CN101273084B - 颜色牢固的聚氨酯 - Google Patents
颜色牢固的聚氨酯 Download PDFInfo
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- CN101273084B CN101273084B CN2006800351618A CN200680035161A CN101273084B CN 101273084 B CN101273084 B CN 101273084B CN 2006800351618 A CN2006800351618 A CN 2006800351618A CN 200680035161 A CN200680035161 A CN 200680035161A CN 101273084 B CN101273084 B CN 101273084B
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- Prior art keywords
- carbon atoms
- alkyl
- phenyl
- compound
- carbon atom
- Prior art date
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- 229920002635 polyurethane Polymers 0.000 title claims description 12
- 239000004814 polyurethane Substances 0.000 title claims description 12
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 74
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 17
- -1 2-(2-hydroxy phenyl)-2H-benzotriazole compound Chemical class 0.000 claims description 131
- 125000004432 carbon atom Chemical group C* 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 239000001301 oxygen Substances 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 239000002131 composite material Substances 0.000 claims description 35
- 239000006096 absorbing agent Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000012545 processing Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 229910052724 xenon Inorganic materials 0.000 claims description 9
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 238000005266 casting Methods 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000001723 curing Methods 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000748 compression moulding Methods 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 238000004945 emulsification Methods 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 208000034189 Sclerosis Diseases 0.000 claims description 3
- 238000007664 blowing Methods 0.000 claims description 3
- 238000003490 calendering Methods 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 2
- 238000004043 dyeing Methods 0.000 claims 1
- 238000004898 kneading Methods 0.000 claims 1
- 229940124543 ultraviolet light absorber Drugs 0.000 abstract 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 abstract 2
- 239000002585 base Substances 0.000 description 58
- 229910052757 nitrogen Inorganic materials 0.000 description 51
- 150000001721 carbon Chemical group 0.000 description 21
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 description 20
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 229940035422 diphenylamine Drugs 0.000 description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 229940059574 pentaerithrityl Drugs 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 6
- DKHJONPHCWFBAX-UHFFFAOYSA-N 3-butyl-3h-1-benzofuran-2-one Chemical group C1=CC=C2C(CCCC)C(=O)OC2=C1 DKHJONPHCWFBAX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- SVTBMSDMJJWYQN-RXMQYKEDSA-N (4r)-2-methylpentane-2,4-diol Chemical compound C[C@@H](O)CC(C)(C)O SVTBMSDMJJWYQN-RXMQYKEDSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- QYSPWTBYSZPOCJ-UHFFFAOYSA-N 1-hydroxypentadecane-3-sulfonic acid Chemical compound CCCCCCCCCCCCC(CCO)S(O)(=O)=O QYSPWTBYSZPOCJ-UHFFFAOYSA-N 0.000 description 4
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
- XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 4
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 4
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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- 229940057402 undecyl alcohol Drugs 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
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- 239000000600 sorbitol Substances 0.000 description 2
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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
