US3637520A
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US
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Solvent-soluble quaternary ammonium salts of cellulose sulfate
Assignee: Kelso Co
•
Filing: 1969-09-25
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Granted: 1972-01-25
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Expires: 1989-09-25
Abstract
Abstract Quaternary ammonium salts of a colloidal cellulose sulfate having a degree of substitution of at least about two and method of making by adding a water-soluble salt of the colloidal cellulose sulfate to water, then adding a quaternary ammonium salt and optionally a lower alcohol. The resulting products are soluble in many organic solvents. As described in my prior U.S. Pat. application Ser. No. 467,738, the essentially undegraded cellulose sulfate employed as a reactant according to the present invention has a viscosity in a 1 percent aqueous solution in excess of 20 cps. and preferably in excess of 100 cps. as measured with a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and 25* C., and a number of these cellulose sulfates have a viscosity in a 1 percent aqueous solution in excess of 100 cps. The cellulose sulfates employed as reactants according to the present invention and as described in U.S. application Ser. No. 467,738 are further characterized by their reactivity with potassium ions in aqueous media to form a thermoreversible gel.
Inventors
- 👤 Richard G Schweiger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 18:17
CPC Classifications
C; C08; C08B; C08B3/00; C08B3/22; C08B5/00; C08B5/14
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
14 words
The product of claim 1 wherein said quaternary ion is dimethyl di(hydrogenated tallow) ammonium.
Claim 2
Dependent Claim
13 words
The product of claim 1 wherein said quaternary ion is dimethyl di(tallow) ammonium.
Claim 3
Dependent Claim
13 words
The product of claim 1 wherein said quaternary ion is dimethyl di(soya) ammonium.
Claim 4
Dependent Claim
32 words
The product of claim 1 containing a molar excess of said quaternary ammonium ion in an effective amount sufficient to improve the solubility of the product in aliphatic, aromatic and chlorinated solvents.
Claim 5
Dependent Claim
20 words
The product of claim 5 wherein said molar excess of said quaternary ammonium ion is about 0.1 to about 0.3.
Claim 6
Dependent Claim
103 words
A quaternary ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least about 2.0, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media, as measured by a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. at a temperature of 25* C., said cellulose sulfate being further characterized as reactive with potassium ions in aqueous media to form a thermoreversible gel, the quaternary ammonium ion of said salt containing three methyl groups and one long chain alkyl group having from about 14 to about 18 carbon atoms.
Claim 7
Dependent Claim
12 words
The product of claim 7 wherein said quaternary ion trimethyl tallow ammonium.
Claim 8
Dependent Claim
13 words
The product of claim 7 wherein said quaternary ion is trimethyl stearyl ammonium.
Claim 9
Dependent Claim
14 words
The product of claim 7 wherein said quaternary ion is trimethyl (hydrogenated tallow) ammonium.
Claim 10
Dependent Claim
14 words
The product of claim 7 wHerein said quaternary ion is trimethyl (tall oil) ammonium.
Claim 11
Dependent Claim
32 words
The product of claim 7 containing a molar excess of said quaternary ammonium ion in an effective amount sufficient to improve the solubility of the product in aliphatic, aromatic and chlorinated solvents.
Claim 12
Dependent Claim
20 words
The product of claim 12 wherein said molar excess of said quaternary ammonium ion is about 0.1 to about 0.3.
Claim 13
Dependent Claim
104 words
A quaternary ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least about 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive with potassium ions in aqueous media to form a thermoreversible gel, the quaternary ammonium ion of said salt containing two methyl groups, an aromatic group, and a long chain alkyl group containing from about 12 to about 18 carbon atoms.
Claim 14
Dependent Claim
13 words
The products of claim 14 wherein said aromatic group is a phenyl group.
Claim 15
Dependent Claim
14 words
The product of claim 15 wherein said quaternary ion is dimethyl phenyl stearyl ammonium.
Claim 16
Dependent Claim
32 words
The product of claim 14 containing a molar excess of said quaternary ammonium ion in an effective amount sufficient to improve the solubility of the product in aliphatic, aromatic and chlorinated solvents.
Claim 17
Dependent Claim
20 words
The product of claim 17 wherein said molar excess of said quaternary ammonium ion is about 0.1 to about 0.3.
Claim 18
Dependent Claim
106 words
A quaternary ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least about 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer, Model LVF at 60 r.p.m., at a temperature of 25* C., said cellulose sulfate being further characterized as reactive with potassium ions in aqueous media to form a thermoreversible gel, the quaternary ammonium ion of said salt containing two aromatic groups, a methyl group, and a long chain alkyl group having from about 12 to about 18 carbon atoms.
Claim 19
Dependent Claim
12 words
The products of claim 19 wherein said aromatic groups are phenyl groups.
Claim 20
Dependent Claim
14 words
The product of claim 20 wherein said quaternary ion is diphenyl methyl stearyl ammonium.
