Photochemical superoxide generators

Details Photochemical superoxide generators Photochemical superoxide generators

1999-07-23

2001-05-01

Hardee, John (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

For cleaning a specific substrate or removing a specific...

C540S128000, C540S140000

Reexamination Certificate

active

06225273

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to photochemical superoxide generators and their use in laundry compositions and hard surface cleaning compositions comprising one or more of said photochemical superoxide generators, effective as a bleaching agent, stain remover, or bactericide. The present invention also relates to methods for cleaning fabric or hard surfaces, and for providing a means of sanitizing fabric or hard surfaces.
BACKGROUND OF THE INVENTION
It is known that certain water-soluble phthalocyanine, naphthalocyanine, mixed cyanine, and metallocyanine compounds can be used as photobleaching and antimicrobial agents. Phthalocyanines and naphthalocyanines or their metal complexes can form “singlet oxygen” an oxidative species capable of reacting with stains to bleach them to a colorless and usually water-soluble state.
It has now been surprisingly found that certain porphyrin, metalloporphyrin, phthalocyanine, naphthalocyanine, mixed cyanine, and metallocyanine compounds can photochemically produce superoxide. Superoxide is typically formed via non-photochemical means from the disproportionation of alkali and alkaline earth metal superoxides.
Superoxide is a reactive oxygen species formed by the one electron reduction of oxygen, has a longer lifetime than singlet oxygen and is capable of decolorizing (bleaching) stains and killing bacteria. Throughout this application superoxide is represented as O
2
−
based on common literature practice.
Surprisingly, it has been found that superoxide can be efficiently produced by photochemical means. Certain photosensitizing units which comprise a moiety capable of transfering an electron to the photochemically excited &pgr; electron cloud of the photosensitizer unit, are capable of producing superoxide. Preferably the photosensitizers, preferably porphyrins, metalloporphyrins, cyanines, and metallocyanines, and have the electron transfering moiety covalently attached.
It is therefore an aspect of the present invention to provide novel materials that photochemically produce superoxide. These materials are photosensitizing units which have covalently attached a moiety capable of transfering an electron to the excited state of the aforementioned photosensitizer. The superoxide produced by these compounds is useful in that the superoxide molecules are capable of acting as bleaching materials or as antimicrobials.
It is a further aspect of the present invention to provide laundry detergent and hard surface cleaning compositions comprising the aforementioned superoxide generators.
In accordance with still another aspect of the present invention, a method for removing stains from fabric and for killing bacteria as well as preventing the re-propagation of said bacteria is herein provided. The method comprises contacting the fabrics or surface contaminated with bacteria with an aqueous medium comprising at least 0.001 ppm of the photochemical superoxide generators described herein below. These, and other objects, features, and advantages will be clear from the following detailed description and the appended claims.
BACKGROUND ART
The following references relate to various aspects of superoxide and photochemical processes encompassed within the present invention:
Chem. Rev
., Kavarnos G. J., Turro N. J., 86, pg. 401, (1986);
Angew. Chem. Int. Ed. Eng
., Mattay J., 26, pg. 825, (1987);
Adv. Phys. Org. Chem
., Eberson L., 18, pg. 79, (1987);
Top. Current Chem
., Lopez, L., 156, pg. 117 (1990);
Adv. Photochem
., Fox, M. S., 13, pg. 237, (1986); “Synthetic Organic Photochemistry”, Horspool W. M. (ed); Mariano, P. S., pg. 145, (1984), Plenum Press, New York; “Organic Photochemistry”, Padwa, A. (ed); Mattes, S. L. and Farid, S., 6, pg. 233, (1983);
Accounts of Chemical Research
, Parker, V. D., 17, pg. 243, (1984).
SUMMARY OF THE INVENTION
The present invention relates to photochemical superoxide generators having the formula:
wherein P is a photosensitizing group; each D is independently a unit having the formula:
—L
1
—E or —L
1
—B—[L
2
—E]
m
wherein B is a unit capable of providing a branch point; L
1
and L
2
are linking units; E units are electron transfer units having the formula:
 wherein each W
1
and W
2
is independently C
1
-C
4
alkylene; G is hydrogen, an electron withdrawing group, and mixtures thereof; m is from 2 to 4; provided:
a) L
1
, L
2
, and B taken alone or in combination do not form a continuous series of conjugated bonds extending from the photosensitizing group P to the moiety E; and
b) the number of chemical bonds from photosensitizing group P to the E unit are no more than 20; and R is an axial moiety which mediates the solubility or substantivity of the superoxide generator.
It is also an object of the present invention to provide laundry detergent compositions comprising the photochemical superoxide generators described herein and methods for using said super oxide generators for bleaching fabric. The laundry detergent compositions comprise:
a) at least about 0.1% by weight, of a detersive surfactant;
b) at least about 0.001% of a source of superoxide; and
c) the balance carriers and adjunct ingredients.
It is a further object of the present invention to provide a hard surface cleaning compositions and a method for sanitizing a hard surface by contacting the superoxide generators described herein with a surface in need of cleaning or disinfecting.
It is yet a further object of the present invention to provide a method for bleaching fabric having stains or soils, or otherwise in need of bleaching, by contacting an aqueous solution of the photochemical superoxide generators of the present invention with said fabric.
All percentages, ratios and proportions herein are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C.) unless otherwise specified. All documents cited are in relevant part, incorporated herein by reference.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to superoxide generators wherein the superoxide is induced by a photochemical means, that is superoxide is produced when the superoxide generator is exposed to a source of light. The resulting superoxide molecule which is generated therein has the capacity to act as an effective bleaching agent, disinfectant or bactericide.
The superoxide generators of the present invention have the formula:
and comprise:
a) a photosensitizing group;
b) optionally a photoactive metal or non-metal;
c) at least one moiety which is capable of transferring an electron to the excited state of the photosensitizing group; and
d) optionally an axial moiety which mediates the solubility or substantivity of the superoxide generator molecule.
For the purposes of the present invention substituted aryl units are defined as moieties having the formula:
wherein R
13
and R
14
are independently selected from the group consisting of hydrogen, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
1
-C
6
alkoxy, C
3
-C
6
branched alkoxy, halogen, morpholino, cyano, nitrilo, —CO
2
−
M
+
, —SO
3
−
M
+
, —OSO
3
−
M
+
, —N(R
15
)
2
, and —N
+
(R
15
)
3
X
−
wherein each R
15
is independently hydrogen or C
1
-C
4
alkyl; and mixtures thereof; wherein M is a water soluble cation and X is chlorine, bromine, iodine, or other water soluble anion. Examples of other water soluble anions include organic species such as fumarate, tartrate, oxalate and the like, inorganic species include sulfate, hydrogen sulfate, phosphate and the like.
For the purposes of the present invention substituted alkylenearyl units are defined as moieties having the formula:
wherein R
13
and R
14
are the same as define above, p is from 1 to about 10.
For the purposes of the present invention substituted aryloxy units are defined as moieties having the formula:
wherein R
13
and R
14
are the same as define above.
For the purposes of the present invention substituted alkyleneoxyaryl units are defined as moieties having the formula:
wherein R
13
and R
14
are the same as define above, q is fr

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