2-carboxyethyl) phenol and 2,6- di-tert-butyl-4- (3-carboxy-2-thiaprop-1-yl) -phenol. OR II If E is -P-R4, R4 is, for example, C1-C4 alkyl I OH preferably methyl ethyl, such Particularly preferred examples of compounds of formula I with epoxy function, are CH2-CH? -CH2 x is as defined above. Examples of particularly preferred compounds of formula I with OH-, SH- or NHR3 function are wherein x is a number from 1 to 8. The preparation of sterically hindered phenols is known to those skilled in the art and is described, inter alia, in DE-A-42 13 750, DE-A-25 12 895, EP -A-463 835, US 5 189 088, DE-A-24 14 417, US 4 919 684, DE-A-42 42 916, DE-A-20 37 965 and in numerous other publications.

Some sterically hindered amines, which contain at least one reactive group and which react with the compatibilizing compound, are the compounds of formulas II, lia or Ilb, (IIb), wherein Ra is hydrogen, Ci-C? Alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C1-C20 alkoxy, phenyl-Ca-C3 alkyl, C5-C12 cycloalkyl, C-C8 cycloalkoxy, phenyl, naphthyl, hydroxyethyl, CO-C25 alkyl, CO-phenyl, CO-naphthyl, CO-phenyl-alkyl of C -? - C3, O-CO-C1- alkyl C20 or C C-C6 alkyl-S-C?-C6 alkyl, Ca-C6-0 alkyl-C?-C6 alkyl, alkyl O / deC? -C6- (CO) -Ci-Cß alkyl, -CH 2 -CH 2-0-CH 2 -CH-CH 2 O / -CH 2 -CH-CH 2; w is a number from 1 to 10; And it is a simple bond, alkylene of C? -C25, phenylene, biphenylene, naphthylene, -O-C 25 alkylene-alkylene; OR R9 is hydrogen or C? -C? 2 alkyl; Rio has the same definition as Rs. The alkyl of C C-C25, phenyl-alkyl of Cj-C3 and cycloalkyl of Csci2 have, for example, the meanings given above for formula I. The C1-C12 alkyl also has those meanings up to the corresponding number of carbon atoms. The C? -C25 alkylene is linear or branched, such as methylene, ethylene, propylene, isopropylene, n-butylene, sec-butylene, iso-butylene, tert-butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene , dodecylene, tetradecylene, heptadecylene or octadecylene. Y is - in particular C 1 -C 12 alkylene, for example C 1 -C 1 alkylene, preferably C 1 -C 4 alkylene .. Particularly preferred examples of compounds of formula II with epoxy function are , also, wherein R_ is C? -C? 2 alkyl. Particularly preferred examples of compounds of formula II with OH- or NH 2 function are wherein R9 is C1-C12 alkyl. Those skilled in the art are familiar with the preparation of hindered-mine compounds. sterically, which is described, inter alia, in EP-A-634 450, EP-A634 449, EP-A-434 608, EP-A-389 419, EP-A-0 634 399, EP-A-0 001 835 or by Luston and Vass, Makromolekulare Chemie, Macromol,? Ymp. 27, 231 (1989) and other publications. Suitable lactones containing at least one reactive group and reacting with the compatibilizing compound are the compounds of formula III - Rn, R12, Ri2"and R13 are each independently of the other, hydrogen, C1-C25 alkyl, phenylC1-C3 alkyl, C5-C2 cycloalkyl or phenyl; and O / \ G is OH, O-CH2-CH-CH2, -OCH2CH2OH or -OC? 2COOH. The meanings of C 1 -C 12 alkyl, C 1 -C 12 alkyl, phenyl C 1 -C 3 alkyl, C 1 -C 2 cycloalkyl and C 1 -C 25 alkylene, correspond to those given for formulas I, II and lia.

Preferred compounds are those of formula III, wherein G is an OH radical.

Particularly suitable compounds of formula III are those in which Rn, RJ2, 12 and R13 are hydrogen, C1-C10 alkyl, phenyl-C1-C3 alkyl or cyclohexyl. _ R11, R12, R12-. and 13 are preferably Ci-C4 alkyl, in particular methyl and tert-butyl. Preferred examples of compounds of formula III are, for example, It is also possible to use mixtures of isomeric position compounds. The preparation of suitable lactones is known to those skilled in the art and is described, inter alia, in EP-A-591 102 and other publications. Suitable sulfides containing at least one reactive group and which are reacted with the compatibilizing compound are the compounds of formula IV. Rjs-S-Rio (IV), where - s Ris is C? -C-β alkyl. benzyl, phenyl or -11r (0R? 7) 2; Y 0 /? R? 6 is -CH2CH20H, -CH2-CH-CH2, -CH2C00H or -CH2CH2C00H; and Rp is unsubstituted or unsubstituted C? -C? or C? -C4 alkyl-phenyl alkyl. The meanings of alkyl-of C? -C? And of alkyl of C 1 -C 4 -substituted phenyl are the same as those given above for formula I. R 5 is preferably C 8 -C 2 alkyl, benzyl or phenyl, in particular C 1 -C 2 alkyl. Ris is preferably 0 / \ -CHCH20H or -CH2-CH-CH2. Typical examples are O / CCiHi7-S-CH2-CH-CH2 or C? 2H25-S-CH2CH2? H. Also suitable are compounds of formula IV, S II where Ris is -P- (0Rn) 2, preferably (H7C3?) 2- The preparation of suitable sulfides is known to those skilled in the art and is described, inter alia, in Abh. Akad. Wiss. DDR Abt. Math., Natur iss. , Tech. (1987), Vol. Oct. 1986 - (ID), 511-5; EP-A-166 6"95, EP-A-413 562 and other publications.

Suitable phosphites containing at least one reactive group and which are reacted with the compatibilizing compound are the compounds of formula V.

