CN1163921A - 稳定剂组合物 - Google Patents
稳定剂组合物 Download PDFInfo
- Publication number
- CN1163921A CN1163921A CN97103141A CN97103141A CN1163921A CN 1163921 A CN1163921 A CN 1163921A CN 97103141 A CN97103141 A CN 97103141A CN 97103141 A CN97103141 A CN 97103141A CN 1163921 A CN1163921 A CN 1163921A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- formula
- phenyl
- hydrogen
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003381 stabilizer Substances 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 claims abstract description 105
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 239000001301 oxygen Substances 0.000 claims abstract description 23
- 239000004753 textile Substances 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002657 fibrous material Substances 0.000 claims abstract description 15
- 239000011368 organic material Substances 0.000 claims abstract description 5
- 230000006378 damage Effects 0.000 claims abstract description 4
- -1 Phenyl Chemical group 0.000 claims description 140
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 238000004043 dyeing Methods 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 25
- 229920000728 polyester Polymers 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 238000007639 printing Methods 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 16
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229960001755 resorcinol Drugs 0.000 claims description 9
- 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 8
- 239000002841 Lewis acid Substances 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 150000007517 lewis acids Chemical class 0.000 claims description 7
- 230000006641 stabilisation Effects 0.000 claims description 5
- 238000011105 stabilization Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 239000012433 hydrogen halide Substances 0.000 claims description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 230000037072 sun protection Effects 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 32
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 19
- 229960003742 phenol Drugs 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000012964 benzotriazole Substances 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000004700 high-density polyethylene Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229940059574 pentaerithrityl Drugs 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 7
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 7
- 229920001903 high density polyethylene Polymers 0.000 description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([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])[H] 0.000 description 7
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 6
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 208000007578 phototoxic dermatitis Diseases 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
- 150000002429 hydrazines Chemical class 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920006324 polyoxymethylene Polymers 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- PMNGNPRHPYYVNM-UHFFFAOYSA-N 1-hydroxyundecane-3-sulfonic acid Chemical compound CCCCCCCCC(CCO)S(O)(=O)=O PMNGNPRHPYYVNM-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- 229920002943 EPDM rubber Polymers 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
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- 239000007795 chemical reaction product Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 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
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 229940038384 octadecane Drugs 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
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- KGUHNPYZVOXLMM-UHFFFAOYSA-N 1-(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound CC1(C)CC(C(N)CCCCCN)CC(C)(C)N1 KGUHNPYZVOXLMM-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
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- 239000004215 Carbon black (E152) Substances 0.000 description 3
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- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 3
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- 239000006096 absorbing agent Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
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- 125000002947 alkylene group Chemical group 0.000 description 3
- 229940055858 aluminum chloride anhydrous Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 229960000452 diethylstilbestrol Drugs 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229920000554 ionomer Polymers 0.000 description 3
