US4314820A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Distyrylbenzene fluorescent brightening agents
Assignee: BASF Corp
•
Filing: 1980-04-02
•
Granted: 1982-02-09
•
Expires: 2000-04-02
Abstract
Abstract The distyrylbenzenes of the formula ##STR1## in which X and X' independently of one another are --COO-- or --CON(R 4 )-- in the o-position, a direct bond, oxygen, sulfur, --O--C 1-3 --alkylene--CON(R 4 )--, --SO 2 N(R 4 )--, --O--C 1-3 -alkylene--COO-- or --OCO--, Y and Y' independently of one another are C 1-20 -alkylene, R 1 and R 1 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or R 1 together with R 2 , or R 1 ' together with R 2 ', is a heterocyclic ring, R 2 and R 2 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or R 2 together with R 1 , or R 2 ' together with R 1 ', is a heterocyclic ring, or R 1 and R 2 , or R 1 ' and R 2 ', together with R 3 are a pyridine or picoline ring, R 3 is hydrogen, unsubstituted or substituted C 1-4 -alkyl or C 3-4 -alkenyl, or together with R 1 and R 2 or with R 1 ' and R 2 ' is a pyridine or picoline ring, R 4 is hydrogen or unsubstituted or substituted C 1-16 -alkyl, A.sup.⊖ is a colorless anion and n and n' independently of one another are the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents, can be prepared by reacting a correspondingly substituted benzaldehyde with a p-xylylenephosphonate and then alkylating or protonising the distyrylbenzenediamine formed. The distyrylbenzenes are fluorescent brightening agents for organic materials. They are particularly suitable for use as additives to textile and laundry after-treatment agents which contain cationic textile softeners.
Inventors
- 👤 Kurt Weber
- 👤 Hans R. Meyer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 06:17
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20; C07C; C07C309/00; C07D213/24; C07D213/28; C07D213/30; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C11; C11D; C11D3/00; C11D3/40; C11D3/42; D; D06; D06L; D06L4/00; D06L4/60; D06L4/614; D06L4/629
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
245 words
A distyrylbenzene of the formula ##STR107## in which X and X' independently of one another are --COO-- or --CON(R 4 -- in the o-position, a direct bond, oxygen, sulfur, --O--C 1-3 -alkylene--CON(R 4 )--, --SO 2 N(R 4 --, --O--C 1-3 -alkylene--COO-- or --OCO--, Y and Y' independently of one another are C 1-20 -alkylene, R 1 and R 1 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or R 1 together with R 2 , or R 1 ' together with R 2 ', is a heterocyclic ring, R 2 and R 2 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or R 2 together with R 1 , or R 2 ' together with R 1 ', is a heterocyclic ring, or R 1 and R 2 , or R 1 ' and R 2 ', together with R 3 are a pyridine or picoline ring, R 3 is hydrogen, unsubstituted or substituted C 1-4 -alkyl or C 3-4 -alkenyl, or together with R 1 and R 2 or with R 1 ' and R 2 ' is a pyridine or picoline ring, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n and n' independently of one another are the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents.
Claim 2
Dependent Claim
245 words
A distyrylbenzene of the formula ##STR107## in which X and X' independently of one another are --COO-- or --CON(R 4 -- in the o-position, a direct bond, oxygen, sulfur, --O--C 1-3 -alkylene--CON(R 4 )--, --SO 2 N(R 4 --, --O--C 1-3 -alkylene--COO-- or --OCO--, Y and Y' independently of one another are C 1-20 -alkylene, R 1 and R 1 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or R 1 together with R 2 , or R 1 ' together with R 2 ', is a heterocyclic ring, R 2 and R 2 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or R 2 together with R 1 , or R 2 ' together with R 1 ', is a heterocyclic ring, or R 1 and R 2 , or R 1 ' and R 2 ', together with R 3 are a pyridine or picoline ring, R 3 is hydrogen, unsubstituted or substituted C 1-4 -alkyl or C 3-4 -alkenyl, or together with R 1 and R 2 or with R 1 ' and R 2 ' is a pyridine or picoline ring, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n and n' independently of one another are the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents.
