NL1018251C2 - Organometallische monoacylalkylfosfinen. - Google Patents

Info

Publication number

NL1018251C2

NL1018251C2 NL1018251A NL1018251A NL1018251C2 NL 1018251 C2 NL1018251 C2 NL 1018251C2 NL 1018251 A NL1018251 A NL 1018251A NL 1018251 A NL1018251 A NL 1018251A NL 1018251 C2 NL1018251 C2 NL 1018251C2

Authority

NL

Netherlands

Prior art keywords

alkyl

substituted

oxide

unsubstituted

interrupted

Prior art date

2000-06-08

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• 150000003003 phosphines Chemical class 0.000 title claims description 10
• 125000002524 organometallic group Chemical group 0.000 title description 3
• -1 biphenylyl Chemical group 0.000 claims abstract description 537
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 229
• 150000001875 compounds Chemical class 0.000 claims abstract description 181
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 156
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 147
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 118
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 101
• 150000002367 halogens Chemical class 0.000 claims abstract description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 96
• 239000001257 hydrogen Substances 0.000 claims abstract description 85
• 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 abstract description 70
• 229910052744 lithium Inorganic materials 0.000 claims abstract description 66
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 61
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 53
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 49
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 44
• 238000002360 preparation method Methods 0.000 claims abstract description 42
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 36
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 29
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 21
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims abstract description 19
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 18
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 17
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
• 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
• 229910052700 potassium Inorganic materials 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 93
• 238000006243 chemical reaction Methods 0.000 claims description 72
• 238000000576 coating method Methods 0.000 claims description 58
• 229910052799 carbon Inorganic materials 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 45
• 239000000463 material Substances 0.000 claims description 43
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 150000001266 acyl halides Chemical class 0.000 claims description 34
• 238000004519 manufacturing process Methods 0.000 claims description 33
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 28
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 239000003999 initiator Substances 0.000 claims description 23
• 239000002904 solvent Substances 0.000 claims description 23
• 238000007639 printing Methods 0.000 claims description 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 239000000976 ink Substances 0.000 claims description 20
• 229920000642 polymer Polymers 0.000 claims description 20
• 230000008569 process Effects 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 239000011593 sulfur Substances 0.000 claims description 19
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 18
• 239000000843 powder Substances 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• 125000005724 cycloalkenylene group Chemical group 0.000 claims description 17
• 238000007254 oxidation reaction Methods 0.000 claims description 17
• 239000000758 substrate Substances 0.000 claims description 17
• 239000000654 additive Substances 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 16
• 230000003647 oxidation Effects 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• 239000007858 starting material Substances 0.000 claims description 16
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 15
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 15
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 13
• 230000003287 optical effect Effects 0.000 claims description 13
• 150000003568 thioethers Chemical class 0.000 claims description 13
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
• 238000007645 offset printing Methods 0.000 claims description 10
• REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical compound P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 claims description 10
• 238000007650 screen-printing Methods 0.000 claims description 10
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 8
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 8
• 239000002131 composite material Substances 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 235000010290 biphenyl Nutrition 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 150000003254 radicals Chemical class 0.000 claims description 7
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
• 239000000835 fiber Substances 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
• 238000012360 testing method Methods 0.000 claims description 5
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• 239000000853 adhesive Substances 0.000 claims description 4
• 230000001070 adhesive effect Effects 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 239000003094 microcapsule Substances 0.000 claims description 4
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
• 230000033458 reproduction Effects 0.000 claims description 4
• 125000005504 styryl group Chemical group 0.000 claims description 4
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 230000001678 irradiating effect Effects 0.000 claims description 3
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
• LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 3
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 229910052727 yttrium Inorganic materials 0.000 claims description 2
• 229910018557 Si O Inorganic materials 0.000 claims 1
• 239000013256 coordination polymer Substances 0.000 claims 1
• 150000002642 lithium compounds Chemical class 0.000 claims 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 3
• MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 266
• 150000002148 esters Chemical class 0.000 description 70
• HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 60
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 51
• 229910001392 phosphorus oxide Inorganic materials 0.000 description 49
• VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 47
• 239000002253 acid Substances 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 38
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 35
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 35
• 239000011248 coating agent Substances 0.000 description 21
• TXBIZRLVIDXDGB-UHFFFAOYSA-N 2-methylpropylphosphane Chemical compound CC(C)CP TXBIZRLVIDXDGB-UHFFFAOYSA-N 0.000 description 19
• 239000000460 chlorine Substances 0.000 description 18
• 229910052751 metal Inorganic materials 0.000 description 18
• 239000002184 metal Substances 0.000 description 18
• 239000000243 solution Substances 0.000 description 17
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 16
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
• 229920001577 copolymer Polymers 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 15
• 239000000049 pigment Substances 0.000 description 15
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 239000010410 layer Substances 0.000 description 14
• 238000001723 curing Methods 0.000 description 13
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
• 125000004450 alkenylene group Chemical group 0.000 description 12
• 239000000178 monomer Substances 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• 229920005862 polyol Polymers 0.000 description 11
• 239000004808 2-ethylhexylester Substances 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
• 150000001335 aliphatic alkanes Chemical class 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 9
• WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 description 9
• IDNNYZOOKGKJBK-UHFFFAOYSA-N CC(C)C[PH2]=O Chemical compound CC(C)C[PH2]=O IDNNYZOOKGKJBK-UHFFFAOYSA-N 0.000 description 9
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
• AZHPCFQBBJISDG-UHFFFAOYSA-N ethyl(oxido)phosphanium Chemical compound CC[PH2]=O AZHPCFQBBJISDG-UHFFFAOYSA-N 0.000 description 9
• 229920000728 polyester Polymers 0.000 description 9
• 150000003077 polyols Chemical class 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• DVIDIZXCFDHODG-UHFFFAOYSA-N cyclopentylphosphane Chemical compound PC1CCCC1 DVIDIZXCFDHODG-UHFFFAOYSA-N 0.000 description 8
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 229920005989 resin Polymers 0.000 description 8
• 239000011347 resin Substances 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
• XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 239000012965 benzophenone Substances 0.000 description 7
• 239000011230 binding agent Substances 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 238000004821 distillation Methods 0.000 description 7
• 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 7
• 239000000975 dye Substances 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
• 229910052753 mercury Inorganic materials 0.000 description 7
• 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 7
• WEYHWRWGAACKIL-UHFFFAOYSA-N pentylphosphane Chemical compound CCCCCP WEYHWRWGAACKIL-UHFFFAOYSA-N 0.000 description 7
• 229920002635 polyurethane Polymers 0.000 description 7
• 239000004814 polyurethane Substances 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 6
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 150000001350 alkyl halides Chemical class 0.000 description 6
• 239000012964 benzotriazole Substances 0.000 description 6
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
• WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• 239000007859 condensation product Substances 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 6
• 239000012442 inert solvent Substances 0.000 description 6
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 150000002903 organophosphorus compounds Chemical class 0.000 description 6
• AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 6
• 229920000647 polyepoxide Polymers 0.000 description 6
• 239000007787 solid Substances 0.000 description 6
• 239000000600 sorbitol Substances 0.000 description 6
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