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- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
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- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical group [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- 229940045919 sodium polymetaphosphate Drugs 0.000 description 1
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- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
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- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
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- 239000011709 vitamin E Substances 0.000 description 1
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- 238000009976 warp beam dyeing Methods 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
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- 239000002076 α-tocopherol Substances 0.000 description 1
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- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/22—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to two ring carbon atoms
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/152—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/165—Ethers
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/252—Mercaptans, thiophenols, sulfides or polysulfides, e.g. mercapto acetic acid; Sulfonium compounds
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
- D06M13/358—Triazines
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- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl groups
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65131—Compounds containing ether or acetal groups
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
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Abstract
含有至少一种式(1)所示化合物和至少一种式(2)所示化合物的稳定剂混合物,式中各基团如权利要求1限定。用于为防止有机材料尤其是纺织纤维材料受到光、氧和热的破坏作用而进行稳定化处理。
Description
本发明涉及含有单和双间苯二酚基三嗪的新型稳定剂混合物、其制备方法及其在有机材料、优选未染色或经过染色的纺织纤维材料的光化学和化学稳定化处理方面的用途。
本发明提供含有至少一种式(1)所示化合物和至少一种式(2)所示化合物的稳定剂混合物式中R1与R1’彼此独立地为直链或支链C1-18烷基、C3-8环烷基、C3-6链烯基、未取代或被取代芳基或C7-12芳烷基,R2、R2’、R3、R3’、R4和R5彼此独立地为氢、未被取代或被取代的直链或支链C1-12烷基或直链或支链C4-28烷基,它们被一个或多个N,S或O原子阻断并且可被进一步取代或者是基团-CO-R6或-SO5R6,R6为C1-12烷基、未被取代或被C1-4烷基取代的苯基或C7-12芳烷基。作为C1-18烷基的R1和R1’包括直链或支链烷基,例如甲基,乙基,正丙基或异丙基,正、异、仲或叔丁基,2-乙基丁基,正或异戊基,1-甲基戊基,1,3-二甲基丁基,正己基,1-甲基己基,正或异庚基,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,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,十七烷基或十八烷基。作为烷基的R1与R1’彼此独立地分别优选为C1-6烷基,尤其优选为C1-4烷基,更为优选的是甲基。
作为环烷基的R1与R1’包括例如未被取代或被一个或多个C1-4烷基、优选甲基取代的饱和3-8元碳环。其实例为环戊基、环己基、甲基环己基或环庚基。作为环烷基,R1与R1’优选为并且彼此独立地分别为未被取代或被1-3个甲基取代的环己基。
适宜的链烯基R1或R1’的实例为烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、2,4-戊二烯基或3-甲基-2-丁烯基。作为链烯基的R1和R1’彼此独立地分别优选为烯丙基或异丙烯基,尤其优选为烯丙基。
作为芳基的R1和R1’为例如联苯基、萘基或尤其是苯基,它们分别还可被例如C1-4烷基、C1-4烷氧基或卤素取代。作为芳基的R1与R1’彼此独立地分别优选为未被取代或被C1-4烷基取代的苯基,特别优选的分别为苯基。
适宜的芳烷基R1与R1’的实例为苄基:α-甲基苄基、苯乙基、苯丙基、苯基丁基、苯基戊基或苯基己基。作为芳烷基的R1与R1’彼此独立地分别优选为苄基或α-甲基苄基,特别优选地分别为苄基。
R1与R1’可以不同,以相同为佳。
本发明的优选实施方案涉及含有上式(1)和(2)所示化合物中至少一种的稳定剂混合物,其中R1与R1’彼此独立地分别为C1-6烷基、未被取代或被1-3个甲基取代的环己基,或者为烯丙基、异丙烯基、未被取代或被C1-4烷基、C1-4烷氧基或卤素取代的苯基、苄基或α-甲基苄基。
本发明特别优选的实施方案涉及稳定剂混合物,其中含有其中R1与R1’相同并且分别为C1-4烷基、环己基、烯丙基、苯基或苄基的上述式(1)与(2)所示化合物中至少一种。
本发明特别优选实施方案涉及由其中R1与R1’相同并且分别为C1-4烷基、尤其是甲基的式(1)和(2)所示化合物组成的稳定剂混合物。
在R2、R2’、R3、R3’、R4或R5为C1-12烷基的情况下,举例来说可以是上述R1定义中的C1-12烷基之一或例如被卤素、氰基、羟基、氨基、C1-4烷氧羰基、氨基甲酰基、N-单或N,N-二C1-4烷基氨基甲酰基、缩水甘油基或苯基取代的相应的C1-12烷基。适宜的C1-4烷氧羰基取代基的实例为甲氧羰基或乙氧羰基。缩水甘油基为2,3-环氧丙基。
作为烷基的R2,R2’,R3,R3’,R4和R5彼此独立地分别优选为C1-6烷基、尤其优选为C1-4烷基,更优选为甲基、乙基或正丙基或异丙基。
在R2、R2’、R3、R3’、R4或R5为被杂原子阻断的烷基的情况下,举例来说为被一个或多个基团-O-、-NH-或-S-阻断并且可被羟基或-OR6进一步被取代的直链或支链C4-28烷基,其中R6如上限定;在这类化合物中,杂原子基团-O-、-NH-或-S-不会彼此邻近。作为被杂原子阻断的烷基的R2、R2’、R3、R3’、R4或R5彼此独立地和优选地分别为被一个或多个基团-O-阻断并且被羟基或基团-OR6取代的直链或支链C4-28烷基。作为杂烷基的R2、R2’、R3、R3’、R4和R5彼此独立地分别优选为其中R7为氢、甲基或乙基、R8为氢、C1-12烷基或苯基以及n为整数1-9的-(CH2CHR7-O)n-R8,尤其优选为其中R7为甲基、尤其是氢以及n为整数1-9的-(CH2CHR7-O)n-H。
当R6为C1-12烷基时,例如可以是上述R1定义中C1-12烷基之一。作为烷基的R6优选为C1-4烷基,尤其优选为甲基或乙基,更优选为甲基。当R6为苯基时,优选苯基、间、邻、对甲苯基,尤其优选为苯基。当R6为芳烷基时,优选为苄基。
R2、R2’、R3、R3’、R4和R5彼此独立地分别优选为氢、C1-6烷基或直链或支链C4-28烷基,它被一个或多个基团-O-阻断并且被羟基或其中R6为C1-6烷基、苯基、邻、间、对甲苯基或苄基的基团-OR6取代,或者未被取代或被C1-4烷基取代的苯甲酰基或苯磺酰基。R2、R2’、R3、R3’、R4和R5彼此独立地分别特别优选地为氢,C1-4烷基,其中R7为甲基或尤其是氢以及n为整数1-9的式-(CH2CHR7-O)n-H所示基团,以及苯甲酰基。R2、R2’、R3、R3’、R4和R5彼此独立地分别更为优选地为氢、甲基、乙基或正或异丙基。
本发明优选的实施方案涉及含有上述式(1)与(2)所示化合物中至少一种的稳定剂混合物,其中R2、R2’和R5彼此独立地分别为C1-4烷基,其中R7为甲基或尤其是氢以及n为整数1-9的式-(CH2CHR7-O)n-H所示的基团,或苯甲酰基,R3为氢,C1-4烷基,其中R7为甲基或尤其是氢以及n=1-9的式-(CH2CHR7-O)n-H所示基团,R3’与R4分别为氢。
本发明的一个特别优选的实施方案涉及含有上述式(1)和(2)所示化合物中至少一种的稳定剂混合物,其中R2、R2’与R5相同并且分别为C1-4烷基,R3为氢或C1-4烷基,R3’与R4分别为氢。
举例来说,式(1)所示化合物可以由EP-A-0584044得知或者借助其中所述方法制备,例如通过将1摩尔当量氰尿酰氯与约1摩尔当量其中R1如上限定的R1-SH化合物缩合、随后与2摩尔当量相应的苯化合物在路易斯酸存在下反应而得到。
