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Patent 2225016 Summary

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(12) Patent Application: (11) CA 2225016
(54) English Title: METHOD FOR INCREASING THE EFFICACY OF AN ODOR MASKING AGENT
(54) French Title: PROCEDE POUR AUGMENTER L'EFFICACITE D'UN AGENT DEODORANT
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • A01N 31/08 (2006.01)
  • A01N 25/30 (2006.01)
  • A01N 31/12 (2006.01)
  • A01N 33/12 (2006.01)
  • A01N 37/40 (2006.01)
  • A01N 43/42 (2006.01)
  • C11D 1/66 (2006.01)
  • C11D 1/83 (2006.01)
  • C11D 3/48 (2006.01)
  • C11D 1/29 (2006.01)
(72) Inventors :
  • LAZAROWITZ, VIRGINIA L. (United States of America)
  • DEMAIO, CHRISTINE (United States of America)
  • GESSLEIN, BRUCE W. (United States of America)
(73) Owners :
  • HENKEL CORPORATION (United States of America)
(71) Applicants :
  • HENKEL CORPORATION (United States of America)
(74) Agent: SWABEY OGILVY RENAULT
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1996-06-17
(87) Open to Public Inspection: 1997-01-09
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US1996/009244
(87) International Publication Number: WO1997/000609
(85) National Entry: 1997-12-18

(30) Application Priority Data:
Application No. Country/Territory Date
60/000,380 United States of America 1995-06-21
08/660,589 United States of America 1996-06-11

Abstracts

English Abstract




The efficacy of an odor masking or odor repressing agent in an aqueous
cleaning composition containing a disinfectant such as a bactericide can be
improved by incorporating a nonionic sugar surfactant into an aqueous
composition which contains a compound having anti-bacterial activity and an
odor-masking agent.


French Abstract

L'efficacité d'un agent qui supprime ou qui refoule les odeurs, dans un composé de nettoyage aqueux contenant un désinfectant tel qu'un bactéricide peut être améliorée par l'incorporation d'un tensio-actif de sucre non-ionique dans un composé aqueux qui contient un composé ayant une activité anti-bactérienne et un agent supprimant les odeurs.

Claims

Note: Claims are shown in the official language in which they were submitted.





16
What is claimed is:
1. A disinfectant cleaning composition comprising: (a) an amount of a
nonionic sugar surfactant sufficient to decrease the effective amount of an odormasking agent wherein said nonionic sugar surfactant is selected from the group
consisting of an alkyl glucose ester, an aldobionamide, a gluconamide. a
glyceramide, a glyceroglycolipid, a polyhydroxy fatty acid amide, an alkyl
polyglycoside, and combinations thereof: (b) a disinfecting effective amount of
an anti-bacterial compound selected from the group consisting of a halo-substituted
monohydric phenol, a halo-substituted dihydric phenol, a halo-substituted
trihydric phenol, a halo-substituted hydroxybenzoic acid, a halo-substituted
bis(hydroxyphenyl)alkane, lauryl dimethylbenzyl ammonium bromide,
alkyl trimethyl ammonium bromide, and an alkyl isoquinolinium bromide; (c) an
odor rnasking effective amount of an odor-modifying agent selected from the
group consisting of 3,5,5-trimethylhexanal, aromatic aldehydes. esters, alcohols,
and oxygenated monoterpenes, citral, .alpha.- and .beta.-ionone, natural citrus oils, and
mixtures thereof.

2. The composition of claim 1 wherein said anti-bacterial compound is
4-chloro-3,5-dimethylphenol.

3. The composition of claim 1 wherein said anti-bacterial compound is lauryl
benzyl dimethylammonium chloride.

4. The composition of claim 1 whorein said sugar surfactant is an alkyl
polyglycoside of the formula VII
R1O(R2O)b(Z)a VII
wherein R1 is a monovalent organic radical having from about 6 to about 30
carbon atoms; Z is a saccharide residue having 6 carbon atoms; b is 0; a is a
number having a value from 1 to about 6.


17

5. The composition of claim 4 wherein R1 is a monovalent organic radical
having from about 12 to about 16 carbon atoms and a is a number having a
value from 1 to about 2Ø

6. The composition of claim 4 wherein said odor masking agent is a mixture
of aromatic aldehydes, esters, alcohols, and oxygenated monoterpenes.