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- 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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- Polymers & Plastics (AREA)
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- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
提供了颜色牢固的热塑性组合物,其包括紫外光吸收剂和含至少一个硝酰基部分的化合物的组合物,和用于保持热塑性聚氨酯组合物的色牢度的方法,通过将所述紫外光吸收剂和含硝酰基的化合物引入热塑性聚氨酯组合物中。
Description
提供了颜色牢固的热塑性组合物,其包括有效量的紫外光吸收剂和含至少一个硝酰基部分的化合物的组合,和用于保持热塑性聚氨酯组合物的色牢度的方法,通过将所述紫外光吸收剂和含硝酰基的化合物引入热塑性聚氨酯组合物中。
热塑性聚氨酯(也称作TPU)的商业应用正快节奏地持续增长。不同于热固性聚氨酯,热塑性聚氨酯可以在操作中采取类似于其它热塑性聚合物的方式来处理,如挤出、注塑、线缆涂覆等。除了其所希望的加工性之外,TPU由于其极佳的性能组合而可应用于广泛的最终用途应用。
例如,TPU由于其硬度、拉伸强度、模量、柔韧性、和/或拉伸伸长率而是所期望的。这些物理性能与对多种加工和模塑参数的及时适应性的组合,使得TPU在多种最终用途应用中是有价值的,特别是在许多生活消费品中。
本文中所使用的热塑性聚氨酯是商业上众所周知的材料,且其描述可以在,例如,US 5,908,894、5,785,916、5,780,573、5,254,641、5,173,543(前述专利的每一个都全部内容引入本文作为参考)、其中的参考文献和无数的技术与商业出版物中找到。
由于其在生活消费品中的用途,除了优异的加工和性能特征之外,商业上所期望的TPU配方必须是视觉上吸引人的,且在该部件的寿命之内保持所期望的视觉特征。
典型的加工温度可以达到380°F~420°F(高达240°F),且经常获得淡黄色或无光泽外观的最终含TPU的产品。
将理解的是,黄色的或无光泽的外观是有害的,且在许多消费者和汽车应用中,是不可接受的。
非热塑性聚氨酯,例如,泡沫、涂料、浇铸或注塑制品等,通常不进行TPU所经受的严酷加工条件。通常,非热塑性聚氨酯在加工步骤中形成,例如,在浇铸或注塑中,其中在模具中制备该氨基甲酸乙酯聚合物,直接产生具有所选形状的制品。但是,存在弹性体和甚至交联聚氨酯进行进一步加工的情形。模塑氨基甲酸乙酯制品也经常在最初成型之后被加热,或是在模具中或是不采用。
一旦获得了热稳定的TPU组合物之后,必须在最终产品的寿命之内保持该含TPU产品的视觉上吸引人的外观。暴露于光、特别是紫外光时,该产品必须不显示发黄、发暗、灰化、发白、或变红。芳族TPU中更强调光致褪色。
出于许多美学和功能原因,上色(例如着色的或染色的)的TPU具有很大的经济价值。对于上色的聚合物,发黄、发暗、发白、或变红的影响表现为原色中可察觉的偏移。
色牢度是基质在暴露于风化条件时保持恒定颜色的性能。在暴露于热、光和其它环境压力时基质的颜色改变极小时称该基质具有“良好色牢度”或“高度的色牢度”。差的色牢度以几种可测量的方式来表现,包括褪色,更深颜色的形成,包括发黄,色调变化等。
由此所期望的是,提供具有优异加工性和性能特征、热稳定性、抗UV降解性且其在其使用寿命内保持恒定颜色的TPU组合物。这种TPU组合物应特别期望地用于消费者和汽车应用。
由此,现有技术已长期寻找这种TPU组合物。
如同许多聚合物体系一样,众所周知的是,采用光稳定剂,例如受阻胺光稳定剂(HALS)和紫外光吸收剂(UVA)来保持热塑性聚氨酯和其它氨基甲酸乙酯聚合物。最常见地,HALS组分为2,2,6,6-四甲基哌啶的衍生物,在受阻氮上在1位被氢、烷基和烷氧基取代。N-酰基取代也是已知的。
在受阻氮上带有羟基(羟基胺)或氧原子取代(硝酰基或nitroxy基团)的2,2,6,6-四甲基哌啶衍生物也是已知的,且经常显示更常见的N-H、N-烷基或N-烷氧基HALS中经常看不到的性能。2,2,6,6-四甲基哌淀衍生物的硝酰基衍生物在WO 2003085039中用作阻燃组合物的一部分;JP 11 158368(摘要)公开了采用硝基氧来有助于硅烷/氨基甲酸乙酯密封剂的室温储存;JP2001011328(摘要)公开了金属/聚膦酸/硝酰基组合用于具有良好储存稳定性的自由基可固化涂料。
US 5,785,916,其全部内容引入本文作为参考,公开了改进热塑性聚氨酯的UV和热稳定性的方法,通过在聚氨酯组合物中引入一种或多种丙烯酸酯基橡胶和一种或多种UV和/或热稳定剂。优选地,该稳定剂为特定的苯并三唑UV吸收剂,但也可以采用受阻胺光稳定剂。
US 6,767,940公开了使用包括硝酰基化合物如2,2,6,6-四甲基哌啶氧基的衍生物的稳定自由基来延长弹性体中的焦化时间,其中包括聚氨酯,优选地包括含至少40phr聚丁二烯的弹性体。
US 6,194,509公开了使用稳定自由基如2,2,6,6-四甲基哌啶氧基的衍生物来俘获可流化弹性体组合物中产生的自由基。
JP 59102950(摘要)公开了具有良好发白稳定性的聚氨酯组合物,包括作为链终止剂或封端剂的一部分引入氨基甲酸乙酯聚合物的硝酰基。
US专利申请2003年4月24日提交的第10/512,528号和2004年10月21日提交的10/970,112,其全部内容引入本文作为参考,教导了采用受阻硝酰基、空间受阻羟基胺和羟基铵盐,和采用二烷基羟基胺或取代的二烷基羟基胺或它们的盐来稳定身体护理产品、家居产品、纺织品和织物。
JP 2002234996公开了改进氨基甲酸乙酯树脂的耐候性,通过引入含有衍生自1-氧代-2,2,6,6-四甲基哌啶的硝酰基单元的氨基甲酸乙酯或酯。
已发现,将一些2,2,6,6-四甲基哌啶含硝酰基的化合物与紫外光吸收剂一起加到热塑性聚氨酯组合物中,给所获的TPU组合物提供了暴露于光时色牢度方面的显著改进。本发明的TPU组合物比包含紫外光吸收剂和,代替含硝酰基的化合物的,类似的N-H、N-烷基、N-烷氧基、N-酰基受阻胺光稳定剂或受阻羟基胺的热塑性聚氨酯组合物,颜色更牢固。
本发明提供了一种热塑性聚氨酯组合物,包括有效量的紫外光吸收剂与含至少一种式I硝酰基部分的化合物的混合物
其中,X和Y为H或者一起形成到氧上的双键,典型地X和Y为H,且其中,该热塑性聚氨酯组合物在依据SAE J 1960实验规程在2,500kJ的氙气暴露之后显示的由ΔE测量的颜色变化为小于5。
也提供了一种热塑性聚氨酯组合物,包括有效量的紫外光吸收剂与含至少一种式I硝酰基部分的化合物的混合物,其中该热塑性聚氨酯组合物在依据SAEJ1885实验规程在1,250kJ的氙气暴露之后显示的由ΔE测量的颜色变化为小于3。
UVA包括、但并非限定于,羟基苯基苯并三唑、二苯甲酮、苯并噁唑、α-氰基丙烯酸酯、草酰替苯胺、三酰基-s-三嗪、甲脒、肉桂酸酯、丙二酸酯、苄叉、水杨酸酯和苯甲酸酯UVA,和对苯二甲酸与间苯二甲酸的间苯二酚与苯酚酯。下面本文中给出具体实例。
关于添加剂的术语“有效量”是在色牢度方面达到所期望的效果的量。不同聚氨酯组合物褪色或经历褪色的速率大大不同。由此,紫外光吸收剂(本文中也称作UVA)和含至少一种式I硝酰基部分的化合物(本文中也称作“硝酰基化合物”或“硝酰基类”)的有效量,将依据多种因素而变化,包括热塑性聚氨酯的化学组成、是否存在芳族聚合物、存在的着色剂和其它添加剂的类型、加工条件、最后制得的热塑性聚氨酯制品的厚度和透明度与预想的最终用途。
通常,UVA的存在量为0.1~5wt%,基于该热塑性聚氨酯组合物的总重,且选自于选自于2-(2-羟基苯基)-2H-苯并三唑、三-芳基-o-羟基苯基-s-三嗪、2-羟基二苯甲酮、甲脒和草酰替苯胺,和该含至少一种式I硝酰基部分的化合物的存在量为0.1~5wt%,基于该热塑性聚氨酯组合物的总重。
典型地,UVA和含至少一种式I硝酰基部分的化合物一起的总存在量为0.2~5.1wt%,基于该热塑性聚氨酯组合物的总重。
例如,UVA和含至少一种式I硝酰基部分的化合物一起的总存在量为0.2~2wt%,基于该热塑性聚氨酯组合物的总重。
确定UVA和硝酰基类的最佳有效量将仅需要本领域中常见的实验。
硝酰基类为,例如,式Ia的化合物,
其中,
G1和G2独立地为H、1~24个碳原子的烷基或者一起为戊撑,且
Z1和Z2各自为H或甲基,或者Z1和Z2一起形成连接部分,其可以额外地被酯、醚、羟基、氧、氰醇、酰胺、氨基、羧基或尿烷基取代。
上述通式的硝酰基类可以由几乎任意的广泛已知的受阻胺光稳定剂来形成,但是,硝酰基类为自由基且通常是上色的化合物,典型地为橙色或红色。
本发明的硝酰基类为含至少一种式I部分的上色的化合物。
例如,该含至少一种式I硝酰基部分的化合物选自于式A~F的化合物,
m为1、2、3、或4,且
当m为1时,
