Singlet oxygen generators having enhanced heavy atom effect

Details Singlet oxygen generators having enhanced heavy atom effect Singlet oxygen generators having enhanced heavy atom effect

1999-07-23

2001-05-15

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...

C510S367000, C540S122000, C540S128000, C540S140000

Reexamination Certificate

active

06232281

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to photochemical singlet oxygen generators having an enhanced level of activity useful as photobleaches and as photo disinfectants. The compounds of the present invention achieve the enhanced photochemical activity by the interaction of the “heavy atom-containing” axial substituents with the photosensitizing ring.
BACKGROUND OF THE INVENTION
It is known that certain water-soluble phthalocyanine, naphthalocyanine, and metallocyanine compounds can be used as photobleaching and anti-microbial 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.
There are many examples of phthalocyanines and naphthalocyanines photobleaches, the most common being the zinc and aluminum phthalocyanines. In the literature the term “photosensitizer” is often used instead of “photoactivator” and may therefore be considered as standing equally well for the latter term used throughout this specification.
The prior art teaches phthalocyanine and naphthalocyanine compounds having the general structure
where Me is a transition or non-transition metal, (Sens.) is a phthalocyanine or naphthalocyanine ring which, when combined with a suitable Me unit, is capable of undergoing photosensitization of oxygen molecules, R units are substituent groups which are bonded to the photosensitization ring units (Sens.) to enhance the solubility or photochemical properties of the molecule, and Y units are substituents associated with the metal atom, for example, anions to provide electronic neutrality. The selection of a particular substituent R unit for substitution into the molecule has been the focus of many years of research and these units are typically chosen by the formulator to impart into the target molecule the desired level of water solubility.
It has been a task of formulators of photobleaches to modify the properties of the (Sens.) unit of the molecule to increase the quantum efficiency without reducing the water solubility. While balancing water solubility and enhanced photophysics, the formulator must insure that the structural modifications do not increase the color.
Surprisingly, it has been found that the compounds of the present invention allow the formulators to increase the photoefficiency of the photoactive compounds without adversely affecting the other parameters of the molecule. This ability to delineate and selectively modify the key structural elements contributing to the target properties of the molecule allows the formulator to proceed without having to rely upon a “hit and miss” stratagem.
The photobleaches of the invention comprise a photosensitizing ring which chelates a photoactive metal or non-metal. To this photoactive metal or non-metal is attached a photo activating ligand which enhances the photoefficiency of the molecule via the “heavy atom effect”. In addition to the photoactivating ligand, the photobleaches of the present invention also comprise an axial group which mediates solubility and substantivity of the molecule.
It is therefore an object of the present invention to provide photochemical singlet oxygen generators which serve as photobleaches and photodisinfectants. It is a further object of the present invention to provide photobleaching compositions suitable for use as laundry detergent bleaching compositions.
It is a yet further object of the present invention to provide enhanced photobleaching hard surface cleaning compositions for non-porous hard surfaces, inter alia, Formica®, ceramic tile, glass, or for porous hard surfaces such as concrete or wood.
It is a still further object of the present invention is to provide a method for bleaching fabric with laundry compositions comprising the photobleaching compounds of the present invention.
It is yet still a further object of the present invention is to provide a method for cleaning hard surfaces with the photobleaching compounds of the present invention.
BACKGROUND ART
The following references relate to various aspects of 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 singlet oxygen generators having the formula:
wherein P is a photosensitizing unit; each D is independently a unit having the formula:
—L
1
—R
wherein L
1
is C
1
-C
20
linear or branched alkylene, C
1
-C
20
linear or branched alkenylene, C
6
-C
20
substituted or unsubstituted arylene, C
6
-C
20
substituted or unsubstituted aryleneoxy, C
7
-C
30
linear or branched alkylenearylene; provided L
1
is substituted within 10 covalent bonds of the photosensitizing unit by at least one heavy atom, said heavy atom selected from the group consisting of chlorine, bromine, iodine, and mixtures thereof; and optionally R is an axial moiety which mediates the solubility or substantivity of the singlet oxygen generator.
The present invention also relates to laundry detergent and hard surface cleaning compositions which comprise at least about 0.01% of the photoactive singlet oxygen generators of the present invention.
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 photochemical singlet oxygen generators useful for photochemical bleaching, photochemical disinfecting, and photochemical purification of fabric or hard surfaces. The photochemical singlet oxygen generators described herein produce singlet oxygen molecules at an enhanced efficiency due to the interaction of certain “heavy atoms” with the &pgr; electron cloud of the photosensitizer unit. The axial group which contains the “heavy atoms” also serves to tether these atoms in a manner which allows for efficient interaction between heavy atom and photosensitizer unit. In addition the tether is optionally linked to a group capable of mediating the solubility or substantivity of the molecule as a whole.
The singlet oxygen generators of the present invention have the formula:
and comprise:
a) a photosensitizing group;
b) a photoactive metal or non-metal chelated by said photosensitizing group;
c) at least one photochemical mediating axial moiety bonded to said photoactive metal or non-metal, said photochemical mediating axial moiety comprises at least one heavy atom within ten covalent bonds of the point of attachment of said photochemical mediating axial moiety to said photoactive metal or non-metal, said heavy atom selected from the group consisting of chlorine, bromine, iodine, and mixtures thereof; and
d) one or more axial moieties which mediate the solubility or substantivity of the singlet oxygen generator molecule, said solubility or substantivity mediating axial moiety is bonded directly to said photoactive metal or non-metal, or to the photochemical mediating axial moiety at the end distal to the photosensitizing group.
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
&

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