7. The composition of claim 4 wherein the weight ratio of alkyl
polyglycoside/odor masking agent is from about 45/1 to about 2/1.

8. A disinfectant cleaning composition comprising: (a) an solubilizing amount
of a mixture comprised of a first and a second alkyl polyglycoside wherein each
of said first and second alkyl polyglycosides has a different average carbon chain
length in the alkyl moiety; (b) a disinfecting effective amount of an anti-bacterial
compound selected from the group consisting of a halo-substituted monohydric
phenol, a halo-substituted dihydric phenol, a halo-substituted trihydric phenol, a
halo-substituted hydroxybenzoic acid, a halo-substituted
bis(hydroxyphenyl)alkane, lauryl dimethylbenzyl ammonium bromide, alkyl
trimethyl ammonium bromide, and an alkyl isoquinolinium bromide; (c) an odor
masking effective amount of an odor-modifying agent selected from the group
consisting of 3,5,5-trimethylhexanal, aromatic aldehydes, esters, alcohols, and
oxygenated monoterpenes, citral, .alpha.- and .beta.-ionone, natural citrus oils, and
mixtures thereof.

9. The composition of claim 8 wherein (a) is a mixture of a C8 and a C16 alkyl
polyglycoside.

10. The composition of claim 9 wherein the weight ratio of said C8 to said C16
alkyl polyglycoside is from about 30/70 to about 70/30.

11. The composition of claim 10 wherein the weight ratio of said C8 to said C16alkyl polyglycoside is from about 40/60 to about 60/40.




18
12. The composition of claim 8 wherein said anti-bacterial compound is
4-chloro-3,5-dimethylphenol.

13. The composition of claim 8 wherein said anti-bacterial compound is lauryl
benzyl dimethylammonium chloride.

14. A disinfectant cleaning composition comprising: (a) an amount of a
nonionic sugar surfactant sufficient to decrease the effective amount of an odormasking agent wherein said nonionic sugar surfactant is selected from the group
consisting of an alkyl glucose ester, an aldobionamide, a gluconamide, a
glyceramide, a glyceroglycolipid, a polyhydroxy fatty acid amide, an alkyl
polyglycoside, and combinations thereof: (b) a disinfecting effective amount of
an anti-bacterial compound selected from the group consisting of a
halo-substituted monohydric phenol, a halo-substituted dihydric phenol, a
halo-substituted trihydric phenol, a halo-substituted hydroxybenzoic acid, a
halo-substituted bis(hydroxyphenyl)alkane, lauryl dimethylbenzyl ammonium bromide,
alkyl trimethyl ammonium bromide, and an alkyl isoquinolinium bromide; (c) an
odor masking effective amount of an odor-modifying agent selected from the
group consisting of 3,5,5-trimethylhexanal, aromatic aldehydes, esters, alcohols,
and oxygenated monoterpenes, citral, .alpha.- and .beta.-ionone, natural citrus oils, and
mixtures thereof; (d) an anionic surfactant selected from the group consisting of
an alkyl sulfate, an alkyl ether sulfate, an alkyl sulfonate, an alkyl ether sulfonate,
a sulfosuccinate and mixtures thereof.

15. The composition of claim 14 wherein said anionic surfactant is an alkyl
ether sulfate.

16. The composition of claim 14 wherein said anti-bacterial compound is
4-chloro-3,5-dimethylphenol.

17. The composition of claim 14 wherein said anti-bacterial compound is lauryl
benzyl dimethylammonium chloride.

19
18. The composition of claim 14 wherein said sugar surfactant is an alkyl
polyglycoside of the formula VII
R1O(R2O)b(Z)a VII
wherein R1 is a monovalent organic radical having from about 6 to about 30
carbon atoms; Z is a saccharide residue having 6 carbon atoms; b is 0; a is a
number having a value from 1 to about 6.

19. The composition of claim 18 wherein R1 is a monovalent organic radical
having from about 12 to about 16 carbon atoms and a is a number having a
value from 1 to about 2Ø

20. The composition of claim 14 wherein said odor masking agent is a mixture
of aromatic aldehydes, esters, alcohols, and oxygenated monoterpenes.

21. The composition of claim 14 wherein the weight ratio of anionic
surfactant/antibacterial compound is from about 8/1 to about 17/1.

