Triazinylaminostilbene disulphonic acid mixtures
AssigneeCiba Specialty Chemicals Corporation
InventorsFabienne Cuesta, Ted Deisenroth, Peter Rohringer
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Abstract
The present invention relates to a fluorescent whitening agent comprising a mixture of two symmetrically and one asymmetrically substituted triazinylaminostilbene disulphonic acids, certain novel derivatives, a process for their preparations and use of the mixture for whitening synthetic or natural organic materials, especially paper and for the fluorescent whitening and improvement of sun protection factors of textile materials.
Claims16
A fluorescent whitening agent, which comprises a mixture of compounds of the formulae
- in which
- R1 and R2 are different and are not derived from the same amino acid or amino acid amide residue
- R1 is —NH2, —NHC1-C4alkyl, —N(C1-C4alkyl)2, —NHC2-C4hydroxyalkyl, —N(C2-C4hydroxyalkyl)2, —N(C1-C4alkyl)(C2-C4 hydroxyalkyl), a morpholino residue or an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- R2 is an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- each of the rings designated as A represent a 5- or 6-membered saturated heterocycle, which may contain one further heteroatom and M represents hydrogen, an alkali metal atom, ammonium or a cation formed from an amine.
A compound of the formula
- in which
- R1and R2 are different and are not derived from the same amino acid or amino acid amide residue
- R1 is —NH2, —NHC1-C4alkyl, —N(C1-C4alkyl)2, —NHC C2-C4 hydroxyalkyl, —N(C2-C4hydroxyalkyl)2, —N(C1-C4alkyl)(C2-C4 hydroxyalkyl), a morpholino residue or an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- R2 is an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- each of the rings designated as A represent a 5- or 6-membered saturated heterocycle, which may contain one further heteroatom and M reeresents hydrogen, an alkali metal atom, ammenium or a cation formed from an amine.
A compound of formula
- in which
- R2 is an amino acid or amino acid derivative from which a hydrogen atom has been removed from the amino group, whereby the residue is derived from alanine, sarcosine, serine, cysteine, phenylalanine, tyrosine (4-hydroxyphenylalanine), diiodotyrosine, tryptophan (β-indolylalanine), histidine (β-imidazolylalanine), α-aminobutyric acid, methionine, valine (α-aminoisovaleric acid), norvaline, leucine (α-aminoisocaproic acid), isoleucine (α-amino-β-methylvaleric acid), norleucine (α-amino-n-caproic acid), arginine, ornithine (α,δ-diaminovaleric acid), lysine (α,ε-diaminocaproic acid), aspartic acid (aminosuccinic acid), glutamic acid (α-aminoglutaric acid), threonine iminodiacetic acid, N-(propionamido)-N-(2-hydroxethyl)amine or corresponding propionic acid, hydroxyglutamic acid, and mixtures and optical isomers thereof,
- each of the rings designated as A represent a 5- or 6-membered saturated heterocycle, which may contain one further heteroatom and M represents hydrogen, an alkali metal atom, ammonium or a cation formed from an amine.
A method for whitening synthetic or natural organic material by treating the synthetic or natural material with a composition, which contains water, a fluorescent whitening agent, which comprises a mixture of the compounds (1a), (1b) and (1c), a compound of formula (1b) or a compound of formula (1c)
- in which
- R1 and R2 are different and are not derived from the same amino acid or amino acid amide residue
- R1 is —NH2, —NHC1-C4alkyl, —N(C1-C4alkyl)2, —NHC2-C4 hydroxyalkyl, —N(C2-C4hydroxyalkyl)2, —N(C1-C4alkyl)(C2-C4 hydroxyalkyl), a morpholino residue or an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- R2 is an amino acid or amino acid derivative from which a hydrogen atom has been removed from the amino group, whereby the residue is derived from alanine, sarcosine, serine, cysteine, phenylalanine, tyrosine (4-hydroxyphenylalanine), diiodotyrosine, tryptophan (β-indolylalanine), histidine (β-imidazolylalanine), α-aminobutyric acid, methionine, valine (α-aminoisovaleric acid), norvaline, leucine (α-aminoisocaproic acid), isoleucine α-amino-β-methylvaleric acid), norleucine (α-amino-n-caproic acid), arginine, ornithine (α,δ-diaminovaleric acid), lysine (α,ε-diaminocaproic acid), aspartic acid (aminosuccinic acid), glutamic acid α-aminoglutaric acid), threonine or hydroxyglutamic acid, as well as mixtures and optical isomers thereof, or from iminodiacetic acid or from N-(propionamido)-N-(2-hydroxyethyl)amine or the corresponding propionic acid,
- each of the rings designated as A represent a 5- or 6-membered saturated heterocycle, which may contain one further heteroatom and M represents hydrogen, an alkali metal atom, ammonium or a cation formed from an amine
- and, optionally, auxiliaries.
