MXPA02006782A

MXPA02006782A - Polimeros tipo peine a partir de macromonomeros de polimerizacion de radicales por transferencia atomica (atrp).

Polimeros tipo peine a partir de macromonomeros de polimerizacion de radicales por transferencia atomica (atrp).

Info

Publication number: MXPA02006782A
Authority: MX; Mexico
Prior art keywords: acid; alkylacrylic; acrylic; esters; salts
Prior art date: 2000-01-11

Application number

MXPA02006782A

Other languages

English (en)

Spanish (es)

Inventor

Clemens Auschra

Original Assignee

Ciba Sc Holding Ag

Priority date

2000-01-11

Filing date

2001-01-04

Publication date

2002-10-23

2001-01-04 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

2002-10-23 Publication of MXPA02006782A publication Critical patent/MXPA02006782A/es

Links

229920000642 polymer Polymers 0.000 title claims abstract description 122
239000000203 mixture Substances 0.000 claims abstract description 107
239000000049 pigment Substances 0.000 claims abstract description 63
238000000034 method Methods 0.000 claims abstract description 53
239000002245 particle Substances 0.000 claims abstract description 12
239000012860 organic pigment Substances 0.000 claims abstract description 9
239000001023 inorganic pigment Substances 0.000 claims abstract description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 120
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 95
239000000178 monomer Substances 0.000 claims description 79
239000002253 acid Substances 0.000 claims description 77
150000003839 salts Chemical class 0.000 claims description 75
-1 aralkyl halides Chemical class 0.000 claims description 62
150000002148 esters Chemical class 0.000 claims description 42
239000003999 initiator Substances 0.000 claims description 40
229920001577 copolymer Polymers 0.000 claims description 38
239000012634 fragment Substances 0.000 claims description 36
239000006185 dispersion Substances 0.000 claims description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
239000003054 catalyst Substances 0.000 claims description 25
238000006116 polymerization reaction Methods 0.000 claims description 25
150000008064 anhydrides Chemical class 0.000 claims description 23
239000003505 polymerization initiator Substances 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 23
230000008569 process Effects 0.000 claims description 22
239000011230 binding agent Substances 0.000 claims description 20
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
239000007788 liquid Substances 0.000 claims description 17
239000011248 coating agent Substances 0.000 claims description 16
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 13
150000001408 amides Chemical class 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 13
150000003440 styrenes Chemical class 0.000 claims description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 11
229910052723 transition metal Inorganic materials 0.000 claims description 11
229920002554 vinyl polymer Polymers 0.000 claims description 11
XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 claims description 10
AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 10
230000000977 initiatory effect Effects 0.000 claims description 10
ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 10
238000010526 radical polymerization reaction Methods 0.000 claims description 10
150000003624 transition metals Chemical class 0.000 claims description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims description 9
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 9
125000001931 aliphatic group Chemical group 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 8
229920000180 alkyd Polymers 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
238000012546 transfer Methods 0.000 claims description 8
229920006397 acrylic thermoplastic Polymers 0.000 claims description 7
238000001035 drying Methods 0.000 claims description 7
229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 7
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
239000000975 dye Substances 0.000 claims description 5
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
229920000058 polyacrylate Polymers 0.000 claims description 5
230000000379 polymerizing effect Effects 0.000 claims description 5
239000004814 polyurethane Substances 0.000 claims description 5
229920002635 polyurethane Polymers 0.000 claims description 5
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
229910052782 aluminium Inorganic materials 0.000 claims description 4
239000004014 plasticizer Substances 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
229910019142 PO4 Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
239000006229 carbon black Substances 0.000 claims description 3
239000010439 graphite Substances 0.000 claims description 3
229910002804 graphite Inorganic materials 0.000 claims description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
235000021317 phosphate Nutrition 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 3
150000004760 silicates Chemical class 0.000 claims description 3
239000013008 thixotropic agent Substances 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 2
WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 claims description 2
239000004908 Emulsion polymer Substances 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
235000000177 Indigofera tinctoria Nutrition 0.000 claims description 2
239000005083 Zinc sulfide Substances 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
150000004056 anthraquinones Chemical class 0.000 claims description 2
239000002518 antifoaming agent Substances 0.000 claims description 2
229910052980 cadmium sulfide Inorganic materials 0.000 claims description 2