22. The composition of claim 21 wherein said ratio is from about 1/1 to about
3/1.

23. A process for increasing the efficacy of an odor masking or odor
repressing agent which comprises mixing (a) an amount of a nonionic sugar
surfactant sufficient to decrease the effective amount of an odor masking agent
wherein said nonionic sugar surfactant is selected from the group consisting of
an alkyl glucose ester, an aldobionamide, a gluconamide, a glyceramide, a
glyceroglycolipid, a polyhydroxy fatty acid amide, an alkyl polyglycoside, and
combinations thereof: (b) a disinfecting effective amount of an anti-bacterial
compound selected from the group consisting of a halo-substituted monohydric
phenol, a halo-substituted dihydric phenol, a halo-substituted trihydric phenol, a
halo-substituted hydroxybenzoic acid, a halo-substituted
bis(hydroxyphenyl)alkane, lauryl dimethylbenzyl ammonium bromide, alkyl
trimethyl ammonium bromide, and an alkyl isoquinolinium bromide; (c) an odor


masking effective amount of an odor-modifying agent selected from the group
consisting of 3,5,5-trimethylhexanal, aromatic aldehydes, esters, alcohols, and
oxygenated monoterpenes, citral, .alpha.- and .beta.-ionone, natural citrus oils, and
mixtures thereof.

24. The process of claim 23 wherein said anti-bacterial compound is
4-chloro-3,5-dimethylphenol.

25. The process of claim 23 wherein said anti-bacterial compound is lauryl
benzyl dimethylammonium chloride.

26. The process of claim 23 wherein said sugar surfactant is an alkyl
polyglycoside of the formula VII
R1O(R2O)b(Z)a VII
wherein R1 is a monovalent organic radical having from about 6 to about 30
carbon atoms; Z is a saccharide residue having 6 carbon atoms; b is 0; a is a
number having a value from 1 to about 6.

27. The composition of claim 26 herein R1 is a monovalent organic radical
having from about 12 to about 16 carbon atoms and a is a number having a
value from 1 to about 2Ø

28. The process of claim 23 wherein said odor masking agent is a mixture of
aromatic aldehydes, esters, alcohols, and oxygenated monoterpenes.

29. The process of claim 23 wherein the weight ratio of alkyl
polyglycoside/odor masking agent is from about 45/1 to about 2/1.

30. A process for making a disinfectant cleaning composition having an
elevated amount of a disinfectant comprising mixing (a) a solubilizing amount ofa mixture comprised of a first and a second alkyl polyglycoside wherein each of
said first and second alkyl polyglycosides has a different average carbon chain


21

length in the alkyl moiety or an anionic surfactant selected from the group
consisting of an alkyl sulfate, an alkyl ether sulfate, an alkyl sulfonate, an alkyl
ether sulfonate, a sulfosuccinate or mixtures thereof with (b) an amount of a
nonionic sugar surfactant sufficient to decrease the effective amount of an odormasking agent wherein said nonionic sugar surfactant is selected from the group
consisting of an alkyl glucose ester, an aldobionamide, a gluconamide, a
glyceramide, a glyceroglycolipid, a polyhydroxy fatty acid amide, an alkyl
polyglycoside, and combinations thereof; (c) a disinfecting effective amount of
an anti-bacterial compound selected from the group consisting of a halo-substituted
monohydric phenol, a halo-substituted dihydric phenol, a halo-substituted
trihydric phenol, a halo-substituted hydroxybenzoic acid, a halo-substituted
bis(hydroxyphenyl)alkane, lauryl dimethylbenzyl ammonium bromide,
alkyl trimethyl ammonium bromide, and an alkyl isoquinolinium bromide; (d) an
odor masking effective amount of an odor-modifying agent selected from the
group consisting of 3,5,5-trimethylhexanal, aromatic aidehydes, esters, alcohols,
and oxygenated monoterpenes, citral, .alpha.- and .beta.-ionone, natural citrus oils, and
mixtures thereof.

31. The process of claim 30 wherein said anti-bacterial compound is
4-chloro-3,5-dimethylphenol.

32. The process of claim 30 wherein said anti-bacterial compound is lauryl
benzyl dimethylammonium chloride.

33. The process of claim 30 wherein said first and second alkyl
polyglycosides are C8 and a C16 alkyl polyglycoside.

34. The process of claim 33 wherein the weight ratio of said C8 to said C16
alkyl polyglycoside is from about 30/70 to about 70/30.

35. The process of claim 34 wherein the weight ratio of said C8 to said C16
alkyl polyglycoside is from about 40/60 to about 60/40.

