LU86905A1 - Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains - Google Patents

Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains Download PDF

Info

Publication number: LU86905A1
Authority: LU; Luxembourg
Prior art keywords: formula; amino; compound; methyl; aminophenol
Prior art date: 1987-05-29

Application number

LU86905A

Other languages

English (en)

French (fr)

Inventor

Gerard Lang

Alex Junino

Jean-Jacques Vandenbossche

Herve Borowiak

Original Assignee

Oreal

Priority date (The priority date 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 date listed.)

1987-05-29

Filing date

1987-05-29

Publication date

1989-01-19

1987-05-29 Application filed by Oreal filed Critical Oreal

1987-05-29 Priority to LU86905A priority Critical patent/LU86905A1/fr

1988-05-27 Priority to DE8888108494T priority patent/DE3863698D1/de

1988-05-27 Priority to JP63130028A priority patent/JP2529719B2/ja

1988-05-27 Priority to ES88108494T priority patent/ES2022951B3/es

1988-05-27 Priority to AT88108494T priority patent/ATE65242T1/de

1988-05-27 Priority to EP88108494A priority patent/EP0294669B1/de

1988-05-30 Priority to CA000568077A priority patent/CA1315297C/fr

1988-05-31 Priority to US07/200,170 priority patent/US4960432A/en

1989-01-19 Publication of LU86905A1 publication Critical patent/LU86905A1/fr

1990-06-19 Priority to US07/540,264 priority patent/US5015772A/en

1991-09-10 Priority to GR91401295T priority patent/GR3002684T3/el

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 107
238000000034 method Methods 0.000 title claims abstract description 53
238000002360 preparation method Methods 0.000 title claims abstract description 47
230000008569 process Effects 0.000 title claims abstract description 39
238000007254 oxidation reaction Methods 0.000 title claims abstract description 33
230000003647 oxidation Effects 0.000 title claims abstract description 32
102000011782 Keratins Human genes 0.000 title claims description 11
108010076876 Keratins Proteins 0.000 title claims description 11
239000000835 fiber Substances 0.000 title claims description 11
-1 C1-C4 alkyl radical Chemical class 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
239000002243 precursor Substances 0.000 claims abstract description 22
238000004043 dyeing Methods 0.000 claims abstract description 19
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 14
150000003254 radicals Chemical class 0.000 claims abstract description 7
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 101
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
239000000975 dye Substances 0.000 claims description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 49
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 36
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
230000009467 reduction Effects 0.000 claims description 19
230000029936 alkylation Effects 0.000 claims description 17
238000005804 alkylation reaction Methods 0.000 claims description 17
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
238000005695 dehalogenation reaction Methods 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 12
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 12
239000005695 Ammonium acetate Substances 0.000 claims description 12
235000019257 ammonium acetate Nutrition 0.000 claims description 12
229940043376 ammonium acetate Drugs 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
230000001590 oxidative effect Effects 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
229910052742 iron Inorganic materials 0.000 claims description 8
HQBJSEKQNRSDAZ-UHFFFAOYSA-N 2,6-dimethoxyaniline Chemical compound COC1=CC=CC(OC)=C1N HQBJSEKQNRSDAZ-UHFFFAOYSA-N 0.000 claims description 7
239000007800 oxidant agent Substances 0.000 claims description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 5
PXYFKGIRWVWHRV-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-3-nitroaniline Chemical compound COC1=C(N)C=C(Cl)C(OC)=C1[N+]([O-])=O PXYFKGIRWVWHRV-UHFFFAOYSA-N 0.000 claims description 5
239000000118 hair dye Substances 0.000 claims description 5
PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 claims description 5
SXJQUUPSLJTKKT-UHFFFAOYSA-N 4-hydroxy-2-methoxyaniline Natural products COC1=CC(O)=CC=C1N SXJQUUPSLJTKKT-UHFFFAOYSA-N 0.000 claims description 4
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
238000007796 conventional method Methods 0.000 claims description 4
230000006196 deacetylation Effects 0.000 claims description 4
238000003381 deacetylation reaction Methods 0.000 claims description 4
150000004985 diamines Chemical class 0.000 claims description 4
239000002562 thickening agent Substances 0.000 claims description 4
KVZDSNIWXQNBBS-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-n-methyl-3-nitroaniline Chemical compound CNC1=CC(Cl)=C(OC)C([N+]([O-])=O)=C1OC KVZDSNIWXQNBBS-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
150000004982 aromatic amines Chemical class 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
XPGXSWPADIZALV-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxy-3-nitrophenyl)acetamide Chemical compound COC1=C(Cl)C=C(NC(C)=O)C(OC)=C1[N+]([O-])=O XPGXSWPADIZALV-UHFFFAOYSA-N 0.000 claims description 3
239000002453 shampoo Substances 0.000 claims description 3
GZVVXXLYQIFVCA-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=CC=C1N GZVVXXLYQIFVCA-UHFFFAOYSA-N 0.000 claims description 2
NPAUIIKGLKRJRS-UHFFFAOYSA-N 2,4-dimethoxy-1-n-methylbenzene-1,3-diamine Chemical compound CNC1=CC=C(OC)C(N)=C1OC NPAUIIKGLKRJRS-UHFFFAOYSA-N 0.000 claims description 2
BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims description 2
