| PATENT ASSIGNEE'S COUNTRY | UK |
| UPDATE | 10.99 |
| PATENT NUMBER | This data is not available for free |
| PATENT GRANT DATE | 12.10.99 |
| PATENT TITLE |
Dyestuff salts containing a cationic group derived from a sterically hindered amine |
| PATENT ABSTRACT |
A salt of formula I F.sub.n.A (I) in which F is the residue of a metal free anionic dyestuff having 1 to 4 acids groups, n is 1 to 2; and A is a group containing 1 to 4 sterically hindered amine groups and at least n ammonium or immonium groups. |
| PATENT INVENTORS | This data is not available for free |
| PATENT ASSIGNEE | This data is not available for free |
| PATENT FILE DATE | 25.04.97 |
| PATENT FOREIGN APPLICATION PRIORITY DATA | This data is not available for free |
| PATENT REFERENCES CITED | Ferruti et al., J. Am. Chem. Soc. 92, 3704-3713 (1970). |
| PATENT PARENT CASE TEXT | This data is not available for free |
| PATENT CLAIMS |
We claim: 1. A compound of the formula I: F.sub.n.A (I) wherein F is a residue of a metal-free anionic dyestuff having 1-4 acid groups; n is 1 to 2; A is ##STR17## R.sub.4 is a group of formula (b) ##STR18## R.sub.5 is a group of formula (c) ##STR19## wherein Y is .dbd.*N--CO--; R.sub.5' is a group of formula (c) wherein Y is --*CO--N.dbd.; the *atom is attached to the piperidyl group; R.sub.6 is a group of formula (d) ##STR20## R.sub.7 is a group of formula (e) ##STR21## R.sub.11 is H or C.sub.1-4 alkyl; R.sub.12 is each independently C.sub.1-6 alkyl; and R.sub.13 is each independently H, methyl, or ethyl; or one is phenyl and the other is H, methyl, or ethyl; or both together form a group --(CH.sub.2).sub.5-11 --. 2. A compound of claim 1 wherein R.sub.11 is H or methyl. 3. A compound of claim 2 wherein R.sub.11 is H. 4. A compound of claim 1 wherein R.sub.12 is methyl. 5. A process of coloring a substrate which comprises applying to said substrate a compound of claim 1. -------------------------------------------------------------------------------- |
| PATENT DESCRIPTION |
The invention relates to new organic compounds which are practically water-insoluble salts of acid dyestuffs with basic compounds which have at least one sterically hindered amine group. These compounds are excellent as pigments, particularly for the dyeing of solvent-free and solvent-containing plastics materials. According to the invention there is provided a salt of formula I F.sub.n.A (I) in which F is the residue of a metal-free anionic dyestuff having m acid groups, n is 1 or 2; m is 1 to 4; and A is group containing 1 to 4 sterically hindered amine groups, whereby from 1 to n.times.m ammonium and/or immonium groups are present in a salt of formula I. Preferably the acid groups are selected from sulpho and carboxy. Where the number of ammonium and immonium groups in A is fewer than the number of acid groups in F.sub.n, any excess acid groups are in free acid form. All other acid groups are in salt form. In this specification a sterically hindered amine group is preferably one containing a 2,2,6,6-tetralkylpiperidinyl group, preferably wherein each alkyl is C.sub.1-4 alkyl, more preferably methyl. The pigments according to the invention are excellent for coloring PVC, all types of polyolefin (HDPE or LDPE (high density polyethylene or low density polyethylene) or polypropylene) polyisobutylene, poly-4-methylpentene and copolymers of these. Further, the compounds according to the invention can be used for coloring polystyrene (and copolymers thereof), ABS, Polyvinylacetate, Polyvinylalcohol, Polyacetates, Polyether (POM), Polyacrylates, Polyacrylonitrile, Polyacrylamide, Polyvinylidenechloride, Polyesters, Polyethers, Polythioethers and Thioplasts, Polycarbonates, Polyurethanes, Cellulose derivatives, Maleic acid, Melamine, Phenol, Aniline, Furane, Carbamide, Epoxide and Silicone resins. The compounds of formula I can also be used in lacquers and printing inks for the graphics industry. Preferably F is F', where F' is a group derived from an acid group-containing non-metallised dyestuff of the azo series, of the phthalocyanine series, of the anthraquinone series, of the perylene series, of the indigo series, of the thioindigo series, of the pyrazolone series, of the perinone series, of the quinacridone series, of the dioxazine series, of the isoindoline series, of the isoindolinone series, of the diketopyrrole series or of the pyrrole series, especially of the azo, the phthalocyanine, the indigo, the anthraquinone, the dioxazine and the isoindoline series. Preferably F' is Fa, where Fa is a group derived from an acid-containing non-metallized dyestuff of the azo, anthraquinone or pyrazolone series. More preferably, Fa is Fb where Fb is selected from a group derived from compounds of formula II, III or IV: ##STR1## wherein each R.sub.20 independently is halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and hydrogen and R.sub.21 is hydrogen, sulpho, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen, --C(halogen).sub.3 or ##STR2## R.sub.22 is carboxy or ##STR3## wherein R.sub.23 is sulpho, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or hydrogen; with the proviso that R.sub.22 is carboxy or contains