R1为氢、1~18个碳原子的烷基、2~18个碳原子的链烯基、2~18碳原子的炔基、5~12个碳原子的环烷基,所述烷基、链烯基、炔基或环烷基由一种或多种OR3、苯基、NR3R3′、COOR3、COOM+、CONR3R3′取代一次或多次;
2~18个碳原子的烷基,由环氧乙烷取代;
6~12个碳原子的芳基,所述芳基由1~4种1~4个碳原子的烷基、OR3、NR3R3′、COOR3、COOM+、CONR3R3′取代;
2~18个碳原子的烷基,3~18个碳原子的链烯基,3~18个碳原子的炔基或者5~12个碳原子的环烷基,由一种或多种如前所定义的基团X间断一次或多次,所述间断的烷基、链烯基、炔基或环烷基由一种或多种OR3、苯基、NR3R3′、COOR3、COOM+、CONR3R3′取代一次或多次;
其中R3和R3′彼此独立地为氢,1~18个碳原子的烷基,由氧间断一次或多次的1~18个碳原子的烷基,5~12个碳原子的环烷基,6~12个碳原子的芳基,所述芳基由1~4种1~4个碳原子的烷基取代,7~12个碳原子的芳烷基,或者2~18个碳原子的烷基羰基,6~13个碳原子的环烷基羰基,7~13个碳原子的芳基羰基,所述芳基由1~4种1~4个碳原子的烷基取代;
且M+为元素周期表第一、第二或第三族的金属离子或者为Zn、Cu、Ni或Co,或者M为基团Nn+(R2)4,其中R2为1~8个碳原子的烷基或苄基;
当m为2时,
R1为1~12个碳原子的亚烷基,2~12个碳原子的亚链烯基,5~12个碳原子的亚环烷基,7~15个碳原子的亚芳烷基或者6~12个碳原子的亚芳基,被一种或多种O、-NR3-、-CONR3-、-COO-间断一次或多次的2~12个碳原子的亚烷基,
且当m为2且X为直接键时,
R1为-N(R3)R4N(R3)-,其中,R4为2~18个碳原子的亚烷基,5~12个碳原子的亚环烷基,8~15个碳原子的亚芳烷基或6~12个碳原子的亚芳基或者R1为-COO-或-NH-CO-NH-;
当m为3时,
R2为3~8个碳原子的链烷三基或者苯三基,和
当m为4时,
R2为5~8个碳原子的链烷四基或者苯四基:
R10为氢,1~18个碳原子的烷基,5~12个碳原子的环烷基,7~15碳原子的芳烷基,2~18个个碳原原子的烷酰基,3~5个碳原子链烯酰基或苯甲酰基:
其中,k为1或2,
当k为1时,
R20和R21独立地为1~12个碳原子的烷基,2~12个碳原子的链烯基或者7~15个碳原子的芳烷基,或者
R20和R21一起为2~8个碳原子的亚烷基或羟基取代的所述亚烷基,或者为4~22个碳原子的酰氧基-亚烷基,或者
当k为2时,
R20和R21一起为(-CH2)2C(CH2-)2:
R30为氢,1~18个碳原子的烷基,苄基,缩水甘油基,或2~6个碳原子的烷氧基烷基,
g为1或2,
当g为1时,R31为氢、1~18个碳原子的烷基、2~18个碳原子的链烯基、炔丙基、缩水甘油基、由1~20个氧原子间断的2~50个碳原子的烷基,所述烷基由1~10个羟基取代或者同时由所述氧原子间断和由所述羟基取代,或者
R31为由羧基或由-COOZ(其中Z为氢)取代的1~4个碳原子的烷基,1~4个碳原子的烷基或苯基,或者其中Z为由-(COO-)nMn+取代的所述烷基,其中n为1~3且M为元素周期表第一、第二或第三族的金属离子或者为Zn、Cu、Ni或Co,或者M为基团Nn+(R2)4,其中R2为1~8个碳原子的烷基或苄基;
当g为2时,R31为1~12个碳原子的亚烷基,4~12个碳原子的亚链烯基,亚二甲苯基或由1~20个氧原子间断的1~50个碳原子的亚烷基,由1~10个羟基取代或者同时由所述氧原子间断和由所述羟基取代。
例如,该含至少一种式I硝酰基部分的化合物选自式A、B、C和D的化合物,
其中,式A中
m为1或2,且
当m为1时,
R1为氢,1~18个碳原子的烷基,2~18个碳原子的链烯基,所述烷基或链烯基由一种或多种OR3、COOR3或CONR3R3′取代;
3~12个碳原子的烷基,由环氧乙烷取代;
当m为2时,
R1为1~12个碳原子的亚烷基,2~12个碳原子的亚链烯基,被一种或多种O、-CONR3-、-COO-间断一次或多次,和/或由OR3取代一次或多次。
例如,本发明的硝酰基化合物选自于双(1-氧基-2,2-6-6-四甲基哌啶-4-基)癸二酸酯;1-氧基-2,2,6,6-四甲基-4-乙酰胺基哌啶;1-氧基-2,2,6,6-四甲基-4-氧-哌啶;1-氧基-2,2,6,6-四甲基-4-甲氧基-哌啶;1-氧基-2,2,6,6四甲基-4-乙酸基哌啶;1-氧基-2,2,6,6-四甲基-4-丙氧基-哌啶;1-氧基-2,2,6,6-四甲基-4-丙酸基-哌啶;1-氧基-2,2,6,6-四甲基-4-硬脂酸基-哌啶和1-氧基-2,2,6,6-四甲基-4-羟基哌啶。
可以一起使用一种以上的UVA。可以一起使用一种以上的硝酰基化合物。
本紫外光吸收剂和含硝酰基的化合物采用标准技术来引入,其中要求在高温下。可以将该UVA和硝酰基类一起或分开加入。例如,通过挤出、共混、乳化、溶液浇铸、brabender混合等将UVA和硝酰基类引入。
本发明组合物的热塑性聚氨酯聚合物是已知的且可以是线性的、支化的或交联的。
在制备本发明的组合物时,在本发明的范围之内,能够将紫外光吸收剂和/或含硝酰基的化合物加到多元醇或聚氨酯的异氰酸酯前体中,但是,典型地将该紫外光吸收剂和含硝酰基的化合物加到热塑性聚氨酯聚合物中,但是另外也可以存在多元醇和/或异氰酸酯。
例如,将该紫外光吸收剂和含硝酰基的化合物与热塑性聚氨酯树脂和其它任选的添加剂共混,且由此形成在高温下挤出的混合物,例如,在140℃~250℃的温度下进行挤出;例如在160℃~240℃的温度下进行挤出;例如在170℃~220℃的温度下进行挤出。
本发明的热塑性聚氨酯组合物可以进行另外的加工,包括引入紫外光吸收剂和含硝酰基的化合物之后热、机械和化学加工。
例如,可以在引入紫外光吸收剂和含硝酰基的化合物之后将该热塑性聚氨酯组合物在高温下进一步加工,例如,在大于45℃的温度或者大于70℃的温度下。
本发明的热塑性聚氨酯组合物可以以任意加工形式存在,包括板材、饰板、球粒、其它模塑制品、纤维、膜、粉末等。
本发明的颜色牢固的热塑性聚氨酯组合物可以形成多层物体的一层,例如,通过将本聚氨酯组合物的熔体施用到现有制品的表面上。含作为一层的本热塑性聚氨酯组合物的多层制品也可以通过共挤出来获得,由此形成板材或其它模塑制品或铠装纤维。
也可以将本发明的颜色牢固的热塑性聚氨酯组合物施用到现有制品的表面上,通过制备该热塑性聚氨酯组合物的乳液,例如粉末或薄片形式的,在诸如水的溶剂中,并将该乳液施用到制品的表面上。
例如,该另外的加工包括选自下列的步骤:干燥、固化、加热、硬化、模塑、混炼、压延、浇铸、吹塑、固化、喷雾、压塑、共混、交联、进一步聚合、扩链、挤出、共挤出、拉伸、纤维制造、干燥、着色、研磨、悬浮、乳化、涂布。
在引入紫外光吸收剂和含硝酰基的化合物之后可以将该热塑性聚氨酯组合物的聚氨酯聚合物或其它组分进一步聚合、交联或化学转化。
例如,可以将该聚氨酯聚合物通过与另外的多元醇或异氰酸酯反应而进一步聚合、或者与甲醛或其它扩链剂反应以形成更长的聚合物链、或者采用传统交联剂交联。
特定实施方式提供了包含芳族热塑性聚氨酯的颜色牢固的组合物和它们的制备方法。
通常,本发明的热塑性聚氨酯组合物也含有着色剂如染料或颜料。特定实施方式涉及着色的组合物。
本发明的热塑性聚氨酯组合物将典型地含有其它添加剂。常用添加剂包括,抗氧剂,光稳定剂,包括受阻胺、亚磷酸酯或亚膦酸酯,苯并呋喃-2-酮、硫代增效剂,聚酰胺稳定剂,金属硬脂酸盐,成核剂,填料,补强剂,润滑剂,乳化剂,染料,颜料,分散剂,其它荧光增白剂,阻燃剂,抗静电剂,发泡剂等或其混合物。
例如,本发明的组合物也可以包括抗氧剂和/或N-H、N-烷基、N-OR、N-酰基或N-OH受阻胺光稳定剂。
常用聚合物添加剂的具体实例包括:
1.抗氧剂
1.1.烷基化单酚,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-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,2,6-二十八烷基-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,壬基苯酚,其侧链为线性或支化的,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,及其混合物。
1.2.烷基硫代甲基苯酚,例如2,4-二辛基硫代甲基-6-叔丁基苯酚,2,4-二辛基硫代甲基-6-甲基苯酚,2,4-二辛基硫代甲基-6-乙基苯酚,2,6-二-十二烷基硫代甲基-4-壬基苯酚。
1.3.对苯二酚和烷基化对苯二酚,例如2,6-二-叔丁基-4-甲氧基苯酚,2,5-二-叔丁基对苯二酚,2,5-二-叔丁基对苯二酚,2,6-二苯基-4-十八烷基氧基苯酚,2,6-二-叔丁基对苯二酚,2,5-二-叔丁基-4-羟基茴香醚,3,5-二-叔丁基-4-羟基茴香醚,3,5-二-叔丁基-4-羟基苯基硬脂酸酯,双-(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.羟基化硫代二苯基醚,例如2,2′-硫代双(6-叔丁基-4-甲基苯酚),2,2′-硫代双(4-辛基苯酚),4,4′-硫代双(6-叔丁基-3-甲基苯酚),4,4′-硫代双(6-叔丁基-2-甲基苯酚),4,4′-硫代双-(3,6-二-仲戊基苯酚),4,4′-双(2,6-二甲基-4-羟基苯基)二硫化物。