某些式(2)所示化合物为新型化合物。因此,本发明还提供上述式(2)所示化合物,其中R1与R1’彼此独立地分别为直链或支链C1-18烷基、C3-8环烷基、C3-6链烯基或C7-12芳烷基,R4与R5彼此独立地分别为氢,未被取代或被取代的直链或支链C1-12烷基,被一个或多个N、S或O原子阻断并且可被进一步取代的支链或直链C4-28烷基,或者为基团-COR6-或-SO2-R6,其中R6为C1-12烷基,未被取代或被C1-4烷基取代的苯基或C7-12芳烷基。
可以按照类似于式(1)所示已知化合物的制备方法获得式(2)所示化合物,例如,通过使1摩尔当量氰尿酰氯与约1摩尔当量化合物R1-SH和约1摩尔当量化合物R1’-SH反应,随后使该反应产物与约1摩尔当量相应的苯化合物在路易斯酸、优选氯化铝存在下反应来制备,其中R1与R1’如上定义,可以不同,以相同为佳。
可以由单一化合物借助已知方法制备新型稳定剂混合物,例如通过将这些化合物混合或将其放在一起研磨或其结晶来制备。还可以通过将化合物(1)与(2)同时或依次加入有待被稳定的纺织纤维基材来完成这一混合过程。
本发明还涉及对含有其中R1与R1’相同的上述式(1)与(2)所示化合物中至少一种的混合物尤其优选的共同合成法制备新型稳定剂混合物的方法,按照该制备法,通过例如下述步骤制备新型稳定剂混合物:
(i)在含水或含水-有机溶液中使氰尿酰卤例如氰尿酰氟或优选地氰尿酰氯与过量下式所示化合物在不存在或存在、若X为氢时必须存在卤化氢接受体的条件下反应
R1-S-X (3)式中X为氢或阳离子,R1如上限定,
在步骤(i)中化合物(3)与氰尿酰卤的反应由例如GB-A-1,176770可以得知或者可以类似方式完成。举例来说,该反应在-5-100℃、优选0-50℃于含水、必要时含有机溶剂例如烷基苯如甲苯或二甲苯、取代苯如氯苯、硝基苯或茴香醚或未被取代或被取代的脂族或脂环族烃如戊烷、己烷、环己烷、丁醚、二氯甲烷或氯仿的介质中进行。优选的有机溶剂为烷基苯、尤其是甲苯、邻、间或对二甲苯或不同二甲苯的混合物。步骤(i)中适宜的卤化氢接受剂的实例为碱金属或碱土金属的碳酸盐、碳酸氢盐或氢氧化物,优选为碱金属氢氧化物如氢氧化钠或钾。如果采用其中X为阳离子如碱金属、碱土金属或铵阳离子并且优选为碱金属阳离子如钾、尤其是钠阳离子的化合物(3a),则不必加入卤化氢接受剂。步骤(i)中得到的化合物(4a)与(4b)的比率取决于例如所用反应物的化学计量比例、氰尿酰卤与化合物(3),并且可以例如在95-5%(重)化合物(4a)与5-95%(重)化合物(4b)之间变化。
(i)中得到的产物与间苯二酚之间的反应通常在Friedel-Crafts反应的常规条件下,例如在10-50℃,优选25-40℃,在路易斯酸、有利地为氯化铝存在下进行。其中间苯二酚与路易斯酸分别有利地至少以等摩尔数量或优选地以相对于有待被取代的氰尿酰卤上的卤素摩尔量在一定程度上过量的数量存在。例如,间苯二酚/待取代的卤素的摩尔比和路易斯酸/待取代的卤素的摩尔比有利地分别为1∶1-2∶1,以1.1∶1-1.5∶1为佳。
该新方法的步骤(i)与(ii)可以分别进行或以一锅法反应完成。在采用一锅法的优选实施方案中,步骤(i)中得到的有机相有利地通过例如共沸蒸馏得到干燥,并且在无需进行附加提纯的条件下按照步骤(ii)进一步反应。
在视具体情况而决定是否进行的步骤(iii)中,适宜的烷基化剂的实例为其中R为烷基、Hal为卤素例如氯、溴或碘的烷基卤R-Hal,碳酸二烷基酯例如碳酸二甲酯,通式R-O-SO2-OH、R-O-SO2-O-R或R-O-SO2-C6H5-CH3所示的硫酸烷基酯或二烷基酯,其中R分别为任意一种烷基,Z为例如C1-4烷基或羟基的式R-O-P(O)(Z)-O-R所示的膦酸烷基酯或酰胺乙缩醛例如二甲基甲酰胺二甲基乙缩醛。甲基化剂的实例为硫酸二甲酯、甲苯磺酸甲酯或甲基膦酸二甲酯(DMMP)。举例来说,采用硫酸二乙酯引入乙基R2、R2’、R3’、R3、R4或R5。烷基化反应通常在例如10-200℃,优选80-150℃,在碱例如碱金属碳酸盐或碱金属氢氧化物如碳酸钠、碳酸钾或氢氧化钠存在下借助过量烷基化剂完成;该反应进行程度受到例如化学计量与反应时间影响。式(5a)与(5b)所示化合物中与成键位置成对位关系的处在三嗪环上的羟基通常比邻位的羟基容易接近,因而首先被烷基化。适宜的酰化剂的实例为其中R6如上限定并且Y为卤素、优选为氯的式R6-CO-Y或R6-SO2-Y所示化合物。
式中R1与R2分别如上定义与优选限定。特别优选的稳定剂混合物含有50-95%(重)上述式(1a)与(1b)所示化合物和50-5%(重)上述式(2a)所示化合物。
特别优选的稳定剂混合物含有50-80%(重)上述式(1a)与(1b)所示化合物和50-20%(重)上述式(2a)所示的化合物,式中R1为C1-4烷基、环己基、烯丙基、苯基或苄基,R2为C1-4烷基、其中R4为甲基或尤其是氢以及n=1-9的式-(CH2CHR4-O)n-H所示基团,或苯甲酰基,
该新型稳定剂混合物可被用作有机材料的稳定剂,尤其用于抵卸光、氧或热引起的破坏作用。这些新型化合物和稳定剂混合物特别适用作光稳定剂(紫外吸收剂)。
该新型混合物的具体优点包括对气候与光的耐受力很强和优良的光稳定性。同样值得提及的是与基质的相容性极佳。尤其是它具有突出的高亲和力。
举例来说,待稳定的材料可以是油、脂肪、蜡、化妆品或生物杀伤剂。特别令人感兴趣的是其在以塑料、橡胶、涂料、照相材料或粘合剂为存在形式的聚合材料中的用途。可以这种方式被稳定的聚合物和其它基质的实例如下所示:
1.单烯与二烯聚合物,例如聚丙烯、聚异丁烯、聚1-丁烯、聚4-甲基-1-戊烯、聚异戊二烯或聚丁二烯以及环烯烃如环戊烯或降冰片烯的聚合物;此外,聚乙烯(可视具体情况而被交联),例如高密度聚乙烯(HDPE)、高密度与高分子量聚乙烯(HDPE-HMW)、高密度与超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线型低密度聚乙烯(LLDPE)、支链低密度聚乙烯(BLDPE)。
聚烯烃,即上一段举例说明的单烯烃聚合物尤其是聚乙烯和聚丙烯可以通过不同的特别是下列方法制备:
a)通常在高压与升温条件下进行的自由基聚合
b)采用通常含有一种或多种IVb、Vb、VIb或VII族金属的催化剂进行催化聚合。这些金属通常具有一种或多种配位体如氧化物、卤化物、醇化物、酯、醚、胺、烷基、链烯基和/或芳基,它们可以π-或σ-配位。这些金属配合物可以呈游离形式或被固定在基质例如活化氯化镁、氯化钛(III)、氧化铝或氧化硅之上。这些催化剂可溶于或不溶于聚合介质。这些催化剂在聚合反应中其本身便具有活性,还可以使用活化剂例如烷基金属、金属氢化物、烷基金属卤化物、烷基金属氧化物或金属烷基噁烷,该金属为Ia、IIa和/或IIIa族元素。还可以借助例如酯、醚、胺或甲硅烷基醚基改性活化剂。这些催化剂体系通常被命名为Phillips,Standard Oil Indiana,Ziegler(-Natta),TNZ(DuPont),金属茂或单位点催化剂(SSC)。
2.1)中所述聚合物的混合物,例如聚丙烯与聚异丁烯、聚丙烯与聚乙烯(例如PP/HDPE、PP/LDPE)以及不同类聚乙烯(例如LDPE/HDPE)形成的混合物。
3.单烯和二烯烃彼此间或与其它乙烯基单体形成的共聚物;例如乙烯/丙烯共聚物、线性低密度聚乙烯(LLDPE)及其与低密度聚乙烯(LDPE)形成的混合物、丙烯/1-丁烯共聚物、丙烯/异丁烯共聚物、乙烯/1-丁烯共聚物、乙烯/己烯共聚物、乙烯/甲基戊烯共聚物、乙烯-庚烯共聚物、乙烯/辛烯共聚物、丙烯/丁二烯共聚物、异丁烯/异戊二烯共聚物、乙烯/丙烯酸烷基酯共聚物、乙烯/甲基丙烯酸烷基酯共聚物、乙烯/乙酸乙烯酯共聚物及其与CO形成的共聚物或乙烯/丙烯酸共聚物及其盐(离聚物)以及乙烯与丙烯和二烯烃如己二烯、二环戊二烯或亚乙基降冰片烯形成的三元共聚物;以及这类共聚物彼此间和与1)中所述聚合物形成的混合物,例如聚丙烯-乙烯-丙烯共聚物、LDPE-乙烯-乙酸乙烯酯共聚物、LDPE-乙烯-丙烯酸共聚物、LLDPE-乙烯-乙酸乙烯酯共聚物、LLDPE-乙烯-丙烯酸共聚物以及交替或无规聚亚烷基-一氧化碳共聚物及其与其它聚合物如聚酰胺的混合物。
4.(例如C5-9)烃树脂,包括其氢化改性形式(例如粘合剂树脂)以及聚烯与淀粉的混合物。
5.聚苯乙烯、聚(对甲苯乙烯)、聚(α-甲基苯乙烯)。
6.苯乙烯或α-甲基苯乙烯与二烯烃或丙烯酸衍生物形成的共聚物例如苯乙烯-丁二烯、苯乙烯/丙烯腈、苯乙烯-甲基丙烯酸烷基酯、苯乙烯/丁二烯/丙烯酸烷基酯、苯乙烯/丁二烯/甲基丙烯酸烷基酯、苯乙烯/马来酐、苯乙烯/丙烯腈/丙烯酸甲酯;高抗冲击强度苯乙烯共聚物与另一种聚合物例如聚丙烯酸酯、二烯烃聚合物或乙烯/丙烯/二烯烃三元共聚物以及苯乙烯的嵌段共聚物如苯乙烯/丁二烯/苯乙烯、苯乙烯/异戊二烯/苯乙烯、苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯形成的混合物。
7.苯乙烯或α-甲基苯乙烯的接枝共聚物例如苯乙烯/聚丁二烯、苯乙烯/聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物、苯乙烯和丙烯腈(或甲基丙烯腈)/聚丁二烯;苯乙烯、丙烯腈与甲基丙烯酸甲酯/聚丁二烯;苯乙烯与马来酐/聚丁二烯;苯乙烯、丙烯腈与马来酐或马来酰亚胺/聚丁二烯;苯乙烯与马来酰亚胺/聚丁二烯,苯乙烯与丙烯酸烷基酯或甲基丙烯酸烷基酯/聚丁二烯、苯乙烯与丙烯腈/乙烯-丙烯-二烯烃三元共聚物、苯乙烯与丙烯腈/聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯、苯乙烯与丙烯腈/丙烯酸酯-丁二烯共聚物、及其与6)中所述共聚物形成的混合物例如被称作ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含卤素聚合物如聚氯丁二烯、氯化橡胶、异丁烯-异戊二烯的氯化与溴化共聚物(卤丁基橡胶)、氯化或氯磺化聚乙烯、乙烯与氯化乙烯的共聚物、表氯醇均聚物与共聚物、尤其是含卤乙烯基化合物的聚合物例如聚氯乙烯、聚氟乙烯、聚偏二氯乙烯、聚偏二氟乙烯;及其共聚物如氯乙烯/1,1-二氯乙烯、氯乙烯/乙酸乙烯酯或1,1-二氯乙烯/乙酸乙烯酯。
9.由α,β-不饱和酸及其衍生物得到的聚合物如聚丙烯酸酯和聚甲基丙烯酸酯、聚甲基丙烯酸甲酯、借助丙烯酸丁酯其抗冲击强度得到提高,聚丙烯酰胺与聚丙烯腈。
10. 9)中所述单体彼此之间或与其它不饱和单体形成的共聚物例如丙烯腈-丁二烯共聚物、丙烯腈-丙烯酸烷基酯共聚物、丙烯腈-丙烯酸烷氧基烷基酯共聚物、丙烯腈-乙烯基卤共聚物或丙烯腈-甲基丙烯酸烷基酯-丁二烯三元共聚物。
