Glyoxylic compound comprising one or more active ingredient

Details Glyoxylic compound comprising one or more active ingredient Glyoxylic compound comprising one or more active ingredient

2001-02-08

2003-05-06

Short, Patricia A. (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S473000, C560S180000, C560S182000, C562S583000

Reexamination Certificate

active

06559243

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to glyoxylic compounds comprising one or more active ingredient, in particular alcohol or mixed alcohol/aldehyde ingredients. More particularly, it relates to glyoxylic compound comprising one or more active ingredient for use in laundry and cleaning products.
BACKGROUND OF THE INVENTION
Cleaning and laundry products are well-known in the art. However, consumer acceptance of laundry and cleaning products is determined not only by the performance achieved with these products but also the aesthetics associated therewith. The perfume components are therefore an important aspect of the successful formulation of such commercial products.
It is also desired by consumers for laundered fabrics to maintain the pleasing fragrance over time. Indeed, perfume additives make laundry compositions more aesthetically pleasing to the consumer, and in some cases the perfume imparts a pleasant fragrance to fabrics treated therewith. However, the amount of perfume carry-over from an aqueous laundry bath onto fabrics is often marginal and does not last long on the fabric. Furthermore, fragrance materials are often very costly and their inefficient use in laundry and cleaning compositions and ineffective delivery to fabrics result in a very high cost to both consumers and laundry and cleaning manufacturers. Industry, therefore, continues to seek with urgency for more efficient and effective fragrance delivery in laundry and cleaning products, especially for improvement in the provision of long-lasting fragrance to the fabrics.
One solution is to use carrier mechanisms for perfume delivery, such as by encapsulation. This is taught in the prior art and described in U.S. Pat. No. 5,188,753. Still another solution is to formulate compounds which provide a delayed release of the perfume over a longer period of time than by the use of the perfume itself have been provided. Disclosure of such compounds may be found in WO 95/04809, WO 95/08976 and pending application EP 95303762.9.
However, notwithstanding the advances in the art, there is still a need for a compound which provides a delayed release of the perfume component.
The Applicant has now found that glyoxylic compounds comprising one or more active alcohols also provide a delayed release of the active such as a perfume.
Another advantage of the invention is that these glyoxylic compound can suitably be copolymerised with a monomeric unit, of which an active aldehydic monomeric unit can suitably be used including those useful in perfumery. When active aldehyde monomeric unit are used, this results in a glyoxylic compound comprising mixed active alcohol/aldehyde group, which in turn results in the release of their respective group, i.e. active alcohol group and active aldehyde group.
Still another advantage of the present invention is that the glyoxylic compound comprising one or more of these active ingredients, i.e. active alcohols or mixed active alcohol/aldehyde provides sufficient stabilisation of the linkage bond between the active alcohol and/or aldehyde group with its carrier so that the release of the active ingredients upon storage in product is limited, without hindering the release of the active ingredients upon use of the product.
Still another advantage of the invention compounds is their ease of manufacture rendering their use most desirable.
SUMMARY OF THE INVENTION
The present invention relates to a glyoxylic compound comprising one or more active ingredient, wherein said compound has the following empirical formula:
wherein at least one of R or R2 is an organic chain of an active alcohol and the other (R and/or R2) is selected from hydrogen, alkali metals, ammonium, alkyl, alkenyl, aryl, alkylaryl, organic chain of an active alcohol, or any other chain containing at least 1 carbon atom, and
wherein each of R1, R′1 are each independently selected from hydrogen, hydroxyl, alkyl, alkenyl, aryl, alkylaryl, COOR3, (CR
4
R
4
)
q
COOR3, OR3, or any other chain containing at least 1 carbon atom;
wherein R3 is selected from hydrogen, alkali metals, ammonium, alkyl, alkenyl, aryl, alkylaryl, organic chain of an active alcohol, or any other chain containing at least 1 carbon atom,
wherein R4 are each independently selected from hydrogen, hydroxyl, alkyl, alkenyl, aryl, alkylaryl, COOR3, CH
2
COOR3, OR3, or any other chain containing at least 1 carbon atom;
wherein Y is a comonomeric unit,
wherein m is an integer of value from 0 to 10000, preferably from 0 to 1000 and more preferably between 0 and 100, and
wherein n is an integer of value of at least 1, preferably less than 1000 and more preferably less than 100;
wherein q is an integer of value from 0 to 10, preferably from 0 to 4 and more preferably 0.
In another aspect of the invention, there is provided a laundry and cleaning composition or personal cleansing composition comprising said compound.
Still another aspect of the invention is a method of delivering residual fragrance to a surface which comprises the steps of contacting said surface with a compound of the invention or a composition comprising said compound in presence of material so that at least one of the oxygen bearing perfume is hydrolysed.
Detailed Description of the Invention
The essential component of the invention is a compound derived from glyoxylic acid. The compound of the invention has the following empirical formula:
wherein at least one of R or R2 is an organic chain of an active alcohol and the other (R and/or R2) is selected from hydrogen, alkali metals, ammonium, alkyl, alkenyl, aryl, alkylaryl, organic chain of an active alcohol, or any other chain containing at least 1 carbon atom, and
wherein each of R1, R′1 are each independently selected from hydrogen, hydroxyl, alkyl, alkenyl, aryl, alkylaryl, COOR3, (CR
4
R
4
)
q
COOR3, OR3, or any other chain containing at least 1 carbon atom;
wherein R3 is selected from hydrogen alkali metals, ammonium, alkyl, alkylene, aryl, alkylaryl, organic chain of an active alcohol, or any other chain containing at least 1 carbon atom,
wherein R4 are each independently selected from hydrogen, hydroxyl, alkyl, alkenyl, aryl, alkylaryl, COOR3, CH
2
COOR3, OR3, or any other chain containing at least 1 carbon atom;
wherein Y is a comonomeric unit,
wherein m is an integer of value from 0 to 10000, preferably from 0 to 1000 and more preferably between 0 and 100, and
wherein n is an integer of value of at least 1, preferably less than 1000 and more preferably less than 100;
wherein q is an integer of value from 0 to 10, preferably from 0 to 4 and more preferably 0.
By alkyl and alkenyl chain, it is understood a chain length of at least 1 carbon, preferably 1 to 20 carbon atoms, and more preferably is methyl or ethyl. Of course, it is also understood that the chain and cycles can be optionally substituted or interrupted. Typical of such substitution is a short alkyl chain such as methyl, ethyl, or hydroxy group. Typical of such interruption is with an O, N, CO, OC(O), CO(O), C(O)N, NC(O) and mixtures thereof.
By “co-monomeric unit”, it is meant any suitable comonomer which can be copolymerised with the glyoxylic monomeric unit. Typical of such comonomers are those having at least two reactive sites and which do not inhibit the polymerisation or cause the copolymer to depolymerise in alkaline solution. Preferably, these monomeric units are selected from epoxy compounds such as ethylene oxide, propylene oxide, epihalohydrin epoxysuccinate and the like; aldehydes such as formaldehyde, acetaldehyde, active aldehyde such as those commonly used in perfumery including octanal, decanal, dodecanal, methylnonyl acetaldehyde, benzaldehyde as well as aldehydes containing up to 20 carbon atoms. Preferred among the one above disclosed are the active aldehyde commonly used in perfumery which then result in the release of either a mixed active alcohol compound and an aldehydic perfume compound or even most preferred a mixed perfume fragrance of alcohol(s) and aldehyde(s).
For ease of purpose, the copolymer has been schematised under its emp

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