Or R16-P- (ORpay? (V), where ee is -CH2CH20H or -CH2CH2COOH; and Ri7"is unsubstituted or unsubstituted C? -C? Alkyl or substituted C1-C4-alkyl. The meanings of C? -C_ alkyl and substituted C?-C 4 alkyl phenyl are the same as those given above for formula I. Particularly suitable phosphites are those O O II II of formula (C2H50) 2-P-CH2CH20H, (C2H50) 2-P-CH2CH2COOH, OO "II / \ and (C2H50) 2-P-CH2-CH-CH2 Those skilled in the art are familiar with the preparation of suitable phosphites which are described, inter alia, in Khim.-Famy. Zh. (1988). ), 22 (2), 170-4 and other publications The benzotriazoles, benzophenones and suitable 2- (2-hydroxyphenyl) -1,3,5-triazines containing at least one reactive group and which are reacted with the compatibilizer compound, are the compounds of formulas VI, Via, VIb or VIc Ria is - (CH2) t-R2o, -O-CH2-CH-CH2 or NH2; R? 9 is C? -C? 2 alkyl, a-a-dimethylbenzyl or a radical H-CH2 or - (C0) -NH- (CH2) u-NC0; O 1 CH ^ 'CH / \ H2 R21 is hydrogen, or -CH2-CH (OH) -CH2-: 0- (CO) -R22; R 22 is C 1 -C 4 alkyl or phenyl; R2 and 2- are each tino independently of the other, hydrogen or C? -C4 alkyl; O / \ - CH2-CH-CH2 R25 is hydrogen, - (CH2) u-0H,, (CH2) uCOOH or - (CO) - R26 is hydrogen, OH or C1-C12 alkoxy; R27 is hydrogen or OH; R2a is hydrogen or R29 is hydrogen or halogen; R3o is hydrogen or C? -C9 alkyl; m is 0 or 1; t is a number from 0 to 6; u is a number from 2 to 12. The alkyl of Ca-C4 is typically linear or branched and is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl. Methyl is the preferred one. Particularly suitable compounds are, for example, hydroxy-substituted benzophenones such as These compounds can also be substituted in the aromatic rings, for example with additional hydroxyl groups or alkoxy. The benzotriazoles of formula They are also suitable. In addition to the functionalized epoxy radical, the hydroxyphenyl group may also contain alkyl substituents. Particularly suitable triazine compounds are, for example, those of formula wherein the phenyl groups can be further substituted by methyl. The preparation of benzotriazoles is known to those skilled in the art and is described, inter alia, in EP-A-693 483; Polymer (1995), 36 (17), 3401-8 and other publications. The preparation of suitable 2- (2-hydroxyphenyl) -1,3,5-triazines is known to those skilled in the art and is described, inter alia, in EP-A-434 608; CA-A-2062217 and other publications. The Preparation of suitable benzophenones is known to those skilled in the art and is described, inter alia, in EP-A-693 483; EP-A-538 839; Zh. Prikl. Khim. (Leningrad) (1976), 49 (5), 1129-34; JP-A-Hei 3 31235 (= Chemical Abstract No. 115: 49102) and other publications. This invention also relates to compounds, which can be obtained by reacting sterically hindered phenols of formula I (I), in which i and R2 are each independently of the other, hydrogen, C1-C25 alkyl, phenylC1-C3 alkyl, which is unsubstituted or substituted once or several times in the aromatic ring by OH and / or C-alkyl; ? -C4, unsubstituted or substituted C? -C4-cycloalkyl of C3-C? 2 or -Eeni lo; n is 1, 2 or 3; E is OH, SH, NHR3, S03H, COOH,; m is O or 1; R3 is hydrogen or Cj.-C9 alkyl, R4 is C1-C12 alkyl, phenyl which is unsubstituted or substituted by one of several C1-C4 alkyls, halogen and / or Ci-Ciß alkoxy; A, if E is OH, SH or -CH = 0H2, is -CA, -, -CH2-S-CH2CH2-, CqH2q (CO) -0-CpH2p-, CqH2q- (CO) -NH-CpH2p- or CqH2q- (CO) -0-CpH2p-S- x is a number from 0 to 8; p is a number from 2 to 8; q is a number from 0 to 3; Ri and n are as defined above; or A, if E is -NHR3, is -C-H? x- or CqH2q- (CO) -NH-CpH2p-, where -x, p and q have the meanings cited above; or A, if E is COOH or S03H, is -CH2-S-CH2- or -CH2-S-CH2CH2-, where x has the meaning cited above; or O / \ A, if E is (CH2) m-CH-CH2, it is a direct link, -C < -H2q- (CO) -0-CH2 or -CXH2-S ~ CH2, where q, m, x, R! and R2 are as defined above; Or A, if E is -P-R4, is -CH2-; or sterically hindered amines of formula T, lia or Ilb (Ilb), where R8 is hydrogen, C1-C25 alkyl, C2-C20 alkenyl, C2-C2 alkynyl, Q1-C20 alkoxy, phenyl-C1-C3 alkyl, C5-C12 cycloalkyl, C5-CB cycloalkoxy, phenyl, naphthyl, hydroxyethyl, CO-C25 alkyl, CO-phenyl, CO-naphthyl, CO-phenyl-C1-C3 alkyl, O-CO-C1-C20 alkyl, or Ci-Cs-S alkyl C? -C6 alkyl, C? -C? 0 alkyl-C? -C6 alkyl, O /? C? -C6- (CO) alkyl-C? -C6 alkyl, -CH2CH2-0-CH2-CH-CH2 O is a number from 1 to 10; Y is a single bond, alkylene of C? -C25, phenylene, biphenylene, naphthylene, -O-alkylene of C1-C25, -NR9-, R9-C = 0 I -O- or -N-_C? -C25-alkylene; O-CH2-CH-CH2 z is hydrogen, -COOR9, -NH2, -0R9, hydroxyethyl, O R9 I II or -C-C = CH2; R9 is hydrogen or C1-C12 alkyl; Rio has the same definition as Ra; or lactones of formula III Ru, R12, Ri2a and R13 are each independently of the other, hydrogen, C1-C25 alkyl, phenyl-alkyl of. C1-C3, C5-C2-cycloalkyl or phenyl; and O / \ G is OH, OCH2CH2OH, -CH2-CH-CH2 or -0CH2C00H; -o sulphides of formula IV R15-S-R? s (IV), where S II Ris is C? -C? 8 alkyl, benzyl, phenyl or -P- (ORp) 2; Y Ris is -CH2CH20H,, -CH2COOH or -CH2CH2C00H; Y R n is unsubstituted or unsubstituted C 1 -C 4 alkyl or substituted C 1 -C 4 alkyl; 0 1 or phosphites of formula VR? Ía-P- (OR1 2 (V), where Risa is -CH2CH20H or -CH2CH2COOH; and Ri is C? -C? B or unsubstituted alkyl or C1-C4 alkyl- substituted phenyl or benzotriazoles, benzophenones or 2,4,6-triaryl-1,3,5-triazines of formulas VI, Via, VIb or VIc where Ris Ris is C? -Ca2 alkyl, a, a-dimethylbenzyl or a radical O / \ Rao is -OH, -SH, -NHR30, -SO3H, -C00R21, -CH = CH2, - (CH2) "-CH-CH2 or - (CO) -NH- (CHj) u-NCO; OR CH2"H / \ H2 R2? Is hydrogen, or -CH2-CH (OH) -CH2-0- (CO) -R22; R 22 is C 1 -C 4 alkyl or phenyl; R23 and R24 are each independently of the other, hydrogen or C? -C4 alkyl; R2S is hydrogen, - (CH2) u-OH,, - (CH2) uCOOH or - (CO) -NH- (CH2) "-NCO; R 26 is hydrogen, OH or C 1 -C 2 alkoxy; R27 is hydrogen or OH; R2s is hydrogen or _- -? 9 is hydrogen or halogen; R30 is hydrogen or C?-C9 alkyl; m is 0 or 1; t is a number from 0 to 6; u is a number from 2 to 12; with a compatibilizer compound.

