ITMI20000326A1 - Composti appartenenti alla classe delle ammine stericamente impedite procedimento per la loro preparazione e loro utilizzo in polimeri organ - Google Patents
Composti appartenenti alla classe delle ammine stericamente impedite procedimento per la loro preparazione e loro utilizzo in polimeri organ Download PDFInfo
- Publication number
- ITMI20000326A1 ITMI20000326A1 IT2000MI000326A ITMI20000326A ITMI20000326A1 IT MI20000326 A1 ITMI20000326 A1 IT MI20000326A1 IT 2000MI000326 A IT2000MI000326 A IT 2000MI000326A IT MI20000326 A ITMI20000326 A IT MI20000326A IT MI20000326 A1 ITMI20000326 A1 IT MI20000326A1
- Authority
- IT
- Italy
- Prior art keywords
- general formula
- class
- butyl
- hydroxy
- sterically hindered
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 50
- 150000001412 amines Chemical class 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229920000642 polymer Polymers 0.000 title description 18
- 210000000056 organ Anatomy 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 61
- 150000002148 esters Chemical class 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 12
- 229920000620 organic polymer Polymers 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004611 light stabiliser Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- -1 for example Substances 0.000 description 108
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- 229910052757 nitrogen Inorganic materials 0.000 description 26
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
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- 239000005977 Ethylene Substances 0.000 description 10
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- 239000005062 Polybutadiene Substances 0.000 description 10
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
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- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
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- 239000007859 condensation product Substances 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
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- 239000007983 Tris buffer Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
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- 239000007787 solid Substances 0.000 description 5
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- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- PKTNMTDLDLSRDE-UHFFFAOYSA-N C1OC2(P(=O)=O)OCC1(CO)CO2 Chemical compound C1OC2(P(=O)=O)OCC1(CO)CO2 PKTNMTDLDLSRDE-UHFFFAOYSA-N 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 229920002943 EPDM rubber Polymers 0.000 description 3
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- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000554 ionomer Polymers 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 description 2
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- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
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- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 description 2
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- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
"COMPOSTI 'APPARTENENTI ALLA CLASSE DELLE AMMINE STERICAMENTE IMPEDITE, PROCEDIMENTO PER LA LORO PREPARAZIONE E LORO UTILIZZO IN POLIMERI ORGANICI"
DESCRIZIONE
La presente invenzione riguarda composti appartenenti alla classe delle ammine stericamente impedite .
Più in particolare, la presente invenzione riguarda composti appartenenti alla classe delle ammine stericamente impedite costituiti da miscele di monomeri e/o oligomeri di esteri carbonici di un idrossi-alchil-2 ,2,6,6-tetrametil-piperidinolo, un procedimento per la loro preparazione ed il loro utilizzo come stabilizzanti alla luce per polimeri organici .
La presente invenzione riguarda inoltre le composizioni polimeriche stabilizzate con i suddetti composti ed i manufatti ottenuti da dette composizioni.
Composti appartenenti alla classe delle ammine stericamente impedite sono noti nell'arte: detti composti possono essere solidi oppure liquidi.
La Richiedente ha ora trovato composti appartenenti alla classe delle animine stericamente impedite costituiti da miscele di monomeri e/o oligomeri di esteri carbonici di un idrossi-alchil-2 ,2,6,6-tetrametil-piperidinolo che, a seconda del rapporto monomeri e/o oligomeri presenti nella miscela finale, possono essere solidi o liquidi: detto rapporto può essere cambiato a seconda del procedimento utilizzato per la loro preparazione e, di conseguenza, può essere deciso in anticipo, a seconda dell' utilizzo finale, quale tipo di composto si vuole ottenere.
Costituiscono pertanto oggetto della presente invenzione composti appartenenti alla classe delle aminine stericamente impedite, costituiti da miscele di monomeri e/o oligomeri di esteri carbonici di un idrossi--alchil--2, 2,6,6— tetrametil— piperidinolo, aventi formula generale (I):
in cui:
R1 rappresenta un atomo di idrogeno; un gruppo alchilico C1-C6 lineare o ramificato; un gruppo arilico C6-C12;
m è 1 o 2;
R2 rappresenta un gruppo -OCOOR1 in cui R1 ha gli stessi significati sopra descritti; oppure rappresenta un gruppo idrossilico;
n rappresenta un numero intero compreso tra 1 e 9 estremi inclusi.
I composti aventi formula generale (I) sono utili come stabilizzanti alla luce per polimeri organici.
Esempi di gruppi alchilici C1-C6 lineari o ramificati sono: metile, etile, propile, t-butile, ecc.
Esempi di gruppi arilici C6-C12 sono: fenile, naftile, ecc.
Esempi specifici di composti aventi formula generale (I), da non considerarsi in alcun modo limitativi della presente invenzione, sono:
Composto avente formula (Ia):
in cui n è un numero intero compreso tra 1 e 6 estremi inclusi;
Composto avente formula (Ib):
in cui n è un numero intero compreso tra 1 e 6 estremi inclusi.
I composti appartenenti alla classe delle animine sfericamente impedite aventi formula generale (I) oggetto della presente invenzione possono essere preparati attraverso vari procedimenti.
Ulteriore oggetto della presente invenzione è un procedimento per la preparazione dei composti aventi formula generale (I).
Un procedimento per la preparazione dei composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) comprende la reazione di esterificazione di un idrossialchil-2,2,6, 6-tetrametil-piperidinolo avente formula generale (II):
in cui R2 ed m hanno gli stessi significati sopra descritti, con un dialchil carbonato avente formula generale (III):
in cui R1 ha gli stessi significati sopra descritti, in presenza di una base come catalizzatore quale, ad esempio, metilato di sodio, ecc., eventualmente in presenza di un solvente organico inerte scelto tra i solventi aromatici quali, ad esempio, toluene, clorobenzene, ecc., ad una temperatura compresa tra 50°C e 200°C, preferibilmente tra 50°C e 140 °C, per un tempo compreso tra 2 ore e 12 ore, preferibilmente tra 6 ore ed 8 ore.
Nel caso in cui si desideri ottenere il monomero (n 1) o miscele liquide a basso contenuto di oligomeri (n compreso tra 1 e 3 estremi inclusi), la suddetta reazione di esterificazione viene condotta utilizzando l'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) in rapporto molare compreso tra 4:1 e 20:1, preferibilmente in rapporto molare 17:1. In questo caso, durante la suddetta reazione di esterificazione, si forma metanolo che viene eliminato per distillazione azeotropica utilizzando il dialchil carbonato in eccesso ed ottenendosi, prima il monoestere e, successivamente, il diestere dell'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II): durante questa fase viene monitorata l'effettiva scomparsa dell'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II) tramite analisi gas-cromatografica (GC). I composti appartenenti alla classe delle animine stericamente impedite aventi formula generale (I) così ottenuti si presentano sotto forma di liquidi, passando da un liquido poco viscoso nel caso del monomero, a liquidi più viscosi nel caso delle miscele di oligomeri, aventi una temperatura di transizione vetrosa (Tg) inferiore a 0°C.
Nel caso in cui si desideri ottenere miscele ad elevato contenuto di oligomeri (n compreso tra 4 e 9 estremi inclusi), aventi peso molecolare medio pari a 998, la suddetta reazione di esterificazione viene condotta utilizzando 1'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) in rapporto molare compreso tra 1:1 e 1:2, preferibilmente in rapporto molare 1:1. In questo caso, durante la suddetta reazione di esterificazione, il metanolo che si forma prima e, successivamente, a temperatura più alta, il dialchil carbonato, vengono eliminati dalla massa viscosa per trascinamento con un solvente aromatico inerte quale, ad esempio, toluene, clorobenzene, ecc., ottenendosi esteri oligomerici dell'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II): durante questa fase viene dapprima monitorata l'effettiva scomparsa dell'ìdrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II) tramite gas-cromatografia (GC) e, successivamente, la formazione degli oligomeri tramite cromatografia liquida ad alta pressione (HPLC) utilizzando il rivelatore "light scattering" (ELSD). I composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) così ottenuti si presentano sotto forma di solidi scagliettabili, aventi una temperatura di fusione compresa tra 100°C e 250°C.
Al termine delle suddette reazioni di esterificazione, i composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I), liquidi o solidi, vengono lavati con acqua per allontanare i residui basici e, successivamente, vengono essiccati sotto vuoto.
