US4751015A
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US
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Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions
Assignee: Lever Brothers Co
•
Filing: 1987-03-17
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Granted: 1988-06-14
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Expires: 2007-03-17
Abstract
Abstract A bleach precursor compound, its peroxygen acid derivative, and detergent compositions containing these materials are disclosed herein. The bleach precursor structurally comprises a quaternized ammonium or phosphonium group linked to a carbonate moiety having a leaving group. Upon perhydrolysis in the presence of hydrogen peroxide and a basic aqueous media, there is generated a peroxycarbonic acid bleach.
Inventors
- 👤 Robert W. Humphreys
- 👤 Stephen A. Madison
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 09:03
CPC Classifications
C; C07; C07C; C07C215/00; C07C215/02; C07C215/40; C11; C11D; C11D3/00; C11D3/39; C11D3/3902; C11D3/3905; C11D3/3907; C11D3/393; C11D3/3917; C11D3/392; C11D3/3927
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
286 words
A bleach precursor compound having the formula: ##STR16## wherein: R 1 , R 2 and R 3 are each a radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aryl phenyl, hydroxyalkyl, polyoxyalkylene, and R 4 OCOL; or two or more of R 1 , R 2 , and R 3 together form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; or at least one of R 1 , R 2 , and R 3 is attached to R 4 to form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; R 4 is selected from a bridging group consisting of alkylene, cy cloalkylene, alkylenephenylene, phenylene, arylene, and polyalkoxylene; and wherein the briding group can be unsubstituted or substituted with C 1 -C 20 atoms selected from alkyl, alkenyl, benzyl, phenyl and aryl radicals; Z - is a monovalent or multivalent anion leading to charge neutrality when combined with Q + in the appropriate ratio and wherein Z - is sufficiently oxidatively stable not to interfere significantly with bleaching by a peroxy carbonic acid; Q is nitrogen or phosphorous; and L is selected from the group consisting of: ##STR17## wherein R 5 and R 6 are a C 1 -C 12 alkyl group, R 7 is H or R 5 , and Y is selected from the group consisting of --SO - 3 M + , --COO - M + , --SO - 4 M + , --N + (R 5 ) 3 X - , NO 2 , OH, and O←N(R 5 ) 2 and mixtures thereof; M + is a cation which provides solubility to the precursor, and X - is an anion which provides solubility to the precursor.
Claim 2
Dependent Claim
286 words
A bleach precursor compound having the formula: ##STR16## wherein: R 1 , R 2 and R 3 are each a radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aryl phenyl, hydroxyalkyl, polyoxyalkylene, and R 4 OCOL; or two or more of R 1 , R 2 , and R 3 together form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; or at least one of R 1 , R 2 , and R 3 is attached to R 4 to form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; R 4 is selected from a bridging group consisting of alkylene, cy cloalkylene, alkylenephenylene, phenylene, arylene, and polyalkoxylene; and wherein the briding group can be unsubstituted or substituted with C 1 -C 20 atoms selected from alkyl, alkenyl, benzyl, phenyl and aryl radicals; Z - is a monovalent or multivalent anion leading to charge neutrality when combined with Q + in the appropriate ratio and wherein Z - is sufficiently oxidatively stable not to interfere significantly with bleaching by a peroxy carbonic acid; Q is nitrogen or phosphorous; and L is selected from the group consisting of: ##STR17## wherein R 5 and R 6 are a C 1 -C 12 alkyl group, R 7 is H or R 5 , and Y is selected from the group consisting of --SO - 3 M + , --COO - M + , --SO - 4 M + , --N + (R 5 ) 3 X - , NO 2 , OH, and O←N(R 5 ) 2 and mixtures thereof; M + is a cation which provides solubility to the precursor, and X - is an anion which provides solubility to the precursor.
Claim 3
Dependent Claim
35 words
The precursor of claim 1 wherein M + is a hydrogen, alkali metal, ammonium or alkyl or hydroxyalkyl substituted ammonium cation, and X - is a halide, hydroxide, phosphate, sulfate, methyl sulfate or acetate anion.
Claim 4
Dependent Claim
21 words
The precursor of claim 1 wherein L has the formula: ##STR18## wherein M + is a sodium, potassium or ammonium cation.
Claim 5
Dependent Claim
70 words
The precursor of claim 1 wherein Q is nitrogen and R 1 , R 2 and R 3 are each the same or different and selected from C 1 -C 20 atom radicals selected from the group consisting of alkyl, alkylaryl, benzyl, hydroxyalkyl, and heterocyclic rings containing the quaternary nitrogen where R 1 and R 4 or R 1 and R 2 are joined together, and mixtures of groups thereof.
Claim 6
Dependent Claim
18 words
The precursor of claim 4 wherein R 1 is selected from short-chain C 1 -C 4 alkyl radicals.