1.6.次烷基双苯酚,例如2,2′-次甲基双(6-叔丁基-4-甲基苯酚),2,2′-次甲基双(6-叔丁基-4-乙基苯酚),2,2′-次甲基双[4-甲基-6-(α-甲基环己基)苯酚],2,2′-次甲基双(4-甲基-6-环己基苯酚),2,2′-次甲基双(6-壬基-4-甲基苯酚),2,2′-次甲基双(4,6-二-叔丁基苯酚),2,2′-次乙基双(4,6-二-叔丁基苯酚),2,2′-次乙基双(6-叔丁基-4-异丁基苯酚),2,2′-次甲基双[6-(α-甲基苄基)-4-壬基苯酚],2,2′-次甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4′-次甲基双(2,6-二叔丁基苯酚),4,4′-次甲基双(6-叔丁基-2-甲基苯酚),1,1-双(5-叔丁基-4-羟基-2-甲基苯弎)丁烷,2,6-双(3-叔丁基-5-甲基-2-羟基苄基)-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-双(5-叔丁基-4-羟基-2-甲基-苯基)-3-正-十二烷基巯基丁烷,乙二醇双[3,3-双(3-叔丁基-4-羟基苯基)丁酸酯],双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯,双[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-双-(3,5-二甲基-2-羟基苯基)丁烷,2,2-双-(3,5-二-叔丁基-4-羟基苯基)丙烷,2,2-双-(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.苄基化合物,例如3,5,3′,5′-四-叔丁基-4,4′-二羟基二苄基醚,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,1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲基苯,二-(3,5-二-叔丁基-4-羟基苄基)硫化物,3,5-二-叔丁基-4-羟基苄基-巯基-乙酸异辛基酯,双-(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫醇对苯二甲酸酯,1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)异氰脲酸酯,1,3,5-三-(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯,3,5-二-叔丁基-4-羟基苄基-磷酸二十八烷基酯和3,5-二-叔丁基-4-羟基苄基-磷酸单乙基酯,钙盐。
1.8.羟基苄基化丙二酸酯,例如二十八烷基-2,2-双-(3,5-二-叔丁基-2-羟基苄基)-丙二酸酯,二-十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)-丙二酸酯,二-十二烷基巯基乙基-2,2-双-(3,5-二-叔丁基-4-羟基苄基)丙二酸酯,双[4-(1,1,3,3-四甲基丁基)苯基]-2,2-双(3,5-二-叔丁基-4-羟基苄基)丙二酸酯。
1.9.芳族羟基苄基化合物,例如1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲基苯,1,4-双(3,5-二-叔丁基-4-羟基苄基)-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-双(辛基巯基)-6-(3,5-叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛基巯基-4,6-双(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-羟基苄基)异氰脲酸酯,1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯,2,4,6-三(3,5-二-叔丁基-4-羟基苯基乙基)-1,3,5-三嗪,1,3,5-三(3,5-二-叔丁基-4-羟基苯基丙酰基)-六氢-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟基苄基)异氰脲酸酯。
1.11.苄基膦酸酯,例如二甲基-2,5-二-叔丁基-4-羟基苄基膦酸酯,二乙基-3,5-二-叔丁基-4-羟基苄基膦酸酯,二十八烷基3,5-二-叔丁基-4-羟基苄基膦酸酯,二十八烷基-5-叔丁基-4-羟基-3-甲基苄基膦酸酯,3,5-二-叔丁基-4-羟基苄基磷酸的单乙基酯的钙盐。
1.12.酰基氨基苯酚,例如4-羟基-月桂酸酰替苯胺,4-羟基-硬脂酸酰替苯胺,2,4-双-辛基巯基-6-(3,5-叔丁基-4-羟基苯胺基)-s-三嗪和辛基-N-(3,5-二-叔丁基-4-羟基苯基)-氨基甲酸酯。
1.13.β-(3,5-二-叔丁基-4-羟基苯基)丙酸与单-或多羟基纯的酯,例如与甲醇,乙醇,n-辛醇,i-辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,乙二醇,1,2-丙烷二醇,新戊二醇,硫代二乙二醇,二乙二醇,三乙二醇,季戊四醇,三(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫代十一醇,3-硫代十五醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-1-.磷杂-2,6,7-三氧双环[2.2.2]辛烷。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与单-或多羟基醇的酯,例如与甲醇,乙醇,n-辛醇,i-辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,乙二醇,1,2-丙烷二醇,新戊二醇,硫代二乙二醇,二乙二醇,三乙二醇,季戊四醇,三(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫代十一醇,3-硫代十五醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-1-.磷杂-2,6,7-三氧双环[2.2.2]辛烷。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸与单-或多羟基醇的酯,例如甲醇,乙醇,n-辛醇,i-辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,乙二醇,1,2-丙烷二醇,新戊二醇,硫代二乙二醇,二乙二醇,三乙二醇,季戊四醇,三(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫代十一醇,3-硫代十五醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-1-.磷杂-2,6,7-三氧双环[2.2.2]辛烷。
1.16.3,5-二-叔丁基-4-羟基苯基乙酸与单-或多羟基醇的酯,例如与甲醇,乙醇,n-辛醇,i-辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,乙二醇,1,2-丙烷二醇,新戊二醇,硫代二乙二醇,二乙二醇,三乙二醇,季戊四醇,三(羟基乙基)异氰脲酸酯,N,N′-双(羟基乙基)草酰胺,3-硫代十一醇,3-硫代十五醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-1-.磷杂-2,6,7-三氧双环[2.2.2]辛烷。
1.17.β-(3,5-二-叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N′-双(3,5-二叔丁基-4-羟基苯基丙酰基)六次甲基二酰胺,N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)三次甲基二酰胺,N,N′-双(3,5-二叔丁基-4-羟基-苯基丙酰基)酰肼,N,N′-双[2-(3-[3,5-二-叔丁基-4-羟基苯基]丙酸基)-乙基]草酰胺。
1.18.抗坏血酸(维生素C)
