US4250327A
Expired / Lapsed
US
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Polymeric yellow colorant
Assignee: Dynapol Shareholders Liquidating Trust
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Filing: 1979-01-02
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Granted: 1981-02-10
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Expires: 1999-01-02
Abstract
Abstract A group of water-soluble polymeric yellow colors and their preparation is disclosed. These colors comprise a plurality of units of a chromophore of the formula ##STR1## wherein M + is a pharmaceutically acceptable monovalent cation attached directly to amine units present in a nonchromophoric polymer backbone. In a preferred embodiment of the invention the backbone is a homopolymer or copolymer of vinylamine. These colorants find special utility as nonabsorbable colorants for edibles, especially foods and beverages, where their yellow hue is an excellent color match for existing monomeric azo food colors such as tartrazine, and as components of acid-insoluble pigment lakes which are themselves suitable for use in edibles.
Inventors
- 👤 Daniel J. Dawson
- 👤 Kenneth M. Otteson
- 👤 Roman Davis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:40
CPC Classifications
C; C09; C09B; C09B69/00; C09B69/10; C09B69/109; A; A23; A23L; A23L5/00; A23L5/40; A23L5/42; A23L5/47
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
107 words
A polymeric yellow colorant soluble in room temperature pH 7 water to an extent of not less than 1,000 ppm by weight, and comprising (1) an amine containing, nonchromophoric, essentially linear backbone polymer, said backbone polymer having a molecular weight of from 1,000 to 200,000 daltons and (2) a plurality of chromophores covalently depending from the amine moieties of said backbone polymer, said chromophores having the basic nucleus: ##STR45## wherein M + is a pharmacologically acceptable cation, and said pendant chromophores being directly covalently linked to said backbone polymer through the amine moieties thereof via an aromatic carbon-nitrogen single bond and defining a nitrosulfanilic acid structure therewith.
Claim 2
Dependent Claim
107 words
A polymeric yellow colorant soluble in room temperature pH 7 water to an extent of not less than 1,000 ppm by weight, and comprising (1) an amine containing, nonchromophoric, essentially linear backbone polymer, said backbone polymer having a molecular weight of from 1,000 to 200,000 daltons and (2) a plurality of chromophores covalently depending from the amine moieties of said backbone polymer, said chromophores having the basic nucleus: ##STR45## wherein M + is a pharmacologically acceptable cation, and said pendant chromophores being directly covalently linked to said backbone polymer through the amine moieties thereof via an aromatic carbon-nitrogen single bond and defining a nitrosulfanilic acid structure therewith.
Claim 3
Dependent Claim
20 words
The polymeric yellow colorant as defined by claim 1, said plurality of chromophores (2) ranging from between 10 and 2000.
Claim 4
Dependent Claim
17 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer being a polymer of vinylamine.
Claim 5
Dependent Claim
14 words
The polymeric yellow colorant as defined by claim 3, said backbone polymer being homopolyvinylamine.
Claim 6
Dependent Claim
70 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR46## wherein A, A' and A" are independently selected from the group consisting of: ##STR47## and further wherein n, m, p and q are numbers such that the sum of n, m, p and q is from 40 to 8000 and n is not less than 0.2 times the sum of m+p+q.
Claim 7
Dependent Claim
23 words
The polymeric yellow colorant as defined by claim 5, wherein A, A' and A" are independently selected from the group consisting of: ##STR48##
Claim 8
Dependent Claim
64 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR49## wherein n, m, p and q are numbers such that the sum of n, m, p and q is from 40 to 8000 and n is not less than 0.2 times the sum of m+p+q, and wherein n+m+p is from 0.3 to 10 times q.
Claim 9
Dependent Claim
100 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR50## wherein R 2 is hydrogen or lower alkyl having from 1 to 4 carbon atoms and R 3 and R 4 are independently hydrogen, methyl or ethyl wherein n, m, p and q are numbers such that the sum of n, m, p and q is from 40 to 8000 and n is not less than 0.2 times the sum of m+p+q, and wherein n+m is from 0.3 to 10 times p+q and q is from 0.01 to 0.4 times p.
