JP7412349B2 - イオン性親水化ポリイソシアネートの含水率 - Google Patents
イオン性親水化ポリイソシアネートの含水率 Download PDFInfo
- Publication number
- JP7412349B2 JP7412349B2 JP2020555347A JP2020555347A JP7412349B2 JP 7412349 B2 JP7412349 B2 JP 7412349B2 JP 2020555347 A JP2020555347 A JP 2020555347A JP 2020555347 A JP2020555347 A JP 2020555347A JP 7412349 B2 JP7412349 B2 JP 7412349B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfonic acid
- acid
- weight
- polyisocyanate
- group
- 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.)
- Active
Links
- 239000005056 polyisocyanate Substances 0.000 title claims description 102
- 229920001228 polyisocyanate Polymers 0.000 title claims description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 57
- -1 aliphatic alcohols Chemical class 0.000 claims description 111
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 238000004519 manufacturing process Methods 0.000 claims description 31
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 26
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 16
- 150000003512 tertiary amines Chemical class 0.000 claims description 15
- 230000002209 hydrophobic effect Effects 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 14
- 239000008199 coating composition Substances 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 12
- 150000002894 organic compounds Chemical class 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- PJWWRFATQTVXHA-UHFFFAOYSA-N Cyclohexylaminopropanesulfonic acid Chemical compound OS(=O)(=O)CCCNC1CCCCC1 PJWWRFATQTVXHA-UHFFFAOYSA-N 0.000 claims description 6
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- XNPKNHHFCKSMRV-UHFFFAOYSA-N 4-(cyclohexylamino)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCNC1CCCCC1 XNPKNHHFCKSMRV-UHFFFAOYSA-N 0.000 claims description 4
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims description 4
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 4
- GHSGJYANZVSEPH-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanesulfonic acid Chemical compound CC(C)NCCS(O)(=O)=O GHSGJYANZVSEPH-UHFFFAOYSA-N 0.000 claims description 3
- OQADVBLQZQTGLL-UHFFFAOYSA-N 2-ethyl-n,n-dimethylhexan-1-amine Chemical compound CCCCC(CC)CN(C)C OQADVBLQZQTGLL-UHFFFAOYSA-N 0.000 claims description 3
- ZBSWKBYXONRLTM-UHFFFAOYSA-N 3-(propan-2-ylamino)propane-1-sulfonic acid Chemical compound CC(C)NCCCS(O)(=O)=O ZBSWKBYXONRLTM-UHFFFAOYSA-N 0.000 claims description 3
- QKVSMSABRNCNRS-UHFFFAOYSA-N 4-(2-methylpropyl)morpholine Chemical compound CC(C)CN1CCOCC1 QKVSMSABRNCNRS-UHFFFAOYSA-N 0.000 claims description 3
- ZCVOCAWBPMHJPF-UHFFFAOYSA-N 4-(propan-2-ylamino)butane-1-sulfonic acid Chemical compound C(C)(C)NCCCCS(=O)(=O)O ZCVOCAWBPMHJPF-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 2
- STMRFGRNIRUIML-UHFFFAOYSA-N 2-ethyl-n,n-di(propan-2-yl)hexan-1-amine Chemical compound CCCCC(CC)CN(C(C)C)C(C)C STMRFGRNIRUIML-UHFFFAOYSA-N 0.000 claims description 2
- GSCCALZHGUWNJW-UHFFFAOYSA-N N-Cyclohexyl-N-methylcyclohexanamine Chemical compound C1CCCCC1N(C)C1CCCCC1 GSCCALZHGUWNJW-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 2
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 19
- 150000001298 alcohols Chemical class 0.000 description 13
- 239000003973 paint Substances 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000004971 Cross linker Substances 0.000 description 9
- 230000001804 emulsifying effect Effects 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical class CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920002396 Polyurea Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical class CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical class CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- MKWKNSIESPFAQN-UHFFFAOYSA-N N-cyclohexyl-2-aminoethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCCCC1 MKWKNSIESPFAQN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical group CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 239000011527 polyurethane coating Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical class CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- HZHMBNYJWQUCHI-UHFFFAOYSA-N 3-aminobutane-1-sulfonic acid Chemical compound CC(N)CCS(O)(=O)=O HZHMBNYJWQUCHI-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 description 2
- HVDVDGGJUWKUJB-UHFFFAOYSA-N 6-chloro-n,n-dimethylhexan-1-amine Chemical compound CN(C)CCCCCCCl HVDVDGGJUWKUJB-UHFFFAOYSA-N 0.000 description 2
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 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 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 229940093858 ethyl acetoacetate Drugs 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VEAZEPMQWHPHAG-UHFFFAOYSA-N n,n,n',n'-tetramethylbutane-1,4-diamine Chemical compound CN(C)CCCCN(C)C VEAZEPMQWHPHAG-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 2
- 238000003221 volumetric titration Methods 0.000 description 2
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 2
- SXFBQAMLJMDXOD-UHFFFAOYSA-N (+)-hydrogentartrate bitartrate salt Chemical compound OC(=O)C(O)C(O)C(O)=O.OC(=O)C(O)C(O)C(O)=O SXFBQAMLJMDXOD-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical class OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- NRLOQEQAWOKEJF-UHFFFAOYSA-N (6-methyl-1,1-diphenylheptyl) dihydrogen phosphite Chemical compound C=1C=CC=CC=1C(OP(O)O)(CCCCC(C)C)C1=CC=CC=C1 NRLOQEQAWOKEJF-UHFFFAOYSA-N 0.000 description 1
- UTMRXNXUXKXVNK-UHFFFAOYSA-N (8-methyl-1-phenylnonyl) dihydrogen phosphite Chemical compound CC(C)CCCCCCC(OP(O)O)C1=CC=CC=C1 UTMRXNXUXKXVNK-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- AGJCSCSSMFRMFQ-UHFFFAOYSA-N 1,4-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=C(C(C)(C)N=C=O)C=C1 AGJCSCSSMFRMFQ-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- XZZWOTQMUOIIFX-UHFFFAOYSA-N 1-(2-diphenoxyphosphanyloxypropoxy)propan-2-yl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC(C)COCC(C)OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 XZZWOTQMUOIIFX-UHFFFAOYSA-N 0.000 description 1