11.由不饱和醇与胺或其酰基衍生物或其乙缩醛得到的聚合物如聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯或聚烯丙基蜜胺;及其与上述1中提及的烯烃形成的共聚物。
12.环醚的均聚物与共聚物如聚亚烷基二醇、聚环氧乙烷、聚环氧丙烷或其与二缩水甘油醚的共聚物。
13.聚乙缩醛如聚氧亚甲基与含有共聚单体如环氧乙烷的聚氧亚甲基;被热塑性聚氨酯、丙烯酸酯或MBS改性的聚乙缩醛。
14.聚苯氧与聚苯硫及其与苯乙烯聚合物或聚酰胺的混合物。
15.一方面由终端带有羟基的聚醚、聚酯与聚丁二烯、另一方面由脂族或芳族聚异氰酸酯衍生的聚氨酯及其前体。
16.由二胺与二羧酸和/或氨基酸或相应的内酰胺得到的聚酰胺与共聚酰胺如聚酰胺4,6,6/6,6/10,6/9,6/12,4/6,12/12,11与12,由间二甲苯、二胺与己二酸得到的芳族聚酰胺;由1,6-己二胺与间苯二酸和/或对苯二酸在有或无作为改性剂的弹性体存在下制备的聚酰胺例如聚-2,4,4-三甲基六亚甲基对苯二酰胺或聚间亚苯基间苯二酰胺。上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合的或接枝弹性体形成的嵌段共聚物;或者与聚醚、例如与聚乙二醇、聚丙二醇或聚1,4-丁二醇形成的嵌段共聚物。此外,借助EPDM或ABS改性的聚酰胺或共聚酰胺;以及加工期间被缩合的聚酰胺(RIM聚酰胺体系)。
17.聚氨酯、聚酰亚胺、聚酰胺-酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚乙内酰脲和聚苯并咪唑。
18.由二羧酸与二醇和/或羟基羧酸或相应的内酯得到的聚酯如聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚1,4-二羟甲基环己烷对苯二甲酸酯、聚羟基苯甲酸酯以及由以羟基终端的聚醚得到的嵌段聚醚酯;用聚碳酸酯或MBS改性的聚酯。
18a.酸改性的聚酯。
19.聚碳酸酯与聚酯碳酸酯。
20.聚砜、聚醚砜与聚醚酮。
21.一方面由醛、另一方面由酚、脲或蜜胺得到的交联聚合物如酚醛树脂、脲醛树脂与蜜胺-甲醛树脂。
22.干燥与非干燥的醇酸树脂。
23.由饱和与不饱和二元羧酸与多元醇的共聚酯与作为交联剂的乙烯基化合物形成的不饱和聚酯树脂及其低可燃性含卤素变体。
24.由被取代的丙烯酸酯,例如环氧丙烯酸酯、氨基甲酸乙酯丙烯酸酯或聚酯丙烯酸酯得到的可交联的丙烯酸树脂。
25.与蜜胺树脂、尿素树脂、异氰酸酯、异氰脲酸酯、聚异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂与丙烯酸树脂。
26.由脂族、脂环族、杂环或芳环缩水甘油基化合物得到的交联环氧树脂,例如借助常规固化剂如酐或胺在有或无加速剂存在下被交联的双酚A缩水甘油醚、双酚F缩水甘油醚的产物。
27.天然聚合物如木质素、天然橡胶、明胶及其以聚合物均化方式被化学改性的衍生物例如乙酸纤维素、丙酸纤维素与丁酸纤维素或纤维素醚如甲基纤维素;以及松香与衍生物。
28.上述聚合物的混合物(高聚物混体)例如PP/EPDM、聚酰胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/热塑性PU、PC/热塑性PU、POM/丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA 6.6与共聚物、PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC。
除了化合物的新型混合物以外,该新型组合物还可以含有其它稳定剂或其它添加剂如抗氧剂、其它光稳定剂、金属减活剂、亚磷酸盐或亚膦酸盐。其实例如下:
1.抗氧剂:
1.1.烷基化单酚,例如2,6-二叔丁基-4-甲酚、2-叔丁基-4,6-二甲酚、2,6-二叔丁基-4-乙酚、2,6-二叔丁基-4-正丁基酚、2,6-二叔丁基-4-异丁基酚、2,6-二环戊基-4-甲基酚、2-(α-甲基环己基)-4,6-二甲基酚、2,6-二(十八烷基)-4-甲基酚、2,4,6-三环己基酚、2,6-二叔丁基-4-甲氧基甲酚、其侧链为支链或直链的壬基酚例如2,6-二壬基-4-甲酚、2,4-二甲基-6-(1’-甲基十一烷-1’-基)酚、2,4-二甲基-6-(1’-甲基十七烷-1’-基)酚、2,4-二甲基-6-(1’-甲基十三烷-1’-基)酚及其混合物。
1.2.烷基硫代甲酚,例如2,4-二辛基硫代甲基-6-叔丁基酚、2,4-二辛基硫代甲基-6-甲酚、2,4-二辛基硫代甲基-6-乙酚、2,6-二(十二烷基)硫代甲基-4-壬基酚。
1.3.氢醌与烷基化氢醌,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、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.羟基化硫二苯醚,例如2,2’-硫二(6-叔丁基-4-甲酚)、2,2’-硫二(4-辛基苯酚)、4,4’-硫二(6-叔丁基-3-甲酚)、4.4’-硫二(6-叔丁基-2-甲酚)、4,4’-硫二(3,6-二仲戊基酚)、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-甲酚)、2,2’-亚甲基双(6-叔丁基-4-乙酚)、2,2’-亚甲基双〔4-甲基-6-(α-甲基环己基)酚〕,2,2’-亚甲基双(4-甲基-6-环己酚)、2,2’-亚甲基双(6-壬基-4-甲酚)、2,2’-亚甲基双(4,6-二叔丁基酚)、2,2’-亚乙基双(4,6-二叔丁酚)、2,2’-亚乙基双(6-叔丁基-4-异丁酚)、2,2’-亚甲基双〔6-(α-甲苯基)-4-壬基酚〕、2,2’-亚甲基双〔6-(α,α-二甲基苄基)-4-壬基酚〕、4,4’-亚甲基双(2,6-二叔丁基酚)、4,4’-亚甲基双(6-叔丁基-2-甲酚)、1,1-双(5-叔丁基-4-羟基-2-甲苯基)丁烷、2,6-双(3-叔丁基-5-甲基-2-羟基苄基)-4-甲酚、1,1,3-三(5-叔丁基-4-羟基-2-甲苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲苯基)-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-甲苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四-(5-叔丁基-4-羟基-4-甲苯基)戊烷。
1.7. O-、N-与S-苄基化合物,例如3,5,3’,5’-四叔丁基-4,4’-二羟基二苄基醚、4-羟基-3,5-二甲基苄基巯基乙酸十八烷基酯、4-羟基-3,5-二叔丁基苄基巯基乙酸十三烷基酯、三(3,5-二叔丁基-4-羟基苄基)胺、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯、双(3,5-二叔丁基-4-羟基苄基)硫醚、3,5-二叔丁基-4-羟基苄基巯基乙酸异辛酯。
1.8.羟基苄基化丙二酸酯,例如2,2-双-(3,5-二叔丁基-2-羟基苄基)丙二酸二(十八烷基)酯、2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二(十八烷基)酯、2,2-双-(3,5-二叔丁基-4-羟基苄基)丙二酸二(十二烷基巯基乙酯)、2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸二〔4-(1,1,3,3-四甲基丁基)苯酯〕。
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)-2,4,6-三甲苯、1,4-二(3,5-二叔丁基-4-羟基苄基)-2,3,5,6-四甲苯、2,4,6-三(3,5-二叔丁基-4-羟基苄基)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2,5-二叔丁基-4-羟基苄基膦酸二甲酯、3,5-二叔丁基-4-羟基苄基膦酸二乙酯、3,5-二叔丁基-4-羟基苄基膦酸二(十八烷基)酯、5-叔丁基-4-羟基-3-甲基苄基膦酸二(十八烷基)酯、3,5-二叔丁基-4-羟基苄基膦酸的单乙酯的钙盐。
1.12.酰胺基酚,例如4-羟基N-硬脂酰苯胺、4-羟基-N-月桂基酰苯胺、N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13.β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元醇或多元醇形成的酯,例如甲醇、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)异氰脲酸酯、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-2,6,7-三氧双环〔2,2,2〕辛烷。
1.14.β-(5-叔丁基-4-羟基-3-甲苯基)丙酸与一元或多元醇形成的酯,例如甲醇、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)异氰脲酸酯、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-2,6,7-三氧双环〔2,2,2〕辛烷。
1.15β-(3,5-二环己基-4-羟基苯基)丙酸与一元或多元醇形成的酯,例如甲醇、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)异氰脲酸酯、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-2,6,7-三氧双环〔2,2,2〕辛烷。
1.16 3,5-二叔丁基-4-羟基苯基乙酸与一元或多元醇形成的酯,例如甲醇、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)异氰脲酸酯、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-2,6,7-三氧双环〔2,2,2〕辛烷。