a sulfo group when R.sub.19 does not contain a sulpho group; ##STR4## in which R.sub.30 is carboxy or C.sub.1-4 alkyl; R.sub.24 is phenyl, unsubstituted or monosubstituted by sulpho with the proviso that when neither R.sub.19 nor R.sub.24 contains a sulpho group, R.sub.30 is carboxy; ##STR5## wherein R.sub.25 is sulpho, hydrogen or halogen; with the proviso that when the compound contains one R.sub.25 group and R.sub.25 is other than sulpho, at least one R.sub.28 is carboxy or sulpho, and when the compound contains two R.sub.25 groups, at least one of them is sulpho; R.sub.27 is hydrogen or cyclohexyl ##STR6## wherein each R.sub.28 independently is selected from carboxy, C.sub.1-4 alkyl, sulpho, C.sub.1-4 alkoxy, halogen, hydrogen and --NHCO--C.sub.6 H.sub.5 ; and R.sub.40 is hydrogen, methyl, --CH.sub.2 NHCOC(Cl).dbd.CH.sub.2 or --NH--CO--C.sub.1-4 alkyl; and R.sub.41 is hydrogen or halogen. more specifically F is preferably F", where F" is a compound of formula F.sub.1 to F.sub.43 : ##STR7## in which each R.sub.9 independently is Chloro, Bromo, C.sub.1-3 alkyl or C.sub.1-4 alkoxy and p=1,2 or 3, ##STR8## Preferably any sterically hindered amine group present is selected from formulae (a) to (e) below: ##STR9## in which R.sub.11 is hydrogen or C.sub.4 alkyl, preferably hydrogen or methyl, more preferably hydrogen; each R.sub.12 independently is C.sub.1-6 alkyl, preferably methyl; both groups R.sub.13 independently are hydrogen, methyl or ethyl or one group R.sub.13 is phenyl and the other R.sub.13 is hydrogen, methyl or ethyl or both groups R.sub.13 together form a group of --(CH.sub.2)--.sub.5-11 and Y is a group of the formula ##STR10## Preferably A is A' where A' is a cationic group derived from a compound selected from A1-A29 A.sub.1 1,3,5-Tri-(1',2',2',6',6'-pentamethylpiperidyl-4'-)trimesinic acid triamide, A.sub.2 2,4-Bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-6-chlorotriazine, A.sub.3 2,4,6-Tri-(2',2',6',6'-tetramethylpiperidyl-4'-amino)triazine, A.sub.4 Bis-(2',2',6',6'-tetramethylpiperidyl-4'-aminocarbonyl-paraphenylene)-tere phthalic acid diamide, a compound of the formula ##STR11## A.sub.5 Bis-(2',2',6',6'-tetramethylpiperidyl-4'-)terephthalic acid amide, A.sub.6 2,4-Bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)quinazoline, A.sub.7 2,3-Bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)quinoxaline, A.sub.8 1,4-Bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)phthalazine, A.sub.9 2-Chloro-4,6-bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)pyrimidine, A.sub.10 2,5-Dichloro-4,6-bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)pyrimidine A.sub.11 2-Fluoro-5-chloro-4,6-bis-(2',2',6',6'-tetramethylpiperidyl-4'-amino)pyrim idine, A.sub.12 2,4,6-Tri-(2',2',6',6'-tetramethylpiperidyl-4'-amino)pyrimidine, A.sub.13 2,4,6-Tri-(2',2',6',6'-tetramethylpiperidyl-4'-amino)-5-chloropyrimidine, ##STR12## A.sub.23 Bis-(1,2,2,6,6-pentamethylpiperidyl-4)-terephthalic acid amide, A.sub.24 Bis-(1,2,2,6,6-pentamethylpiperidyl-4)-isophthalic acid amide, ##STR13## in which R.sub.3 is 2,2,6,6-tetramethylpiperidyl-4-; R.sub.4 is a group of formula b) defined above; R.sub.5 is a group of formula c) as defined above, wherein Y is ##STR14## R.sub.5 is a group of formula c) as defined above, wherein Y is ##STR15## where the * atom is attached to the piperidyl group; R.sub.6 is a group formula d) defined above, and R.sub.7 is a group of formula e) defined above; the other symbols appearing in said formulae being as defined above. The production of the compounds of formula A1 to A29 can be carried out by known methods, preferably through condensation of the corresponding amine with the corresponding carboxylic acid (or carboxylic acid chloride) or, for example, the condensation of the corresponding amine with trichlorotriazine, dichloroquinazoline, dichloroquinoxaline, dichlorophthalazine, tri- or tetrachloropyrimidine. Corresponding compounds containing the groups of formulae a) to e) are known. The production of the new pigments can be carried out by salting the appropriate dyestuff with a basic compound A by known methods. For example, acid dyestuffs as obtained after production, i.e. in the form of sodium salts, can be reacted in the presence of an adequate amount of mineral acid (for example HCl) with the basic components A to form the salt. The compounds of formula I are very strong in color, either when they are used in small amounts or when they are used in the usual amounts for other organic pigments. Normal amounts used are from 0.02 to 5%, more preferably 0.06 to 3%, by weight of the substrate to be pigmented. The colorings using the compounds of formula I show excellent light fastness. Furthermore the substrates to which the compounds of formula I have been applied show excellent stability against the detrimental effects of UV light, heat and oxidation. The following examples illustrate the invention, in which all parts and percentages are by weight and all temperatures given are in .degree. C. |
| PATENT EXAMPLES | This data is not available for free |
| PATENT PHOTOCOPY | Available on request |
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