1.19.胺化抗氧剂,例如N,N′-二-异丙基-p-亚苯基二胺,N.N′-二-仲-丁基-p-亚苯基二胺,N,N′-双(1,4-二甲基戊基)-p-亚苯基二胺,N,N′-双(1-乙基-3-甲基戊基)-p-亚苯基二胺,N,N′-双(1-甲基庚基)-p-亚苯基-二胺,N.N′-二环己基-p-亚苯基二胺,N,N′-二苯基-p-亚苯基二胺,N1 N′-双(2-萘基)-p-亚苯基二胺,N-异丙基-N′-苯基-p-亚苯基二胺,N-(1,3-二甲基丁基)-N′-苯基-p-亚苯基二胺,N-(1-甲基庚基)-N′-苯基-p-亚苯基-二胺,N-环己基-N′-苯基-p-亚苯基二胺,4-(p-甲苯氨磺酰)二苯基胺,N,N′-二甲基-N,N′-二-仲-丁基-p-亚苯基二胺,二苯基胺,N-烯丙基二苯基胺,4-异丙氧基二苯基胺,N-苯基-1-苯基胺,N-(4-叔-辛基苯基)-1-萘基-胺,N-苯基-2-萘基胺,辛基化二苯基胺,例如p,p′-二-叔-辛基二苯基胺,4-正丁基氨基苯酚,4-丁酰基氨基苯酚,4-壬酰基氨基苯酚,4-十二烷酰基氨基苯酚,4-十八烷酰基氨基苯酚,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,N1N′,N′-四甲基-4,4′-二氨基二苯基甲烷,1,2-双[(2-甲基苯基)氨基]乙烷,1,2-双(苯基氨基)丙烷,(o-甲苯基)双胍,双[4-(1′,3′-二甲基丁基)苯基]胺,tert-辛基化N-苯基-1-萘基胺,单-和二烷基化叔丁基/叔-辛基-二苯基胺的混合物,单-和二烷基化壬基二苯基胺的混合物,单-和二烷基化十二烷基二苯基胺的混合物,单-和二烷基化异丙基/异己基二苯基胺的混合物,单-和二烷基化叔丁基二苯基胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,酚噻嗪,单-和二烷基化叔丁基/叔-辛基酚噻嗪的混合物,单-和二烷基化叔-辛基-酚噻嗪的混合物,N-烯丙基酚噻嗪,N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯,N,N-双(2,2,6,6-四甲基-哌啶-4-基-六次甲基二胺,双(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
2.12-(2-羟基苯基)-2H-苯并三唑,例如,美国专利3,004,896、3,055,896、3,072,585、3,074,910、3,189,615、3,218,332、3,230,194、4,127,586、4,226,763、4,275,004、4,278,589、4,315,848、4,347,180、4,383,863、4,675,352、4,681,905,4,853,471、5,268,450、5,278,314、5,280,124、5,319,091、5,410,071、5,436,349、5,516,914、5,554,760、5,563,242、5,574,166、5,607,987和5,977,21中所公开的已知商品化的羟基-2H-苯并三唑和苯并三唑,如2-(2-羟基-5-甲基苯基)-2H-苯并三唑,2-(3,5-二-t-丁基-2-羟基苯基)-2H-苯并三唑,2-(2-羟基-5-t-丁基苯基)-2H-苯并三唑,2-(2-羟基-5-t-辛基苯基)-2H-苯并三唑,5-氯-2-(3,5-二-t-丁基-2-羟基苯基)-2H-苯并三唑,5-氯-2-(3-t-丁基-2-羟基-5-甲基苯基)-2H-苯并三唑,2-(3-仲-丁基-5-t-丁基-2-羟基苯基)-2H-苯并三唑,2-(2-羟基-4-辛基氧基苯基)-2H-苯并三唑,2-(3,5-二-t-戊基-2-羟基苯基)-2H-苯并三唑,2-(3,5-双-α-枯基-2-羟基苯基)-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-(ω-羟基-八-(亚乙基氧基)-羰基-乙基)-,苯基)-2H-苯并三唑,2-(3-十二烷基-2-羟基-5-甲基苯基)-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-辛基氧基羰基)乙基苯基)-2H-苯并三唑,十二烷基化2-(2-羟基-5-甲基苯基)-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-辛氧基羰基乙基)苯基)-5-氯-2H-苯并三唑,2-(3-叔丁基-5-(2-(2-乙基己氧基)-羰基乙基)-2-羟基苯基)-5-氯-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-甲氧基羰基乙基)苯基)-5-氯-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-甲氧基羰基乙基)苯基)-2H-苯并三唑,2-(3-t-丁基-5-(2-(2-乙基己氧基)羰基乙基)-2-羟基苯基)-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-异辛氧基羰基乙基)-苯基-2H-苯并三唑,2,2′-亚甲基-双(4-t-辛基-(6-2H-苯并三唑-2-基)苯酚),2-(2-羟基-3-α-枯基-5-t-辛基苯基)-2H-苯并三唑,2-(2-羟基-3-t-辛基-5-α-枯基苯基)-2H-苯并三唑,5-氟-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑,5-氯-2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑,5-氯-2-(2-羟基-3-α-枯基-5-t-辛基苯基)-2H-苯并三唑,2-(3-t-丁基-2-羟基-5-(2-异辛氧基羰基-乙基)苯基)-5-氯-2H-苯并三唑,5-三氟甲基-2-(2-羟基-3-α-枯基-5-t-辛基-苯基)-2H-苯并三唑,5-三氟甲基-2-(2-羟基-5-t-辛基苯基)-2H-苯并三唑,5-三氟甲基-2-(2-羟基-3,5-二-t-辛基苯基)-2H-苯并三唑,甲基3-(5-三氟-甲基-2H-苯并三唑-2-基)-5-t-丁基-4-羟基氢肉桂酸酯,5-丁基磺酰基-2-(2-羟基-3-α-枯基-5-t-辛基苯基)-2H-苯并三唑,5-三氟甲基-2-(2-羟基-3-α-枯基-5-t-丁基苯基)-2H-苯并三唑,5-三氟甲基基-2-(2-羟基-3,5-二-t-丁基苯基)-2H-苯并三唑,5-三氟甲基-2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑,5-丁基磺酰基-2-(2-羟基-3,5-二-t-丁基苯基)-2H-苯并三唑和5-苯基磺酰基-2-(2-羟基-3,5-二-t-丁基苯基)-2H-苯并三唑。
2.2.2-羟基二苯甲酮,例如4-羟基,4-甲氧基,4-辛氧基,4-癸氧基,4-十二烷氧基,4-苄基氧基,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的酯,例如4-叔丁基-苯基水杨酸酯,苯基水杨酸酯,辛基苯基水杨酸酯,二苯甲酰基间苯二酚,双(4-叔丁基苯甲酰基)间苯二酚,苯甲酰基间苯二酚,2,4-二-叔丁基苯基3,5-二-叔丁基-4-羟基苯甲酸酯,十六烷基3,5-二-叔丁基-4-羟基苯甲酸酯,十八烷基3,5-二-叔-丁基-4-羟基苯甲酸酯,2-甲基-4,6-二-叔丁基苯基3,5-二-叔丁基-4-羟基-苯甲酸酯。
2.4.丙烯酸酯和丙二酸酯,例如,α-氰基-β,β-二苯基丙烯酸乙基酯或异辛基酯,α-碳甲氧基-肉桂酸甲基酯,α-氰基-β-甲基-p-甲氧基-肉桂酸甲基酯或丁基酯,α-碳甲氧基-p-甲氧基-肉桂酸甲基酯,N-(β-碳甲氧基-β-氰基乙烯基)-2-甲基-吲哚,二甲基p-甲氧基亚苄基丙二酸酯(CAS#7443-25-6),和二-(1,2,2,6,6-五甲基哌啶-4-基)p-甲氧基亚苄基丙二酸酯(CAS#147783-69-5)。
2.5.镍化合物,例如2,2′-硫代-双-[4-(1,1,3,3-四甲基丁基)苯酚]的镍络合物,如1∶1和1∶2络合物,使用或不使用其它配体如n-丁基胺,三乙醇胺或N-环己基二乙醇胺,二丁基二硫代氨基甲酸镍,单烷基酯的镍盐,例如甲基或乙基酯,4-羟基-3,5-二-叔丁基苄基膦酸的,酮肟的镍络合物,例如2-羟基-4-甲基苯基十-烷基酮肟,1-苯基-4-月桂酰基-5-羟基吡唑的镍络合物,使用或不使用其它配体。