- LYUGPLUDRALHKJ-UHFFFAOYSA-N 1-(cyclohexylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC1CCCCC1 LYUGPLUDRALHKJ-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- HPLQLQQLRLADHV-UHFFFAOYSA-N 1-[bis(6-methylheptoxy)phosphoryl]-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(P(=O)(OCCCCCC(C)C)OCCCCCC(C)C)C=C1 HPLQLQQLRLADHV-UHFFFAOYSA-N 0.000 description 1
- INARFNQOWWSXLS-UHFFFAOYSA-N 1-amino-2-methylpropane-1-sulfonic acid Chemical group CC(C)C(N)S(O)(=O)=O INARFNQOWWSXLS-UHFFFAOYSA-N 0.000 description 1
- BVJHPLDMZKSTIL-UHFFFAOYSA-N 1-aminoheptane-1-sulfonic acid Chemical compound CCCCCCC(N)S(O)(=O)=O BVJHPLDMZKSTIL-UHFFFAOYSA-N 0.000 description 1
- AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 description 1
- JSHASCFKOSDFHY-UHFFFAOYSA-N 1-butylpyrrolidine Chemical compound CCCCN1CCCC1 JSHASCFKOSDFHY-UHFFFAOYSA-N 0.000 description 1
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical compound CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 description 1
- HLNRRPIYRBBHSQ-UHFFFAOYSA-N 1-propylpyrrolidine Chemical compound CCCN1CCCC1 HLNRRPIYRBBHSQ-UHFFFAOYSA-N 0.000 description 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- FOTZPUNKEDWGDE-UHFFFAOYSA-N 2,2-dimethyl-1-phenylpropane-1,3-diol;phosphorous acid Chemical compound OP(O)O.OCC(C)(C)C(O)C1=CC=CC=C1 FOTZPUNKEDWGDE-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- XPUJOEOXHUYRPJ-UHFFFAOYSA-N 2,4-ditert-butyl-4-methylcyclohexa-1,5-dien-1-ol Chemical compound CC(C)(C)C1=C(O)C=CC(C)(C(C)(C)C)C1 XPUJOEOXHUYRPJ-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- 125000003456 2,6-dinitrophenyl group Chemical group [H]C1=C([H])C(=C(*)C(=C1[H])[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- WLHYKGXWBWSYKL-UHFFFAOYSA-N 2-(2-bicyclo[2.2.1]heptanylamino)ethanesulfonic acid Chemical class OS(=O)(=O)CCNC1CC2CCC1C2 WLHYKGXWBWSYKL-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- IPRSYPLQDZLFFB-UHFFFAOYSA-N 2-(butylamino)ethanesulfonic acid Chemical compound CCCCNCCS(O)(=O)=O IPRSYPLQDZLFFB-UHFFFAOYSA-N 0.000 description 1
- IHTFXGQZIXARRN-UHFFFAOYSA-N 2-(cyclobutylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCC1 IHTFXGQZIXARRN-UHFFFAOYSA-N 0.000 description 1
- TXQULGABUTXOJD-UHFFFAOYSA-N 2-(cycloheptylamino)ethanesulfonic acid Chemical class OS(=O)(=O)CCNC1CCCCCC1 TXQULGABUTXOJD-UHFFFAOYSA-N 0.000 description 1
- GNXXUKIVYFCOND-UHFFFAOYSA-N 2-(cyclooctylamino)ethanesulfonic acid Chemical class OS(=O)(=O)CCNC1CCCCCCC1 GNXXUKIVYFCOND-UHFFFAOYSA-N 0.000 description 1
- ATJAONBLORCPED-UHFFFAOYSA-N 2-(cyclopentylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCCC1 ATJAONBLORCPED-UHFFFAOYSA-N 0.000 description 1
- IVJULNTWOMZJSH-UHFFFAOYSA-N 2-(cyclopropylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CC1 IVJULNTWOMZJSH-UHFFFAOYSA-N 0.000 description 1
- SGSMPWTZYGTIEA-UHFFFAOYSA-N 2-(ethylamino)ethanesulfonic acid Chemical compound CCNCCS(O)(=O)=O SGSMPWTZYGTIEA-UHFFFAOYSA-N 0.000 description 1
- BQWOCTACSPAIGA-UHFFFAOYSA-N 2-(hexylamino)ethanesulfonic acid Chemical compound CCCCCCNCCS(O)(=O)=O BQWOCTACSPAIGA-UHFFFAOYSA-N 0.000 description 1
- XAOQXCKCGLMEHV-UHFFFAOYSA-N 2-(octylamino)ethanesulfonic acid Chemical compound CCCCCCCCNCCS(O)(=O)=O XAOQXCKCGLMEHV-UHFFFAOYSA-N 0.000 description 1
- QDLZTFHRTIQSKV-UHFFFAOYSA-N 2-(pentylamino)ethanesulfonic acid Chemical compound CCCCCNCCS(O)(=O)=O QDLZTFHRTIQSKV-UHFFFAOYSA-N 0.000 description 1
- OGNAKBARWHFHDS-UHFFFAOYSA-N 2-(propylamino)ethanesulfonic acid Chemical compound CCCNCCS(O)(=O)=O OGNAKBARWHFHDS-UHFFFAOYSA-N 0.000 description 1
- PGYSZIVTMWVKPT-UHFFFAOYSA-N 2-(tert-butylamino)ethanesulfonic acid Chemical compound CC(C)(C)NCCS(O)(=O)=O PGYSZIVTMWVKPT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FKRKNAFZAFWGSA-UHFFFAOYSA-N 2-[(1-methylcyclohexyl)amino]ethanesulfonic acid Chemical class CC1(CCCCC1)NCCS(=O)(=O)O FKRKNAFZAFWGSA-UHFFFAOYSA-N 0.000 description 1
- DYFOFRFQRHBEMJ-UHFFFAOYSA-N 2-[(2,3-dimethylcyclohexyl)amino]ethanesulfonic acid Chemical class CC1C(CCCC1C)NCCS(=O)(=O)O DYFOFRFQRHBEMJ-UHFFFAOYSA-N 0.000 description 1
- UMBZPBDRFIPZAP-UHFFFAOYSA-N 2-[(3,5-dimethyl-1-adamantyl)amino]ethanesulfonic acid Chemical compound CC12CC3(CC(CC(C1)(C3)C)C2)NCCS(=O)(=O)O UMBZPBDRFIPZAP-UHFFFAOYSA-N 0.000 description 1
- HYXXUVLQEYGVDO-UHFFFAOYSA-N 2-[(4-tert-butylcyclohexyl)amino]ethanesulfonic acid Chemical class C(C)(C)(C)C1CCC(CC1)NCCS(=O)(=O)O HYXXUVLQEYGVDO-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- ZJYVOSGUICQZHC-UHFFFAOYSA-N 2-butyl-2-ethyl-1-(2,4,6-tritert-butylphenyl)propane-1,3-diol;phosphorous acid Chemical class OP(O)O.CCCCC(CC)(CO)C(O)C1=C(C(C)(C)C)C=C(C(C)(C)C)C=C1C(C)(C)C ZJYVOSGUICQZHC-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- ZHASWUBDRYYWLD-UHFFFAOYSA-N 2-hydroxyacetic acid;molybdenum Chemical compound [Mo].OCC(O)=O ZHASWUBDRYYWLD-UHFFFAOYSA-N 0.000 description 1
- ULHLNVIDIVAORK-UHFFFAOYSA-N 2-hydroxybutanedioic acid Chemical compound OC(=O)C(O)CC(O)=O.OC(=O)C(O)CC(O)=O ULHLNVIDIVAORK-UHFFFAOYSA-N 0.000 description 1
- UGMXSALAXHCCDP-UHFFFAOYSA-N 2-methyl-3-(methylamino)propane-1-sulfonic acid Chemical compound CNCC(CS(=O)(=O)O)C UGMXSALAXHCCDP-UHFFFAOYSA-N 0.000 description 1
- OQYQEKUXSCCFCA-UHFFFAOYSA-N 2-methyl-3-(octylamino)propane-1-sulfonic acid Chemical compound CCCCCCCCNCC(C)CS(O)(=O)=O OQYQEKUXSCCFCA-UHFFFAOYSA-N 0.000 description 1
- LVIANYIBYXYRBA-UHFFFAOYSA-N 2-methyl-3-(pentylamino)propane-1-sulfonic acid Chemical compound CCCCCNCC(C)CS(O)(=O)=O LVIANYIBYXYRBA-UHFFFAOYSA-N 0.000 description 1
- GOSGYTODOAFBJP-UHFFFAOYSA-N 2-methyl-3-(propan-2-ylamino)propane-1-sulfonic acid Chemical compound C(C)(C)NCC(CS(=O)(=O)O)C GOSGYTODOAFBJP-UHFFFAOYSA-N 0.000 description 1