1.17β-(3,5-二叔丁基-4-羟苯基)丙酸的酰胺,例如N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰)-1,6-己二酰胺、N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰)-1,3-丙二酰胺、N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰)肼、N,N’-二〔2-(3-〔3,5-二叔丁基-4-羟基苯基〕丙酸基)乙基〕草酰胺(Uniroyal NaugardXL-1)。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧剂,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-异丙基-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-叔丁基苯基)-1-萘胺、N-苯基-2-苯胺、辛基化二苯胺,例如对,对一二叔辛基二苯胺,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、4-十八酰氨基苯酚、二(4-甲氧苯基)胺、2,6-二叔丁基-4-二甲胺基甲酚、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-甲苯基)氨基〕乙烷、1,2-二(苯胺基)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-萘基胺、一和二烷基化叔丁基/叔辛基二苯胺的混合物、一和二烷基化壬基二苯胺的混合物、一和二烷基化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、单和二烷基化叔丁基/叔辛基吩噻嗪的混合物、单和二烷基化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)-1,6-己二胺、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.紫外光吸收剂与光稳定剂
2.1.2-(2’-羟基苯基)苯并三唑例如2-(2’-羟基-5’-甲苯在)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)苯并三唑、2-(5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5‘-甲苯基)-5-氯苯并三唑、2-(3’-仲丁基-5’-叔丁基-2’-羟苯基)苯并三唑、2-(2’-羟基-4’-辛氧基苯基)苯并三唑、2-(3’,5’-二叔戊基-2’-羟苯基)苯并三唑、2-(3’,5’-二(α,α-二甲基苄基)-2’-羟基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-5’-〔2-(2-乙基己氧基)羰基乙基〕-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧羰基乙基)苯基)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)苯并三唑、2-(3’-十二烷基-2’-羟基-5’-甲苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧羰基乙基)苯基苯并三唑、2,2’-亚甲基-二〔4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚〕;2-〔3’-叔丁基-5’-(2-甲氧羰基乙基)-2’-羟基苯基〕-2H-苯并三唑与聚乙二醇300的酯基转移反应产物;〔R-CH2CH2-COO-CH2CH22,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-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〕苯并三唑;2-〔2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)苯基〕苯并三唑。
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’-三羟基与2’-羟基-4,4’-二甲氧基衍生物。
2.3.被取代与未被取代苯甲酸的酯例如水杨酸4-叔丁基苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰基间苯二酚、二(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、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-甲酯基肉桂酸甲酯、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-甲酯基对甲氧基肉桂酸甲酯与N-(β-甲酯基-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〕的镍配合物如1∶1或1∶2配合物,带有或不带有其它配位体如正丁胺、三乙醇胺或N-环己基二乙醇胺、二丁基二硫代氨基甲酸镍,4-羟基-3,5-二叔丁基苄基膦酸的单烷基酯例如甲或乙酯的镍盐,酮肟如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物、1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,带有或不带有其它配位体。
2.6.立体位阻胺例如癸二酸二(2,2,6,6-四甲基-4-哌啶基)酯、琥珀酸二(2,2,6,6-四甲基-4-哌啶基)酯、癸二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯、癸二酸二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)酯、正丁基-3,5-二叔丁基-4-羟基苄基丙二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩合物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺与4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的直链或环状缩合物、次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基)酯、1,2,3,4-丁烷四甲酸四(2,2,6,6-四甲基-4-哌啶基)酯、1,1’-(1,2-乙二基)二(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-十八烷氧基-2,2,6,6-四甲基哌啶、2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸二(1,2,6,6-五甲基哌啶基)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、癸二酸二(1-辛氧基-2,2,6,6-四甲基哌啶基)酯、琥珀酸二(1-辛氧基-2,2,6,6-四甲基哌啶基)酯、N,N’-二(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺与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-正丁胺基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪与1,2-二(3-氨基丙氨基)乙烷的缩合物、2-氯-4,6-二(4-正丁胺基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪与1,2-二(3-氨基丙氨基)乙烷的缩合物、8-乙酰-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、4-十六烷氧基与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)-1,6-己二胺与4-环己胺基-2,6-二氯-1,3,5-三嗪的缩合产物、1,2-二(3-氨基丙胺基)乙烷与2,4,6-三氯-1,3,5-三嗪以及4-丁胺基-2,2,6,6-四甲基哌啶的缩合物(CAS Reg.No.[136504-96-6]);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〕癸烷与表氯醇的反应产物、1,1-二(1,2,2,6,6-五甲基-4-哌啶氧羰基)-2-(4-甲氧苯基)乙烯、N,N’-二甲酰-N,N’-二(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺、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。
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’-二叔丁基-N,N’-草酰二苯胺、2,2’-二(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(3-二甲胺基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙基-N,N’-草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁基-N,N’-草酰二苯胺的混合物、邻与对甲氧基二取代N,N’-草酰二苯胺的混合物以及邻与对乙氧基二取代N,N’-草酰二苯胺的混合物。
2.8.2-(2-羟苯基)-1,3,5-三嗪例如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-(2,4-二羟苯基)-4,6-二(2,4-二甲苯基)-1,3,5-三嗪、2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-二(2,4-二甲苯基)-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/十三烷氧基-2-羟丙氧基)-2-羟基苯基〕-4,6-二(2,4-二甲苯基)-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(2,4-二甲苯基)-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-羟苯基)-4-(4-甲氧苯基)-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(2,4-二甲苯基)-1,3,5-三嗪。
