DE2604699A1 - Neue basische azofarbstoffe und deren additionssalze mit saeuren - Google Patents
Neue basische azofarbstoffe und deren additionssalze mit saeurenInfo
- Publication number
- DE2604699A1 DE2604699A1 DE19762604699 DE2604699A DE2604699A1 DE 2604699 A1 DE2604699 A1 DE 2604699A1 DE 19762604699 DE19762604699 DE 19762604699 DE 2604699 A DE2604699 A DE 2604699A DE 2604699 A1 DE2604699 A1 DE 2604699A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- aminomethyl
- hydrogen
- compound according
- hydroxy
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 17
- 239000002253 acid Substances 0.000 title claims description 15
- 150000007513 acids Chemical class 0.000 title description 3
- 238000005859 coupling reaction Methods 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 43
- 230000008878 coupling Effects 0.000 claims description 41
- 238000010168 coupling process Methods 0.000 claims description 41
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 238000006149 azo coupling reaction Methods 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 71
- 239000000243 solution Substances 0.000 description 67
- 239000000123 paper Substances 0.000 description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 238000012360 testing method Methods 0.000 description 38
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 32
- -1 methoxy, ethoxy, propoxy Chemical group 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 23
- 230000000740 bleeding effect Effects 0.000 description 23
- 229960000583 acetic acid Drugs 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000012954 diazonium Substances 0.000 description 18
- 239000000987 azo dye Substances 0.000 description 15
- 150000001989 diazonium salts Chemical class 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 13
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 12
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- CRRLDLPBQWRVGN-UHFFFAOYSA-N n-[2-methyl-4-[3-methyl-4-(3-oxobutanoylamino)phenyl]phenyl]-3-oxobutanamide Chemical compound C1=C(C)C(NC(=O)CC(=O)C)=CC=C1C1=CC=C(NC(=O)CC(C)=O)C(C)=C1 CRRLDLPBQWRVGN-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000344 soap Substances 0.000 description 11
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 10
- 238000004043 dyeing Methods 0.000 description 10
- AQYMRQUYPFCXDM-UHFFFAOYSA-N 3-hydroxy-n-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O AQYMRQUYPFCXDM-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 150000003931 anilides Chemical class 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- XDWATWCCUTYUDE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1NC(=O)C1=CC2=CC=CC=C2C=C1O XDWATWCCUTYUDE-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000004040 coloring Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 7
- QIHKTBRNOLQDGQ-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C=2C(=CC3=CC=CC=C3C=2)O)=C1OC QIHKTBRNOLQDGQ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- AMEITLQTRCBPTA-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=C(C)C=C1 Chemical compound N1=C(C)C=C(O)N1C1=CC=C(C)C=C1 AMEITLQTRCBPTA-UHFFFAOYSA-N 0.000 description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000007844 bleaching agent Substances 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- PSRNXESQSJEQMN-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound CC1=CC(Cl)=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O PSRNXESQSJEQMN-UHFFFAOYSA-N 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- BPEXTIMJLDWDTL-UHFFFAOYSA-N 2`-Methylacetanilide Chemical compound CC(=O)NC1=CC=CC=C1C BPEXTIMJLDWDTL-UHFFFAOYSA-N 0.000 description 5