Description

Note: Descriptions are shown in the official language in which they were submitted.


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METHOD FOR ~NCREASING THE EFFICACY OF
AN OIDOR MASKING AGENT
BENEFIT OF EARLIER FILING DATE UNDER 37 CFR 1.78(A)(4)
This application claims the benefit of earlier filed and copending
provisional application serial number 60/000,380 filed on June 21, 1995.
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates l:o compositions and methods which reduce the
unpleasant odor of cleaning cornpositions conl~i"i, Ig disinfectants. The invention
further relates to odor masking compositions for disinfectant cleaning
compositions, to a method of increasing the efficacy of an odor masking or odor
repressing agent, and to the use of odor-masked disinféctant compositions in
disinfectant cleaning composil:ions.
2. Background Art
Cleaning compositions such as personal cleansing preparations, hand and
machine dishwashing detergents, hard surface cleaners, and liquid and solid
~ 15 laundry detergents which contain disinfectants such as bactericides or
bacteriostats are becoming more widespread.

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Phenol derivatives are a common class of disinfectants used in cleaning
compositions. See e.g. "Disinfectants and Antiseptics", Encyclopedia of ChemicalTechnology. vol. 7, pp. 808-815 (Kirk-Othmer, eds., John Wiley & Sons, Inc.
N.Y., N.Y., 3d ed. 1979). As this article states, phenol itself is of mostly historical
interest or as a research tool in microbiology. The disinfectant art progressed to
homologues of phenol, halogenated phenols, halogenated homologues, dihydric
and trihydric phenols, hydroxybenzoic acids, bis(hydroxyphenyl)alkanes, and
hydroxyquinolines. For example, 3,5-dimethyl4-chlorophenol is discussed at
pages 810 and 811 of that article and 2,4,4'-trichloro-2'-hydroxydiphenyl ether is
discussed at page 812.
One of the major problems associated with the use of phenolic
disinfectants in cleaning compositions is their unpleasant and undesirable odor.In order to overcome the odor problem, odor masking or odor repressing agents
are incorporated into cleaning compositions. Besides masking the odor of the
disinfectants, such compounds can also mask the odor of perfumes used to
enhance the aesthetic value of the cleaning compositions. In addition, the
amounts of odor masking or odor repressing agents necessary to mask the odor
of the disinfectants increases the cost of the cleaning products.
SUMMARY OF THE INVENTION
This invention relates to compositions and methods which reduce the
unpleasant odor of cleaning compositions containing disinfectants. One aspect
of the present invention is a method for reducing the unpleasant odor of
disinfectant cleaning compositions by increasing the efficacy of an odor maskingor odor repressing agent in an aqueous cleaning composition containing a
disinfectant such as a bactericide. The compositions according to the invention
contain a nonionic sugar surfactant such as an alkyl glucose ester, an
aldobionamide, a gluconamide, a glyceramide, a glyceroglycolipid and
polyhydroxy fatty acid amide surfactant, an alkyl polyglycoside or any
combination of such surfactants and a compound having anti-bacterial activity
selected from the group consisting of halo-substituted monohydric phenol
compounds, halo-substituted dihydric phenol compounds, halo-substituted
trihydric phenol compounds, halo-substituted hydroxybenzoic acids, halo-

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substituted bis(hydroxyphenyl)alkanes and quaternary ammonium bromides
selected from the group consisting of lauryl dimethylbenzyl ammonium bromide,
alkyl trimethyl ammonium bromide, alkyl isoquinolinium bromide and an odor-
masking agent selected from the group consisting of 3,5,5-trimethylhexanal,
oxygenated monoterpenes such as citral, a- and ~-ionone, natural citrus oils, and
mixtures thereof.
The present invention also relates to highly concentrated cleanin
compositions containing eleva~:ed levels of disinfectants such as a bactericide as
disclosed herein. Such compositions can be made by combining a nonionic
sugar surfactant such as alkyl glucose ester, aldobionamide, gluconamide,
glyceramide, glyceroglycolipid and a polyhydroxy fatty acid amide surfactant, and
an alkyl polyglycoside and either or both of: (a) an anionic surfactant such as an
alkyl ether sulfate, (b) a mixture of at least two different alkyl polyglycosides
wherein each alkyl polyglycoside has a different average carbon chain length in
the alkyl moiety. The incorporation of (a) and/or (b) above produces a
composition which is more stable at high solids levels and permits the
preparation of highly concentrated compositions according to the invention
having relatively large amounts of disinfectant.
This invention also relates to a process for increasing the efficacy of an
odor masking or odor repressing agent which comprises adding an effective
amount of a nonionic sugar surfactant or a combination of an anionic surfactant
and a sugar surfactant to a composition comprised of an anti-bacterial
compound as set forth herein and an odor masking or odor repressing agent as
set forth herein.
This invention also relates to a process for making an anti-bacterial
cleaning composition which comprises adding a composition containing an
effective amount of a nonionic sugar surfactant, an anti-bacterial compound as
set forth herein and an odor masking or odor repressing agent as set forth herein
to an aqueous composition containing one or more additional nonionic
surfactants, anionic surfactants, amphoteric surfactants, and combinations
thereof surfactants in addition to other compounds such as builders, hydrotropes,
humectants, etc.