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 2
150000004338 hydroxy anthraquinones Chemical class 0.000 claims description 2
229940097275 indigo Drugs 0.000 claims description 2
COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 2
229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
230000004048 modification Effects 0.000 claims description 2
238000012986 modification Methods 0.000 claims description 2
OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical class C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 claims description 2
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
125000003367 polycyclic group Chemical group 0.000 claims description 2
IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 2
229910052814 silicon oxide Inorganic materials 0.000 claims description 2
230000000087 stabilizing effect Effects 0.000 claims description 2
PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical compound [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 claims description 2
JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims description 2
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 claims description 2
239000011787 zinc oxide Substances 0.000 claims description 2
LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 2
229910000165 zinc phosphate Inorganic materials 0.000 claims description 2
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims description 2
229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 claims 2
IOOQQSNBRQKBBI-UHFFFAOYSA-N [Ti+4].[O-2].[Cr+3] Chemical compound [Ti+4].[O-2].[Cr+3] IOOQQSNBRQKBBI-UHFFFAOYSA-N 0.000 claims 1
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims 1
150000004696 coordination complex Chemical class 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
150000002979 perylenes Chemical class 0.000 claims 1
229920000915 polyvinyl chloride Polymers 0.000 claims 1
239000004800 polyvinyl chloride Substances 0.000 claims 1
239000002904 solvent Substances 0.000 abstract description 34
229910052751 metal Inorganic materials 0.000 abstract description 10
239000002184 metal Substances 0.000 abstract description 10
150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 7
229920003023 plastic Polymers 0.000 abstract description 6
239000004033 plastic Substances 0.000 abstract description 6
239000002023 wood Substances 0.000 abstract description 5
239000000758 substrate Substances 0.000 abstract description 3
229910010293 ceramic material Inorganic materials 0.000 abstract description 2
238000010560 atom transfer radical polymerization reaction Methods 0.000 abstract 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 41
239000011541 reaction mixture Substances 0.000 description 35
238000000576 coating method Methods 0.000 description 29
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 24
239000003973 paint Substances 0.000 description 24
239000011347 resin Substances 0.000 description 20
229920005989 resin Polymers 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 18
239000008199 coating composition Substances 0.000 description 18
JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 18
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 16
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
239000002270 dispersing agent Substances 0.000 description 16
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 11
238000007639 printing Methods 0.000 description 11
229910016455 AlBN Inorganic materials 0.000 description 10
239000002585 base Substances 0.000 description 10
239000003446 ligand Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
238000007254 oxidation reaction Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000000463 material Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000000843 powder Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
229920000877 Melamine resin Polymers 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000000976 ink Substances 0.000 description 8
238000010907 mechanical stirring Methods 0.000 description 8
125000005907 alkyl ester group Chemical group 0.000 description 7
229920001400 block copolymer Polymers 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 7
229940088644 n,n-dimethylacrylamide Drugs 0.000 description 7
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
150000007524 organic acids Chemical class 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
229910004298 SiO 2 Inorganic materials 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
230000002209 hydrophobic effect Effects 0.000 description 6
VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 6
229910052760 oxygen Chemical group 0.000 description 6
239000001301 oxygen Chemical group 0.000 description 6
238000004448 titration Methods 0.000 description 6
NFTVTXIQFYRSHF-UHFFFAOYSA-N 1-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)C(C)OC(=O)C=C NFTVTXIQFYRSHF-UHFFFAOYSA-N 0.000 description 5
DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000000835 fiber Substances 0.000 description 5
239000011521 glass Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
238000003801 milling Methods 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
238000005956 quaternization reaction Methods 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 description 4
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
150000007942 carboxylates Chemical class 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
229910052681 coesite Inorganic materials 0.000 description 4
229910052906 cristobalite Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
238000000227 grinding Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
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