公开(公告)号：DE1617693A1

公开(公告)日：1971-04-22

申请号：DE1617693

申请日：1966-04-23

Applicant: OREAL

Inventor： KALAPISSIS GEORG ,  BUGAUT ANDRE

IPC: A61K20060101 ,  A61K8/41 ,  A61Q5/06 ,  C07C20060101 ,  C09B51/00 ,  D06P1/19 ,  D06P3/14 ,  C07C101/44

Abstract: The invention comprises compounds of the formula 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 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 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 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 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.