- VZWLCYQTONSSLN-UHFFFAOYSA-N 2-methyl-3-(propylamino)propane-1-sulfonic acid Chemical compound C(CC)NCC(CS(=O)(=O)O)C VZWLCYQTONSSLN-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- FKOZPUORKCHONH-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid Chemical class CC(C)CS(O)(=O)=O FKOZPUORKCHONH-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- FZIPCQLKPTZZIM-UHFFFAOYSA-N 2-oxidanylpropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O FZIPCQLKPTZZIM-UHFFFAOYSA-N 0.000 description 1
- IAVHKMVGTPXJIC-UHFFFAOYSA-N 2-phenylamino-ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1=CC=CC=C1 IAVHKMVGTPXJIC-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 description 1
- XYYXDARQOHWBPO-UHFFFAOYSA-N 3,5-dimethyl-1h-1,2,4-triazole Chemical compound CC1=NNC(C)=N1 XYYXDARQOHWBPO-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 1
- YLUZWKKWWSCRSR-UHFFFAOYSA-N 3,9-bis(8-methylnonoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCC(C)C)OCC21COP(OCCCCCCCC(C)C)OC2 YLUZWKKWWSCRSR-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- UGPGIXUYVCNPIQ-UHFFFAOYSA-N 3-(1-adamantylamino)-2-methylpropane-1-sulfonic acid Chemical compound C12(CC3CC(CC(C1)C3)C2)NCC(CS(=O)(=O)O)C UGPGIXUYVCNPIQ-UHFFFAOYSA-N 0.000 description 1
- PTEWIIWNVNZSEH-UHFFFAOYSA-N 3-(1-adamantylamino)butane-1-sulfonic acid Chemical compound C12(CC3CC(CC(C1)C3)C2)NC(CCS(=O)(=O)O)C PTEWIIWNVNZSEH-UHFFFAOYSA-N 0.000 description 1
- RSVQKBYTFFJXRP-UHFFFAOYSA-N 3-(1-adamantylamino)propane-1-sulfonic acid Chemical compound C1C(C2)CC3CC2CC1(NCCCS(=O)(=O)O)C3 RSVQKBYTFFJXRP-UHFFFAOYSA-N 0.000 description 1
- DHDHPQFIHKUAKH-UHFFFAOYSA-N 3-(2-bicyclo[2.2.1]heptanylamino)butane-1-sulfonic acid Chemical compound C12C(CC(CC1)C2)NC(CCS(=O)(=O)O)C DHDHPQFIHKUAKH-UHFFFAOYSA-N 0.000 description 1
- CSWQWURIPDDZMR-UHFFFAOYSA-N 3-(2-bicyclo[2.2.1]heptanylamino)butane-2-sulfonic acid Chemical compound C12C(CC(CC1)C2)NC(C(C)S(=O)(=O)O)C CSWQWURIPDDZMR-UHFFFAOYSA-N 0.000 description 1
- WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 description 1
- QSVVTMLHGXCUCD-UHFFFAOYSA-N 3-(3-bicyclo[2.2.1]heptanylamino)-2-methylpropane-1-sulfonic acid Chemical compound C1CC2C(NCC(C)CS(O)(=O)=O)CC1C2 QSVVTMLHGXCUCD-UHFFFAOYSA-N 0.000 description 1
- BGZJQENTTIDTBU-UHFFFAOYSA-N 3-(3-bicyclo[2.2.1]heptanylamino)propane-1-sulfonic acid Chemical compound C1CC2C(NCCCS(=O)(=O)O)CC1C2 BGZJQENTTIDTBU-UHFFFAOYSA-N 0.000 description 1
- MPAWFJFGDBHQAP-UHFFFAOYSA-N 3-(butylamino)butane-1-sulfonic acid Chemical compound C(CCC)NC(CCS(=O)(=O)O)C MPAWFJFGDBHQAP-UHFFFAOYSA-N 0.000 description 1
- WXESAUYENKUDLP-UHFFFAOYSA-N 3-(butylamino)butane-2-sulfonic acid Chemical compound C(CCC)NC(C(C)S(=O)(=O)O)C WXESAUYENKUDLP-UHFFFAOYSA-N 0.000 description 1
- ZZVWIMPMMGCOMR-UHFFFAOYSA-N 3-(butylamino)propane-1-sulfonic acid Chemical compound CCCCNCCCS(O)(=O)=O ZZVWIMPMMGCOMR-UHFFFAOYSA-N 0.000 description 1
- MTJTXDMWJVEXIW-UHFFFAOYSA-N 3-(cyclobutylamino)butane-1-sulfonic acid Chemical compound C1(CCC1)NC(CCS(=O)(=O)O)C MTJTXDMWJVEXIW-UHFFFAOYSA-N 0.000 description 1
- JOCPZGDKSZMCIA-UHFFFAOYSA-N 3-(cyclobutylamino)butane-2-sulfonic acid Chemical compound C1(CCC1)NC(C(C)S(=O)(=O)O)C JOCPZGDKSZMCIA-UHFFFAOYSA-N 0.000 description 1
- UUYOVYOGEFJUCD-UHFFFAOYSA-N 3-(cycloheptylamino)-2-methylpropane-1-sulfonic acid Chemical compound C1(CCCCCC1)NCC(CS(=O)(=O)O)C UUYOVYOGEFJUCD-UHFFFAOYSA-N 0.000 description 1
- CVJJIDGXUAMYJJ-UHFFFAOYSA-N 3-(cycloheptylamino)butane-1-sulfonic acid Chemical compound C1(CCCCCC1)NC(CCS(=O)(=O)O)C CVJJIDGXUAMYJJ-UHFFFAOYSA-N 0.000 description 1
- PGMHFKBTXSFJAV-UHFFFAOYSA-N 3-(cycloheptylamino)butane-2-sulfonic acid Chemical compound C1(CCCCCC1)NC(C(C)S(=O)(=O)O)C PGMHFKBTXSFJAV-UHFFFAOYSA-N 0.000 description 1
- DZPHBMKZLYOOQY-UHFFFAOYSA-N 3-(cycloheptylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNC1CCCCCC1 DZPHBMKZLYOOQY-UHFFFAOYSA-N 0.000 description 1
- SEAUUAIDZIGZEG-UHFFFAOYSA-N 3-(cyclohexylamino)-2-methylpropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)CNC1CCCCC1 SEAUUAIDZIGZEG-UHFFFAOYSA-N 0.000 description 1
- NEPFKUSOPUOQDF-UHFFFAOYSA-N 3-(cyclohexylamino)butane-1-sulfonic acid Chemical compound OS(=O)(=O)CCC(C)NC1CCCCC1 NEPFKUSOPUOQDF-UHFFFAOYSA-N 0.000 description 1
- GPURUXWWRONKRO-UHFFFAOYSA-N 3-(cyclohexylamino)butane-2-sulfonic acid Chemical compound C1(CCCCC1)NC(C(C)S(=O)(=O)O)C GPURUXWWRONKRO-UHFFFAOYSA-N 0.000 description 1
- VYYRSTOTUMFOSY-UHFFFAOYSA-N 3-(cyclooctylamino)butane-1-sulfonic acid Chemical compound C1(CCCCCCC1)NC(CCS(=O)(=O)O)C VYYRSTOTUMFOSY-UHFFFAOYSA-N 0.000 description 1
- FAABINCSKWFERE-UHFFFAOYSA-N 3-(cyclooctylamino)butane-2-sulfonic acid Chemical compound C1(CCCCCCC1)NC(C(C)S(=O)(=O)O)C FAABINCSKWFERE-UHFFFAOYSA-N 0.000 description 1
- LQYVIQIKJKNZQH-UHFFFAOYSA-N 3-(cyclooctylamino)propane-1-sulfonic acid Chemical compound C1(CCCCCCC1)NCCCS(=O)(=O)O LQYVIQIKJKNZQH-UHFFFAOYSA-N 0.000 description 1
- DAEVNVROFIBMKJ-UHFFFAOYSA-N 3-(cyclopentylamino)-2-methylpropane-1-sulfonic acid Chemical compound C1(CCCC1)NCC(CS(=O)(=O)O)C DAEVNVROFIBMKJ-UHFFFAOYSA-N 0.000 description 1
- CCXJZCWGYJMXGP-UHFFFAOYSA-N 3-(cyclopentylamino)butane-1-sulfonic acid Chemical compound C1(CCCC1)NC(CCS(=O)(=O)O)C CCXJZCWGYJMXGP-UHFFFAOYSA-N 0.000 description 1
- IPWZUNQZPBNLCE-UHFFFAOYSA-N 3-(cyclopentylamino)butane-2-sulfonic acid Chemical compound C1(CCCC1)NC(C(C)S(=O)(=O)O)C IPWZUNQZPBNLCE-UHFFFAOYSA-N 0.000 description 1
- NJPZSYXMHIXIQP-UHFFFAOYSA-N 3-(cyclopropylamino)-2-methylpropane-1-sulfonic acid Chemical compound C1(CC1)NCC(CS(=O)(=O)O)C NJPZSYXMHIXIQP-UHFFFAOYSA-N 0.000 description 1
- KAGXXGDONSKEJH-UHFFFAOYSA-N 3-(cyclopropylamino)butane-1-sulfonic acid Chemical compound C1(CC1)NC(CCS(=O)(=O)O)C KAGXXGDONSKEJH-UHFFFAOYSA-N 0.000 description 1
- VLNQTLQHIORDHY-UHFFFAOYSA-N 3-(cyclopropylamino)butane-2-sulfonic acid Chemical compound C1(CC1)NC(C(C)S(=O)(=O)O)C VLNQTLQHIORDHY-UHFFFAOYSA-N 0.000 description 1
- VLCUXLMAJCSBIM-UHFFFAOYSA-N 3-(cyclopropylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNC1CC1 VLCUXLMAJCSBIM-UHFFFAOYSA-N 0.000 description 1
- GSOGHAJXJYZNHV-UHFFFAOYSA-N 3-(ethylamino)-2-methylpropane-1-sulfonic acid Chemical compound C(C)NCC(CS(=O)(=O)O)C GSOGHAJXJYZNHV-UHFFFAOYSA-N 0.000 description 1