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-1,2,4-三唑、二(亚苄基)草酰二肼、N,N’-草酰二苯胺、间苯二酰二肼、癸二酰二苯基二酰肼、N,N’-二乙酰基己二酰二肼、N,N’-二(水杨酰)草酰二肼、N,N’-二(水杨酰)硫代丙酰二肼。
4.亚膦酸酯与亚磷酸酯例如亚磷酸三苯酯、亚磷酸二苯酯烷基酯、亚磷酸苯酯二烷基酯、亚磷酸三(壬基苯酯)、亚磷酸三月桂酯、亚磷酸三(十八烷基酯)、二亚磷酸二(十八烷基酯)季戊四醇酯、亚磷酸三(2,4-二叔丁基苯酯)、二亚磷酸二异癸酯季戊四醇酯、二亚磷酸二(2,4-二叔丁基苯酯)季戊四醇酯、二亚磷酸二(2,6-二叔丁基-4-甲苯酯)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-甲苯酯)季戊四醇酯、二亚磷酸二(2,4,6-三(叔丁基苯酯)季戊四醇酯、三亚磷酸三(十八烷酯)山梨醇酯、4,4’-二亚苯基二亚膦酸四(2,4-二叔丁基苯酯)、6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并〔d,g〕-1,3,2-二氧杂磷辛英、6-氟-2,4,8,10-四叔丁基-12-甲基二苯并〔d,g〕-1,3,2-二氧杂磷辛英、亚磷酸二(2,4-二叔丁基-6-甲苯酯)甲酯、亚磷酸二(2,4-二叔丁基-6-甲苯酯)乙酯、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〕、亚磷酸2-乙基己酯(3,3’,5’,5’-四叔丁基-1,1’-联苯-2,2’-二酯)。
特别优选的是下列亚磷酸盐:
亚磷酸三(2,4-二叔丁基苯酯)(Irgafos168,CibaGeigy)、亚磷酸三(壬基苯酯),
5.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、由氢化脂胺衍生的N,N-二烷基羟基胺。
6.硝酸灵如N-苄基-α-苯基硝酸灵、N-乙基-α-甲基硝酸灵、N-辛基-α-庚基硝酸灵、N-月桂基-α-十一烷基硝酸灵、N-十四烷基-α-十三烷基硝酸灵、N-十六烷基-α-十五烷基硝酸灵、N-十八烷基-α-十七烷基硝酸灵、N-十六烷基-α-十七烷基硝酸灵、N-十八烷基-α-十五烷基硝酸灵、N-十七烷基-α-十七烷基硝酸灵、N-十八烷基-α-十六烷基硝酸灵、由氢化脂胺生成的N,N-二烷基羟基胺得到的硝酸灵。
7.硫代协合剂如硫代二丙酸二月桂酯或硫代二丙酸二硬脂基酯。
8.过氧化物清除剂如β-硫代二丙酸酯如月桂基酯、硬脂基酯、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、四(β-十二烷基巯基)丙酸季戊四醇酯。
9.聚酰胺稳定剂例如与碘化物和/或含磷化合物组合在一起的铜盐以及二价锰盐。
10.碱性共稳定剂例如蜜胺、聚乙烯基吡咯烷酮、双氰胺、氰脲酸三烯丙酯、脲衍生物、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、山萮酸镁、硬脂酸镁、蓖麻醇酸钠和棕榈酸钾、儿茶酸锑或儿茶酸锌。
11.成核剂例如无机物如滑石、金属氧化物如二氧化钛或氧化镁、优选碱土金属的磷酸盐、碳酸盐或硫酸盐;有机化合物如单或多羧酸及其盐例如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;高分子化合物如离子型共聚物(离聚物)。
12.填料与补强剂例如碳酸钙,硅酸盐、玻璃纤维、玻璃球、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物与氢氧化物、炭黑、石墨、木粉和其它天然产物的粉末或纤维、合成纤维。
13.其它添加剂如增塑剂、润滑剂、乳化剂、颜料、流变添加剂、催化剂、流动性控制剂、荧光增白剂、阻燃剂、抗静电剂与发泡剂。
14.苯并呋喃酮与二氢吲哚酮如在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中所述的物质,或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’-二〔5,7-二叔丁基-3-(4-〔2-羟乙氧基〕苯基)苯并呋喃-2-酮〕,5,7-二叔丁基-3-(4-乙氧苯基)苯并呋喃-2-酮、3-(4-乙酸基-3,5-二甲苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰氧苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(3,4-二甲苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(2,3-二甲苯基)-5,7-二叔丁基苯并呋喃-2-酮。
本发明提供的新型稳定剂混合物特别适用于未经染色、经过染色,或印染的纺织纤维材料的光化学与热稳定化处理。该处理方法包括用含有至少一种上述式(1)所示化合物与至少一种上述式(2)所示化合物的稳定剂混合物处理纺织纤维材料。
适用于处理的纺织纤维主要为含聚酯或乙酸纤维素的纤维材料。聚酯纤维一词应该被理解为例如纤维素酯纤维如二乙酸纤维素纤维和三乙酸纤维素纤维以及尤其是可被酸改性的线性聚酯纤维,这类纤维可以例如通过对苯二酸与乙二醇或者间苯二酸或对苯二酸与1,4-二(羟甲基)环己烷缩合而成,还可以是对苯二酸和间苯二酸与乙二醇的共聚物。纺织纤维工业中的常规聚酯纤维尤其是由对苯二酸与乙二醇组成的。
待处理的纺织纤维材料还可以是聚酯纤维与其它纤维的混纺织物,其实例为聚丙烯腈/聚酯、聚酰胺/聚酯、聚酯/棉、聚酯/粘胶纤维或聚酯/羊毛纤维的混纺纱,它们以常规的间歇或连续方式被印染或染色。
该纺织纤维材料可以呈多种成品形式例如布匹如针织物或机织物或如筒子纱、轴经纱等。
同样非常适用于本发明方法的还有在至少部分透光性的用于服装的织物。这种纺织物按照该新方法被处理后,能够保护服装下的皮肤组织不受紫外辐射的损害。事实上,这表明经过新型稳定剂或稳定剂混合物处理的纺织纤维材料与未经处理的织物相比在防晒因子(UPF=紫外线防护因子)方面得到显著提高。
UPF被限定为在未采用防晒措施条件下紫外辐射的有害剂量与采取防晒措施条件下紫外辐射的有害剂量之比。因此,UPF还是对未经处理的纤维材料与经过新型化合物或其混合物处理的纤维材料的紫外辐射透射率的度量。举例来说,在WO94/04515或化妆品化学会志40,127-133页(1989)中解释了防织纤维材料的UPF的确定方法。本文以类似方式实施了该方法。
新型稳定剂混合物的用量基于纤维材料的重量计例如为0.01-10%(重)、优选0.1-5%(重)。
新型稳定剂混合物的水溶性较低,因而以分散形式被使用。为此,按照应用条件采用例如适宜的分散剂并且借助例如石英颗粒与高速搅拌器将其研磨。
适宜的稳定剂混合物的分散剂的实例为:-酸性酯或其烯化氧加合物的盐类例如4-40摩尔环氧乙烷与1摩尔苯酚的加聚物的酸性酯或其盐、或6-30摩尔环氧乙烷与1摩尔4-壬基酚、1摩尔二壬基酚或者尤其是与1摩尔通过将1-3摩尔被取代或未被取代苯乙烯加至1摩尔酚中制成的化合物形成的加合物的磷酸酯,
-聚苯乙烯磺酸酯,
-脂肪酸taurides,
-烷基化二苯醚单或二磺酸酯,
-聚羧酸酯的磺酸盐,
-由1-60、优选2-30摩尔环氧乙烷和/或环氧丙烷与分别含8-22个碳原子的脂肪胺、脂肪酰胺、脂肪酸或脂肪醇或者与C3-6三元至六元链烷醇形成的加合物,该加合物采用有机二羧酸或无机多元酸被转化为酸性酯,
-木素磺酸酯,尤其是
-甲醛缩合物例如木素磺酸酯和/或酚与甲醛的缩合物、甲醛与芳族磺酸的缩合物如二甲苯醚磺酸酯与甲醛的缩合物、萘磺酸和/或萘酚或萘胺磺酸与甲醛的缩合物、酚磺酸和/或磺化二羟基二苯砜以及酚和/或甲酚与甲醛和/或脲的缩合物、以及二苯醚二磺酸衍生物与甲醛的缩合物。
当待稳定纺织纤维材料优选为经过染色的纺织纤维材料时,特别适宜的染料为水溶性低的分散染料。因此,它们在大多数情况下以细分散形式存在于染液之中。它们属于不同的染料例如偶氮、蒽醌、吖啶酮、香豆素、次甲基、萘醌亚胺、perinone,quinophthalone、苯乙烯或硝基染料。同样可以按照本发明使用分散染料混合物。
染色过程通过连续或间歇步骤在水溶液中进行。在间歇法(浸染)的情况下,浴比选择范围较宽例如1∶1-10∶10以1∶6-1∶50为佳。染色进行的温度至少为50℃、通常不大于140℃。优选为80-135℃。
在连续法的情况下,其中除了染料外还可以包含助剂的染液可以借助例如初染、喷涂或knit-padding被施用于匹材并且通过热固着或高温蒸汽方法显色。
优选通过高温法在密闭耐压设备中于>100℃,优选110-135℃在大气压或超大气压下染色线型聚酯纤维与纤维素纤维。适宜的密闭容器的实例为循环设备如筒子纱或经轴染色设备、绞盘染槽、喷射或转筒染色机、袖笼绞纱染色设备、搅拌器或卷染机。
二乙酸纤维素纤维优选在80-85℃下被染色。
当该新型稳定剂混合物被用于染色时,优选地,首先用这些稳定剂混合物处理纤维材料随后进行染色或者优选地,同时利用稳定剂混合物与染浴中的染料处理纤维材料。然而,还可以随后将稳定剂混合物通过例如在190-230℃热固着30秒-5分钟施用于成品染色。同样可以用新型稳定剂混合物预处理纺织材料,与此同时该纺织材料的尺寸稳定不变。
染液中还含有其它添加剂,其实例为染色助剂、分散剂、载体、羊毛保护剂、润湿剂与消泡剂。
染浴中还含有无机酸,其实例为硫酸或磷酸或更适宜地含有有机酸例如脂族羧酸如甲酸、乙酸、草酸或柠檬酸和/或盐如乙酸铵、硫酸铵或乙酸钠。具体地,酸的用途是按照本发明控制溶液的pH,其值以4-5为佳。
含有染料、稳定剂混合物以及必要时存在的其它添加剂并且其pH由4.5被调至5.5的染浴优选地于初始时刻与纤维材料在40-80℃被放入处理过程,历时5分钟,随后将温度升至125-130℃,历时10-20分钟,在此温度下继续处理15-90分钟,优选30分钟。
通过将染液冷却至50-80℃,用水清洗以及必要时在碱性介质中以常规方式进行还原清洗来后处理染色。随后再次清洗干燥。在还原染料被用于纤维素部分时,成品织物通常首先用亚硫酸氢盐在pH=6-12.5的条件下随后用氧化剂进行处理,最后进行清洗。
为了印花,将新型稳定剂混合物以其水分散体形式加至印花浆中。印花浆含有适宜的例如基于印花浆重量计0.1-10%、优选0.1-5%稳定剂混合物。
被加至印花浆中的染料量取决于所需的色泽;业已发现适宜的用量以纺织材料用量为基准计通常为0.01-15%(重)、优选0.02-10%(重)。
除了染料与含水稳定剂混合物分散体以外,印花浆有利地还含有优选天然的酸稳定增稠剂。如玉米粉衍生物,尤其是藻酸钠自身或与改性纤维素、具体地与优选20-25%(重)羧甲基纤维素形成的混合物。此外,印花浆还可以含有酸给体如丁内酯或磷酸氢钠、防腐剂、多价螯合剂、乳化剂、水不溶性溶剂、氧化剂或脱气剂。