- ZDBWYUOUYNQZBM-UHFFFAOYSA-N 3-(aminomethyl)aniline Chemical compound NCC1=CC=CC(N)=C1 ZDBWYUOUYNQZBM-UHFFFAOYSA-N 0.000 description 5
- YZJSKRBKHCLMQC-UHFFFAOYSA-N 3-hydroxy-n-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 YZJSKRBKHCLMQC-UHFFFAOYSA-N 0.000 description 5
- UIXFPIHXQQZAGX-UHFFFAOYSA-N 3-hydroxy-n-(4-methoxyphenyl)naphthalene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O UIXFPIHXQQZAGX-UHFFFAOYSA-N 0.000 description 5
- LAKNSQZHAUYJJM-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound COC1=CC=C(OC)C(NC(=O)C=2C(=CC3=CC=CC=C3C=2)O)=C1 LAKNSQZHAUYJJM-UHFFFAOYSA-N 0.000 description 5
- NXIGDUAONGBUKR-UHFFFAOYSA-N n-(2-ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O NXIGDUAONGBUKR-UHFFFAOYSA-N 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- FBLAHUMENIHUGG-UHFFFAOYSA-N 3-hydroxy-n-(2-methylphenyl)naphthalene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O FBLAHUMENIHUGG-UHFFFAOYSA-N 0.000 description 4
- PMYDPQQPEAYXKD-UHFFFAOYSA-N 3-hydroxy-n-naphthalen-2-ylnaphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(NC(=O)C3=CC4=CC=CC=C4C=C3O)=CC=C21 PMYDPQQPEAYXKD-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- VTPSNRIENVXKCI-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound CC1=CC(C)=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O VTPSNRIENVXKCI-UHFFFAOYSA-N 0.000 description 4
- CIPHTOQKGSLCLV-UHFFFAOYSA-N n-phenylnaphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC1=CC=CC=C1 CIPHTOQKGSLCLV-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000001044 red dye Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- HRUDXLGQUFFFMZ-UHFFFAOYSA-N 3,5-bis(aminomethyl)-4-methoxyaniline Chemical compound COC1=C(CN)C=C(N)C=C1CN HRUDXLGQUFFFMZ-UHFFFAOYSA-N 0.000 description 3
- BPLTYDPIHLNUAR-UHFFFAOYSA-N 3-hydroxy-n-(4-methoxy-2-methylphenyl)naphthalene-2-carboxamide Chemical compound CC1=CC(OC)=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O BPLTYDPIHLNUAR-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- XZOACPDZZYNJER-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound CC1=CC=C(Cl)C=C1NC(=O)C1=CC2=CC=CC=C2C=C1O XZOACPDZZYNJER-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JUNWKCORRLQERY-UHFFFAOYSA-N 1-methoxy-N-phenylnaphthalene-2-carboxamide Chemical compound COC1=C(C=CC2=CC=CC=C12)C(=O)NC1=CC=CC=C1 JUNWKCORRLQERY-UHFFFAOYSA-N 0.000 description 2
- AHRKSYJJWYQHEX-UHFFFAOYSA-N 1-methoxy-n-(4-methoxyphenyl)naphthalene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(C=CC=C2)C2=C1OC AHRKSYJJWYQHEX-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- BXAULJHRQJRSPZ-UHFFFAOYSA-N 3,5-bis(aminomethyl)-4-bromo-2-methoxyaniline Chemical compound COC1=C(N)C=C(CN)C(Br)=C1CN BXAULJHRQJRSPZ-UHFFFAOYSA-N 0.000 description 2
- CVTOERDZZZWRIG-UHFFFAOYSA-N 3,5-bis(aminomethyl)-4-methoxyaniline;trihydrochloride Chemical compound Cl.Cl.Cl.COC1=C(CN)C=C(N)C=C1CN CVTOERDZZZWRIG-UHFFFAOYSA-N 0.000 description 2