- KIGZUEMRMZAUDJ-UHFFFAOYSA-N 3-(ethylamino)butane-1-sulfonic acid Chemical compound C(C)NC(CCS(=O)(=O)O)C KIGZUEMRMZAUDJ-UHFFFAOYSA-N 0.000 description 1
- PVVYVJIWIDEXND-UHFFFAOYSA-N 3-(ethylamino)butane-2-sulfonic acid Chemical compound C(C)NC(C(C)S(=O)(=O)O)C PVVYVJIWIDEXND-UHFFFAOYSA-N 0.000 description 1
- CTTMFPGEHCZZIR-UHFFFAOYSA-N 3-(ethylamino)propane-1-sulfonic acid Chemical compound CCNCCCS(O)(=O)=O CTTMFPGEHCZZIR-UHFFFAOYSA-N 0.000 description 1
- ASWWXTCHBQQUIP-UHFFFAOYSA-N 3-(hexylamino)-2-methylpropane-1-sulfonic acid Chemical compound C(CCCCC)NCC(CS(=O)(=O)O)C ASWWXTCHBQQUIP-UHFFFAOYSA-N 0.000 description 1
- OGKHULDSEMLJAC-UHFFFAOYSA-N 3-(hexylamino)butane-1-sulfonic acid Chemical compound C(CCCCC)NC(CCS(=O)(=O)O)C OGKHULDSEMLJAC-UHFFFAOYSA-N 0.000 description 1
- DPVCLNGXIBXTQL-UHFFFAOYSA-N 3-(hexylamino)butane-2-sulfonic acid Chemical compound C(CCCCC)NC(C(C)S(=O)(=O)O)C DPVCLNGXIBXTQL-UHFFFAOYSA-N 0.000 description 1
- IHLZVTOFYPZJSZ-UHFFFAOYSA-N 3-(hexylamino)propane-1-sulfonic acid Chemical compound CCCCCCNCCCS(O)(=O)=O IHLZVTOFYPZJSZ-UHFFFAOYSA-N 0.000 description 1
- QJJMSDNKJDUMTA-UHFFFAOYSA-N 3-(methylamino)butane-1-sulfonic acid Chemical compound CNC(CCS(=O)(=O)O)C QJJMSDNKJDUMTA-UHFFFAOYSA-N 0.000 description 1
- WIABHOQEYLWTRX-UHFFFAOYSA-N 3-(methylamino)butane-2-sulfonic acid Chemical compound CNC(C)C(C)S(O)(=O)=O WIABHOQEYLWTRX-UHFFFAOYSA-N 0.000 description 1
- ZLBZKWPINAVJOK-UHFFFAOYSA-N 3-(methylamino)propane-1-sulfonic acid Chemical compound CNCCCS(O)(=O)=O ZLBZKWPINAVJOK-UHFFFAOYSA-N 0.000 description 1
- RNSBZFSVQNWUGT-UHFFFAOYSA-N 3-(octylamino)butane-1-sulfonic acid Chemical compound C(CCCCCCC)NC(CCS(=O)(=O)O)C RNSBZFSVQNWUGT-UHFFFAOYSA-N 0.000 description 1
- WKQOZDNCWMDULR-UHFFFAOYSA-N 3-(octylamino)butane-2-sulfonic acid Chemical compound C(CCCCCCC)NC(C(C)S(=O)(=O)O)C WKQOZDNCWMDULR-UHFFFAOYSA-N 0.000 description 1
- MHWJLKIZOLWXQZ-UHFFFAOYSA-N 3-(octylamino)propane-1-sulfonic acid Chemical compound CCCCCCCCNCCCS(O)(=O)=O MHWJLKIZOLWXQZ-UHFFFAOYSA-N 0.000 description 1
- PKMNTKNSRCUHJK-UHFFFAOYSA-N 3-(pentylamino)butane-1-sulfonic acid Chemical compound C(CCCC)NC(CCS(=O)(=O)O)C PKMNTKNSRCUHJK-UHFFFAOYSA-N 0.000 description 1
- AECWOXDWIOLSAP-UHFFFAOYSA-N 3-(pentylamino)butane-2-sulfonic acid Chemical compound C(CCCC)NC(C(C)S(=O)(=O)O)C AECWOXDWIOLSAP-UHFFFAOYSA-N 0.000 description 1
- LSSRWPPRLILFPI-UHFFFAOYSA-N 3-(pentylamino)propane-1-sulfonic acid Chemical compound CCCCCNCCCS(O)(=O)=O LSSRWPPRLILFPI-UHFFFAOYSA-N 0.000 description 1
- NYLUYMWPXIIXDX-UHFFFAOYSA-N 3-(phenylazaniumyl)propane-1-sulfonate Chemical compound OS(=O)(=O)CCCNC1=CC=CC=C1 NYLUYMWPXIIXDX-UHFFFAOYSA-N 0.000 description 1
- QSRLVGJVIAPCPD-UHFFFAOYSA-N 3-(propan-2-ylamino)butane-1-sulfonic acid Chemical compound C(C)(C)NC(CCS(=O)(=O)O)C QSRLVGJVIAPCPD-UHFFFAOYSA-N 0.000 description 1
- GNHGBJDFZPUOJF-UHFFFAOYSA-N 3-(propan-2-ylamino)butane-2-sulfonic acid Chemical compound C(C)(C)NC(C(C)S(=O)(=O)O)C GNHGBJDFZPUOJF-UHFFFAOYSA-N 0.000 description 1
- BLYGFIYCEOLGRR-UHFFFAOYSA-N 3-(propylamino)propane-1-sulfonic acid Chemical compound CCCNCCCS(O)(=O)=O BLYGFIYCEOLGRR-UHFFFAOYSA-N 0.000 description 1
- AHLOMNKKKGQKLD-UHFFFAOYSA-N 3-(tert-butylamino)-2-methylpropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)CNC(C)(C)C AHLOMNKKKGQKLD-UHFFFAOYSA-N 0.000 description 1
- UWDASXYHGLZLGB-UHFFFAOYSA-N 3-(tert-butylamino)butane-1-sulfonic acid Chemical compound C(C)(C)(C)NC(CCS(=O)(=O)O)C UWDASXYHGLZLGB-UHFFFAOYSA-N 0.000 description 1
- RCCGPZOHGLGUAV-UHFFFAOYSA-N 3-(tert-butylamino)butane-2-sulfonic acid Chemical compound C(C)(C)(C)NC(C(C)S(=O)(=O)O)C RCCGPZOHGLGUAV-UHFFFAOYSA-N 0.000 description 1
- AJOMXCNJGRAIHS-UHFFFAOYSA-N 3-(tert-butylamino)propane-1-sulfonic acid Chemical compound CC(C)(C)NCCCS(O)(=O)=O AJOMXCNJGRAIHS-UHFFFAOYSA-N 0.000 description 1
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 1
- AYTMPILMYIDVTD-UHFFFAOYSA-N 3-[(1-methylcyclohexyl)amino]butane-1-sulfonic acid Chemical class CC1(CCCCC1)NC(CCS(=O)(=O)O)C AYTMPILMYIDVTD-UHFFFAOYSA-N 0.000 description 1
- DOIIZBVCCJRXDX-UHFFFAOYSA-N 3-[(1-methylcyclohexyl)amino]butane-2-sulfonic acid Chemical class CC1(CCCCC1)NC(C(C)S(=O)(=O)O)C DOIIZBVCCJRXDX-UHFFFAOYSA-N 0.000 description 1
- SIOWLTTVQDAONL-UHFFFAOYSA-N 3-[(1-methylcyclohexyl)amino]propane-1-sulfonic acid Chemical class OS(=O)(=O)CCCNC1(C)CCCCC1 SIOWLTTVQDAONL-UHFFFAOYSA-N 0.000 description 1
- JETXYLXFMOCXME-UHFFFAOYSA-N 3-[(2,3-dimethylcyclohexyl)amino]-2-methylpropane-1-sulfonic acid Chemical class CC1C(CCCC1C)NCC(CS(=O)(=O)O)C JETXYLXFMOCXME-UHFFFAOYSA-N 0.000 description 1
- ZGHYMUNAOCEJMY-UHFFFAOYSA-N 3-[(2,3-dimethylcyclohexyl)amino]butane-1-sulfonic acid Chemical class CC1C(CCCC1C)NC(CCS(=O)(=O)O)C ZGHYMUNAOCEJMY-UHFFFAOYSA-N 0.000 description 1
- ZVNZWUZRAWMFPW-UHFFFAOYSA-N 3-[(2,3-dimethylcyclohexyl)amino]butane-2-sulfonic acid Chemical class CC1C(CCCC1C)NC(C(C)S(=O)(=O)O)C ZVNZWUZRAWMFPW-UHFFFAOYSA-N 0.000 description 1
- OYUQLOJSGLQOEI-UHFFFAOYSA-N 3-[(2,3-dimethylcyclohexyl)amino]propane-1-sulfonic acid Chemical class CC1CCCC(NCCCS(O)(=O)=O)C1C OYUQLOJSGLQOEI-UHFFFAOYSA-N 0.000 description 1
- JACTVYBCEXDIEW-UHFFFAOYSA-N 3-[(3,5-dimethyl-1-adamantyl)amino]-2-methylpropane-1-sulfonic acid Chemical compound CC12CC3(CC(CC(C1)(C3)C)C2)NCC(CS(=O)(=O)O)C JACTVYBCEXDIEW-UHFFFAOYSA-N 0.000 description 1
- ABIDZNKDRVZQJY-UHFFFAOYSA-N 3-[(3,5-dimethyl-1-adamantyl)amino]butane-1-sulfonic acid Chemical compound CC12CC3(CC(CC(C1)(C3)C)C2)NC(CCS(=O)(=O)O)C ABIDZNKDRVZQJY-UHFFFAOYSA-N 0.000 description 1
- QSYCBLALGCONRK-UHFFFAOYSA-N 3-[(3,5-dimethyl-1-adamantyl)amino]butane-2-sulfonic acid Chemical compound CC12CC3(CC(CC(C1)(C3)C)C2)NC(C(C)S(=O)(=O)O)C QSYCBLALGCONRK-UHFFFAOYSA-N 0.000 description 1
- AKJQFHDUQIWSSK-UHFFFAOYSA-N 3-[(3,5-dimethyl-1-adamantyl)amino]propane-1-sulfonic acid Chemical compound C1C(C2)CC3(C)CC1(C)CC2(NCCCS(O)(=O)=O)C3 AKJQFHDUQIWSSK-UHFFFAOYSA-N 0.000 description 1
