CN1294193C - 用于着色聚烯烃的紫外吸收剂增效组合物 - Google Patents
用于着色聚烯烃的紫外吸收剂增效组合物 Download PDFInfo
- Publication number
- CN1294193C CN1294193C CNB031198368A CN03119836A CN1294193C CN 1294193 C CN1294193 C CN 1294193C CN B031198368 A CNB031198368 A CN B031198368A CN 03119836 A CN03119836 A CN 03119836A CN 1294193 C CN1294193 C CN 1294193C
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- Prior art keywords
- alkyl
- carbon atom
- phenyl
- group
- tetramethyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 45
- 239000006096 absorbing agent Substances 0.000 title abstract description 9
- 230000002195 synergetic effect Effects 0.000 title description 2
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 16
- YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 claims abstract description 11
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004611 light stabiliser Substances 0.000 claims abstract description 10
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- 150000001721 carbon Chemical group 0.000 claims description 171
- 229910052799 carbon Inorganic materials 0.000 claims description 171
- 125000000217 alkyl group Chemical class 0.000 claims description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 239000000049 pigment Substances 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 74
- 229910052757 nitrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 31
- 238000010521 absorption reaction Methods 0.000 claims description 29
- 125000001118 alkylidene group Chemical group 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 239000004743 Polypropylene Substances 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 9
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- GXFQBBOZTNQHMW-UHFFFAOYSA-N n'-(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound CC1(C)CC(NCCCCCCN)CC(C)(C)N1 GXFQBBOZTNQHMW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 claims description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
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- 239000002253 acid Substances 0.000 claims description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 6
- 150000004056 anthraquinones Chemical class 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 5
- 229940038384 octadecane Drugs 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- ULVDMKRXBIKOMK-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2,3-dihydroisoindol-1-one Chemical compound ClC1=C(Cl)C(Cl)=C2CNC(=O)C2=C1Cl ULVDMKRXBIKOMK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 3
- 125000006839 xylylene group Chemical group 0.000 claims description 3
- MEEHIBIOOFBRDM-UHFFFAOYSA-N 1-(2,2,6,6-tetramethylpiperidin-4-yl)butane-1,2,3,4-tetracarboxylic acid Chemical class CC1(C)CC(C(C(C(CC(O)=O)C(O)=O)C(O)=O)C(O)=O)CC(C)(C)N1 MEEHIBIOOFBRDM-UHFFFAOYSA-N 0.000 claims description 2
- KTNPVRSKFWZJEZ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-1-amine Chemical compound CC1(C)CCCC(C)(C)N1N KTNPVRSKFWZJEZ-UHFFFAOYSA-N 0.000 claims description 2
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 claims description 2
- PMRTXCQELXDQEH-UHFFFAOYSA-N 2-[carboxymethyl-[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetic acid Chemical compound CC1(C)CC(OC(=O)CN(CC(O)=O)CC(O)=O)CC(C)(C)N1 PMRTXCQELXDQEH-UHFFFAOYSA-N 0.000 claims description 2
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- GHUDTURWNYDCKX-UHFFFAOYSA-N 4-oxo-4-(2,2,6,6-tetramethylpiperidin-4-yl)oxybutanoic acid Chemical compound CC1(C)CC(OC(=O)CCC(O)=O)CC(C)(C)N1 GHUDTURWNYDCKX-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 2
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims description 2
- ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims 3
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- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 abstract description 3
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical compound OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 abstract description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本发明涉及聚烯烃组合物,其中含有:a)至少一种有机颜料,b)至少一种位阻胺光稳定剂和c)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物。本发明的其它方面是一种稳定着色聚烯烃的方法和使用羟苯基苯并***与羟苯基-s-三嗪的混合物作为UV吸收剂稳定着色聚烯烃。
Description
本发明涉及聚烯烃组合物,其中包含羟苯基苯并***和羟苯基-s-三嗪UV吸收剂的混合物,至少一种位阻胺类光稳定剂(HALS)和至少一种有机颜料。本发明的其它对象是用于稳定着色聚烯烃的方法和紫外吸收剂混合物的应用。
大气中的氧、水分,特别是紫外线的作用,造成了聚合物材料的降解。这表现为,例如,机械强度减小、色调改变和聚合物制品的最终完全破坏。正如已知的,使用合适的稳定剂可以延缓聚烯烃的这些降解过程,这一领域已有许多先有技术文献。
在涂布领域,EP-A-0453396披露,羟苯基苯并***与羟基二苯酮或与羟苯基-s-三嗪紫外吸收剂混合会产生增效作用,这出乎意料地长期防止涂料降解。
FR 2619814一般地公开了草酰胺UV吸收剂与二苯酮或苯并***UV吸收剂的结合使用,尤其是在涂料中,但在该先有技术中未提出在聚烯烃中的本发明组合物。
GB 2361005公开了聚烯烃中的几种UV吸收剂组合物,但未提及苯并***与羟苯基三嗪的组合。
现已发现,苯并***与羟苯基三嗪紫外吸收剂在位阻胺光稳定剂存在下组合,能显著地阻止着色聚烯烃的降解。
本发明的组合物提供了出乎意料的对聚烯烃制品的增效稳定作用。此效应无法由吸收光谱预见,而且至今未曾在着色聚烯烃中的其它紫外吸收剂组合物中观察到这一效应。
本发明的一个方面是一种聚烯烃组合物,其中含有
a)至少一种有机颜料,
b)至少一种位阻胺光稳定剂,和
c)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物。
合适的聚烯烃叙述如下。
1.单烯烃和双烯烃的聚合物,例如,聚丙烯、聚异丁烯、聚丁-1-烯、聚-4-甲基戊-1-烯、聚异戊二烯或聚丁二烯,以及环烯烃聚合物,例如环戊烯或降冰片烯的聚合物;聚乙烯(可任选地交联),例如高密度聚乙烯(HDPE)、高密度高分子量聚乙烯(HDPE-HMW)、高密度超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、(VDPE)和(ULDPE),金属茂聚乙烯(m-PE)(特别是m-LLDPE)和金属茂聚丙烯(m-PP)。
聚烯烃,即,上段中列举的单烯烃的聚合物,优选聚乙烯和聚丙烯,可以用不同的方法,特别是用以下方法制备:
a)辐射聚合(通常在高压和高温下)。
b)使用催化剂的催化聚合,催化剂中通常含一种或多种周期表中IVb、Vb、VIb或VIII族金属。这些金属通常有一或多个配体,一般为氧化物、卤化物、醇化物、酯类、醚类、胺类、烷基、链烯基和/或芳基,它们可以是π-或σ-配位的。这些金属配合物可以是自由形式或是固定在载体上,一般是在活化的氯化镁、氯化钛(III)、氧化铝或氧化硅上。这些催化剂在聚合介质中可以溶解或不溶解。催化剂可以是本身用于聚合反应,或是可以使用其它的活化剂,通常是金属烷基化物、金属氢化物、金属烷基卤化物、金属烷基氧化物或金属烷基烷,该金属是周期表中Ia、IIa和/或IIIa族元素。活化剂可以方便地用其它的酯、醚、胺或甲硅烷基醚基改性。这些催化剂体系通常被称作Phillips(Standard Oil Indiana)、Ziegler(-Natta)、TNZ(DuPont)、金属茂或单位点催化剂(SSC)。
2.1)中叙述的聚合物的混合物,例如聚丙烯与聚异丁烯、聚丙烯与聚乙烯(例如PP/HDPE、PP/LDPE)的混合物,不同类型聚乙烯(例如LDPE/HDPE)的混合物,金属茂型与常规类型的混合物(例如m-PE/PE-LLD,m-PE/PE-LD,m-PP/常规PP)。