Claim 3
Dependent Claim
203 words
A distyrylbenzene according to claim 1, of the formula ##STR108## in which X 1 is --COO-- or --CONH-- in the o-position, a direct bond, oxygen, sulfur, --O--C 1-3 -alkylene--CONH--, --SO 2 NH--, --O--C 1-3 -alkylene--COO-- or --OCO--, Y 1 and Y 1 ' independently of one another are C 1-4 -alkylene or hydroxypropylene, R 1 " and R 2 " independently of one another are C 1-4 -alkyl or together are a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, or together with R 3 ' are a pyridine or picoline ring, R 3 ' is hydrogen, C 1-4 -alkyl, C 3-4 -alkenyl, C 1-3 -alkoxycarbonylmethyl, benzyl, C 2-4 -hydroxyalkyl or C 2-4 -cyanoalkyl, or together with R 1 " and R 2 " is a pyridine or picoline ring, R 5 is hydrogen, chlorine, C 1-4 -alkyl, C 3-4 -alkenyl or C 1-3 -alkoxy, or together with R 6 is a trimethylene or tetramethylene group, R 6 is hydrogen, chlorine, C 1-4 -alkyl or C 1-3 -alkoxy, or together with R 5 is a trimethylene or tetramethylene group, R 7 is hydrogen, chlorine or methyl, n and n' independently of one another are the number 0 or 1 and A.sup.⊖ is a colourless anion.
Claim 4
Dependent Claim
172 words
A distyrylbenzene according to claim 1, of the formula ##STR109## in which X 2 is --COO-- or --CONH-- in the o-position, oxygen, sulfur, --SO 2 N(R 4 )-- or --OCO--, Y 2 is C 1-20 -alkylene, R 1 is unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, together with R 2 is a heterocyclic ring or together with R 2 and R 3 is a pyridine or picoline ring, R 2 is unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, together with R 1 is a heterocyclic ring or together with R 1 and R 3 is a pyridine or picoline ring, R 3 is hydrogen, unsubstituted or substituted C 1-4 -alkyl or C 3-4 -alkenyl, or together with R 1 and R 2 is a pyridine or picoline ring, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, n is the number 0 or 1 and A.sup.⊖ is a colourless anion, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents.
Claim 5
Dependent Claim
189 words
A distyrylbenzene according to claim 2, of the formula ##STR110## in which X 1 is --COO-- or --CONH-- in the o-position or a direct bond, oxygen, sulfur, --O--C 1-3 -alkylene--CONH--, --SO 2 NH--, --O--C 1-3 -alkylene--COO-- or --OCO--, Y 1 is C 1-4 -alkylene or hydroxypropylene, R 1 " and R 2 " independently of one another are C 1-4 -alkyl, together are a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring or together with R 3 ' are a pyridine or picoline ring, R 3 ' is hydrogen, C 1-4 -alkyl, C 3-4 -alkenyl, C 1-3 -alkoxycarbonylmethyl, benzyl, C 2-4 -hydroxyalkyl or C 2-4 -cyanoalkyl, or together with R 1 " and R 2 " is a pyridine or picoline ring, R 5 is hydrogen, chlorine, C 1-4 -alkyl, C 3-4 -alkenyl or C 1-3 -alkoxy, or together with R 6 is a trimethylene or tetramethylene group, R 6 is hydrogen, chlorine, C 1-4 -alkyl or C 1-3 -alkoxy, or together with R 5 is a trimethylene or tetramethylene group, R 7 is hydrogen, chlorine or methyl, n is the number 0 or 1 and A.sup.⊖ is a colourless anion.