BVWOHFHLLLPJLH-UHFFFAOYSA-N 2-methoxy-3,5-dimethylbenzene-1,4-diamine Chemical compound COC1=C(C)C(N)=C(C)C=C1N BVWOHFHLLLPJLH-UHFFFAOYSA-N 0.000 claims description 2
UBKPLLYABUUFCE-UHFFFAOYSA-N 4-amino-2,3-dimethylphenol Chemical compound CC1=C(C)C(O)=CC=C1N UBKPLLYABUUFCE-UHFFFAOYSA-N 0.000 claims description 2
JSWVCUXQICMATE-UHFFFAOYSA-N 4-amino-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C=C1N JSWVCUXQICMATE-UHFFFAOYSA-N 0.000 claims description 2
OMVFXCQLSCPJNR-UHFFFAOYSA-N 4-amino-2,6-dimethylphenol Chemical compound CC1=CC(N)=CC(C)=C1O OMVFXCQLSCPJNR-UHFFFAOYSA-N 0.000 claims description 2
ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 claims description 2
MCNBYOWWTITHIG-UHFFFAOYSA-N 4-amino-2-methoxyphenol Chemical compound COC1=CC(N)=CC=C1O MCNBYOWWTITHIG-UHFFFAOYSA-N 0.000 claims description 2
HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 claims description 2
GCWYXRHXGLFVFE-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylaniline Chemical compound CC1=CC(O)=CC(C)=C1N GCWYXRHXGLFVFE-UHFFFAOYSA-N 0.000 claims description 2
YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 claims description 2
VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 claims description 2
GDOIKKMNCIMDAO-UHFFFAOYSA-N 5-amino-1h-pyridin-2-one Chemical compound NC1=CC=C(O)N=C1 GDOIKKMNCIMDAO-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
150000004056 anthraquinones Chemical class 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000000987 azo dye Substances 0.000 claims description 2
125000002091 cationic group Chemical group 0.000 claims description 2
239000000982 direct dye Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
150000002334 glycols Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
239000000852 hydrogen donor Substances 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
101150009274 nhr-1 gene Proteins 0.000 claims description 2
150000002828 nitro derivatives Chemical class 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000002304 perfume Substances 0.000 claims description 2
239000003380 propellant Substances 0.000 claims description 2
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims description 2
239000003352 sequestering agent Substances 0.000 claims description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
150000002391 heterocyclic compounds Chemical class 0.000 claims 2
KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 claims 1
BZWJOZNPOSYQTJ-UHFFFAOYSA-N 4-amino-3-methylbenzene-1,2-diol Chemical compound CC1=C(N)C=CC(O)=C1O BZWJOZNPOSYQTJ-UHFFFAOYSA-N 0.000 claims 1
230000000397 acetylating effect Effects 0.000 claims 1
239000002610 basifying agent Substances 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
229940125773 compound 10 Drugs 0.000 claims 1
239000002537 cosmetic Substances 0.000 claims 1
230000000850 deacetylating effect Effects 0.000 claims 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
239000002736 nonionic surfactant Substances 0.000 claims 1
230000035515 penetration Effects 0.000 claims 1
PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 claims 1
239000003760 tallow Substances 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
239000008365 aqueous carrier Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
239000000047 product Substances 0.000 description 50
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 30
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 25
238000007792 addition Methods 0.000 description 21
239000000460 chlorine Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
239000012429 reaction media Substances 0.000 description 19
238000003756 stirring Methods 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
229910021529 ammonia Inorganic materials 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
238000010438 heat treatment Methods 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
238000005406 washing Methods 0.000 description 9
ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000155 melt Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000004040 coloring Methods 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000005457 ice water Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
229960001484 edetic acid Drugs 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
239000011707 mineral Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000010802 sludge Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
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 4
150000001412 amines Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
239000012256 powdered iron Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
KNKVQMWYXQZYLZ-UHFFFAOYSA-N COC1=CC=CC(=C1)OC.Cl.Cl Chemical compound COC1=CC=CC(=C1)OC.Cl.Cl KNKVQMWYXQZYLZ-UHFFFAOYSA-N 0.000 description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
244000060011 Cocos nucifera Species 0.000 description 3
235000013162 Cocos nucifera Nutrition 0.000 description 3
241000640882 Condea Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000000802 nitrating effect Effects 0.000 description 3
238000006396 nitration reaction Methods 0.000 description 3
230000020477 pH reduction Effects 0.000 description 3
239000004289 sodium hydrogen sulphite Substances 0.000 description 3
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 3
QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
WSZUAGXEGAISLM-UHFFFAOYSA-N 1-chloro-2,4-dimethoxy-3,5-dinitrobenzene Chemical compound COC1=C(Cl)C=C([N+]([O-])=O)C(OC)=C1[N+]([O-])=O WSZUAGXEGAISLM-UHFFFAOYSA-N 0.000 description 2
UFGJYDSSDGBQEO-UHFFFAOYSA-N 2,4-dimethoxybenzene-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=C(N)C(OC)=C1N UFGJYDSSDGBQEO-UHFFFAOYSA-N 0.000 description 2
LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 2
GPJJASIJVRXZFI-UHFFFAOYSA-N 4-methoxybenzene-1,3-diol Chemical compound COC1=CC=C(O)C=C1O GPJJASIJVRXZFI-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Chemical compound OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
230000009471 action Effects 0.000 description 2
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
229920006317 cationic polymer Polymers 0.000 description 2
239000003086 colorant Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
208000003383 pontocerebellar hypoplasia type 3 Diseases 0.000 description 2
229960001755 resorcinol Drugs 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
238000007738 vacuum evaporation Methods 0.000 description 2
OFMRACCIIIDSDN-UHFFFAOYSA-N 1,2,4-trichloro-3,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C([N+]([O-])=O)=C1Cl OFMRACCIIIDSDN-UHFFFAOYSA-N 0.000 description 1
XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 1
OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical class CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
229940113489 2,4-diaminophenoxyethanol Drugs 0.000 description 1
MJMRSGYLARBUDK-UHFFFAOYSA-N 2,4-dimethoxybenzene-1,3-diamine Chemical compound COC1=CC=C(N)C(OC)=C1N MJMRSGYLARBUDK-UHFFFAOYSA-N 0.000 description 1
RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 description 1
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
QAOUFMMMANSOSS-UHFFFAOYSA-N 2-amino-3-(2-hydroxyethyl)phenol Chemical compound NC1=C(O)C=CC=C1CCO QAOUFMMMANSOSS-UHFFFAOYSA-N 0.000 description 1
HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
LIJLYNWYKULUHA-UHFFFAOYSA-N 2-chloroethyl carbamate Chemical compound NC(=O)OCCCl LIJLYNWYKULUHA-UHFFFAOYSA-N 0.000 description 1
SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
MMQPGHVKPBDZLV-UHFFFAOYSA-N 2-methoxy-1-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1OC MMQPGHVKPBDZLV-UHFFFAOYSA-N 0.000 description 1
UVUGDGRIYQQKIT-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-amine Chemical compound O1CCNC2=CC(N)=CC=C21 UVUGDGRIYQQKIT-UHFFFAOYSA-N 0.000 description 1
HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 description 1
XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 description 1
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
SAIXZIVDXDTYCH-UHFFFAOYSA-N 3-chlorobenzene-1,2-diamine Chemical compound NC1=CC=CC(Cl)=C1N SAIXZIVDXDTYCH-UHFFFAOYSA-N 0.000 description 1
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
BNRMHEDSMWOIMC-UHFFFAOYSA-N 4-(2-aminoethoxy)benzene-1,3-diamine Chemical compound NCCOC1=CC=C(N)C=C1N BNRMHEDSMWOIMC-UHFFFAOYSA-N 0.000 description 1
WSEFOZIMAJPJHW-UHFFFAOYSA-N 4-amino-2-(hydroxymethyl)phenol Chemical compound NC1=CC=C(O)C(CO)=C1 WSEFOZIMAJPJHW-UHFFFAOYSA-N 0.000 description 1
XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
IHWPTLPROWODBQ-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine Chemical compound CONC1=CC=C(N)C=C1 IHWPTLPROWODBQ-UHFFFAOYSA-N 0.000 description 1
YFZNTUOMAQXCQZ-UHFFFAOYSA-N 4-n-propan-2-ylbenzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(N)C=C1 YFZNTUOMAQXCQZ-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
NCJXWADUPNGWQK-UHFFFAOYSA-N 5-chloro-2,4-dimethoxy-1-n-methylbenzene-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC(Cl)=C(OC)C(N)=C1OC NCJXWADUPNGWQK-UHFFFAOYSA-N 0.000 description 1
GPCCOYMAIQOSPF-UHFFFAOYSA-N 5-chloro-2,4-dimethoxybenzene-1,3-diamine Chemical compound COC1=C(N)C=C(Cl)C(OC)=C1N GPCCOYMAIQOSPF-UHFFFAOYSA-N 0.000 description 1
GBBDSAVMEZPFCN-UHFFFAOYSA-N 5-chloro-2,4-dimethoxybenzene-1,3-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=C(N)C=C(Cl)C(OC)=C1N GBBDSAVMEZPFCN-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
102100032373 Coiled-coil domain-containing protein 85B Human genes 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Chemical class 0.000 description 1
101000868814 Homo sapiens Coiled-coil domain-containing protein 85B Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
DWAGDHCKFIRKDO-UHFFFAOYSA-N NC1=C(C(=CC=C1OC)Cl)OC Chemical compound NC1=C(C(=CC=C1OC)Cl)OC DWAGDHCKFIRKDO-UHFFFAOYSA-N 0.000 description 1
241000282337 Nasua nasua Species 0.000 description 1
241001465805 Nymphalidae Species 0.000 description 1
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
240000000851 Vaccinium corymbosum Species 0.000 description 1
235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
YBGQLTLJONDTAL-UHFFFAOYSA-N [Na].[Na].[Na].[Na].[Na].C=C.C=C Chemical group [Na].[Na].[Na].[Na].[Na].C=C.C=C YBGQLTLJONDTAL-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Chemical class 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
239000002280 amphoteric surfactant Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
235000021014 blueberries Nutrition 0.000 description 1
239000000872 buffer Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000001913 cellulose Chemical class 0.000 description 1
229920002678 cellulose Chemical class 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000499 gel Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
XQSBLCWFZRTIEO-UHFFFAOYSA-N hexadecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[NH3+] XQSBLCWFZRTIEO-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000003607 modifier Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
QGLITUFXHVRMGV-UHFFFAOYSA-M sodium;tetratriacontyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCOS([O-])(=O)=O QGLITUFXHVRMGV-UHFFFAOYSA-M 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000029305 taxis Effects 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Birds (AREA)
Epidemiology (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Coloring (AREA)

LU86905A 1987-05-29 1987-05-29 Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains LU86905A1 (fr)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
LU86905A LU86905A1 (fr)	1987-05-29	1987-05-29	Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains
DE8888108494T DE3863698D1 (de)	1987-05-29	1988-05-27	Metaphenylendiamine, verfahren zu deren herstellung, zwischenprodukte und verwendung dieser metaphenylendiamine als kuppler fuer die oxidative faerbung von keratinfasern insbesondere von menschlichem haar.
JP63130028A JP2529719B2 (ja)	1987-05-29	1988-05-27	メタフエニレンジアミン化合物、その製造法および染毛組成物
ES88108494T ES2022951B3 (es)	1987-05-29	1988-05-27	Nuevas metafenilenodiaminas, su proceso de preparacion, compuestos intermedios y utilizacion como fijadores para la tintura de oxidacion de fibras querotinicas y en particular de los cabellos humanos
AT88108494T ATE65242T1 (de)	1987-05-29	1988-05-27	Metaphenylendiamine, verfahren zu deren herstellung, zwischenprodukte und verwendung dieser metaphenylendiamine als kuppler fuer die oxidative faerbung von keratinfasern insbesondere von menschlichem haar.
EP88108494A EP0294669B1 (de)	1987-05-29	1988-05-27	Metaphenylendiamine, Verfahren zu deren Herstellung, Zwischenprodukte und Verwendung dieser Metaphenylendiamine als Kuppler für die oxidative Färbung von Keratinfasern insbesondere von menschlichem Haar
CA000568077A CA1315297C (fr)	1987-05-29	1988-05-30	Metaphenylenediamines, leur procede de preparation, composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains
US07/200,170 US4960432A (en)	1987-05-29	1988-05-31	Meta-phenylenediamines, process for preparation thereof, intermediate compounds and use of these meta-phenylenediamines as couplers for the oxidation dyeing of keratinous fibres and especially human hair
US07/540,264 US5015772A (en)	1987-05-29	1990-06-19	Meta-phenylenediamines, process for preparation thereof, intermediate compounds and use of these meta-phenylenediamines as couplers for the oxidation dyeing of keratinous fibres and especially human hair
GR91401295T GR3002684T3 (en)	1987-05-29	1991-09-10	Metaphenylendiamines, process for their preparation, intermediate compounds and use of these metaphenylendiamines as couplers in oxydative colouring of keratinic fibres especially of human hair