- XISIVCOGFVIDGM-UHFFFAOYSA-N 3-(aminomethyl)-2-chloro-4-methoxy-5-methylaniline Chemical compound COC1=C(C)C=C(N)C(Cl)=C1CN XISIVCOGFVIDGM-UHFFFAOYSA-N 0.000 description 2
- HKHBVQNIHQQSSU-UHFFFAOYSA-N 3-(aminomethyl)-5-chloro-2-propylaniline Chemical compound CCCC1=C(N)C=C(Cl)C=C1CN HKHBVQNIHQQSSU-UHFFFAOYSA-N 0.000 description 2
- BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 2
- WPAVIDDSCRWHFU-UHFFFAOYSA-N 5-(aminomethyl)-2,3,4-trimethylaniline Chemical compound CC1=C(C)C(N)=CC(CN)=C1C WPAVIDDSCRWHFU-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 206010039587 Scarlet Fever Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- GMDALVNLRHJDED-UHFFFAOYSA-N 1,3-dimethoxy-n-phenylnaphthalene-2-carboxamide Chemical compound COC1=CC2=CC=CC=C2C(OC)=C1C(=O)NC1=CC=CC=C1 GMDALVNLRHJDED-UHFFFAOYSA-N 0.000 description 1
- NZWNOSGSSIOEIV-UHFFFAOYSA-N 2-[[n-[(1,3-dioxoisoindol-2-yl)methyl]anilino]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CN(CN1C(C2=CC=CC=C2C1=O)=O)C1=CC=CC=C1 NZWNOSGSSIOEIV-UHFFFAOYSA-N 0.000 description 1
- SIEIFSKZDMFTSW-UHFFFAOYSA-N 2-chloro-4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C(Cl)=C1 SIEIFSKZDMFTSW-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- DRWBSAPKYQKCCI-UHFFFAOYSA-N 3,5-bis(aminomethyl)-2-methoxy-4-methylaniline Chemical compound COC1=C(N)C=C(CN)C(C)=C1CN DRWBSAPKYQKCCI-UHFFFAOYSA-N 0.000 description 1
- NXPSSGDUHDPGHB-UHFFFAOYSA-N 3,5-bis(aminomethyl)-2-methoxyaniline Chemical compound COC1=C(N)C=C(CN)C=C1CN NXPSSGDUHDPGHB-UHFFFAOYSA-N 0.000 description 1
- QJESTWUFGJGFLR-UHFFFAOYSA-N 3,5-bis(aminomethyl)-2-methoxyaniline;trihydrochloride Chemical compound Cl.Cl.Cl.COC1=C(N)C=C(CN)C=C1CN QJESTWUFGJGFLR-UHFFFAOYSA-N 0.000 description 1
- VWYGDYIADJNFGK-UHFFFAOYSA-N 3-(aminomethyl)-2,5-dichloro-4-methoxyaniline Chemical compound COC1=C(Cl)C=C(N)C(Cl)=C1CN VWYGDYIADJNFGK-UHFFFAOYSA-N 0.000 description 1
- GCZYXXZGQVWEEW-UHFFFAOYSA-N 3-(aminomethyl)-2-chloro-4,5-dimethoxyaniline Chemical compound COC1=CC(N)=C(Cl)C(CN)=C1OC GCZYXXZGQVWEEW-UHFFFAOYSA-N 0.000 description 1
- FGHKSNZGDNBHMK-UHFFFAOYSA-N 3-(aminomethyl)-2-fluoro-4,5-dimethoxyaniline Chemical compound COC1=CC(N)=C(F)C(CN)=C1OC FGHKSNZGDNBHMK-UHFFFAOYSA-N 0.000 description 1
- XNMXDYJDFWSWIR-UHFFFAOYSA-N 3-(aminomethyl)-5-bromoaniline Chemical compound NCC1=CC(N)=CC(Br)=C1 XNMXDYJDFWSWIR-UHFFFAOYSA-N 0.000 description 1
- DQYAWARSARXAIE-UHFFFAOYSA-N 3-(aminomethyl)-5-chloro-2,4-diethoxyaniline Chemical compound CCOC1=C(N)C=C(Cl)C(OCC)=C1CN DQYAWARSARXAIE-UHFFFAOYSA-N 0.000 description 1
- ZRQQFRYVTYHFAM-UHFFFAOYSA-N 3-(aminomethyl)-5-ethyl-2-methylaniline Chemical compound CCC1=CC(N)=C(C)C(CN)=C1 ZRQQFRYVTYHFAM-UHFFFAOYSA-N 0.000 description 1
- YQKXKPASJHLTDN-UHFFFAOYSA-N 3-(aminomethyl)-5-methyl-2-propan-2-ylaniline Chemical compound CC(C)C1=C(N)C=C(C)C=C1CN YQKXKPASJHLTDN-UHFFFAOYSA-N 0.000 description 1
- SJIFOHPZHHKGLQ-UHFFFAOYSA-N 3-(aminomethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC(CN)=C1 SJIFOHPZHHKGLQ-UHFFFAOYSA-N 0.000 description 1
- VYUNCHWZPFLDAP-UHFFFAOYSA-N 3-(aminomethyl)aniline;dihydrochloride Chemical compound Cl.Cl.NCC1=CC=CC(N)=C1 VYUNCHWZPFLDAP-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- RGBBCHBCGNDCRL-UHFFFAOYSA-N 3-n,4-dimethylbenzene-1,3-diamine Chemical compound CNC1=CC(N)=CC=C1C RGBBCHBCGNDCRL-UHFFFAOYSA-N 0.000 description 1
