Claims
- 1. A 4-styryl-4'vinylbiphenyl of the formula ##STR91## wherein each of R.sub.1 and R.sub.2 is hydrogen or a non-chromophoric substituent, or both together when ortho to each other complete a fused ring, R.sub.3 is a second order non-chromophoric substituent and R.sub.4 is hydrogen or alkyl or alkenyl, each unsubstituted or substituted by a non-chromophoric group.
- 2. A 4-styryl-4'-vinylbiphenyl of claim 1 wherein R.sub.1 is hydrogen or halogen; alkyl, alkoxy or alkylsulfonyl, each unsubstituted or substituted by a non-chromophoric group; phenyl, phenylalkyl or phenylsulfonyl, phenoxy or phenylalkoxy, each unsubstituted or substituted by a non-chromophoric group; or is cyano, a group of the formula --COOY.sub.1 --, --CONY.sub.1 Y.sub.2 or --SO.sub.2 NY.sub.1 Y.sub.2, wherein each of Y.sub.1 and Y.sub.2 independently is hydrogen, alkenyl, propargyl, cycloalkyl containing 5 or 6 ring carbon atoms, or is alkyl, phenyl or phenylalkyl, each unsubstituted or substituted by a non-chromophoric group; or Y.sub.1 and Y.sub.2, together with the nitrogen atom to which they are attached, are a 5- or 6-membered saturated heterocyclic ring which can additionally contain 1 or 2 hetero-atoms as ring members and can also be substituted by an alkyl group; or wherein Y.sub.1 is the group --COOY.sub.1 can also additionally be a salt-forming cation; or R.sub.1 is a group of the formula ##STR92## wherein each of X.sub.1 and Y independently of the other is halogen, alkyl, alkenyl, phenyl, phenylalkyl, hydroxy, alkoxy, phenylalkoxy, cycloalkoxy, phenoxy, amino, mono- or dialkylamino, phenyalkylamino, acylamino, phenylamino, cycloalkylamino, morpholino, piperidino or pyrrolidino; R.sub.2 is hydrogen, halogen, or alkyl or alkoxy, each unsubstituted or substituted by a non-chromophoric group; or R.sub.1 together with R.sub.2 when ortho to each other are --CH.dbd.CH--CH.dbd.CH--, --O--CH.sub.2 --O-- or --O--CH.sub.2 --CH.sub.2 --O--; R.sub.3 is alkylsulfonyl, phenylsulfonyl, alkoxysulfonyl; cyano, trifluoromethyl, sulfo, a group of the formula --COOY.sub.1, --CONY.sub.1 Y.sub.2 or --SO.sub.2 NY.sub.1 Y.sub.2, wherein Y.sub.1 and Y.sub.2 are as defined above; or is a group of the formula ##STR93## wherein X.sub.1 and Y are as defined above; and R.sub.4 is hydrogen or alkyl which is unsubstituted or substituted by a non-chromophoric group.
- 3. A 4-styryl-4'-vinylbiphenyl of claim 2 wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfonyl, cyano, or phenyl or phenylsulfonyl, each unsubstituted or substituted by one or more of chlorine, methyl and methoxy; or is a group of the formula --COOY.sub.1, --CONY.sub.1 Y.sub.2 or --SO.sub.2 NY.sub.1 Y.sub.2, wherein Y.sub.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.4 alkenyl, cyclohexyl, C.sub.2 -C.sub.4 hydroxyalkyl, C.sub.3 -C.sub.6 alkoxyalkyl, a radical of the formula --CH.sub.2 CH.sub.2 O).sub.n (C.sub.1 -C.sub.4 alkyl), wherein n is an integer from 1 to 6, or is C.sub.6 -C.sub.9 phenoxyalkyl, C.sub.2 -C.sub.6 carboxyalkyl, C.sub.3 -C.sub.6 carbalkoxyalkyl, C.sub.2 -C.sub.5 cyanoalkyl, phenyl or benzyl, each unsubstituted or substituted by one or more of chlorine, methyl and methoxy, or is C.sub.3 -C.sub.7 dialkylaminoalkyl or phenethyl; Y.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 hydroxyalkyl, or Y.sub.1 and Y.sub.2, together with the nitrogen atom to which they are attached, are a 5- or 6-membered saturated heterocyclic ring which can additionally contain a further nitrogen or oxygen atom as ring member and which can be substituted by 1 or 2 C.sub.1 -C.sub.4 alkyl groups; or wherein Y.sub.1 in the group --COOY.sub.1 can additionally be an alkali metal ion or an ammonium ion; or R.sub.1 is a group of the formula ##STR94## wherein each of X.sub.1 and Y independently of the other is C.sub.1 -C.sub.4 alkyl, benzyl, phenyl which is unsubstituted or substituted by one or more of chlorine, methyl and methoxy; R.sub.2 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl; R.sub.3 is cyano, C.sub.1 -C.sub.4 alkylsulfonyl or a group of the formula --COOY.sub.1, --CONY.sub.1 Y.sub.2, SO.sub.2 NY.sub.1 Y.sub.2 or ##STR95## wherein Y.sub.1, Y.sub.2, X.sub.1 and Y are as defined above; and R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl.
