Patent US3764174A successfully refreshed from Google Patents.
Patent US4263431A successfully refreshed from Google Patents.
US4263431A
Expired / Lapsed
US
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Cationic fluorescent whitening agents
Assignee: BASF Corp
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Filing: 1979-05-17
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Granted: 1981-04-21
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Expires: 1999-05-17
Abstract
Abstract The invention relates to cationic fluorescent whitening agents of the formula ##STR1## wherein A is the radical of a fluorescent whitening agent, Q is the direct bond or a bridge member, R 1 to R 5 are specific substituents and n is 1 or 2. A process for the manufacture of these compounds and a method of whitening organic material which comprises their use are also disclosed.
Inventors
- 👤 Kurt Weber
- 👤 Christian Luthi
- 👤 Hans R. Meyer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 23:46
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/06; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/14; C07D295/00; C07D295/22; C07D295/26; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/141; C07F9/142; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; D; D06; D06L; D06L4/00; D06L4/60; D06L4/614; D06L4/629
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
392 words
A cationic fluorescent whitening agent of the formula ##STR214## wherein A is a radical selected from the group consisting of 1,3-diarylpyrazolines, 4,4'-distyrylbiphenyls or naphthalimides, Q' is --SO 2 --alkyleneoxy containing 2 to 4 carbon atoms, --SO 2 -- alkylene--COO--containing 2 to 4 carbon atoms, --SO 2 , --COO--, --SO 2 --alkylene --CON(R 6 )--containing 2 to 4 carbon atoms in the alkylene moiety, --SO 2 N(R 6 )-- or --CON(R 6 )--, wherein R 6 is hydrogen, unsubstituted or substituted alkyl of 1 to 5 carbon atoms substituted by cyano, carbamoyl, carboxyl, carbalkoxy, hydroxyl, halogen or alkoxy of 1 to 4 carbon atoms, or together with R 1 ' forms a piperazine radical, bridging member alkylene is a bivalent straight or branched alkylene of 2 to 20 carbon atoms, R 1 ' is unsubstituted or substituted alkyl of 1 to 6 carbon atoms substituted by halogen, cyano, hydroxyl, alkoxycarbonyl of 1 to 4 carbon atoms or alkylcarbonyloxy of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, aralkyl or aralkyl substituted on the benzene ring by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, or together with R 6 forms a piperazine radical or together with R 2 forms a heterocyclic ring selected from the group consisting of piperidine, pyrrolidine or morpholine, or said heterocycles substituted by alkyl groups of 1 to 4 carbon atoms, R 2 is unsubstituted or substituted alkyl of 1 to 6 carbon atoms substituted by halogen, cyano, hydroxyl, alkoxycarbonyl of 1 to 4 carbon atoms or alkylcarbonyloxy of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, aralkyl or aralkyl substituted on the benzene ring by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, or together with R 1 ' forms a heterocyclic ring selected from the group consisting of piperidine, pyrrolidine or morpholine or said hetercycles substituted by alkyl group of 1 to 4 carbon atoms, R 3 is alkyl of 1 to 4 carbon atoms, R 4 is hydrogen, unsustituted or substituted alkyl of 1 to 4 carbon atoms substituted by hydroxyl, cyano, alkylcarbonyloxy or alkoxycarbonyl each containing 1 to 4 carbon atoms in the alkyl moiety, R 5 is alkyl of 1 to 4 carbon atoms, and n is 1 or 2.