优选聚烯烃组合物中的聚烯烃是聚丙烯、聚乙烯或其共聚物。
特别优选的聚烯烃组合物中聚烯烃为聚丙烯或其共聚物。
在“Gchter/Müller:Plastics Additives Handbook,第3版,HanserPublishers,Munich Vienna New York”一书647-659页,11.2.1.1至11.2.4.2中所述的所有有机颜料均可作为组分a)使用。其它合适的颜料在H.Zweifel编著的“Plastics Additives Handbook”第5版中有叙述。
有机颜料的实例是偶氮颜料、蒽醌类、苯并咪唑酮类、二嗪类、酞菁类、四氯异吲哚啉酮类、喹吖啶酮类、异吲哚啉类、苝类、吡咯并吡咯(二酮基吡咯并吡咯,例如颜料红254)。
这些有机颜料的实例有:
C.I.(染料索引)颜料黄93,颜料黄95,颜料黄138,颜料黄139,颜料黄155,颜料黄162,颜料黄168,颜料黄180,颜料黄183,颜料红44,颜料红170,颜料红202,颜料红214,颜料红254,颜料红264,颜料红272,颜料红48:2,颜料红48:3,颜料红53:1,颜料红57:1,颜料绿7,颜料蓝15:1,颜料蓝15:3和颜料紫19。
很合适的一类是例如二酮基吡咯并吡咯颜料。
有机和无机颜料的混合物也在本发明的范围之内。一种特别优选的无机颜料是二氧化钛,它经常与有机颜料组合使用。
当使用有机与无机颜料的混合物时,有机颜料与无机颜料之比可以在很宽的范围内变化,一般是重量比由5∶95至95∶5。
掺入的颜料量一般为聚合物重量的0.1-15%,优选0.1-10%,更优选为0.1-5%。
典型的羟苯基三嗪类紫外吸收剂是式(I)化合物
其中n是1或2;
R1、R′1、R2和R′2彼此独立地是H,OH,C1-C12烷基,C2-C6链烯基,C1-C12烷氧基,C2-C18烯氧基,卤素,三氟甲基,C7-C11苯基烷基,苯基,被C1-C18烷基、C1-C18烷氧基或卤素取代的苯基,苯氧基,或被C1-C18烷基、C1-C18烷氧基或卤素取代的苯氧基;
R3和R4彼此独立地是H,C1-C12烷基,OR′7,C2-C6链烯基,C2-C18烯氧基,卤素,三氟甲基,C7-C11苯基烷基,苯基,被C1-C18烷基、C1-C18烷氧基或卤素取代的苯基,苯氧基,或被C1-C18烷基、C1-C18烷氧基或卤素取代的苯氧基;
R6是氢,C1-C24烷基,C5-C12环烷基或C7-C15苯基烷基;
R7在n=1的情形和R′7彼此独立地是氢或C1-C18烷基;或者是被下述基团取代的C1-C12烷基:OH,C1-C18烷氧基,烯丙氧基,卤素,-COOH,-COOR8,-CONH2,-CONHR9,-CON(R9)(R10),-NH2,-NHR9,-N(R9)(R10),-NHCOR11,-CN,-OCOR11,苯氧基和/或被C1-C18烷基、C1-C18烷氧基或卤素取代的苯氧基;或者R7是被-O-间断并可被OH取代的C3-C50烷基;或者R7是C3-C6链烯基;缩水甘油基;被OH、C1-C4烷基或-OCOR11取代的C5-C12环烷基;未被取代的或被OH、Cl或CH3取代的C7-C11苯基烷基;-CO-R12或-SO2-R13;
R7在n=2的情形是C2-C16亚烷基、C4-C12亚烯基、亚二甲苯基,被O间断和/或被OH取代的C3-C20亚烷基,或者是基团CH2CH(OH)CH2O-R20-OCH2CH(OH)CH2-、-CO-R21-CO-、-CO-NH-R22-NH-CO或-(CH2)m-COO-R23-OOC-(CH2)m-,其中m是从1到3的数字,或者是
R8是C1-C18烷基;C2-C18链烯基;羟乙基;C3-C50烷基,该烷基被O、NH、NR9或S间断和/或被OH取代;被-P(O)(OR14)2、-N(R9)(R10)或-OCOR11和/或OH取代的C1-C4烷基;缩水甘油基;C5-C12环烷基;苯基;C7-C14烷基苯基或C7-C11苯基烷基;
R9和R10彼此独立地是C1-C12烷基,C3-C12烷氧基烷基,C4-C16二烷基氨基烷基或C5-C12环烷基,或者R9和R10合起来是C3-C9亚烷基或氧杂亚烷基或氮杂亚烷基;
R11是C1-C18烷基、C2-C18链烯基或苯基,C2-C12羟烷基,环己基,或是被-O-间断并可被OH取代的C3-C50烷基;
R12是C1-C18烷基,C2-C18链烯基,苯基,C1-C18烷氧基,C3-C18烯氧基,被O、NH、NR3或S间断和/或被OH取代的C3-C50烷氧基,环己氧基,C7-C14烷基苯氧基,C7-C11苯基烷氧基,苯氧基,C1-C12烷基氨基,苯基氨基,甲苯氨基或萘氨基;
R13是C1-C12烷基,苯基,萘基或C7-C14烷基苯基;
R14是C1-C12烷基,甲基苯基或苯基;
R20是C2-C10亚烷基,被O间断的C4-C50亚苯基,亚苯基或-亚苯基-X-亚苯基-,其中X是-O-、-S-、-SO2-、-CH2-或-C(CH3)2;
R21是C2-C10亚烷基,C2-C10氧杂亚烷基,C2-C10硫杂亚烷基,C6-C12亚芳基或C2-C6亚烯基;
R22是C2-C10亚烷基,亚苯基,亚甲苯基,二亚苯基甲烷,或以下基团
R23是C2-C10亚烷基或被O间断的C4-C20亚烷基。
在所有情形,卤素均为氟、氯、溴或碘。
烷基的实例是甲基、乙基、丙基、异丙基、正丁基、、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1,1,3-三甲基乙基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基。
有最多达12个碳原子的烷氧基是甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、戊氧基、异戊氧基、己氧基、庚氧基、辛氧基、癸氧基、十二烷氧基。
烯氧基的实例是丙烯氧基、丁烯氧基、戊烯氧基和己烯氧基。
C5-C12环烷基的实例是环戊基、环己基、环庚基、环辛基和环十二烷基。优选C5-C8环烷基,尤其是环己基。
C1-C4烷基取代的C5-C12环烷基是例如甲基环己基或二甲基环己基。
OH-和/或C1-C10烷基取代的苯基是例如甲基苯基、二甲基苯基、三甲基苯基、四丁基苯基或3,5-二叔丁基-4-羟基苯基。
烷氧基取代的苯基是例如甲氧基苯基、二甲氧基苯基或三甲氧基苯基。
C7-C9苯基烷基的实例是苄基和苯乙基。
在苯基上被-OH和/或最多达10个碳原子的烷基取代的C7-C9苯基烷基是例如甲基苄基、二甲基苄基、三甲基苄基、叔丁基苄基或3,5-二叔丁基-4-羟基苄基。
链烯基的实例是烯丙基、2-甲基烯丙基、丁烯基、戊烯基和己烯基。优选的是烯丙基。位置1上的碳原子优选是饱和的。
亚烷基的实例是亚甲基、亚乙基、亚丙基、1,3-亚丙基,1,4-亚丁基,1,5-亚戊基,2,2-二甲基-1,3-亚丙基,1,6-亚己基,三甲基-1,6-亚己基,1,8-亚辛基和1,10-亚癸基。
亚烯基的实例是亚丁烯基、亚戊烯基和亚己烯基。
C6-C12亚芳基优选是亚苯基。
被O间断的烷基是例如-CH2-CH2-O-CH2-CH3、-CH2-CH2-O-CH3或-CH2-CH2-O-CH2-CH2-CH2-O-CH2-CH3-。它优选由聚乙二醇衍生形成。通用的表示是-((CH2)a-O)b-H/CH3,其中a是从1到6的数字,b是从2到10的数字。
C2-C10氧杂亚烷基和C2-C10硫杂亚烷基可以由上述的亚烷基通过用氧原子或硫原子取代一个或多个碳原子得到。
在本发明的一项具体实施方案中,羟苯基三嗪UV吸收剂具有以下化学式(Ia)
其中
u是1或2,r是整数1-3,取代基Y1彼此独立地是氢、羟基、卤代甲基、有1-12个碳原子的烷基、有1-18个碳原子的烷氧基、苯基或卤素;
如果u是1,则Y2是有1-18个碳原子的烷基;未取代的或被羟基、有1-18个碳原子的烷氧基或卤素取代的苯氧基,或被各有1-18个碳原子的烷基或烷氧基取代或卤素取代的苯氧基;有1-12个碳原子并被-COOH、-COOY8、-CONH2、-CONHY9、-CONY9Y10、-NH2、-NHY9、-NY9Y10、-NHCOY11、-CN和/或-OCOY11取代的烷基;被一个或多个氧原子间断的未取代或被羟基或1-12个碳原子的烷氧基取代的4-20个碳原子的烷基;有3-6个碳原子的链烯基;缩水甘油基;未被取代的或被羟基、1-4个碳原子的烷基和/或-OCOY11取代的环己基,烷基部分有1-5个碳原子的未被取代或被羟基、氯和/或甲基取代的苯基烷基,-COY12或-SO2Y3,或
如果u是2,则Y2是有2-16个碳原子的亚烷基;4-12个碳原子的亚烯基;亚二甲基苯基;3-20个碳原子的亚烷基,该亚烷基被一个或多个-O-原子间断并且/或被羟基取代;-CH2CH(OH)CH2-O-Y15-OCH2CH(OH)CH2,-CO-Y16-CO-,-CO-NH-Y17-NH-CO-或-(CH2)m-CO2-Y18-OCO-(CH2)m,其中m是1、2或3;
Y8是有1-18个碳原子的烷基,3-18个碳原子的链烯基,被一个或多个氧或硫原子或-NT6-间断并且/或被羟基取代的3-20个碳原子的烷基,被P(O)(OY14)2、-NY9Y10或-OCOY11及/或羟基取代的1-4个碳原子的烷基,3-18个碳原子的链烯基,缩水甘油基,或在烷基部分有1-5个碳原子的苯基烷基;
Y9和Y10彼此独立地是有1-12个碳原子的烷基,3-12个碳原子的烷氧基烷基,4-16个碳原子的二烷基氨基烷基,或5-12个碳原子的环烷基,或者Y9和Y10合起来是各有3-9个碳原子的亚烷基、氧杂亚烷基或氮杂亚烷基;
Y11是有1-18个碳原子的烷基、有2-18个碳原子的链烯基,或是苯基;
Y12是有1-18个碳原子的烷基,有2-18个碳原子的链烯基,苯基,有1-12个碳原子的烷氧基,苯氧基,1-12个碳原子的烷氨基或苯氨基。
Y13是有1-18个碳原子的烷基,苯基,或烷基部分有1-8个碳原子的烷基苯基;
Y14是有1-12个碳原子的烷基,或苯基;
Y15是有2-10个碳原子的亚烷基,亚苯基,或是基团-亚苯基-M-亚苯基-,其中M是-O-、-S-、-SO2-、-CH2-或-C(CH3)2-;
Y16是各有2-10个碳原子的亚烷基、氧杂亚烷基或硫杂亚烷基,亚苯基,或有2-6个碳原子的亚烯基;
Y17是有2-10个碳原子的亚烷基,亚苯基,或烷基部分有1-11个碳原子的烷基亚苯基;和
Y18是有2-10个碳原子的亚烷基,或是有4-20个碳原子并被一个或多个氧间断的亚烷基。
进一步的优选的聚烯烃组合物中,式(Ia)化合物的取代基Y1是氢、1-12个碳原子的烷基、1-18个碳原子的烷氧基、苯基或卤素;如果u是1,则Y2是1-18个碳原子的烷基、被羟基取代的1-12个碳原子的烷基、1-18个碳原子的烷氧基、-COOY8、-CONY9Y10和/或-OCOY11、缩水甘油基或烷基部分有1-4个碳原子的苯基烷基;或者,如果u是2,则Y2是2-16个碳原子的亚烷基,4-12个碳原子的亚烯基,亚二甲苯基,或是被一个或多个-O-原子间断并被羟基取代的3-20个碳原子的亚烷基;取代基Y8至Y11的定义同上。
优选u是1。
典型的个别化合物如下:
2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪,2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-十二烷氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-十三烷氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-〔2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基〕-4,6-二(2,4-二甲基)-1,3,5-三嗪,2-〔2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基〕-4,6-二(2,4-二甲基)-1,3,5-三嗪,2-〔4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基〕-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-〔2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基〕-4,6-二(4-甲基苯基)-1,3,5-三嗪,2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪,2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪,2,4,6-三〔2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基〕-1,3,5-三嗪,2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪,2-{2-羟基-4-〔3-(2-乙基己基-1-氧)-2-羟基丙氧基〕苯基}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪。
特别优选的是以下化合物。