2.6.空间受阻胺稳定剂,例如4-羟基-2,2,6,6-四甲基哌啶,1-烯丙基-4-羟基-2,2,6,6-四甲基哌啶,1-苄基-4-羟基-2,2,6,6-四甲基哌啶,双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,双(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基-4-哌啶基)n-丁基-3,5-二-叔丁基-4-羟基苄基丙二酸酯,1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物,N,N′-双(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-1,3,5-三嗪的线性或环状缩合物,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-乙烷二基)-双(3,3,5,5-四甲基哌嗪酮),4-苯甲酰基-2,2,6,6-四甲基哌啶,4-硬脂酸基-2,2,6,6-四甲基哌啶,双(1,2,2,6,6-五甲基哌啶基)-2-n-丁基-2-(2-羟基-3,5-二-叔-丁基苄基)丙二酸酯,3-n-辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸-2,4-二酮,双(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,双(1-辛氧基-2,2,6,6-四甲基-哌啶基)琥珀酸酯,N,N′-双-(2,2,6,6-四甲基-4-哌啶基)-六亚甲基二胺和4-吗啉基-2,6-二氯-1,3,5-三嗪的线性或环状缩合物,2-氯-4,6-双(4-n-丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物,2-氯-4,6-二-(4-n-丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-双-(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-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-硬脂酸基-2,2,6,6-四甲基哌啶的混合物,N,N′-双(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-1,3,5-三嗪的缩合产物,1,2-双(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合物产物,以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6]);N-(2,2,6,6-四甲基-4-哌啶基)-n-十二烷基琥珀酰亚胺,N-(1,2,2,6,6-五甲基-4-哌啶基)-n-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-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-螺[4,5]癸烷和表氯醇的反应产物,1,1-双(1,2,2,6,6-五甲基-4-哌啶基氧基羰基)-2-(4-甲氧基苯基)乙烯,N,N′-双-甲酸基-N,N′-双(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-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅烷,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。
该空间受阻胺也可以是GB-A-2301106中所述的一种组分I-a),I-b),I-c),I-d),I-e),I-f),I-g),I-h),I-i),I-j),I-k)或I-l),特别是所述GB-A-2301106的第68~73中所列的光稳定剂1-a-1,1-a-2,1-b-1,1-C-1,1-C-2,1-d-1,1-d-2,1-d-3,1-e-1,1-f-1,1-g-1,1-g-2或1-k-1。
该空间受阻胺也可以是EP 782994中所述的一种化合物,例如其中权利要求10或38或者实施例1-12或D-1~D-5中所述的化合物。
该空间位阻胺也可以是受阻胺光稳定剂的羟基胺或羟基胺盐。
2.7.在N-原子上被羟基-烷氧基取代的空间受阻胺,例如化合物,如1-(2-羟基-2-甲基丙基)-4-十八烷酸基-2,2,6,6-四甲基哌啶,1-(2-羟基-2-甲基丙氧基)-4-十六烷酸基-2,2,6,6-四甲基哌啶,1-氧基-4-羟基-2,2,6,6-四甲基哌啶与t-戊醇中的碳自由基的反应产物,1-(2-羟基-2-甲基丙氧基)-4-羟基-2,2,6,6-四甲基哌啶,1-(2-羟基-2-甲基丙氧基)-4-氧杂-2,2,6,6-四甲基哌啶,双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基-哌啶-4-基)癸二酸酯,双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)己二酸酯,双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯,双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)戊二酸酯和2,4-双{N-[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]-N-丁基氨基}-6-(2-羟基乙基氨基)-s-三嗪。
2.8.草酰胺,例如4,4′-二辛氧基草酰替苯胺,2,2′-二乙氧基草酰替苯胺,2,2′-二辛氧基-5,5′-二叔丁基草酰替苯胺,2,2′-二十二烷基氧基-5,5′-二-叔丁基草酰替苯胺,2-乙氧基-2′-乙基草酰替苯胺,N,N′-双(3-二甲基氨基丙基)草酰胺,2-乙氨基-5-叔丁基-2′-乙基草酰替苯胺,及其与2-乙氧基-2′-乙基-5,4′-二-叔丁基草酰替苯胺的混合物,o-与p-甲氧基-二取代的草酰替苯胺的混合物和o-与p-乙氧基-二取代的草酰替苯胺的混合物。
2.9.三-芳基-o-羟基苯基-s-三嗪,例如WO 96/28431,EP 434608,EP 941989,GB 2,317,893,美国专利3,843,371、4,619,956、4,740,542、5,096,489、5,106,891、5,298,067、5,300,414、5,354,794、5,461,151、5,476,937、5,489,503、5,543,518、5,556,973、5,597,854、5,681,955、5,726,309、5,942,626、5,959,008、5,998,116和6,013,704中所公开的已知商业化的三-芳基-o-羟基苯基-s-三嗪和三嗪,例如4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-辛氧基苯基)-s-三嗪,Cyasorb1164,Cytec Corp,4,6-双-(2,4-二甲基苯基)-2-(2,4-二羟基苯基)-s-三嗪,2,4-双(2,4-二羟基苯基)-6-(4-氯苯基)-s-三嗪,2,4-双[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-双[2-羟基-4-(2-羟基-4-(2-羟基乙氧基)苯基)-6-(2,4-二甲基苯基)-s-三嗪,2,4-双[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-溴苯基)-s-三嗪,2,4-双[2-羟基-4-(2-乙酸基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-双(2,4-二羟基苯基)-6-(2,4-二甲基苯基)-s-三嗪,2,4-双(4-联苯基)-6-(2-羟基-4-辛氧基羰基亚乙基-氧基苯基)-s-三嗪,2-苯基-4-[2-羟基-4-(3-仲-丁氧基-2-羟基丙氧基)苯基]-6-[2-羟基-4-(3-仲-戊氧基-2-羟基丙氧基)苯基]-s-三嗪,2,4-双(2,4-二甲基-苯基)-6-[2-羟基-4-(3-苄基氧基-2-羟基丙氧基)苯基]-s-三嗪,2,4-双(2-羟基-4-n-丁氧基苯基)-6-(2,4-二-n-丁氧基苯基)-s-三嗪,2,4-双(2,4-二甲基-苯基)-6-[2-羟基-4-(3-壬氧基*-2-羟基丙氧基)-5-α-枯基苯基]-s-三嗪(*表示辛氧基,壬氧基和癸氧基的混合物),亚甲基双-{2,4-双(2,4-二甲基苯基)-6-[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-s-三嗪},亚甲基桥连的二聚体混合物,以5∶4∶1比例在3∶5′,5∶5′和3∶3′位置上桥连,2,4,6-三(2-羟基-4-异辛氧基羰基亚异丙基氧基苯基)-s-三嗪,2,4-双(2,4-二甲基-苯基)-6-(2-羟基-4-己氧基-5-α-枯基苯基)-s-三嗪,2-(2,4,6-三甲基基)-4,6-双[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-s-三嗪,2,4,6-三[2-羟基-4-(3-仲-丁氧基-2-羟基丙氧基)苯基]-s-三嗪,4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-(3-十二烷基氧基-2-羟基丙氧基)-苯基)-s-三嗪和4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-(3-十三烷基氧基-2-羟基丙氧基)-苯基)-s-三嗪的混合物,4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-(3-(2-乙基己氧基)-2-羟基丙氧基)-苯基)-s-三嗪和4,6-二苯基-2-(4-己氧基-2-羟基苯基)-s-三嗪。