Claim 2
Dependent Claim
392 words
A cationic fluorescent whitening agent of the formula ##STR214## wherein A is a radical selected from the group consisting of 1,3-diarylpyrazolines, 4,4'-distyrylbiphenyls or naphthalimides, Q' is --SO 2 --alkyleneoxy containing 2 to 4 carbon atoms, --SO 2 -- alkylene--COO--containing 2 to 4 carbon atoms, --SO 2 , --COO--, --SO 2 --alkylene --CON(R 6 )--containing 2 to 4 carbon atoms in the alkylene moiety, --SO 2 N(R 6 )-- or --CON(R 6 )--, wherein R 6 is hydrogen, unsubstituted or substituted alkyl of 1 to 5 carbon atoms substituted by cyano, carbamoyl, carboxyl, carbalkoxy, hydroxyl, halogen or alkoxy of 1 to 4 carbon atoms, or together with R 1 ' forms a piperazine radical, bridging member alkylene is a bivalent straight or branched alkylene of 2 to 20 carbon atoms, R 1 ' is unsubstituted or substituted alkyl of 1 to 6 carbon atoms substituted by halogen, cyano, hydroxyl, alkoxycarbonyl of 1 to 4 carbon atoms or alkylcarbonyloxy of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, aralkyl or aralkyl substituted on the benzene ring by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, or together with R 6 forms a piperazine radical or together with R 2 forms a heterocyclic ring selected from the group consisting of piperidine, pyrrolidine or morpholine, or said heterocycles substituted by alkyl groups of 1 to 4 carbon atoms, R 2 is unsubstituted or substituted alkyl of 1 to 6 carbon atoms substituted by halogen, cyano, hydroxyl, alkoxycarbonyl of 1 to 4 carbon atoms or alkylcarbonyloxy of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, aralkyl or aralkyl substituted on the benzene ring by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, or together with R 1 ' forms a heterocyclic ring selected from the group consisting of piperidine, pyrrolidine or morpholine or said hetercycles substituted by alkyl group of 1 to 4 carbon atoms, R 3 is alkyl of 1 to 4 carbon atoms, R 4 is hydrogen, unsustituted or substituted alkyl of 1 to 4 carbon atoms substituted by hydroxyl, cyano, alkylcarbonyloxy or alkoxycarbonyl each containing 1 to 4 carbon atoms in the alkyl moiety, R 5 is alkyl of 1 to 4 carbon atoms, and n is 1 or 2.
Claim 3
Dependent Claim
62 words
A cationic fluorescent whitening agent according to claim 1 of the formula ##STR215## wherein Q', R 1 ', R 2 to R 5 and n are as defined in claim 1 and A' is a radical of the formula ##STR216## or of the formula ##STR217## the benzene rings of which formulae can also be substituted at the indicated positions by non-chromophoric substituents.
Claim 4
Dependent Claim
164 words
A cationic fluorescent whitening agent according to claim 2 of the formula ##STR218## wherein R 4 and R 5 are as defined in claim 3 and m is 0 or 1, R 7 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R 8 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, R 9 is hydrogen or alkyl of 1 to 4 carbon atoms, R 10 , R 11 and R 12 , if m is 1, have the meanings of R 7 , R 8 and R 9 or, if m is 0, each of R 10 , R 11 and R 12 independently is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen, and X is the radical ##STR219## wherein Q', R 1 ', R 2 and R 3 are as defined in claim 3.
Claim 5
Dependent Claim
199 words
A cationic fluorescent whitening agent according to claim 3 of the formula ##STR220## wherein Q" is --COO--, --CON(R 6 )-- or --SO 2 N(R 6 )--, R 1 ' is unsubstituted or substituted alkyl, alkenyl or aralkyl, together with R 6 is a piperazine radical or together with R 2 ' is a pyrrolidine, piperidine or morpholine radical, R 2 ' is unsubstituted or substituted alkyl, alkenyl or aralkyl or together with R 1 ' is a pyrrolidine, piperidine or morpholine radical, R 3 is alkyl of 1 to 4 carbon atoms, R 4 is hydrogen or unsubstituted or substituted alkyl, R 5 is alkyl of 1 to 4 carbon atoms, R 6 is hydrogen, unsubstituted or substituted alkyl of 1 to 5 carbon atoms or together with R 1 ' is a piperazine radical, R 7 ' is hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, R 8 ' is hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, R 9 is hydrogen or alkyl of 1 to 4 carbon atoms, and Z is alkylene of 2 to 5 carbon atoms.