- 4. A 4-styryl-4'-vinylbiphenyl of claim 3 wherein R.sub.1 is halogen, C.sub.1 -C.sub.4 alkylsulfonyl, cyano or a group of the formula --COOY.sub.1, wherein Y.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 hydroxyalkyl, C.sub.3 -C.sub.6 alkoxyalkyl, a radical of the formula --CH.sub.2 CH.sub.2 --O).sub.n (C.sub.1 -C.sub.4 -alkyl), wherein n is an integer from 1 to 4, or is C.sub.2 -C.sub.6 carboxyalkyl, C.sub.3 -C.sub.6 carbalkoxyalkyl or C.sub.2 -C.sub.5 cyanoalkyl; or is a group of the formula ##STR96## R.sub.2 is hydrogen or halogen; R.sub.3 is C.sub.1 -C.sub.4 alkylsulfonyl, cyano, a group of the formula ##STR97## or a group of the formula --COOY.sub.1, wherein Y.sub.1 is as defined above, and R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl.
- 5. A 4-styryl-4'-vinylbiphenyl of claim 4 wherein R.sub.1 is C.sub.1 -C.sub.4 alkoxysulfonyl, cyano, ##STR98## or --COOY.sub.1, wherein Y.sub.1, is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 hydroxyalkyl, C.sub.3 -C.sub.6 alkoxyalkyl, (CH.sub.2 --CH.sub.2 --O).sub.n (C.sub.1 -C.sub.4 alkyl), wherein n is an integer from 1 to 4, or is C.sub.3 -C.sub.6 carbalkoxyalkyl, C.sub.2 -C.sub.6 carboxyalkyl or C.sub.2 -C.sub.5 cyanoalkyl; R.sub.2 is hydrogen or halogen; R.sub.3 is C.sub.1 -C.sub.4 alkylsulfonyl, cyano, ##STR99## or --COOY.sub.1, wherein Y.sub.1 is as defined above; and R.sub.4 is hydrogen.
- 6. A 4-styryl-4'-vinylbiphenyl of claim 5, wherein R.sub.1 is cyano or --COOY.sub.1, wherein Y.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 hydroxyalkyl, C.sub.3 -C.sub.6 alkoxyalkyl or --CH.sub.2 --CH.sub.2 --O).sub.n (C.sub.1 -C.sub.4 alkyl), wherein n is an integer from 1 to 4, R.sub.3 is cyano or --COOY.sub.1, wherein Y.sub.1 is as defined above, and R.sub.2 is hydrogen or chlorine.
- 7. A 4-styryl-4'-vinylbiphenyl of claim 5, wherein R.sub.1 is cyano, R.sub.2 is hydrogen, and R.sub.3 is cyano or --COOY.sub.1, in which Y.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 hydroxyalkyl, C.sub.3 -C.sub.6 alkoxyalkyl or --CH.sub.2 --CH.sub.2 --O).sub.n (C.sub.1 -C.sub.4 alkyl), wherein n is an integer from 1 to 4.