3.金属钝化剂,例如N,N′-二苯基草酰胺,N-水杨醛-N′-水杨酰基肼,N,N′-双(水杨酰基)肼,N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)肼,3-水杨酰基氨基-1,2,4-三唑,双(亚苄基)草酰基二酰肼,草酰替苯胺,间苯二甲酰基二酰肼,癸二酰基双苯基酰肼,N,N′-二乙酰基己二酰基二酰肼,N,N′-双(水杨酰基)草酰基二酰肼,N,N′-双(水杨酰基)硫代丙酰基二酰肼。
4.亚磷酸酯和亚膦酸酯,例如三苯基亚磷酸酯,二苯基烷基亚磷酸酯,苯基二烷基亚磷酸酯,三(壬基苯基)亚磷酸酯,三月桂基亚磷酸酯,三十八烷基亚磷酸酯,二硬脂基季戊四醇二亚磷酸酯,三(2,4-二-叔丁基苯基)亚磷酸酯,二异癸基季戊四醇二亚磷酸酯,双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯,双(2,6-二-叔丁基-4-甲基苯基)-季戊四醇二亚磷酸酯,二异癸基氧基季戊四醇二亚磷酸酯,双(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯,双(2,4,6-三(叔丁基苯基)季戊四醇二亚磷酸酯,三硬脂基山梨糖醇三亚磷酸酯,四(2,4-二叔丁基苯基)4,4′-亚联苯基二亚膦酸酯,6-异辛基氧基-2,4,8,10-四-叔丁基-二苯并[d,f][1,3,2]二氧杂phosphepin,6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g][1,3,2]二氧杂phosphocin,双(2,4-二-叔丁基-6-甲基苯基)甲基亚磷酸酯,双(2,4-二-叔丁基-6-甲基苯基)乙基亚磷酸酯,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.苯并呋喃酮和吲哚酮,例如美国专利4,325,863,4,338,244,5,175,312,5,216,052,5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839或EP-A-0591 102中所公开的那些,或者3-[4-(2-乙酸基乙氧基)苯基]-5,7-二-叔丁基-苯并呋喃-2-酮,5,7-二-叔丁基-3-[4-(2-硬脂酸基乙氧基)苯基]苯并呋喃-2-酮,3,3′-双[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-乙酸基-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-新戊酸基-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,和3-(2,3-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮。
6.羟基胺,例如N,N-二苄基羟基胺,N,N-二乙基羟基胺,N,N-二辛基羟基胺,N,N-二月桂基羟基胺,N,N-二十四烷基羟基胺,N,N-二十六烷基羟基胺,N,N-二十八烷基羟基胺,N-十六烷基-N-十八烷基羟基胺,N-十七烷基-N-十八烷基羟基胺,N-甲基-N-十八烷基羟基胺和由氢化牛脂胺获得的N,N-二烷基羟基胺。
7.硝酮类,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-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,N-甲基-α-十七烷基硝酮和由衍生自氢化牛脂胺的N,N-二烷基羟基胺的硝酮。
8.胺氧化物,例如胺氧化物言衍生物,如美国专利5,844,029和5,880,191中所公开的,二癸基甲基胺氧化物,十三烷基胺氧化物,三十二烷基胺氧化物和三十六烷基胺氧化物。
9.硫代增效剂,例如二月桂基硫代二丙酸酯或二硬脂基硫代二丙酸酯。
10.过氧化物清除剂,例如β-硫代二丙酸的酯,例如月桂基,硬脂基,肉豆蔻基或十三烷基酯,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,二十八烷基二硫化物,季戊四醇四([β-十二烷基巯基]丙酸酯。
11.聚酰胺稳定剂,例如铜盐与碘化物组合和/或磷化合物和二价锰的盐。
12.碱性助稳定剂,例如蜜胺,聚乙烯基吡咯烷酮,二氰基二酰胺,三烯丙基氰尿酸酯,尿烷衍生物,肼衍生物,胺,聚酰胺,聚氨酯,高级脂肪酸的碱金属盐和碱土金属盐,例如硬脂酸钙、硬脂酸锌、山嵛酸镁、硬脂酸镁、蓖麻醇酸钠和棕榈酸钾,锑pyrocatecholate或锌pyrocatecholate。
13.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,优选碱土金属的;有机化合物如单-或多羧酸和其盐,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;高分子化合物如离子共聚物(离聚体)。
14.填料和补强剂,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,碳黑,石墨,木粉和其它天然产品的粉末或纤维,合成纤维。
15.分散剂,如聚环氧乙烷蜡扩矿物油。
16.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,染料,其它光学增白剂,流变学添加剂,催化剂,流动控制剂,滑爽剂,交联剂,交联促进剂,卤素清除剂,烟雾抑制剂,阻燃剂,抗静电剂,澄清剂如取状和未取代的双亚苄基山梨糖醇,苯并恶嗪酮UV吸收剂如2,2′-p-亚苯基-双(3,1-苯并恶嗪-4-酮),和发泡剂。
着色剂,例如染料和颜料通常存在于本发明的热塑性聚氨酯组合物中,且包括有机和无机着色剂。可以起到仅添加颜色之外的作用的着色剂化合物,如二氧化钛和碳黑,在这些组合物中也是常见的。
确定硝酰基类、UVA和/或HALS或其它任选添加剂的最佳有效量时,必须考虑影响聚氨酯组合物的颜色变化的所有因素。例如,最初颜色和可归因于硝酰基类的颜色变化速率和不同聚氨酯聚合物、聚氨酯共聚物或聚氨酯聚合物共混物的褪色速率不同。颜色变化速率也依赖于包括该聚氨酯树脂是否为脂肪族的或芳族的、存在的着色剂和其它添加剂的类型、加工条件和使用条件等因素。硝酰基类和UVA的最佳浓度也依赖于最终制得的热塑性聚氨酯制品的厚度和透明度。由此确定硝酰基类的最有益量将需要诸如这些应用中常见的实验。
本发明的另一方面提供了一种改进聚氨酯组合物在暴露于光时的色牢度的方法,该方法包括将有效量的含至少一种式I硝酰基部分的化合物加到包括热塑性聚氨酯聚合物和紫外光吸收剂的组合物中。
例如,该保持热塑性聚氨酯组合物的色牢度的方法,包括在热塑性聚氨酯组合物中引入一定量的紫外光吸收剂与含至少一种式I硝酰基部分的化合物的混合物,有效地在依据SAE J 1960实验规程在2,500kJ的氙气暴露之后产生的由ΔE测量的颜色变化小于5。
关于上述组合物给出的定义和优选也适用于本发明的其它方面。
通常,通过在140~250℃的温度下进行挤出,将紫外光吸收剂和含至少一种式I硝酰基部分的化合物引入。
例如,在170~220℃温度下进行挤出。
具体实施方式中,在加入紫外光吸收剂与含至少一种式I硝酰基部分的化合物的混合物之后,使该聚氨酯组合物进行另外的处理步骤。
特别地,该另外的处理步骤在处于或高于45℃的温度下发生。
例如,该另外的处理步骤包括选自下列的步骤:干燥、固化、加热、硬化、模塑、混炼、压延、浇铸、吹塑、固化、喷雾、压塑、共混、交联、进一步聚合、扩链、挤出、共挤出、拉伸、纤维制造、干燥、着色、研磨、悬浮、乳化、涂布。
本发明的仍另一方面为紫外光吸收剂与含至少一种式I硝酰基部分的化合物的混合物的用途,
其中,X和Y为H或者一起形成到氧上的双键,
用于限制在UV暴露之后热塑性聚氨酯的褪色在依据SAE J 1960实验规程在2,500kJ的氙气暴露之后由ΔE测量的颜色变化小于5。
下列实施例阐述但并非限定本发明。
实施例
将肖氏硬度~50的商品芳族聚醚基热塑性聚氨酯和各种添加剂包例如UVA、硝酰基类、抗氧剂和/或HALS等的干燥混合物,在具有标准混合螺杆的Leis三tz27mm双螺杆挤出机中挤出。挤出温度为200℃~210℃,筒停留时间为1分钟。将该聚氨酯组合物研磨成珠粒。
压塑制得2×2英寸、60mil厚的上述配方的饰板,并依据SAE J 1960试验规程在氙气风化仪中暴露于UV光,2500kJ的总UV暴露。使另一组饰板进行QUV/B暴露115小时。依据ASTM E-313测量UV暴露前后的颜色,DCI SF600分光光度计,Large Area View,刨括谱分量,D65光源,10°观测器。
