公开(公告)号：DE1569814A1

公开(公告)日：1969-08-14

申请号：DE1569814

申请日：1966-04-25

Applicant: OREAL

Inventor： KALOPISSIS DR GEORG ,  BUGAUT ANDRE

IPC: C07C20060101 ,  C07C215/16 ,  C09B51/00 ,  D06P3/14

Abstract: 1,138,171. Nitro dyes. L'OREAL. 26 April, 1966 [26 April, 1965], No. 18289/66. Heading C4P. [Also in Division D1] 1 - Amino - 2 - nitro - 4 - (# - hydroxyethyl)- methylamino benzene is prepared by nitrating 1 - acetamido - 4 - (# - hydroxyethyl) - methylamino-benzene and de-acetylating the product. 1 - Methylamino - 2 - nitro - 4 - (# - hydroxyethyl)-methylamino is prepared by methylating the l-amino group of the above product after first protecting one of the hydrogen atoms of the said amino group and then removing the protecting group, e.g. a toxyl group. 1-(#- Hydroxyethyl) - amino - 2 - nitro - 4 - (#- hydroxyethyl) - methylamino benzene is prepared by reacting the first product above with chloroethyl-chloroformate and hydrolysing the product.

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.

公开(公告)号：IT8268175D0

公开(公告)日：1982-10-07

申请号：IT6817582

申请日：1982-10-07

Applicant: OREAL

Inventor： BUGAUT ANDRE ,  BOROWIAK HERVE

IPC: A61K8/41 ,  A61Q5/06 ,  A61Q5/10 ,  C07C215/76 ,  C07C217/84 ,  C07D263/22 ,  C09B51/00 ,  C09B57/00 ,  D06P3/08 ,  D06P3/18 ,  A61K

Abstract: There are described dyeing compositions for keratin fibres, and in particular for human hair, containing a dyestuff of the formula: (I) in which A denotes an alkylene group, an alkylene group substituted by one or more OH groups, or an alkylene group interrupted by a hetero-atom such as oxygen or by an -NH- group, R1 and R2, which are identical or different, denote hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl, or R1 and R2 can together form a heterocyclic ring chosen from among piperidino or morpholino groups, Y denotes alkoxy or NO2, R denotes hydrogen or lower alkyl, and if Y denotes alkoxy, Z denotes NO2 and is located in the para-position to the amine group, and if Y denotes NO2, (a) Z denotes alkoxy or OH and is located in the para-position to the NO2 group, or alternatively (b) Z denotes OH and is located in the para-position to the amine group, and also their cosmetically acceptable salts. Many of these dyestuff are novel.

公开(公告)号：DE1617698A1

公开(公告)日：1971-04-22

申请号：DE1617698

申请日：1966-07-29

Applicant: OREAL

Inventor： KALOPISSIS GEORG DR ,  BUGAUT ANDRE

IPC: A61K8/00 ,  A01J25/11 ,  A01J25/16 ,  A61K8/40 ,  A61K8/41 ,  A61K8/49 ,  A61Q5/06 ,  A61Q5/10 ,  C07C215/14 ,  C07C215/16 ,  C07C311/00 ,  C07C311/15 ,  C07D209/48 ,  C07D295/13 ,  C09B51/00 ,  D06P3/14

Abstract: Hair-colouring compositions contain in aqs. soln. at least one nitroparaphenylenediamine dye of formula: (in which R, R' and R" are H, lower alkyl or lower hydroxyalkyl, and R''' is where the amino group may be quaternized, and R1 and R2 are H, lower alkyl or lower hydroxyalkyl, or form a heterocyclic ring with the adjacent N-atom, and n is 2-6 when the NO2 group is ortho to the NR'R" radical, one of R' and R" can be H; when the NO2 group is ortho to the NR'R''' radical and R is H, R1 and R2 are not both ethyl and R' and R" are not both H; when the NO2 group is ortho to the NR'R" radical and R is H, R1 and R2 cannot both be ethyl and R" is not methyl when R' is H. When NO2 is meta to NRR''' only of R' may be H.) The compositions contains 0.1-3.8% dye and have a pH of 6-10. They are applied at room temp. for 5-30 minutes, the hair being subsequently rinsed, shampooed and dried. The dyes show great resistance to light and washing, and they can be used in combination with thickeners, detergents, solvents and lacquers.

公开(公告)号：BR8200142A

公开(公告)日：1982-11-03

申请号：BR8200142

申请日：1982-01-12

Applicant: OREAL

Inventor： BUGAUT ANDRE ,  JUNINO ALEX ,  VANDENBOOSCHE JEAN JACQUES

IPC: A61K8/00 ,  A61K20060101 ,  A61K8/34 ,  A61K8/40 ,  A61K8/41 ,  A61Q5/06 ,  A61Q5/10 ,  C07C20060101 ,  C09B20060101 ,  C09B51/00 ,  C09B53/00 ,  C09B57/00 ,  C09B67/42 ,  D06P3/02 ,  D06P3/08 ,  D06P3/14 ,  A61K7/13 ,  C07C103/52

公开(公告)号：DE1569815A1

公开(公告)日：1970-10-22

申请号：DE1569815

申请日：1966-04-25

Applicant: OREAL

Inventor： KALOPISSIS DR GEORG ,  BUGAUT ANDRE

IPC: C07C20060101 ,  C07C215/16 ,  C09B51/00 ,  D06P3/14

Abstract: 1,138,171. Nitro dyes. L'OREAL. 26 April, 1966 [26 April, 1965], No. 18289/66. Heading C4P. [Also in Division D1] 1 - Amino - 2 - nitro - 4 - (# - hydroxyethyl)- methylamino benzene is prepared by nitrating 1 - acetamido - 4 - (# - hydroxyethyl) - methylamino-benzene and de-acetylating the product. 1 - Methylamino - 2 - nitro - 4 - (# - hydroxyethyl)-methylamino is prepared by methylating the l-amino group of the above product after first protecting one of the hydrogen atoms of the said amino group and then removing the protecting group, e.g. a toxyl group. 1-(#- Hydroxyethyl) - amino - 2 - nitro - 4 - (#- hydroxyethyl) - methylamino benzene is prepared by reacting the first product above with chloroethyl-chloroformate and hydrolysing the product.

公开(公告)号：DE1619612A1

公开(公告)日：1970-09-17

申请号：DE1619612

申请日：1966-04-23

Applicant: OREAL

Inventor： KALOPISSIS 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.

公开(公告)号：IT1157065B

公开(公告)日：1987-02-11

申请号：IT6817582

申请日：1982-10-07

Applicant: OREAL

Inventor： BUGAUT ANDRE ,  BOROWIAK HERVE

IPC: A61K8/41 ,  A61Q5/06 ,  A61Q5/10 ,  C07C215/76 ,  C07C217/84 ,  C07D263/22 ,  C09B51/00 ,  C09B57/00 ,  D06P3/08 ,  D06P3/18 ,  A61K

Abstract: There are described dyeing compositions for keratin fibres, and in particular for human hair, containing a dyestuff of the formula: (I) in which A denotes an alkylene group, an alkylene group substituted by one or more OH groups, or an alkylene group interrupted by a hetero-atom such as oxygen or by an -NH- group, R1 and R2, which are identical or different, denote hydrogen, alkyl, monohydroxyalkyl or polyhydroxyalkyl, or R1 and R2 can together form a heterocyclic ring chosen from among piperidino or morpholino groups, Y denotes alkoxy or NO2, R denotes hydrogen or lower alkyl, and if Y denotes alkoxy, Z denotes NO2 and is located in the para-position to the amine group, and if Y denotes NO2, (a) Z denotes alkoxy or OH and is located in the para-position to the NO2 group, or alternatively (b) Z denotes OH and is located in the para-position to the amine group, and also their cosmetically acceptable salts. Many of these dyestuff are novel.

公开(公告)号：DE1543807A1

公开(公告)日：1973-07-26

申请号：DE1543807

申请日：1966-04-20

Applicant: OREAL

Inventor： BUGAUT ANDRE ,  GHILARDI GIULIANA

IPC: A61K20060101 ,  A61K38/43 ,  C07C20060101 ,  C09F20060101 ,  D06P3/04 ,  D06P3/14 ,  C07C91/44

Abstract: The invention comprises a substituted p-phenylene diamine of formula prepared by reducing 1-methoxy-2-nitro-4,6-dimethyl-benzene to 1-methoxy-2-amino-4,6-dimethylbenzene, nitrating this to introduce a nitro group into the 5-position after first protecting the 2-amino group, liberating the 2-amino group and reducing the 5-nitro group. A preferred method involves reducing and acetylating 1-methoxy-2-nitro-4,6-dimethyl benzene to produce 1-methoxy-2-acetamido-4,6-dimethyl benzene, then nitrating with nitric acid to give 1 - methoxy - 2 - acetamide - 5 - nitro-4, 6-dimethyl benzene, de-acetylating the product with HCl and reducing the 5-nitro group. The substance is utilizable in hair dyeing (see Division D1).ALSO:Keratinic fibres, particularly human hair, are dyed using a composition containing as essential component 1-methoxy-2,5-diamino-4,6-dimethyl benzene in the presence of an oxidising agent, e.g. H2O2. The composition may also contain other dyestuffs, thickening agents and/or surface active agent and preferably has a pH of 8-10.

公开(公告)号：DE1667956A1

公开(公告)日：1971-11-04

申请号：DE1667956

申请日：1966-04-20

Applicant: OREAL

Inventor： BUGAUT ANDRE ,  GHILARDI GIULIANA

IPC: A61K20060101 ,  A61K38/43 ,  C07C20060101 ,  C09F20060101 ,  D06P3/04 ,  D06P3/14

Abstract: The invention comprises a substituted p-phenylene diamine of formula prepared by reducing 1-methoxy-2-nitro-4,6-dimethyl-benzene to 1-methoxy-2-amino-4,6-dimethylbenzene, nitrating this to introduce a nitro group into the 5-position after first protecting the 2-amino group, liberating the 2-amino group and reducing the 5-nitro group. A preferred method involves reducing and acetylating 1-methoxy-2-nitro-4,6-dimethyl benzene to produce 1-methoxy-2-acetamido-4,6-dimethyl benzene, then nitrating with nitric acid to give 1 - methoxy - 2 - acetamide - 5 - nitro-4, 6-dimethyl benzene, de-acetylating the product with HCl and reducing the 5-nitro group. The substance is utilizable in hair dyeing (see Division D1).ALSO:Keratinic fibres, particularly human hair, are dyed using a composition containing as essential component 1-methoxy-2,5-diamino-4,6-dimethyl benzene in the presence of an oxidising agent, e.g. H2O2. The composition may also contain other dyestuffs, thickening agents and/or surface active agent and preferably has a pH of 8-10.