To prepare the novel compounds, compatibilizers with specific reactive groups are suitable. These compatibilizers are polymers containing acid groups, acid anhydride groups, ester groups, epoxy groups or alcohol groups. Copolymers or terpolymers of polyethylene, polypropylene, vinyl acetate or styrene with acrylates are also suitable. Typical examples are polymers with acrylic acid (AA) function, the glycidyl methacrylate (GMA) function, the methacrylic acid (MAA) function, the maleic anhydride (MAH) function or the vinyl alcohol (VA) function. Preferred compatibilizers are, for example, copolymers consisting of polyethylene acrylic acid (PE-AA), polyethylene glycidyl methacrylate (P? -GMA), polyethylene methacrylic acid (PE-MAA), polyethylene maleic anhydride (PE-MAH) or polyethylene and vinyl acetate terpolymer with acrylates (for example PE-AA-acrylate). Also suitable as compatibilizers are grafted polyethylene or polypropylene copolymers, selected from the group consisting of maleic anhydride grafted to polyethylene vinyl acetate (MAK-g-acetate-of PE-vinyl), maleic anhydride grafted to low density polyethylene (MAH) -g-LDPE), maleic anhydride grafted to high density polyethylene (MAH-g-HDPE), linear low density polyethylene grafted maleic anhydride (MAH-g- LLDPE), acrylic acid grafted to polypropylene (AA-g-PP), glycidyl methacrylate grafted to polypropylene (GAH-g-PP), maleic anhydride grafted to polypropylene (MAH-g-EPDM), maleic anhydride grafted to terp limer ethylene / propylene (MAH-g-EPDM), maleic anhydride grafted to ethylene / propylene rubber (MAH-g-EPM), and maleic anhydride grafted to polyethylene / polypropylene copolymer (MAH-g-PE / PP). Other components of the suitable compatibilizers are co-or terpolymers of grafted styrene selected from the group consisting of styrene / acrylonitrile grafted with maleic anhydride (SAN-g-MAH), styrene / maleic anhydride / methyl ethacrylate block copolymers, styrene / butadiene / styrene grafted with maleic anhydride (SBS-g-MAH), styrene / ethylene / propylene / styrene block copolymers grafted with maleic anhydride (SEPS-g-MAH), styrene / butadiene / grafted styrene block copolymers with maleic anhydride (SEPS-g-MAH), and acrylic acid / polyethylene / polystyrene terpolymer (terpolymer AA-PE-PS). The important compatibilizers are those that contain anhydride units. Illustrative examples of suitable anhydrides are itaconic acid anhydride, citraconic anhydride, bicyclo [2.2.2] -5-octen-2,3-dicarboxylic acid anhydride, acid anhydride bicycle [2.2. l] -5-octen-2, 3-dicarboxylic, or maleic anhydride. Maleic anhydride is preferred. Particularly suitable as compatibilizers are copolymers or terpolymers having anhydride. Typical examples are ethylene / vinyl acetate / maleic anhydride terpolymers, ethylene / ethyl acrylate / maleic anhydride terpolymers, ethylene / acrylic acid / maleic anhydride terpolymers, styrene / maleic anhydride copolymers - or styrene terpolymer / maleic anhydride / methyl methacrylate. Such polymers and their preparation are known and described, inter alia, by PJ Flory in Principles of Polymer Chemistry, 1964, Cornell University Press, Ithaca, NY, as well as in Polymer compatibilizers and modifiers for virgin and recycled thermoplastics, including polymer materials Multiple or multi-layered, Maack Business Services, Study MBS No. 10, September 1990, Zürich. Also preferred as a component of the compatibilizer are copolymers or terpolymers containing a grafted anhydride, such as maleic anhydride grafted to polypropylene, maleic anhydride grafted to polyethylene, maleic anhydride-bonded to ethylene / vinyl acetate copolymer, block copolymer. styrene / ethylene / propylene / styrene (? EPS), styrene / ethylene / butylene / styrene block copolymer (SEBS), maleic anhydride grafted to ethylene / propylene terpolymer (EPDM), maleic anhydride grafted to ethylene / propylene copolymer. Such grafted polymers and their preparation are known and described, inter alia, in H.-G. Elias, Makromoleküle 1981, Hüthing & Wepf Verlag Heidelberg; or -in Polymers and polymer modifiers for virgin and recycled thermoplastics, including multi-polymer or multi-layer materials, Maack Business Services, Study MBS No. 10, September 1990, Zürich; as well as in M. Xanthos, Reactive Extrusion, 1992, Oxford University Press, NY. The maleic anhydride content is typically 0.05-15%, preferably 0.1-10%. Also suitable as a component of the compatibilizer are copolymers or terpolymers containing unsaturated carboxylic acid, typically acrylic acid, methacrylic acid, crotonic acid, fumaric acid, vinylacetic acid, maleic acid, itaconic acid. Acrylic acid, methacrylic acid, fumaric acid and maleic acid are preferred as in acrylic acid and methacrylic acid are particularly preferred. Illustrative examples of such copolymers or terpolymers are the ethylene / acrylic acid copolymer, copolymer of propylene / acrylic acid or terpolymer - ethylene / propylene / acrylic acid. Such polymers and their preparation are described, inter alia, in polymeric modifiers and compatibilizers for virgin and recycled thermoplastics, including multi-polymer and multi-layer materials, Maak Business Services, Study MBS No. 10, September 1990, Ziirich. The content of acrylic acid is typically 0.1-30%, preferably 0.1-25%. The preparation of the polymer, copolymer and terpolymer compatibilizers is carried out with the conventional polymerization processes with which one skilled in the art is familiar. The preparation of the polymers containing a carboxyl group has been published, for example by N.G. Gaylord in 'Reactive Extrusion; Principles and Practice ", Polymer Processing Institute, page 56 et seq., Hanser Verlag, München, Wien, New York (1992) In the same work, p 116 et seq., S. Brown describes the preparation of other carboxylated compatibilizers The reaction of the compatibilizer compound with a compound selected from the group consisting of sterically hindered phenols, sterically hindered amines, lactones, sulfides, phosphites, benzotriazoles, benzophenones and 2- (2-hydroxyphenyl) -1,3,5-triazines, which contain at least one functional reactive group, it is carried out as a graft reaction or analogous polymer reaction. The reactions can be carried out in solution or in the melt, depending on the reactants. Different reactors can be used in this case, for example tanks, extruders, mixers and the like. Extrusion is preferred. Reactive extrusion has been described, inter alia, by M. Xanthos in Reactive Extrusion, Principles and Practice, Polymer Processing Institute, Hanser Verlag, Munchen 1992. The reagents can be fed to the premixed or separated extruder, ie via feed devices separated, and can be reacted in the extruder. Liquid components or low melting point components can also be fed into the extruder via the feed pump (providing side channels). It may also be useful to degas the melt in the extruder, particularly when low molecular weight products are obtained in the reaction, which are preferably removed. For this purpose, the extruder needs to be equipped with a corresponding degassing device. The preparation can be carried out in commercially available single screw or twin screw extruders. The twin screw extruders are preferred. Obtaining the composition is carried out carried out by the usual techniques, for example, granulation. It is also possible to prepare and use a master batch (concentrate) of these compatibilizers / stabilizers by methods known in the art. The ratio of the compatibilizing component to the stabilizing component in the analogous polymeric reactions is, of course, limited by the number of reactive groups present in the compatibilizer components. A suitable weight ratio of compatibilizer / stabilizer is from 100: 0.05 to 100: 50, in particular from 100: 0.1 to 100: 25, preferably from 100: 1 to 100: 20. The novel compatibilizer / stabilizer compounds can be used, for example, to establish fluid polymers and, in particular, mixtures of such polymers. 1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for example of cyclopentene or ~ norbornene, polyethylene ( which may be optionally cross-linked), for example high density polyethylene (HDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), branched low density polyethylene (VLDPE). 2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / LDPE, PP / HDPE / LDPE, PP / HDPE / LLDPE / LDPE) and mixtures of different types of polyethylenes (for example LDPE / HDPE, LLDPE / LDPE, HDPE / LLDPE / LDPE) 3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for example ethylene / propylene copolymerbs, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene / but-1-ene copolymers, propylene / isobutylene copolymers, ethylene / but-1-ene copolymers, ethylene / hexene copolymers, copolymers ethylene / methylpentene, ethylene / heptene copolymers, ethylene / octene copolymers, propylene / butadiene copolymers, isobutylene / isoprene copolymers, ethylene / alkyl acrylate copolymers, ethylene / alkyl methacrylate copolymers, ethylene / acetate copolymers from vmi it and its copolymers with carbon monoxide or ethylene / acrylic acid copolymers and their salts (ionomers), as well as terpolymers of ethylene with propylene and a diene, such as hexadiene, dicyclopentadiene or ethylidene norbornene; and blends of such copolymers with each other and with the polymers mentioned in 1) above, for example polypropylene / ethylene-propylene copolymers, LDPE / ethylene-vinyl acetate copolymers, LDPE / ethylene-acrylic acid copolymers, copolymers of LLDPE / ethylene-vinyl acetate, vinyl acetate, copolymers of LLDPE / ethylene acrylic acid and alternating or random polyalkylene / carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides. 4. Polystyrene, poly (p-methylstyrene), poly (α-methylstyrene). 5. Copolymers of estrrene or α-methylstyrene with dienes or acrylic derivatives, for example styrene / butadiene, styrene / acrylonitrile, styrene / alkyl methacrylate, styrene / butadiene / alkyl acrylate, styrene / butadiene / alkyl methacrylate, styrene / maleic anhydride, styrene / acrylonitrile / methyl acrylate; high impact resistance mixtures of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylene / propylene / diene terpolymer; and styrene block copolymers such as styrene / butadiene / styrene, styrene / isoprene / styrene, styrene / ethylene / butylene / styrene or styrene / ethylene / propylene / styrene. 6. Grafted copolymers of styrene or α-methylstyrene, for example, styrene or polybutadiene, copolymers of styrene on polybutadiene-styrene or polybutadiene-acrylonitrile; styrene and acrylonitrile (or methacrylonitrile) or polybutadiene; styrene, acrylonitrile and methyl methacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, acrylonitrile and aleic anhydride on maleimide or polybutadiene; styrene and maleimide on polybutadiene; styrene - and alkyl acrylates or methacrylates on polybutadiene; styrene and acrylonitrile on ethylene / propylene / diene terpolymers; styrene and acrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile on acrylate / butadiene copolymers, as well as mixtures thereof with the copolymers listed under 5), for example, copolymer blends known as ABS polymers, MBS, ASA or AES. 7. Halogen-containing polymers, such as polychloroprene, chlorinated rubber, or chlorinated or chlorosulfonated polyethylene, copolymers of ethylene and chlorinated ethylene, and copolymers of. epichlorohydrin, especially polymers of halogen-containing vinyl compounds, for example polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof, such as vinyl chloride / sodium chloride. vinylidene, vinyl chloride / vi-acytate or vinylidene chloride / vinyl acetate. 8. Polymers derived from acids _ < x, β-unsaturates and derivatives thereof, such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, modified by impact with butyl acrylate. 9. Copolymers of the monomers mentioned under 8) with each other or with other unsaturated monomers, for example copolymers of acrylonitrile / butadiene, copolymers of acrylonitrile / alkyl acrylate, copolymers of acrylonitrile / alkoxyalkyl acrylate or acrylonitrile / vinyl halide or terpolymers of acrylonitrile / alkyl methacrylate / butadiene. 10. Polymers derived from unsaturated alcohols and amines or the acyl derivatives or acetals thereof, for example, vinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, phthalate. polyallyl or polyallyl melamine; as well as its copolymers with the olefins mentioned in 1) above. 11. Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or aminocarboxylic acids or the corresponding lactams, for example, polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides starting from m-xylene diamine and adipic acid; polyamides prepared from hexamethylenediamine and isophthalic and / or terephthalic acid and with or without elastomer as modifier, for example poly-2, 4, 4, -trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as polyamides or copolyamides modified with EPEM or ABS; and polyamides condensed during processing (RIM polyamide systems). 12. Polyesters derived from dicarboxylic acids and diols and / or from hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalene, poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates, as well as block copolymers of ether derivatives of hydroxyl terminated polyethers; and also polyesters modified with polycarbonates or MBS. 13. Polycarbonates and polyester carbonates. 14. Combinations of the aforementioned polymers (poly-combinations), for example PP / EPDM, poly Amide / EPDM or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylates, POM / PUR thermoplastic, PC / PUR thermoplastic, PQM / acrylate, POM / MBS, PPO / HIP ?, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO, PA / LDPE, PE / PET, PS / PE, PS / PP, PS / PE / PP, PE / PP / PET / PS. The novel compatibilizer / stabilizer compounds are added to the polymer to be stabilized in amounts of 0.5-30%, for example 1-20%, preferably 2-15% (based on the amount of polymer to be stabilized). The quantities depend on the one hand, the number of active stabilizing groups in the compounds and, on the other hand, the requirements of the polymers or polymer combinations to be established. The novel compatibilizer / stabilizer compounds are also used for in-phase compatibilization in plastic compositions where they act as stabilizers at the same time. These plastic compositions can be virgin plastic compositions (as described above) and also recycled. The novel stabilizers / co-stabilizers can, in principle, be used in all incompatible plastic compositions, virgin or recycled materials or in combinations of. virgin material and recycled. The plastic compositions may consist of two or more components. The novel components are preferably added to mixtures of polar and non-polar plastics.