- 8. The 4-styryl-4'-vinylbiphenyl of claim 7 of the formula ##STR100##
- 9. A process for the production of a 4-styryl-4'-vinylbiphenyl of claim 1, which process comprises reacting a biphenyl-4,4'-dialdehyde of the formula ##STR101## with a compound of the formula ##STR102## to give an aldehyde of the formula ##STR103## and subsequently reacting this aldehyde with a compound of the formula ##STR104## to give a compound of claim 1, in which formulae above R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in claim 1, and X and Z.sub.1 are the same or different and each independently of the other is hydrogen, a radical of the formula --COOZ, wherein Z is hydrogen or alkyl, ##STR105## wherein A.sup..crclbar. is a monovalent colorless anion.
- 10. A process according to claim 9, wherein each of X and Z.sub.1 independently of the other is a group of the formula ##STR106##
- 11. A process for the production of a 4-styryl-4'-vinylbiphenyl of claim 1, which process comprises reacting a biphenyl-4,4'-dialdehyde of the formula ##STR107## with a compound of the formula ##STR108## to give an aldehyde of the formula ##STR109## and subsequently reacting this aldehyde with a compound of the formula ##STR110## to give a compound of claim 1, in which formulae above R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in claim 1, and X and Z.sub.1 are the same or different and each independently of the other is hydrogen or a radical of the formula --COOZ, wherein Z is hydrogen or alkyl, ##STR111## wherein A.sup..crclbar. is a monovalent colorless anion.
- 12. A process of any of claims 9 to 11, wherein the reaction of the biphenyl-4,4'-dialdehyde with a compound of the formula ##STR112## is carried out in a solvent in which the resultant monoaldehyde is sparingly soluble and from which it crystallizes out.
- 13. A process of any one of claims 9 to 11, wherein the reaction of the biphenyl-4,4'-dialdehyde with a compound of the formula ##STR113## is carried out in the presence of an alkali condensing agent, in the temperature range of 0.degree. to 50.degree. C.
- 14. A process of any one of claims 9 to 11, wherein the monoaldehyde obtained in the first step is further reacted without being isolated.
- 15. A process of any one of claims 9 to 11, wherein the monoaldehyde obtained in the first step is isolated and then without purification further reacted in a solvent in which the monoaldehyde is soluble.
- 16. A process of claim 15, wherein the reaction of the monoaldehyde obtained in the first step with a compound of the formula ##STR114## is carried out in the presence of an alkali metal alcoholate, in the temperature range of 20.degree. to 100.degree. C.
- 17. A composition for whitening organic material of high molecular weight which contains one or more compounds of claim 1, with conventional formulation additives.
- 18. A composition according to claim 17 which contains an additional fluorescent whitening agent which gives a greenish to bluish hue on the reacted substrate.
- 19. A composition according to claim 18 wherein the additional fluorescent whitening agent is selected from the group consisting of the bis-styrylbenzenes, benzoxazolylstilbenes, 4,4'-divinylstilbenes, naphthalimides, 4,4'-bis-styrylbiphenyls, 4,4'-bis-triazolylstilbenes, bis-benzoxazolylthiophenes, naphthotriazolylstilbenes and coumarines.
- 20. A composition according to claim 19 wherein the fluorescent whitener consists of 10 to 90%, of the first fluorescent whitening agent, and 90 to 1% of the additional fluorescent whitening agent.
- 21. A process for whitening a natural, regenerated or synthetic organic substrate of high molecular weight, which process comprises incorporating in or applying to said substrate a compound of claim 1.
- 22. A process according to claim 21 for whitening a polyester substrate.
- 23. A process according to either of claims 21 or 22 which comprises incorporating in or applying to the substrate to be whitened 0.001 to 2%, of fluorescent whitening agent or of a mixture of fluorescent whitening agent, based on the weight of said substrate.
- 24. Organic material of high molecular weight, containing 0.001 to 2%, of a fluorescent whitening agent of claim 1.
Priority Claims (1)
Number |
Date |
Country |
Kind |
9192/80 |
Dec 1980 |
CHX |
|
Parent Case Info
This application is a continuation of application Ser. No. 327,665, filed 12/7/81 abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3984399 |
Weber et al. |
Oct 1976 |
|
4118560 |
Weber |
Oct 1978 |
|
4147648 |
Gunter et al. |
Apr 1979 |
|
Continuations (1)
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Number |
Date |
Country |
Parent |
327665 |
Dec 1981 |
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