Claim 10
Dependent Claim
27 words
The polymeric yellow colorant as defined by claims 7 or 85, wherein n+m+p+q is from 500 to 7000, and n+m+p is from 1 to 7 times q.
Claim 11
Dependent Claim
18 words
The polymeric yellow colorant as defined by claim 9, wherein n+m+p is from 1.25 to 4 times q.
Claim 12
Dependent Claim
87 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR51## wherein R 2 is hydrogen and R 3 and R 4 are independently hydrogen, wherein n, m, p and q are numbers such that the sum of n, m, p and q is from 80 to 2000 and n is not less than 0.2 times the sum of m+p+q, and wherein n+p+q equals from 0.5 to 4 times m and n+p equals from 1 to 7 times q.
Claim 13
Dependent Claim
94 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR52## wherein R 2 is hydrogen or lower alkyl having from 1 to 4 carbon atoms and R 3 and R 4 are independently hydrogen, methyl or ethyl, wherein n, m, p and q are numbers such that the sum of n, m, p and q is from 80 to 2000, n+p+q equals from 0.5 to 4 times m, n equals from 1 to 7 times p+q, and q equals from 0.02 to 0.1 times p.
Claim 14
Dependent Claim
63 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula, ##STR53## wherein n is a number from 150 to 500, m is a number from 200 to 600, p is a number from 250 to 700 and q is a number from 25 to 100, such that n:m:p:q are in a ratio of about 5:7:8:10.5.
Claim 15
Dependent Claim
20 words
The polymeric yellow colorant as defined by claims 8 or 12, wherein each R 3 and R 4 is hydrogen.
Claim 16
Dependent Claim
15 words
The polymeric yellow colorant as defined by claim 14, wherein each R 2 is hydrogen.
Claim 17
Dependent Claim
16 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer having essentially no crosslinks.
Claim 18
Dependent Claim
25 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer comprising only covalent bonds stable under the conditions of the mammalian gastrointestinal tract.
Claim 19
Dependent Claim
43 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer being selected from the group consisting of carbon-nitrogen aliphatic secondary amine backbone polymer; carbon-oxygen aliphatic ether, pendant amino group backbone polymer; alkyl carbon-carbon, pendant amino group backbone polymer; and copolymers thereof.
Claim 20
Dependent Claim
23 words
The polymeric yellow colorant as defined by claim 18, said backbone polymer having a molecular weight of from about 2,000 to 100,000 daltons.
Claim 21
Dependent Claim
20 words
The polymeric yellow colorant as defined by claim 19, said backbone polymer being an essentially linear alkyl carbon-carbon backbone polymer.
Claim 22
Dependent Claim
34 words
The polymeric yellow colorant as defined by claim 3, said backbone polymer being a copolymer of vinylamine with a comonomer selected from the group consisting of vinyl sulfonate, acrylic acid, methacrylic acid and vinylphosphonate.
Claim 23
Dependent Claim
17 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer being a polymer of ethyleneimine.
Claim 24
Dependent Claim
57 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR54## wherein n, m, p and q are numbers such that the sum of n, m, p and q is from 40 to 8000 and n is not less than 0.2 times the sum of m, p and q.
Claim 25
Dependent Claim
18 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer being a polymer of lower alkylamine.
Claim 26
Dependent Claim
18 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer being a polymer of dilower dialkylamine.
Claim 27
Dependent Claim
17 words
The polymeric yellow colorant as defined by claim 2, said backbone polymer being a polymer of aminoethylacrylate.
Claim 28
Dependent Claim
37 words
The polymeric yellow colorant as defined by any of claims 2, 5, 7, 8, 11 or 12, wherein M + is selected from the group consisting of Na + , K + and NH 4 + .
Claim 29
Dependent Claim
16 words
The polymeric yellow colorant as defined by claim 27, wherein M + is Na + .
