EP0185522A2
Expired / Lapsed
EP
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Phenylene mixed diester peracid precursors
Assignee: Clorox Co
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Filing: 1985-12-12
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Granted: —
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Expires: 2005-12-12
Abstract
Abstract The invention provides novel peracid precursors representative of which is the structure: wherein R' is alkyl of 1 to 20 carbon atoms; R 2 is OH, -O-R 3 , and X', X2, Y and Z are individually selected from H, S03, CO 2 , NO 2 , NR 5+ 4 ; halogen, R 6 and mixtures thereof: wherein R 3 of -O-R 3 is alkyl of 1 to 20 carbon atoms: R 4 is alkyl of 1 to 20 carbon atoms: R 5 of NR 5+ 4 is selected from H, alkyl of 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of 1 to 20 carbon atoms. In one embodiment of the invention, the novel peracid precursors are combined with a source of hydrogen peroxide and sufficient quantities of buffer to impart an alkaline pH when the composition is placed in aqueous solution. Preferred embodiments of the invention include wherein R 2 is hydroxy, and R' is alkyl of 1 to 20 carbon atoms (monoester); and wherein R 2 is and R 1 and R 4 are alkyls of 1 to 20 carbon atoms (diester) and may be either symmetrical (i.e., R 1 =R 4 ) or mixed (i.e., R 1 ≠R 4 ). The mixed diester embodiment appears to provide benefits of mixed hydrophobic-hydrophilic peracid generation to oxidize both hydrophobic and hydrophilic soils. Various detergent adjuncts known to those skilled in the art may be added, such as surfactants, builders, fragrances, antimicrobial compounds and the like.
Inventors
- 👤 Ronald Augustus Fong
- 👤 Stephen Bradford Kong
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-31 10:13
CPC Classifications
C; C11; C11D; C11D3/00; C11D3/39; C11D3/3902; C11D3/3905; C11D3/3907
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
165 words
A compound of the general structure: wherein R 1 is alkyl of about 1 to 20 carbon atoms: R 2 is OH, -O-R 3 , or and X 1 , X 2 , Y and Z are individually selected from H, SO - 3 , CO - 2 , NO 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -O-R 3 is alkyl of about 1 to 20 carbon atoms; R 4 of is alkyl of about 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of about 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of about 1 to 20 carbon atoms; wherein when R 2 is OH , R 1 has more than about 3 carbon atoms; and when R 2 is and R 1 and R 4 comprise individually alkyls of less than about 3 carbon atoms, R 1 ≠ R 4 .
Claim 2
Dependent Claim
165 words
A compound of the general structure: wherein R 1 is alkyl of about 1 to 20 carbon atoms: R 2 is OH, -O-R 3 , or and X 1 , X 2 , Y and Z are individually selected from H, SO - 3 , CO - 2 , NO 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -O-R 3 is alkyl of about 1 to 20 carbon atoms; R 4 of is alkyl of about 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of about 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of about 1 to 20 carbon atoms; wherein when R 2 is OH , R 1 has more than about 3 carbon atoms; and when R 2 is and R 1 and R 4 comprise individually alkyls of less than about 3 carbon atoms, R 1 ≠ R 4 .
Claim 3
Dependent Claim
25 words
The compound of claim 1 wherein R 1 is a straight chain alkyl of about 1 to 11 carbon atoms and R 2 is OH.
Claim 4
Dependent Claim
62 words
The compound of claim 1 wherein R 1 is a straight chain alkyl of about 1 to 11 carbon atoms and R 2 is wherein R 4 is a straight chain alkyl of about 1 to 11 carbon atoms, and when R 1 and R 4 individually comprise alkyls of less than about 3 carbon atoms, R 1 ≠ R 4 .
Claim 5
Dependent Claim
25 words
The compound of claim 3 wherein R is less than 5 carbon atoms in length and R 4 is greater than 5 carbons in length.
Claim 6
Dependent Claim
30 words
The compound of claim 2 wherein said compound has the structure R 1 being a straight chain alkyl of about 4 to 11 carbon atoms, and R 2 being OH.