特别适用的防腐剂为甲醛给体如仲甲醛或三噁烷、尤其是浓度为约30-40%(重)的甲醛水溶液;适宜的多价螯合剂的实例为次氮基三乙酸钠、乙二胺四乙酸钠、尤其是聚偏磷酸钠、尤其是六聚偏磷酸钠;特别适用的乳化剂为烯化氧与脂肪醇的加合物、尤其是油醇与环氧乙烷的加合物;适宜的水不溶性溶剂为高沸点饱和烃,尤其是沸程为约160-210℃的链烷(溶剂石脑油);适宜的氧化剂的实例为芳族硝基化合物、尤其是芳族单或二硝基羧酸或磺酸,它们可以呈烯化氧加合物的形式,尤其是硝基苯磺酸;适宜的脱气剂的实例为高沸点溶剂,尤其是松节油、高级醇、优选C8-10醇、萜烯醇或基于矿物油和/或硅油的脱气剂,尤其是由约15-25%(重)矿物油与硅油混合物和约75-85%(重)C8醇如2-乙基正己醇组成的市售配方。
在纤维材料的印花过程中,印花浆被直接施用在纤维的全部区域或截面上,有利地采用常规构造的印染机例如注墨印花,毛条印花、凹纹印花、圆网印花或平版印花机。
印花之后,在高达150℃,优选80-120℃下干燥纤维材料。
随后通过优选在100-220℃下进行热处理来稳定化处理该材料。通常采用过热蒸汽于加压下进行热处理。
该稳定化处理依据温度而定历时20秒-10分钟,优选4-8分钟。
以类似于常规方式通过水清洗后处理印花,必要时,通过在碱性介质中例如采用连二亚硫酸钠进行附加的还原清洗进行后处理。在后一种情况下,印花再次被清洗、脱水与干燥。
用新型稳定剂混合物处理过的纺织纤维对光、氧与热的破坏效果具有良好的耐受力。具体地,可以使用新方法获得高度耐晒并且抗升华的聚酯染色与印花。采用新方法不必再进行特殊的纤维材料预处理或后处理。
下列实施例中,百分数为重量百分比。染料与紫外线吸收剂的量基于纯物质。
实施例1
在搅拌下将984g冰导入541.4g氰尿酰氯在1327g二甲苯(异构体混合物)中的混合物。随后边搅拌边加入1130g 21%甲基硫醇钠水溶液,历时10分钟,在此期间,温度升至约30℃。继续搅拌1小时。相分离后,分出下部水相。用885g水洗有机相一次,得到2044g含18%(重)1-甲硫基-3,5-二氯-S-三嗪与7.1%(重)1,3-二甲硫基-5-氯-S-三嗪的二甲苯溶液。
实施例2
于25℃和搅拌下将63.71g无水氯化铝加入200g实施例1获得的含36g 1-甲硫基-3,5-二氯-S-三嗪与14.2g 1,3-二甲硫基-5-氯-S-三嗪的二甲苯溶液中。搅拌15分钟。随后滴加52.64g间苯二酚于110g四氢噻吩砜中的溶液1.5小时。在此期间,将反应温度由45℃升至约50℃。最后,通过在70℃再搅拌1.5小时以及接着在80℃搅拌1小时来完成缩合反应。将乳液状混合物冷却至50℃并且通过谨慎滴加由62g 32%盐酸与455g水组成的混合物水解Friedel-Craft配合物。通过共沸蒸馏脱除二甲苯并且用抽吸过滤产物悬浮液。用热水清洗过滤材料并且在80℃进行减压干燥,得到78.1g含重量比为A∶B=15∶85的下式所示化合物的粉末。
实施例3
将60ml 2N氢氧化钠溶液滴加至20g实施例2中获得的产物混合物于180ml甲乙酮中形成的悬浮液中。随后在33-35℃经过1小时将13.99g硫酸二甲酯滴加至该混合物中。搅拌16小时后,用2N盐酸中和产物混合物。通过共沸蒸馏分离有机溶剂,最后经过滤分离得到结晶产物。水洗滤器残渣并且在70℃进行减压干燥,得到含有下式C、D与E所示化合物的粉末,其重量比为71∶13∶16。
实施例4
重复实施例3的步骤,不同的是使用17.88g硫酸二乙酯而不是13.99g硫酸二甲酯,反应温度被保持在40℃;得到的产物混合物主要含有下式所示化合物
实施例5
将15.4g甲基硫醇钠的21%水溶液于80℃在1小时期间滴加至28,7g1-甲硫基-3,5-二氯-S-三嗪(如GB-A-1176770的实施例1中制备)的甲苯溶液中。随后加入50ml水并且随后在90-95℃再搅拌一小时。冷却至室温,加入冰/冰水与100ml 1N氢氧化钠溶液。短时间搅拌后,分离有机相,再次水洗并且用氯化钙干燥。
将14.7g无水氯化铝导入121.5g所得到的含17.1g(重)1,3-二甲硫基-5-氯-S-三嗪的甲苯溶液中。随后在25分钟内于45-50℃下滴加12.1g间苯二酚的25ml四氢噻吩砜溶液。于75℃下搅拌3小时。将乳液冷却至约60℃并且用15ml浓盐酸与200ml水的混合物仔细分解Friedel-Craft配合物。经共沸蒸馏分离出甲苯并且抽吸过滤产物悬浮液。用热水洗涤并且压挤残渣。粗产物自水/二噁烷中重结晶后得到粉状下式所示化合物
实施例6
将3.37g碳酸钠加至8.43g实施例5的化合物于27.9g甲基膦酸二甲酯中的悬浮液中,于120℃加热2 3/4小时。冷却至75-80℃,滴加70ml甲醇与20ml水的混合物。冷却至室温后,吸滤固体沉淀,用少量甲醇洗涤,最后用热水洗涤。于70℃减压干燥并且自石油醚/二噁烷中重结晶提纯,得到白色粉状下式所示化合物
实施例7
边搅拌边将250g冰导入92.9g氰尿酰氯与400ml甲苯的混合物中。随后边搅拌边在约1.5小时内滴加61.9g乙硫醇钠的250ml水溶液,在此期间将温度逐渐升至约30℃。于约48℃继续搅拌15分钟。冷却后,产生相分离。分离水相,用500ml水洗有机相三次,用氯化钙干燥后得到590.9g含11.5%(重)1-乙硫基-3,5-二氯-S-三嗪与3.48%(重)1,3-二乙硫基-5-氯-S-三嗪的甲苯溶液。
实施例8
边搅拌边在室温下将95.8g无水氯化铝(III)加入564.5g实施例7的甲苯溶液,温和加热后产生红色溶液。继续加热至40℃,在1.5小时内滴加79.2g间苯二酚的165ml四氢噻吩砜溶液。在此期间,温度被升至57℃。随后在80℃搅拌4小时。冷却至约50℃,将反应物料倾入1000g冰/250ml水。随后共沸蒸馏脱除甲苯,过滤产物的水悬浮液。用热水与冷水洗残渣直至得到中性反应刚果红为止。于80℃减压干燥,得到133.7g含重量比为A’∶B’=24∶76的下式所示化合物的亮黄色粉末。
实施例9
将91.8ml 2N氢氧化钠溶液滴加至20g实施例8的产物与100ml水的混合物中,在此期间,温度被保持在20℃。随后在1.5小时内滴加18.5g硫酸二甲酯,在此期间通过同时滴加2N氢氧化钠溶液将反应混合物的pH保持在11。于室温下搅拌21小时,并且过滤。再次将残余物悬浮于水中并且用稀盐酸中和。再次过滤后,水洗残渣并在70℃减压干燥,得到含有重量比C’∶D’=22∶78的下式所示化合物的米色粉末。
染色实施例
(I)制备稳定剂配方:
将10g实施例3获得的稳定剂混合物,20ml 10%三苯乙烯基苯基-聚乙二醇-磷酸的三乙醇胺盐水溶液和25g石英珠(粒径为1mm)放入高速搅拌器中并且研磨16小时。随后将研磨物料通过一细目筛以便脱除玻璃珠,边搅拌边加入0.5g合成生物聚合胶(例如BiopolymerAG),用水调整配方以便使稳定剂含量达10%(重)。分散体的粒度约为0.5-2μm。
(ii)用于浸染法:
在高温(HT)染色机(例如Turbomat,Mathis,Nieblerhasli)中以10∶1的浴比染色10g聚酯特里科经编织物样品。含水染液含2g/l硫酸铵,0.5g/l助染剂(Univadin3-flex)、以聚酯特里科经编织物重量为基准的0.5%(重)于(i)中制备的紫外光吸收剂配方和0.89%(重)含下列化合物的染料混合物
用乙酸将染液的pH调至5,均化后与特里科经编织物一道放入高压染色罐中。于70℃开始染色,在10分钟内加热至100℃,在20分钟内加热至130℃,在此温度染色30分钟后,冷却至50℃,经过热清洗与冷清洗,用含3ml 30%氢氧化钠溶液和2g/l连二亚硫酸钠溶液在70℃进行还原清洗。清洗后干燥后得到呈灰紫色并且具备非常良好的耐热光性的聚酯特里科经编织物。
(iii)重复(ii)所述步骤,不同的是用不含(i)制备的稳定剂配方的染液进行聚酯特里科经编织物的染色,染色后的耐热光性很低。
(iv)重复(ii)的步骤,不同的是用以聚酯特里科经编织物为基准计含1.15%(重)组成如下的染料混合物进行染色:分别为13%(重)的染料F1与F2、38.1%(重)染料F3、25.4%(重)染料F4、4.4%(重)染料F5、3.2%(重)染料F6和2.9%(重)染料F7。得到酒红色具备非常良好的耐热光性的聚酯特里科经编织物。
(v)重复步骤(iv),不同的是用不含(i)中制备的稳定剂配方的染液染色聚酯特里科经编织物,得到的染色的耐热光性很低。
印花实施例:
由原浆、染料与稳定剂混合物制备用于聚酯花式特里科经编织物印花工艺的印花浆。
原浆的组成如下:
120g淀粉醚增厚剂
480g藻酸钠增稠剂
5g磷酸氢钠
5g印花助剂
5g氯酸钠
385g去离子水
1000g原浆
印花浆料组成如下:
3.6g染色实施例中的染料F2
34g含有染色实施例中的染料F3与下式所示染料的染料混合物
0.4g染色实施例中的染料F7
1.6g染色实施例中的染料F6
60g作为20%研磨配方的实施例3中的稳定剂混合物
931g原浆。
该印花浆被用于在印花台板上印花聚酯特里科经编织物的净布。在100℃干燥10分钟后,用过热蒸汽在180℃处理8分钟。经过印花的织物被热清洗与冷清洗,于70℃采用含2ml/l 30%氢氧化钠溶液与3g/l连二亚硫酸钠的溶液还原清洗。清洗与干燥后得到带浅红色印花并且具有非常好的耐热光性的聚酯特里科经编织物。
若采用不含该稳定剂混合物的印花浆料重复上述步骤,则染色后的耐热光性要低得多。
Claims (19)
1.含有至少一种式(1)所示化合物和至少一种式(2)所示化合 式中R1与R1’彼此独立地为直链或支链C1-18烷基、C3-8环烷基、C3-6链烯基、未取代或被取代芳基或C7-12芳烷基,R2、R2’、R3、R3’、R4和R5彼此独立地为氢、未被取代或被取代的直链或支链C1-12烷基或直链或支链C4-28烷基,它们被一个或多个N,S或O原子阻断并且可被进一步取代或者是基团-CO-R6或-SO5R6,R6为C1-12烷基、未被取代或被C1-4烷基取代的苯基或C7-12芳烷基。
2.按照权利要求1的稳定剂混合物,其中R1与R1’彼此独立地分别为C1-6烷基、未被取代或被1-3个甲基取代的环己基,烯丙基、异丙烯基、未被取代或被C1-4烷基、C1-4烷氧基或卤素取代的苯基、苄基或α-甲基苄基。
3.按照权利要求1或2的稳定剂混合物,其中R1与R1’相同并且分别为C1-4烷基、环己基、烯丙基、苯基或苄基。
4.按照权利要求1的稳定剂混合物,其中R1与R1’相同并且分别为C1-4烷基、尤其是甲基。
5.根据权利要求1-4中任一项的稳定剂混合物,其中R2、R2’、R3、R3’、R4和R5彼此独立地分别为氢、C1-6烷基或直链或支链C4-28烷基,它被一个或多个基团-O-阻断并且被羟基或其中R6为C1-6烷基、苯基、邻、间、对甲苯基或苄基的基团-OR6取代,或者未被取代或被C1-4烷基取代的苯甲酰基或苯磺酰基。