- CDSPOZXUDJUBEZ-UHFFFAOYSA-N 4-(1-aminoethyl)aniline Chemical compound CC(N)C1=CC=C(N)C=C1 CDSPOZXUDJUBEZ-UHFFFAOYSA-N 0.000 description 1
- LNPMZQXEPNWCMG-UHFFFAOYSA-N 4-(2-aminoethyl)aniline Chemical compound NCCC1=CC=C(N)C=C1 LNPMZQXEPNWCMG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XZROQRMSJUCXKB-UHFFFAOYSA-N 4-(aminomethyl)-2-bromoaniline Chemical compound NCC1=CC=C(N)C(Br)=C1 XZROQRMSJUCXKB-UHFFFAOYSA-N 0.000 description 1
- UKADWWBTPJFZOM-UHFFFAOYSA-N 4-(aminomethyl)-2-chloroaniline Chemical compound NCC1=CC=C(N)C(Cl)=C1 UKADWWBTPJFZOM-UHFFFAOYSA-N 0.000 description 1
- ITVCZVQGSJCSLW-UHFFFAOYSA-N 4-(aminomethyl)-2-methoxyaniline Chemical compound COC1=CC(CN)=CC=C1N ITVCZVQGSJCSLW-UHFFFAOYSA-N 0.000 description 1
- XRFZQKJDGWOSFO-UHFFFAOYSA-N 4-(aminomethyl)-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1CN XRFZQKJDGWOSFO-UHFFFAOYSA-N 0.000 description 1
- GMYWFOGAJAQFHN-UHFFFAOYSA-N 4-(aminomethyl)aniline;dihydrochloride Chemical compound Cl.Cl.NCC1=CC=C(N)C=C1 GMYWFOGAJAQFHN-UHFFFAOYSA-N 0.000 description 1
- WGZYVHFXLPDNDL-UHFFFAOYSA-N 4-benzoyl-2-phenylpyrazole-3-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)C(=C1C#N)C=NN1C1=CC=CC=C1 WGZYVHFXLPDNDL-UHFFFAOYSA-N 0.000 description 1
- XZWVVKZGABZHIW-UHFFFAOYSA-N 5-(aminomethyl)-2-methoxy-3-propan-2-ylaniline Chemical compound COC1=C(N)C=C(CN)C=C1C(C)C XZWVVKZGABZHIW-UHFFFAOYSA-N 0.000 description 1
- PPJILWNZWLDSCP-UHFFFAOYSA-N 5-(aminomethyl)-2-methoxyaniline Chemical compound COC1=CC=C(CN)C=C1N PPJILWNZWLDSCP-UHFFFAOYSA-N 0.000 description 1
- WNCSDYWOHLQEHM-UHFFFAOYSA-N 5-(aminomethyl)-2-methylaniline Chemical compound CC1=CC=C(CN)C=C1N WNCSDYWOHLQEHM-UHFFFAOYSA-N 0.000 description 1
- ZYGSHSBUKWLOEG-UHFFFAOYSA-N 5-bromo-3-N-methylbenzene-1,3-diamine Chemical compound CNC1=CC(N)=CC(Br)=C1 ZYGSHSBUKWLOEG-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PRZFKFLPHSPCSM-UHFFFAOYSA-N C1=CC(OC)=CC=C1N1C(O)=CC(C)=N1 Chemical compound C1=CC(OC)=CC=C1N1C(O)=CC(C)=N1 PRZFKFLPHSPCSM-UHFFFAOYSA-N 0.000 description 1
- QBGRRIQUBAWXFP-UHFFFAOYSA-N C1=CC(OCC)=CC=C1N1C(O)=CC(C)=N1 Chemical compound C1=CC(OCC)=CC=C1N1C(O)=CC(C)=N1 QBGRRIQUBAWXFP-UHFFFAOYSA-N 0.000 description 1
- PNVZOELSMWBHIS-UHFFFAOYSA-N CC1=CC(N)=CC(NC)=C1C Chemical compound CC1=CC(N)=CC(NC)=C1C PNVZOELSMWBHIS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RLBVEDPQLZEVHZ-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=C(Cl)C=C(Cl)C=C1Cl Chemical compound N1=C(C)C=C(O)N1C1=C(Cl)C=C(Cl)C=C1Cl RLBVEDPQLZEVHZ-UHFFFAOYSA-N 0.000 description 1
- WYXKSPNVSLCJMY-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC(C)=CC=C1C Chemical compound N1=C(C)C=C(O)N1C1=CC(C)=CC=C1C WYXKSPNVSLCJMY-UHFFFAOYSA-N 0.000 description 1
- VHAFZRAVPXOBCZ-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=C(I)C=C1 Chemical compound N1=C(C)C=C(O)N1C1=CC=C(I)C=C1 VHAFZRAVPXOBCZ-UHFFFAOYSA-N 0.000 description 1
- AVYCZZCVLCJGGQ-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=CC(Br)=C1 Chemical compound N1=C(C)C=C(O)N1C1=CC=CC(Br)=C1 AVYCZZCVLCJGGQ-UHFFFAOYSA-N 0.000 description 1