Claim 6
Dependent Claim
126 words
A distyrylbenzene according to claim 4, of the formula ##STR111## in which X 3 is a direct bond, oxygen, sulfur, --SO 2 NH or --OCO--, Y 3 is C 1-4 -alkylene, R 1 "' and R 2 "' independently of one another are C 1-4 -alkyl, together are a pyrrolidine, piperidine or morpholine ring, or together with R 3 ' are a pyridine ring, R 3 ' is hydrogen, C 1-4 -alkyl, C 3-4 -alkenyl, C 1-3 -alkoxycarbonylmethyl, benzyl, C 2-4 -hydroxyalkyl or C 2-4 -cyanoalkyl, or together with R 1 "' and R 2 "' is a pyridine ring, R 5 ' is hydrogen, chlorine, C 1-4 -alkyl or C 1-3 -alkoxy, n is the number 0 or 1 and A.sup.⊖ is a colourless anion.
Claim 7
Dependent Claim
82 words
A distyrylbenzene according to claim 4, of the formula ##STR112## in which Y 4 is C 2-4 -alkylene, R 1 IV is C 1-3 -alkyl or together with R 2 IV is a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 2 IV is C 1-3 -alkyl or together with R 1 IV is a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 3 " is hydrogen or C 1-3 -alkyl, n is the number 0 or 1 and A.sup.⊖ is a colourless anion.
Claim 8
Dependent Claim
125 words
A distyrylbenzene according to claim 3, of the formula ##STR113## in which X 4 is oxygen, sulfur, --OCO--, --COO-- or ##STR114## Y 5 is C 2-20 -alkylene, R 1 V is unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or together with R 2 V is a heterocyclic ring, R 2 V is unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or together with R 1 V is a heterocyclic ring, R 3 "' is hydrogen or unsubstituted or substituted C 1-4 -alkyl, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n is the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents.
Claim 9
Dependent Claim
116 words
A distyrylbenzene according to claim 7, of the formula ##STR115## in which Y 5 is C 2-20 -alkylene, R 1 V is unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or together with R 2 V is a heterocyclic ring, R 2 V is unsubstituted or substituted C 1-8 -alkyl or C 2-4 -alkenyl, or together with R 1 V is a heterocyclic ring, R 3 "' is hydrogen or unsubstituted or substituted C 1-4 -alkyl, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n is the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents.
Claim 10
Dependent Claim
116 words
A distyrylbenzene according to claim 7, of the formula ##STR116## in which Y 5 is C 2-20 -alkylene, R 1 V is unsubstituted or substituted C 1-8 -alkyl or C 3-4 -alkenyl, or together with R 2 V is a heterocyclic ring, R 2 V is unsubstituted or substituted C 1-8 -alkyl or C 2-4 -alkenyl, or together with R 1 V is a heterocyclic ring, R 3 "' is hydrogen or unsubstituted or substituted C 1-4 -alkyl, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n is the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents.
Claim 11
Dependent Claim
63 words
A distyrylbenzene according to claim 8, of the formula ##STR117## in which R 1 VI =R 2 VI and both are methyl or ethyl, R 3 IV is hydrogen, methyl or ethyl, A'.sup.⊖ is CH 3 OSO 3 .sup.⊖, C 2 H 5 OSO 3 .sup.⊖ or ##STR118## n is the number 0 or 1 and m is the number 2 or 3.
Claim 12
Dependent Claim
48 words
A distyrylbenzene according to claim 10, of the formula ##STR119## in which R 1 VI =R 2 VI and both are methyl or ethyl, R 3 V is hydrogen or methyl, A".sup.⊖ is CH 3 OSO 3 .sup.⊖ or ##STR120## and n is the number 0 or 1.