G1=CH(CH3)-COO-C2H5
a)R1=R2=CH(CH3)-COO-C8H17,R3=R4=H;
b)R1=R2=R3=CH(CH3)-COO-C8H17,R4=H;
c)R1=R2=R3=R4=CH(CH3)-COO-C8H17
这些羟苯基三嗪UV吸收剂是已知化合物,一部分是商业产品。
羟苯基苯并三嗪UV吸收剂的合适实例是以下结构式IIa、IIb或IIc化合物:
在式(IIa)化合物中,
R101是氢,1-24个碳原子的烷基,烷基部分有1-4个碳原子的苯基烷基,5-8个碳原子的环烷基,或下式基团
其中R104和R105彼此独立地是各有1-5个碳原子的烷基,或者R104与基团CnH2n+1-m一起形成一个5-12个碳原子的环烷基,
m是1或2,n是从2到20的整数,
M是基团-COOR106,其中
R106是氢,1-12个碳原子的烷基,在烷基部分和烷氧基部分各有1-20个碳原子的烷氧基烷基,或是在烷基部分有1-4个碳原子的苯基烷基,
R102是氢,卤素,1-18个碳原子的烷基及烷基部分有1-4个碳原子的苯基烷基,
R103是氢,氯,各有1-4个碳原子的烷基或烷氧基,或-COOR106,其中R106的定义如上;
在式(IIb)化合物中,
T是氢或1-6个碳原子的烷基,
T1是氢,氯,或各有1-4个碳原子的烷基或烷氧基,
n是1或2,以及
如果n是1,则T2是氯或基团-OT3,或是
如果n是2,则T2是基团
或-O-T9-O-,其中
T3是氢,未被取代或被1-3个羟基取代或-OCOT6取代的1-18个碳原子的烷基,被1个或几个-O-或-NT6-间断的未被取代或被羟基或-OCOT6取代的3-18个碳原子的烷基,未被取代或被羟基和/或1-4个碳原子的烷基取代的5-12个碳原子的环烷基,未被取代或被羟基取代的2-18个碳原子的链烯基,烷基部分有1-4个碳原子的苯基烷基,或基团-CH2CH(OH)-T7或
T4和T5彼此独立地是氢,1-18个碳原子的烷基,被一个或多个-O-或-NT6-间断的3-18个碳原子的烷基,5-12个碳原子的环烷基,苯基,被1-4个碳原子的烷基取代的苯基,3-8个碳原子的链烯基,烷基部分有1-4个碳原子的苯基烷基,或2-4个碳原子的羟烷基,
T6是氢,1-18个碳原子的烷基,5-12个碳原子的环烷基,3-8个碳原子的链烯基,苯基,被1-4个碳原子取代的苯基,烷基部分有1-4个碳原子的苯基烷基,
T7是氢,1-18个碳原子的烷基,未取代的或被羟基取代的苯基,烷基部分有1-4个碳原子的苯基烷基,或-CH2OT8,
T8是1-18个碳原子的烷基,3-8个碳原子的链烯基,5-10个碳原子的环烷基,苯基,被1-4个碳原子的烷基取代的苯基,或烷基部分有1-4个碳原子的苯基烷基,
T9是2-8个碳原子的亚烷基,4-8个碳原子的亚烯基,4个碳原子的亚炔基,亚环己基,被一个或多个-O-间断的2-8个碳原子的亚烷基,或基团-CH2CH(OH)CH2OT11OCH2CH(OH)CH2-或-CH2-C(CH2OH)2-CH2-,
T10是可被一个或多个-O-间断的2-20个碳原子的亚烷基,或亚环己基,
T11是2-8个碳原子的亚烷基,被一个或多个-O-间断的2-18个碳原子的亚烷基,1,3-亚环己基,1,4-亚环己基,1,3-亚苯基或1,4-亚苯基,或
T10和T6与两个氮原子合起来是一个哌嗪基;
在式(IIc)化合物中,R′102是C1-C12烷基,k是数字1-4。
在式(IIa)化合物中,R101可以是氢或有1-24个碳原子的烷基,例如甲基、乙基、丙基、丁基、己基、辛基、壬基、十二烷基、十四烷基、十六烷基、十八烷基、十九烷基和二十烷基,及相应的支化异构体。
另外,除了烷基部分内有1-4个碳原子的苯基烷基(例如苄基)之外,R101也可以是5-8个碳原子的环烷基,例如环戊基、环己基和环辛基,或是基团
其中R104和R105彼此独立地是各有1-5个碳原子的烷基,特别是甲基,或者R104与该CnH2n+1-m基团一起形成一个有5-12个碳原子的环烷基基团,例如环己基、环辛基和环癸基。M是式-COOR106基团,其中R106不仅是氢,而且也是有1-12个碳原子的烷基,或在烷基和烷氧基部分各有1-20个碳原子的烷氧基烷基。合适的烷基R106是对于R101列举的那些。合适的烷氧基烷基的实例是-C2H4OC2H5、-C2H4OC8H17和-C4H8OC4H9。作为有1-4个碳原子的苯基烷基,R106是例如苄基、异丙苯基、α-甲基苄基或苯基丁基。
除了氢和卤素(例如氯和溴)之外,R102也可以是1-18个碳原子的烷基,这些烷基的实例示于R101的定义中。R102也可以是在烷基部分有1-4个碳原子的苯基烷基,例如苄基、α-甲基苄基和异丙苯基。
作为取代基的卤素在所有情形均指氟、氯、溴或碘,优选氯或溴,更优选是氯。
基团R101和R102中至少一个必须不是氢。
除了氢或氯之外,R103还是各有1-4个碳原子的烷基或烷氧基,例如甲基、丁基、甲氧基和乙氧基,以及-COOR106。
在式(IIb)化合物中,T是氢或1-6个碳原子的烷基,例如甲基和丁基;T1不仅是氢或氯,也可以是各有1-4个碳原子的烷基或烷氧基,例如甲基、甲氧基和丁氧基,而且若n是1,则T2是氯或基团-OT3或-NT4T5。这里的T3是氢或1-18个碳原子的烷基(参看R101的定义)。这些烷基可以被1-3个羟基或被基团-OCOT6取代。另外,T3可以是被一个或多个-O-或-NT6-间断的、未取代或被羟基或-OCOT6取代的3-18个碳原子的烷基(参见R101的定义)。作为环烷基的T3的实例是环戊基、环己基或环辛基。T3也可以是2-18个碳原子的链烯基。合适的链烯基由R101定义中列举的烷基衍生得到。这些链烯基可以被羟基取代。作为苯基烷基的T3的实例是苄基、苯乙基、异丙苯基、α-甲基苄基或苄基。T3也可以是基团-CH2CH(OH)-T7或
像T3一样,T4和T5彼此独立地可以不仅是氢,而且也可以是1-18个碳原子的烷基,或是被一个或多个-O-或-NT6-间断的3-18个碳原子的烷基。T4和T5也可以是5-12个碳原子的环烷基,例如环戊基、环己基和环辛基。作为链烯基的T4和T5的实例可以在T3的示例说明中找到。作为烷基部分有1-4个碳原子的苯基烷基的T4和T5的实例是苄基或苯丁基。最后,这些取代基也可以是有1-3个碳原子的羟烷基。
如果n是2,则T2是化学式为
或-O-T9-O-的二价基团。
除氢之外,T6(也见以上)还是烷基、环烷基、链烯基、芳基或苯基烷基;上面已给出了这些基团的实例。
除了氢和上述的苯基烷基及长链烷基之外,T7还可以是苯基或羟苯基以及-CH2OT8,其中T8可以是所列举的烷基、链烯基、环烷基、芳基或苯基烷基等基团之一。
二价基团T9可以是有2-8个碳原子的亚烷基,而且这些基团也可以是支化的。这也适用于亚烯基和亚炔基基团T9。与亚环己基一样,T9也可以是下式基团:
-CH2CH(OH)CH2OT11OCH2CH(OH)CH2-或-CH2-C(CH2OH)2-CH2-。
T10是一个二价基团,除了亚环己基外,还是可以被一个或多个-O-间断的2-20个碳原子的亚烷基。合适的亚烷基是由在R101的定义中叙述的烷基衍生得到。
T11也是亚烷基。它含有2-8个碳原子,或者在被一个或几个-O-间断时,含4-10个碳原子。T11也可以是1,3-亚环己基、1,4-亚环己基、1,3-亚苯基或1,4-亚苯基。
T6和T10还可以与两个氮原子一起形成一个哌嗪环。
优选的是式(IIa)化合物,其中R101是氢或有1-20个碳原子的烷基,R102是氢,1-18个碳原子的烷基或烷基部分有1-4个碳原子的苯基烷基;R103是氢、氯或有1-4个碳原子的烷基。
特别优选的式(IIa)化合物中,R101处于羟基的邻位,是氢或4-12个碳原子的烷基,R102处于该羟基的对位,是1-6个碳原子的烷基或异丙苯基,R103是氢或氯。
式(I)、(Ia)、(IIa)、(IIb)、(IIc)的UV吸收剂是本身已知的,在例如WO 96/28431、EP-A-323408、EP-A-57160、US5736597(EP-A-434608)和US-A 4619956中对其及其制备方法有说明。取代基和个别化合物的优选含义可以由所述文献推断。
特别优选的是以下化合物:
2-(2′-羟基-5′-甲基苯基)苯并***、2-(3′,5′-二叔丁基-2′-羟苯基)苯并***,2-(5′-叔丁基-2′-羟苯基)苯并***、2-(2′-羟基-5′-(1,1,3,3-四甲基丁基)苯基)苯并***,2-(3′,5′-二叔丁基-2′-羟苯基)-5-氯苯并***、2-(3′-叔丁基-2′-羟基-5′-甲基苯基)-5-氯苯并***,2-(3′-仲丁基-5′-叔丁基-2′-羟苯基)苯并***,2-(2′-羟基-4′-辛氧基苯基)苯并***,2-(3′,5′-二叔戊基-2′-羟苯基)苯并***,2-(3′,5′-二(α,α-二甲基苄基)-2′-羟苯基)苯并***,2-(3′-叔丁基-2′-羟基-5′-(2-辛氧羰基乙基)苯基)-5-氯苯基***,2-(3′-叔丁基-5′-〔2-(2-乙基己氧基)羰基乙基〕-2′-羟苯基)-5-氯苯并***,2-(3′-叔丁基-2′-羟基-5′-(2-甲氧羰基乙基)苯基)-5-氯苯并***,2-(3′-叔丁基-2′-羟基-5′-(2-甲氧羰基乙基)苯基)苯并***,2-(3′-叔丁基-2′-羟基-5′-(2-辛氧羰基乙基)苯基)苯并***,2-(3′-叔丁基-5′-〔2-(2-乙基己氧基)羰基乙基〕-2′-羟苯基)苯并***,2-(3′-十二烷基-2′-羟基-5′-甲基苯基)苯并***,2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧基羰基乙基)苯基)苯并***,2,2-亚甲基二〔4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基苯酚〕;2-〔3′-叔丁基-5′-(2-甲氧羰基乙基)-2′-羟苯基〕-2H-苯并***与聚乙二醇300的酯交换产物;[R-CH2CH2-COO-CH2CH2-]2,其中R=3′-叔丁基-4′-羟基-5′-2H-苯并***-2-基苯基,2-〔2′-羟基-3′-(α,α-二甲基苄基)-5′-(1,1,3,3-四甲基丁基)苯基〕苯并***;2-〔2′-羟基-3′-(1,1,3,3-四甲基丁基)-5′-(α,α-二甲基苄基)苯基〕苯并***。
UV吸收剂通常按各为聚合物重量的0.005-5%的数量掺入。UV吸收剂的总量优选为聚烯烃重量的0.01-5%、更优选为0.05-2%、最优选为0.05-1%。羟苯基三嗪UV吸收剂与羟苯基苯并三嗪UV吸收剂的重量比优选为10∶1至1∶10,更优选为5∶1至1∶5,最优选为2∶1至1∶2。
特别优选的混合物如下:
Tinuvin 326 Cyasorb UV 1164,
Tinuvin 327 Cyasorb UV 1164,
Tinuvin 328 Cyasorb UV 1164,
e)Tinuvin 327和Tinuvin 1577,
f)Tinuvin 328和Tinuvin 1577,
g)Tinuvin 326和
化合物101,
h)Tinuvin 327和化合物101,
i)Tinuvin 328和化合物101。
化合物101和类似取代的三嗪在例如WO 96/28431中公开。
可用于本发明的位阻胺光稳定剂优选是式(A-1)至(A-10)化合物或(B-1)至(B-10)化合物;
(α-1)式(A-1)化合物
其中
E1是氢,C1-C8烷基,O,-OH,-CH2CN,C1-C18烷氧基,C5-C12环烷氧基,C3-C6链烯基,未取代的或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;或是C1-C8酰基,
m1是1、2或4,
如果m1是1,则E2是C1-C25烷基,
如果m1是2,则E2是C1-C14亚烷基或式(a-1)基团
其中E3是C1-C10烷基或C2-C10链烯基,E4是C1-C10亚烷基,E5和E6彼此独立地是C1-C4烷基、环己基或甲基环己基,
如果m1是4,则E2是C4-C10链烯四基;
(α-2)式(A-2)化合物
其中
E7基团中的2个是-COO-(C1-C20烷基),2个是式(a-II)
基团
E8具有E1的含义之一;
(α-3)式(A-3)化合物
其中
E9和E10合起来形成C2-C14亚烷基,
E11是氢或基团-Z1-COO-Z2,
Z1是C2-C14亚烷基,
Z2是C1-C24烷基,且
E12具有E1的含义之一;
(α-4)式(A-4)化合物
其中
基团E13彼此独立地具有E1的含义之一,
基团E14彼此独立地是氢或C1-C12烷基,
E15是C1-C10亚烷基或C3-C10亚烷基;
(α-5)式(A-5)化合物
其中基团E16彼此独立地具有E1的含义之一;
(α-6)式(A-6)化合物
其中
E17是C1-C24烷基,
E18具有E1的含义之一;
(α-7)式(A-7)化合物
其中
E19、E20和E21彼此独立地是式(a-III)基团
其中E22具有E1的含义之一;
(α-8)式(A-8)化合物
其中
基团E23彼此独立地具有E1的含义之一,
E24是氢、C1-C12烷基或C1-C12烷氧基;
(α-9)式(A-9)化合物
其中
m2是1、2或3,
E25具有E1的含义之一,而且
当m2是1时,E26是基团
当m2是2时,E26是C2-C22亚烷基,