The non-polar components of the plastic composition are, for example, polyolefins, typically polyethylene (PE) and polypropylene (PP). The ones mentioned in particular are low density polyethylene (LDPE), linear low density polyethylene (LLDPE) and high density polyethylene (HDPE), and also copolymers, such as ethylene / propylene copolymers (EPM) and ethylene / propylene / diene (EPDM), as well as ULDPE and MDPE. Such non-polar plastics also include polystyrene (PS, EPS) and copolymers having a styrene component (for example ABS, ASA, HIPS, IPS) and polyvinyl chloride (PVC), as well as copolymers with a vinyl chloride component predominant (for example CPE). The polar components are, for example, polyesters, such as polyethylene terephthalate (PET) or polybutylene terephthalate (PBT), polyamides or polycarbonates. Mixtures of polyethylene and polypropylene or polyethylene and polyamide are particularly preferred. The novel compatibilizer / stabilizer compounds can be used, for example, in redolated plastic compositions comprising 25-100% by weight, preferably 35-95% by weight, for example 40- 85% by weight of polyolefins, 0-25% by weight of polystyrene, 0-25% by weight of polyvinyl chloride and 0-25% by weight of the other thermoplastics. Non-thermoplastic materials can also be obtained in smaller quantities in the mixture. Of polyolefins, polyethylene (PE), in particular low density polyethylene, usually dominates. It should also be understood that polystyrene (PS) is for copolymers having a predominant styrene component (for example ABS, HIPS), and it should also be understood that polyvinyl chloride (PVC) is for copolymers having a component of predominant vinyl chloride (for example CPE). Other thermoplastics present in the material used are, in particular, polyethylene terephthalate (PET), and also polyamides, polycarbonate, cellulose acetate and polyvinylidene chloride. Thermoplastic materials may also be present in amounts of less than 5%, typically polyurethanes, formaldehyde resins and phenolic resins or also typical aminoplastics, as well as elastomers, such as rubber or latex. Minor amounts of foreign matter may also be present in the plastics used, such as paper, pigments, paint systems, printing inks, adhesives, which are often difficult to remove. Small amounts of cellulose or fibrous materials do not interfere with recycling.