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DESCRIPTION OF THE PREFERRED EMBODIMENTS
Otiher than in the claims and in the operating examples, or where
otherwise indicated, all numbers expressing quantities of ingredients or reaction
conditions used herein are to be understood as modified in all instances by the
5 term"about".
The term nonionic sugar surfactant as used herein refers to surfactants
that are based on saccharide moieties. Representative examples of such
nonionic sugar surfactants include, but are not limited thereto, alkyl glucose
ester, aldobionamide, gluconamide, glyceramide, glyceroglycolipid and
polyhydroxy fatty acid amide surfactants, and alkyl polyglycosides each of whichis described more fully hereinbelow.
The alkyl glucose ester sugar surfactants are generally disclosed in U.S.
patent Nos. 5,109,127 and 5,190,747 the entire contents of both of which are
incorporated herein by reference. These surfactants have the general formula i:

RC(O)CH2
0

HO ~
H OH
wherein R represents a fatty acid residue of 6 to 20 carbon atoms, preferably 6
to 12 carbon atoms and R' represents an alkyl group having 2 to 6 carbon
atoms. Representative examples of such alkyl glucose esters are 1-ethyl-6-
caprylglucoside, 1-ethyl-6-laurylglucoside, 1-butyl-6-caprylglucoside, 1-ethyl-6-
palmitylglucoside and 1-ethyl-6-oleylglucoside.
The aldobionamide sugar surfactants are generally disclosed in U.S.
Patent No. 5,310,542 and in published European PatentApplication No. 550,281
both of which are incorporated herein by reference. An Aldobionamide is
generally defined as the amide of an aldobionic acid or aldobionolactone and an
aldobionic acid in turn is defined as a sugar substance (e.g. any cyclic sugar) in
which the aldehyde group has been replaced by a carboxylic acid which upon

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drying is capable of cyclizing to form an aldonolactone. The aldobionamides can
be based on compounds comprising two saccharide units, e.g. Iactobionamides,
maltobionamides, cellobionamides, melibionamides, orgentiobionamides, orthey
can be based on compounds comprising more than two saccharide units
provided that the polysaccharide has a terminal sugar unit with an aldehyde
group available.
The preferred aldobionamides of the present invention are
lactobionamides of the formula 11

rOH
OH o

H ~ NRlR2
H ~ OH
~OH ~ /

~- OH


wherein R' and R2 are the same or different and are selected from hydrogen and
an aliphatic hydrocarbon radical containing up to about 36 carbon atoms (e.g.
alkyl groups and alkenyl groups which groups may also include a heteroatom
such as N, O, S, present, for instance, as an amide, carboxy, ether and/or
saccharide moiety) except that R' and R2 cannot simultaneously be hydrogen.
The aliphatic hydrocarbon radical preferably contains up to 24 carbon atoms,
most preferably from 8 to 18 carbon atoms. Representative examples of such
lactobionamides are N-propyl lactobio"an, ~'c, N-pentyl lactobionamide, N-decyl
Iactobionamide, N-hexadecyl lactobionamide, N-oleyl lactobionamide, N-
dodecyl-N-methyl lactobionamide, and N-dodecyloxypropyl lactobionamide.
The gluconamide sugar surfactants are generally clisclosed in U.S. Patent
5,352,386 the entire contents of which is incorporated herein by reference. These
have the general formula 111:

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HOCH2-(CHOH)m-C(O)-NHR

wherein m is an integer from 2 to 5; and R is a straight or branched, saturated
or unsaturated aliphatic hydrocarbon having 4 to about 24 carbon atoms,
preferably 8 to 24 carbon atoms, which R group can also contain a heteroatom
selected from the group consisting of oxygen, nitrogen and sulfur. Representative
examples of such are N-octylerythronamide, N-decylerythronamide, N-
dodecylerythronamide, N-tetradecylerythronamide, N-decylxylonamide and N-
dodecylxylonamide.
The glyceramide sugar surfactants are generally disclosed in U.S. Patent
5,352,387, the entire contents of which are incorporated herein by reference.
These surfactants have the general formula:

HOCH2CH(OH)C(O)NHR

wherein R is a C8 to C24 straight or branched chained, saturated or unsaturated
aliphatic hydrocarbon in which the R group may also be substituted by a
heteroatom selected from oxygen, nitrogen and sulfur. Representative examples
of such surfactants are N-octylglyceramide, N-decylglyceramide and N-
hexadecylglyceramide.
The glyceroglycolipid sugar surfactants are generally disclosed in U.S.
Patent 5,358,656, and published European Patent Application No. 550,279, the
disclosure of each of which is incorporated herein by reference. The
glyceroglycolipids can be of the formula IV:

A1-O-CH2-CH(B)-CH2NRR1

wherein A1 is a saccharide, preferably having one or more saccharide units, morepreferably a mono or disaccharide and most preferably a monosaccharide such
as glucose or galactose; R and R1 are the same or different and are hydrogen,
a branched or unbranched hydrocarbon radical having from 1 to about 24,
preferably from about 6 to about 18 carbon atoms; B is OH or a NR2R3 group,

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wherein R2 and R3 may be the same or difFerent and are hydrogen, a branchecl
or unbranched hydrocarbon radical having 1 to 24, preferably from 6 to 18
carbon atoms, and NRR, and B are positionally interchangeable. Representative
examples of such surfactants are 3-(butylamino)-2-hydroxypropyl-~-D-
galactopyranoside, 3-(octylarnino)-2-hydroxypropyl-~-D-galactopyranoside, 3-
(eicosylamino)-2-hydroxypropyl-~B-D-galactopyranoside, 3-(butylamino)-2-
hydroxypropyl-,B-D-glucopyranoside, and 3-(pentylamino)-2-hydroxypropyl-,B-D-
mannopyranoside.
Other glyceroglycolipid surfactants are disclosed in published European
Patent Application No.550,280 which is incorporated herein by reference. These
surfactants are of the formula:

A'-O-CH2-CH(OR,)-CH20R

wherein A' is from 1 to 4 saccharide units and more preferably represents a
mono or disaccharide, and most preferably a monosaccharide, for example,
glucose or galactose; R and R1 are the same or different and are hydrogen, or
a branched or unbranched, salturated or unsaturated, hydrocarbon radical having
from 1 to 24 carbon atoms, preferably from ~ to 18 carbon atoms. Representative
examples of such surfactants are 3-(butyloxy)-2-hydroxypropyl-,B-D-
galactopyranoside, 3-(eicosyloxy)-2-hydroxypropyl-~-D-galactopyranoside, 3-
(decyloxy)-2-hydroxypropyl-~-D-galactopyranoside,3-(butyloxy)-2-hydroxypropyl-
,B-D-glucopyranoside, 3-(octyloxy)-2-hydroxypropyl-~-D-mannopyranoside, 3-
(tetradecyloxy)-2-hydroxypropyl-~-D-l~ctosiç!e, 3-(octadecyloxy)-2-hydroxypropyl-
~-D-maltoside, 3-(octyloxy)-2-hydroxypropyl-~-D-galactotrioside, and 3-
(dodecyloxy)-2-hydroxypropyl--~-D-cellotrioside.
The polyhydroxy fatty acid amide sugar surfactants are generally
disclosed in U.S. Patent Nos. 5,174,927, 5,223,179 and 5,332,528 the entire
disclosure of each of which is incorporated herein by reference. The polyhydroxyfatty acid amide surfactant component of the present invention comprises
compounds of the structural formula V