当m2是3时,E26是式(a-IV)基团
其中基团E27彼此独立地是C2-C12亚烷基,基团E28彼此独立地是C1-C12烷基或C5-C12环烷基;
(α-10)式(A-10)化合物
其中基团E29彼此独立地具有E1的含义之一,E30是C2-C22亚烷基、C5-C7亚环烷基、C1-C4亚烷基二(C5-C7亚环烷基)、亚苯基或亚苯基二(C1-C4亚烷基);
(β-1)式(B-1)化合物
其中
R201、R203、R204和R205彼此独立地是氢,C1-C12烷基,C5-C12环烷基,C1-C4烷基取代的C5-C12环烷基,苯基,被-OH和/或C1-C10烷基取代的苯基;C7-C9苯基烷基,在苯基上被-OH和/或C1-C10烷基取代的C7-C9苯基烷基;或是式(b-1)基团
R202是C2-C18亚烷基,C5-C7亚环烷基或C1-C4亚烷基二(C5-C7亚环烷基),或
基团R201、R202和R203与它们所键合的氮原子一起形成一个5至10元杂环,或
R204和R205与它们所键合的氮原子形成一个5-10元杂环,
R206是氢、C1-C8烷基、O、-OH、-CH2CN、C1-C18烷氧基、C5-C12环烷氧基、C3-C6链烯基、未取代的或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;或C1-C8酰基,b1是从2到50的数字,条件是,R201、R203、R204和R205中至少一个是式(b-1)基团;
(β-2)式(B-2)化合物
其中
R207和R211彼此独立地是氢或C1-C12烷基,
R208、R209和R210彼此独立地是C2-C10亚烷基,
X1、X2、X3、X4、X5、X6、X7和X8彼此独立地是式(b-II)基团,
其中R212是氢,C1-C12烷基,C5-C12环烷基,C1-C4烷基取代的C5-C12环烷基,苯基,-OH-和/或C1-C10烷基取代的苯基,C7-C9苯基烷基,苯基上被-OH和/或C1-C10烷基取代的C7-C9苯基烷基;或是如上定义的式(b-1)基团,
R213具有R206的含义之一;
(β-3)式(B-3)化合物
其中
R214是C1-C10烷基,C5-C12环烷基,C1-C4烷基取代的C5-C12环烷基,苯基或C1-C10烷基取代的苯基,
R215是C3-C10亚烷基,
R216具有R206的含义之一,且
b2是从2至50的数字,
(β-4)式(B-4)化合物
其中
R217和R221彼此独立地是一个直接键或-N(X9)-CO-X10-CO-N(X11)-基团,其中X9和X11彼此独立地是氢、C1-C8烷基、C5-C12环烷基、苯基、C7-C9苯基烷基或式(b-1)基团,
X10是一个直接键或C1-C4亚烷基,
R218具有R206的含义之一,
R219、R220、R223和R224彼此独立地是氢、C1-C30烷基、C5-C12环烷基或苯基,
R222是氢,C1-C30烷基,C5-C12环烷基,苯基,C7-C9苯基烷基,或式(b-1)基团,
b3是从1到50的数字;
(β-5)式(B-5)化合物
其中
R225、R226、R227、R228和R229彼此独立地是直接键或C1-C10亚烷基,
R230具有R206的含义之一,
b4是从1到50的数字;
(β-6)产物(B-6),可以通过由式(B-6-1)的聚胺与氰尿酰氯反应得到的产物与式(B-6-2)化合物反应得到
其中
b5′、b5″和b5彼此独立地是从2到12的数字,
R231是氢、C1-C12烷基、C5-C12环烷基、苯基或C7-C9苯基烷基,
R232具有R206的含义之一;
(β-7)式(B-7)的化合物
其中A1是氢或C1-C4烷基,
A2是直接键或C1-C10亚烷基,
n1是数字2至50;
(β-8)至少一种式(B-8-a)和(B-8-b)化合物
其中n2和n2 *是数字2至50;
(β-9)式(B-9)化合物
其中A3和A4彼此独立地是氢或C1-C8烷基,或者A3和A4合起来形成一个C2-C14亚烷基,变量n3彼此独立地是数字1-50;
(β-10)式(B-10)化合物
其中n4是数字2-50,A5是氢或C1-C4烷基,基团A6和A7彼此独立地是C1-C4烷基或式(b-1)基团,条件是,至少50%的基团A7是式(b-1)基团。
最多达30个碳原子的烷基实例是甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基、1,1,3,3,5,5-六甲基己基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十二烷基和三十烷基。E1、E8、E12、E13、E16、E18、E22、E23、E25、E29、E206、E213、E216、E218、E230和E232的优选定义之一是C1-C4烷基,尤其是甲基。R231优选是丁基。
具有最多达18个碳原子的烷氧基的实例是甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、戊氧基、异戊氧基、己氧基、庚氧基、辛氧基、癸氧基、十二烷氧基、十四烷氧基、十六烷氧基和十八烷氧基。E1的优选含义之一是辛氧基。E24优选是C1-C4烷氧基,而R206的优选含义之一是丙氧基。
C5-C12环烷基的实例是环戊基、环己基、环庚基、环辛基和环十二烷基。优选的是C5-C8环烷基,尤其是环己基。
C1-C4烷基取代的C5-C12环烷基是例如甲基环己基或二甲基环己基。
C5-C12环烷氧基的实例是环戊氧基、环己氧基、环庚氧基、环辛氧基、环癸氧基和环十二烷氧基。优选的是C5-C8环烷氧基,特别是环戊氧基。
-OH和/或C1-C10烷基取代的苯基是例如甲基苯基、二甲基苯基、三甲基苯基、叔丁基苯基或3,5-二叔丁基-4-羟基苯基。
C7-C9苯基烷基的实例是苄基和苯乙基。
苯基上被-OH和/或被有最多10个碳原子的烷基取代的C7-C9苯基烷基的实例是甲基苄基、二甲基苄基、三甲基苄基、叔丁基苄基或3,5-二叔丁基-4-羟基苄基。
有最多10个碳原子的链烯基的实例是烯丙基、2-甲基烯丙基、丁烯基、戊烯基和己烯基。优选烯丙基。1位上的碳原子优选是饱和的。
含不多于8个碳原子的酰基的实例是甲酰基、乙酰基、丙酰基、丁酰基、戊酰基、己酰基、庚酰基、辛酰基、丙烯酰基、甲基丙烯酰基和苯甲酰基。优选的是C1-C8烷酰基、C3-C8链烯酰基和苯甲酰基。特别优选的是乙酰基和丙烯酰基。
有最多22个碳原子的亚烷基的实例是亚甲基、亚乙基、亚丙基、1,3-亚丙基、1,4-亚丁基、1,5-亚戊基、2,2-二甲基-1,3-亚丙基、1,6-亚己基、三甲基1,6-亚己基、1,8-亚辛基和1,10-亚癸基。
C3-C10亚烷基的一个实例是基团
C4-C10链烷四基的实例是1,2,3,4-丁烷四基。
C5-C7亚环烷基的实例是亚环己基。
C1-C4亚烷基二(C5-C7亚环烷基)的实例是亚甲基二亚环己基。
亚苯基二(C1-C4亚烷基)的实例是亚甲基-亚苯基-亚甲基或亚乙基-亚苯基-亚乙基。
在R201、R202和R203与它们所连接的氮原子一起形成一个5-10元杂环的情形,该环是例如
优选的是6元杂环。
在R204和R205与它们所连接的氮原子一起形成一个5至10元杂环的情形,该环是例如1-吡咯烷基,哌啶基,吗啉基,1-哌嗪基,4-甲基-1-哌嗪基,1-六氢氮杂基、5,5,7-三甲基-1-高哌嗪基或4,5,5,7-四甲基-1-高哌嗪基。特别优选的是吗啉基。
R219和R223的优选定义之一是苯基。
R226优选是一个直接键。
n1、n2、n2 *和n4优选是数字2至25,特别是2至20。
n3优选是数字1至25,特别是1至20。
b1和b2优选是数字2至25,特别是2至20。
b3和b4优选是数字1至25,特别是1至20。
b5′和b5优选是3,b5″优选是2。
上述化合物是已知的,并可在市场上购得。它们全可用已知方法制备。
这些化合物的制备方法公开于例如以下文献:
US-A-5,679,733,US-A-3,640,928,US-A-4,198,334,US-A-5,204,473,US-A-4,619,958,US-A-4,110,306,US-A-4,110,334,US-A-4,689,416,US-A-4,408,051,SU-A-768,175(Derwent 88-138,751/20),US-A-5,049,604,US-A-4,769,457,US-A-4,356,307,US-A-4,619,956,US-A-5,182,390,GB-A-2,269,819,US-A-4,292,240,US-A-5,026,849,US-A-5,071,981,US-A-4,547,538,US-A-4,976,889,US-A-4,086,204,US-A-6,046,304,US-A-4,331,586,US-A-4,108,829,US-A-5,051,458,WO-A-94/12,544(Derwent94-177,274/22),DD-A-262,439(Derwent 89-122,983/17),US-A-4,857,595,US-A-4,529,760,US-A-4,477,615,CAS 136,504-96-6,US-A-4,233,412,US-A-4,340,534,WO-A-98/51,690和EP-A-1,803.
产物(B-6)可以与已知方法相似地制备,例如式(B-6-1)的聚胺与氰尿酰氯按1∶2至1∶4的摩尔比在无水碳酸锂、碳酸钠或碳酸钾存在下于有机溶剂(例如1,2-二氯乙烷、甲苯、二甲苯、苯、二烷或叔戊醇)中反应2-8小时,反应温度为-20℃至+10℃,优选由-10℃至+10℃,特别是由0℃至+10℃,随后使形成的产物与式(B-6-2)的2,2,6,6-四甲基-4-哌啶胺反应。2,2,6,6-四甲基-4-哌啶胺与式(B-6-1)的聚胺的摩尔比是例如4∶1至8∶1。所述量的2,2,6,6-四甲基-4-哌啶胺可以一次加入,或以几小时的间隔分批加入。
式(B-6-1)的聚胺与氰尿酰氯及式(B-6-2)的2,2,6,6-四甲基-4-哌啶胺的摩尔比优选为1∶3∶5至1∶3∶6。
以下实施例简述了优选产物(B-6-α)一种的制备方法。
实施例
23.6g(0.128mol)氰尿酰氯、7.43g(0.0426mol)N,N′-二[3-氨基丙基]乙二胺和18g(0.13mol)无水碳酸钾在5℃于搅拌下在250ml 1,2-二氯乙烷中反应3小时。将该混合物在室温下再温热4小时。加入27.2g(0.128mol)N-(2,2,6,6-四甲基-4-哌啶基)丁胺,将形成的混合物在60℃温热2小时。再加入18g(0.13mol)无水碳酸钾,将混合物在60℃再温热6小时。在低真空(200毫巴)下蒸馏除去溶剂,用二甲苯代替。加入18.2g(0.085mol)N-(2,2,6,6-四甲基-4-哌啶基)丁胺和5.2g(0.13mol)磨细的氢氧化钠,将混合物加热回流2小时,再用12小时以共沸蒸馏方式除去反应期间形成的水。将混合物过滤。溶液用水洗,用Na2SO4干燥。蒸除溶剂,残余物在真空中(0.1毫巴)于120-130℃下干燥。得到所要的产物,为无色树脂状物。
一般,产物(B-6)可以例如用式(B-6-α)、(B-6-β)或(B-6-γ)表示。它也可以是这三种化合物的混合物。
式(B-6-α)的一种优选的含义是
式(B-6-β)的一种优选的含义是
式(B-6-γ)的一种优选的含义是
在以上式(B-6-α)至(B-6-γ)中,b5优选是2至20,特别是2至10。
组分(c)的位阻胺优选选自以下商业产品:
DASTIB 845(RTM),TINUVIN 770(RTM),TINUVIN 765(RTM),TINUVIN 144(RTM),TINUVIN 123(RTM),TINUVIN 111(RTM),TINUVIN 783(RTM),TINUVIN791(RTM),MARK LA52(RTM),MARK LA 57(RTM),MARK LA 62(RTM),MARKLA 67(RTM),HOSTAVIN N 20(RTM),HOSTAVIN N 24(RTM),SANDUVOR3050(RTM),DIACETAM 5(RTM),SUMISORB TM 61(RTM),UVINUL 4049(RTM),SANDUVOR PR 31(RTM),GOODRITE UV 3034(RTM),GOODRITE UV3150(RTM),GOODRITE UV 3159(RTM),GOODRITE 3110×128(RTM),UVINUL 4050H(RTM),CHIMASSORB 944(RTM),CHIMASSORB 2020(RTM),CYASORB UV 3346(RTM),CYASORB UV 3529(RTM),DASTIB 1082(RTM),CHIMASSORB 119(RTM),UVASIL 299(RTM),UVASIL 125(RTM),UVASIL2000(RTM),UVINUL 5050H(RTM),LICHTSCHUTZSTOFF UV 31(RTM),LUCHEM HA B 18(RTM),MARK LA 63(RTM),MARK LA 68(RTM),UVASORBHA 88(RTM),TINUVIN 622(RTM),HOSTAVIN N 30(RTM)和FERRO AM 806(RTM).