- KEQIAXAZLDYMQK-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=CC([N+]([O-])=O)=C1 Chemical compound N1=C(C)C=C(O)N1C1=CC=CC([N+]([O-])=O)=C1 KEQIAXAZLDYMQK-UHFFFAOYSA-N 0.000 description 1
- PLVBQEFRONZLHO-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=CC=C1 Chemical compound N1=C(C)C=C(O)N1C1=CC=CC=C1 PLVBQEFRONZLHO-UHFFFAOYSA-N 0.000 description 1
- DSEREVMRCRKRBM-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=CC=C1C Chemical compound N1=C(C)C=C(O)N1C1=CC=CC=C1C DSEREVMRCRKRBM-UHFFFAOYSA-N 0.000 description 1
- AOJZHOSAFRXPQQ-UHFFFAOYSA-N N1=C(C)C=C(O)N1C1=CC=CC=C1Cl Chemical compound N1=C(C)C=C(O)N1C1=CC=CC=C1Cl AOJZHOSAFRXPQQ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZWRMPKCMKQJGKM-UHFFFAOYSA-N OC1=CC=NN1.NC1=CC=CC=C1 Chemical compound OC1=CC=NN1.NC1=CC=CC=C1 ZWRMPKCMKQJGKM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KHMUYSPUAKRBAN-UHFFFAOYSA-N n'-(aminomethyl)-n'-phenylmethanediamine Chemical compound NCN(CN)C1=CC=CC=C1 KHMUYSPUAKRBAN-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- NUJAPVSRDGSINW-UHFFFAOYSA-N n'-phenylmethanediamine Chemical compound NCNC1=CC=CC=C1 NUJAPVSRDGSINW-UHFFFAOYSA-N 0.000 description 1
- UPBCYFAIJVMPPF-UHFFFAOYSA-N n-(4-chloro-3-methoxyphenyl)-3-hydroxy-2-methoxy-1h-naphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C2(C(=CC3=CC=CC=C3C2)O)OC)=C1 UPBCYFAIJVMPPF-UHFFFAOYSA-N 0.000 description 1
- JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide 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
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013055 pulp slurry Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54801575A | 1975-02-07 | 1975-02-07 | |
| US64156675A | 1975-12-17 | 1975-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2604699A1 true DE2604699A1 (de) | 1976-08-19 |
Family
ID=27068736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762604699 Pending DE2604699A1 (de) | 1975-02-07 | 1976-02-06 | Neue basische azofarbstoffe und deren additionssalze mit saeuren |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2810246A1 (de) * | 1977-03-09 | 1978-09-14 | Sterling Drug Inc | Azoverbindungen und verfahren zu deren herstellung |
| EP1508598A1 (de) * | 2003-08-16 | 2005-02-23 | DyStar Textilfarben GmbH & Co. Deutschland KG | Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093829B1 (en) * | 1980-05-08 | 1987-01-07 | Sandoz Ag | Sulphofree basic azo compounds in metal-free 1:1 or 1:2 metal complex form |
-
1976
- 1976-01-26 CA CA244,249A patent/CA1064914A/en not_active Expired
- 1976-01-27 GB GB3181/76A patent/GB1534563A/en not_active Expired
- 1976-02-04 NO NO760371A patent/NO760371L/no unknown
- 1976-02-05 FR FR7603216A patent/FR2300120A1/fr active Granted
- 1976-02-05 NL NL7601205A patent/NL7601205A/xx not_active Application Discontinuation
- 1976-02-05 IT IT19945/76A patent/IT1055870B/it active
- 1976-02-06 BR BR7600748A patent/BR7600748A/pt unknown
- 1976-02-06 CH CH148076A patent/CH609364A5/xx not_active IP Right Cessation
- 1976-02-06 DE DE19762604699 patent/DE2604699A1/de active Pending
- 1976-02-07 JP JP51012739A patent/JPS51103930A/ja active Pending
- 1976-06-23 SE SE7601339A patent/SE7601339L/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2810246A1 (de) * | 1977-03-09 | 1978-09-14 | Sterling Drug Inc | Azoverbindungen und verfahren zu deren herstellung |