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R2C(O)N(R')Z

wherein: R' is H, C,-C4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl or a
mixture thereof, preferably C,-C4 alkyl, more preferably C, or C2 alkyl, most
preferably C, alkyl (i.e., methyl); and R2 is a Cs-C3, hydrocarbyl, pre~erably
straight chain C7-C19 alkyl or alkenyl, more preferably straight chain Cg-C~7 alkyl
or alkenyl, most preferably straight chain C"-C,7 alkyl or alkenyl, or mixture
thereof; and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with
at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative
(preferably ethoxylated or propoxylated) thereof. Z preferably will be derived from
a reducing sugar in a reductive al"i"dlion reaction; more preferably Z is a glycityl.
Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose,mannose, and xylose. As raw materials, high dextrose corn syrup, high fructose
corn syrup, and high maltose corn syrup can be utilized as well as the individual
sugars listed above. These corn syrups may yield a mix of sugar components for
Z. It should be understood that it is by no means intended to exclude other
suitable raw materials. Z preferably will be selected from the group consisting of
-CH2 -(CHOH)n-CH2 OH, -CH(CH2 OH)-(CHOH)n, -CH2 OH,
-CH2-(CHOH)2(CHOR')(CHOH)-CH2OH, where n is an integer from 3 to 5,
inclusive, and R' is H or a cyclic or aliphatic monosaccharide, and alkoxylated
derivatives thereof. Most preferred are glycityls wherein n is 4, particularly
-CH2-(CHOH)4-CH20H .
In the above Formula R' can be, for example, N-methyl, N-ethyl, N-propyl,
N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl. R2C(O)N< can
be, for example, cocamide, stearamide, oleamide, lauramide, myristamide,
capricamide, palmitamide, tallowamide, etc.
Z can be 1-deoxyglucityl, 2-deoxyfructityl, 1-deoxymaltityl, 1-deoxylactityl,
1-deoxygalactityl, 1-deoxymannityl, 1-deoxymaltotriotityl, etc. Representative
examples of such cosurfactants are N-methyl-N-1-deoxyglucityl cocoamide and
N-methyl-N-1-deoxyglucityl tallowamide.

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Other suitable polyhydroxy fatty acid amide surfactants (see U.S. Patent
Nos. 5,223,179 and 5,33~,491, the entire contents of each which are
incorporated herein by reference) are those of the formula Vl:

RC(O)N(R')CH2CH(OH)CH20H

wherein R is a C7-C2, hydrocarbyl species, i.e. coconut, tallow, palm fatty alkyl
and oleyl, and R1 is a C, to C6 hydrocarbyl or substituted hydrocarbyl species, i.e.
N-alkyl N-(1,2-propanediol) and N-hydroxyalkyl-N-1,2-propane diol fatty acid
amides. Representative examples of such cosurfactants are the tallow amide of
3-[2-(hydroxyethyl)amino]-1,2-propanediol (HEAPD), the palmitate amide of 3-
methylamino-1,2-propanediol (MAPD) and the lauramide of l\/IAPD.
The alkyl polyglycoside surfactants are compounds of the formula Vll
R,O(R20)b(Z)~ Vl I
wherein R, is a monovalent organic radical having from about 6 to about 30
carbon atoms; R2 is divalent alkylene radical having from 2 to 4 carbon atoms;
Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a
value from 0 to about 12; a is a number having a value from 1 to about 6.
Preferred alkyl polyglycosides which can be used in the compositions according
to the invention have the formula Vll wherein Z is a glucose residue and b is
zero. Such alkyl polyglycosides are commercially available, for example, as
APG~), GLUCOPON(~), or PLANTAREN~), surfactants from Henkel Corporation,
Ambler, PA.,19002. Examples of such surfactants include but are not limited to:
1. GLUCOPON~) 225 Surfactant - an alkyl polyglycoside in which the alkyl group
contains 8 to 10 carbon atoms and having an average degree of polymerization
of 1.7.
2. GLUCOPON(E~) 425 Surfactant - an alkyl polyglycoside in which the alkyl groupcontains 8 ~to 16 carbon atoms and having an average degree of polymerization
of 1.55.
3. C;LUCOPON(g) 625 Surfactant - an alkyl polyglycoside in which the alkyl groupcontains 12 to 16 carbon atoms and having an average degree of polymerization
of 1.6.

