Polymeric compound comprising one or more active alcohols

Details Polymeric compound comprising one or more active alcohols Polymeric compound comprising one or more active alcohols

1999-09-01

2001-02-06

Hardee, John (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

Specific organic component

Reexamination Certificate

active

06184197

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to polymeric compounds comprising one or more active alcohols. More particularly, it relates to amino functional polymeric compounds comprising one or more active alcohols suitable 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 cleaning and laundry 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.
Accordingly, formulation of 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. The latter describes betaine ester compounds of perfume alcohols which provide release of the perfume components over a long period of time.
The Applicant has now found that polymers containing one or more nitrogen atoms to which an ester function is linked, so as to provide an N-polymeric betaine ester and/or amino ester of an active alcohol, also provide a delayed release of the active alcohol such as a perfume.
Another advantage of the present invention is that the polymeric group provides sufficient stabilisation of the ester function so that the release of the active alcohol upon storage in product is limited, without hindering the release of the active alcohol upon use of the product.
SUMMARY OF THE INVENTION
The present invention relates to a polymer containing at least one nitrogen atoms, wherein at least one of the nitrogen atoms is linked to an ester group of formula:
wherein each R′
1
, R′
2
, independently, is selected from hydrogen, hydroxyl, alkyl group, alkylene group, aryl group, alkylaryl, or any other chain containing at least 1 carbon atom, wherein n
3
is an integer lying in the range from 1 to 3, and wherein R is an organic chain of an active alcohol.
The present invention also encompasses laundry and cleaning compositions incorporating said polymeric compound.
In another aspect of the invention, there is provided a method for providing a delayed release of an active alcohol which comprises the step of contacting materials to be treated with an aqueous medium comprising a compound or composition of the invention.
In a further aspect of the invention, a process is provided for preparing a polymeric ester compound of the invention, by reacting a polyaminofunctional polymer with a bromoacetate and/or chloroacetate of an active alcohol in the presence of a non hydroxylated solvent.
DETAILED DESCRIPTION OF THE INVENTION
Polymeric Compound
The essential component of the invention is a polymer containing at least one nitrogen atom, wherein at least one of the nitrogen atoms is linked to an ester group of formula:
wherein each R′
1
, R′
2
, independently, is selected from hydrogen, hydroxyl, alkyl group, alkylene group, aryl group, alkylaryl group, or any other chain containing at least 1 carbon atom, wherein n
3
is an integer lying in the range from 1 to 3, preferably n
3
is an integer of value 1, and wherein R is an organic chain of an active alcohol.
The different groups for R′
1
, R′
2
can be substituted or unsubstituted.
Preferably, each R′
1
, R′
2
, independently, is selected from hydrogen, alkyl group, aryl group, —(CH
2
)
m
—COOH, —(CH
2
)
m
—COOR, —(CH
2
)
m
,—OH, —(CH
2
)
m
,—O(O)CR′ wherein each m, independently, is an integer of value 0, 1 or 2, and each m′, independently, is an integer of value 1, 2 or 3, and R′ is an alkyl group containing from 1 to 19 carbons. More preferably, each R′
1
, R′
2
is independently, selected from hydrogen, methyl group, aryl group and most preferably is hydrogen.
Polymers suitable for use herein generally have a molecular weight of less than 100,000, preferably comprised between 300 and 100,000, more preferably between 500 and 10,000, and most preferably between 500 to 5,000. The polymer can be of any type, including copolymer, homopolymers, terpolymer or mixtures of any monomer as long as at least one nitrogen atom is present within the polymer. The nitrogen atom bearing the ester function containing the active alcohol can be located in any position, i.e. in the backbone and/or side chain.
Preferred polymers suitable for use herein are the amino-functional polymers selected from polyamines, polyvinylpyridines, copolymers of poly (vinylpyrrolidone/vinylimidazole), polymers having pyrolidine rings, polyvinylimidazoles, chitosans, and mixtures thereof, preferably polyamine polymers. The polymer may be linear or branched but is preferably branched.
Polyamine polymers suitable for use herein are selected from
a)-linear or non-cyclic polyamines having a backbone of the formula:
b)-cyclic polyamines having a backbone of the formula:
c)-polyamines having a backbone of the formula:
 and mixtures thereof;
wherein R′ is C
2
-C
8
alkylene, C
3
-C
8
alkyl substituted alkylene, and mixtures thereof; preferably R′ is ethylene, 1,2-propylene, 1,3-propylene, and mixtures thereof, more preferably ethylene. R′ units serve to connect the amine nitrogens of the backbone; wherein m is from 2 to 700; n is from 0 to 350; y is from 5 to 10,000, preferably from 10 to 5,000, more preferably from 20 to 5,000.
Preferably, the polyamines have a ratio of m:n of at least 1:1 but may include linear polymers (n equal to 0) as well as a range as high as 10:1, preferably the ratio is 2:1. When the ratio of m:n is 2:1, the ratio of primary:secondary:tertiary amine moieties, that is the ratio of —R′NH
2
, —R′NH, and —R′N moieties, is 1:2:1.
The preferred polyamines for use herein comprise backbones wherein less than 50% of the R′ groups comprise more than 3 carbon atoms; more preferably comprise less than 25% moieties having more than 3 carbon atoms, most preferred backbones comprise less than 10% moieties having more than 3 carbon atoms.
The polyamines for use herein comprise homogeneous or non-homogeneous polyamine backbones, preferably homogeneous backbones. For the purpose of the present invention the term “homogeneous polyamine backbone” is defined as a polyamine backbone having R′ units that are the same (i.e., all ethylene). However, this sameness definition does not exclude polyamines that comprise other extraneous units comprising the polymer backbone that are present due to an artifact of the chosen method of chemical synthesis. For example, it is known to those skilled in the art that ethanolamine may be used as an “initiator” in the synthesis of polyethyleneimines; therefore, a sample of polyethyleneimine that comprises one hydroxyethyl moiety resulting from the polymerization “initiator” would be considered to comprise a homogeneous polyamine backbone for the purposes of the present invention.
For the purposes of the present invention the term “non-homogeneous polymer backbone” refers to polyamine backbones that are a composite of one or more alkylene or substituted alkylene moieties, for example, ethylene and 1,2-propylene units taken together as R′ units.
Other polyamines that comprise the above mentioned backbone are generally polyalkyleneamines (PAA's), polyalkyleneimines (PAl's), preferably polyethyleneamine (PEA's), or polyethyleneimines (PEI's). A common polyalkyleneamine (PAA) is tetrabutylenepentamine. PEA's are obtained by reactions involving ammonia and ethylene dichloride, followed by fractional distillation. The common PEA's obtained are triethylenetetramine (TETA) and tetraethylenepentamine (TEPA). Above the pentamines, i.e., the hexamines, heptamines, octamines and possibly nonamines, the cogenerically derived mixture does not appear to separate by distillation and can include other materials such as cyclic amines and particularly pip

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