含本发明的UVA/硝酰基类组合的饰板相对于无硝酰基化合物的饰板显示显著更低的ΔE(颜色变化,也称作DE)。
依照上述一般工序制得含UVA、硝酰基类和抗氧剂的热塑性聚氨酯饰板。改变硝酰基类的浓度且ΔE显示依赖于硝酰基类浓度。
依照上述工序,制备肖氏硬度~50的商品芳族聚醚基热塑性聚氨酯的下列配方,形成饰板并依据汽车内部SAE J 1960试验规程、1989年9月(辐照度,W/m2=0.55光;湿球温降=12℃光;黑板温度=38温度黑,89℃光;调节水=40℃黑,63℃光;循环:3.8小时光/1小时暗度;石英/硼硅酸盐过滤器)在氙气风化仪中暴露于UV光。
在如上所述的1500kJ和2500kJ暴露前后提取颜色。下表中给出了2500kJ之后的ΔE。1500kJ暴露之后仅配方1和2的ΔE小于10。
配方 AO HALS UVA 硝酰基类 ΔE
1 AO1 0% UVA1 A,0.5% <5
2 AO1 HALS 1,0.25% UVA 1 A,0.25% <15
3 AO1 HALS 2,0.5% UVA 2 0% >15
4 AO1 HALS 3,0.5% UVA 1 0% >20
5 AO1 HALS 1,0.5% UVA 3 0% >20
6 AO2 HALS 1,0.5% UVA 1 0% >20
7 AO2 HALS 1,0.5% UVA 3 0% >20
8(空 -- ---- -- -- >40
白)
AO 1=2∶1三乙二醇双[3-(3-叔丁基-4-羟基-5甲基苯基)丙酸酯]∶双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯
AO2=三乙二醇双[3-(3-叔丁基-4-羟基-5甲基苯基)丙酸酯]
HALS1=双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯
HALS2=4-硬脂酸基-2,2,6,6-四甲基哌啶
HALS3=1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物
UVA1=2-(3-十二烷基-2-羟基-5-甲基苯基)-2H-苯并三唑
UVA2=4,6-双-(2,4-二甲基苯基)-2-(2-羟基-4-辛氧基苯基)-s-三嗪
UVA3=2-(3-叔丁基-2-羟基-5-(2-(ω-羟基-八-(亚乙基氧基)羰基-乙基)-苯基)-2H-苯并三唑
再次制备类似配方的饰板并进行暴露,但是配方1和2含有所示浓度的硝酰基类B。得到相同结果,含硝酰基类的配方再次优于其它配方。
Claims (15)
2.权利要求1的组合物,其中该紫外光吸收剂的存在量为0.1~5wt%,基于该热塑性聚氨酯组合物的总重,并且该含至少一种式I硝酰基部分的化合物的存在量为0.1~5wt%,基于该热塑性聚氨酯组合物的总重。
3.权利要求2的组合物,其中该紫外光吸收剂和含至少一种式I硝酰基部分的化合物一起的总存在量为0.2~5.1wt%,基于该热塑性聚氨酯组合物的总重。
4.权利要求3的组合物,其中该紫外光吸收剂和含至少一种式I硝酰基部分的化合物一起的总存在量为0.2~2wt%,基于该热塑性聚氨酯组合物的总重。
5.权利要求1的组合物,其中该含至少一种式I硝酰基部分的化合物选自式A~F的化合物,
m为1、2、3或4,且
当m为1时,
R1为氢、1~18个碳原子的烷基、2~18个碳原子的链烯基、2~18碳原子的炔基、5~12个碳原子的环烷基,所述烷基、链烯基、炔基或环烷基由一种或多种OR3、苯基、NR3R3′、COOR3、COOM+、CONR3R3′取代一次或多次;
2~18个碳原子的烷基,由环氧乙烷取代;
6~12个碳原子的芳基,所述芳基由1~4种1~4个碳原子的烷基、OR3、NR3R3′、COOR3、COOM+、CONR3R3′取代;
2~18个碳原子的烷基、3~18个碳原子的链烯基、3~18个碳原子的炔基或者5~12个碳原子的环烷基,其由一种或多种如前所定义的基团X间断一次或多次,所述间断的烷基、链烯基、炔基或环烷基由一种或多种OR3、苯基、NR3R3′、COOR3、COOM+、CONR3R3′取代一次或多次;
其中R3和R3′彼此独立地为氢,1~18个碳原子的烷基,由氧间断一次或多次的1~18个碳原子的烷基,5~12个碳原子的环烷基,6~12个碳原子的芳基,所述芳基由1~4个1~4个碳原子的烷基取代,7~12个碳原子的芳烷基,或者2~18个碳原子的烷基羰基,6~13个碳原子的环烷基羰基,7~13个碳原子的芳基羰基,所述芳基由1~4个1~4个碳原子的烷基取代;
且M+为元素周期表第一、第二或第三族的金属离子或者为Zn、Cu、Ni或Co,或者M为基团N(R2)4,其中R2为1~8个碳原子的烷基或苄基;
当m为2时,
R1为1~12个碳原子的亚烷基,2~12个碳原子的亚链烯基,5~12个碳原子的亚环烷基,7~15个碳原子的亚芳烷基或者6~12个碳原子的亚芳基,被一种或多种O、-NR3-、-CONR3-、-COO-间断一次或多次的2~12个碳原子的亚烷基,
且当m为2且X为直接键时,
R1为-N(R3)R4N(R3)-,其中,R4为2~18个碳原子的亚烷基,5~12个碳原子的亚环烷基,8~15个碳原子的亚芳烷基或6~12个碳原子的亚芳基或者R1为-COO-或-NH-CO-NH-;
当m为3时,
R1为3~8个碳原子的链烷三基或者苯三基,和
当m为4时,
R1为5~8个碳原子的链烷四基或者苯四基:
R10为氢,1~18个碳原子的烷基,5~12个碳原子的环烷基,7~15个碳原子的芳烷基,2~18个碳原子的烷酰基,3~5个碳原子的链烯酰基或苯甲酰基:
其中,k为1或2,
当k为1时,
R20和R21独立地为1~12个碳原子的烷基,2~12个碳原子的链烯基或者7~15个碳原子的芳烷基,或者
R20和R21一起为2~8个碳原子的亚烷基或羟基取代的所述亚烷基,或者为4~22个碳原子的酰氧基-亚烷基,或者
当k为2时,
R20和R21一起为(-CH2)2C(CH2-)2:
R30为氢,1~18个碳原子的烷基,苄基,缩水甘油基,或2~6个碳原子的烷氧基烷基,
g为1或2,
当g为1时,R31为氢、1~18个碳原子的烷基、2~18个碳原子的链烯基、炔丙基、缩水甘油基、由1~20个氧原子间断的2~50个碳原子的烷基,所述烷基由1~10个羟基取代,或者同时由所述氧原子间断和由所述羟基取代,或者
R31为由羧基或由-COOZ取代的1~4个碳原子的烷基,其中Z为氢、1~4个碳原子的烷基或苯基,或者Z为由-(COO-)nMn+取代的所述烷基,其中n为1~3且M为元素周期表第一、第二或第三族的金属离子或者为Zn、Cu、Ni或Co,或者M为基团N(R2)4,其中R2为1~8个碳原子的烷基或苄基;
当g为2时,R31为1~12个碳原子的亚烷基,4~12个碳原子的亚链烯基,亚二甲苯基或由1~20个氧原子间断、由1~10个羟基取代或者同时由所述氧原子间断和由所述羟基取代的1~50个碳原子的亚烷基。
6.权利要求5的组合物,其中该含至少一种式I硝酰基部分的化合物选自式A、B、C和D的化合物,
其中,式A中
m为1或2,且
当m为1时,
R1为氢,1~18个碳原子的烷基,2~18个碳原子的链烯基,所述烷基或链烯基由一种或多种OR3、COOR3或CONR3R3′取代一次或多次;
3~12个碳原子的烷基,由环氧乙烷取代;
当m为2时,
R1为1~12个碳原子的亚烷基,被一种或多种O、-CONR3-、-COO-间断一次或多次和/或由OR3取代一次或多次的2~12个碳原子的亚烷基。
7.权利要求1的组合物,其中该热塑性聚氨酯组合物包括芳族热塑性聚氨酯。
8.权利要求1的组合物,其还包括至少一种颜料或染料。
9.一种保持热塑性聚氨酯组合物的色牢度的方法,该方法包括在热塑性聚氨酯组合物中引入一定量的紫外光吸收剂与含至少一种如权利要求1定义的式I硝酰基部分的化合物的混合物,有效地在依据SAE J 1960实验规程在2,500kJ的氙气暴露之后产生的由ΔE测量的颜色变化小于5,并且该紫外光吸收剂选自于2-(2-羟基苯基)-2H-苯并三唑类化合物。
10.权利要求9的方法,其中通过在140~250℃的温度下进行挤出,将该紫外光吸收剂和/或该含至少一种式I硝酰基部分的化合物引入。
11.权利要求10的方法,其中在170~220℃温度下进行该挤出。
12.权利要求9的方法,其中在加入紫外光吸收剂与含至少一种式I硝酰基部分的化合物的混合物之后,使该聚氨酯组合物进行另外的加工步骤。
13.权利要求12的方法,其中该另外的加工步骤在处于或高于45℃的温度下发生。
14.权利要求12的方法,其中该另外的加工步骤包括选自下列的步骤:干燥、固化、加热、硬化、模塑、压延、捏炼、浇铸、吹塑、喷雾、压塑、共混、交联、进一步聚合、扩链、挤出、拉伸、纤维制造、染色、着色、研磨、悬浮、乳化、涂布。
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