Combinations of the novel compatibilizer / stabilizer compounds can also be added to the plastic compositions to be stabilized and to make them compatible. That is, for example, that it is convenient to use compounds having the same compatibilizing backbone, but which are functionalized differently with respect to the stabilizer, typically mixtures of compounds having a phenolic antioxidant function with compounds having a benzotriazole function, mixtures of compounds that have an antioxidant function with compounds having a HALS function, mixtures of compounds having a HALS function with compounds having a UV-absorbing function or, for example, mixtures of compounds having an antioxidant function with compounds having a HALS function and with compounds that have a UV absorbing function. The plastic compositions can be further mixed with other additives known to those skilled in the art. These additional additives are used in the usual quantities and combinations, detailed in the relevant literature (for example "Plastic Additives", Gachter / Müller, Hanser Verlag, München / Wien / New York, 3rd edition). The incorporation of novel compatibilizers / stabilizers into polymers or polymer combinations to be stabilized can be conveniently carried out as follows: as emulsion or dispersion; - as a dry mixture while combining the additional components or polymer combinations; by direct addition to the processor apparatus (for example calender, mixer, - kneader, extruder and the like), or - as a solution or in a molten state. The plastic compositions can be prepared in a manner known per se, by mixing the novel compounds and additional optional additives with the plastic composition, using the apparatuses known per se, such as the aforementioned processing apparatuses. The additional additives can be added alone or in mixture or also in the form of so-called master batches. By adding a suitable monomeric functionalized stabilizing compound and a radical initiator to the plastic composition directly, while processing the mixture, i.e. without a prior separate preparation of the compatibilizer / stabilizer compound, it is more possible to produce the compatibilizer / stabilizer compound and the composition compatible plastic in one step of the process. Similarly, it is possible to process a compound monomeric functionalized stabilizer - suitable and a corresponding compatibilizer together with the polymer blend, so that the compatibilizer compound reacts with a stabilizer compound without prior processing, and improve the compatibilized polymer blend obtained at the same time. The plastic compositions obtained according to this invention can be brought to the desired shape in a known manner. Such processes are, for example, grinding, calendering, extrusion, injection molding, sintering or centrifugation, and also blow molding by extrusion or processing by the plastisol process. The novel process comprises two different aspects, that is to say that two main purposes are achieved using the novel polymeric compatibilizer / stabilizer compounds. On the one hand, the polymers become compatible with each other in combinations of different polymers (virgin or recycled material), which, without compatibilizers, would form several phases, and the polymer is stabilized at the same time. On the other hand, the stabilizer becomes compatible or its solubility in the polymer increases because the polymeric backbone of the compatibilizer / stabilizer compound is compatible with the polymer to be stabilized. This also reduces the migration of the polymer stabilizer, which it is conceivable, for example, in the extraction of environmental media. This is the case, for example, when the compounds are used for fuel tanks, geotextiles, dry cleaning fibers (for example, textiles, carpet floors), pipes, applications with contact with food products and the like. The following Examples illustrate the invention in more detail. Here, as well as in the remainder of the description and in the claims, the parts and percentages are by weight, unless otherwise indicated.