Claim 6
Dependent Claim
203 words
A cationic fluorescent whitening agent according to claim 2 of the formula ##STR221## wherein R 1 ' is unsubstituted or substituted alkyl, alkenyl or aralkyl, together with R 6 is a piperazine ring or together with R 2 ' is a pyrrolidine, piperidine or morpholine radical, R 2 ' is unsubstituted or substituted alkyl, alkenyl or aralkyl or together with R 1 ' is a pyrrolidine, piperidine or morpholine radical, R 3 is alkyl of 1 to 4 carbon atoms, R 4 is hydrogen or unsubstituted or substituted alkyl, R 5 is alkyl of 1 to 4 carbon atoms, R 13 , R 14 and R 15 each independently of the other, is hydrogen, chlorine, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, Y is alkylene of 2 or 3 carbon atoms, --N(R 6 )-- alkylene containing 2 to 5 carbon atoms in the alkylene moiety, alkyleneoxyalkylene containing altogether 4 to 8 carbon atoms, alkylene--COO--alkylene or alkylene--CON(R 6 )--alkylene, each containing altogether 4 to 8 carbon atoms in the alkylene moiety, and R 6 is hydrogen, unsubstituted or substituted alkyl of 1 to 5 carbon atoms or together with R 1 ' is a piperazine radical.
Claim 7
Dependent Claim
107 words
A cationic fluorescent whitening agent according to claim 4 of the formula ##STR222## wherein R 3 to R 5 , R 7 ', R 8 ', R 9 and Z are as defined in claim 5, Q" is --COO--, --CON(R 6 )-- or --SO 2 N(R 6 )--, wherein R 6 is hydrogen, unsubstituted or substituted alkyl of 1 to 5 carbon atoms or together with R 1 " is a piperazine radical, R 1 " is unsubstituted alkyl of 1 to 4 carbon atoms or together with R 6 is a piperazine radical, and R 2 " is unsubstituted alkyl of 1 to 4 carbon atoms.
Claim 8
Dependent Claim
190 words
A cationic fluorescent whitening agent according to claim 5 of the formula ##STR223## wherein R 3 , R 4 and R 5 are as defined in claim 6, R 1 ''' is unsubstituted or substituted alkyl of 1 to 4 carbon atoms, together with R 6 is a piperazine radical or together with R 2 ''' is a pyrrolidine, piperidine or morpholine radical, R 2 ''' is unsubstituted or substituted alkyl of 1 to 4 carbon atoms or together with R 1 ''' is a pyrrolidine, piperidine or morpholine radical, R 13 ' represents hydrogen or alkyl of 1 to 4 carbon atoms, R 14 ' represents hydrogen or chlorine, Y' represents alkylene of 2 or 3 carbon atoms, --N(R 6 )-- alkylene containing 2 to 5 carbon atoms in the alkylene moiety, alkyleneoxyalkylene or alkylene--COO-- alkylene, each containing altogether 4 to 6 carbon atoms in the alkylene moiety, or alkylene--CON(R 6 )-- alkylene containing altogether 4 to 8 carbon atoms in each alkylene moiety, and R 6 represents hydrogen, unsubstituted or substituted alkyl of 1 to 5 carbon atoms or together with R 1 ''' represents a piperazine radical.
Claim 9
Dependent Claim
13 words
A cationic fluorescent whitening agent according to claim 6 of the formula ##STR224##
Claim 10
Dependent Claim
13 words
A cationic fluorescent whitening agent according to claim 6 of the formula ##STR225##
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-04-20 | 1984-10-20 | 1985-04-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-04-20 | 1988-10-20 | 1989-04-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-04-20 | 1992-10-20 | 1993-04-21 | $7700.00 | Window Closed / Lapsed |