特别优选的是TINUVIN 770(RTM),TINUVIN 791(RTM),TINUVIN 622(RTM),TINUVIN 783(RTM),CHIMASSORB 944(RTM),CHIMASSORB 2020(RTM)和CHIMASSORB 119(RTM)。
最优选的是Tinuvin 770(RTM)和Tinuvin 791(RTM)。
在式(B-1)、(B-3)、(B-4)、(B-5)、(B-6-α)、(B-6-β)、(B-6-γ)、(B-7)、(B-8-a)、(B-8-b)和(B-10)化合物中饱和自由价的端基,与制备各化合物所用的方法有关。这些端基也可以在制备了化合物后改性。
如果式(B-1)化合物是通过下式化合物
其中X是例如卤素,特别是氯,R204和R205的定义如上,与下式化合物反应制备
其中R201、R202和R203的定义同上,则结合在二氨基上的端基是氢,或是
而结合在三嗪基上的端基是X,或是
如果X是卤素,则最好是在反应完成时用-OH或氨基替换它。可以提到的氨基包括吡咯烷-1-基、吗啉基、-NH2、-N(C1-C8烷基)2和-NR(C1-C8烷基),其中R是氢或式(b-1)基团。
式(B-1)化合物还包括下式化合物
其中R201、R202、R203、R204、R205和b1的定义如上,R204 *具有R204的含义之一,R205 *具有R205的含义之一。
一种特别优选的式(B-1)化合物是
此化合物的制备在US-A-6,046,304的实施例10中有说明。
在式(B-3)化合物中,与硅原子结合的端基可以是例如(R14)3-Si-O-,与氧原子结合的端基可以是例如-Si(R14)3。
如果b2是数字3至10,则式(B-3)化合物也可以是环状化合物的形式,即,结构式中画出的自由价此时形成一个直接键。
在式(B-4)化合物中,与2,5-二氧代吡咯烷环结合的端基是例如氢,而与-C(R223)(R224)-基团结合的端基是例如
在式(B-5)化合物中,与羰基结合的端基是例如
与氧基结合的端基是例如
在式(B-6-α)、(B-6-β)和(B-6-γ)化合物中,与三嗪基结合的端基是例如Cl或下式基团
与氨基结合的端基是例如氢或下式基团
如果式(B-7)化合物是用下式化合物
其中A是氢或甲基,与式Y-OOC-A2-COO-Y的二羧酸二酯反应制得,其中Y是例如甲基、乙基或丙基,A2的定义同上,则结合在2,2,6,6-四甲基-4-氧哌啶-1-基上的端基是氢或是-CO-A2-COO-Y,结合在二酰基上的端基是-O-Y或下式基团
在式(B-8-a)化合物中,与氮结合的端基可以是氢,与2-羟基亚丙基结合的端基可以是下式基团
在式(B-8-b)化合物中,与二亚甲基结合的端基可以是-OH,与氧结合的端基可以是氢。这些端基也可以是聚醚基团。
在式(B-10)化合物中,与-CH2-结合的端基可以是氢,与--CH(CO2A7)基结合的端基可以是-CH=CH-COOA7。
其它的个别化合物是以下化合物:
二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物,N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的直链或环形缩合物,三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1′-(1,2-乙二基)-双(3,3,5,5-四甲基哌嗪酮),4-苯甲酰-2,2,6,6-四甲基哌啶,4-十八烷氧基-2,2,6,6-四甲基哌啶,二(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯,3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4,5]癸烷-2,4-二酮,二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯,N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的直链或环状缩合物,2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合物,2-氯-4,6-二(4-正丁氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4,5]-癸烷-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮,3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮,4-十六烷氧基-和4-十八烷氧基-2,2,6,6-四甲基哌啶的混合物,N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物,1,2-二(3-氨基丙氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合物,以及4-丁氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6]);1,6-己二胺和2,4,6-三氯-1,3,5-三嗪的缩合物及N,N-二丁胺和4-丁氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[192268-64-7]);N-(2,2,6,6-四甲基-4-哌啶基)正十二烷基琥珀酰亚胺,N-(1,2,2,6,6-五甲基-4-哌啶基)正十二烷基琥珀酰亚胺,2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷,7,7,9,9-四甲基-2环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷和表氯醇的反应产物,1,1-二(1,2,2,6,6-五甲基-4-哌啶氧基羰基)-2-(4-甲氧基苯基)乙烯,N,N′-二甲酰-N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺,4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯,聚[甲基丙基-3-氧-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷,马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
在本发明的一项具体实施方案中,颜料是选自二酮基吡咯并吡咯类颜料,UV吸收剂是Tinuvin 327(RTM)和Tinuvin 1577(RTM)的混合物,位阻胺稳定剂是Tinuvin 791(RTM)或Tinuvin 770(RTM),基体是聚丙烯。
位阻胺化合物(组分3)在要稳定的聚烯烃中的数量优选是聚烯烃重量的0.005-5%,特别是0.01-1%或0.05-1%。
被稳定的材料中还可另外含有各种常规添加剂,例如:
1.抗氧化剂
1.1 烷基化一元酚,例如,2,6-二叔丁基-4-甲基苯酚,2-叔丁基-4,6-二甲基苯酚,2,6-二叔丁基-4-乙基苯酚,2,6-二叔丁基-4-正丁基苯酚,2,6-二叔丁基-4-异丁基苯酚,2,6-二环戊基-4-甲基苯酚,2-(α-甲基环己基)-4,6-二甲基苯酚,2,6-双十八烷基-4-甲基苯酚,2,4,6-三环己基苯酚,2,6-二叔丁基-4-甲氧基甲基苯酚,侧链为直链或支链的壬基酚,例如2,6-二壬基-4-甲基苯酚,2,4-二甲基-6-(1′-甲基十一烷-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十七烷-1′-基)苯酚,2,4-二甲基-6-(1′-甲基十三烷-1′-基)苯酚,及它们的混合物。
1.2 烷硫基甲基苯酚,例如,2,4-二辛硫基甲基-6-叔丁基苯酚,2,4-二辛硫基甲基-6-甲基苯酚,2,4-二辛硫基甲基-6-乙基苯酚,2,6-二(十二烷硫基甲基)-4-壬基酚。
1.3 氢醌和烷基化氢醌,例如,2,6-二叔丁基-4-甲氧基苯酚,2,5-二叔丁基氢醌,2,5-二叔戊基氢醌,2,6-二苯基-4-十八烷氧基苯酚,2,6-二叔丁基氢醌,2,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯基硬脂酸酯,二(3,5-二叔丁基-4-羟基苯基)己二酸酯。
1.4 生育酚,例如,α-生育酚,β-生育酚,γ-生育酚,δ-生育酚及其混合物(维生素E)。
1.5 羟基化的硫代二苯醚,例如,2,2′-硫代二(6-叔丁基-4-甲基苯酚),2,2′-硫代二(4-辛基苯酚),4,4′-硫代二(6-叔丁基-3-甲基苯酚),4,4′-硫代二(6-叔丁基-2-甲基苯酚),4,4′-硫代二(3,6-二仲戊基苯酚),4,4′-二(2,6-二甲基-4-羟基苯基)二硫醚。
1.6 亚烷基双酚,例如,2,2′-亚甲基双(6-叔丁基-4-甲基苯酚),2,2′-亚甲基双(6-叔丁基-4-乙基苯酚),2,2′-亚甲基双[4-甲基-6-(α-甲基环己基)苯酚],2,2′-亚甲基双(4-甲基-6-环己基苯酚),2,2′-亚甲基双(6-壬基-4-甲基苯酚),2,2′-亚甲基双(4,6-二叔丁基苯酚),2,2′-亚乙基双(4,6-二叔丁基苯酚),2,2′-亚乙基双(6-叔丁基-4-异丁基苯酚),2,2′-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚],2,2′-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4′-亚甲基双(2,6-二叔丁基苯酚),4,4′-亚甲基双(6-叔丁基-2-甲基苯酚),1,1-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷,2,6-双(3-叔丁基-5-甲基-2-羟苄基)-4-甲基苯酚,1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷,1,1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷,乙二醇二[3,3-二(3′-叔丁基-4′-羟苯基)丁酸酯],二(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯,二[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯,1,1-二(3,5-二甲基-2-羟苯基)丁烷、2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷,2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷,1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7 O-、N-和S-苄基化合物,例如,3,5,3′,5′-四叔丁基-4,4′-二羟基二苄基酯,十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯,十三烷基-4-羟基-3,5-二叔丁基苄基巯基乙酸酯,三(3,5-二叔丁基-4-羟基苄基)胺,二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯,二(3,5-二叔丁基-4-羟基苄基)硫醚,异辛基-3,5-二叔丁基-4-羟基苄基巯基乙酸酯。
1.8 羟苄基化的丙二酸酯,例如,双十八烷基-2,2-二(3,5-二叔丁基-2-羟基苄基)丙二酸酯,双十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯,双十二烷基巯基乙基-2,2′-二(3,5-二叔丁基-4-羟苄基)丙二酸酯,二[4-(1,1,3,3-四甲基丁基)苯基]-2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸酯。
1.9 芳族羟苄基化合物,例如,1,3,5-三(3,5-二叔丁基-4-羟苄基)-2,4,6-三甲基苯,1,4-二(3,5-二叔丁基-4-羟苄基)-2,3,5,6-四甲基苯,2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯酚。
1.10 三嗪化合物,例如,2,4-二(辛基巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-二(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪,2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪,1,3,5-三(3,5-二叔丁基-4-羟苄基)异氰尿酸酯,1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰尿酸酯,2,4,6-三(3,5-二叔丁基-4-羟基苯乙基)-1,3,5-三嗪,1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰)六氢-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟苄基)异氰尿酸酯。
1.11 苄基膦酸酯,例如,二甲基-2,5-二叔丁基-4-羟苄基膦酸酯,二乙基-3,5-二叔丁基-4-羟苄基膦酸酯,双十八烷基-3,5-二叔丁基-4-羟基苄基膦酸酯,双十八烷基-5-叔丁基-4-羟基-3-甲基苄基膦酸酯,3,5-二叔丁基-4-羟苄基膦酸的单乙酯的钙盐。
1.12 酰氨基苯酚。例如,4-羟基月桂酰苯胺,4-羟基硬脂酰苯胺,N-(3,5-二叔丁基-4-羟苯基)氨基甲酸辛酯。
1.13 β-(3,5-二叔丁基-4-羟苯基)丙酸与一元或多元醇的酯,例如,与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-二(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯。