6.根据权利要求1-5中任一项的稳定剂混合物,其中R2、R2’、R3、R3’、R4和R5彼此独立地分别为氢,C1-4烷基,其中R7为甲基或尤其是氢以及n为整数1-9的式-(CH2CHR7-O)n-H所示基团,或苯甲酰基。
7.根据权利要求1-6中任一项的稳定剂混合物,其中R2、R2’和R5彼此独立地分别为C1-4烷基,其中R7为甲基或尤其是氢以及n为整数1-9的式-(CH2CHR7-O)n-H所示的基团,或苯甲酰基,R3为氢,C1-4烷基,其中R7为甲基或尤其是氢以及n=1-9的式-(CH2CHR7-O)n-H所示基团,或苯甲酰基,R3’与R4分别为氢。
8.根据权利要求1-7中任一项的稳定剂混合物,其中R2、R2’与R5相同并且分别为C1-4烷基,R3为氢或C1-4烷基,R3’与R4分别为氢。
9.根据权利要求1的稳定剂混合物,其中主要含有其中R1与R2分别如权利要求1限定的下式所示化合物:
10.根据权利要求9的稳定剂混合物,其中含有50-95%(重)式(1a)与(1b)所示化合物和50-5%(重)式(2a)所示化合物。
11.根据权利要求9的稳定剂混合物,其中含有50-80%(重)式(1a)与(1b)所示化合物和50-20%(重)式(2a)所示的化合物,式中R1为C1-4烷基、环己基、烯丙基、苯基或苄基,R2为C1-4烷基、其中R4为甲基或尤其是氢以及n=1-9的式-(CH2CHR4-O)n-H的基团,或苯甲酰基。
13.一种为防止有机材料受到光、氧和/或热的破坏作用而进行稳定化处理的方法,其中包括向其中加入在每一种情况下含有至少一种权利要求1中指明的式(1)与式(2)所式化合物的稳定剂混合物。
14.用于为防止有机材料受到光、氧和热的破坏作用而进行稳定化处理的在每一情况下含有至少一种权利要求1所述式(1)与式(2)化合物的稳定剂混合物的用途。
15.对未经染色、经过染色或印染的纺织纤维材料进行光化学与热稳定化处理方法,其中包括用在每一种情况下含有至少一种权利要求1所述式(1)与式(2)所示化合物的稳定剂混合物处理纺织纤维材料。
16.按照权利要求15的方法,其中包括对未经染色、经过染色或经过印染的聚酯纤维材料进行光化学与热稳定化处理。
17.一种提高未经染色、经过染色或印染的纺织纤维料的防晒因子(UPF)的方法,其中包括用在每种情况下含有至少一种权利要求1指明的化合物(1)和(2)的稳定剂混合物处理纺织纤维材料。
18.在每一种情况下含有至少一种权利要求1中指明的化合物(1)与(2)的稳定剂混合物在对未经染色、经过染色或印染的纺织纤维材料进行光化与热稳定化处理方面的用途。
19.按照权利要求1的式(2)所示化合物,其中R1与R1’彼此独立地分别为直链或直链C1-18烷基、C3-8环烷基、C3-6链烯基或C7-12芳烷基,R4与R5彼此独立地分别为氢,未被取代或被取代的直链或支链C1-12烷基,被一个或多个N、S或O原子阻断并且可被进一步取代的支链或直链C4-28烷基,或者为基团-COR6-或-SO2-R6,其中R6为C1-12烷基,未被取代或被C1-4烷基取代的苯基或C7-12芳烷基。
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JP5228395B2 (ja) * | 2007-08-09 | 2013-07-03 | Dic株式会社 | 合成繊維起毛布用着色剤及び抜染剤、並びにそれらを用いた加工方法及びその方法により加工した合成繊維起毛布 |
JP5675647B2 (ja) | 2009-01-19 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 有機黒色顔料およびその製造 |
CN104003952B (zh) * | 2013-12-13 | 2016-09-28 | 保定市乐凯化学有限公司 | 4-[(4,6-二辛硫基-1,3,5-三嗪-2-基)氨基]-2,6-二叔丁基苯酚的制备方法 |
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NL302946A (zh) * | 1963-01-24 | |||
CH388253A (de) * | 1963-01-24 | 1965-06-15 | Geigy Ag J R | Verfahren zum Schützen von Textilmaterial gegen Lichtschädigung |
GB1114861A (en) * | 1964-05-04 | 1968-05-22 | Ciba Ltd | New hydroxyphenyl-triazines and process for their manufacture |
CH473604A (de) * | 1965-02-19 | 1969-06-15 | Ciba Geigy | Verwendung von neuen Aryl-1,3,5-triazinen als Stabilisierungsmittel für nicht-textile organische Materialien |
US3334046A (en) * | 1965-07-20 | 1967-08-01 | Geigy Chem Corp | Compositions stabilized with substituted 1, 3, 5-triazines |
DE1670101A1 (de) * | 1966-07-02 | 1970-12-03 | Basf Ag | Verfahren zur Herstellung von 1,3,5-Triazinen |
DE1670568A1 (de) * | 1967-07-07 | 1972-02-24 | Degussa | Verfahren zur Herstellung von substituierten 2-Mercapto-4,6-dichlor-s-triazinen |
US3709883A (en) * | 1971-07-02 | 1973-01-09 | Ciba Geigy Corp | Sulfur containing derivatives of dialkyl-4-hydroxyphenyltriazine |
US4831068A (en) * | 1987-02-27 | 1989-05-16 | Ciba-Geigy Corporation | Process for improving the photochemical stability of dyeings on polyester fibre materials |
ES2106308T3 (es) * | 1992-08-18 | 1997-11-01 | Ciba Geigy Ag | Procedimiento para la estabilizacion fotoquimica y termica de materiales de fibra de poliester teñidos o sin teñir. |
TW308601B (zh) * | 1995-01-18 | 1997-06-21 | Ciba Sc Holding Ag |
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1997
- 1997-03-04 ES ES97810121T patent/ES2308783T3/es not_active Expired - Lifetime
- 1997-03-04 EP EP97810121A patent/EP0795640B1/de not_active Expired - Lifetime
- 1997-03-04 DE DE59712948T patent/DE59712948D1/de not_active Expired - Lifetime
- 1997-03-10 US US08/814,301 patent/US5871669A/en not_active Expired - Fee Related
- 1997-03-11 JP JP05607997A patent/JP4118972B2/ja not_active Expired - Lifetime
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- 1997-03-12 TW TW086103042A patent/TW438925B/zh not_active IP Right Cessation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100410307C (zh) * | 2005-11-30 | 2008-08-13 | 中国石油化工股份有限公司 | 复合稳定剂及稳定的充油橡胶组合物 |
Also Published As
Publication number | Publication date |
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KR100442994B1 (ko) | 2004-11-03 |
EP0795640A1 (de) | 1997-09-17 |
CN1091794C (zh) | 2002-10-02 |
ES2308783T3 (es) | 2008-12-01 |
EP0795640B1 (de) | 2008-06-18 |
KR970065686A (ko) | 1997-10-13 |
JPH108025A (ja) | 1998-01-13 |
AU724535B2 (en) | 2000-09-21 |
MX9701878A (es) | 1998-04-30 |
TW438925B (en) | 2001-06-07 |
US5871669A (en) | 1999-02-16 |
JP4118972B2 (ja) | 2008-07-16 |
US5997769A (en) | 1999-12-07 |
ZA972131B (en) | 1997-09-15 |
AU1625697A (en) | 1997-09-18 |
BR9701269A (pt) | 1999-01-12 |
DE59712948D1 (de) | 2008-07-31 |
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