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU86905A LU86905A1 (fr)	1987-05-29	1987-05-29	Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains
LU86905		1987-05-29

Publications (1)

Publication Number	Publication Date
LU86905A1 true LU86905A1 (fr)	1989-01-19

Family

ID=19730934

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86905A LU86905A1 (fr)	1987-05-29	1987-05-29	Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains

Country Status (9)

Country	Link
US (2)	US4960432A (de)
EP (1)	EP0294669B1 (de)
JP (1)	JP2529719B2 (de)
AT (1)	ATE65242T1 (de)
CA (1)	CA1315297C (de)
DE (1)	DE3863698D1 (de)
ES (1)	ES2022951B3 (de)
GR (1)	GR3002684T3 (de)
LU (1)	LU86905A1 (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5279619A (en) *	1990-05-31	1994-01-18	L'oreal	Process for dyeing keratinous fibers with 2,4-diamino-1,3-dimethoxybenzene at an acid ph and compositions employed
US5206349A (en) *	1990-08-10	1993-04-27	Toyo Gosei Kogy Co., Ltd.	Aromatic diazo compounds and photosensitive compositions using the same
FR2684296B1 (fr) *	1991-12-03	1995-04-21	Oreal	Procede de teinture des fibres keratiniques avec une alcoxymetaphenylenediamine a ph acide et compositions mises en óoeuvre.
KR100276113B1 (ko) *	1992-05-15	2000-12-15	죤엠.산드레	가속 초임계 유체 추출법
JP3174425B2 (ja) *	1993-03-19	2001-06-11	三井化学株式会社	Ｎ，ｎ−二置換アミノフェノール類の製造法
FR2707487B1 (fr) *	1993-07-13	1995-09-08	Oreal	Composition de teinture d'oxydation des fibres kératiniques comprenant un para-aminophénol, un méta-aminophénol et une métaphénylènediamine, et procédé de teinture utilisant une telle composition.
DE4438129A1 (de) *	1994-10-27	1996-05-02	Schwarzkopf Gmbh Hans	Neue substituierte 2,4-Diaminophenole, Verfahren zu ihrer Herstellung und Haarfärbemittel
US5849042A (en) *	1997-11-19	1998-12-15	Bristol-Myers Squibb	Hair dye compositions containing 2,3 dialkyl-4-aminophenol and a 2-alkyl-1-naphthol
US6673932B2 (en) *	2001-01-23	2004-01-06	The Procter & Gamble Company	Primary intermediates for oxidative coloration of hair
ATE348596T1 (de) *	2001-01-23	2007-01-15	P & G Clairol Inc	Primäres zwischenprodukt für die oxidative haarfärbung
AU2002251796B2 (en) *	2001-01-23	2005-07-07	P&G-Clairol, Inc.	Primary intermediates for oxidative coloration of hair
CN1486170A (zh) *	2001-01-31	2004-03-31	P&G	用于氧化性染发的新的偶合剂
AU2003223214B2 (en) *	2002-03-01	2008-09-18	Celltech R & D, Inc.	Methods to increase or decrease bone density
DE10260834A1 (de)	2002-12-23	2004-07-01	Henkel Kgaa	Neue Kupplerkomponenten
FR2902323B1 (fr) *	2006-06-20	2008-08-08	Oreal	Procede pour la teinture predictible des fibres keratiniques par application d'une composition contenant un derive diamino-n,n-dihydro-pyrazolone et d'une composition fondamentale ou a reflets dores
JP5642670B2 (ja) *	2008-06-16	2014-12-17	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	ダビガトランの合成の中間体の製造方法
FR3001387B1 (fr)	2013-01-29	2015-06-05	Oreal	Composition de teinture mettant en oeuvre au moins un coupleur de type meta-phenylenediamine substituee en position 2 dans un milieu comprenant un corps gras, procedes et dispositif