- BYVRWZFDRORAAF-UHFFFAOYSA-N 3-[(4-tert-butylcyclohexyl)amino]-2-methylpropane-1-sulfonic acid Chemical compound C(C)(C)(C)C1CCC(CC1)NCC(CS(=O)(=O)O)C BYVRWZFDRORAAF-UHFFFAOYSA-N 0.000 description 1
- RYRAMOIGODOSOE-UHFFFAOYSA-N 3-[(4-tert-butylcyclohexyl)amino]butane-1-sulfonic acid Chemical compound C(C)(C)(C)C1CCC(CC1)NC(CCS(=O)(=O)O)C RYRAMOIGODOSOE-UHFFFAOYSA-N 0.000 description 1
- CRIYHVLYGOTMJI-UHFFFAOYSA-N 3-[(4-tert-butylcyclohexyl)amino]butane-2-sulfonic acid Chemical compound C(C)(C)(C)C1CCC(CC1)NC(C(C)S(=O)(=O)O)C CRIYHVLYGOTMJI-UHFFFAOYSA-N 0.000 description 1
- SWRPWTYCIVKFLP-UHFFFAOYSA-N 3-[(4-tert-butylcyclohexyl)amino]propane-1-sulfonic acid Chemical compound CC(C)(C)C1CCC(NCCCS(O)(=O)=O)CC1 SWRPWTYCIVKFLP-UHFFFAOYSA-N 0.000 description 1
- QOHOVCGREXOMGH-UHFFFAOYSA-N 3-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=CC(N)=CC(S(O)(=O)=O)=C21 QOHOVCGREXOMGH-UHFFFAOYSA-N 0.000 description 1
- YERLJVADNWILOY-UHFFFAOYSA-N 3-anilino-2-methylpropane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)CNC1=CC=CC=C1 YERLJVADNWILOY-UHFFFAOYSA-N 0.000 description 1
- KBVORZUUIVLTEA-UHFFFAOYSA-N 3-anilinobutane-1-sulfonic acid Chemical compound OS(=O)(=O)CCC(C)NC1=CC=CC=C1 KBVORZUUIVLTEA-UHFFFAOYSA-N 0.000 description 1
- KFVMPDZTXQFJBO-UHFFFAOYSA-N 3-anilinobutane-2-sulfonic acid Chemical compound N(C1=CC=CC=C1)C(C(C)S(=O)(=O)O)C KFVMPDZTXQFJBO-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- YERNQLVULLQTRA-UHFFFAOYSA-N 4-(1-adamantylamino)butane-1-sulfonic acid Chemical compound C1C(C2)CC3CC2CC1(NCCCCS(=O)(=O)O)C3 YERNQLVULLQTRA-UHFFFAOYSA-N 0.000 description 1
- VJLMWAWFCQRRFS-UHFFFAOYSA-N 4-(3-bicyclo[2.2.1]heptanylamino)butane-1-sulfonic acid Chemical compound C1CC2C(NCCCCS(=O)(=O)O)CC1C2 VJLMWAWFCQRRFS-UHFFFAOYSA-N 0.000 description 1
- YGAMQWKKHMZWHR-UHFFFAOYSA-N 4-(cyclobutylamino)butane-1-sulfonic acid Chemical compound C1(CCC1)NCCCCS(=O)(=O)O YGAMQWKKHMZWHR-UHFFFAOYSA-N 0.000 description 1
- YYRGOPLUGHFFKH-UHFFFAOYSA-N 4-(cycloheptylamino)butane-1-sulfonic acid Chemical compound C1(CCCCCC1)NCCCCS(=O)(=O)O YYRGOPLUGHFFKH-UHFFFAOYSA-N 0.000 description 1
- ZCWLKHNFRUFREW-UHFFFAOYSA-N 4-(cyclooctylamino)butane-1-sulfonic acid Chemical compound C1(CCCCCCC1)NCCCCS(=O)(=O)O ZCWLKHNFRUFREW-UHFFFAOYSA-N 0.000 description 1
- SAONOWFMRCHXLR-UHFFFAOYSA-N 4-(cyclopentylamino)butane-1-sulfonic acid Chemical compound C1(CCCC1)NCCCCS(=O)(=O)O SAONOWFMRCHXLR-UHFFFAOYSA-N 0.000 description 1
- BKYBNVBMIATFJY-UHFFFAOYSA-N 4-(cyclopropylamino)butane-1-sulfonic acid Chemical compound C1(CC1)NCCCCS(=O)(=O)O BKYBNVBMIATFJY-UHFFFAOYSA-N 0.000 description 1
- KZHUATYDDMJYAJ-UHFFFAOYSA-N 4-(ethylamino)butane-1-sulfonic acid Chemical compound CCNCCCCS(O)(=O)=O KZHUATYDDMJYAJ-UHFFFAOYSA-N 0.000 description 1
- FKTGOQVJIDMIBX-UHFFFAOYSA-N 4-(hexylamino)butane-1-sulfonic acid Chemical compound C(CCCCC)NCCCCS(=O)(=O)O FKTGOQVJIDMIBX-UHFFFAOYSA-N 0.000 description 1
- GGYUPZCMPLDQNM-UHFFFAOYSA-N 4-(methylazaniumyl)butane-1-sulfonate Chemical compound CNCCCCS(O)(=O)=O GGYUPZCMPLDQNM-UHFFFAOYSA-N 0.000 description 1
- BGCMJBRUWVPTBI-UHFFFAOYSA-N 4-(octylamino)butane-1-sulfonic acid Chemical compound CCCCCCCCNCCCCS(O)(=O)=O BGCMJBRUWVPTBI-UHFFFAOYSA-N 0.000 description 1
- QLPWUAQEZGAKFE-UHFFFAOYSA-N 4-(pentylamino)butane-1-sulfonic acid Chemical compound C(CCCC)NCCCCS(=O)(=O)O QLPWUAQEZGAKFE-UHFFFAOYSA-N 0.000 description 1
- QGNAQMRKVPZNSP-UHFFFAOYSA-N 4-(tert-butylamino)butane-1-sulfonic acid Chemical compound CC(C)(C)NCCCCS(O)(=O)=O QGNAQMRKVPZNSP-UHFFFAOYSA-N 0.000 description 1
- VXRUNWORZJNBTG-UHFFFAOYSA-N 4-[(1-methylcyclohexyl)amino]butane-1-sulfonic acid Chemical class CC1(CCCCC1)NCCCCS(=O)(=O)O VXRUNWORZJNBTG-UHFFFAOYSA-N 0.000 description 1
- PFVPWPRMZJYQOK-UHFFFAOYSA-N 4-[(2,3-dimethylcyclohexyl)amino]butane-1-sulfonic acid Chemical class CC1C(CCCC1C)NCCCCS(=O)(=O)O PFVPWPRMZJYQOK-UHFFFAOYSA-N 0.000 description 1
- YLTZNBLKWSJWOM-UHFFFAOYSA-N 4-[(3,5-dimethyl-1-adamantyl)amino]butane-1-sulfonic acid Chemical compound CC12CC3(CC(CC(C1)(C3)C)C2)NCCCCS(=O)(=O)O YLTZNBLKWSJWOM-UHFFFAOYSA-N 0.000 description 1
- MJTKSKBZPAOWLZ-UHFFFAOYSA-N 4-[(4-tert-butylcyclohexyl)amino]butane-1-sulfonic acid Chemical compound C(C)(C)(C)C1CCC(CC1)NCCCCS(=O)(=O)O MJTKSKBZPAOWLZ-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 1
- NHQAUSOKYWFWHO-UHFFFAOYSA-N 4-aminobutane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)CCN NHQAUSOKYWFWHO-UHFFFAOYSA-N 0.000 description 1
- FAILACZZGUACOQ-UHFFFAOYSA-N 4-anilinobutane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCCNC1=CC=CC=C1 FAILACZZGUACOQ-UHFFFAOYSA-N 0.000 description 1
- KNILZINKISHVIQ-UHFFFAOYSA-N 4-azaniumylbutane-1-sulfonate Chemical compound NCCCCS(O)(=O)=O KNILZINKISHVIQ-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- FDHGUCPWMSEFHX-UHFFFAOYSA-N 4-butan-2-ylmorpholine Chemical compound CCC(C)N1CCOCC1 FDHGUCPWMSEFHX-UHFFFAOYSA-N 0.000 description 1
- LMRKVKPRHROQRR-UHFFFAOYSA-N 4-butylmorpholine Chemical compound CCCCN1CCOCC1 LMRKVKPRHROQRR-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical class CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- NMILGIZTAZXMTM-UHFFFAOYSA-N 4-propylmorpholine Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 description 1
- OILJIEKQCVHNMM-UHFFFAOYSA-N 4-tert-butylmorpholine Chemical compound CC(C)(C)N1CCOCC1 OILJIEKQCVHNMM-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- NBPOOCGXISZKSX-UHFFFAOYSA-N 6-methylheptyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)CCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NBPOOCGXISZKSX-UHFFFAOYSA-N 0.000 description 1