La composizione delle miscele ottenute viene monitorata utilizzando diversi metodi analitici quali, ad esempio cromatografia in fase supercritica (SFC), cromatografia liquida ad alta pressione su colonna (HPLC), cromatografia di permeazione su gel (GPC), utilizzando rivelatori tipo indice di rifrazione (RI) o "light scattering"(ELSD).
L'ìdrossì-alchil-2 ,2,6,6-tetrametil-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) sono prodotti noti e commercialmente disponibili.
Come già detto sopra, i composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) oggetto della presente invenzione possono essere utilizzati come stabilizzanti alla luce per una vasta varietà di polimeri organici. Esempi di polimeri organici a cui possono essere aggiunti sono:
1. Polimeri delle monoolefine e delle diolefine come, ad esempio, polipropilene, poliisobutilene, polibut-1-ene, poli-4-metilpent-1-ene, poliisoprene o polibutadiene; così come polimeri delle cicloolefine come, ad esempio, ciclopentene o norbornene; polietilene (che può essere opzionalmente reticolato) come, ad esempio, polietilene ad elevata densità (HDPE) , polietilene ad elevata densità e ad elevato peso molecolare ((HDPE-HMW) , polietilene ad elevata densità ed ad elevatissimo peso molecolare (''ultrahigh molecular weight") (HDPE-UHMW), polietilene a media densità (MDPE), polietilene a bassa densità (LDPE) , polietilene lineare a bassa densità (LLDPE), polietilene ramificato a bassa densità (BLDPE) , (VLDPE), (ULDPE).
Le poliolefine quali, ad esempio le monolefine esemplificate nel paragrafo precedente, preferibilmente il polietilene ed il polipropilene, possono essere preparate attraverso diversi metodi noti in letteratura, preferibilmente utilizzando i seguenti metodi:
(a) polimerizzazione radicalìca (generalmente condotta ad elevata pressione e ad elevata temperatura);
(b) polimerizzazione catalitica utilizzando un catalizzatore che normalmente contiene uno o più metalli dei gruppi IVb, Vb, VIb o Vili della Tavola Periodica. Detti metalli, generalmente, hanno uno o più leganti quali, ad esempio, ossidi, alogenuri, alcoolati, esteri, eteri, ammine, alchili, alchenili e/o arili che possono essere π- oppure σcoordinati. Questi complessi metallici possono essere in forma libera oppure supportati su substrati quali, ad esempio, magnesio cloruro attivato, titanio (III)cloruro, allumina od ossido di silicio. Detti catalizzatori possono essere solubili od insolubili nel mezzo di polimerizzazione. I catalizzatori possono essere utilizzati da soli oppure in presenza di altri attivatori quali, ad esempio, alchili metallici, idruri metallici, alogenuri di aichili metallici, ossidi di alchilici metallici od alchilossani metallici, detti metalli essendo elementi appartenenti ai gruppi la, Ila e/o Illa della Tavola Periodica. Gli attivatori possono essere convenientemente modificati con altri gruppi esterei, eterei, amminici o silil-eterei. Detti sistemi catalitici vengono usualmente chiamati Phillips, Standard Oil Indiana, Ziegler (-Natta) , TNZ (Du-Pont) , metallocene o "single site catalyst" {SSC).
2. Miscele dei polimeri descritti al punto (1) come,· ad esempio, miscele di polipropilene con poliisobutilene; miscele di polipropilene con polietilene (ad esempio, PP/HDPE, PP/LDPE) ; miscele di differenti tipi di polietilene (ad esempio, LDPE/HDPE) .
3. Copolimeri delle monoolefine e delle diolefine tra loro o con altri monomeri vinilici come, ad esempio, copolimeri etilene/propilene, polietilene lineare a bassa densità (LLDPE) e sue miscele con polietilene a bassa densità (LDPE), copolimeri propilene/but-1-ene, copolimeri propilene/isobutilene, copolimeri etilene/but-1-ene, copolimeri etilene/esene, copolimeri etilene/metilpentene, copolimeri etilene/eptene, copolimeri etilene/ottene, copolimeri propilene/butadiene, copolimeri isobutilene/isoprene, copolimeri etilene/alchil acrilato, copolimeri etilene/alchil metacrilato, copolimeri etilene/vinil acetato e loro copolimeri con monossido di carbonio o copolimeri etilene/acido acrilico e loro sali (ionomeri) così come terpolimeri dell'etilene con propilene ed un diene come, ad esempio, esadiene, diciclopentadiene o etilidenenorbornene; ed anche miscele di detti copolimeri tra loro oppure con i polimeri sopra riportati al punto (1) quali, ad esempio, copolimeri polipropilene/etilene/propilene, copolimeri LDPE/etilene/-vinil acetato (ÈVA), copolimeri LDPE/etilene/acido acrilico (EAA), LLDPE/EVA, LLDPE/EAA, e copolimeri alternati o "random" polialchilene/monossido di carbonio e loro miscele con altri polimeri quali, ad esempio, poliammidi.
4. Resine idrocarburiche (ad esempio, C5-C9) comprendenti le loro modificazioni idrogenate (ad esempio, resine adesivanti) e miscele con polialchileni ed amido.
5. Polistirene, poli(p-metilstirene), poli(αmetilstirene ).
6. Copolimeri dello stirene o dell'α-metilstirene con dieni o derivati acrilici come, ad esempio, stirene/butadiene, stirene/acrilonitrile, stirene/alchil metacrilato, stirene/butadiene/alchil acrilato, stirene/butadiene/alchil metacrilato, stirene/anidride maleica, stirene/acrilonitrile/metil acrilato; miscele, aventi un elevato carico di rottura, tra copolimeri dello stirene ed un altro polimero come, ad esempio, un poliacrilato, un polimero di un diene od un terpolimero etilene/propilene/diene, copolimeri a blocchi dello stirene come, ad esempio, stirene/butadiene/stirene, stirene/isoprene/stirene, stirene/etilene/butilene/stirene o stirene/etilene/propilene/stirene.
7. Copolimeri graffati dello stirene o dell'αmetilstirene come, ad esempio, stirene in polibutadiene, stirene in polibutadiene/stirene o copolimeri polibutadiene/acrilonitrile; stirene ed acrilonit.rile (o metacrilonitrile) in polibutadiene; stirene, acrilonitrile e metilmetacrilato in polibutadiene; stirene ed anidride maleica in polibutadiene; stirene, acrilonitrile ed anidride maleica o maleimmide in polibutadiene; stirene e maleimmide in polibutadiene; stirene ed alchilacrilati od alchilmetacrilati in polibutadiene; stirene ed acrilonitrile in terpolimeri etilene/propilene/diene, stirene ed acrilonitrile in polialchil acrilati o polialchil metacrilati, stirene ed acrilonitrile in copolimeri acrilato/butadiene, così come miscele dei copolimeri sopra riportati con i copolimeri riportati al punto (6) come, ad esempio, miscele di copolimeri note come ABS, MBS, ASA o AES;
8. Polimeri contenenti alogeni come, ad esempio, policloroprene, gomme clorurate, copolimeri isobutilene-isoprene clorurati o brominati ("halobutyl rubber"), polietilene clorurato o clorosulfonato, copolimeri etilene ed etilene clorurato, omopolimeri e copolimeri dell'epicloridrina, in<' >particolare polimeri di composti vinilici contenenti alogeni come, ad esempio, polivinil cloruro, polivinilidene cloruro, polivinil fluoruro o polivinilidene fluoruro; ed anche loro copolimeri come, ad esempio, vinil cloruro/vinilidene cloruro, vinil cloruro/vinil acetato o vinilidene cloruro vinil acetato.
9. Polìmeri derivati da acidi α,β-insaturi e loro derivati come, ad esempio, poliacrilati e polimetacrilati, polimetil metacrilati, modificati all'impatto con butil acrilato, poliacrilammidi e poliacriIonitrili .
10. Copolimeri dei monomeri di cui al punto (9) tra loro o con altri monomeri insaturi come, ad esempio, copolimeri acrilonitrile/butadiene, copolimeri acrilonitrile/alchil acrilato, copolimeri acrilonitri.Le/alcossialchil acrilato o copolimeri acrilonitrile/alogenuro vinilico o terpolimeri acrilonitrile/alchil metacrilato/butadiene.
