Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
  • C08G73/0206—Polyalkylene(poly)amines
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/12—Quaternary ammonium compounds
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
  • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
  • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
  • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
  • A01N41/04—Sulfonic acids; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
  • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
  • A01N47/44—Guanidine; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/74—Synthetic polymeric materials
  • A61K31/785—Polymers containing nitrogen
  • A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
• • 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
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q15/00—Anti-perspirants or body deodorants
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/005—Antimicrobial preparations
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
  • C08L79/02—Polyamines
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/37—Polymers
  • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C11D3/3723—Polyamines or polyalkyleneimines
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
  • A61K2800/92—Oral administration
• • 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
  • A61Q5/02—Preparations for cleaning the hair

Definitions

• compositions useful in personal applications comprising triclosan as an anti-bacterial agent.
• compositions comprising an anti-bacterial agent.
• WO98/55096 discloses antimicrobial wipes having a porous sheet impregnated with an antibacterial composition containing an active antimicrobial agent.
• JP-09157113-A, JP 09012717-A and JP 07188698 disclose the use of alkyl (C8 to C30), acyl and hydroxyalkyl modified polyethylenimine as antimicrobial agents which are particularly effective with salts of Zn, Cu and Ag.
• anti-microbial compounds for example, as such as those found in antibacterial compositions provide a substantial and broad spectrum reduction in microorganism populations quickly and without problems associated with toxicity and skin irritation.
• Antibacterial activity is assessed against a broad spectrum of microorganisms, including both Gram positive and Gram negative microorganisms.
• the log reduction, or alternatively the percent reduction, in bacterial populations provided by the antibacterial composition correlates to antibacterial activity.
• a log reduction of 3-5 is most preferred, a 1-3 reduction is preferred, whereas a log reduction of less than 1 is least preferred, for a particular contact time, generally ranging from 15 seconds to 5 minutes.
• a highly preferred antibacterial composition exhibits a 3-5 log reduction against a broad spectrum of microorganisms in a short contact time.
• the present invention provides new anti-microbial polyethylenimine compounds. These polymeric and oligomeric compounds are highly active against microbes upon contact, and remain active over a prolonged period of time due in part to their size and polymeric nature which makes them less susceptible to being unintentionally removed. The compounds are also expected to be less harmful upon human contact than other compounds that are more readily absorbed through the skin or made bio-available by dispersion into the environment.
• the present invention provides an antimicrobial ethylenimine polymer or co-polymer, wherein 10 -100% of the nitrogen atoms (also referred to herein as N atoms) of the polymer or co-polymer backbone are substituted by one or more substituents a-d:
• Ci -24 alkyl is not substituted by biguanide, C 3-6 cycloalkyl, -COOM, -COOR where R is an unsubstituted alkyl, -OR where R is H or unsubstituted alkylcarbonyl or -CONR'R unless at least one other of the substituents is also present;
• n and n independently are 1 , 2, 3, 4, 5 or 6; or
• each Q or Q' is independently hydrogen, Ci-i 2 alkyl, phenyl or benzyl; or when attached to a nitrogen atom, R and R', together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring which is uninterrupted or interrupted by -0-, - NH- or -N(C M2 alkyl)-;
• L is a direct bond, C M2 alkylene which is uninterrupted or interrupted by one or more oxygen atoms and which is unsubstituted or substituted one or more times by one or more -OH, Ci -8 alkyl, Ci -24 alkoxy, C 2-24 alkylcarboxy, -NH 2 , -N(H)(Ci -8 alkyl), -N(Ci -8 alkyl) 2 or ammonium salt:
• Ar is C 6 -io aromatic or Ci -9 saturated or unsaturated heterocycle which are unsubstituted or substituted one or more times by one or more halogen, -OH, Ci -24 alkoxy, C 2-24 alkylcarboxy, -COOQ", -CONH 2 , -CON(H)(Ci -8 alkyl), -CON(Ci -8 alkyl) 2 , -NH 2 , -N(H)(Ci -8 alkyl), -N(Ci -8 alkyl) 2 , -SO 3 M, SO 3 H, ammonium salt, phosphonic acid, phosphonate salt, C 1 - 24 alkyl which is unsubstituted or substituted one or more times by one or more halogen, phenyl which is unsubstituted or substituted by one or more times by one or more Ci- ⁇ alkyl, naphthyl, purine, pyridine, pyrimidine, triazine or
• M is a metal cation or an ammonium cation; and when the N atom of the ethylenimine polymer is tetra substituted, it is a cation with a corresponding counter anion.