- WZRNGGFHDMOCEA-UHFFFAOYSA-N 7-methyloxepan-2-one Chemical compound CC1CCCCC(=O)O1 WZRNGGFHDMOCEA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- YJLYANLCNIKXMG-UHFFFAOYSA-N N-Methyldioctylamine Chemical compound CCCCCCCCN(C)CCCCCCCC YJLYANLCNIKXMG-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- KVXNKFYSHAUJIA-UHFFFAOYSA-N acetic acid;ethoxyethane Chemical compound CC(O)=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BEXMOORQHNTVJZ-UHFFFAOYSA-N amino(oxo)methanesulfonic acid Chemical compound NC(=O)S(O)(=O)=O BEXMOORQHNTVJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical class OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- SMUSIFOACPPWGZ-UHFFFAOYSA-L di(hexadecanoyloxy)tin Chemical class [Sn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O SMUSIFOACPPWGZ-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical group 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- KROZITDVWZMYOC-UHFFFAOYSA-N diethyl 5-aminobenzene-1,3-dicarboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC(N)=CC(C(=O)OCC)=C1 KROZITDVWZMYOC-UHFFFAOYSA-N 0.000 description 1
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical class [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical class [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical class CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- KEZUWFPXSXAUOC-UHFFFAOYSA-N heptyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KEZUWFPXSXAUOC-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- YPQKTLPPOXNDMC-UHFFFAOYSA-N isocyanic acid;methylcyclohexane Chemical compound N=C=O.CC1CCCCC1 YPQKTLPPOXNDMC-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- TXQIZBKYTFVWRG-UHFFFAOYSA-N n,n,2-triethylhexan-1-amine Chemical compound CCCCC(CC)CN(CC)CC TXQIZBKYTFVWRG-UHFFFAOYSA-N 0.000 description 1
- GDHRQDYGUDOEIZ-UHFFFAOYSA-N n,n,2-trimethylpropan-1-amine Chemical compound CC(C)CN(C)C GDHRQDYGUDOEIZ-UHFFFAOYSA-N 0.000 description 1
- DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
- KLVOSHOFGYMCCP-UHFFFAOYSA-N n,n-di(propan-2-yl)butan-1-amine Chemical compound CCCCN(C(C)C)C(C)C KLVOSHOFGYMCCP-UHFFFAOYSA-N 0.000 description 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- PYEQSDANHMLHJJ-UHFFFAOYSA-N n,n-dichloroheptan-1-amine Chemical compound CCCCCCCN(Cl)Cl PYEQSDANHMLHJJ-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- ORSUTASIQKBEFU-UHFFFAOYSA-N n,n-diethylbutan-1-amine Chemical compound CCCCN(CC)CC ORSUTASIQKBEFU-UHFFFAOYSA-N 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- XHDKYWMKOLURNK-UHFFFAOYSA-N n,n-diethylhexan-1-amine Chemical compound CCCCCCN(CC)CC XHDKYWMKOLURNK-UHFFFAOYSA-N 0.000 description 1
- BVUGARXRRGZONH-UHFFFAOYSA-N n,n-diethyloctan-1-amine Chemical compound CCCCCCCCN(CC)CC BVUGARXRRGZONH-UHFFFAOYSA-N 0.000 description 1
- JAOPKYRWYXCGOQ-UHFFFAOYSA-N n,n-dimethyl-1-(4-methylphenyl)methanamine Chemical compound CN(C)CC1=CC=C(C)C=C1 JAOPKYRWYXCGOQ-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 description 1
- ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
- WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical class OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical class O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical compound CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 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 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical class [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Description
A)少なくとも1つのポリイソシアネート成分と、
B)少なくとも1つのアミノ基と少なくとも1つのスルホン酸基とを含む、少なくとも1つのアミノスルホン酸と、
任意に、
C)イソシアネートに対して反応性の少なくとも1つの基を含む、少なくとも1つの非イオン性親水性または疎水性有機化合物と
の反応であって、
D)少なくとも1つの第三級アミンの存在下、および、
任意に、
E)その他の助剤及び添加剤の存在下
での反応を含み、
前記アミノスルホン酸B)の含水率が0.05~1.5重量%であることを特徴とする。
A)少なくとも1つのポリイソシアネート成分と、
B)少なくとも1つのアミノ基と少なくとも1つのスルホン酸基とを含む、少なくとも1つのアミノスルホン酸と
任意に、
C)イソシアネートに対して反応性の少なくとも1つの基を含む、少なくとも1つの非イオン性親水性有機化合物、および/または、イソシアネートに対して反応性の少なくとも1つの基を含む少なくとも1つの疎水性有機化合物と
の反応であって、
D)少なくとも1つの第三級アミンの存在下、
任意に、
E)他の助剤及び添加剤の存在下
での反応を含み、
アミノスルホン酸B)の含水率が0.05~1.5重量%であることを特徴とする製造方法である。
A)少なくとも1つのポリイソシアネート成分と、
B)少なくとも1つのアミノ基および少なくとも1つのスルホン酸基を含む、少なくとも1つのアミノスルホン酸と、
任意に
C)イソシアネートに対して反応性の少なくとも1つの基を含む少なくとも1つの非イオン性親水性有機化合物、および/または、イソシアネートに対して反応性の少なくとも1つの基を含む少なくとも1つの疎水性有機化合物と
の反応であって、
D)少なくとも1つの第三級アミンの存在下、
任意に
E)他の助剤及び添加剤の存在下
での反応を含み、
アミノスルホン酸B)の含水率は0.05~1.5重量%であり、成分A)、成分C)、成分D)及び成分E)の含水率は各々、使用する成分の総量に対して、各々の場合、500重量ppm未満であることを特徴とする。言及した他の全ての実施形態と同様に、出発成分A)、B)、D)、任意にC)および任意にE)を含む反応混合物中の総含水率が0.5重量%未満、特に好ましくは0.2重量%未満、特に好ましくは0.1重量%未満であることも、ここでは非常に特に好ましい。上記の反応混合物は、好ましくは出発成分A)、B)、D)、任意にC)及び任意にE)からなり、総含水率が0.5重量%未満、特に好ましくは0.2重量%未満、特に好ましくは0.1重量%未満である。
(i)本発明に従ってスルホネート基で親水性に変性したポリイソシアネートと、
(ii)例として挙げた種類の未変性ポリイソシアネートと
の混合物からなるからである。
特に明記しない限り、報告されたパーセンテージはすべて重量に基づく。
ポリイソシアネートA)
出発ポリイソシアネートA1)
欧州特許出願公開第330 966号明細書の実施例11に基づくHDIの触媒三量化によって製造されたイソシアヌレート基を含むHDIポリイソシアネートであって、40%の粗混合物中のNCO含水率でのリン酸ジブチルの添加によって反応を停止するように修飾されたもの。次いで、未反応のHDIを温度130℃、圧力0.2mbarで薄膜蒸留により除去した。
NCO官能性: 3.4
モノマーHDI: 0.1%
粘度(23℃): 3,080mPas
色番号(へーゼン): 18
欧州特許出願公開第0003765号明細書の実施例2に従ってIPDIを触媒的に三量化することによって調製された、イソシアヌレート基を含有するIPDIポリイソシアネート。使用した触媒量に基づいて等モル量のリン酸ジブチルを添加し、さらに80℃で30分間撹拌することにより、粗混合物のNCO含水率30.1%で反応を失活させた。次いで、未反応のIPDIを温度170℃、圧力0.3mbarで薄膜蒸留により除去し、得られた固体樹脂を酢酸ブチルで固形分70%まで希釈した。
NCO官能性: 3.3
モノマーHDI: 0.28%
粘度(23℃): 620mPas
色番号(へーゼン): 14
イソシアヌレート基を含むPDIポリイソシアネートであって、ポリイソシアネート成分A2)について国際公開第2016/146579号に記載された方法によってPDIを触媒三量化することによって製造されるもの。使用した触媒量に基づいて等モル量のリン酸ジブチルを添加し、さらに80℃で30分間撹拌することにより、粗混合物のNCO含水率36.7%で反応を失活させた。次いで、未反応のPDIを、温度140℃、圧力0.5mbarで薄膜蒸留により除去した。
NCO官能性: 3.5
モノマーHDI: 0.09%
粘度(23℃): 9850mPas
色番号(へーゼン): 34
使用したアミノスルホン酸は、3-(シクロヘキシルアミノ)プロパンスルホン酸(Sigma-Aldrich Chemie Gmbh,Munich,DE)、供給形態の含水率:1.7%、および4-(シクロヘキシルアミノ)ブタンスルホン酸(Santa Cruz Biotechnology,Inc.,Heidelberg,DE)、供給形態の含水率:4.5%であった。
メトキシポリエチレングリコールMPEG500(Ineos Oxide,Cologne,DE)、水分0.02%。
全ての実施例において使用された第三級アミンは、含水率0.03%のN,N-ジメチルシクロヘキシルアミン(Merck Chemicals GmbH,Darmstadt,DE)であった。
イソシアヌレート基含有出発ポリイソシアネートA1)968.5g(5.01val)を、20.0g(0.09val)の3-(シクロヘキシルアミノ)プロパンスルホン酸(CAPS)、含水率0.03%、11.5g(0.09mol)のジメチルメチルフェノールアミンおよび0.05g(50ppm)の2,6-ジ-tert-ブチル-4-シクロヘキシルと共に、無水窒素下、100℃にて、5:30時間後、スルホネート基を含有する非常に透明なポリイソシアネート混合物が存在するまで撹拌した。室温に冷却し、T5500フィルター層(Seitz)でろ過した後、以下の特性データを測定した。
NCO含有率: 20.6%
NCO官能性: 3.3
粘度(23℃): 6,400mPas
色番号(へーゼン): 22
乳化性(MPS): 731nm
実施例1の実験を、含水率0.15%のCAPSを用いて繰り返した。4:15時間の反応時間後に、スルホネート基を含む透明なポリイソシアネート混合物が得られ、濾過後に以下の特徴的なデータを有した。
NCO含有率: 20.7%
NCO官能性: 3.3