Claim 13
Dependent Claim
10 words
A distyrylbenzene according to claim 11, of the formula ##STR121##
Claim 14
Dependent Claim
10 words
A distyrylbenzene according to claim 9, of the formula ##STR122##
Claim 15
Dependent Claim
10 words
A distyrylbenzene according to claim 9, of the formula ##STR123##
Claim 16
Dependent Claim
10 words
A distyrylbenzene according to claim 9, of the formula ##STR124##
Claim 17
Dependent Claim
321 words
A process for the preparation of a distyrylbenzene of the formula ##STR125## in which X and X' independently of one another are --COO-- or --CON(R 4 -- in the o-position, a direct bond, oxygen, sulfur, --O--C 1-3 -alkylene--CON(R 4 )--, --SO 2 N(R 4 )--, --O--C 1-3 -alkylene--COO-- or --OCO--, Y and Y' independently of one another are C 1-20 -alkylene, R 1 and R 1 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 2-4 -alkenyl, or R 1 together with R 2 , or R 1 ' together with R 2 ', is a heterocyclic ring, R 2 and R 2 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 2-4 -alkenyl, or R 2 together with R 1 , or R 2 ' together with R 1 ', is a heterocyclic ring, or R 1 and R 2 , or R 1 ' and R 2 ', together with R 3 are a pyridine or picoline ring, R 3 is hydrogen, unsubstituted or substituted C 1-4 -alkyl or C 3-4 -alkenyl, or together with R 1 and R 2 or with R 1 ' and R 2 ' is a pyridine or picoline ring, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n and n' independently of one another are the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents, which comprises quaternising or protonising 1 mol equivalent of a distyrylbenzene of the formula ##STR126## with 1 or 2 mol equivalents of an alkylating agent or respectively of an acid of the formula R 3 --A, in which formulae the benzene nuclei B and C and X, X', Y, Y', R 1 , R 1 ', R 2 , R 2 ', R 3 and A are as defined above.
Claim 18
Dependent Claim
321 words
A process for the preparation of a distyrylbenzene of the formula ##STR125## in which X and X' independently of one another are --COO-- or --CON(R 4 -- in the o-position, a direct bond, oxygen, sulfur, --O--C 1-3 -alkylene--CON(R 4 )--, --SO 2 N(R 4 )--, --O--C 1-3 -alkylene--COO-- or --OCO--, Y and Y' independently of one another are C 1-20 -alkylene, R 1 and R 1 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 2-4 -alkenyl, or R 1 together with R 2 , or R 1 ' together with R 2 ', is a heterocyclic ring, R 2 and R 2 ' independently of one another are unsubstituted or substituted C 1-8 -alkyl or C 2-4 -alkenyl, or R 2 together with R 1 , or R 2 ' together with R 1 ', is a heterocyclic ring, or R 1 and R 2 , or R 1 ' and R 2 ', together with R 3 are a pyridine or picoline ring, R 3 is hydrogen, unsubstituted or substituted C 1-4 -alkyl or C 3-4 -alkenyl, or together with R 1 and R 2 or with R 1 ' and R 2 ' is a pyridine or picoline ring, R 4 is hydrogen or unsubstituted or substituted C 1-6 -alkyl, A.sup.⊖ is a colourless anion and n and n' independently of one another are the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents, which comprises quaternising or protonising 1 mol equivalent of a distyrylbenzene of the formula ##STR126## with 1 or 2 mol equivalents of an alkylating agent or respectively of an acid of the formula R 3 --A, in which formulae the benzene nuclei B and C and X, X', Y, Y', R 1 , R 1 ', R 2 , R 2 ', R 3 and A are as defined above.
Claim 19
Dependent Claim
224 words
A process for the preparation of a distyrylbenzene of the formula ##STR127## in which Y 4 is C 2-4 -alkylene, R 1 IV is C 1-3 -alkyl or together with R 2 IV is a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 2 IV is C 1-3 -alkyl or together with R 1 IV is a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 3 " is hydrogen or C 1-3 -alkyl, n is the number 0 or 1 and A.sup.⊖ is a colourless anion, which comprises reacting a compound of the formula ##STR128## in a molecular ratio of 1:2 with a compound of the formula ##STR129## in the presence of a strong base, in which formulae Y 4 , R 1 IV and R 2 IV are as defined above and one of the symbols Z 1 and Z 2 is an OCH group and the other is a grouping of the formula ##STR130## in which D 1 is an unsubstituted or substituted alkyl, aryl, cycloalkyl or aralkyl radical, and, if desired, quaternising or protonising the resulting compound of the formula ##STR131## with 2 mol equivalents of an alkylating agent or respectively of an acid of the formula R 3 "--A, in which formulae Y 4 , R 1 IV , R 2 IV , R 3 " and A are as defined above.