11. Polimeri derivati da alcooli insaturi ed animine, o loro derivati acilici od acetalici come, ad esempio, polivinil alcool, polivinil acetato, polivinil stearato, polivinil benzoato, polivinil maleato, polivinil butirrale, poliallil ftalato o poliallil melammina; così come loro copolimeri con le olefine di cui al punto (1).
12. Omopolimeri e copolimeri di eteri a catena aperta oppure di eteri ciclici come, ad esempio, glicoli polialchilenici, polietilene ossido, polipropilene ossido, oppure copolimeri dei composti sopra descritti con bis-glicidil eteri.
13. Poliacetali come, ad esempio, poliossimetilene e quei poliossimetileni che contengono comonomeri, ad esempio, ossido di etilene; poliacetali modificati con poliuretani termoplastici, acrilati o MBS.
14. Ossidi e solfuri del polifenilene e loro miscele con polimeri stirenici o poliammidi.
15. Poliuretani derivati da polieteri, poliesteri o. polibutadieni idrossil-terminati da un lato e poliisocianati alifatici od aromatici dall'altro, così come i precursori dei composti di cui sopra.
16. Poliammidi e copoliammidi derivate da diammine ed acidi dicarbossilici e/o da acidi amminocarbossilici o dai corrispondenti lattami come, ad esempio, poliammide 4, poliammide 6, poliammide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, poliammide 11, poliammide 12, poliammidi aromatiche ottenute a partire da m-xilene, diammina ed acido adipico; poliammidi preparate da esametilenediammina ed acido isoftalico e/o tereftalico e con o senza un elastomero come agente modificante, ad esempio, poli-2,4,4-trimetilesametilene tereftalammide o poli-m-fenilene isoftalammide; ed anche copolimeri a blocchi delle suddette poliammidi con poliolefine, copolimeri olefinici, ionomeri od elastomeri legati chimicamente o graffati; o con polieteri come, ad esempio, polietilene glicole, polipropilene glicole o politetrametilene glicole; così come poliammidi o copoliammidi modificate con EPDM od ABS; e poliammidi condensate durante la lavorazione ("RIM polyamide System").
17. Poliuree, poliimmidi, poliammideimmidi, polieteriimmidi, poliesteriimmidi, poliidantoine, e polibenzoimidazoli .
18. Poliesteri derivati da acidi dicarbossilici e dioli e/o da acidi idrossicarbossilici o dai corrispondenti lattoni come, ad esempio, polietilene tereftalato, polibutilene tereftalato, poli-1,4-dimetilolcicloesano tereftalato, poliidrossibenzoati, così come polieteri esteri a blocchi derivati da polieteri idrossil-terminati; ed anche poliesteri modificati con policarbonati o MBS.
19. Policarbonati e poliesteri carbonati.
20. Polisolfonì, polieterisolfoni e polieterichetoni.
21. Polimeri reticolati derivati da aldeidi da una parte e da fenoli, urea e melammine dall'altra come, ad esempio, resine fenolo/formaldeide, resine urea/formaldeide e resine melammina/formaldeide. 22. Resine alchidiche essicate o non-essicate.
23. Resine a base di poliesteri insaturi derivate da copoliesteri di acidi dicarbossilici saturi ed insaturi con alcooli poliidrici e composti vinilici come agenti reticolanti, ed anche resine di cui sopra contenenti alogeni ed aventi una buona resistenza alla fiamma.
24. Resine acriliche reticolabili derivate da acrilati sostituiti come, ad esempio, epossi acrilati, uretani acrilati o poliesteri acrilati.
25. Resine alchidiche, resine a base di poliesteri o resine acrilate reticolate con resine melamminiche, resine a base di urea, resine a base di isocianati, resine a base di isocianurati, resine a base di poliisocianati o resine epossidiche.
26. Resine epossidiche reticolate derivate da composti glicidilici alifatici, cicloalifatici, eterociclici od aromatici quali, ad esempio, prodotti di eteri diglicidilici del bisfenolo A e del bisfenolo F, che vengono reticolati con gli agenti reticolanti usuali quali, ad esempio, anidridi od ammine, in presenza od in assenza di acceleranti.
27. Polimeri naturali come, ad esempio, cellulosa, gomma naturale, gelatina, e loro derivati chimicamente modificati per dare polimeri omologhi come, ad esempio, acetati, propionati e butirrati di cellulosa, oppure eteri di cellulosa come, ad esempio, metil-cellulosa; così come resine idrocarburiche ("rosins") e loro derivati.
28. Miscele dei polimeri sopra menzionati ("polyblends") come, ad esempio, PP/EPDM, poliammide/EPDM O ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrilati, POM/termoplastici PUR, PC/termoplastici PUR, POM/acrìlati , POM/MBS, PPO/HIPS, PPO/PA 6.6 e copolimeri, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS, PBT/PET/PC .
29. Materiali organici naturali o sintetici che sono composti monomerici puri o miscele di detti composti quali, ad esempio, olii minerali, olii, grassi o cere animali o vegetali, olii, grassi o cere a base di esteri sintetici (ad esempio, ftalati, adipati, fosfati, trimellìtati), come anche miscele di esteri sintetici con olii minerali in qualsivoglia rapporto in peso, in particolare quelli utilizzati nelle composizioni per filatura, così come le emulsioni acquose di detti materiali organici.
30. Emulsioni acquose di gomme naturali o sintetiche quali, ad esempio, lattice naturale o lattici a base di copolimeri stirene-butadiene carbossilati.
I composti appartenenti alla classe delle animine stericamente impedite aventi formula generale (I) oggetto della presente invenzione sono particolarmente utili nella stabilizzazione dei polimeri organici scelti tra quelli sopra riportati. Preferibilmente, sono utili nella stabilizzazione delle poliolefine sopra riportate al punto {1).
La presente invenzione riguarda, inoltre, composizioni polimeriche contenenti un polimero organico ed una quantità efficace dì uno o più composti appartenenti alla classe delle animine stericamente impedite aventi formula generale (I).
Ulteriore oggetto della presente invenzione sono i manufatti ottenuti dalla lavorazione delle suddette composizioni polimeriche.
In generale, i suddetti composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) vengono utilizzati in quantità compresa tra circa 0,01% e circa 5% in peso sul peso delle composizioni polimeriche da stabilizzare, sebbene la quantità utilizzata vari in funzione del substrato da stabilizzare e della applicazione finale. Preferibilmente, vengono utilizzati in quantità compresa tra circa 0,1% e circa 3% in peso sul peso delle composizioni polimeriche da stabilizzare .
I composti appartenenti alla classe delle animine sfericamente impedite aventi formula generale (I) oggetto della presente invenzione possono essere utilizzati tal quali od in miscela tra loro od, eventualmente, in combinazione con altri additivi convenzionali o loro miscele. Detti additivi vengono aggiunti in quantità compresa tra circa 0,1% e circa 5% in peso sul peso delle composizioni polimeriche da stabilizzare, preferibilmente tra circa 0.51 in peso e circa 3% in peso. A titolo di esempio vengono sotto riportati alcuni tra gli additivi utilizzati .
1. Antiossidanti
1.1 Monofenoli alchilati come, ad esempio: 2,6-dit-butil-4-metilfenolo; 2-t-butil-4,6-dimetilfenolo; 2,6-di-t-butil-4-etilfenolo; 2,6-di-t-butil-4-n-butilfenolo; 2,6-di-t-butil-4-isobutilfenolo; 2,6-diciclopentil-4-metilfenolo; 2-(α-metilcicloesil)-4.6-dimetilfenolo; 2,6-diottadecil-4-metilfenolo; 2.4.6-tricicloesilfenolo; 2,6-di-t-butil-4-metossimebilfenolo; nonilfenoli a catena alchilica lineare o ramificata quali, ad esempio, 2,6-di-nonil-4-metilfenolo; 2,4-dimetil-6-(1'-metilundec-1'-il)fenolo; 2,4-dimetil-6-(1'-metileptadec-1'-il)fenolo; 2,4-dimetil-6- (1'-metiltridec-1'-il)fenolo; e loro miscele .
1.2 Alchiltiometilfenoli come, ad esempio: 2,4-dicttiltiometil-6-t-butilfenolo; 2,4-diottiltiometil-6-metilfenolo; 2,4-diottiltiometil-6-etilfenolo; 2,6-didodeciltiometil-4-nonilfenolo.