1.14 β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元或多元醇的酯,例如,与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-二(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷,3,9-二[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙烯氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5.5]-十一烷的酯。
1.15 β-(3,5-二环己基-4-羟苯基)丙酸与一元或多元醇的酯,例如,与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-二(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯
1.16 3,5-二叔丁基-4-羟苯基乙酸与一元或多元醇的酯,例如,与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-二(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷的酯
1.17 β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺,例如,N,N′-二(3,5-二叔丁基-4-羟苯基丙酰)六亚甲基二酰胺,N,N′-二(3,5-二叔丁基-4-羟苯基丙酰)三亚甲基二酰胺,N,N′-二(3,5-二叔丁基-4-羟苯基丙酰)肼,N,N′-二[2-(3-[3,5-二叔丁基-4-羟苯基丙酰氧基)乙基]草酰胺(Naugard XL-1,Uniroyal产品)。
1.18 抗坏血酸(维生素C)
1.19 胺型抗氧化剂,例如,N,N′-二异丙基对苯二胺,N,N′-二仲丁基对苯二胺,N,N′-二(1,4-二甲基戊基)对苯二胺,N,N′-二(1-乙基-3-甲基戊基)对苯二胺,N,N′-二(1-甲基庚基)对苯二胺,N,N′-二环己基对苯二胺,N,N′-二苯基对苯二胺,N,N′-二(2-萘基)对苯二胺,N-异丁基-N′-苯基对苯二胺,N-(1,3-二甲基丁基)-N′-苯基对苯二胺,N-(1-甲基庚基)-N′-苯基对苯二胺,N-环己基-N′-苯基对苯二胺,4-(对甲苯氨磺酰)二苯基胺,N,N′-二甲基-N,N′-二仲丁基对苯二胺,二苯胺,N-烯丙基二苯胺,4-异丙氧基二苯胺,N-苯基-1-萘胺,N-(4-叔辛基苯基)-1-萘胺,N-苯基-2-萘胺,辛基化的二苯胺,例如P,P′-二叔辛基二苯胺,4-正丁基氨基苯酚,4-丁酰氨基苯酚,4-壬酰氨基苯酚,4-十二烷酰氨基苯酚,4-十八烷酰氨基苯酚,双(4-甲氧基苯基)胺,2,6-二叔丁基-4-二甲基氨基甲基苯酚,2,4′-二氨基二苯基甲烷,4,4′-二氨基二苯基甲烷,N,N,N′,N′-四甲基-4,4′-二氨基二苯基甲烷,1,2-二[(2-甲基苯基)氨基]乙烷,1,2-二(苯氨基)丙烷,(邻甲苯基)双胍,二[4-(1′,3′-二甲基丁基)苯基]胺,叔辛基化N-苯基-1-萘胺,一和二烷基化的叔丁基/叔辛基二苯胺的混合物;一和二烷基化的壬基二苯胺的混合物,一和二烷基化的十二烷基二苯胺的混合物,一和二烷基化的异丙基/异己基二苯胺的混合物,一和二烷基化的叔丁基二苯胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,一和二烷基化的叔丁基/叔辛基吩噻嗪的混合物,一和二烷基化的叔辛基吩噻嗪的混合物,N-烯丙基吩噻嗪,N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯,N,N-二(2,2,6,6-四甲基哌啶-4-基六亚甲基二胺,二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯,2,2,6,6-四甲基哌啶-4-酮,2,2,6,6-四甲基哌啶-4-醇。
2.UV吸收剂和光稳定剂
2.2 2-羟基二苯酮,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2′,4′-三羟基和2′-羟基-4,4′-二甲氧基衍生物。
2.3 取代和未取代的苯甲酸酯,例如,水杨酸4-叔丁基苯基酯,水杨酸苯酯,水杨酸辛基苯酯,二苯甲酰间苯二酚,二(4-叔丁基苯甲酰)间苯二酚,苯甲酰间苯二酚,3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯,3,5-二叔丁基-4-羟基苯甲酸十六烷基酯,3,5-二叔丁基-4-羟基苯甲酸十八烷基酯,3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯酯。
2.4 丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙酯,α-氰基-β,β-二苯基丙烯酸异辛酯,α-甲氧羰基肉桂酸甲酯,α-氰基-β-甲基对甲氧基肉桂酸甲酯,α-氰基-β-甲基对甲氧基肉桂酸丁酯,α-甲氧羰基对甲氧基肉桂酸甲酯和N-(β-甲氧羰基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5 镍化合物,例如,2,2′-硫代二[4-(1,1,3,3-四甲基丁基)苯酚]的镍络合物,例如有或没有其它配体如正丁胺、三乙醇胺或N-环己基二乙醇胺的1∶1或1∶2络合物;二丁基二硫代氨基甲酸镍;4-羟基-3,5-二叔丁基苄基膦酸的一烷基酯(例如甲酯或乙酯)的镍盐,酮肟(例如2-羟基-4-甲基苯基十一烷基酮肟)的镍络合物,1-苯基-4-月桂酰-5-羟基吡唑的有或没有其它配体的镍络合物。
2.7 草酰胺,例如,4,4′-二辛氧基-N,N′-草酰二苯胺,2,2′-二乙氧基-N,N′-草酰二苯胺,2,2′-二辛氧基-5,5′-二叔丁氧基-N,N′-草酰二苯胺,2,2′-双十二烷氧基-5,5′-二叔丁基-N,N′-草酰二苯胺,2-乙氧基-2′-乙基-N,N′-草酰二苯胺,N,N′-二(3-二甲基氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙氧基-N,N′-草酰二苯胺及其与2-乙氧基-2′-乙基-5,4′-二叔丁基草酰二苯胺的混合物,邻与对甲氧基双取代的N,N′-草酰二苯胺的混合物和邻与对乙氧基双取代的草酰二苯胺的混合物。
3.金属减活剂,例如,N,N′-二苯基草酰胺,N-水杨醛-N′-水杨酰肼,N,N′-二(水杨酰)肼,N,N′-二(3,5-二叔丁基-4-羟基苯基丙酰)肼,3-水杨酰氨基-1,2,4-***,二(亚苄基)草酰二肼,N,N′-草酰二苯胺,间苯二甲酰二肼,癸二酰二苯基酰肼,N,N-二乙酰己二酰二肼,N,N′-二(水杨酰)草酰二肼,N,N′-二(水杨酰)硫代丙酰二肼。
4.亚磷酸酯和亚膦酸酯,例如,亚磷酸三苯酯,亚磷酸二苯基烷基酯,亚磷酸苯基二烷基酯,亚磷酸三(壬基苯基)酯,亚磷酸三月桂酯,亚磷酸三(十八烷基)酯,二亚磷酸二硬脂基季戊四醇酯,亚磷酸三(2,4-二叔丁基苯基)酯,二亚磷酸二异癸基季戊四醇酯,二亚磷酸二(2,4-二叔丁基苯基)季戊四醇酯,二亚磷酸二(2,4-二异丙苯基苯基)季戊四醇酯,二亚磷酸二(2,6-二叔丁基-4-甲基苯基)季戊四醇酯,二亚磷酸二异癸氧基季戊四醇酯,二亚磷酸二(2,4-二叔丁基-6-甲基苯基)季戊四醇酯,二亚磷酸二(2,4,6-三叔丁基苯基)季戊四醇酯,三亚磷酸三硬脂基山梨醇酯,二亚膦酸四(2,4-二叔丁基苯基)-4,4′-亚联苯基酯,6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯,亚磷酸二(2,4-二叔丁基-6-甲基苯基)甲基酯,亚磷酸二(2,4-二叔丁基-6-甲基苯基)乙基酯,6-氟-2,4,8,10-四叔丁基-12-甲基二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯,2,2′,2″-次氮基[三乙基三(3,3′,5,5′-四叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯],2-乙基己基(3,3′,5,5′-四叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯,5-丁基-5-乙基-2-(2,4,6-三叔丁基苯氧基)-1,3,2-二氧杂磷杂环丙烷。
以下是特别优选的亚磷酸酯:
亚磷酸三(2,4-二叔丁基苯基)酯(Irgafos168,Ciba-Geigy),亚磷酸三(壬基苯基)酯,
5.羟胺,例如,N,N-二苄基羟胺,N,N-二乙基羟胺,N,N-二辛基羟胺,N,N-二月桂基羟胺,N,N-双十四烷基羟胺,N,N-双十六烷基羟胺,N,N-双十八烷基羟胺,N-十六烷基-N-十八烷基羟胺,N-十七烷基-N-十八烷基羟胺,由氢化牛油胺衍生形成的N,N-二烷基羟胺。
6.硝酮,例如N-苄基-α-苯基硝酮,N-乙基-α-甲基硝酮,N-辛基-α-庚基硝酮,N-月桂基-α-十一烷基硝酮,N-十四烷基-α-十三烷基硝酮,N-十六烷基-α-十五烷基硝酮,N-十八烷基-α-十七烷基硝酮,N-十六烷基-α-十七烷基硝酮,N-十八烷基-α-十五烷基硝酮,N-十七烷基-α-十七烷基硝酮,N-十八烷基-α-十六烷基硝酮,由氢化牛油胺衍生的N,N-二烷基羟基胺衍生形成的硝酮。
7.硫代增效剂,例如硫代二丙酸二月桂酯或硫代二丙酸二硬脂酯。
8.过氧化物清除剂,例如β-硫代二丙酸的酯,如十二烷基酯、十八烷基酯、十四烷基酯或十三烷基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫代氨基甲酸锌,二(十八烷基)二硫醚,季戊四醇四(β-十二烷基巯基)丙酸酯。
9.碱性共稳定剂,例如,三聚氰胺,聚乙烯吡咯烷酮,双氰胺、氰尿酸三烯丙酯,脲衍生物,肼衍生物,胺,聚酰胺,聚氨基甲酸酯,高级脂肪酸的碱金属和碱土金属盐,例如硬脂酸钙、硬脂酸锌、山萮酸镁、硬脂酸镁、蓖麻酸钠和棕榈酸钾,焦儿茶酸锑或焦化茶酸锌。
10.成核剂,例如无机物质,如,滑石、金属氧化物(如二氧化钛或氧化镁),磷酸盐、碳酸盐或硫酸盐(优选碱土金属盐);有机化合物,如,一元或多元羧酸及其盐,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;聚合物,例如离子型共聚物(离聚物)。特别优选的是1,3:2,4-二(3′,4′-二甲基亚苄基)山梨醇,1,3:2,4-二(对甲基二亚苄基)山梨醇,和1,3:2,4-二(亚苄基)山梨醇。
11.填料和增强剂,例如,碳酸钙、硅酸盐、玻璃纤维、玻璃球、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木粉以及其它天然产物的粉或纤维、合成纤维。
12.其它添加剂,例如,增塑剂、润滑剂、乳化剂、颜料、流变添加剂、催化剂、流动控制剂、荧光增白剂、阻燃剂、防静电剂和发泡剂。
13.苯并呋喃酮和吲哚啉酮,例如,在U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839或EP-A-0591102中公开的那些,或3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二叔丁基苯并呋喃-2-酮,5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮,3,3′-二[5,7-二叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮],5,7二叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮,3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮,3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二叔丁基苯并呋喃-2-酮,3-(3,4-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮,3-(2,3-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮。
上述的另外的稳定剂和添加剂通常以0.01-2%的用量使用。
因此,本发明的对象还包括如上所述的聚烯烃组合物,其中还含有选自酚类抗氧化剂、亚磷酸酯或亚膦酸酯以及苯并呋喃酮或二氢吲哚酮的另一种稳定剂。
上述的组分a、b、c和另外的添加剂可以用已知方法掺入到要稳定的聚烯烃中,例如在成形之前或成形期间掺入,或向聚烯烃中施加溶解或分散的化合物,若有必要,随后蒸除溶剂。这些组分可以以粉末、颗粒或含浓度为例如2.5-25%重量的这些组分的母料的形式加到聚烯烃中。
如果需要,可以在掺入聚烯烃之前将各组分彼此熔融掺混。它们也可以在聚合之前或之中加到聚烯烃中。
按照本发明稳定的材料可以以各式各样的形式使用,例如薄膜、纤维、条带、模塑组合物或型材。
本发明聚烯烃的加工或转化的实例是:
注射吹塑,挤压成形,吹塑,粉料滚塑,模具装饰(返注成型),搪塑,注塑,共注塑,成形,压塑,压制,薄膜挤塑(流延薄膜,吹胀薄膜),纺丝(织造的,非织造的),撑压(单轴,双轴),退火,深度撑压,压延,机械转化,烧结,共挤压,涂布,层压,交联(辐射、过氧化物、硅烷),蒸汽沉积,熔接,胶粘,热成形,管材挤塑,型材挤塑,片材挤塑,挤压涂布,减粘裂化(过氧化法,热),纤维熔喷,纺丝粘合,表面处理(电晕放电,火焰处理,等离子体),消毒(用γ射线,电子束),浇铸聚合(R&M方法,RAM挤压法),凝胶涂布和带材挤塑。
本发明的聚烯烃可以用来制备:
1-1)浮动装置,海洋应用,浮舟,浮标,用于甲板、码头、船、小艇、桨和海滩加固物的塑料成材。
1-2)汽车应用,特别是保险杠、前围板、电池、后衬和前衬、发动机罩下的模塑部件、帽架、行李箱衬里、内衬、气囊罩、零配件用的电子模塑件、代表盘的部件、前灯玻璃、仪器表盘、外衬里、车身内饰件、汽车灯、前灯、停车灯、尾灯、制动灯、内和外装饰物、车门镶板、汽油箱、装玻璃的前侧、后玻璃窗、座椅靠背、外镶板、电线绝缘物、用于密封的挤压型材、包层、车身柱罩、底盘部件、排气***、滤油器/加油器、燃料泵、汽油箱、车身侧边压制件、折叠式车蓬、车外后视镜、外饰件、紧固件/零配件、前端模制件、玻璃、绞链、车锁***、行李/车顶行李架、压制/冲压部件、密封件、侧面碰撞保护装置、***/绝缘物和车身太阳天窗。
