TWI316513B - Highly compatible hydroxyphenyltriazine uv-absorbers - Google Patents

Info

Publication number

TWI316513B

TWI316513B TW091113130A TW91113130A TWI316513B TW I316513 B TWI316513 B TW I316513B TW 091113130 A TW091113130 A TW 091113130A TW 91113130 A TW91113130 A TW 91113130A TW I316513 B TWI316513 B TW I316513B

Authority

TW

Taiwan

Prior art keywords

hydrogen

formula

group

tert

alkyl

Prior art date

2001-07-02

Links

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• 239000006096 absorbing agent Substances 0.000 title description 11
• VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical compound OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title description 5
• -1 hydroxyphenyl triazine compound Chemical class 0.000 claims description 145
• 239000000203 mixture Substances 0.000 claims description 90
• 150000001875 compounds Chemical class 0.000 claims description 79
• 239000001257 hydrogen Substances 0.000 claims description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• 229920000642 polymer Polymers 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 239000000654 additive Substances 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 229920003023 plastic Polymers 0.000 claims description 25
• 239000004033 plastic Substances 0.000 claims description 24
• 239000000463 material Substances 0.000 claims description 23
• 238000010521 absorption reaction Methods 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 150000001412 amines Chemical class 0.000 claims description 14
• 230000035515 penetration Effects 0.000 claims description 14
• 239000004417 polycarbonate Substances 0.000 claims description 12
• 230000005855 radiation Effects 0.000 claims description 11
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 229920000728 polyester Polymers 0.000 claims description 10
• 229920000768 polyamine Polymers 0.000 claims description 9
• 229920000515 polycarbonate Polymers 0.000 claims description 9
• 229920000098 polyolefin Polymers 0.000 claims description 9
• 239000004952 Polyamide Substances 0.000 claims description 7
• 229920002647 polyamide Polymers 0.000 claims description 7
• 229920001897 terpolymer Polymers 0.000 claims description 6
• 239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
• 239000000460 chlorine Substances 0.000 claims description 5
• 239000002537 cosmetic Substances 0.000 claims description 5
• 239000011118 polyvinyl acetate Substances 0.000 claims description 5
• 229920002689 polyvinyl acetate Polymers 0.000 claims description 5
• 229920002451 polyvinyl alcohol Polymers 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 239000007789 gas Substances 0.000 claims description 4
• 230000009931 harmful effect Effects 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 235000021485 packed food Nutrition 0.000 claims description 3
• 229920006243 acrylic copolymer Polymers 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 239000003063 flame retardant Substances 0.000 claims description 2
• 239000005003 food packaging material Substances 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 229910052742 iron Inorganic materials 0.000 claims description 2
• 239000002530 phenolic antioxidant Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 14
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 150000001983 dialkylethers Chemical class 0.000 claims 1
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims 1
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 description 40
• 238000003786 synthesis reaction Methods 0.000 description 40
• 239000010408 film Substances 0.000 description 39
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 36
• 229920001577 copolymer Polymers 0.000 description 35
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 29
• 238000000034 method Methods 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• 239000000178 monomer Substances 0.000 description 21
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
• 150000002148 esters Chemical class 0.000 description 20
• 239000000543 intermediate Substances 0.000 description 20
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 20
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
• 239000002253 acid Substances 0.000 description 19
• 239000000243 solution Substances 0.000 description 18
• 239000002585 base Substances 0.000 description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 229910052799 carbon Inorganic materials 0.000 description 15
• 238000002844 melting Methods 0.000 description 15
• 230000008018 melting Effects 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 14
• 239000005977 Ethylene Substances 0.000 description 14
• 150000002009 diols Chemical class 0.000 description 13
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
• 239000004743 Polypropylene Substances 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
• 239000004698 Polyethylene Substances 0.000 description 11
• 239000007983 Tris buffer Substances 0.000 description 11
• 229960003742 phenol Drugs 0.000 description 11
• 229920000573 polyethylene Polymers 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• 230000000996 additive effect Effects 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 10
• 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
• 238000005227 gel permeation chromatography Methods 0.000 description 9
• 239000004700 high-density polyethylene Substances 0.000 description 9
• 229910052751 metal Inorganic materials 0.000 description 9
• 239000002184 metal Substances 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 239000004721 Polyphenylene oxide Substances 0.000 description 8
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 8
• 239000012964 benzotriazole Substances 0.000 description 8
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
• 229920001903 high density polyethylene Polymers 0.000 description 8
• 239000004615 ingredient Substances 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 235000019198 oils Nutrition 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• 229920002857 polybutadiene Polymers 0.000 description 8
• 229920001155 polypropylene Polymers 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000003381 stabilizer Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 7
• 239000002202 Polyethylene glycol Substances 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 239000010949 copper Substances 0.000 description 7
• 229910052736 halogen Inorganic materials 0.000 description 7
• 150000002367 halogens Chemical class 0.000 description 7
• 229920001223 polyethylene glycol Polymers 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
• 150000001993 dienes Chemical class 0.000 description 6
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 229920006324 polyoxymethylene Polymers 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• 229910000029 sodium carbonate Inorganic materials 0.000 description 6
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
• 239000004305 biphenyl Substances 0.000 description 5
• 239000007859 condensation product Substances 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 229920001519 homopolymer Polymers 0.000 description 5
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 229920006380 polyphenylene oxide Polymers 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• 239000000052 vinegar Substances 0.000 description 5
• 235000021419 vinegar Nutrition 0.000 description 5
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 150000001335 aliphatic alkanes Chemical group 0.000 description 4
• 150000001336 alkenes Chemical class 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 description 4
• 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 4
• MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
• ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 4
• 229920001971 elastomer Polymers 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 235000013305 food Nutrition 0.000 description 4
• 239000011521 glass Substances 0.000 description 4
• 229920000092 linear low density polyethylene Polymers 0.000 description 4
• 239000004707 linear low-density polyethylene Substances 0.000 description 4
• 150000005673 monoalkenes Chemical class 0.000 description 4
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
• 150000002815 nickel Chemical class 0.000 description 4
• 125000003884 phenylalkyl group Chemical group 0.000 description 4
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
• 229920000570 polyether Polymers 0.000 description 4
• 238000006116 polymerization reaction Methods 0.000 description 4
• 239000004814 polyurethane Substances 0.000 description 4
• 229940068984 polyvinyl alcohol Drugs 0.000 description 4
• 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 235000019260 propionic acid Nutrition 0.000 description 4
• 235000013772 propylene glycol Nutrition 0.000 description 4
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 150000005846 sugar alcohols Polymers 0.000 description 4
• YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
• ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
• 238000000870 ultraviolet spectroscopy Methods 0.000 description 4
• 229920002554 vinyl polymer Polymers 0.000 description 4
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
• FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
• OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 3
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
• GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
• IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
• 239000001361 adipic acid Substances 0.000 description 3
• 235000011037 adipic acid Nutrition 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 235000013361 beverage Nutrition 0.000 description 3
• 239000001273 butane Substances 0.000 description 3
• 230000015556 catabolic process Effects 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
• 238000006731 degradation reaction Methods 0.000 description 3
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• GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 3
• 239000000806 elastomer Substances 0.000 description 3
• 230000032050 esterification Effects 0.000 description 3
• 238000005886 esterification reaction Methods 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
• 238000005984 hydrogenation reaction Methods 0.000 description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
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