1.3 Idrochinoni ed idrochinoni alchilati come, ad esempio: 2,6-di-t-butil-4-metossifenolo; 2,5-di-tbutilidrochinone; 2,5-di-t-amilidrochinone; 2,6-dìfenil-4-ottadecilossifenolo; 2,6-di-t-butilidrochinone; 2,5-di-t-butil-4-idrossianisolo; 3,5-di-t-butil-4-idrossianisolo; 3,5-di-t-butil-4-idrossifenil stearato; bis {3,5-di-t-butil-4-idrossifenil)adipato.
1.4 Tocoferoli come, ad esempio: α-tocoferolo, βtocoferolo, γ-tocoferolo, δ-tocoferolo e loro miscele (Vitamina E).
1.5 Eteri tiodifenilici idrossilati come, ad esempio: 2,2 '-tiobis-(6-t-butil-4-metilfenolo); 2,2'-tiobis-(4-ottilfenolo) ; 4,4'-tiobis-(6-t-butil-3-merilfenolo) ; 4,4'-tiobis-{6-t-butil-2-metilfenoloj; 4 ,4'-tiobis-(3,6-di-s-amilfenolo); 4,4'-bis-(2,6-dimetil-4-idrossifenil)disolfuro.
1.6 Alchiliden-bisfenoli come, ad esempio: 2,2'-metilenebis- (6-t-butil-4-metilfenolo); 2,2'-metilenebis- (6-t-butil-4-etilfenolo); 2,2'-metilenebis[4-met.il-6-(α-metilcicloesil)fenolo]; 2,2'-metilenebis (4-metil-6-cicloesilfenolo); 2,2'-metilenebis(6-nonil-4-metilfenolo) ; 2,2'-metilenebis(4,6-di-t-butilfenolo) ; 2,2'-etilidenebis(4,6-di-t-butilfenolo); 2,2'-etilidenebis(6-t-butil-4-isobutilfenolo); 2,2' -metilenebis[6-(α-metilbenzil)-4-nonilfenolo]; 2,2'-metilenebis[6-(a,α-dimetilbenzil)-4-nonilfenolo] ; 4,4'-metilenebis(2,6-di-t-butilfenolo); 4,4'-metilenebis (6-t-butil-2-metilfenolo); 1,1-bis-(5-t-butil-4-idrossi-2-metilfenil)butano; 2,6-bis-(3-L-butil-5-metil--2-idrossibenzil )-4-metilienolo; 1,1,3-tris- (5-t-butil--4-idrossi-2-metilfenil)butano; 1, 1-bis(5-t-butil-4-idrossi-2-metilfenil)-3-ndodecilmercaptobutano; etilenglicole bis[3,3-bis-(3'-t-butil-4 '-idrossifenil)butirrato]; bis(3-t-butil-4-idrossi-5-metilfenil)diciclopentadiene; bis-[2-(3'-t-butil-2 '-idrossi-5'-metilbenzil)--6--t-butil-4-metilienil]tereftalato; 1,1-bis(3,5-dimetil-2-idrossifenil)butano; 2,2-bis(3,5-di-t-butil— 4— idrossifenil)propano; 2,2-bis(5-t-butil-4-idrossi-2-metilfenil)-4-n-dodecilmercaptobutano; 1,1,5,5-tetra (5-t-butil-4-idrossi-2-metilfenil)pentano.
1.7 Composti benzilici contenenti 0, N o S come, ad esempio: 3,5,3',5'-tetra-t-butil-4,4'-diidrossidibenziletere; ottadecil-4-idrossi-3,5-dimetilbenzilmercaptoacetato; tridecil-4-idrossi-3,5-di-t-butilber.zilmercaptoacetato; tris(3,5-di-t-butil-4-idrossibenzil)ammina; bis(4-t-butil-3-idrossi-2,6-dimetilbenzil)ditiotereftalato; bis(3,5-di-t-butil-4-idrossibenzil )solfuro; isoottil-3,5-di-t-butil-4-idrossibenzilmercaptoacetato .
1.8 Maionati idrossibenzilati come, ad esempio: diottadecil-2,2-bis {3,5-di-t-butil-2-idrossibenzil)-maionato; diottadecil-2- (3-t-butil-4-idrossi-5-metilbenzil)maionato; didodecilmercaptoetil-2,2-bis-(3,5--di— t-butil-4-idrossibenzil)maionato; bis[4-(1,1,3,3-tetrametilbutil)fenil]— 2,2— bis(3,5-di-tbutil-4-idrossibenzil)maionato .
1.9 Composti idrossibenzilici aromatici come, ad esempio: 1,3,5-tris(3,5-di— t-butil— 4— idrossibenzil)-2,4,6-trimetilbenzene ; 1,4--bis--(3,5-di-t-butilidrossibenzil)-2,3,5,6-tetrametilbenzene; 2,4,6tris (3,5-di-t-butil-4-idrossibenzil) fenolo.
1.10 Composti triazinici come, ad esempio: 2,4-bis (ottilmercapto)-6- (3,5-di-t-butil-4-idrossiani — lino) -1,3,5-triazina; 2-ottilmercapto- 4 ,6-bis (3,5-di-t-butil-4-idrossianilino) -1,3, 5-triazina; 2-ottilmercapto-4 ,6-bis (3,5-di-t-butil-4-idrossifenos — si) -1,3,5-triazina; 2,4,6-tris-(3, 5-di-t-butil--4--idrossifenossi) -1,2,3-triazina; 1,3,5-tris (3,5-dit-butil-4-idrossibenzil) isocianurato; 1,3, 5-tris (4-t-butil-3-idrossi--2 ,6--dimetilbenzil )isocianurato ; 2, 4,6-tris- (3,5-di-t-butil-4-idrossif eniletil )-1,-3,5-triazina; 1,3,5-tris (3,5-di-t-butil-4 -idrossifenilpropionil) esaidro-1, 3,5-triazina; 1,3,5-tris-(3,5-dicicloesil-4-idrossibenzil) isocianurato.
1.11 Benzilfosfonati come, ad esempio: dimetil-2,5-di-t-butil-4-idrossibenzilfosfonato; dietil-3, 5-dit-butil-4-idrossibenzilfosfonato; diottadecil-3, 5-di-t-butil-4-idrossibenzilf osfonato; diottadecil-5-t-butil-4-idrossi-3-metilbenzilfosfonato; sali di calcio dell'estere monoetilico dell'acido 3,5-di-tbut.Ll-4-idrossibenzilf osf onico.
1.12 Acilamminof enoli come, ad esempio: 4-idrossilauranilide; 4-idrossistearanilide; ottil-N-(3,5-di-t-but il-4-idrossif enil )carbammato .
1.13 Esteri dell'acido β-(3,5-di-t-butil-4-idrossifenil)propionico con alcooli monoidrici o poliidrici come, ad esempio: metanolo, etanolo, n-ottanolo, i-ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, glicole neopentilico, glicole tiodietilenico, glicole dietilenico, glicole trietilenico, pentaeritritolo, tris(idrossietil) isocianurato, N,N'-bis-(idrossietil)ossalammide, 3-tioundecanolo, 3-tiopentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-1-fosfo— 2,6,7--triossabiciclo--[2.2.2]ottano.
1.14 Esteri dell'acido β-(5-t-butil-4-idrossi-3-metilfenil)propionico con alcooli monoidrici o poliidrici come, ad esempio: metanolo, etanolo, n-ottanolo, i-ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, glicole neopentilico, glicole tiodietilenico, glicole dietilenico, glicole trietilenico, pentaeritritolo, tris(idrossietil) isocianurato, N,N'-bis-(idrossietil)ossalammide, 3-tioundecanolo, 3-tiopentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-1-fosfo--2,6,7--triossabiciclo— [2.2.2]ottano .
1.15 Esteri dell'acido β-(3,5-dicicloesil-4-idrossifenil)propionico con alcooli monoidrici o poliidrici come, ad esempio: metanolo, etanolo, n-ottanolo, i-ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, glicole neopentilico, glicole tiodietilenico, glicole dietilenico, glicole trietilenico, pentaeritritolo, tris(idrossietil) isocianurato, Ν,Ν'-bis-(idrossietil)ossalammide, 3-tioundecanolo, 3-tiopentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-1-fosfo— 2,6,7--triossabiciclo--[2.2.2]ottano .
