Patent # 5,739,327 containing 12 claims, issued 04-14-1998. Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts. 

N-alkyl ammonium acetonitrile bleach activators

Patent # 5,741,437 containing 26 claims, issued 04-21-1998. Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts.

N-alkyl ammonium acetonitrile bleach activators

Patent # 5,959,104 containing 1 claim, issued 09-28-1999. Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts.

N-alkyl ammonium acetonitrile bleach activators

Patent # 5,958,289 containing 5 claim, issued 09-28-1999. Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts.

Granular N-alkyl ammonium acetontrile compositions

Patent # 5,888,419 containing 16 claims, issued 03-30-1999. Granules are provided that are useful for oxidizing applications when the granules are dissolved in the presence of an active oxygen source. These granules include a salt having the structure of Formula I [Figure] wherein A is a saturated ring formed by a plurality of atoms in addition to the N₁ atom, the saturated ring atoms including at least one carbon atom and at least one of O, S, and N atoms, the substituent R₁ bound to the N₁ atom of the Formula I structure including either (a) a C_1-24 alkyl or alkoxylated alkyl where the alkoxy is C_2-4, (b) a C_4-24 cycloalkyl, (c) a C_7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C_2-4, or (e) --CR₂ R₃ C.tbd.N where R₂ and R₃ are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, the R₂ and R₃ substituents being each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, Z is in the range of 0 to 10, and wherein Y is a counterion. The salt is carried by, coated with, or admixed with a solid particulate such as silica gel, silicic acid, silicate, aluminum oxide, clay, aluminum silicate, or mixtures thereof.

Process for preparing N-alkyl ammonium acetonitrile compounds

Patent # 6,235,218 containing 9 claims, issued 05-22-2001. A process is provided for the preparation of a compound having the structure of Formula I The process includes reacting a heterocyclic amine with a monoaldehyde or a dialdehyde in a pH range of from about 8 to 14 and then quaternizing the so-reacted heterocyclic amine with an alkylating agent at a pH of not less than about 2. The use of pH control substantially prevents formation of an undesirable protonated reaction intermediate.

Liquid compositions containing N-alkyl ammonium acetonitrile salts

Patent # 6,010,994 containing 11 claims, issued 01-04-2000. The invention provides liquid cleaning or bleaching compositions containing compounds having the structure of Formula I [Figure] wherein A is a saturated ring formed by five atoms in addition to the N₁ atom, the five saturated ring atoms being four carbon atoms and a heteroatom, the substituent R₁ bound to the N₁ atom of the Formula I structure including either (a) a C_1-24 alkyl or alkoxylated alkyl where the alkoxy is C_2-4, (b) a C_4-24 cycloalkyl, (c) a C_7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C_2-4, or (e) --CR₂ R₃ CN where R₂ and R₃ are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, the R₂ and R₃ substituents are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, and wherein Y is a generally anionic counterion and Z is in the range of 0 to 10. Additional, adjunct materials commonly found in liquid cleaning and bleaching compositions can be added.

Liquid compositions containing N-alkyl ammonium acetonitrile salts

Patent # 6,046,150 containing 18 claims, issued 04-04-2000. The invention provides liquid cleaning or bleaching compositions containing compounds having the structure of Formula I [Figure] wherein A is a saturated ring formed by five atoms in addition to the N₁ atom, the five saturated ring atoms being four carbon atoms and a heteroatom, the substituent R₁ bound to the N₁ atom of the Formula I structure including either (a) a C_1-24 alkyl or alkoxylated alkyl where the alkoxy is C_2-4, (b) a C_4-24 cycloalkyl, (c) a C_7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C_2-4, or (e) --CR₂ R₃ CN where R₂ and R₃ are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, the R₂ and R₃ substituents are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, and wherein Y is a generally anionic counterion and Z is in the range of 0 to 10. Additional, adjunct materials commonly found in liquid cleaning and bleaching compositions can be added.