Claim 7
Dependent Claim
24 words
The precursor of claim 5 wherein R 2 and R 3 are each a longer chain C 7 -C 20 alkyl or alkylaryl radical.
Claim 8
Dependent Claim
22 words
The precursor of claim 6 wherein said longer chain radical is selected from the group consisting of benzyl, lauryl and stearyl groups.
Claim 9
Dependent Claim
38 words
The precursor of claim 1 wherein R 4 is selected from a bridging group consisting of C 2 -C 20 alkylene C 6 -Cl 2 phenylene, C 5 -C 20 cycloalkylene, and C 8 -C 20 alkylphenylene groups.
Claim 10
Dependent Claim
25 words
The precursor of claim 8 wherein the R 4 bridging group is a C 2 -C 6 alkylene or C 6 -C 12 phenylene group.
Claim 11
Dependent Claim
18 words
The precursor of claim 4 wherein said heterocyclic ring is selected from pyridine, morpholine, pyrrolidone, piperidine and piperazine.
Claim 12
Dependent Claim
12 words
The precursor of claim 1 wherein Y is a sulfonic acid salt.
Claim 13
Dependent Claim
13 words
The precursor of claim 1 wherein the compound is 2-(N,N,N-trimethylammonium)ethyl 4-sulfophenyl carbonate salt.
Claim 14
Dependent Claim
13 words
The precursor of claim 1 wherein the compound is 2-(N-benzyl-N,N-dimethylammonium)ethyl 4-sulphophenyl carbonate salt.
Claim 15
Dependent Claim
13 words
The precursor of claim 1 wherein the compound is 2-(N-butyl-N,N-diemthylammonium)ethyl 4-sulfophenyl carbonate salt.
Claim 16
Dependent Claim
13 words
The precursor of claim 1 wherein the compound is 2-[4-(N,N,N-trimethylammonium)phenyl]ethyl 4-sulfophenyl carbonate salt.
Claim 17
Dependent Claim
13 words
The precursor of claim 1 wherein the compound is 3-(1,1-dimethylpiperidinium) 4-sulfophenyl carbonate salt.
Claim 18
Dependent Claim
13 words
The precursor of claim 1 wherein the compound is 4-(1,1-dimethylpiperidinium) 4-sulfophenyl carbonate salt.
Claim 19
Dependent Claim
346 words
A bleaching-detergent composition comprising: (i) from 1 to 60% of a peroxygen compound capable of yielding hydrogen peroxide in an aqueous solution; (ii) from 0.1 to 40% of a bleach precursor having the formula: ##STR19## wherein: R 1 , R 2 and R 3 are each a radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aryl, phenyl, hydroxyalkyl, polyoxyalkylene, and R 4 OCOL; or two or more of R 1 , R 2 and R 3 together form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; or at least one of R 1 , R 2 and R 3 is attached to R 4 to form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; R 4 is selected from a bridging group consisting of alkylene, cycloalkylene, alkylenephenylene, phenylene, arylene, and polyalkoxylene; and wherein the briding group can be unsubstituted or substituted with C 1 -C 20 atoms selected from alkyl, alkenyl, benzyl, phenyl and aryl radicals; Z - is a monovalent or multivalent anion leading to charge neutrality when combined with Q + in the appropriate ratio and wherein Z - is sufficiently oxidatively stable not to interfere significantly with bleaching by a peroxy carbonic acid; Q is nitrogen or phosphorous; and L is a leaving group is selected from the group consisting of: ##STR20## wherein R 5 and R 6 are a C 1 -C 12 alkyl group, R 7 is H or R 5 , and Y is selected from the group consisting of, --SO - 3 M + , --COO - M + , --SO - 4 M + , --N + (R 5 ) 3 X - , NO 2 , OH, and O--N(R 5 ) 2 and mixtures thereof; M + is a cation which provides solubility to the precursor, and X - is an anion which provides solubility to the precursor; (iii) from 0 to 50% of a surfactant selected from the group consisting of nonionic, anionic, amphoteric and surface active mixtures thereof; and (iv) from 0 to 80% of a detergent builder.
