Patent GB-1076915-A (GB)
Title: Nitroparaphenylenediamine derivatives
Inventor: KALOPISSIS GREGOIRE
IPC: D06P1/19
Filed: 1966-04-25
Abstract: The invention comprises compounds of the formula <FORM:1076915/C4-C5/1> and their acid addition salts, where R1 is H or CH3, R is CH3 or CH2CH2OH and n is 1-4. The salts may be hydrochlorides.  The compounds wherein R1 is H and R is CH3 are prepared by reacting 1-methylamino-2-nitro-4-amino benzene with a compound of the formula X(CH2)nCONH2, where X is Cl or Br, and hydrolysing the product.  The compounds wherein R and R1 are both H are prepared by methylating the primary amino group of a compound of the formula <FORM:1076915/C4-C5/2> after first protecting one of the hydrogen atoms on the amino group, liberating the protected hydrogen atom and hydrolysing the CONH2 group.  The compounds wherein R1 is CH3 and R is CH2CH2OH are prepared by reacting 1-amino-2-nitro-4-methylamino benzene with a compound of the formula X(CH2)nCONH2, reacting the product with a compound of the formula XCOOCH2CH2X, hydrolysing the CONH2 group and converting the NHCOOCH2CH2X group to NHCH2CH2OH by alkaline hydrolysis.  The compounds wherein R1 is H and R is CH2CH2OH are prepared by acylating the 4-amino group of 1-amino-2-nitro-4-amino benzene, reacting the product with a compound of the formula XCOOCH2CH2X, hydrolysing the group in the 4-position, reacting the product with a compound of the formula X(CH2)nCONH2, hydrolysing the group in the 4-position and converting the NHCOOCH2CH2X group to NHCH2CH2OH by alkaline hydrolysis.ALSO:The invention comprises compounds of the formula <FORM:1076915/C2/1> and their acid addition salts, where R1 is H or CH3, R is CH3 or CH2CH2OH and n is 1-4. The salts may be hydrochlorides.  The compounds wherein R1 is H and R is CH3 are prepared by reacting 1-methylamino-2-nitro-4-amino benzene with a compound of the formula X(CH2)nCONH2, where X is Cl or Br, and hydrolysing the product.  The compounds wherein R and R1 are both H are prepared by methylating the primary amino group of a compound of the formula <FORM:1076915/C2/2> after first protecting one of the hydrogen atoms on the amino group, liberating the protected hydrogen atom and hydrolysing the CONH2 group.  The compounds wherein R1 is CH3 and R is CH2CH2OH are prepared by reacting 1 - amino - 2 - nitro - 4 - methylaminobenzene with a compound of the formula X(CH2)nCONH2, reacting the product with a compound of the formula XCOOCH2CH2X, hydrolysing the CONH2 group and converting the NHCOOCH2CH2X group to NHCH2CH2OH by alkaline hydrolysis.  The compounds wherein R1 is H and R is CH2CH2OH are prepared by acylating the 4-amino group of 1-amino-2-nitro-4-amino benzene, reacting the product with a compound of the formula XCOOCH2 CH2X, hydrolysing the group in the 4-position, reacting the product with a compound of the formula X(CH2)nCONH2, hydrolysing the group in the 4-position and converting the NHCOOCH2 CH2X group to NHCH2CH2OH by alkaline hydrolysis.ALSO:Compositions for dyeing hair contain a compound of the formula <FORM:1076915/D1-D2/1> or an acid addition salt thereof, e.g. a hydrochloride, where R1 is H or CH3, R is CH3 or CH2CH2OH and n is 1-4.  The dyes are preferably applied from an aqueous solution of pH 3-10.  Other dyes may be present in the composition.