1.16 Esteri dell'acido 3,5-di-t-butil-4-idrossifenil)acetico con alcooli monoidrici o poliidrici come, ad esempio: metanolo, etanolo, n-ottanolo, iottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, glicole neopentilico, glicole tiodietilenico, glicole dietilenico, glicole trietilenico, pentaeritritolo, tris (idrossietil) isocianurato, N,N'-bis(idrossietil·)ossalammide, 3-tioundecanolo, 3-tiopentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil--1--fosfo-2 ,6,7-triossabiciclo[2.2.2]-ottano.
1.17 Ammidi dell'acido β-(3,5-di-t-butil-4-idrossifenil)propionico come, ad esempio: Ν,Ν'-bis(3,5-di-t-butil-4-idrossifenilpropionil) esametilenediammide; N,N '-bis (3,5-di-t-butil--4 — idrossifenilpropionil) trimetilenediammide; N,N' -bis(3,5--di-t-butil-4-idrossifenilpropionil )idrazide; N,N' -bis [2-(3- [3,5-di-t-butil-4-idrossifenil] propi onil--ossi )etil]ossammide (Naugard<® >XL-1 della Uniroyal).
1.18 Acido ascorbico (vitamina C).
1.19 Antiossidanti amminici come, ad esempio, Ν,Ν'-di-isopropil-p-fenilenediammina; N,Ν'-di-s-butil-pfenilenediammina ; N,N'-bis (1,4-dimetilpentil)-p-fenilenediammina ; N,N' -bis(1-etil-3-metilpentil) -pfenilenediammina; N, N'-bis (1-metileptil) -p-fenilenediammina; N,N'-dicicloesil-p-fenilenediammina; N,N' -difenil-p-fenilenediammina; N,N'-bis (2-naftil) -p-fenilenediammina ; N-isopropil-N' -fenil-pfenilenediammina; N- (1,3-dimetilbutil )-N' -fenil-pfenilenediammina; N- (1-metileptil) -N'-fenil-p-f enilenediammina ; N-cicloesil-N' -fenil-p-fenilenediammina; 4- (p-toluenesulfonammido) difenileneammina; N,Ν'—di-metil--N, N' --di-s-but il-p-fenilenediammina ; difenilammina; N-allildifenilammina; 4-isopropossidifenilammina; N-fenil-1-naf tilammina; N-(4-t-ottilfenil) -1-naftilammina; N-fenil-2-naftilammina; difenilammina ottilata quale, ad esempio, ρ,ρ'-dit-ot tildifenilammina; 4-n-butilamminof enolo; 4-butirrilamminofenolo; 4-nonanoilamminofenolo; 4-dodecanoilamminofenolo; 4-ottadecanoilammino fenolo; bis- (4-metossifenil)ammina; 2, 6-di-t-butil-4-dimetilaraminometilfenolo; 2,4'-diamminodifenilmetano; 4,4' -diamminodifenilmetano; N, N,N',N'-tetrametil-4,4' -diamminodifenilmetano; 1 ,2-bis[(2-metilfenil) -ammino] etano; 1,2-bis (fenilammino) propano; (o-tolil) biguanide; bis [4-(1',3'-dimetilbutil) fenil]-ammina; N-fenil-1-naftilammina t-ottilata; miscela di t-butil/t-ottildifenilammine mono- e dialchilate; miscela di nonildifenilammine mono- e dialchilate; miscela di dodecildifenilammine mono- e dialchilate; miscela di isopropil/isoesildifenilammine mono- e dialchilate; miscela di t-butil-di-f enìlammine mono- e dialchilate; 2,3-diidro-3 ,3-dimetil-4H-1, 4-benzotiazina; fenotiazina; miscela di tbutil/t-ottilf enotiazine mono- e dialchilate; miscela di t-ottil-fenotiazine mono- e dialchilate; N-allil-fenotiazina; N, N,N',N'-tetrafenil-1, 4-diamminobut-2-ene ; N,N-bis (2,2,6,6-tetrametil-piperid-4-i.L-esametilenediammina; bis (2,2,6,6-tetrametilpiperidin-4-il) sebacato; 2,2,6,6-tetrametilpiperidin-4-one; 2,2,6, 6-tetrametilpiperidin-4-olo .
2. Stabilizzanti ai raggi ultravioletti ed alla luce .
2.1 Derivati di 2- (2'-idrossifenil)benzotriazoli come, ad esempio: 2-(2'-idrossi-5'-metilfenil)benzoliriazolo; 2-(3',5'-di-t-butil-2'-idrossifenii)-benzotriazolo; 2-(5'-t-butil-2'-idrossifenii)benzotriazolo; 2-[2'-idrossi-5'-(1,1,3,3-tetrametilbutil)fenil]benzotriazolo ; 2-(3',5'--di-t-butil--2'— idrossifenii)-5-clorobenzotriazolo; 2-(3'-t-butil-2'--idrossi-5'-metilfenil)-5-clorobenzotriazolo; 2-(3'-s-butil-5 '-t-butil-2'-idrossifenii)benzotriazolo; 2- (2'-idrossi-4'-ottilossifenil)benzotriazo— lo; 2—{3',5'-di-t-amil-2'-idrossifenii)benzotriazolo; 2-[3',5'-bis(a,α-dimetilbenzil)-2'-idrossifenil]benzotriazolo; 2-[3'--t--butil— 2'--idrossi-5'-(2-ottilossicarboniletil)fenil)-5-cloro-benzotria--zolo; 2-[3'-t-butil-5'-(2-(2-etilesilossi)carboniletil)-2 '-idrossifenii]-5-clorobenzotriazolo; 2-[3'-t-butil--2 idrossi--5 '--(2-metossicarboniletil)fenil]-5-clorobenzotriazolo; 2-[3'-t-butil-2'-idrossi-5'- (2-metossicarboniletil)fenil]benzotriazolo; 2—[3’-t-butil-2'-idrossi— 5'--(2-ottilossicarboniletil)fenil]benzotriazolo; 2-[3'-t-butil-5'-(2-(2-etiiesilossi)carboniletil )--2'— idrossifenii)benzotriazolo; 2- (3'-dodecil-2'-idrossi-5'-metilfenil)-benzotriazolo; 2 -[3'-t-butil-2'-idrossi-5'-(2-isoottilossicarboniletil)fenil]benzotriazolo; 2,2'-metilenebis- [4-(1,1,3,3-tetrametilbutil)-6-benzotriazol-2-il-fenolo] ; prodotto di transesterificazione del 2- [3'-t-butil-5'-(2-metossicarboniletil)-2'-idrossifenil]-2H-benzotriazolo con il polietilene glicole 300;
[R-CH2CH2-COO-CH2CH2-]2- in cui R = 3'--t--butil-4'-idrossi-5 '-2H-benzotriazol-2-il-fenil; 2-[2'-idrossi-3'- (a,α-dimetilbenzil)— 5'--(1,1,3,3-tetrametilbutil)fenil]benzotriazolo; 2-[2’-idrossi-3'-(1,1,-3,3-tetrametilbutil)-5'- (a,α-dimetilbenzil)fenil]— benzotriazolo .
2.2 Benzotriazoli derivati dalla idantoina come quelli descritti, ad esempio, nelle domande di brevetto EP 867,435, WO 99/23093 e WO 99/37638.
2.3 Derivati di 2-idrossibenzofenoni come, ad esempio: 4-idrossi-; 4-metossi-; 4-ottilossi; 4-decilossi-; 4-dodecilossi-; 4-benzilossi-; 4,2’,4’-triidrossi-; 2'-idrossi-4,4'-dimetossi.
2.4 Esteri di acidi benzoici, opzionalmente sostituiti, come, ad esempio: fenil salicilato, 4-tbutilfenil salicilato, ottilfenil salicilato, benzoli resorcinolo, bis(4-t-butilbenzoil)resorcinolo, dibenzoil resorcinolo, 2,4-di-t-butilfenil-3,5-dit-butil-4-idrossibenzoato, esadecil-3,5-di-t-butil-4--idrossibenzoato, ottadecil— 3,5— di— t--butil-4-idrossibenzoato, 2-metil--4,6--di-t-butilfenil-3,5di-t-butil-4-idrossibenzoato .
2 .5 Acrilati come, ad esempio, etil od iso-ottil αcìano-β, β-difenilacrilato ; metil α-carbometossicinnamato, metil o butil α-ciano- -metil-p-metossicinnamato, metil α-carbometossi-p-metossicinnamato, N- (β-carbometossi- -cianovinil)-2-metilindolina .