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE625997A (de) *	1962-02-28
DE2628999C2 (de) *	1976-06-28	1987-03-26	Henkel KGaA, 4000 Düsseldorf	Haarfärbemittel
FR2362116A1 (fr) *	1976-08-20	1978-03-17	Oreal	Metaphenylenediamines et compositions tinctoriales les contenant
FR2430932A1 (fr) *	1978-07-12	1980-02-08	Oreal	Metaphenylenediamines et compositions tinctoriales les contenant
DE3137473A1 (de) *	1981-09-21	1983-04-07	Henkel KGaA, 4000 Düsseldorf	"n-substituierte 2.4-diamino-m-xylole und diese enthaltende haarfaerbemittel"
US4566876A (en) *	1983-03-10	1986-01-28	Clairol Incorporated	Meta-phenylenediamine coupler compounds and oxidative hair dye compositions and methods using same
US4766244A (en) *	1986-10-30	1988-08-23	The Dow Chemical Company	High purity process for the preparation of 4,6-diamino-1,3-benzenediol
LU86903A1 (fr) *	1987-05-29	1989-01-19	Oreal	Utilisation comme coupleur du 2,4-diamino-1,3-dimethoxybenzene ou l'un de ses sels,en association avec des precurseurs de colorants d'oxydation,pour la teinture des cheveux humains,composition de teinture capillaire contenant ledit coupleur et procede de preparation dudit coupleur
LU86904A1 (fr) *	1987-05-29	1989-01-19	Oreal	Nouvelles chlorometaphenylenediamines,leur utilisation en tanque coupleurs en teinture d'oxydation des fibres keratiniques,compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions

1987
- 1987-05-29 LU LU86905A patent/LU86905A1/fr unknown
1988
- 1988-05-27 AT AT88108494T patent/ATE65242T1/de not_active IP Right Cessation
- 1988-05-27 JP JP63130028A patent/JP2529719B2/ja not_active Expired - Fee Related
- 1988-05-27 DE DE8888108494T patent/DE3863698D1/de not_active Expired - Lifetime
- 1988-05-27 EP EP88108494A patent/EP0294669B1/de not_active Expired - Lifetime
- 1988-05-27 ES ES88108494T patent/ES2022951B3/es not_active Expired - Lifetime
- 1988-05-30 CA CA000568077A patent/CA1315297C/fr not_active Expired - Fee Related
- 1988-05-31 US US07/200,170 patent/US4960432A/en not_active Expired - Lifetime
1990
- 1990-06-19 US US07/540,264 patent/US5015772A/en not_active Expired - Lifetime
1991
- 1991-09-10 GR GR91401295T patent/GR3002684T3/el unknown

Also Published As

Publication number	Publication date
ATE65242T1 (de)	1991-08-15
JPS6452710A (en)	1989-02-28
GR3002684T3 (en)	1993-01-25
CA1315297C (fr)	1993-03-30
EP0294669A1 (de)	1988-12-14
EP0294669B1 (de)	1991-07-17
ES2022951B3 (es)	1991-12-16
JP2529719B2 (ja)	1996-09-04
US4960432A (en)	1990-10-02
US5015772A (en)	1991-05-14
DE3863698D1 (de)	1991-08-22