粘度(23℃): 6,440mPas
色番号(へーゼン): 19
乳化性(MPS): 329nm
実施例1および2に記載の方法に従って、種々のポリイソシアネートA)を、異なる含水率のアミノスルホン酸B)を用いて反応させた。下記表1は、重量部での反応バッチの組成および得られた生成物の特性データを示す。
含水率0.03%のジメチルシクロヘキシルアミン50.0gに室温で水1.3gを添加し、混合物を10分間撹拌して均質化した。ジメチルシクロヘキシルアミンの含水率は2.56%であった。
NCO含有率: 20.0%
NCO官能性: 3.3
粘度(23℃): 7,210mPas
色番号(へーゼン): 18
乳化性(MPS): 576nm
Claims (16)
- スルホネート基含有ポリイソシアネートの製造方法であって、
A)少なくとも1つのポリイソシアネート成分と、
B)少なくとも1つのアミノ基と少なくとも1つのスルホン酸基とを含む、少なくとも1つのアミノスルホン酸と、
任意に、
C)イソシアネートに対して反応性の少なくとも1つの基を含む、少なくとも1つの非イオン性親水性または疎水性有機化合物と
の反応であって、
D)少なくとも1つの第三級アミンの存在下、および、
任意に、
E)他の助剤および添加剤の存在下
での反応を含み、
前記アミノスルホン酸B)の含水率が0.05~1.5重量%であり、
前記アミノスルホン酸成分B)が、一般式(II)のアミノ官能性スルホン酸であることを特徴とする、製造方法。
R4およびR5は、互いに組み合わせて、および、任意に1つのさらなる窒素原子または1つの酸素原子と組み合わせて、3~8個の炭素原子を有する脂環式の環または複素環を形成してもよく、これは任意でさらに置換されてもよく、
R6は、炭素原子を2~6個有する直鎖または分岐の脂肪族基である。) - 前記ポリイソシアネート成分A)が、ウレトジオン、イソシアヌレート、アロファネート、ビウレット、イミノオキサジアジンジオンおよび/またはオキサジアジントリオン構造を有するポリイソシアネートであり、
前記構造が、脂肪族および/または脂環式結合イソシアネート基のみを有する、請求項1に記載の製造方法。 - 前記アミノスルホン酸成分B)は、2-イソプロピルアミノエタン-1-スルホン酸、3-イソプロピルアミノプロパン-1-スルホン酸、4-イソピロピルアミノブタン-1-スルホン酸、2-シクロヘキシルアミノエタン-1-スルホン酸、3-シクロヘキシルアミノプロパン-1-スルホン酸および/または4-シクロヘキシルアミノブタン-1-スルホン酸であることを特徴とする、請求項1または2に記載の製造方法。
- 前記アミノスルホン酸成分B)が、前記成分A)およびB)の総重量に基づいて、0.3~25.0重量%の量で用いられることを特徴とする、請求項1~3のいずれか1項に記載の製造方法。
- 前記アミノスルホン酸成分B)が、前記成分A)およびB)の総重量に基づいて、0.5~15.0重量%の量で用いられることを特徴とする、請求項1~3のいずれか1項に記載の製造方法。
- 前記アミノスルホン酸成分B)が、前記成分A)およびB)の総重量に基づいて、1.0~10.0重量%の量で用いられることを特徴とする、請求項1~3のいずれか1項に記載の製造方法。
- 前記非イオン性親水性または疎水性有機化合物C)が、純粋なポリエチレンオキシドポリエーテルアルコールおよび/または混合されたポリアルキレンオキシドポリエーテルアルコールであり、そのアルキレンオキシド単位が、少なくとも70mol%の程度のエチレンオキシド単位、および/または、各々の場合において少なくとも8個の炭素原子を含む脂肪族アルコールもしくは脂肪酸エステルアルコールからなることを特徴とする、請求項1~6のいずれか1項に記載の製造方法。
- 前記第三級アミンD)が、N,N-ジメチルブチルアミン、N,N-ジメチル-2-エチルヘキシルアミン、N,N-ジエチルメチルアミン、N,N-ジイソプロピルエチルアミン、N,N-ジイソプロピル-2-エチルヘキシルアミン、N,N-ジメチルシクロヘキシルアミン、N,N-ジシクロヘキシルメチルアミン、N-メチルピロリドン、N-メチルピペリジン、N-エチルピペリジン、N-メチルモルホリン、N-エチルモルホリン、N-イソブチルモルホリンまたはこれらの混合物であることを特徴とする、請求項1~7のいずれか1項に記載の製造方法。
- 前記助剤および添加剤E)が、酸化防止剤および/または触媒であることを特徴とする、請求項1~8のいずれか1項に記載の製造方法。
- 前記アミノスルホン酸B)の含水率が、0.1~1.0重量%であることを特徴とする、請求項1~9のいずれか1項に記載の製造方法。
- 前記アミノスルホン酸B)の含水率が、0.15~0.9重量%であることを特徴とする、請求項1~9のいずれか1項に記載の製造方法。
- 前記アミノスルホン酸B)の含水率が、0.2~0.6重量%であることを特徴とする、請求項1~9のいずれか1項に記載の製造方法。
- 請求項1~12のいずれか1項に記載の製造方法によって得ることができるかまたは得られる、スルホネート基含有ポリイソシアネート。
- ポリウレタンプラスチックの生産における出発成分としての、請求項13に記載のスルホネート基含有ポリイソシアネートの使用。
- 請求項13に記載のスルホネート基含有ポリイソシアネートを含む、コーティング組成物。
- 熱の作用によって任意に硬化される、請求項15に記載のコーティング組成物によってコーティングされた基材。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP18169338.3 | 2018-04-25 | ||
EP18169338.3A EP3560974A1 (de) | 2018-04-25 | 2018-04-25 | Ionisch hydrophilierte polyisocyanate, wassergehalt |
PCT/EP2019/060291 WO2019206861A1 (de) | 2018-04-25 | 2019-04-23 | Ionisch hydrophilierte polyisocyanate, wassergehalt |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021521294A JP2021521294A (ja) | 2021-08-26 |
JP7412349B2 true JP7412349B2 (ja) | 2024-01-12 |
Family
ID=62063446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020555347A Active JP7412349B2 (ja) | 2018-04-25 | 2019-04-23 | イオン性親水化ポリイソシアネートの含水率 |
Country Status (6)
Country | Link |
---|---|
US (1) | US11365277B2 (ja) |
EP (3) | EP3560974A1 (ja) |
JP (1) | JP7412349B2 (ja) |
CN (1) | CN112041369B (ja) |
ES (1) | ES2866248T3 (ja) |
WO (1) | WO2019206861A1 (ja) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113924347B (zh) * | 2019-05-29 | 2022-11-01 | 东曹株式会社 | 自乳化型多异氰酸酯组合物、双组分型涂料组合物和涂膜 |
CN115466201B (zh) * | 2021-06-11 | 2024-05-03 | 万华化学集团股份有限公司 | 一种磺酸改性多异氰酸酯及其制备方法 |
EP4190832A1 (en) * | 2021-12-06 | 2023-06-07 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, coating composition and coated substrate |
CN115010902B (zh) * | 2022-06-30 | 2023-08-11 | 万华化学集团股份有限公司 | 一种亲水改性聚异氰酸酯及其制备方法和应用 |
WO2024000342A1 (zh) * | 2022-06-30 | 2024-01-04 | 万华化学集团股份有限公司 | 一种亲水改性聚异氰酸酯及其制备方法和应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003533566A (ja) | 2000-05-18 | 2003-11-11 | バイエル アクチェンゲゼルシャフト | 変性ポリイソシアネート |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1954093C3 (de) | 1968-11-15 | 1978-12-21 | Mobay Chemical Corp., Pittsburgh, Pa. (V.St.A.) | Verfahren zur Herstellung von polymeren organischen Isocyanaten |
US3993614A (en) * | 1969-07-14 | 1976-11-23 | Minnesota Mining And Manufacturing Company | Sulfonated aromatic polyisocyanates and preparation of stable anionic polyurethane or polyurea latices therefor |
US3998870A (en) * | 1969-07-14 | 1976-12-21 | Minnesota Mining And Manufacturing Company | Sulfonated aromatic polyisocyanates and preparation of stable anionic polyurethane or polyurea latices therefor |
US3998871A (en) * | 1969-07-14 | 1976-12-21 | Minnesota Mining And Manufacturing Company | Sulfonated isocyanate compositions |
DE2414413C3 (de) | 1974-03-26 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verwendung von Lösungen von Polyisocyanaten mit Isocyanuratstruktur in Zweikomponenten-Polyurethan-Lacken |
DE2452532C3 (de) | 1974-11-06 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanurat-Struktur |
DE2641380C2 (de) | 1976-09-15 | 1989-11-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanuratstruktur |
DE2806731A1 (de) | 1978-02-17 | 1979-08-23 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
DE3700209A1 (de) | 1987-01-07 | 1988-07-21 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten mit biuretstruktur |
DE3806276A1 (de) | 1988-02-27 | 1989-09-07 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
DE3811350A1 (de) | 1988-04-02 | 1989-10-19 | Bayer Ag | Verfahren zur herstellung von isocyanuratpolyisocyanaten, die nach diesem verfahren erhaltenen verbindungen und ihre verwendung |
DE3814167A1 (de) | 1988-04-27 | 1989-11-09 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
US4929706A (en) * | 1988-11-02 | 1990-05-29 | W. R. Grace & Co.-Conn. | Cell growth enhancers and/or antibody production stimulators comprising chemically modified hydrophilic polyurea-urethane prepolymers and polymers |
DE3900053A1 (de) | 1989-01-03 | 1990-07-12 | Bayer Ag | Verfahren zur herstellung von uretdion- und isocyanuratgruppen aufweisenden polyisocyanaten, die nach diesem verfahren erhaeltlichen polyisocyanate und ihre verwendung in zweikomponenten-polyurethanlacken |