Claim 20
Dependent Claim
224 words
A process for the preparation of a distyrylbenzene of the formula ##STR127## in which Y 4 is C 2-4 -alkylene, R 1 IV is C 1-3 -alkyl or together with R 2 IV is a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 2 IV is C 1-3 -alkyl or together with R 1 IV is a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 3 " is hydrogen or C 1-3 -alkyl, n is the number 0 or 1 and A.sup.⊖ is a colourless anion, which comprises reacting a compound of the formula ##STR128## in a molecular ratio of 1:2 with a compound of the formula ##STR129## in the presence of a strong base, in which formulae Y 4 , R 1 IV and R 2 IV are as defined above and one of the symbols Z 1 and Z 2 is an OCH group and the other is a grouping of the formula ##STR130## in which D 1 is an unsubstituted or substituted alkyl, aryl, cycloalkyl or aralkyl radical, and, if desired, quaternising or protonising the resulting compound of the formula ##STR131## with 2 mol equivalents of an alkylating agent or respectively of an acid of the formula R 3 "--A, in which formulae Y 4 , R 1 IV , R 2 IV , R 3 " and A are as defined above.
Claim 21
Dependent Claim
33 words
A process for the fluorescent brightening of organic material, which comprises incorporating a distyrylbenzene of the formula (1) into this material or applying such a distyrylbenzene to the surface of the said material.
Claim 22
Dependent Claim
33 words
A process for the fluorescent brightening of organic material, which comprises incorporating a distyrylbenzene of the formula (1) into this material or applying such a distyrylbenzene to the surface of the said material.
Claim 23
Dependent Claim
18 words
A process according to claim 18, for the fluorescent brightening of polyacrylonitrile or cellulose, as the organic material.
Claim 24
Dependent Claim
15 words
A detergent containing one or more distyrylbenzenes of the formula (1) defined in claim 1.
Claim 25
Dependent Claim
28 words
A detergent according to claim 20, which contains 10 to 70% by weight of a non-ionic surfactant and 1 to 30% by weight of a cationic textile softener.
Claim 26
Dependent Claim
56 words
A detergent according to claim 21, which contains 10 to 70% by weight of a non-ionic surfactant and 1 to 30% by weight of a quaternary derivative of ammonia and/or of imidazoline with 2 long-chain, aliphatic, saturated or unsaturated radicals, as the cationic textile softener, and also a solvent to render it in the liquid form.
Claim 27
Dependent Claim
43 words
A detergent according to claim 22, which contains 1-methyl-1-oleylamidoethyl-2-oleyl-imidazolinium·X.sup.⊖, 1-methyl-1-tallow-amidoethyl-2-tallow-imidazolinium·X.sup..crclbar., di-tallow-dimethyl-ammonium·X.sup.⊖ or a compound of the formula ##STR132## in which Q is C 14-16 -alkyl and X.sup.⊖ is a chloride, bromide, methylsulfate, ethylsulfate, methanesulfonate, ethanesulfonate or toluenesulfonate anion, as the cationic textile softener.
Claim 28
Dependent Claim
17 words
A textile treatment agent containing one or more distyrylbenzenes of the formula (1) defined in claim 1.
Claim 29
Dependent Claim
22 words
A laundry after-treatment agent containing one or more distyrylbenzenes of the formula (1) defined in claim 1 and a cationic textile softener.
References Cited (Backward Citations)
US3271321A
Cited
GB913735A
Cited
DE1923267U
Cited
US3904678A
Cited
DE2039993A1
Cited
US3755446A
Cited
GB1351489A
Cited
US3843718A
Cited
US3927119A
Cited
DE2364396A1
Cited
US4009193A
Cited
DE2721730A1
Cited
GB1522576A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-02-08 | 1985-08-10 | 1986-02-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-02-08 | 1989-08-10 | 1990-02-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-02-08 | 1993-08-10 | 1994-02-09 | $7700.00 | Window Closed / Lapsed |