1-3)道路交通装置,特别是标志杆、路标牌、汽车附件、预警三角标志、医药箱、头盔、轮胎。
1-4)飞机、铁路、汽车(小汽车、摩托车)的装置,包括陈设品。
1-5)空间应用,特别是火箭和卫星,例如再进入大气的屏蔽层。
1-6)建筑和设计用的装置,采矿用途,消声***,街道安全带,车站站棚。
11-1)在普通和电动/电子装置(个人计算机、电话、手机、打印机、电视机、视听装置)中的器具、盒和罩,花盆,卫星电镜碟形天线,以及面板装置。
11-2)用于其它材料,例如钢或纺织品的保护层。
11-3)电子工业装置,特别是插头绝缘,尤其是计算机插头,电动和电子部件的箱体、印刷板,以及作为电子数据贮存材料,例如集成电路片、查验卡或***。
11-4)电器、特别是洗衣机,滚动式干燥机、烤箱(微波炉),洗碗机,混合机和熨斗。
11-5)灯罩(例如路灯、灯罩)。
11-6)电线和电缆应用(半导体,绝缘体和电缆包层)。
11-7)用于冷凝器、冰箱、加热装置、空调的箔片,电子、半导体的包封,咖啡机和吸尘器。
111-1)机械制品,例如嵌齿轮(齿轮)、滑动配件、垫片、螺丝、螺栓、把手和旋钮。
111-2)转子叶片,通风机和风车的叶片,太阳能装置,游泳池,游泳池罩,池衬,水池衬里,壁橱,大衣橱,分隔墙,板条隔墙,折叠隔墙,屋顶,百叶窗(例如卷升百叶窗),零配件,管道连接件,套筒和传送带。
111-3)厕所用品,特别是淋浴间,马桶座,盖和水槽。
111-4)卫生用品,特别是尿布(婴儿用,成人尿失禁),女性卫生用品,淋浴帘,刷子,垫子,浴盆,移动式厕所,牙刷和便盆。
111-5)水、废水和化学品用的管道(交联或不交联的),用于电线和电缆保护的管道,气体、油和污水用管道,漕沟,水落管和排水***。
111-6)任何几何形状的型材(窗玻璃)和壁板。
111-7)玻璃替代品,特别是挤压法平板、建筑物(单、双或多层玻璃)、飞机、学校用的玻璃材料、挤压片材,建筑玻璃、火车、运输、清洁用品和温室用的窗用薄膜。
111-8)平板(壁板,剪裁板)、挤压涂布(相纸、包装牛奶或饮料的四面体纸板盒和管道涂料,筒仓木材代用品,塑料成材,木材复合材料,壁板,面材,家具,装饰性箔材,地板盖层(内部和外部使用),楼面地板材料,跳板和瓦片。
111-9)集合管的入口和出口。
111-10)水泥、混凝土、复合材料应用,以及盖料、挡板和包层,栏杆,扶手,厨房操作台面,屋面材料,屋面板,瓦片和防水帆布。
IV-1)平板(壁板和剪裁板),托盘,人造草地,阿斯特罗草皮,圆形比赛场的人工盖顶(运动),圆形体育场的人造地面(运动),以及条带。
IV-2)织造织物连续纤维和切断纤维(地毯/卫生制品/土工织物/单丝;过滤材料;楷布/窗帘(遮光物)/医药应用),散纤维(用于例如长袍/保护服),网,绳,缆绳,细绳,绳索,线,座位安全带,衣服,内衣,手套,靴子,橡皮船,贴身衣服,服装,泳衣,运动服,伞(女用阳伞,遮阳伞),降落伞,滑翔伞,帆,“气球绸”露营制品,帐蓬,充气床,日光浴床,大袋子,袋子。
IV-3)膜,绝缘膜,用于屋面、隧道、垃圾堆、水池的覆盖物和密封物,墙壁顶蓬膜,土工膜,游泳池,帘子(遮盖)/防晒,雨蓬,华盖,壁纸,食品包装和包裹(柔性的和固体的),药品包装(柔性的和固体的),气囊/安全带,扶手和头枕,地毯,中间仪表台,仪表盘,驾驶座,门,顶置式仪表台组件,门饰,车顶内衬,内置灯,内置镜,包裹架,后部行李盖板,座位,操纵杆,方向盘,纺织品和车身装饰物。
V)薄膜(包装,垃圾堆,层压,农业和园艺,温室,地面覆盖材料,隧道,青贮饲料),大包包裹,游泳池,废物袋,壁纸,弹性薄膜,酒椰叶纤维薄膜,脱盐薄膜,电池和接插件。
VI-1)食品包装和包裹(柔性和固体),BOPP,BOPET 1瓶。
VI-2)储存体系,例如储存箱(板条箱)、行李、箱柜、家用箱、制模板、橱架,导轨,螺丝箱,包装容器和罐。
VI-3)弹药箱,注射器,医药应用,运输容器,废物篮和废物箱,废物袋,垃圾箱,垃圾箱衬里,轮式箱,通用容器,水槽/用过的水/化学品/气体/油/汽油/柴油;槽衬,箱,板条箱,电池盒,槽/医用装置,如注射器芯,眼科应用,诊断设备,以及泡形药物的包装。
VII-1)挤压涂布(相纸,包装饮料的四面体纸板盒,管道涂料),任何种类的家用制品(例如,器具,热水瓶/衣架),固定体系,例如插头、电线和电缆夹、拉链,闭合装置,锁和锁扣。
VII-2)支承装置,休闲用品,例如运动和键身设备,体操垫,滑雪靴,inline-skates,滑雪板,big foot,运动地面(例如网球场地);瓶子的螺纹盖、盖和塞子,以及罐。
VII-3)通用家具,发泡制品(垫子,减震器),泡沫塑料,海绵,碗布,垫子,庭院椅子,运动场座椅,桌子,睡椅,玩具,建筑配套件(板/图/球),游戏室,滑梯和游戏车辆。
VII-4)光学和磁学数据储存材料。
VII-5)厨房用具(吃、喝、烹调、储存)。
VII-6)CD盒、盒式带和录象带盒;DVD电子制品,任何种类的办分室用品(园珠笔,***和印台,鼠标,书架,导轨),任何体积和内容物的瓶子(饮料,洗涤剂,化妆品包括香水),和胶带。
VII-7)鞋类(鞋/鞋底),鞋垫,鞋罩,粘结剂,结构粘合剂,食物箱(水果,蔬菜,肉,鱼),合成纸,瓶用标干,长沙发,人造关节(人类),印刷板(苯胺印刷术),印刷电路板,和显示器技术。
VII-8)填充聚合物(滑石、白垩、陶土(高岭土)、硅灰石、颜料、炭黑、TiO2、云母、纳米复合材料、白云石、硅酸盐、玻璃、石棉)的装置。
本发明的另外方面是用于稳定含至少一种有机颜料的聚烯烃免遭光、热或氧化引起的降解的方法,该方法包括向着色聚烯烃中加入一种稳定剂混合物,其中含有
a)至少一种位阻胺光稳定剂和
b)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物,
以及以下物质的混合物对于稳定含至少一种有机颜料的聚烯烃的应用
a)至少一种位阻胺光稳定剂和
b)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物。
定义和择优性已经给出。它们也适用于稳定方法和稳定剂混合物的应用。
以下实施例示例说明了本发明。
实施例1:PP均聚物薄膜的光稳定化
将100份未经稳定化的聚丙烯粉末(熔体流动指数3.8g/10分,230℃/2160g)在Brabender塑性计中与0.05份季戊四醇四-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯,0.05份三(2,4-二叔丁基苯基)亚磷酸酯一起在200℃均化10分,辅助添加剂、颜料和稳定剂的数量如表中所示。将这样得到的材料在实验室压机上于两个铝箔之间在260℃压塑6分钟,形成0.5mm厚的薄膜,将其立即在水冷式压机中冷却至室温。从该0.5mm薄膜中切下60×25mm的样品,置于Weather-Ometer Ci65中曝光(黑面板温度63±2℃,不喷水雾)。从曝光装置中定期取出这些样品,用红外分光光度计测定其羰基含量。与羰基吸光度达到0.1相应的曝光时间作为光稳定剂的稳定效率的量度。所得数值列在表1中。
表1.含有机和无机颜料的PP薄膜的光稳定性
所有制剂中均含:0.1%Tinuvin770+0.1%硬脂酸镁+0.25%TiO2(金红石)
0.05%TINUVIN 327+0.05%TINUVIN 1577 | 2125 | 2018 |
0.25%CHROMOPHTALDPP RED BOC | ||
对照样(无UV吸收剂)0.10%TINUVIN 3270.10%TINUVIN 15770.05%TINUVIN 327+0.05%TINUVIN 1577 | 7140689581559040 | 7525 |
实施例2:PP均聚物薄膜的光稳定化
100份未稳定的聚丙烯粉末(熔体流动指数3.4g/10分,230℃/2160g)在Brabender塑性计中与0.05份季戊四醇四-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯、0.05份三(2,4-二叔丁基苯基)亚磷酸酯一起在200℃均化10分钟,辅助添加剂、颜料和光稳定剂的用量示于表中。将这样得到的材料在实验室压机中于两个铝箔之间在260℃压塑6分钟,形成0.5mm厚的薄膜,将其在水冷压机中立即冷却到室温。从这些0.5mm薄膜中切割出60×25mm的样品,在Weather-OmeterCi65中曝光(黑面板温度63±2℃,不喷水雾)。
定期地从曝光设备中取出样品,用红外分光光度计测定其羰基含量。
与羰基吸光度达到0.1相对应的曝光时间是光敏剂稳定效率的量度。所得数值列在表2和3中。
表2:含有机颜料的PP薄膜的光稳定性
所有制剂均含:0.1%Tinuvin 770+0.1%硬脂酸钙
0.05%TINUVIN 327+0.05%TINUVIN1577 | 9285 | 8100 |
0.25%Cinquasia Red B RT 195-D | ||
0.1%TINUVIN 327 | 4065 | |
0.1%TINUVIN 1577 | 6421 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 5898 | 5243 |
0.25%IRGALITE Green GFNP | ||
0.1%TINUVIN 327 | 4009 | |
0.1%TINUVIN 1577 | 6393 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 5561 | 5201 |
0.25%Chromophtal Orange GL | ||
0.1%TINUVIN 327 | 2851 | |
0.1%TINUVIN 1577 | 3388 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 3462 | 3120 |
0.25%IRGAZIN Red BPTN | ||
0.1%TINUVIN 327 | 4883 | |
0.1%TINUVIN 1577 | 4953 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 5034 | 4918 |
表3.含有机和无机颜料的PP薄膜的光稳定性
所有制剂中均含:0.1%Tinuvin 770+0.1%硬脂酸镁+0.25% TiO2
0.05%TINUVIN 327+0.05%TINUVIN1577 | 11582 | 11144 |
0.25%Cinquasia Red Y RT 759-D | ||
0.1%TINUVIN 327 | 8417 | |
0.1%TINUVIN 1577 | 10155 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 9451 | 9286 |
0.25%Irgalite Blue BSP | ||
0.1%TINUVIN 327 | 5028 | |
0.1%TINUVIN 1577 | 7129 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 6402 | 6078 |
0.25%Chromophtal Blue A3R | ||
0.1%TINUVIN 327 | 7376 | |
0.1%TINUVIN 1577 | 9456 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 9120 | 8416 |
0.25%IRGALITE Green GFNP | ||
0.1%TINUVIN 327 | 3827 | |
0.1%TINUVIN 1577 | 6360 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 5911 | 5094 |
0.25%IRGAZIN Red BPTN | ||
0.1%TINUVIN 327 | 5279 | |
0.1%TINUVIN 1577 | 6525 | |
0.05%TINUVIN 327+0.05%TINUVIN1577 | 6180 | 5902 |
实施例3:PP均聚物薄膜的光稳定化
100份未稳定的聚丙烯粉末(熔体流动指数3.6g/10分,230℃/2160g)与0.05份季戊四醇四-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯,0.05份三(2,4-二叔丁基苯基)亚磷酸酯、0.1份硬脂酸钙一起在Brabender塑性计中于200℃均化10分钟,颜料和光稳定剂的数量如表中所示。将这样得到的材料在实验室压机中于两个铝箔之间在260℃下压塑6分钟,形成0.5mm厚的薄膜,立即在水冷式压机中冷却至室温。从这些0.5mm薄膜中切割60×25mm的样品,在Weather-OmeterCi65中曝光(黑面板温度63±2℃,不喷水雾)。
定期地从曝光装置中取出这些样品,用红外分光光度计测定其羰基含量。
与羰基吸光度达到0.1相对应的曝光时间是光稳定剂稳定效率的量度。所得数值总结在表4和5中。
表4:含有机颜料的PP薄膜的光稳定性
所有制剂均含:0.25%Chromophthal DPP Red BOC+0.1%CHIMASSORB 944
表5.含有机颜料的PP薄膜的光稳定性
所有制剂均含:0.25%Chromophthal DPP Red BOC+0.1%TINUVIN 770
颜料和化学品种类
商品名称 | 化学说明 | C.I.命名 |
CHROMOPHTHAL Yellow 3G | 双偶氮缩合颜料 | 颜料黄93 |
CHROMOPHTHAL Red BRN | 双偶氮缩合颜料 | 颜料红144 |
CHROMOPHTHAL DPP Red BOC | 二酮基吡咯并吡咯颜料 | 颜料红254 |
CHROMOPHTHAL Red 2030 | 二酮基吡咯并吡咯颜料 | 颜料红254 |
CHROMOPHTAL Yellow 2RLP | 异吲哚啉酮 | 颜料黄110 |