Claim 30
Dependent Claim
34 words
The polymeric yellow colorant as defined by claim 1, the amine moieties comprising said amine containing, nonchromophoric, essentially linear backbone polymer being secondary amine groups present and directly covalently bonded within said backbone polymer.
Claim 31
Dependent Claim
29 words
The polymeric yellow colorant as defined by claim 1, the amine moieties comprising said amine containing, nonchromophoric, essentially linear backbone polymer being primary amine groups pendant from said backbone.
Claim 32
Dependent Claim
29 words
The polymeric yellow colorant as defined by claim 1, the amine moieties comprising said amine containing, nonchromophoric, essentially linear backbone polymer being secondary amine groups pendant from said backbone.
Claim 33
Dependent Claim
24 words
The polymeric yellow colorant as defined by claim 29, containing residual, non-chromophore-substituted secondary amine groups present and directly covalently bonded within said backbone polymer.
Claim 34
Dependent Claim
21 words
The polymeric yellow colorant as defined by claims 30 or 31, containing residual, non-chromophore-substituted secondary amine groups pendant from said backbone.
Claim 35
Dependent Claim
21 words
The polymeric yellow colorant as defined by claim 32, at least a portion of said residual, non-chromophore-substituted amine groups being acetylated.
Claim 36
Dependent Claim
14 words
The polymeric yellow colorant as defined by claim 1, said backbone polymer comprising copolyvinylamine/vinylsulfonate.
Claim 37
Dependent Claim
27 words
The polymeric yellow colorant as defined by any of claims 1, 3, 18, 29, 30, 31, 32, or 34, said backbone polymer further containing water-solubilizing polar groups.
Claim 38
Dependent Claim
14 words
The polymeric yellow colorant as defined by claim 30, said backbone polymer being homopolyvinylamine.
Claim 39
Dependent Claim
25 words
The polymeric yellow colorant as defined by claim 37, containing residual, non-chromophore-substituted primary amine groups, at least a portion of said residual groups being acetylated.
Claim 40
Dependent Claim
16 words
The polymeric yellow colorant as defined by claims 29 or 32, said backbone polymer being polyethyleneimine.
Claim 41
Dependent Claim
28 words
The polymeric yellow colorant as defined by claim 32, said backbone polymer being polyethyleneimine and at least a portion of said residual, non-chromophore-substituted secondary amine groups being acetylated.
Claim 42
Dependent Claim
29 words
The polymeric yellow colorant as defined by claims 30 or 31, or said amine groups being pendant to the backbone polymer through a 1 to 4 carbon alkyl bridge.
Claim 43
Dependent Claim
29 words
The polymeric yellow colorant as defined by claims 30 or 31, said amine groups being pendant to the backbone polymer through a 2 to 4 carbon carboxylate ester bridge.
Claim 44
Dependent Claim
29 words
The polymeric yellow colorant as defined by claims 30 or 31, said amine groups being pendant to the backbone polymer through a 2 to 4 carbon alkyl ether bridge.
Claim 45
Dependent Claim
28 words
The polymeric yellow colorant as defined by claims 30 or 31, said amine groups being pendant to the backbone polymer through a 2 to 4 carbon alkyleneamine bridge.
Claim 46
Dependent Claim
21 words
The polymeric yellow colorant as defined by claim 33, at least a portion of said residual, non-chromophore-substituted amine groups being acetylated.
Claim 47
Dependent Claim
17 words
The polymeric yellow colorant as defined by claim 33, said backbone polymer further containing water-solubilizing polar groups.
Claim 48
Dependent Claim
64 words
The polymeric yellow colorant as defined by claim 1, consisting essentially of recurring units of the structural formula: ##STR55## wherein n+m is a number from 900 to 3500, p is a number from 600 to 2000, and q is a number from 10 to 100, n+m, p and q being further defined as being in a ratio of about 6 to 4 to 0.1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-10 | 1984-08-11 | 1985-02-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-10 | 1988-08-11 | 1989-02-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-10 | 1992-08-11 | 1993-02-10 | $7700.00 | Window Closed / Lapsed |