Claim 20
Dependent Claim
346 words
A bleaching-detergent composition comprising: (i) from 1 to 60% of a peroxygen compound capable of yielding hydrogen peroxide in an aqueous solution; (ii) from 0.1 to 40% of a bleach precursor having the formula: ##STR19## wherein: R 1 , R 2 and R 3 are each a radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkaryl, aryl, phenyl, hydroxyalkyl, polyoxyalkylene, and R 4 OCOL; or two or more of R 1 , R 2 and R 3 together form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; or at least one of R 1 , R 2 and R 3 is attached to R 4 to form an alkyl substituted or unsubstituted nitrogen-containing heterocyclic ring system; R 4 is selected from a bridging group consisting of alkylene, cycloalkylene, alkylenephenylene, phenylene, arylene, and polyalkoxylene; and wherein the briding group can be unsubstituted or substituted with C 1 -C 20 atoms selected from alkyl, alkenyl, benzyl, phenyl and aryl radicals; Z - is a monovalent or multivalent anion leading to charge neutrality when combined with Q + in the appropriate ratio and wherein Z - is sufficiently oxidatively stable not to interfere significantly with bleaching by a peroxy carbonic acid; Q is nitrogen or phosphorous; and L is a leaving group is selected from the group consisting of: ##STR20## wherein R 5 and R 6 are a C 1 -C 12 alkyl group, R 7 is H or R 5 , and Y is selected from the group consisting of, --SO - 3 M + , --COO - M + , --SO - 4 M + , --N + (R 5 ) 3 X - , NO 2 , OH, and O--N(R 5 ) 2 and mixtures thereof; M + is a cation which provides solubility to the precursor, and X - is an anion which provides solubility to the precursor; (iii) from 0 to 50% of a surfactant selected from the group consisting of nonionic, anionic, amphoteric and surface active mixtures thereof; and (iv) from 0 to 80% of a detergent builder.
Claim 21
Dependent Claim
24 words
The composition of claim 18 wherein the surfactant ranges from 4 to 50% and the detergent builder ranges from 5 to 70% by weight.
Claim 22
Dependent Claim
35 words
The composition of claim 18 wherein M + is a hydrogen, alkali metal, ammonium or alkyl or hydroxyalkyl substituted ammonium cation, and X - is a halide, hydroxide, phosphate, sulfate, methyl sulfate or acetate anion.
Claim 23
Dependent Claim
21 words
The composition of claim 18 wherein L has the formula: ##STR21## wherein M + is a sodium, potassium or ammonium cation.
Claim 24
Dependent Claim
70 words
The composition of claim 18 wherein Q is nitrogen and R 1 , R 2 and R 3 are each the same or different and selected from C 1 -C 20 atom radicals selected from the group consisting of alkyl, alkylaryl, benzyl, hydroxyalkyl, and heterocyclic rings containing the quaternary nitrogen where R 1 and R 4 or R 1 and R 2 are joined together, and mixtures of groups thereof.
Claim 25
Dependent Claim
18 words
The composition of claim 22 wherein R 1 is selected from short-chain C 1 -C 4 alkyl radicals.
Claim 26
Dependent Claim
24 words
The composition of claim 23 wherein R 2 and R 3 are each a longer chain C 7 -C 20 alkyl or alkylaryl radical.
Claim 27
Dependent Claim
22 words
The composition of claim 24 wherein said longer chain radical is selected from the group consisting of benzyl, lauryl and stearyl groups.
Claim 28
Dependent Claim
38 words
The composition of claim 18 wherein R 4 is selected from a bridging group consisting of C 2 -C 20 alkylene, C 6 -C 12 phenylene, C 5 -C 20 cycloalkylene, and C 8 -C 20 alkylphenylene groups.
Claim 29
Dependent Claim
25 words
The composition of claim 26 wherein the R 4 bridging group is a C 2 -C 6 alkylene or C 6 -C 12 phenylene group.
Claim 30
Dependent Claim
18 words
The composition of claim 22 wherein said heterocyclic ring is selected from pyridine, morpholine, pyrrolidone, piperidine and piperazine.
Claim 31
Dependent Claim
12 words
The composition of claim 18 wherein Y is a sulfonic acid salt.
Claim 32
Dependent Claim
13 words
The composition of claim 18 wherein the precursor is 2-(N,N,N-trimethylammonium)ethyl 4-sulfophenyl carbonate salt.
Claim 33
Dependent Claim
13 words
The composition of claim 18 wherein the precursor is 2-(N-benzyl-N,N-dimethylammonium)ethyl 4-sulfophenyl carbonate salt.
Claim 34
Dependent Claim
13 words
The composition of claim 18 wherein the precursor is 2-(N-butyl-N,N-dimethylammonium)ethyl 4-sulfophenyl carbonate salt.
Claim 35
Dependent Claim
13 words
The composition of claim 18 wherein the precursor is 2-[4-(N,N,N-trimethylammonium)phenyl]ethyl 4-sulfophenyl carbonate salt.
Claim 36
Dependent Claim
13 words
The composition of claim 18 wherein the precursor is 3-(1,1-dimethylpiperidinium) 4-sulfophenyl carbonate salt.
Claim 37
Dependent Claim
13 words
The composition of claim 18 wherein the precursor is 4-(1,1-dimethylpiperidinium) 4-sulfophenyl carbonate salt.
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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) | 1991-06-14 | 1991-12-14 | 1992-06-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-06-14 | 1995-12-14 | 1996-06-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-06-14 | 1999-12-14 | 2000-06-14 | $7700.00 | Window Closed / Lapsed |