I. Preparation of functionalized polymers Example A In a twin screw extruder (TW 100, from Haake, Germany), a copolymer of SEBS (styrene / ethylene / butadiene / styrene copolymer) was extruded with maleic anhydride groups (KratonßFG 1901, from Shell) at a temperature of 210-230 ° C (heating zone 1-5) and 45 rpm, with the addition of 2% of 3,5-bis (1,1-dimethylethyl) -4-hydroxybenzenepropionate 2,3-epoxypropyl. Subsequent analysis by gas chromatography shows that the additive can no longer be detected in its original form, that is, it is completely bound to the polymer chain.

Example B In general analogy with Example A, a polyethylene / acrylic acid / acrylate (Lucalen * A 3110 MX, ex BASF) was extruded with 2% of 3,5-bis (1,1-dimethylethyl) -4-hydroxy- 2,3-epoxypropyl benzene propionate.

Example C The procedure of Example B was repeated, but using 4% of 3,5-bis (1,1-dimethylethyl) -4-hydroxybenzene propionate of 2,3-epoxypropyl, Example D In general analogy with Example A, a? EB? Copolymer was reacted. with groups of maleic anhydride with 2% of 1, 2, 2, 6, 6-pehtamethyl-4- (2,3-epoxypropyloxy) -piperidine.

Example E In general analogy with Example B, it was reacted -polyethylene / acrylic acid / acrylate with 2% of 1, 2, 2, 6, 6-pentamethyl-4- (2,3-epoxypropyl) -piperidine.

Examples F, G, H In general analogy with Example E, 4%, 6% and 8% of each of 1, 2, 2, 6, 6-pentamethyl-4- (2,3-epoxypropyloxy) iperidine were used .

II) Use of polymeric stabilizers Examples 1-3 (Impact resistance as a function of oven aging) A composite mixture of 70% LDPE, low density polyethylene was added to the test products obtained.

(Lupolen® 3026, from BASF) with polyamide 6 (Ultramid® B 30, preseca, from BASF) with the functionalized compatibilizers prepared in the above Examples at 240 ° C and at 75 rpm (double screw extruder TX 100, Haake, Germany), were granulated and then injection molded at 240 ° C to the test samples. The impact resistance of these test samples was determined according to DIN 53 448, as a function of aging at 100 ° C in a circulating air oven. For comparison purposes, compositions were prepared and tested which comprised the corresponding non-functionalized compounds instead of the functionalized compatibilizers. The test compositions and the test results are given in the following Table 1. The higher the value of the impact resistance, the more stable the composition tested.

Table 1 The values obtained show that the functionalized compatibilizers stabilize the polymer more effectively when they are aged for a longer period of time than non-functionalized compatibilizers.

Examples 4-8: (Resistance to impact as a function of artificial environmental conditions) In general analogy with the method described in Examples 1-3, test samples were prepared and their impact resistance was determined as a function of the conditions artificial environmental The environmental conditions were carried out in an environmental meter O [Type Ci 65A, Atlas, BPT (black panel temperature) 63 ° C, RH (relative humidity) 60%, water spray]. The compositions and test results are shown in Table 2.

Table 2 The values obtained from the functionalized compatibilizers stabilize the polymer more effectively when maintained at ambient conditions for a prolonged period of time than non-functionalized compatibilizers. - - _ Examples 9-12: (impact resistance as a function of oven aging after extraction) A mixture of 70% low density polyethylene (LDPE) (Lupolenf3026 F, from BASF) with 30% polyamide 6 (Ultramid® B36 , preseca, from BASF) was composed with the novel compatibilizers / stabilizers compounds to be tested at 240 ° C and at 75 rpm, in a twin screw extruder. The test samples were then injection molded at 240 ° C. Those test samples were stored in an extraction medium: A) in white spirit - for 25 days at room temperature, B) in water with 1% Igepal CO630 (nonoxynol 9) for 2 weeks at 40 ° C. The dried test samples were then aged at 100 ° C in an oven with air circulation. The impact resistance was determined according to DIN 53 448 as a function of aging. The higher the value of impact resistance and the smaller decrease in this value after aging, the more stable the composition tested. The compounds tested and the test results for the extraction variant A are given in Table 3 and for those of variant B are given in Table 4. Table 3 Table 4

Claims (17)

REGVINDICATIONS

1. A process for stabilizing and at the same time compatibilizing by phase plastics or plastic compositions incorporating polymeric compounds obtained by the reaction of a compound selected from the group consisting of sterically hindered phenols, sterically hindered amines, lactones, sulfides, phosphites, benzotriazoles, benzophenones and 2- (2-hydroxy-phenyl) -1, 3, 5-triazines, compounds which are characterized in that they contain at least one reactive group, with a compatibilizer 2. The process according to claim 1, characterized in that the sterically hindered _phenols are the compounds of formula I (I) wherein Ri and R2 are each independently of -other, hydrogen, C? -C25 alkyl, phenylC? -C3 alkyl, which is unsubstituted or substituted once or several times in the aromatic ring by OH and / or unsubstituted C 1 -C 4 alkyl or substituted C 1 -C 4 -C 4 -cycloalkyl alkyl, or phenyl n is 1, 2, or 3 O O / \ II E is OH, SH, NHR3, S03H, COOH, -CH = CH2, (CHj) m-CH-CH