Claim 7
Dependent Claim
38 words
The compound of claim 2 wherein at least one of X 1 , X 2 , Y and Z is halogen selected from the group consisting essentially of Cl , F - , Br and I - ,
Claim 8
Dependent Claim
43 words
The compound of claim 2 or claim 3 wherein at least one of X , X 2 , Y and Z are SO 3 with a counterpart ion which is H + or an alkali metal cation selected from sodium, potassium or lithium.
Claim 9
Dependent Claim
55 words
The compound of claim 3 wherein said compound has the structure wherein R 2 is and R 1 and R 4 individually comprise straight chain alkyls of about 1 to 11 carbon atoms and when R 1 and R 4 individually comprise alkyls or less than about 3 carbon atoms, R 1 ≠R 4 .
Claim 10
Dependent Claim
19 words
The compound of claim 4 or claim 7 wherein and R 2 are para in relationship to each other.
Claim 11
Dependent Claim
19 words
The compound of claim 4 or claim 7 wherein and R 2 are ortho in relationship to each other.
Claim 12
Dependent Claim
19 words
The compound of claim 4 or claim 7 wherein and R 2 are meta in relationship to each other.
Claim 13
Dependent Claim
157 words
A bleaching composition comprising: (a) a source of hydrogen peroxide; and (b) a bleach effective amount of a peracid precursor which is a compound according to any one of claims 1 to 11, or any other compound of the general structure: wherein R 1 is alkyl of 1 to 20 carbon atoms; R 2 is OH, -O-R 3 , or and X 1 , X 2 , Y and Z are indivi- dually selected from H, SO - 3 , CO - 2 , N0 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -n-R 3 is alkyl of about 1 to 20 carbon atoms; R 4 of is alkyl of about 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of about 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of about 1 to 20 carbon atoms.
Claim 14
Dependent Claim
25 words
The composition of claim 12 further comprising (c) sufficient quantities of buffer to yield an alkaline pH when the composition is placed in aqueous solution.
Claim 15
Dependent Claim
22 words
The composition of any one of claims 12 to 13 further comprising (d) a surfactant which will not react with the precursor.
Claim 16
Dependent Claim
25 words
The composition of claim 14 wherein the surfactant is selected from the group consisting essentially of anionic, nonionic, zwitterionic, cationic, amphoteric surfactants and mixtures thereof.
Claim 17
Dependent Claim
12 words
The composition of claim 15 wherein the surfactant is a nionic surfactant.
Claim 18
Dependent Claim
32 words
The composition of any one of claims 12 to 16 wherein the hydrogen peroxide source is selected from the alkali metal salts of percarbonate, perborate, persilicate, hydrogen peroxide adducts and hydrogen peroxide.
Claim 19
Dependent Claim
23 words
The composition of claim 17 wherein the hydrogen peroxide source is selected from sodium perborate monohydrate or tetrahydrate, sodium percarbonate and hydrogen peroxide.
Claim 20
Dependent Claim
34 words
The composition of claim 17 or claim 18 wherein the ratio of hydrogen peroxide yielded by the hydrogen peroxide source to the precursor is greater than about 1:1 of hydrogen peroxide to ester equivalent.
Claim 21
Dependent Claim
38 words
The composition of claim 12 wherein in at least one of the ester substituents and or alkyl substituent R 6 , R 1 , R 4 or R 6 is substituted alkyl of 1 to 20 carbon atoms.
Claim 22
Dependent Claim
31 words
The composition of claim 20 wherein at least one of R 1 , R 4 or R 6 is substituted at the carbon adjacent the carbonyl group of the ester groups.
Claim 23
Independent Claim
163 words
A method of producing a bleaching composition comprising combining: (a) a source of hydrogen peroxide; and (b) a bleach effective amount of a peracid precursor which is a compound according to any one of claims 1 to 11 or any other compound of the general structure: wherein R 1 is alkyl of 1 to 20 carbon atoms; R 2 is O H , -O-R 3 , or and X 1 , X 2 , Y and Z are individually selected from H, SO - 3 , CO - 2 , NO 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -O-R 3 is alkvl of about 1 to 20 carbon atoms; R 4 of is alkyl of about 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of about 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of about 1 to 20 carbon atoms.