• Ci -24 alkyl is not substituted by biguanide, -COOM, -COOR where R is an unsubstituted alkyl, or -OR where R is H or unsubstituted alkylcarbonyl, unless at least one other of the substituents is also present;
• an antimicrobial ethylenimine polymer or co-polymer wherein at least a portion of the substituents are Ci -24 alkyl substituted one or more times by one or more halogen or ammonium salt, Ci -24 alkylcarbonyl substituted one or more times by one or more halogen or ammonium salt or at least a portion of the substituents are benzyl, benzoyl or benzyl or benzoyl substituted one or more times by one or more halogens, hydroxyl, C M2 alkyl, C M2 alkoxy or C M2 alkylcarboxy;
• n is a number from 1 to 12;
• an antimicrobial ethylenimine polymer or co-polymer wherein at least a portion of the 10 -100% of the N atoms of the polymer or co-polymer backbone which are substituted are substituted by one or more groups
• p is 1 , 2, 3, 4, 5, or 6.
• At least a portion of the 10 -100% of the N atoms of the antimicrobial ethylenimine polymer or co-polymer backbone which are substituted are substituted by one or more Ci -24 alkyl substituted by at least one group OR and at least one halogen, NR'R, SO 3 M, SO 3 H, ammonium salt or a group of the formulae
• Ci -24 alkyl substituted by at least one group OR and at least one halogen, NR'R, ammonium salt or a group of the formulae
• interrupted alkyl or alkylcarbonyl unsubstituted or substituted one or more times by one or more halogen, -OR, -COOR, -COOM, -SO 3 M, -SO 3 H, ammonium salt or a
• interrupted alkyl or alkylcarbonyl substituted one or more times by one or more halogen, -OR, -COOR, -COOM, -SO 3 M, -SO 3 H, ammonium salt or a group of the NR"
• the present invention provides an antimicrobial ethylenimine polymer or copolymer, wherein at least a portion of the 10 -100% of the N atoms of the polymer or copolymer backbone which are substituted are substituted by one or more
• Y and Y' are independently N, C-R, C-OR or C-NRR' and D and D' are independently R, OR or NRR';
• D and D' are independently R, OR or NRR' wherein R and R' are independently hydrogen, ammonium salt, d- 24 alkyl, d- 24 alkanoyl which are unsubstituted or substituted one or more times by one or more halogen, hydroxyl or ammonium salt; or R
• R' are independently -L- Ar
• L is a direct bond or C M2 alkylene
• Ar is phenyl or phenyl substituted one or more times by one or more halogen, -OH, Ci -24 alkoxy, C 2-24 alkylcarboxy, -COOH, -COOM, -CONH 2 , -CON(H)(Ci -I2 alkyl), -CON(Ci -I2 alkyl) 2 -NH 2 , -N(H)(C M2 alkyl), -N(C M2 alkyl) 2 , ammonium salt, C M2 alkyl or alkyl substituted one or more times by one or more halogen.
• halogen -OH, Ci -24 alkoxy, C 2-24 alkylcarboxy, -COOH, -COOM, -CONH 2 , -CON(H)(Ci -I2 alkyl), -CON(Ci -I2 alkyl) 2 -NH 2 , -N(H)(C M2 alkyl),
• At least a portion of the 10 -100% of the N atoms of the antimicrobial ethylenimine polymer or co-polymer backbone which are substituted are substituted by a group -L-PoIy where Poly is a polymer or oligomer selected from polyether and polysiloxane;
• Ci-9 saturated or unsaturated heterocycle is a monocyclic or polycyclic ring of at least 3 atoms, containing 1-9 carbon atoms which heterocycle may also be ionically charged.
• C-i.g saturated or unsaturated heterocycle is a 5, 6, or 7 membered ring containing 1 , 2 or 3 nitrogen atoms which may be fused to another carbocylic or heterocyclic ring;
• Ci -9 saturated or unsaturated heterocycle is a 5, 6, or 7 membered ring containing 1 , 2 or 3 nitrogen atoms which may be fused to a benzene ring;
• C-i.g saturated or unsaturated heterocycle is a purine, imidazole, pyridine, pyramidine or triazole ring;
• heterocyle may be substituted as described above and which heterocycle may also be ionically charged.
• Alkyl is a straight or branched chain of the specified number of carbon atoms and is for example methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n- nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexadecyl, n-octadecyl or docosanyl and the like.
• Alkenyl is a straight or branched chain of the specified number of carbon atoms containing one or more carbon-carbon double bonds and is for example n-propenyl, n-butenyl, sec- butenyl, n-hexenyl, n-octenyl, n-hexadienyl, n-octadienyl, 2-ethylhexenyl, n-nonenyl, n- decenyl, n-undecenyl, n-dodecenyl, n-tridecenyl, n-tetradecenyl, n-hexadecenyl, n- octadecenyl, n-dodecadienyl, n-tetradecadienyl, n-hexadecadienyl, n-hexadecatrienyl, n- octa
• Alkanoyl is a straight or branched chain of the specified number of carbon atoms which has a carbonyl at the point of attachment.
• An ammonium salt is, for example, unsubstituted ammonium, ammonium substituted 1 , 2 or 3 times by one or more groups selected from C6-ioaryl, and branched alkyl interrupted by one or more oxygen atoms, carbonyl, carboxy or C 6 -ioarylene, and said aryl, alkyl, branched alkyl, interrupted alkyl and interrupted branched alkyl substituted by alkyl, aryl, OH, OAlkyl, OAcyl; plus a corresponding counter anion.
• the ammonium salt may also comprise a ring or polycycle, which ring or polycycle may be substituted.
• Ci- 24 alkylammonium wherein each alkyl group can be the same or different, mono-, di-, or tri- benzyl, mono-, di-, or tri- wherein each alkyl group can be the same or different.
• ammonium salt is di- or tri-substituted ammonium wherein each of the substituents are independently chosen from benzyl and
• the benzyl and groups of the substituted ammonium salts may also be substituted by one or more or branched alkyl, hydroxy, ester, or halogen.
• M is an ammonium cation
• it is for example, unsubstituted ammonium, ammonium substituted 1 , 2, 3 or 4 times by one or more groups selected from alkyl, said alkyl and branched alkyl interrupted by one or more oxygen atoms, C6-ioaryl, C/.garalkyl, and said alkyl, branched alkyl, interrupted alkyl and interrupted branched alkyl, and aryl substituted by alkyl, OH,
• the N atoms of the ethylenimine polymer or co-polymer may be substituted by many of the different substituents described above, a few of the substituents described above or one of the substituents described above.
• a single substituent need not substitute 10% or more of the N atoms of the ethylenimine polymer or co-polymer backbone as long as other substituents described above, also referred to hereafter as inventive substituents, are also present so that at least 10% of the N atoms are substituted with one or more of the inventive substituents.
• a heterocycle such as purine, pyramidine or triazine heterocycle unsubstituted or substituted by one or more Ci -8 alkyl, alkyl amine, aryl amine, phenyl, benzyl, substituted phenyl or benzyl, acyloxy groups, carboxy acid, acid salt and/or ester groups.
• inventive substituents are selected from the group consisting of benzyl substituted 1-5 times by F, Cl, Br or I or any combination of F, Cl, Br or I;
• Y is CR or N
• Y, Y' and Y" are C or N and R is as defined above.
• at least a portion of the 10 -100% of the N atoms of the an antimicrobial ethylenimine polymer or co-polymer backbone are substituted by an alkyl group which is substituted by at least two different groups selected from OR, COOM, halogen, CONR'R, NR'R, SO 3 M, SO 3 H, phosphonic acid, phosphonate salt, ammonium salt or a group of the formulae NR"
• the ethylenimine polymer or co-polymer may be substituted by moieties that provide different activities.
• the polymer may bear substituents that render the polymer anti-bacterial and other substituents that render the polymer anti-fungal.
• a single ethylenimine polymer, co-polymer or oligomer comprises at least two different substituents wherein each of the substituents provides a different anti-microbial activity, for example, the N atoms of the polymer bear two different substituents, each substituent conferring a different activity.
• a single N atom substituent bears at least two different groups conferring different activities, for example, N atoms are substituted by an alkyl group which alkyl group is substituted by two moieties, one moiety conferring anti-bacterial activity and another moiety conferring anti-fungal activity.
• At least two different inventive ethylenimine polymers, co-polymer or oligomer are blended.
• an inventive ethylenimine polymer, co-polymer or oligomer is blended with another anti-microbial compound.
• substituents not described above for example, simple alkyl substituents such as Ci -24 alkyl or Ci -24 alkyl substituted by hydroxy, carboxy or carboxylic ester groups may also be present as additional substituents on the N atoms of the ethylenimine polymer or co-polymer. Remaining nitrogen atoms may be unsubstituted or substituted by C 1 - 24 alkyl or said alkyl substituted by -OR, COOR, COOM wherein R and M are as described above.
• the invention therefore includes ethylenimine polymers or copolymers wherein 10-100%, especially 10- 99%, of the nitrogen atoms carry an inventive substituent, while the remaining nitrogen atoms, e.g. 1-90%, are unsubstituted, or are substituted by Ci -24 alkyl or said alkyl substituted by -OR, COOR, COOM wherein R and M are as described above, or a portion is unsubstituted while the rest is substituted by Ci -24 alkyl or said alkyl substituted by -OR, COOR, COOM wherein R and M are as described above.
• the invention also pertains to an antimicrobial ethylenimine polymer or copolymer according to claim 1 , wherein 10-99% of the N atoms of the ethylenimine polymer or co-polymer backbone are substituted as described above and at least 1 % of the N atoms of the ethylenimine polymer or co-polymer backbone are substituted by Ci -24 alkyl or said alkyl substituted by -OR, COOR, COOM wherein R and M are as described above.
• a portion of the N atoms of the polymer or co-polymer backbone can be substituted by benzyl, a portion by chlorobenzyl and a portion substituted by both benzyl and chlorobenzyl.
• 10% or more of the N atoms of the polymer or co-polymer backbone can be substituted by an alkyl chain substituted by a hydroxy group and an ammonium cation and a portion of the remaining backbone N atoms by a simple alkyl.
• the substituted ethylenimine polymers or co-polymers of the present invention are readily prepared by substituting the N atoms of a pre-existing polymer via known reactions as discussed below, or by substituting the N atoms of ethylenimine monomer or oligomers prior to performing a subsequent polymerization.
• Such pre-existing polymers are commercially available as are "prepolymers", that is ethylenimine monomer or oligomers that can be polymerized.
• the polymer or co-polymer prior to substitution has a molecular weight in the range of 300 to 50000, typically 400 to 50,000, for example 400 to 5,000, and can be branched or unbranched.
• the polymer may be also be inherently crosslinked, i.e., crosslinked through reactions of ethylenimine based materials, or cross-linked by agents such as epichlorohydrin, diepoxides, epoxy resins or anhydrides.
• N atoms of an existing ethylenimine polymer, co-polymer or oligomer to be substituted according to the invention may be mono-, di-, or tri-substituted amines depending on the amount of branching and crosslinking.
• Each N atom may therefore bear one or more of the inventive or non-inventive substituents and the polymer or co-polymer may be cationic.
• N atoms of an ethylenimine polymer, co-polymer or oligomer are substituted by any of the well known substitution reactions of amines.
• amines can be alkylated, arylated or substituted by heterocycles via reaction with alkyl, aryl or heterocyclic halides, sulfonates, epoxides, etc. under the appropriate conditions, typically in the presence of a base. Alkylation of amines also occurs via addition across a double bond as in reactions with vinyl esters, amides, nitriles sulphones etc.
• Amines can be acylated by reaction with acid halides, esters, anhydrides, carboxylic acids etc. A variety of metal catalyzed reactions, such as Heck and Suzuki reactions, are also known to derivatise amines.
• the reaction conditions will determine the amount of N atoms of the polymer or co-polymer backbone substituted.
• the amount of alkyl halide used in the reaction represents an upper limit of the amount of alkylating reagent that can be incorporated.
• the N atoms of the polymer or co-polymer backbone may be substituted more than once under the reaction conditions.
• the amount of substituting reagent used in such a reaction will typically be chosen to provide a substitution ratio the range of 0.2 to 2 molar equivalent of substituent per polymer containing N atom.
• the alkyl halides are items of commerce or readily prepared via known means.
• benzyl amino moieties included secondary and primary benzyl amino.
• the antimicrobial ethylenimine polymers or co-polymers of the invention exhibit pronounced antimicrobial action, for example, against pathogenic gram-positive and gram-negative bacteria and against bacteria of the skin flora, and also against yeasts and molds. They are accordingly suitable for disinfection, deodorisation, and for general and antimicrobial treatment of the skin and mucosa and of integumentary appendages (hair), for example, for the disinfection of hands and wounds.
• the invention accordingly relates also to a personal care preparation comprising at least one of the inventive antimicrobial ethylenimine polymer or co-polymer and cosmetically tolerable carriers or adjuvants.
• the personal care preparation according to the invention contains from 0.01 to 15 % by weight, for example, from 0.1 to 10 % by weight, based on the total weight of the inventive composition, of an inventive antimicrobial ethylenimine polymer or co-polymer, and cosmetically tolerable adjuvants.
• the personal care preparation comprises, in addition to the antimicrobial ethylenimine polymer or co-polymer further constituents, for example sequestering agents, colourings, perfume oils, thickening or solidifying agents (consistency regulators), emollients, UV-absorbers, skin protective agents, antioxidants, additives that improve the mechanical properties, such as dicarboxylic acids and/or aluminium, zinc, calcium or magnesium salts of Ci 4 -C 22 fatty acids, and, optionally, preservatives.
• further constituents for example sequestering agents, colourings, perfume oils, thickening or solidifying agents (consistency regulators), emollients, UV-absorbers, skin protective agents, antioxidants, additives that improve the mechanical properties, such as dicarboxylic acids and/or aluminium, zinc, calcium or magnesium salts of Ci 4 -C 22 fatty acids, and, optionally, preservatives.
• the personal care preparation according to the invention may be in the form of a water-in-oil or oil-in-water emulsion, an alcoholic or alcohol-containing formulation, a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, a gel, a solid stick or an aerosol formulation.
• the cosmetically tolerable adjuvant contains preferably from 5 to 50 % of an oil phase, from 5 to 20 % of an emulsifier and from 30 to 90 % water.
• the oil phase may comprise any oil suitable for cosmetic formulations, for example one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol.
• Preferred mono- or poly-ols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
• Cosmetic formulations according to the invention are used in various fields. There come into consideration, for example, the following preparations: skin-care preparations, e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes, bath preparations, e.g. liquid (foam baths, milks, shower preparations) or solid bath preparations, e.g. bath cubes and bath salts; skin-care preparations, e.g. skin emulsions, multi-emulsions or skin oils; cosmetic personal care preparations, e.g. facial make-up in the form of day creams or powder creams, face powder (loose or pressed), rouge or cream make-up, eye-care preparations, e.g.
• skin-care preparations e.g. skin-washing and cleansing preparations in the form of tablet-form or liquid soaps, synthetic detergents or washing pastes
• bath preparations e.g. liquid (foam baths, milks, shower preparations
• eyeshadow preparations mascaras, eyeliners, eye creams or eye-fix creams
• lip-care preparations e.g. lipsticks, lip gloss, lip contour pencils, nail-care preparations, such as nail varnish, nail varnish removers, nail hardeners or cuticle removers
• intimate hygiene preparations e.g. intimate washing lotions or intimate sprays
• foot-care preparations e.g.
• foot baths foot powders, foot creams or foot balsams, special deodorants and antiperspirants or callus-removing preparations
• light-protective preparations such as sun milks, lotions, creams or oils, sun-blocks or tropicals, pre-tanning preparations or after-sun preparations
• skin-tanning preparations e.g. self-tanning creams
• depigmenting preparations e.g. preparations for bleaching the skin or skin-lightening preparations
• insect-repellents e.g.
• insect-repellent oils, lotions, sprays or sticks deodorants, such as deodorant sprays, pump-action sprays, deodorant gels, sticks or roll-ons; antiperspirants, e.g. antiperspirant sticks, creams or roll-ons; - preparations for cleansing and caring for blemished skin, e.g. synthetic detergents (solid or liquid), peeling or scrub preparations or peeling masks; hair-removal preparations in chemical form (depilation), e.g. hair-removing powders, liquid hair-removing preparations, cream- or paste-form hair-removing preparations, hair- removing preparations in gel form or aerosol foams; - shaving preparations, e.g.
• fragrance preparations e.g. fragrances (eau de Cologne, eau de toilette, eau de perfume, perfume de toilette, perfume), perfume oils or perfume creams
• - dental care, denture-care and mouth-care preparations e.g. toothpastes, gel toothpastes, tooth powders, mouthwash concentrates, anti-plaque mouthwashes, denture cleaners or denture fixatives
• cosmetic hair-treatment preparations e.g. hair-washing preparations in the form of shampoos and conditioners, hair-care preparations, e.g.
• pretreatment preparations hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-structuring preparations, e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair-setting preparations, hair foams, hairsprays, bleaching preparations, e.g. hydrogen peroxide solutions, lightening shampoos, bleaching creams, bleaching powders, bleaching pastes or oils, temporary, semi-permanent or permanent hair colorants, preparations containing self- oxidising dyes, or natural hair colorants, such as henna or camomile.
• hair-structuring preparations e.g. hair-waving preparations for permanent waves (hot wave, mild wave, cold wave), hair-straightening preparations, liquid hair-setting preparations, hair foams, hairsprays, bleaching preparations, e.g. hydrogen peroxide solutions, lightening shampoos, bleaching
• An antimicrobial soap has, for example, the following composition: 0.01 to 5 % by weight of the instant antimicrobial polymer, 0.3 to 1 % by weight titanium dioxide, 1 to 10 % by weight stearic acid, soap base ad 100 %, e.g. a sodium salt of tallow fatty acid or coconut fatty acid, or glycerol.
• a shampoo has, for example, the following composition:
• useful surfactants include, but are not limited to, polyoxyethylene-based surface-active substances, including polyoxyethylene sorbitan tetraoleate (PST), polyoxyethylene sorbitol hexaoleate (PSH), polyoxyethylene 6 tridecyl ether, polyoxyethylene 12 tridecyl ether, polyoxyethylene 18 tridecyl ether, TWEEN RTM surfactants, TRITON RTM surfactants, and the polyoxyethlene-polyoxypropylene copolymers such as the PLURONIC RTM and POLOXAMER RTM product series (from BASF).
• PST polyoxyethylene sorbitan tetraoleate
• PSH polyoxyethylene sorbitol hexaoleate
• polyoxyethylene 6 tridecyl ether polyoxyethylene 12 tridecyl ether
• polyoxyethylene 18 tridecyl ether polyoxyethylene 18 tridecyl ether
• TWEEN RTM surfactants TRITON
• the inorganic or organic substrate is, for example, a metal or metal alloy, a thermoplastic, elastomeric, inherently crosslinked or crosslinked polymer, a ceramic material or a glass.
• compositions of the instant invention are found, among other places, on the surfaces of:
• a method for protecting skin, mucosa and integumentary appendages against the action of microbes which comprises applying a preparation comprising an effective amount of the present polymer or copolymer;
• a method for cleaning and disinfecting hard surfaces which comprises applying a preparation comprising an effective amount of the present polymer or copolymer;
• RX is the halide used RX per monomer is the ratio of halide used for each ethylenimine monomer unit
• Example 2 Using a variant of the general procedure of Example 1 or 2, three different polyethylenimine polymers with molecular weights of 800, 2,000 and/or 25,000 are substituted with the following substituents using from 0.25 to 2 equivalents of the appropriate halides (RX) per monomer to generate the corresponding N-substituted polymer and the resulting polymers are tested for activity against bacteria, e. coloi, s. aureus; fungi, a. pull, p.funic, a. niger, adhesion of microbes or biofilm accumulation. All compounds are effective in at least one test; some are effective in more than one or all of the tests.
• RX halides
• polyethylenimine polymers are substituted with the following pairs of substituents, using 0.5 or 1 equivalent of the appropriate halides (RX) per monomer, the substituent halides are added in a 1 :1 ratio relative to each other in each example, to generate the corresponding N-substituted polymer and the resulting polymers are tested for activity against bacteria, e. coloi, s. aureus; fungi, a. pull, p.funic, a. niger, adhesion of microbes or biofilm accumulation. All compounds are effective in at least one test; some are effective in more than one or all of the tests.
• RX halides
• Fungicidal activity is tested according to trivial modifications of the standard EN 12175 test method.
• a fungal spore suspension with a spore cell count of about 10 6 cfu/ml is contacted with appropriate concentrations of the specific substances and the residual spore cell count is determined after incubation times of 30 and 60 min. at room temperature under continuous stirring.
• Penicillium funiculosum, Aspergillus niger and Aureobasidium pullulans are tested as important mold strains. The resulting cell count reduction is compared to a water control.
• Polyethylenimine samples for example functionalized by Quab 342, Quab 426, i.e.,
• Biofilm inhibition The ability of the compounds for inhibiting the initial stages of biofilm formation is tested in a microplate based screening assay. Standard test specimen of polycarbonate are contacted with compound solutions in water or ethanol at a concentration of 0.5% for ⁇ A hour for the compounds to form a film on the pin surface. The pins are then dried at room temperature under laminar flow. The coated pins are contacted with a bacterial inoculum of Staphylococcus aureus at a cell count of 10 4 - 10 5 cfu/ml in a microplate and a biofilm is allowed to form on the plastic surface over 24 hours.
• Loosely attached cells are then rinsed off in a couple of rinsing steps, then the biofilm on the surface is removed by ultrasonic treatment.
• the eluted cells are transferred into new microplates in Caso broth and growth is followed by measurement of optical density at 620 nm over 24 hours. The results are evaluated as growth curves of the eluted cells over 24 hours incubation time in comparison to the growth curve of untreated samples.
• Polyethylenimine samples for example functionalized by Quab 342, Quab 426, benzyl bromide and hexyl bromide, show full biofilm inhibition in the screening assay described above.

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• 2007
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