Claim 21
Dependent Claim
32 words
The product of claim 19 containing a molar excess of said quaternary ammonium ion in an effective amount sufficient to improve the solubility of the product in aliphatic, aromatic and chlorinated solvents.
Claim 22
Dependent Claim
20 words
The product of claim 22 wherein said molar excess of said quaternary ammonium ion is about 0.1 to about 0.3.
Claim 23
Dependent Claim
107 words
A quaternary ammonium salt of an essentially undegraded cellulose sulfate having a D.S. of at least about 2.0, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured with a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive with potassium ions in aqueous media to form a thermoreversible gel, the quaternary ammonium ion of said salt containing one methyl group and three long chain alkyl groups, each of said alkyl groups containing from about eight to about 18 carbon atoms.
Claim 24
Dependent Claim
16 words
The product of claim 24 wherein said quaternary ion is methyl tri(mixed capryl and caprylyl) ammonium.
Claim 25
Dependent Claim
32 words
The product of claim 24 containing a molar excess of said quaternary ammonium ion in an effective amount sufficient to improve the solubility of the product in aliphatic, aromatic and chlorinated solvents.
Claim 26
Dependent Claim
20 words
The product of claim 26 wherein said molar excess of said quaternary ammonium ion is about 0.1 to about 0.3.
Claim 27
Dependent Claim
77 words
The di(oleyl-linoleyl) dImethyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive with potassium ions in aqueous media to form a thermoreversible gel.
Claim 28
Dependent Claim
77 words
The tricaprylyl monomethyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive with potassium ions in aqueous media to form a thermoreversible gel.
Claim 29
Dependent Claim
77 words
The oleyl-linoleyl trimethyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive in aqueous media with potassium ions to form a thermoreversible gel.
Claim 30
Dependent Claim
77 words
The distearyl dimethyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive in aqueous media with potassium ions to form a thermoreversible gel.
Claim 31
Dependent Claim
77 words
The dilauryl dimethyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive in aqueous media with potassium ions to form a thermoreversible gel.
Claim 32
Dependent Claim
77 words
The monostearyl trimethyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive in aqueous media with potassium ions to form a thermoreversible gel.
Claim 33
Dependent Claim
78 words
The stearyl dimethyl benzyl ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least 2, said cellulose sulfate having a viscosity in excess of 20 cps. at a 1 percent concentration in an aqueous media as measured by a Brookfield Synchro Electric Viscometer Model LVF at 60 r.p.m. and a temperature of 25* C., said cellulose sulfate being further characterized as reactive in aqueous media with potassium ions to form a thermoreversible gel.
Claim 34
Dependent Claim
195 words
A thickened water-immiscible organic liquid solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of an essentially undegraded cellulose sulfate having a D.S. of at least about 2, as defined in claim 1, said solvent including therein a solvent selected from the group cOnsisting of a saturated aliphatic or alicyclic hydrocarbon solvent having a dielectric constant in the range of about 1.80 to about 2.10, an olefinic hydrocarbon solvent having a dielectric constant in the range of about 2.00 to about 2.80, an aromatic hydrocarbon solvent having a dielectric constant in the range of about 2.20 to about 2.60, a chlorinated hydrocarbon solvent having a dielectric constant in the range of about 2.00 to about 8.00, and mixtures thereof in an amount sufficient to solubilize said quaternary ammonium salt of cellulose sulfate to a sufficient extent to produce an increase in the viscosity of said water-immiscible organic liquid solvent of about 20 cps. as measured with a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. and a temperature of 25* C. when said salt is added to said organic liquid solvent at a concentration of 5 percent by weight.
Claim 35
Dependent Claim
18 words
The thickened organic liquid solvent of claim 35 wherein said water-immiscible organic liquid solvent is a petroleum distillate.
Claim 36
Dependent Claim
16 words
The thickened organic liquid solvent of claim 35 wherein said water-immiscible organic liquid solvent is gasoline.
Claim 37
Dependent Claim
23 words
The thickened organic liquid solvent of claim 35 wherein said quaternary ammonium cellulose sulfate salt contains a molar excess of quaternary ammonium ions.
Claim 38
Dependent Claim
22 words
The thickened organic liquid solvent of claim 38 wherein said molar excess of quaternary ammonium ions is about 0.1 to about 0.3.
Claim 39
Dependent Claim
25 words
The thickened organic water-immiscible liquid solvent of claim 35 wherein the quaternary ammonium ion present in said cellulose sulfate salt is dimethyl di(hydrogenated tallow) ammonium.
Claim 40
Dependent Claim
18 words
The thickened organic liquid solvent of claim 40 wherein said water-immiscible organic liquid solvent is a petroleum distillate.
Claim 41
Dependent Claim
25 words
The thickened organic liquid solvent of claim 41 wherein said quaternary ammonium cellulose sulfate salt contains a molar excess of dimethyl di(hydrogenated tallow) ammonium ions.