Publication	Publication Date	Title
CH661501A5 (fr)	1987-07-31	Composes derivant du amino-3 propanol-2 utilisables pour la teinture des cheveux, leur procede de preparation, composition de teinture les contenant et procede de teinture de cheveux correspondant.
EP0591373B1 (de)	1996-05-22	Meta-aminophenolen,verwendung als kupplungen für oxydationsfarbstoffe für keratinische fäser, zusammensetzungen und farbenprozessen
LU86905A1 (fr)	1989-01-19	Nouvelles metaphenylenediamines,leur procede de preparation,composes intermediaires et utilisation de ces metaphenylenediamines en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier des cheveux humains
CA1327975C (fr)	1994-03-22	Para-aminophenols 3-substitues, leur procede de preparation, leur utilisation pour la teinture des fibres keratiniques et les composes intermediaires utilises dans le procede de preparation
CA1306952C (fr)	1992-09-01	Utilisation comme coupleur du 2,4-diamino-1,3-dimethoxybenzene ou l'un de ses sels, en association avec des precurseurs de colorants d'oxydation, pour la teinture des cheveux humains, composition de teinture capillairecontenant ledit coupleur et procede de preparation dudit coupleur
FR2630438A1 (fr)	1989-10-27	Nouvelles p-phenylenediamines, leur procede de preparation, composition tinctoriale les contenant et procede de teinture correspondant
FR2492370A1 (fr)	1982-04-23	Nouveaux derives nitres de la serie benzenique, leur procede de preparation et leur utilisation en teinture des fibres keratiniques
CA1341194C (fr)	2001-02-27	Composition de teinture de fibre keratinique contenant des bases d'oxydation dites "doubles" et des bases d'oxydation dites "simples", et procede de teinture la mettant en oeuvre
CA1314564C (fr)	1993-03-16	Chlorometaphenylenediamines, leur utilisation en tant que coupleurs en teinture d'oxydation des fibres keratiniques, compositions tinctoriales pour cheveux contenant ces composes et procede de teinture utilisant lesdites compositions
FR2547300A1 (fr)	1984-12-14	Nouveaux metaaminophenols substitues, leur procede de preparation, compositions tinctoriales pour cheveux les contenant et procede de teinture de cheveux correspondant
CA1305184C (fr)	1992-07-14	2-nitro metaphenylene-diamines substituees, leur procede de preparation et leurutilisation en teinture des fibres keratiniques et en particulier des cheveux humains
EP0359618B1 (de)	1993-03-17	2-Substituierte Paraaminophenole und ihre Verwendung für die Färbung von keratinischen Fasern
CA2003594A1 (fr)	1990-05-22	Nouvelles metaphenylenediamines trialcoxy-substitues, leur procede de preparation, et leur utilisation en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques et en particulier les cheveux humains
WO1993018739A1 (fr)	1993-09-30	Metaphenylenediamines soufrees en position 2 pour la teinture des cheveux
FR2638453A1 (fr)	1990-05-04	Ortho-aminophenols 5-substitues, procede pour les preparer et leur utilisation pour la teinture d'oxydation des fibres keratiniques
LU83063A1 (fr)	1982-09-10	Composition tinctoriale pour fibres keratiniques a base de nitro-3 orthophenylenediamines,nouvelles nitro-3 orthophenylenediamines utilisees et leurs procedes de preparation
FR2687308A1 (fr)	1993-08-20	Procede de teinture des fibres keratiniques a ph acide mettant en óoeuvre des metaphenylenediamines soufrees et compositions mises en óoeuvre dans le procede.
LU86931A1 (fr)	1989-03-08	2,4-diamino-1,3,5-trimethoxybenzene,son procede de preparation et son utilisation comme coupleur dans les teintures d'oxydation pour fibres keratiniques
FR2569401A1 (fr)	1986-02-28	Nouveaux derives dimethyles de nitro-3 amino-4 aniline, leur procede de preparation et leur utilisation en teinture des fibres keratiniques
LU82861A1 (fr)	1982-05-10	Nouvelles nitro-paraphenylenediamines,leur procede de preparation et leur utilisation en teinture des fibres keratiniques
FR2696455A1 (fr)	1994-04-08	Nouveaux métaaminophénols soufrés, leur application, notamment en teinture.
WO1993016990A1 (fr)	1993-09-02	Composition tinctoriale pour fibres keratiniques contenant des metaphenylenediamines soufrees, procede de teinture et nouvelles metaphenylenediamines soufrees et leur procede de preparation
CH667869A5 (fr)	1988-11-15	Dinitro-2,4,hydroxyalkyl-6 anilines, leur procede de preparation et leur utilisation en teinture des fibres keratiniques, notamment des cheveux humains.
LU83315A1 (fr)	1983-03-24	Nouvelles nitro-paraphenylenediamines,leur procede de preparation et leur utilisation en teinture des fibres keratiniques
LU85680A1 (fr)	1986-07-17	Nouvelles amino-2,nitro-4,hydroxyalkyl-6 anilines,leur procede de preparation et leur utilisation en teinture des fibres keratiniques