Mixed peroxygen activator compositions

Patent # 5,814,242 containing 12 claims, issued 09-29-1998. Preferred embodiments of the invention are heterocyclic cationic activators with the structure of Formula I [Figure] wherein A is a saturated ring formed by a plurality of atoms in addition to the N₁ atom, the saturated ring atoms including at least one carbon atom and at least one of O, S, and N atoms, the substituent R₁ bound to the N₁ atom of the Formula I structure including either (a) a C_1-24 alkyl or alkoxylated alkyl where the alkoxy is C_2-4, (b) a C_4-24 cycloalkyl, (c) a C_7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C_2-4, or (e) --CR₂ R₃ C.tbd.N where R₂ and R₃ are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, the R₂ and R₃ substituents being each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, Z is in the range of 0 to 10, and wherein Y is an anionic peracid activator. When these are dissolved in an aqueous solution in the presence of an active oxygen source, coactivation will occur for improved bleaching.

N-alkyl ammonium acetonitrile salts, methods therefore and compositions therewith

Patent application # 20030080319A1 containing 1 claim, issued 05-01-2003. Substantially solid compositions are provided having therein a compound with the structure of Formula I 1 wherein A is a saturated ring formed by a plurality of iatoms in addition to the N₁ atom, the saturated ring atoms including at least one carbon atom and at least one of O, S, and N atoms, the substituent R₁ bound to the N₁ atom of the Formula I structure including either (a) a C_1-24 alkyl or alkoxylated alkyl where the alkoxy is C_2-4, (b) a C_4-24 cycloalkyl, (c) a C_7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C_2-4, or (e) —CR₂R₃C≡N where R₂ and R₃ are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, the R₂ and R₃ substituents being each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, Z is a value in the range of 0 to 10, and wherein Y is monovalent or multivalent and is sulfate, bisulfate, tosylate, or mixtures of sulfate and bisulfate as counterion. These compositions have reduced water uptake due to the Formula I compound. The compositions are particularly well suited to bleaching and cleaning compositions formulated to include a source of active oxygen.

Dimeric N-Alkyl ammonium acetonitrile bleach activators

Patent # 5,877,315 containing 8 claims, issued 03-02-1999. Bleaching compositions are provided that comprise two nitrile groups where each nitrile is bonded to a quaternary nitrogen through a methylene unit. The quaternary nitrogens are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitriles for bleaching applications.

Dimeric N-alkyl ammonium acetonitrile bleach activators

Patent # 6,017,464 containing 6 claims, issued 01-25-2000. Bleaching compositions are provided that comprise two nitrile groups where each nitrile is bonded to a quaternary nitrogen through a methylene unit. The quaternary nitrogens are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrites for bleaching applications.

Granular N-alkyl ammonium acetonitrile compositions

Patent # 6,183,665 containing 23 claims, issued 02-06-2001. Granules are provided that are useful for oxidizing applications when the granules are dissolved in the presence of an active oxygen source. These granules include a salt having the structure of Formula I [Figure] wherein A is a saturated ring formed by a plurality of atoms in addition to the N₁ atom, the saturated ring atoms including at least one carbon atom and at least one of O, S, and N atoms, the substituent R₁ bound to the N₁ atom of the Formula I structure including either (a) a C_1-24 alkyl or alkoxylated alkyl where the alkoxy is C_2-4, (b) a C_4-24 cycloalkyl, (c) a C_7-24 alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C_2-4, or (e) --CR₂ R₃ C.tbd.N where R₂ and R₃ are each H, a C_1-24 alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, the R₂ and R₃ substituents being each H, a C_1-24 alky, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C_2-4, Z is in the range of 0 to 10, and wherein Y is a counterion. An improved granule is produced when the salt is carried by, coated with, or admixed with a solid particulate such as silica gel, silicic acid, silicate, aluminum oxide, clay, or mixtures thereof.

N-alkyl ammonium acetonitrile activators in dense gas cleaning and method

Patent # 5,792,218 containing 21 claims, issued 08-11-1998. Nitrile activators, such as N-alkyl ammonium acetonitrile activators, are combined with a source of active oxygen as cleaning and bleaching compositions. Preferred activator embodiments of the invention include salts of N-methyl morpholinium acetonitrile, N-butyl morpholinium acetonitrile, N-hexyl morpholinium acetonitrile, and N-octyl morpholinium acetonitrile. A particularly preferred activator embodiment is an N-methyl morpholinium acetonitrile salt. The nitrile and active oxygen react to form a bleaching agent which is applied to a stain on an article. The treated stain is contacted with dense gas so as to provide substantially non-aqueous stain removal. One embodiment is a composition in which the nitrile and active oxygen are disposed in the dense carbon dioxide.

 

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