Claim 42
Dependent Claim
24 words
The thickened organic liquid solvent of claim 42 wherein said molar excess of dimethyl di(hydrogenated tallow) ammonium ions is about 0.1 to about 0.3.
Claim 43
Dependent Claim
23 words
Dichlorobenzene solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of cellulose sulfate as defined in claim 1.
Claim 44
Dependent Claim
15 words
The product of claim 44 wherein said salt is dimethyl di(hydrogenated tallow) ammonium cellulose sulfate.
Claim 45
Dependent Claim
169 words
A thickened water-immiscible organic liquid solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least about 2.0 as defined in claim 7, said organic liquid solvent including therein a solvent selected from the group consisting of an olefinic hydrocarbon solvent having a dielectric constant of about 2.00 to about 2.80, an aromatic hydrocarbon solvent having a dielectric constant of about 2.20 to about 2.80, a chlorinated hydrocarbon solvent having a dielectric constant of about 2.40 to about 10.00, and mixtures thereof in an amount sufficient to solubilize said quaternary ammonium salt of cellulose sulfate to a sufficient extent to produce an increase in the viscosity of said water-immiscible organic liquid solvent of about 20 cps. as measured with a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. and a temperature of 25* C. when said salt is added to said organic liquid solvent at a concentration of 5 percent by weight.
Claim 46
Dependent Claim
169 words
A thickened water-immiscible organic liquid solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of an essentially undegraded colloidal cellulose sulfate having a D.S. of at least about 2.0 as defined in claim 14, said organic liquid solvent including therein a solvent selected from the group consisting of an oLefinic hydrocarbon solvent having a dielectric constant of about 2.00 to about 2.80, an aromatic hydrocarbon solvent having a dielectric constant of about 2.20 to about 2.80, a chlorinated hydrocarbon solvent having a dielectric constant of about 2.40 to about 10.00, and mixtures thereof in an amount sufficient to solubilize said quaternary ammonium salt of cellulose sulfate to a sufficient extent to produce an increase in the viscosity of said water-immiscible organic liquid solvent of about 20 cps. as measured with a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. and a temperature of 25* C. when said salt is added to said organic liquid solvent at a concentration of 5 percent by weight.
Claim 47
Dependent Claim
195 words
A thickened water-immiscible organic liquid solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of an essentially undegraded cellulose sulfate having a D.S. of at least about 2, as defined in claim 19, said solvent including therein a solvent selected from the group consisting of a saturated aliphatic or alicyclic hydrocarbon solvent having a dielectric constant in the range of about 1.80 to about 2.10, an olefinic hydrocarbon solvent having a dielectric constant in the range of about 2.00 to about 2.80, an aromatic hydrocarbon solvent having a dielectric constant in the range of about 2.20 to about 2.60, a chlorinated hydrocarbon solvent having a dielectric constant in the range of about 2.00 to about 8.00, and mixtures thereof in an amount sufficient to solubilize said quaternary ammonium salt of cellulose sulfate to a sufficient extent to produce an increase in the viscosity of said water-immiscible organic liquid solvent of about 20 cps. as measured with a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. and a temperature of 25* C. when said salt is added to said organic liquid solvent at a concentration of 5 percent by weight.
Claim 48
Dependent Claim
23 words
Dichlorobenzene solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of cellulose sulfate as defined in claim 19.
Claim 49
Dependent Claim
15 words
The product of claim 49 wherein said salt is diphenyl methyl stearyl ammonium cellulose sulfate.
Claim 50
Dependent Claim
195 words
A thickened water-immiscible organic liquid solvent containing an amount effective to thicken said solvent of a quaternary ammonium salt of an essentially undegraded cellulose sulfate having a D.S. of at least about 2, as defined in claim 34, said solvent including therein a solvent selected from the group consisting of a saturated aliphatic or alicyclic hydrocarbon solvent having a dielectric constant in the range of about 1.80 to about 2.10, an olefinic hydrocarbon solvent having a dielectric constant in the range of about 2.00 to about 2.80, an aromatic hydrocarbon solvent having a dielectric constant in the range of about 2.20 to about 2.60, a chlorinated hydrocarbon solvent having a dielectric constant in the range of about 2.00 to about 8.00, and mixtures thereof in an amount sufficient to solubilize said quaternary ammonium salt of cellulose sulfate to a sufficient extent to produce an increase in the viscosity of said water-immiscible organic liquid solvent of about 20 cps. as measured with a Brookfield Synchro Electric Viscometer, Model LVF, at 60 r.p.m. and a temperature of 25* C. when said salt is added to said organic liquid solvent at a concentration of 5 percent by weight.
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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) | 1975-01-24 | 1975-07-26 | 1976-01-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-01-24 | 1979-07-26 | 1980-01-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-01-24 | 1983-07-26 | 1984-01-25 | $7700.00 | Window Closed / Lapsed |