CHROMOPHTAL Yellow GT-AD | 蒽醌 | 颜料黄199 |
CHROMOPHTAL DPP Orange TRP | 二酮基吡咯并吡咯 | 颜料橙71 |
IRGAZIN DPP Rubine TR | 二酮基吡咯并吡咯 | 颜料红272 |
CINQUASIA Red Y RT-759-D | 喹吖啶酮 | 颜料紫19 |
CINQUASIA Red B RT 195-D | 喹吖啶酮 | - |
IRGALITE Blue BSP | 稳定的α-型酞菁铜 | 颜料蓝15:1 |
CHROMOPHTAL Blue A3R | 蒽醌 | 颜料蓝60 |
IRGALITE Green GFNP | 酞菁铜 | 颜料绿7 |
CHROMOPHTAL Orange GL | 苯并咪唑酮 | 颜料橙64 |
IRGAZIN Red BPTN | 苝 | 颜料红224 |
CHROMOPHTAL Orange 2G | 异吲哚酮 | 颜料橙61 |
所使用的所有UV吸收剂、光稳定剂以及所有的颜料都有注册商标并且是Ciba Specialty Chemicals Corp.的商业产品。
Claims (11)
1.一种聚烯烃组合物,其中含有
a)至少一种有机颜料,其选自偶氮颜料、蒽醌、苯并咪唑酮、二嗪、酞菁、四氯异吲哚啉酮、喹吖啶酮、异吲哚啉、苝和吡咯并吡咯类颜料;
b)至少一种位阻胺光稳定剂和
c)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物,其中2-羟苯基-s-三嗪UV吸收剂与2-羟苯基苯并***UV吸收剂之重量比为10∶1至1∶10。
2.权利要求1的聚烯烃组合物,其中聚烯烃是聚丙烯、聚乙烯或其共聚物。
3.权利要求1的聚烯烃组合物,其中的2-羟苯基-s-三嗪类UV吸收剂是式(I)化合物
其中n是1或2;
R1、R′1、R2和R′2彼此独立地是H,OH,C1-C12烷基,C2-C6链烯基,C1-C12烷氧基,C2-C18烯氧基,卤素,三氟甲基,C7-C11苯基烷基,苯基,被C1-C18烷基、C1-C18烷氧基或卤素取代的苯基,苯氧基,或被C1-C18烷基、C1-C18烷氧基或卤素取代的苯氧基;
R3和R4彼此独立地是H,C1-C12烷基,OR′7,C2-C6链烯基,C2-C18烯氧基,卤素,三氟甲基,C7-C11苯基烷基,苯基,被C1-C18烷基、C1-C18烷氧基或卤素取代的苯基,苯氧基,或被C1-C18烷基、C1-C18烷氧基或卤素取代的苯氧基;
R6是氢,C1-C24烷基,C5-C12环烷基或C7-C15苯基烷基;
R7在n=1的情形和R′7彼此独立地是氢或C1-C18烷基;或者是被下述基团取代的C1-C12烷基:OH,C1-C18烷氧基,烯丙氧基,卤素,-COOH,-COOR8,-CONH2,-CONHR9,-CON(R9)(R10),-NH2,-NHR9,-N(R9)(R10),-NHCOR11,-CN,-OCOR11,苯氧基和/或被C1-C18烷基、C1-C18烷氧基或卤素取代的苯氧基;或者R7是被-O-间断并可被OH取代的C3-C50烷基;或者R7是C3-C6链烯基;缩水甘油基;C5-C12环烷基;被OH、C1-C4烷基或-OCOR11取代的环己基;未被取代的或被OH、Cl或CH3取代的C7-C11苯基烷基;-CO-R12或-SO2-R13;
R7在n=2的情形是C2-C16亚烷基、C4-C12亚烯基、亚二甲苯基,被O间断和/或被OH取代的C3-C20亚烷基,或者是基团CH2CH(OH)CH2O-R20-OCH2CH(OH)CH2-、-CO-R21-CO-、-CO-NH-R22-NH-CO或-(CH2)m-COO-R23-OOC-(CH2)m-,其中m是从1到3的数字,或者是
R8是C1-C18烷基;C2-C18链烯基;羟乙基;C3-C50烷基,该烷基被O、NH、NR9或S间断和/或被OH取代;被-P(O)(OR14)2、-N(R9)(R10)或-OCOR11和/或OH取代的C1-C4烷基;缩水甘油基;C5-C12环烷基;苯基;C7-C14烷基苯基或C7-C11苯基烷基;
R9和R10彼此独立地是C1-C12烷基,C3-C12烷氧基烷基,C4-C16二烷基氨基烷基或C5-C12环烷基,或者R9和R10合起来是C3-C9亚烷基或氧杂亚烷基或氮杂亚烷基;
R11是C1-C18烷基、C2-C18链烯基或苯基,C2-C12羟烷基,环己基,或是被-O-间断并可被OH取代的C3-C50烷基;
R12是C1-C18烷基,C2-C18链烯基,苯基,C1-C18烷氧基,C3-C18烯氧基,被O、NH、NR9或S间断和/或被OH取代的C3-C50烷氧基,环己氧基,C7-C14烷基苯氧基,C7-C11苯基烷氧基,苯氧基,C1-C12烷基氨基,苯基氨基,甲苯氨基或萘氨基;
R13是C1-C12烷基,苯基,萘基或C7-C14烷基苯基;
R14是C1-C12烷基,甲基苯基或苯基;
R20是C2-C10亚烷基,被O间断的C4-C50亚烷基,亚苯基或-亚苯基-X-亚苯基-,其中X是-O-、-S-、-SO2-、-CH2-或-C(CH3)2;
R21是C2-C10亚烷基,C2-C10氧杂亚烷基,C2-C10硫杂亚烷基,C6-C12亚芳基或C2-C6亚烯基;
R22是C2-C10亚烷基,亚苯基,亚甲苯基,二亚苯基甲烷,或以下基团
R23是C2-C10亚烷基或被O间断的C4-C20亚烷基。
4.权利要求1的聚烯烃组合物,其中2-羟苯基苯并***类UV吸收剂是式IIa、IIb和IIc化合物
在式(IIa)化合物中,
R101是氢,1-24个碳原子的烷基,烷基部分有1-4个碳原子的苯基烷基,5-8个碳原子的环烷基,或下式基团
其中R104和R105彼此独立地是各有1-5个碳原子的烷基,或者R104与基团CnH2n+1-m一起形成一个5-12个碳原子的环烷基,
m是1或2,n是从2到20的整数,
M是基团-COOR106,其中
R106是氢,1-12个碳原子的烷基,在烷基部分和烷氧基部分各有1-20个碳原子的烷氧基烷基,或是在烷基部分有1-4个碳原子的苯基烷基,
R102是氢,卤素,1-18个碳原子的烷基及烷基部分有1-4个碳原子的苯基烷基,
R103是氢,氯,各有1-4个碳原子的烷基或烷氧基,或-COOR106,其中R106的定义如上,基团R101和R102中至少一个不是氢;
在式(IIb)化合物中,
T是氢或1-6个碳原子的烷基,
T1是氢,氯,或各有1-4个碳原子的烷基或烷氧基,
n是1或2,以及
如果n是1,则T2是氯或基团-OT3,或是
如果n是2,则T2是基团
或-O-T9-O-,其中
T3是氢,未被取代或被1-3个羟基取代或-OCOT6取代的1-18个碳原子的烷基,被1个或几个-O-或-NT6-间断的未被取代或被羟基或-OCOT6取代的3-18个碳原子的烷基,未被取代或被羟基和/或1-4个碳原子的烷基取代的5-12个碳原子的环烷基,未被取代或被羟基取代的2-18个碳原子的链烯基,烷基部分有1-4个碳原子的苯基烷基,或基团-CH2CH(OH)-T7或
T4和T5彼此独立地是氢,1-18个碳原子的烷基,被一个或多个-O-或-NT6-间断的3-18个碳原子的烷基,5-12个碳原子的环烷基,苯基,被1-4个碳原子的烷基取代的苯基,3-8个碳原子的链烯基,烷基部分有1-4个碳原子的苯基烷基,或2-4个碳原子的羟烷基,
T6是氢,1-18个碳原子的烷基,5-12个碳原子的环烷基,3-8个碳原子的链烯基,苯基,被1-4个碳原子取代的苯基,烷基部分有1-4个碳原子的苯基烷基,
T7是氢,1-18个碳原子的烷基,未取代的或被羟基取代的苯基,烷基部分有1-4个碳原子的苯基烷基,或-CH2OT8,
T8是1-18个碳原子的烷基,3-8个碳原子的链烯基,5-10个碳原子的环烷基,苯基,被1-4个碳原子的烷基取代的苯基,或烷基部分有1-4个碳原子的苯基烷基,
T9是2-8个碳原子的亚烷基,4-8个碳原子的亚烯基,4个碳原子的亚炔基,亚环己基,被一个或多个-O-间断的2-8个碳原子的亚烷基,或基团-CH2CH(OH)CH2OT11OCH2CH(OH)CH2-或-CH2-C(CH2OH)2-CH2-,
T10是可被一个或多个-O-间断的2-20个碳原子的亚烷基,或亚环己基,
T11是2-8个碳原子的亚烷基,被一个或多个-O-间断的2-18个碳原子的亚烷基,1,3-亚环己基,1,4-亚环己基,1,3-亚苯基或1,4-亚苯基,或
T10和T6与两个氯原子合起来是一个哌嗪基;
在式(IIc)化合物中,R′102是C1-C12烷基,k是数字1-4。
5.权利要求1的聚烯烃组合物,其中UV吸收剂的总量为聚烯烃重量的0.01-5%。
6.权利要求1的聚烯烃组合物,其中位阻胺光稳定剂是选自以下化合物:二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物,N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的直链或环形缩合物,三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1′-(1,2-乙二基)-双(3,3,5,5-四甲基哌嗪酮),4-苯甲酰-2,2,6,6-四甲基哌啶,4-十八烷氧基-2,2,6,6-四甲基哌啶,二(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯,3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4,5]癸烷-2,4-二酮,二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯,N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的直链或环状缩合物,2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合物,2-氯-4,6-二(4-正丁氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4,5]-癸烷-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮,3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮,4-十六烷氧基-和4-十八烷氧基-2,2,6,6-四甲基哌啶的混合物,N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物,1,2-二(3-氨基丙氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合物,以及4-丁氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6]);1,6-己二胺和2,4,6-三氯-1,3,5-三嗪的缩合物及N,N-二丁胺和4-丁氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[192268-64-7]);N-(2,2,6,6-四甲基-4-哌啶基)正十二烷基琥珀酰亚胺,N-(1,2,2,6,6-五甲基-4-哌啶基)正十二烷基琥珀酰亚胺,2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷,7,7,9,9-四甲基-2环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷和表氯醇的反应产物,1,1-二(1,2,2,6,6-五甲基-4-哌啶氧基羰基)-2-(4-甲氧基苯基)乙烯,N,N′-二甲酰-N,N′-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺,4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯,聚[甲基丙基-3-氧-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷,马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
7.权利要求1的聚烯烃组合物,其中位阻胺化合物组分(b)占聚合物重量的0.005-5%。
8.权利要求1的聚烯烃组合物,其中还含有另外一种稳定剂,选自酚类抗氧化剂、亚磷酸酯或亚膦酸酯,以及苯并呋喃酮或二氢吲哚酮。
9.权利要求1的聚烯烃组合物,其中还另含一种无机颜料。
10.一种用于稳定含至少一种有机颜料的聚烯烃免于被光、热或氧化引起降解的方法,其中所述的有机颜料选自偶氮颜料、蒽醌、苯并咪唑酮、二嗪、酞菁、四氯异吲哚啉酮、喹吖啶酮、异吲哚啉、苝和吡咯并吡咯类颜料,该方法包括向着色的聚烯烃中掺入一种稳定剂混合物,该混合物含有:
a)至少一种位阻胺光稳定剂和
b)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物,其中2-羟苯基-s-三嗪UV吸收剂与2-羟苯基苯并***UV吸收剂之重量比为10∶1至1∶10。
11.以下物质的混合物在稳定含至少一种有机颜料的聚烯烃中的应用:
a)至少一种位阻胺光稳定剂和
b)作为UV吸收剂的2-羟苯基苯并***和2-羟苯基-s-三嗪的混合物,其中2-羟苯基-s-三嗪UV吸收剂与2-羟苯基苯并***UV吸收剂之重量比为10∶1至1∶10,
其中所述的有机颜料选自偶氮颜料、蒽醌、苯并咪唑酮、二嗪、酞菁、四氯异吲哚啉酮、喹吖啶酮、异吲哚啉、苝和吡咯并吡咯类颜料。
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CO5310577A1 (es) | 2003-08-29 |
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IL154706A0 (en) | 2003-10-31 |
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BR0300500A (pt) | 2004-08-10 |
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