Claim 24
Independent Claim
195 words
A method for synthesizing the compound wherein R 1 is alkyl of about 1 to 20 carbon atoms; R 2 is OH, O - R 3 , or and X 1 , X 2 , Y and Z are individually selected from H, SO - 3 , CO - 2 , NO 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -O-R 3 is alkyl of about 1 to 20 carbon atoms; R 4 of is alkyl of about 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of about 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of about 1 to 20 carbon atoms. wherein when R 2 is OH, R 1 has more than about 3 carbon atoms; and wherein when R 2 is and R 1 and R 4 comprise individually alkyls of less than about 3 carbon atoms, R 1 ≠ R 4 , the method comprising: reacting a dihydroxybenzene selected from the group consisting essentially of hydroquinone, resorcinol and catechol with an approximately equimolar amount of C 3-20 carboxylic acid anhydride.
Claim 25
Independent Claim
195 words
A method for synthesizing the compound wherein R 1 is alkyl of about 1 to 20 carbon atoms; R 2 is OH, O - R 3 , or and X 1 , X 2 , Y and Z are individually selected from H, SO - 3 , CO - 2 , NO 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -O-R 3 is alkyl of about 1 to 20 carbon atoms; R 4 of is alkyl of about 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of about 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of about 1 to 20 carbon atoms. wherein when R 2 is OH, R 1 has more than about 3 carbon atoms; and wherein when R 2 is and R 1 and R 4 comprise individually alkyls of less than about 3 carbon atoms, R 1 ≠ R 4 , the method comprising: reacting a dihydroxybenzene selected from the group consisting essentially of hydroquinone, resorcinol and catechol with an approximately equimolar amount of C 3-20 carboxylic acid anhydride.
Claim 26
Dependent Claim
23 words
The method of claim 23 wherein said reacting step includes a base - catalyzed reaction containing a solubilizing amount of a non-nucleophilic solvent.
Claim 27
Dependent Claim
16 words
The method of claim 24 wherein the base in said base - catalyzed reaction is triethylamine.
Claim 28
Dependent Claim
18 words
The method of claim 24 wherein said reacting step includes a catalyst suitable to transfer an ester moiety.
Claim 29
Dependent Claim
10 words
The method of claim 26 wherein said catalyst is 4-dimethyl-aminopyridine.
Claim 30
Dependent Claim
13 words
The method of claim 23 wherein said reacting step includes an acid-catalyzed reaction.
Claim 31
Dependent Claim
19 words
The method of claim 28, wherein the acid in said acid-catalyzed reaction is methanesulfonic acid or concentrated sulfuric acid.
Claim 32
Dependent Claim
19 words
The method of claim 29 further comprising the step of: heating and stirring until the reaction is essentially completed.
Claim 33
Independent Claim
15 words
The method of any one of claims 23 to 30 wherein said dihydroxybenzene is monesterified.
Claim 34
Independent Claim
164 words
A method of removing soils from fabrics comprising contacting said fabrics with a bleaching composition which comprises: (a) a source of hydrogen peroxide; and (b) a bleach effective amount of a peracid precursor which is a compound according to any one of claims 1 to 11, or any other compound of the general structure wherein R is alkyl of 1 to 20 carbon atoms; R 2 is OH, -O-R 3 , or and X 1 , X 2 , Y and Z are individually selected from H, SO - 3 , CO - 2 , NO 2 , NR 5+ 4 , halogen, R 6 and mixtures thereof; wherein R 3 of -O-R 3 is alkyl of 1 to 20 carbon atoms; R 4 of is alkyl of 1 to 20 carbon atoms; R 5 of NR 5+ 4 is selected from H, alkyl of 1 to 24 carbon atoms and mixtures thereof; and R 6 is alkyl of 1 to 20 carbon atoms.
References Cited (Backward Citations)
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