2 .6 Composti del nichel come, ad esempio, Nicomplessi del 2,2 '-tio-bis- [4- (1,1,3,3-tetrametilbutil) fenolo] , ad esempio complessi 1:1 o 1:2, con o senza leganti addizionali come n-butilammina, trietanolammina o N-cicloesildietanolammina, nichel dibutilditiocarbammato, sali di nichel di esteri monoalchilici dell'acido 4-idrossi-3 ,5-di-t-butìlbenzilfosfonico, come esteri metilici o etilici, complessi del nichel con chetossime come 2-idrossì-4-metilfenil undecil chetossima, complessi del nichel di 1- fenil-4-lauroil-5-idrossipirazolo con o senza leganti addizionali.
2.7 Ammine sfericamente impedite e loro N-alcossi derivati come, ad esempio: poli-metilpropil-3-ossi-[4- (2,2,6,6-tetrametil) piperidinil] silossano, polimetilpropil-3-ossi- [4-(1,2,2,6, 6-pentametil )piperidinil ]silossano, bis- (2,2,6,6-t etrametil-4—piperidinil) sebacato; bis- {2,2,6,6-tetrametil-4-piperidinil) succinato; bis (1,2,2,6,6-pentametil-4-piperi-dinil)sebacato; bis(1-ottilossi-2,2,6,6—tetrametil-4-piperidinil )sebacato; bis(1,2,2,6,6-pentametil-4-piperidil)-n-butil-3, 5-di-t-butil-4-idrossibenzil--maionato; prodotto di condensazione tra la 1-(2-idirossietil)-2,2,6,6-tetrametil-4-idrossipiperidina e l'acido succinico; prodotto di condensazione, lineare o ciclico, tra la N,N'-bis(2,2,6,6-tetrametil-4-piperidil)esametilenediammina e la 4-tottilammino-2 ,6-dìcloro-1,3,5-s-triazina; tris-(2,2,6,6-tetrametil-4-piperidil)nitrilotriacetato; tetrakis (2,2,6,6-tetrametil-4-piperidil)--1,2,3,4--butanotetracarbossilato; 1,1'— (1,2— etanodiil)bis-(3,3,5,5-tetrametilpiperazinone; 4-benzoil-2,2,6,6-tetrametilpiperidina; 4-stearilossi-2,2,6,6-tetrametilpiperidina; bis(1,2,2,6,6— pentametilpiperi--dil)-2-n-butil-2- (2-idrossi-3,5-di-t-butilbenzil)--maionato; 3-n-ottil-7,7,9,9-tetrametil-1,3,8-triazaspiro[4 .5]decan-2,4-dione; bis(1--ottilossi--2.2.6.6-tetrametilpiperidil )sebacato; bis-(1-ottilossi-2,2,6,6-tetrametilpiperidil) succinato; prodotto di condensazione, lineare o ciclico, tra la N,N'-bis (2,2,6,6-tetrametil-4-piperidil)esametile— nediammina e la 4-morfolino-2,6-dicloro-1,3,5-triazina; prodotto di condensazione tra la 2-cloro-4.6-di-(4-n-butilammino— 2,2,6,6--tetrametilpiperidii) -1, 3, 5-triazina e 1 ' 1 , 2-bis ( 3 -ammiri oprop il animino)etano; prodotto di condensazione tra la 2-cloro-4,(J-di-(4-n-butilammino-1,2,2,6,6-pentametilpiperidil)-1,3,5-triazina e 1'1,2-bis{3-amminopropilaminino)etano; 8-acetil-3-dodecil-7,7,9,9-tetrametil-1,3,8-triazaspiro [4.5]decano-2,4-dione; 3-dodecil-1- (2,2,6,6-tetrametil-4-piperidil)pirrolidin-2,5-dione; 3-dodecil-1-{1,2,2,6,6-pentametil-4-piperidil)pirrolidin-2, 5-dione; miscela di 4-esadecilossi- e 4-stearilossi-2,2,6,6-tetrametilpiperidina; prodotto di condensazione tra l'N,N'-bis-(2,2,6,6-tetrametil-4 -piperidil)esametilenediammi--na e la 4-cicloesilammino-2,6-dicloro-1,3,5-triazina; prodotto di condensazione tra 1'1,2-bis(3-amminopropilammino)etano e la 2,4,6-tricloro-1,3,5-triazina, così come la 4-butilammino-2,2,6,6-tetrametilpiperidina (CAS Reg. No. [136504—96—6]; N- (2,2,6,6-tetrametil-4-piperidil)-n-dodecilsuccinìmmide; N- (1,2,2,6,6-pentametil-4-piperidil)-n-dodecilsuccinimmide; . 2-undecil-7,7,9,9-tetrametil-1-ossa-3,8-diaza-4-ossospiro [4,5]decano; prodotto di rea;:ione tra il 7,7,9,9-tetrametil-2-cicloundecill-ossa-3,8-diaza-4-ossospiro [4,5]decano e l'epicloridrina; 1,1-bis(1,2,2,6,6-pentametil-4-piperidilossicarbonil)— 2— (4-metossifenil)etene; N,N'-bis— formil-Ν,N'-bis(2,2,6, 6-tetrametil-4-piperidil)esametilenediammina ; diestere dell'acido 4-metossimetilenemalonico con la 1,2,2,6,6-pentametil-4-idrossipiperidina; prodotto di reazione del copolimero anidride maleica/α-olefina con la 2,2,6,6-tetrametil-4-amminopiperidina o con la 1,1,2,2,6-pentametil-4-amminopiperidina .
2.8 Ossammidi come, ad esempio: 4,4’-diottilossiossanilide; 2,2'-dietossiossanilide; 2,2'-diottilossi-5,5 '-di-t-butossanilide; 2,2'-didodecilossi-5,5'-di-t-butilossanilide; 2-etossi-2’-etilossanilide; N,N’-bis(3-dimetilamminopropil)ossammide; 2-etossi-5-t-butil-2 ’-etilossanilide e sue miscele con 2-etossi-2'-etil-5,4'-di-t-butossanilide; e miscele di orto- e para-metossi ossanilidi disostituite e miscele di orto- e para-etossi ossanilidi disostituite .
2.9 2- (2-idrossifenil)-1,3,5-triazine come, ad esempio: 2,4,6-tris(2-idrossi— 4--ottilossifenil)-1,3,5-triazina; 2-(2-idrossi-4-ottilossifenil)-4,6-bis (2,4-dimetilfenil)— 1,3,5--triazina; 2-(2,4-diidrossifenil)-4,6-bis (2,4-dimetilfenil)-1,3,5-triazina; 2,4-bis-(2-idrossi-4-propilossifenil)-6-(2,4-dimetilfenil)-1,3,5-triazina; 2-(2-idrossi-4-ottilossifenil)— 4,6--bis(4-metilienil)--1,3,5-triazina; 2-(2-idrossi-4-dodecilossifenil)-4, 6-bis(2,4-dime--tilfenil)-1,3,5-triazina; 2-[2-idrossi-4-(2-idrossi-— 3--butilossipropilossi)fenil]-4,6-bis(2,4-dimetiifenil)-1,3,5-triazina; 2-[2-idrossi-4-(2-idrossi-3-ottilossi-propilossi) fenil]-4,6-bis(2,4-dime--tilfenil)-1,3,5-triazina; 2-(2-idrossi-4-tridecilossifenil)-4,6-bis- (2,4-dimetilfenil)-1,3,5-triazina; 2-[4-(dodecilossi/tridecilossi-2-idrossipropossi)-2-idrossifenil]-4 ,6-bis(2,4-dimetilfenil)-1,3,-5-triazina; 2-[2-idrossi-4-(2-idrossi-3-dodecilossipropossi)fenil]-4 ,6-bis(2,4-dimetilfenil)-1,3,5--triazina; 2-(2-idrossi-4-esilossifenil)-4,6-difenil-1,3,5-triazina; 2-(2-idrossi-4-metossifenil)-4,6-difenil-1,3,5-triazina; 2,4,6-tris[2-idrossi--4- (3-butossi-2-idrossipropossi)fenil]-1,3,5-triazina; 2- (2-idrossifenil)-4-{4-metossiienil)-6-fenil-1,3,5-triazina; 2-{2-idrossi-4-[3-(2-etilesil-1-ossi)-2-idrossipropilossi]fenil }-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina .
3. "Metal-deactivators" come, ad esempio: N,N'-difenilossalammide, N-salicilal-N'-saliciloil-idrazina, N,N'-bis(saliciloil)idrazina, N,N'-bis{3,5-dit-butil-4-idrossifenilpropionil)idrazina, 3-saliciloilammino-1,2,4-triazolo, bis(benzilidene)ossallil diicrazide, ossanilide, isoftaloil diidrazide, sebacoil bisfenilidrazide, N,N'-diacetiladipoil diidrazide, N,N '-bis{saliciloil)ossallil diidrazide, N,N’-bis (saliciloil)tiopropionil diidrazide.
4. Fosfiti e fosfoniti come, ad esempio: trifenil fosfito, difenil alchil fosfiti, fenil dialchil fosfiti, tris(nonilfenil)fosfito, trilauril fosfito, trìottadecil fosfito, distearil pentaeritritol difosfito, tris(2,4-di-t-butilfenil)fosfito, diisodecil pentaeritritol difosfito, bis(2,4-di-t-butilfenil)pentaeritritol difosfito, bis(2,6-di-t-butil-4-ir.etilfenil)pentaeritritol difosfito, diisodecilossipentaeritritol difosfito, bis{2,4-di-t-butil-6-metilfenil)pentaeritritol difosfito, bis(2,4-dicumilfenil)pentaeritritol difosfito, bis[2,4,6-tris (t-butilfenil)]pentaeritritol difosfito, tristearil sorbitol trifosfito, tetrakis-(2,4-di-t-butilfenil)-4,4 ’-difenilenedifosfonito, 6-isoottilossi-2,4,8,10-tetra-t-butil-12H-dibenzo [d,g]-1,3,2-diossafosfocina, 6-fluoro-2,4,8,10-tetra-t-butil-12-metil-dibenzo [d,g]-1,3,2-diossafosfocina, bis-(2,4-di-t-butil-6-metilfenil)metilfosfito, bis(2,4-di----butil-6-metilfenil)etilfosfito; 2,2 ,2 -nitrito[trietil-tris (3,3',5,5'-tetra-t-butil-1,1'-bifenil-2,2'-diil)fosfito]; 2-etilesil-(3,3',5,5'-tetra--t-butil-1,1'-bifenil-2,2'-diil)fosfito.
5. Idrossilammine come, ad esempio: N,N-dibenzilidrossilammina; N ,N-dietilidrossilammina; N,N-diottilidrossilammina; N,N-dilaurilidrossiiammina; N,N-ditetradecilidrossilammina , N,N-diesadecilidrossilammina; N,N-diottadecilidrossilammina ; N-esadecil-N-ottadecilidrossilammina; N-eptadecil-N-ottadecilidrossilammina; N,N-dialchilidrossilammine derivate dalle ammine del sego idrogenate.
6. Nitroni come, ad esempio: N-benzil-α-fenilnitrone; N-etil-α-metil-nitrone; N-ottil-α-eptilnitrone; N-lauril-α-undecil-nitrone; N-tetradecilα-tridecil-nitrone; N-esadecil-α-pentadecil-nitrone; N-ottadecil-α-eptadecil-nitrone; N-esadecil-αeptadecil-nitrone ; N-ottadecil-α-pentadecil-nitrone; N-eptadecil-α-eptadecil-nitrone; N-ottadecil-αesadecil-nitrone; nitroni derivati dalle ammine del sego idrogenate.
7. Tiosinergisti come, ad esempio: dilauril tiodipropionato; distearil tiodipropionato.
8. Agenti che sono in grado di distruggere i perossidi come, ad esempio, esteri dell'acido βtiodipropionico come lauril, stearil, miristil o tridecil esteri, mercaptobenzìmidazolo o sale di zinco del 2-mercaptobenzimidazolo, zinco dibutilditiocarbammato, diottadecildisolfuro, pentaeritritol tetrakis (β-dodecilmercapto) propionato .
9. Stabilizzanti della poliammide come, ad esempio, sali di rame in combinazione con composti del-lo iodio e/o del fosforo, sali del manganese divalente .
10. Co-stabilizzanti basici come, ad esempio: melammina, polivinilpirrolidone, dicianodiammide, triallil cianurato, derivati dell'urea, derivati dell 'idrazina, ammine, poliammidi, poliuretani, sali dei metalli alcalini e sali dei metalli alcalino-terrosi di acidi grassi ad elevato peso molecolare come, ad esempio, Ca-stearato, Zn-stearato, Mg-stearato, Mg-behenato, Na-ricinoleato, K-palmitato, antimonio-pirocatecolato, stagno-pirocatecolato, zinco-piracatecolato .
11. Agenti nucleanti come, ad esempio: sostanze inorganiche quali talco, ossidi metallici (ad esempio, diossido di titanio od ossido di magnesio) , fosfati, carbonati o solfati (preferibilmente di metalli alcalino-terrosi) ; composti organici quali acidi mono- o policarbossilici e loro sali (ad esempio, acido 4-t-butilbenzoico, acido adipico, acido difenilacetico, succinato di sodio, benzoato di sodio); composti polimerici quali copolimeri ionici ("ionomers") .
12 . Cariche ed agenti rinforzanti come, ad esempio: carbonato di calcio, silicati, fibre di vetro, perline di vetro ("glass beads"), amianto, talco, caolino, mica, solfato di bario, ossidi ed idrossidi metallici, nero fumo, grafite, farina di legno e farine o fibre di altri prodotti naturali, fibre sintetiche .
13. Altri additivi come, ad esempio: plastificanti, pi menti, lubrificanti, emulsionanti, additivi reologici, catalizzatori, agenti di scivolamento, brillantanti ottici, agenti antifiammma (ad esempio, bromurati, clorurati, fosforati e misti fosforo/alogeni) , agenti antistatici, agenti di espansione .
11. Benzofuranoni ed indolinoni come, ad esempio : 3- [4- (2-acetossietossi) fenil]-5,7-di-t-butil-benzofuran-2-one; 5,7-di-t-butil-3- [4-(2-stearoilossietossi) fenil]ben zofuran-2-one; 3,3'-bis [5,7-di-tbutil--3-- [4-(2-idrossietossi )fenil] benzofuran--2--one] ; 5,7-di-t-butil-3- (4-etossifenil )benzo furand -one; 3- (4-acetossi-3, 5-dimetilf enil)-5, 7-di-t-butil-benzofuran-2-one; 3- (3,5-dimetil-4-pivaloilossifenil) -5,7-di-t-butil-benzof uran-2-one ; oppure quelli descritti nei brevetti USA No. 4,325,863, 4,338,244, 5,175,312, 5,216,052 e 5,252,643; nei be vetti tedeschi DE 4,316,611, 4,316,622 e 4,316,876; o nelle domande di brevetto europeo No.
589,839 e 591,102.
I composti appartenenti alla classe delle animine stericamente impedite aventi formula generale (I), tal quali od in miscela tra loro, eventualmente in presenza di altri additivi, possono essere incorporati facilmente nei polimeri organici da stabilizzare attraverso le convenzionali tecniche. Detta incorporazione può avvenire prima o durante la formazione del manufatto finale, ad esempio, miscelando i composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I), sottoforma di liquidi o di scaglie, con il polimero organico da stabilizzare, oppure aggiungendo detti composti al polimero da stabilizzare fuso od in soluzione, oppure applicando una soluzione od una sospensione di detti composti al polimero da stabilizzare, eventualmente evaporando il solvente utilizzato. Gli elastomeri possono essere stabilizzati come lattici. Un altro metodo per incorporare i composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) comprende l'aggiunta degli stessi prima o durante la polimerizzazione dei corrispondenti monomeri o prima della reticolazione.
I composti appartenenti alla classe delle arumine stericamente impedite aventi formula generale (I) o loro miscele, possono essere aggiunti al polimero da stabilizzare anche sottoforma di "masterbatch" che comprende detti composti in concentrazione compresa, ad esempio, tra 2,5% e 25% in peso.
Le composizioni polimeriche stabilizzate come sopra descritto, possono essere convertite in prodotti finiti come, ad esempio, fibre, films, nastri, fogli, fogli a più strati, contenitori, tubi ed altre forme, attraverso metodi noti nell'arte quali, ad esempio, "casting", stampaggio a caldo, filatura, estrusione o stampaggio ad iniezione.
Allo scopo di meglio comprendere la presente invenzione e per mettere in pratica la stessa, vengono di seguito riportati alcuni esempi illustrativi ma non limitativi della presente invenzione.
ESEMPIO 1
Preparazione del composto avente formula (Ib'):
In un pallone a tre colli munito di agitatore meccanico, di colonna "Vigreux" con prelievo di testa, di termometro e di gocciolatore, vengono caricati 20 g di 1-idrossietil-2, 2,6, 6-tetrametil piperidinolo (0,0995 moli) e 150 g di dimetil carbonato (1,666 moli).
La suddetta miscela viene mantenuta sotto agitazione meccanica e portata a 50°C in 30 minuti ed additivata con 1,12 g di una soluzione al 20% di inetilato di sodio: si ottiene così, velocemente, la dissoluzione del solido residuo.
La miscela ottenuta come sopra descritto, viene portata alla temperatura di ebollizione della soluzione dimetil carbonato/metanolo (temperatura della testa 63°C) e viene sottoposta a distillazione azeotropica fino a che la temperatura della caldaia raggiunge i 90°C. La quantità di azeotropo è pari a 28,3 g (quantità' superiore al teorico).
Mediante analisi gas-cromatografica si verifica la scomparsa sia del prodotto di partenza, l'1-idrossietil-2, 2-6,6-tetrametilpiperidinolo sia del suo monoestere carbonico.
Al termine della reazione, la miscela così ottenuta viene filtrata a 60°C su filtro statico (porosità G-4) e, successivamente, il filtrato ottenuto, una volta portato a temperatura ambiente, viene lavato con 68,5 g di acqua ottenendosi una fase organica ed una fase acquosa: la fase organica viene viene sottoposta ad evaporazione sottovuoto.
Si ottengono 28,8 g di prodotto liquido lievemente giallino (91% di resa) corrispondente al Composto avente formula (Ib')·
Claims (19)
- RIVENDICAZIONI 1. Composti appartenenti alla classe delle ammine stericamente impedite, costituiti da miscele di monomeri e/o oligomeri di esteri carbonici di un idrossi-alchil-2, 2,6,6-tetrametil-piperidinolo, aventi formula generale (I):in cui: R1 rappresenta un atomo di idrogeno; un gruppo alchilico C1-C6 lineare o ramificato; un gruppo arilico C6-C12; m è 1 o 2; R2 rappresenta un gruppo -OCOOR1 in cui R1 ha gli stessi significati sopra descritti; oppure rappresenta un gruppo idrossilico; n rappresenta un numero intero compreso tra 1 e 9 estremi inclusi.
- 2. Composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) secondo la rivendicazione 1, in cui i gruppi alchilici C1-C6 lineari o ramificati sono: metile, etile, propile, t-butile.
- 3. Composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) secondo la rivendicazione 1, in cui i gruppi arilici C6-C12 sono: fenile, naftile.
- 4. Composto appartenente alla classe delle ammine stericamente impedite aventi formula generale (I) secondo la rivendicazione 1, avente formula (la):in cui n è un numero intero compreso tra 1 e 6 estremi inclusi.
- 5. Composto appartenente alla classe delle ammine stericamente impedite aventi formula generale (I) secondo la rivendicazione 1, avente formula (Ib):in cui n è un numero intero compreso tra 1 e 6 estremi inclusi.
- 6. Procedimento per la preparazione dei composti appartenenti alla classe delle delle animine stericamente impedite aventi formula generale (I) secondo una qualsiasi delle rivendicazioni precedenti, comprendente la reazione di esterificazione di un idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II): in cui R2 ed m hanno gli stessi significati sopra descritti, con un dialchil carbonato avente formula generale (III):in cui R1 ha gli stessi significati sopra descritti, in presenza di una base come catalizzatore, eventualmente in presenza di un solvente organico inerte scelto tra i solventi aromatici, ad una temperatura compresa tra 50°C e 200°C, per un tempo compreso tra 2 ore e 12 ore .
- 7. Procedimento secondo la rivendicazione 6, in cui la base è metilato di sodio.
- 8. Procedimento secondo la rivendicazione 6 o 7, in cui il solvente organico inerte è toluene o clorobenzene .
- 9. Procedimento secondo una qualsiasi delle rivendicazioni da 6 a 8, in cui la temperatura è compresa tra 50°C e 140°C.
- 10. Procedimento secondo una qualsiasi delle rivendicazioni da 6 a 9, in cui il tempo è compreso tra 6 ore ed 8 ore.
- 11. Procedimento secondo una qualsiasi delle rivendicazioni da 6 a 10, in cui l'idrossi-alchil-2 ,2,6,6-tetrametil-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) vengono utilizzati in rapporto molare compreso tra 4:1 e 20:1, ottenendosi composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) secondo una qualsiasi delle rivendicazioni da 1 a 5, in cui n è 1, oppure miscele liquide di detti composti a basso contenuto di oligomeri in cui n è compreso tra 1 e 3 estremi inclusi .
- 12. Procedimento secondo la rivendicazione 11, in cui l'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) vengono utilizzati in rapporto molare 17:1.
- 13. Procedimento secondo una qualsiasi delle rivendicazioni da 6 a 10, in cui l'idrossi-alchil-2,2,6,6-tetrametil-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) vengono utilizzati in rapporto molare compreso tra 1:1 e 1:2, ottenendosi miscele di composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) secondo una qualsiasi delle rivendicazioni da 1 a 5, in cui n è compreso tra 4 e 9 estremi inclusi.
- 14. Procedimento secondo la rivendicazione 13, in cui l'idrossi-alchil-2,2,6,6-tetrametri-piperidinolo avente formula generale (II) ed il dialchil carbonato avente formula generale (III) vengono utilizzati in rapporto molare 1:1.
- 15. Composizioni polimeriche contenenti un polimero organico ed una quantità efficace di uno o più composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) di cui ad una qualsiasi delle rivendicazioni precedenti.
- 16. Composizioni polimeriche secondo la rivendicazione 15, in cui composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) sono utilizzati in combinazione con altri stabilizzanti.
- 17. Composizioni polimeriche secondo la rivendicazione 15 o 16, in cui il polimero organico è scelto tra le poliolefine.
- 18. Manufatti ottenuti dalla lavorazione delle composizioni polimeriche di cui ad una qualsiasi delle rivendicazioni da 15 a 17.
- 19. Uso dei composti appartenenti alla classe delle ammine stericamente impedite aventi formula generale (I) di cui ad una qualsiasi delle rivendicazioni da 1 a 14, tal quali od in miscela tra loro, come stabilizzanti alla luce per polimeri organici.
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IT2000MI000326A IT1317848B1 (it) | 2000-02-23 | 2000-02-23 | Composti appartenenti alla classe delle ammine stericamente impedite,procedimento per la loro preparazione e loro utilizzo, quali |
PCT/EP2001/001816 WO2001062730A1 (en) | 2000-02-23 | 2001-02-19 | Compounds belonging to the group of sterically hindered amines, process for their preparation and their use as light stabilizers in organic polymers |
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IT2000MI000326A IT1317848B1 (it) | 2000-02-23 | 2000-02-23 | Composti appartenenti alla classe delle ammine stericamente impedite,procedimento per la loro preparazione e loro utilizzo, quali |
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ITMI20000326A0 ITMI20000326A0 (it) | 2000-02-23 |
ITMI20000326A1 true ITMI20000326A1 (it) | 2001-08-23 |
IT1317848B1 IT1317848B1 (it) | 2003-07-15 |
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US20090111699A1 (en) * | 2004-03-02 | 2009-04-30 | Adeka Corporation | Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions |
JP5656213B2 (ja) * | 2010-01-19 | 2015-01-21 | 日本化薬株式会社 | カルボン酸組成物、及び該カルボン酸組成物を含有する硬化性樹脂組成物 |
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JPS5943061A (ja) * | 1982-09-06 | 1984-03-09 | Adeka Argus Chem Co Ltd | 安定化合成樹脂組成物 |
JP2602264B2 (ja) * | 1988-02-01 | 1997-04-23 | シーアイ化成 株式会社 | 農業用オレフイン系樹脂フイルム |
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ITMI20000326A0 (it) | 2000-02-23 |
IT1317848B1 (it) | 2003-07-15 |
WO2001062730A1 (en) | 2001-08-30 |
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