DE3928503A1 (de) | 1989-08-29 | 1991-03-07 | Bayer Ag | Verfahren zur herstellung von loesungen von isocyanuratgruppen aufweisenden polyisocyanaten in lackloesungsmitteln und ihre verwendung |
DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
CN1109677C (zh) * | 1997-06-13 | 2003-05-28 | 三菱化学株式会社 | 氨基苯磺酸衍生物的单水合物及其制备方法 |
EP0959087B1 (de) | 1998-05-22 | 2003-10-15 | Bayer Aktiengesellschaft | Wasserdispergierbare Polyether-modifizierte Polyisocyanatgemische |
DE10043433A1 (de) * | 2000-09-04 | 2002-03-21 | Bayer Ag | Wäßrige 2-K-PUR-Systeme |
JP2004099488A (ja) * | 2002-09-06 | 2004-04-02 | Wako Pure Chem Ind Ltd | アミノアルキルスルホン酸の製造方法及びその塩の塩交換方法 |
DE10260298A1 (de) | 2002-12-20 | 2004-07-01 | Bayer Ag | Hydrophilierte blockierte Polysocyanate |
DE102005053678A1 (de) * | 2005-11-10 | 2007-05-16 | Bayer Materialscience Ag | Hydrophile Polyisocyanatgemische |
DE102005057683A1 (de) * | 2005-12-01 | 2007-06-06 | Basf Ag | Strahlungshärtbare wasserelmulgierbare Polyisocyanate |
DE102005057682A1 (de) * | 2005-12-01 | 2007-06-06 | Basf Ag | Strahlungshärtbare wasserelmulgierbare Polyisocyanate |
JP2007231100A (ja) * | 2006-02-28 | 2007-09-13 | Kansai Paint Co Ltd | 水性表面被覆用組成物 |
GB2450835B (en) * | 2006-04-25 | 2011-03-02 | Kansai Paint Co Ltd | Method for forming multilayer coating film |
DE502008002532D1 (de) | 2007-07-19 | 2011-03-17 | Basf Se | Wasserdispergierbare polyisocyanate |
EP2236531A1 (de) * | 2009-03-31 | 2010-10-06 | Bayer MaterialScience AG | Neue wäßrige 2K PUR-Beschichtungssysteme für verbesserten Korrosionsschutz |
ES2595156T3 (es) * | 2011-04-19 | 2016-12-28 | Covestro Deutschland Ag | Composición de poliisocianato emulsionable en agua que comprende una sustancia fragante con al menos un grupo hidroxilo y/o aldehído |
JP5280580B1 (ja) * | 2012-11-09 | 2013-09-04 | 住化バイエルウレタン株式会社 | 塗装方法およびポリウレタン塗料用硬化剤 |
DE102012218081A1 (de) * | 2012-10-04 | 2014-04-10 | Evonik Industries Ag | Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität |
CN103785326A (zh) * | 2012-10-29 | 2014-05-14 | 罗门哈斯公司 | 阴离子型异氰酸酯化合物及其作为乳化剂的使用 |
CN103788339B (zh) * | 2012-10-29 | 2016-12-21 | 罗门哈斯公司 | 异氰酸酯化合物的混合物及其作为乳化剂的使用 |
CN104448232B (zh) | 2013-09-13 | 2017-12-15 | 万华化学集团股份有限公司 | 一种氨基磺酸改性的多异氰酸酯及其制备方法和用途 |
AU2013402777B2 (en) * | 2013-10-11 | 2017-11-23 | Dow Global Technologies Llc | Polymer mixture, multilayer article containing the same, and process of preparing the multilayer article |
CN104016888A (zh) * | 2014-06-20 | 2014-09-03 | 王代龙 | 一种制备2-氨基乙磺酸的方法 |
US20180155574A1 (en) | 2015-03-16 | 2018-06-07 | Covestro Deutschland Ag | Hydrophilic polyisocyanates based on 1,5-diisocyanatopentane |
WO2017042111A1 (de) * | 2015-09-07 | 2017-03-16 | Basf Se | Wasseremulgierbare isocyanate mit verbesserten eigenschaften |
EP3428207B1 (en) * | 2016-03-09 | 2019-11-13 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, coating composition, aqueous coating composition, and coated substrate |
JP6633218B2 (ja) * | 2016-09-23 | 2020-01-22 | 旭化成株式会社 | ポリイソシアネート組成物、ブロックポリイソシアネート組成物、コーティング組成物、水性コーティング組成物、及びコーティング基材 |
CN109843955B (zh) | 2016-10-11 | 2021-08-06 | 旭化成株式会社 | 多异氰酸酯组合物 |
ES2869941T3 (es) | 2018-04-25 | 2021-10-26 | Covestro Intellectual Property Gmbh & Co Kg | Poliisocianatos hidrofilizados iónicamente y antioxidantes |
-
2018
- 2018-04-25 EP EP18169338.3A patent/EP3560974A1/de active Pending
-
2019
- 2019-04-23 JP JP2020555347A patent/JP7412349B2/ja active Active
- 2019-04-23 EP EP21161413.6A patent/EP3851472B1/de active Active
- 2019-04-23 ES ES19718390T patent/ES2866248T3/es active Active
- 2019-04-23 CN CN201980028085.5A patent/CN112041369B/zh active Active
- 2019-04-23 WO PCT/EP2019/060291 patent/WO2019206861A1/de unknown
- 2019-04-23 EP EP19718390.8A patent/EP3724251B2/de active Active
- 2019-04-23 US US17/048,716 patent/US11365277B2/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003533566A (ja) | 2000-05-18 | 2003-11-11 | バイエル アクチェンゲゼルシャフト | 変性ポリイソシアネート |
Also Published As
Publication number | Publication date |
---|---|
ES2866248T3 (es) | 2021-10-19 |
EP3724251A1 (de) | 2020-10-21 |
US11365277B2 (en) | 2022-06-21 |
US20210171698A1 (en) | 2021-06-10 |
EP3724251B1 (de) | 2021-04-07 |
EP3724251B2 (de) | 2023-11-22 |
JP2021521294A (ja) | 2021-08-26 |
CN112041369A (zh) | 2020-12-04 |
WO2019206861A1 (de) | 2019-10-31 |
EP3560974A1 (de) | 2019-10-30 |
EP3851472A1 (de) | 2021-07-21 |
EP3851472B1 (de) | 2023-06-07 |
EP3851472C0 (de) | 2023-06-07 |
CN112041369B (zh) | 2022-11-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7412349B2 (ja) | イオン性親水化ポリイソシアネートの含水率 | |
CN110396165B (zh) | 离子亲水化多异氰酸酯和抗氧化剂 | |
JP2019189866A (ja) | イオン的に親水化されたポリイソシアネートならびにラジカルスカベンジャーおよび/または過酸化物分解剤 | |
KR102591248B1 (ko) | 1,5-디이소시아네이토펜탄을 기재로 하는 친수성 폴리이소시아네이트 | |
JP7397056B2 (ja) | 乾燥が向上したイオン性親水化ポリイソシアネート | |
EP3599255A1 (en) | Ionically hydrophilized polyisocyanates with improved drying | |
JP7514062B2 (ja) | イオン的に親水化されたポリイソシアネートおよび酸化防止剤 | |
WO2020014971A1 (en) | Ionically hydrophilized polyisocyanates with improved drying | |
EP4107198B1 (de) | Polyisocyanatzubereitungen | |
EP4357382A1 (de) | Ionisch modifiziertes polyisocyanatgemisch | |
WO2022129138A1 (de) | Nichtionisch hydrophilierte polyisocyanate, katalyse mit zink-komplexen | |
CN117229476A (zh) | 多异氰酸酯组合物、封端多异氰酸酯组合物、聚氨酯树脂组合物、涂覆组合物及涂覆基材 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220420 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230308 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230404 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230704 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231003 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20231108 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20231205 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20231226 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7412349 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |