ZA200601076B - Water based concentrated product forms of light stabilizers made by a heterophase polymerization technique - Google Patents
Water based concentrated product forms of light stabilizers made by a heterophase polymerization technique Download PDFInfo
- Publication number
- ZA200601076B ZA200601076B ZA200601076A ZA200601076A ZA200601076B ZA 200601076 B ZA200601076 B ZA 200601076B ZA 200601076 A ZA200601076 A ZA 200601076A ZA 200601076 A ZA200601076 A ZA 200601076A ZA 200601076 B ZA200601076 B ZA 200601076B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbon atoms
- alkyl
- bis
- formula
- substituted
- Prior art date
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- 239000004611 light stabiliser Substances 0.000 title claims abstract description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000006116 polymerization reaction Methods 0.000 title claims description 13
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 239000006185 dispersion Substances 0.000 claims abstract description 17
- 239000002245 particle Substances 0.000 claims abstract description 13
- 239000000839 emulsion Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 4
- 239000000853 adhesive Substances 0.000 claims abstract description 3
- 230000001070 adhesive effect Effects 0.000 claims abstract description 3
- 239000008199 coating composition Substances 0.000 claims abstract description 3
- 229920003052 natural elastomer Polymers 0.000 claims abstract description 3
- 229920001194 natural rubber Polymers 0.000 claims abstract description 3
- 229920003051 synthetic elastomer Polymers 0.000 claims abstract description 3
- 239000005061 synthetic rubber Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 195
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- -1 ph enyl Chemical group 0.000 claims description 125
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 229920000642 polymer Polymers 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 239000006096 absorbing agent Substances 0.000 claims description 22
- 239000004815 dispersion polymer Substances 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229940116351 sebacate Drugs 0.000 claims description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- CMXLJKWFEJEFJE-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical compound C1=CC(OC)=CC=C1C=C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 CMXLJKWFEJEFJE-UHFFFAOYSA-N 0.000 claims description 3
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 3
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- PQJZHMCWDKOPQG-UHFFFAOYSA-N 2-anilino-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CC=C1 PQJZHMCWDKOPQG-UHFFFAOYSA-N 0.000 claims description 2
- GUCMKIKYKIHUTM-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-[2-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]piperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1CCN1C(=O)C(C)(C)NC(C)(C)C1 GUCMKIKYKIHUTM-UHFFFAOYSA-N 0.000 claims description 2
- STEYNUVPFMIUOY-UHFFFAOYSA-N 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 claims description 2
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- 239000007764 o/w emulsion Substances 0.000 claims description 2
- 239000004576 sand Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 230000015556 catabolic process Effects 0.000 claims 4
- 238000006731 degradation reaction Methods 0.000 claims 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 2
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 claims 1
- HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 claims 1
- IXAKLSFFPBJWBS-UHFFFAOYSA-N 2-cycloundecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diazaspiro[4.5]decan-4-one Chemical compound C1C(C)(C)NC(C)(C)CC21C(=O)NC(C1CCCCCCCCCC1)O2 IXAKLSFFPBJWBS-UHFFFAOYSA-N 0.000 claims 1
- HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 claims 1
- NPYDPROENPLGBR-UHFFFAOYSA-N 4,6-dichloro-n-cyclohexyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC(Cl)=NC(NC2CCCCC2)=N1 NPYDPROENPLGBR-UHFFFAOYSA-N 0.000 claims 1
- VPOKLVDHXARWQB-UHFFFAOYSA-N 7,7,9,9-tetramethyl-3-octyl-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound O=C1N(CCCCCCCC)C(=O)NC11CC(C)(C)NC(C)(C)C1 VPOKLVDHXARWQB-UHFFFAOYSA-N 0.000 claims 1
- FUCCNPWRCSWXBI-UHFFFAOYSA-N C(CCCCCCC)ON1C(C(CCC1(C)C)C(C(C(=O)O)C1C(N(C(CC1)(C)C)OCCCCCCCC)(C)C)C(=O)O)(C)C Chemical compound C(CCCCCCC)ON1C(C(CCC1(C)C)C(C(C(=O)O)C1C(N(C(CC1)(C)C)OCCCCCCCC)(C)C)C(=O)O)(C)C FUCCNPWRCSWXBI-UHFFFAOYSA-N 0.000 claims 1
- XTJYYRKHFBFRJV-UHFFFAOYSA-N CC1(NC(CC(C1)C(C(=O)O)N(C(C(=O)O)C1CC(NC(C1)(C)C)(C)C)C(C(=O)O)C1CC(NC(C1)(C)C)(C)C)(C)C)C Chemical compound CC1(NC(CC(C1)C(C(=O)O)N(C(C(=O)O)C1CC(NC(C1)(C)C)(C)C)C(C(=O)O)C1CC(NC(C1)(C)C)(C)C)(C)C)C XTJYYRKHFBFRJV-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- KGUHWHHMNQPSRV-UHFFFAOYSA-N [1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 KGUHWHHMNQPSRV-UHFFFAOYSA-N 0.000 claims 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- UTLVQENMPIUJSJ-QTARTGBFSA-N dT10 Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 UTLVQENMPIUJSJ-QTARTGBFSA-N 0.000 claims 1
- WTVNFKVGGUWHQC-UHFFFAOYSA-N decane-2,4-dione Chemical compound CCCCCCC(=O)CC(C)=O WTVNFKVGGUWHQC-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- UONLDZHKYCFZRW-UHFFFAOYSA-N n-[6-[formyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino]hexyl]-n-(2,2,6,6-tetramethylpiperidin-4-yl)formamide Chemical compound C1C(C)(C)NC(C)(C)CC1N(C=O)CCCCCCN(C=O)C1CC(C)(C)NC(C)(C)C1 UONLDZHKYCFZRW-UHFFFAOYSA-N 0.000 claims 1
- DARUEKWVLGHJJT-UHFFFAOYSA-N n-butyl-1-[4-[4-(butylamino)-2,2,6,6-tetramethylpiperidin-1-yl]-6-chloro-1,3,5-triazin-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCC)CC(C)(C)N1C1=NC(Cl)=NC(N2C(CC(CC2(C)C)NCCCC)(C)C)=N1 DARUEKWVLGHJJT-UHFFFAOYSA-N 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 1
- 229920001169 thermoplastic Polymers 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 239000000976 ink Substances 0.000 abstract description 5
- 239000004615 ingredient Substances 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 19
- 239000012964 benzotriazole Substances 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical compound OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
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- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- OLBWDGJTEXRJLY-UHFFFAOYSA-N tetradecyl 3-(2,2,4,4-tetramethyl-21-oxo-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-20-yl)propanoate Chemical compound O1C2(CCCCCCCCCCC2)N(CCC(=O)OCCCCCCCCCCCCCC)C(=O)C21CC(C)(C)NC(C)(C)C2 OLBWDGJTEXRJLY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Cosmetics (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03103348 | 2003-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200601076B true ZA200601076B (en) | 2007-04-25 |
Family
ID=34259278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200601076A ZA200601076B (en) | 2003-09-11 | 2006-02-07 | Water based concentrated product forms of light stabilizers made by a heterophase polymerization technique |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7687554B2 (https=) |
| EP (1) | EP1664128B1 (https=) |
| JP (3) | JP2007505179A (https=) |
| KR (1) | KR101133459B1 (https=) |
| CN (1) | CN100415777C (https=) |
| AT (1) | ATE421541T1 (https=) |
| AU (1) | AU2004270402A1 (https=) |
| BR (1) | BRPI0414249B1 (https=) |
| CA (1) | CA2537068A1 (https=) |
| DE (1) | DE602004019230D1 (https=) |
| IN (1) | IN2006CH01243A (https=) |
| MX (1) | MXPA06002754A (https=) |
| RU (1) | RU2354664C2 (https=) |
| TW (1) | TW200521176A (https=) |
| WO (1) | WO2005023878A1 (https=) |
| ZA (1) | ZA200601076B (https=) |
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| KR100704825B1 (ko) | 2003-02-21 | 2007-04-09 | 바이엘 쉐링 파마 악티엔게젤샤프트 | Ｕｖ 안정성 경피 치료 플라스터 |
| US8668925B2 (en) * | 2003-12-12 | 2014-03-11 | Bayer Intellectual Property Gmbh | Transdermal delivery of hormones without the need of penetration enhancers |
| EP1719504A1 (de) * | 2005-05-02 | 2006-11-08 | Schering AG | Festes transdermales therapeutisches System mit UV-Absorber |
| US8962013B2 (en) | 2005-05-02 | 2015-02-24 | Bayer Intellectual Property Gmbh | Multi-layered transdermal system with triazine UV absorber |
| US7569157B2 (en) * | 2005-06-22 | 2009-08-04 | Hunt Holdings, Inc. | Rotted wood stabilizer composition and methods of making and using same |
| DE102006005500A1 (de) * | 2006-02-07 | 2007-08-09 | Degussa Gmbh | Verwendung von Polymerpulver, hergestellt aus einer Dispersion, in einem formgebenden Verfahren und Formkörper, hergestellt aus diesem Polymerpulver |
| RU2439082C2 (ru) * | 2006-07-04 | 2012-01-10 | Циба Холдинг Инк. | Концентрированные формы готовых фотоинициаторов на водной основе, полученные с помощью гетерофазной полимеризации |
| US9828597B2 (en) | 2006-11-22 | 2017-11-28 | Toyota Motor Engineering & Manufacturing North America, Inc. | Biofunctional materials |
| ES2646273T3 (es) * | 2007-07-09 | 2017-12-13 | Basf Se | Formas de productos concentrados a base de agua de absorbentes de UV orgánicos solubles en aceite |
| WO2009103651A2 (en) | 2008-02-21 | 2009-08-27 | Basf Se | Preparation of cationic nanoparticles and personal care compositions comprising said nanoparticles |
| EP2135598B1 (en) * | 2008-06-16 | 2011-08-03 | Rohm and Haas Company | Particle Containing Ultraviolet Absorber |
| KR101346390B1 (ko) | 2008-07-28 | 2014-01-02 | 고쿠리츠 다이가쿠 호진 교토 다이가쿠 | 수성 안료 분산액, 및 사용 |
| WO2010121387A1 (en) * | 2009-04-20 | 2010-10-28 | ETH Zürich | Polymer nanoparticles |
| US8580876B2 (en) | 2009-07-29 | 2013-11-12 | Basf Se | Encapsulated phenolic antioxidants |
| KR20130039736A (ko) * | 2010-05-14 | 2013-04-22 | 후지필름 이미징 컬러런츠 리미티드 | 인쇄 방법, 중합체 및 잉크 |
| US9388370B2 (en) | 2010-06-21 | 2016-07-12 | Toyota Motor Engineering & Manufacturing North America, Inc. | Thermolysin-like protease for cleaning insect body stains |
| US8796009B2 (en) | 2010-06-21 | 2014-08-05 | Toyota Motor Engineering & Manufacturing North America, Inc. | Clearcoat containing thermolysin-like protease from Bacillus stearothermophilus for cleaning of insect body stains |
| US10988714B2 (en) | 2010-06-21 | 2021-04-27 | Regents Of The University Of Minnesota | Methods of facilitating removal of a fingerprint from a substrate or a coating |
| US11015149B2 (en) | 2010-06-21 | 2021-05-25 | Toyota Motor Corporation | Methods of facilitating removal of a fingerprint |
| US9121016B2 (en) | 2011-09-09 | 2015-09-01 | Toyota Motor Engineering & Manufacturing North America, Inc. | Coatings containing polymer modified enzyme for stable self-cleaning of organic stains |
| DE102010041247A1 (de) * | 2010-09-23 | 2012-03-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung |
| US8647471B2 (en) * | 2010-12-22 | 2014-02-11 | Bayer Materialscience Llc | Process for the production of sized and/or wet-strength papers, paperboards and cardboards |
| JP5895851B2 (ja) * | 2011-01-25 | 2016-03-30 | 住友大阪セメント株式会社 | 有機系紫外線吸収剤含有樹脂粒子の製造方法 |
| EP2885355A1 (en) * | 2012-08-16 | 2015-06-24 | Basf Se | Stable uv absorber composition |
| EP2981579B1 (en) * | 2013-04-02 | 2018-10-17 | Basf Se | Coated carbon fiber reinforced plastic parts |
| KR102335051B1 (ko) | 2013-07-08 | 2021-12-07 | 바스프 에스이 | 신규 광 안정화제 |
| US20150119510A1 (en) * | 2013-10-30 | 2015-04-30 | Xerox Corporation | Inkjet ink containing polystyren copolymer latex suitable for indirect printing |
| JP5811258B2 (ja) * | 2013-11-22 | 2015-11-11 | ダイキン工業株式会社 | 表面処理剤 |
| CN105745272B (zh) * | 2013-11-22 | 2018-07-03 | 大金工业株式会社 | 水系乳液表面处理剂 |
| KR101872133B1 (ko) * | 2013-11-22 | 2018-06-27 | 다이킨 고교 가부시키가이샤 | 수계 표면 처리제 |
| KR20160105790A (ko) | 2013-11-27 | 2016-09-07 | 바스프 에스이 | 세탁 방법에서 오염물 방출제로서의 랜덤 공중합체 |
| WO2015173029A1 (en) * | 2014-05-13 | 2015-11-19 | Basf Se | An agrochemical composition comprising a pesticide and submicron particles containing a light stabilizer |
| EP3197923B1 (en) | 2014-09-23 | 2021-09-01 | Basf Se | Aqueous polymer-silicon oil hybrid composition |
| CN106987078A (zh) * | 2017-04-01 | 2017-07-28 | 华南理工大学 | 一种可水分散性光稳定剂及其制备方法 |
| WO2018185710A1 (en) * | 2017-04-07 | 2018-10-11 | Sabic Global Technologies B.V. | Durable surface hardened coating or overcoating for protecting plants from pests |
| KR102707246B1 (ko) | 2017-09-01 | 2024-09-20 | 바스프 에스이 | 오일-가용성 유기 uv 흡수제의 수계 농축 생성물 형태 |
| EA202090494A1 (ru) | 2017-09-11 | 2020-07-13 | Басф Корпорейшн | Водные полимерные дисперсии, способ их получения и их применение в качестве депрессантов температуры застывания сырой нефти, нефти и нефтепродуктов |
| JP2020015790A (ja) | 2018-07-24 | 2020-01-30 | 株式会社リコー | 硬化型組成物、硬化型インク、収容容器、２次元又は３次元の像形成装置、２次元又は３次元の像形成方法、硬化物、及び印刷物 |
| EP3628724B1 (en) | 2018-09-25 | 2021-07-28 | Basf Se | Powder and granule, process for making such powder and granule, and use thereof |
| FR3093335A1 (fr) * | 2019-02-28 | 2020-09-04 | Valeo Systemes D'essuyage | Composition de revêtement pour lame d’essuyage pour balai d’essuie-glace et lame d’essuyage associée |
| JP7030252B1 (ja) | 2020-09-11 | 2022-03-04 | 大阪ガスケミカル株式会社 | 樹脂混練用添加剤 |
| WO2025125201A1 (en) | 2023-12-11 | 2025-06-19 | Basf Se | Aqueous dispersion comprising polymer particles for improving the resistance of waterborne coatings |
| WO2026027355A1 (en) | 2024-07-29 | 2026-02-05 | Basf Se | Process for decolorization of light stabilizers |
| WO2026073795A1 (en) | 2024-10-01 | 2026-04-09 | Basf Se | Mixtures of additives for the stabilization of adhesives, sealants and elastomers |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0226538B1 (de) * | 1985-12-06 | 1991-09-11 | Ciba SC Holding AG | Lichtstabilisierte Polymermikropartikel |
| US5274016A (en) | 1985-12-06 | 1993-12-28 | Ciba-Geigy Corporation | Light-stabilized polymer microparticles |
| EP0389419B1 (en) * | 1989-03-21 | 1996-05-01 | Ciba-Geigy Ag | Non-migrating 1-hydrocarbyloxy hindered amine compounds as polymer stabilizers |
| JP2595182B2 (ja) * | 1993-03-22 | 1997-03-26 | 三井東圧化学株式会社 | 塩化ビニル類の重合方法 |
| JP3461026B2 (ja) * | 1994-04-22 | 2003-10-27 | 大日本インキ化学工業株式会社 | 樹脂水性分散液の製造方法 |
| JPH10152507A (ja) * | 1996-11-22 | 1998-06-09 | Toagosei Co Ltd | 水性エマルジョンの製造方法 |
| DE19648744A1 (de) * | 1996-11-25 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung einer Polymerdispersion durch radikalische wäßrige Emulsionspolymerisation mit einer kontinuierlich hergestellten wäßrigen Monomerenemulsion |
| DE19810268A1 (de) * | 1998-03-10 | 1999-09-16 | Basf Ag | Stabilisatoren enthaltende Polymerdispersionen oder Polymerlösungen und daraus erhältliche Polymerpräparationen |
| JP3736176B2 (ja) * | 1999-02-03 | 2006-01-18 | 東亞合成株式会社 | 水性エマルジョンの製造方法 |
| GB0001752D0 (en) | 2000-01-27 | 2000-03-15 | Ciba Spec Chem Water Treat Ltd | Particulate compositions and their manufacture |
| JP2001226415A (ja) * | 2000-02-14 | 2001-08-21 | Toagosei Co Ltd | 水性エマルジョンの製造方法 |
| DE50115609D1 (de) | 2000-02-17 | 2010-10-14 | Basf Se | Wässrige Dispersion wasserunlöslicher organischer UV-Filtersubstanzen |
| JP2002003538A (ja) * | 2000-06-23 | 2002-01-09 | Kansai Paint Co Ltd | 共重合体エマルション及びこれを含む水性塗料組成物 |
| MXPA01008706A (es) * | 2000-09-03 | 2004-08-12 | Rohm & Haas | Sistemas aditivos polimericos altos en solidos: composiciones, procesos y productos de los mismos. |
| DE10046927A1 (de) * | 2000-09-21 | 2002-04-25 | Basf Ag | Farbmittelhaltige wässrige Polymerdispersion |
| DE10106566A1 (de) | 2001-02-13 | 2002-08-22 | Basf Coatings Ag | Von flüchtigen organischen Stoffen im wesentlichen oder völlig freier wäßriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
-
2004
- 2004-09-01 WO PCT/EP2004/051980 patent/WO2005023878A1/en not_active Ceased
- 2004-09-01 CA CA002537068A patent/CA2537068A1/en not_active Abandoned
- 2004-09-01 CN CNB2004800260412A patent/CN100415777C/zh not_active Expired - Lifetime
- 2004-09-01 EP EP04766661A patent/EP1664128B1/en not_active Expired - Lifetime
- 2004-09-01 AU AU2004270402A patent/AU2004270402A1/en not_active Abandoned
- 2004-09-01 MX MXPA06002754A patent/MXPA06002754A/es unknown
- 2004-09-01 RU RU2006111580/04A patent/RU2354664C2/ru active
- 2004-09-01 BR BRPI0414249-7B1A patent/BRPI0414249B1/pt not_active IP Right Cessation
- 2004-09-01 US US10/570,736 patent/US7687554B2/en not_active Expired - Lifetime
- 2004-09-01 KR KR1020067004973A patent/KR101133459B1/ko not_active Expired - Fee Related
- 2004-09-01 JP JP2006525812A patent/JP2007505179A/ja active Pending
- 2004-09-01 AT AT04766661T patent/ATE421541T1/de not_active IP Right Cessation
- 2004-09-01 DE DE602004019230T patent/DE602004019230D1/de not_active Expired - Lifetime
- 2004-09-10 TW TW093127421A patent/TW200521176A/zh unknown
-
2006
- 2006-02-07 ZA ZA200601076A patent/ZA200601076B/en unknown
- 2006-04-10 IN IN1243CH2006 patent/IN2006CH01243A/en unknown
-
2011
- 2011-05-25 JP JP2011116741A patent/JP2011241400A/ja active Pending
-
2014
- 2014-12-05 JP JP2014246990A patent/JP6129146B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU2354664C2 (ru) | 2009-05-10 |
| IN2006CH01243A (https=) | 2007-08-10 |
| CN100415777C (zh) | 2008-09-03 |
| US20060287416A1 (en) | 2006-12-21 |
| JP6129146B2 (ja) | 2017-05-17 |
| MXPA06002754A (es) | 2006-06-14 |
| BRPI0414249A (pt) | 2006-11-21 |
| US7687554B2 (en) | 2010-03-30 |
| KR101133459B1 (ko) | 2012-04-12 |
| TW200521176A (en) | 2005-07-01 |
| WO2005023878A1 (en) | 2005-03-17 |
| EP1664128A1 (en) | 2006-06-07 |
| CA2537068A1 (en) | 2005-03-17 |
| JP2011241400A (ja) | 2011-12-01 |
| ATE421541T1 (de) | 2009-02-15 |
| CN1849343A (zh) | 2006-10-18 |
| KR20070004518A (ko) | 2007-01-09 |
| AU2004270402A1 (en) | 2005-03-17 |
| DE602004019230D1 (de) | 2009-03-12 |
| RU2006111580A (ru) | 2007-10-27 |
| EP1664128B1 (en) | 2009-01-21 |
| JP2015091980A (ja) | 2015-05-14 |
| BRPI0414249B1 (pt) | 2013-08-06 |
| JP2007505179A (ja) | 2007-03-08 |
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