Paper, which has been optically brightened by the compound mixture of formulae (1a), (1b) and (1c), a compound of formula (1b) or a compound of formula(1c)
- in which
- R1 and R2 are different and are not derived from the same amino acid or amino acid amide residue
- R1 is —NH2, —NHC1-C4alkyl, —N(C1-C4alkyl)2, —NHC2-C4 hydroxyalkyl, —N(C2-C4hydroxyalkyl)2, —N(C1-C4alkyl)(C2-C4 hydroxyalkyl), a morpholino residue or an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- R2 is an amino acid or amino acid derivative from which a hydrogen atom has been removed from the amino group, whereby the residue is derived from alanine, sarcosine, serine, cysteine, phenylalanine, tyrosine (4-hydroxyphenylalanine), diiodotyrosine, tryptophan (β-indolylalanine), histidine (β-imidazolylalanine), α-aminobutyric acid, methionine, valine (α-aminoisovaleric acid), norvaline, leucine (α-aminoisocaproic acid), isoleucine α-amino-β-methylvaleric acid), norleucine α-amino-n-caproic acid), arginine, ornithine (α,δ-diaminovaleric acid), lysine (α,ε-diaminocaproic acid), aspartic acid (aminosuccinic acid), glutamic acid (α-aminoglutaric acid), threonine or hydroxyglutamic acid, as well as mixtures and optical isomers thereof, or from iminodiacetic acid or from N-(Propionamido)-N-(2-hydroxyethyl)amine or the corresponding propionic acid,
- each of the rings designated as A represent a 5- or 6-membered saturated heterocycle, which may contain one further heteroatom and M represents hydrogen, an alkali metal atom. ammonium or a cation formed from an amine.
A textile fabric produced from a fibre treated with the compound mixture of formulae (1a), (1b) and (1c), a compound of formula (1b) or a compound of formula (1c)
- in which R1 and R2 are different and are not derived from the same amino acid or amino acid amide residue
- R1 is —NH2, —NHC1-C4alkyl, —N(C1-C4alkyl)2, —NHC2-C4 hydroxyalkyl, —N(C2-C4hydroxyalkyl)2, —N(C1-C4alkyl)(C2-C4 hydroxyalkyl), a morpholino residue or an amino acid or an amino acid amide residue from which a hydrogen atom has been removed from the amino group,
- R2 is an amino acid or amino acid derivative from which a hydrogen atom has been removed from the amino group, whereby the residue is derived from alanine, sarcosine, serine, cysteine, phenylalanine, tyrosine (4-hydroxyphenylalanine), diiodotyrosine, tryptophan (β-indolylalanine), histidine (β-imidazolylalanine), α-aminobutyric acid, methionine, valine (α-aminoisovaleric acid), norvaline, leucine α-aminoisocaproic acid), isoleucine α-amino-β-methylvaleric acid), norleucine (α-amino-n-caproic acid), arginine, ornithine (α,δ-diaminovaleric acid), lysine (α,ε-diaminocaproic acid), aspartic acid (aminosuccinic acid), glutamic acid (α-aminoglutaric acid), threonine, iminodiacetic acid, N-(propionamido)-N-(2-hydroxethyl)amine or the corresponding proionic acid hydroxyglutamic acid, and mixtures and optical isomers thereof,
- each of the rings designated as A represent a 5- or 6-membered saturated heterocycle, which may contain one further heteroatom and M represents hydrogen, an alkali metal atom, ammonium or a cation formed from an amine.
Dependencies are inferred from the claim text.