2 O-P-R4 I OH m is 0 or 1; R3 is hydrogen or C1-C9 alkyl; R4 is C? -C? 2 alkyl, or phenyl which is unsubstituted or substituted by one or more C1-C4 alkyl halogen and / or C? -C? Alkoxy, "A, if E is OH, SH or -CH = CH2, is -CxH2? -, -CH2-S-CH2CH2-, CqH2q- ICO) -0-CpH2, -, CqH2q- (CO) -NH-CpH2p- or -CqH2q- (CO) - 0-CpH2p-S-CqH2q-, x is a number from 0 to 8 p is a number from 2 to 8, q is a number from 0 to 3, Ri and n are as defined above, or A, if E is - NHR3, is -C * H2jI- or CqH2q- (CO) -NH-CpH2p, where x, p and q have the meanings cited above, or A, if E is COOH or SO3H, is -Cx-H2-, -CH2- S-CH2- or CH2S-CH2CH? -r cr. Dcnae x has the meaning cited above, or O / \ A, if E is (CH2) m-CH-CH2, it is a direct bond, CqH2q- (CO) "-0- CH2- or - J-2X-S-CH2-, wherein q, m, x, Ra and R2 are as defined above; or A, if E is -P II -R, is -CHs-

3. The process according to claim 1, characterized in that the sterically hindered amines are the compounds of formula II, lia or IIb. (IIb), wherein R8 is hydrogen, C?-C25 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C1-C20 alkoxy, phenyl-C1-C3 alkyl, C 3 -C 2 cycloalkyl, C 1 -C 8 cycloalkoxy, phenyl, naphthyl, hydroxyethyl, C 1 -C 25 alkyl, CO phenyl, CO naphthyl, C 0 phenyl C 1 -C 3 alkyl, O-CO 2 C.sub.1 -C.sub.20 alkyl or C.sub.1 -C.sub.6 -Salkyl C.sub. -CS alkyl / C.sub.C.sub.S-C.sub.1 -C.sub.6 alkyl- alkyl, alkyl O / \ of C? -Cs- (CO) -alkyl of C? -C6, -CH2-CH2-O-CH2-CH-CH2 or 0 / \ -CH2-CH-CH2; w is a number from 1 to 10; Y is a single bond, alkylene of Ci-, phenylene, R9-C = 0 I biphenylene, naphthylene, -O-alkylene of C1-C25, -NR9-, -O- or - R9-C = 0 I N-C? -C25-alkylene; O H2 R9 is hydrogen or C? -C_2 alkyl; R10 has the same definition as Rs.

4. The process according to claim 1, characterized in that the lactones are the compounds of formula III (III), where Rii, R-2,? 2a and R13 are each independently of the other, hydrogen, C? -C2S alkyl, phenylC1-C3 alkyl, C-? C2 cycloalkyl or phenyl; and O / \ G is OH, 0-CH2-CH-CH2, -OCH2CH20H or -0CH2C00H.

5. The process according to claim 1, characterized in that the sulfides are compounds of formula IV R? 5-SR? S (IV), wherein S Ris is C? -C? A alkyl, benzyl, phenyl or 1P- (0Rp) 2; and O / Ris is -CH2CH20H, -CH2-CH-CH2, -CH2C00H or -CH2CH2C00H; Y Rp is Ci-Ciß or substituted alkyl or C?-C4-substituted phenyl alkyl.

6. The process according to claim 1, characterized in that the phosphites are compounds of formula V O || Ri6.-P- (ORi7a) 2 (V), where Ris, is -CH2CH20H or -CH2CH2C00H; and Rp. is unsubstituted or unsubstituted C 1 -C 4 alkyl or C 1 -C 4 alkyl substituted phenyl.

The process according to claim 1, characterized in that the benzotriazoles, benzophenones and 2,4,6-triaryl-1,3,5-triazines are compounds of formula VI, Via, VIb or VIc where R is is - (CHjJ t-Rjo, -0-CH2-CH-CH2 or NH2; R1 is C1-C12 alkyl, a-a-dimethylbenzyl or a radical R2 H2 or - (CO) -NH- (CH2) u-NCO; 5 R2? is hydrogen, or -CH2-CH (OH) -CH2-0- (CO) -R22; R 22 is C 1 -C 4 alkyl or phenyl; R23 and 24 are each independently of the other, hydrogen or C? -C alkyl; 0 -Ci2"CH-CH2 R25 is hydrogen, - (CH2) U-0H,, (CH2) uC00H or - (CO) -NH- (CH2) u-NC0; R26 is hydrogen, OH or C alco alkoxy; C? 2; R27 is hydrogen or OH; R28 is hydrogen or R29 is hydrogen or halogen; R30 is hydrogen or C? -C9 alkyl; m is 0 or 1; t is a number from 0 to 6; u is a number from 2 to 12.

The process according to claim 1, characterized in that the compatibilizer compound is a polymer containing acid groups, acid anhydride groups, ester groups, epoxy groups or alcohol groups or wherein the compatibilizing compounds are a copolymer or terpolymer of polyethylene, polypropylene, vinyl acetate or styrene with acrylic acid.

9. The process according to claim 8, characterized in that the compatibilizer compound is a polymer with the function acrylic acid (AA), function glycidyl methacrylate (GMA), methacrylic acid function (MAA), maleic anhydride (MAH) function or vinyl alcohol function (VA).

10. The process according to claim 8, characterized in that the compatibilizer compound is a copolymer consisting of polyethylene acrylic acid (PE-AA), polyethylene glycidyl methacrylate (PE-GMA), polyethylene methacrylic acid (PE-MAA) or polyethylene maleic anhydride (PE-MAH) or a terpolymer of polyethylene and vinyl acetate with acrylic acid or a terpolymer of polyethylene and acrylates with acrylic acid.

11. The process according to claim 8, characterized in that the compatibilizer compound is a polyethylene-or polypropylene copolymer inserted selected from the group consisting of maleic anhydride grafted to polyethylene vinyl acetate (MAH-g-PE-vinyl acetate), maleic anhydride grafted to low density polyethylene (MAH-g-LDPE), maleic anhydride grafted to high density polyethylene (MAH-g-HDPE), grafted maleic anhydride linear low density polyethylene (MAH-g-LLDPE), acrylic acid grafted to polypropylene (AA-g-PP), glycidyl methacrylate grafted to polypropylene (GMA-g-PP), maleic anhydride grafted to polypropylene (MAH-g) -EPEM), maleic anhydride grafted to ethylene / propylene terpolymer (MAH-g-EPDM), anhydride 10 Maleic grafted to ethylene / propylene rubber (MAH-g-EPM), and maleic anhydride grafted to polyethylene / polypropylene copolymer (MAH-g-PE / PP).