| EP1508598A1 (de) * | 2003-08-16 | 2005-02-23 | DyStar Textilfarben GmbH & Co. Deutschland KG | Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
| EP1669417A1 (de) * | 2003-08-16 | 2006-06-14 | DyStar Textilfarben GmbH & Co. Deutschland KG | Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| NO760371L (enrdf_load_stackoverflow) | 1976-08-10 |
| CH609364A5 (en) | 1979-02-28 |
| IT1055870B (it) | 1982-01-11 |
| FR2300120B3 (enrdf_load_stackoverflow) | 1979-10-12 |
| BR7600748A (pt) | 1976-08-31 |
| JPS51103930A (enrdf_load_stackoverflow) | 1976-09-14 |
| NL7601205A (nl) | 1976-08-10 |
| GB1534563A (en) | 1978-12-06 |
| CA1064914A (en) | 1979-10-23 |
| FR2300120A1 (fr) | 1976-09-03 |
| SE7601339L (sv) | 1976-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2915323C2 (enrdf_load_stackoverflow) | ||
| EP0034725B1 (de) | Imidazolylmethylgruppen enthaltende Farbstoffe und deren Verwendung | |
| DE2810246A1 (de) | Azoverbindungen und verfahren zu deren herstellung | |
| EP0482508B1 (de) | Biskationische Azofarbstoffe sowie deren Zwischenprodukte | |
| DE1965993C3 (de) | Sulfogruppenfreie Azofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben und Bedrucken von Papier | |
| DE2604699A1 (de) | Neue basische azofarbstoffe und deren additionssalze mit saeuren | |
| CH653697A5 (de) | Polykationische azoverbindung, ihre herstellung und verwendung. | |
| DE2144907C3 (de) | Neue wasserunlösliche Mono- und Disazoverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Pigmente | |
| DE3609590C2 (enrdf_load_stackoverflow) | ||
| DE2154942A1 (de) | Neue monoazo-reaktivfarbstoffe, ihre verwendung und verfahren zu ihrer herstellung | |
| DE2022624A1 (de) | Basischer Disazofarbstoff und Verfahren zur Herstellung desselben | |
| EP1317512B1 (de) | Bisazofarbstoffe auf der basis von hydroxynaphthalincarbonsäure | |
| EP0051187B1 (de) | Kationische Styrylfarbstoffe, ihre Herstellung und ihre Verwendung zum Färben von natürlichen und synthetischen kationisch anfärbbaren Substraten | |
| DE2239445C3 (de) | Kationische Pyrazolfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| US4217272A (en) | Novel monoazo and disazo colorants from aminoalkylanilines and bis(aminoalkyl)anilines | |
| DE2130040C3 (de) | Wasserunlösliche Monoazoverbindüngen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| US4153598A (en) | Monoazo and diazo colorants from aminoalkylanilines and bis(aminoalkyl)anilines | |
| DE19500203A1 (de) | Kationisch verbrückte Tetrakisazofarbstoffe mit unterschiedlichen Kupplern, ihre Herstellung und Verwendung | |
| DE1903058C (de) | Verfahren zur Herstellung von basischen Azofarbstoffen und deren Verwendung zum Farben u Bedrucken | |
| DE3717869A1 (de) | Triazinhaltige monoazoverbindungen | |
| DE2302522C3 (de) | Disazoplgmente, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben | |
| DE3044563A1 (de) | Imidazolylmethylengruppen enthaltende farbstoffe und deren verwendung | |
| CH344150A (de) | Verfahren zur Herstellung wasserunlöslicher Monoazofarbstoffe | |
| CH601432A5 (en) | Yellow violet biscationic azo dyes free from sulpho gps. | |
| CH380268A (de) | Verfahren zur Herstellung wasserunlöslicher Disazofarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |