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US 6,916,778 B1Granted
UV absorbers with affinity for textile fiber
AssigneeBASF SE
InventorsJürgen Detering, Werner Bertleff, Gerhard Wagenblast, Christian Ott, Elisabeth Kappes, Thorsten Habeck
Life of this patent
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Abstract
The invention relates to the use of compounds (A) with at least one structural unit of formula (I), wherein X represents groups of formula —CR1═CR2— or a carbonyl group C═O, R1 and R2 meaning hydrogen or essentially organic radicals, Z means essentially organic radicals, n means a number from 0 to 3 and p means a number from 0 to 5, as UV absorbers with an affinity for textile fibres, for protecting the human skin from harmful UV radiation and for protecting dyed textile materials from fading.
Claims8
A method of treating textile fibers, comprising:
- imparting UV light protection properties to textile fibers by treating the textile fibers with a compound having UV light absorption properties that contains at least one structural unit of formula (II)
- and that adheres to the textile fibers, wherein
- X is a group of the formula —CR1═CR2— or a carbonyl group C═O, where R1 and R2 are independently hydrogen, C1- to C8-alkyl, C1- to C8-alkoxy, C1- to C8-alkoxycarbonyl, C1- to C8-acyloxy, carboxyl, cyano, nitro, fluorine, chlorine, bromine, sulfonyl, C1- to C8-alkylsulfonyl or phenyl which may be substituted by up to 3 radicals selected from the group consisting of C1- to C8-alkyl, C1- to C8-alkoxy, C1- to C8-alkoxycarbonyl, C1- to C8-acyloxy, carboxyl, cyano, nitro, chlorine, bromine, sulfonyl and C1- to C8-alkylsulfonyl, where R1 optionally is the group —NQ—CO—, which is bonded with its carbonyl carbon atom to the ortho position of the adjacent phenyl ring to form a benzopyrrolidone system, and in which Q is hydrogen or a C1-C8-alkyl radical;
- Z is a substituent selected from the group consisting of C1- to C8-alkyl, C1- to C8 alkoxy, C1- to C8-alkoxycarbonyl, C1- to C8-acyloxy, carboxyl, cyano, nitro, fluorine, chlorine, bromine, sulfonyl, C1- to C8-alkylsulfonyl, amino, mono- or di-C1- to C8-alkylamino, carboxamido (with or without one or two C1- to C8-alkyl groups on the amide nitrogen), hydroxyl and saturated or unsaturated five- and six-membered heterocyclic radicals, which may be benzofused, and any two adjacent Z substituents may also form a saturated or unsaturated five- or six-membered ring, and in the case of p=0 an ortho-disposed carboxyl group may be combined with the carbonyl group present and a nitrogen atom attached directly to this carbonyl group to form a cyclic imide;
- n is 0, 1, 2 or 3 and p is 0, 1, 2, 3, 4 or 5;
- Y is the radical of an aliphatic, cycloaliphatic, or mixed aliphatic-aromatic group which has at least m′ primary and/or secondary amino groups, m′ hydroxyl groups or together at least m′ primary and/or secondary amino groups and hydroxyl groups, which is capable of forming amide or ester bonds with the structural unit of the formula (I)
- and the tertiary and/or free primary and/or secondary nitrogen atoms present in the compounds of radical Y optionally being quaternized;
- and
- m is the number of structural units (I) bonded to primary and/or secondary amino groups and hydroxyl groups and accounts for from 10 to 100% of the number of these m′ groups which range from 1 to 200,
- wherein the group Y is selected from the group consisting of
- (a) an aliphatic or cycloaliphatic oligoamine selected from the group consisting of diethylenetriamine, dipropylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N(2-aminoethyl)-1,3-propanediamine, N,N-dimethylethanolamine, diethanolamine, triethanolamine, 3-dimethylamino-1-propanol, N-(2-aminoethyl) ethanol amine, 3-(dimethylamino) propylamine, N,N′-bis(3-aminopropyl)-1,2-ethylenediamine, N,N,N′,N′-tetrakis(3-aminopropyl)-1,2-ethylenediamine, N,N,N′,N′-tetrakis[3-(C1- to C4-alkylamino)propyl]-1,2-ethylenediamine, N,N′-bis(3-aminopropyl)piperazine and N,N′-bis[3-(C1- to C4-alkylamino)propyl]piperazine;
- (b) a polyethyleneimine of the formula (III)
- which has an average molecular weight (MW) ranging from 200 to 1,000,000 and wherein radicals R3 to R8 are independently hydrogen, linear or branched C1- to C20-alkyl, -alkoxy, -polyoxyethylene, -hydroxyalkyl, -(alkyl)carboxy, -phosphonoalkyl, -alkylamino radicals, C2- to C20-alkenyl radicals or C6- to C20-aryl, -aryloxy, -hydroxyaryl, -arylcarboxy or -arylamino radicals which optionally are substituted, and R4 and R5 are each additionally polyethyleneimine polymer chains, and x, y and z are independently 0 or an integer,
- (c) a polyamidoamine which has an average molecular weight (MW) ranging from 500 to 100,000,000, which is prepared by reaction of C4- to C10-dicarboxylic acids with poly(C2- to C4-alkylene)polyamines having from 3 to 20 basic nitrogen atoms in the molecule and which has at least m′ primary and/or secondary amino groups which form amide bonds with the structural unit (I);
- (d) a polyamine of formula (IV)
- R9R10N—[CHqH2q—NR11—]r—CqH2q—NR9R10 (IV)
- which has an average molecular weight (MW) ranging from 100 to 100,000,000 and wherein the radicals R9 to R11 are independently hydrogen, linear or branched C1- to C20-alkyl, -alkoxy, -polyoxyethylene, -hydroxyalkyl, -(alkyl)carboxy, -phosphonoalkyl, -alkylamino radicals, C2- to C20-alkenyl radicals or C6- to C20-aryl, -aryloxy, -hydroxyaryl, -arylcarboxy or -arylamino radicals which optionally are substituted, q is an integer from 2 to 6 and r is an integer, wherein the alkylamino radicals mentioned are optionally continued in the alkyl moiety;
- and
- (e) a polyvinylamine of formula (V)
- which has an average molecular weight (MW) ranging from 300 to 100,000,000 and wherein R12 to R16 are independently hydrogen, linear or branched C1- to C20alkyl, -alkoxy, -polyoxyethylene, -hydroxyalkyl, -(alkyl)carboxy, -phosphonoalkyl, -alkylamino radicals, C2- to C20-alkenyl radicals or C6- to C20-aryl, -aryloxy, -hydroxyaryl, -arylcarboxy or -arylamino radicals which optionally are substituted, and R15 is additionally a formamidyl radical, s is an integer and t is 0 or an integer.
17 more elements
A method of treating textile fibers, comprising:
- imparting UV light protection properties to textile fibers by treating the textile fibers with a compound having UV light absorption properties that contains at least one structural unit of formula (II)
- and that adheres to the textile fibers, wherein
- X is a group of the formula —CR1═CR2—, where R1 and R2 are independently hydrogen, C1- to C8-alkyl, C1- to C8-alkoxy, C1- to C8-alkoxycarbonyl, C1- to C8-acyloxy, carboxyl, cyano, nitro, fluorine, chlorine, bromine, sulfonyl, C1- to C8-alkylsulfonyl or phenyl which may be substituted by up to 3 radicals selected from the group consisting of C1- to C8-alkyl, C1- to C8-alkoxy, C1- to C8-alkoxycarbonyl, C1- to C8-acyloxy, carboxyl, cyano, nitro, chlorine, bromine, sulfonyl and C1- to C8-alkylsulfonyl, where R1 optionally is the group —NQ—CO—, which is bonded with its carbonyl carbon atom to the ortho position of the adjacent phenyl ring to form a benzopyrrolidone system, and in which Q is hydrogen or a C1-C8-alkyl radical;
- Z is a substituent selected from the group consisting of C1- to C8-alkyl, C1- to C8 alkoxy, C1- to C8-alkoxycarbonyl, C1- to C8-acyloxy, carboxyl, cyano, nitro, fluorine, chlorine, bromine, sulfonyl, C1- to C8-alkylsulfonyl, amino, mono- or di-C1- to C8-alkylamino, carboxamido (with or without one or two C1- to C8-alkyl groups on the amide nitrogen), hydroxyl and saturated or unsaturated five- and six-membered heterocyclic radicals, which may be benzofused, and any two adjacent Z substituents may also form a saturated or unsaturated five- or six-membered ring, and in the case of p=0 an ortho-disposed carboxyl group may be combined with the carbonyl group present and a nitrogen atom attached directly to this cyclic group to form a cyclic imide;
- n is 1, 2 or 3 and p is 0, 1, 2, 3, 4 or 5;
- Y is the radical of an aliphatic, cycloaliphatic, or mixed aliphatic-aromatic group which has at least me primary and/or secondary amino groups, which are capable of forming amide bonds with the structural unit of the formula (I)
- and the tertiary and/or free primary and/or secondary nitrogen atoms present in the compounds of radical Y optionally being quaternized;
- and
- m is the number of structural units (I) bonded to primary and/or secondary amino groups and hydroxyl groups and accounts for from 10 to 100% of the number of these m′ groups which range from 1 to 200, wherein
- Y is the radical of a compound selected from the group consisting of;
- (a) an aliphatic or cycloaliphatic oligoamine selected from the group consisting of diethylenetriamine, dipropylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-2-aminoethyl)-1,3-propanediamine, 3-(dimethylamino)propylamine, N,N′-bis(3-aminopropyl)-1,2-ethylenediamine, N,N,N′,N′-tetrakis(3-aminopropyl)-1,2-ethylenediamine, N,N,N′,N′-tetrakis[3-(C1- to C4-alkylamino)propyl]-1,2-ethylenediamine, N,N′-bis(3-aminopropyl)piperazine and N,N′-bis[3-(C1- to C4-alkylamino)propyl]piperazine;
- (b) a polyethyleneimine of the formula (III)
- which has an average molecular weight (MW) ranging from 200 to 1,000,000 and wherein radicals R3 to R8 are independently hydrogen, linear or branched C2- to C20-alkyl, -alkoxy, (alkyl)carboxy, -phosphonoalkyl, -alkylamino radicals, C2- to C20-alkenyl radicals or C6- to C20-aryl, -aryloxy, -arylcarboxy or -arylamino radicals which optionally are substituted, and R4 and R5 are each additionally polyethyleneimine polymer chains, and x, y and z are independently 0 or an integer;
- (c) a polyamidoamine which has an average molecular weight (MW) ranging from 500 to 100,000,000, which is prepared by reaction of C4- to C10-dicarboxylic acids with poly(C2- to C4-alkylene)polyamines having from 3 to 20 basic nitrogen atoms in the molecule and which has at least m′ primary and/or secondary amino groups which form amide bonds with the structural unit (I);
- (d) a polyamine of formula (IV)
- R9R10N—[CqH2q—NR11—]r—CqH2q—NR9R10 (IV)
- which has an average molecular weight (MW) ranging from 100 to 100,000,000 and wherein the radicals R9 to R11 are independently hydrogen, linear or branched C1- to C20-alkyl, -alkoxy, -(alkyl)carboxy, -phosphonoalkyl, -alkylamino radicals, C2- to C20-alkenyl radicals or C6- to C20-aryl, -aryloxy, -arylcarboxy or -arylamino radicals which optionally are substituted, q is an integer from 2 to 6 and r is an integer, wherein the alkylamino radicals mentioned are optionally continued in the alkyl moiety;
- and
- (e) a polyvinylamine of formula (V)
- which has an average molecular weight (MW) ranging from 300 to 100,000,000 and wherein R12 to R16 are independently hydrogen, linear or branched C1- to C20-alkyl, -alkoxy, -(alkyl)carboxy, -phosphonoalkyl, -alkylamino radicals, C2- to C20-alkenyl radicals or C6- to C20-aryl, -aryloxy, -arylcarboxy or -arylamino radicals which optionally are substituted, and R15 is additionally a formamidyl radical, s is an integer and t is 0 or an integer.
17 more elements
Dependencies are inferred from the claim text.