12. The process according to claim 8, characterized in that the compatibilizer compound lb is a co-or terpolymer of grafted styrene selected from the group consisting of styrene / acrylonitrile grafted with maleic anhydride (SAN-g-MAH), copolymers of Styrene blocks / maleic anhydride / methyl methacrylate, styrene / butadiene / styrene or grafted maleic anhydride (SBS-g-MAH), styrene / ethylene / propylene / styrene block copolymers grafted with maleic anhydride (SEPS-g-MAH) ), styrene / butadiene / styrene block copolymers grafted with maleic anhydride (SEPS-g-MAH), and acrylic acid / polyethylene / polystyrene terpolymer (terpolymer AA-PE-PS).

13. The process according to claim 8, characterized in that the compatibilizer compound is a copolymer of vinyl alcohol-

14. The process according to claim 1, characterized in that the polymers to be stabilized are at least two different polymers.

15. The process according to claim 1, characterized in that the polymers to be stabilized are recycled materials.

16. A compound obtainable by -the reaction of sterically hindered phenols of formula I- E (I), wherein Ri and R2 are each independently of the other, hydrogen, C? -C25 alkyl, phenyl-C1-C3 alkyl, which is unsubstituted or substituted once or several times in the aromatic ring by OH and / or C 1 -C 4 alkyl, unsubstituted C 1 -C 4 -cycloalkyl substituted C 5 -C 20 cycloalkyl, or phenyl; n is 1, 2, or 3 O O / \ II E is OH, SH, NHR3, SO3H, COOH, -CH = CH2, (CH2) "-CH-CH2 or -P-R" I OH m is O or 1; R3 is hydrogen or C? -C9 alkyl; R 4 is C 1 -C 12 alkyl, or phenyl, which is not "substituted or substituted by one or more C 1 -C 4 alkyl halogen and / or C 1 -C 4 alkoxy; A, if E is OH, SH or -CH "CH2, is -C? H2í [-, -CH2-S-CH2CH2-, qKZv- (C0) -O-CpH2p-, CqH2q- (CO) -NH-CpHzp- or -CqH2q- (CO) -0-CpH2p-S-CqH2q-; x is a number from 0 to 8 0 p is a number from 2 to 8, q is a number from 0 to 3, Ri and n are as defined above, or A, if E is -NHR3, is -CxH2x- or CqH2q- (CO) -NH-CpH2p, where x, p and q have the meanings cited above, or 5 A, if E is COOH or S03H, is -C "-H2¡! -CH2-S-CH2- or CH2S-CH2CH2-, where x has the meaning cited above, or 0 / \ A, if E is (CH2) m-CH-CH2, it is a direct bond, CqH2q- (CO) m-0- CH2- or -C? H2x-S-CH2-, where q, m, x, Ri and R2 are as defined above; OA, if E is -P II -R4, is -CH2- or sterically hindered amines of the formula II, lia, or Ilb b (IIb), wherein Rβ is hydrogen, C?-C25 alkyl, C2-C20 alkenyl, C2-C2 alkynyl, C?-C20 alkoxy, phenyl-C1-C3 alkyl, Cs-C cycloalkyl? 2, C5-C8 cycloalkoxy, phenyl, naphthyl, hydroxyethyl, CO-C25 alkyl, CO-phenyl, CO-naphthyl, C0-phenyl-C1-C3 alkyl, O-CO-C1-C-alkyl or alkyl C? -C6-S-C? -C8 alkyl, C? -C6 alkyl-C? -C3 alkyl, alkyl or Ci-Cβ-CCO) -alkyl of C? -C6, -CH2-CH2-0-CH2-CH-CH2 or O w is a number from 1 to 10; Y is a single bond, C1-C25 alkylene, phenylene, R9-C = 0 biphenylene, naphthylene, -O-alkylene of C? -C25, "-NR9- or -N-IC-C2-, -alkylene; CH-CH2 R9 is hydrogen or C1-C12 alkyl, Rio has the same definition as R8 or lactones of formula III R 11, R 12, R 2a and R 13 are each independently of the other, hydrogen, C 1 -C 2 alkyl, phenyl C 1 -C 3 alkyl, C, -C 2 cycloalkyl or phenyl; Y or /? G is OH, OCH2CH2OH, -CH2-CH-CH2 or -0CH2C00H; or sulfides of formula IV Ris-S-Ris (IV), wherein 5 S II Ri 5 is C 1 -C 8 alkyl, benzyl, phenyl or -P- (0Rp) 2; Y 0 / \ - CH2-CH-CH2 Rie is -CHaCHjOH,, -CH2CO0H or -CH2CH2COOH; Y 10 p is C 1 -C 8 alkyl or unsubstituted alkyl or C 1 -C 4 alkyl substituted phenyl; or phosphites of formula V or Ri6a-1P- (ORpa) 2 (V), wherein Riea is -CH2CH20H or -CH2CH2C00H; and Ri a is unsubstituted or unsubstituted C 1 -C 4 alkyl or substituted C 1 -C 4 alkyl; or benzotriazoles, benzophenones or 2,4,6-triaryl-1,3,5-triazines of formula VI, Via, VIb or VIc Ü0 O / Ris is - (CH2) t-R20, -0-CH2-CH-CH2 or NH2; Ra 9 is C 1 -C 2 alkyl, a, a-dimethylbenzyl or a radical o / \ R_o is -OH, -SH, -NHR30, -S03H, -COOR21, -CH = CH2, - (CH2) m -CH-CH2 or - (CO) -NH- (CH2) "-NCO; OR CH2 'H / \ H2 R2i is hydrogen, or -CH2-CH (OH) -CH2-0- (CO) -R22; R 22 is C 1 -C 4 alkyl or phenyl; R23 and R24 are each independently of the other, hydrogen or C1-C4 alkyl; O C-E2"H / \ CI - 2 ~~ R25 is hydrogen, - (CH2) u-OH,, - (CH2) uCOOH or - (CO) -NH- (CH2) u-NCO; R26 is hydrogen, OH or C1-C12 alkoxy; R27 is hydrogen or OH; R28 is hydrogen or R29 is hydrogen or halogen; R30 is hydrogen or C? -C9 alkyl; m is 0 or 1; t is a number from 0 to 6; u is a number from 2 to 12; with a compatibilizer compound.

17. The use of the compounds according to claim 16 as stabilizers and at the same time as phase compatibilizers in plastics or plastic compositions.