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4. APG~ 325 Surfactant - an alkyl polyglycoside in which the alkyl group
contains 9 to 11 carbon atoms and having an average degree of polymerization
of 1.6.
5. GLUCOPON~) 600 Surfactant - an alkyl polyglycoside in which the alkyl group
5 contains 12 to 16 carbon atoms and having an average degree of polymerization
of 1.4.
6. PLANTAREN(~) 2000 Surfactant - a C8 ,6 alkyl poiyglycoside in which the alkylgroup contains 8 to 16 carbon atoms and having an average degree of
polymerization of 1.4.
7. PLANTAREN(~) 1300 Surfactant - a C12-16 alkyl polyglycoside in which the alkyl
group contains 12 to 16 carbon atoms and having an average degree of
polymerization of 1.6.
Other examples include alkyl polyglycoside su, r~.ilanl compositions which
are comprised of mixtures of compounds of formula Vll wherein Z represents a
moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; a is
a number having a value from 1 to about 6; b is zero; and R, is an alkyl radicalhaving from 8 to 20 carbon atoms. The compositions are characterized in that
they have increased surfactant properties and an HLB in the range of about 10
to about 16 and a non-Flory distribution of glycosides, which is comprised of a
mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having
varying degrees of polymerization of 2 and higher in progressively decreasing
amounts, in which the amount by weight of polyglycoside having a degree of
polymerization of 2, or mixtures thereof with the polyglycoside having a degree
of polymerization of 3, predominate in relation to the amount of monoglycoside,
said composition having an average degree of polymerization of about 1.8 to
about 3. Such compositions, also known as peaked alkyl polyglycosides, can be
prepared by separation of the monoglycoside from the original reaction mixture
of alkyl monoglycoside and alkyl polyglycosides after removal of the alcohol. This
separation may be carried out by molecular distillation and normally results in the
removal of about 70-95% by weight of the alkyl monoglycosides. After removal
of the alkyl monoglycosides, the relative distribution of the various components,
mono- and poly-glycosides, in the resulting product changes and the

CA 0222~016 1997-12-18
WO 97~00~0~ PCT~US96J09244
11
concentration in the product of the polyglycosides relative to the monoglycos.deincreases as well as the concentration of individual polyglycosides to the totai,
i.e. DP2 and DP3 fractions in relation to the sum of all DP fractions. Such
compositions are disclosed in U.S. patent 5,266,690, the entire contents of which
~ 5 are incorporated herein by reference.
Other alkyl polyglycosides which can be used in the compositions
according to the invention are those in which the alkyl moiety contains from 6 to
18 carbon atoms in which and the average carbon chain length of the
composition is from about 9 to about 14 comprising a mixture of two or more of
at least binary components of alkyl polyglycosides, wherein each binary
component is present in the mixture in relation to its average carbon chain length
in an amount effective to provide the surfactant composition with the average
carbon chain length of about 9 ~o about 14 and wherein at least one, or both
binary components, comprise a Flory distribution of polyglycosides derived from
an acid-catalyzed reaction of an alcohol containing 6-20 carbon atoms and a
suitable saccharide from which excess alcohol has been separated.
Preferred nonionic sugar surfactants are alkyl polyglycosides as set forth
above.
The mixtures of alkyl polyglycosides which are useful for making highly
concentrated cleaning compositions containing elevated levels of disinfectants
such as a bactericide are combinations of alkyl polyglycosides wherein each of
the alkyl moieties contains from 8 to 16 carbon atoms on the average. Thus, for
example, a mixture containing an alkyl polyglycoside having an average carbon
chain length of 8 carbons in the alkyl moiety and an alkyl polyglycoside having
an average carbon chain length of 16 carbons in the alkyl moiety can be used to
make highly concentrated cleaning compositions containing elevated levels of
disinfectants such as a bactericide. The preferred mixture of alkyl polyglycosides
contains a C,0 and a C,2 alkyl polyglycoside. The relative amount of each alkyl
polyglycoside will depend upon a number of variables such as the nature of the
alkyl polyglycosides, the type of antibacterial compound, the presence of other
surfactants and the nature of the odor-masking agent. The relative amount of
-

CA 0222~016 1997-12-18
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each alkyl polyglycoside by weight can range from 30/70 to about 70/30 with the
preferred being from 40/60 to about 60/40.
An effective amount of sugar surfactant according to the invention is any
amount sufficient to decrease the amount of odor masking or odor repressing
agent relative to the amount of odor masking or odor repressing agent that wouldbe required without the use of a sugar surfactant. This amount can be readily
determined by one of ordinary skill in the art and will typically vary from a sugar
surfactant /odor masking agent weight ratio of from about 2/1 to about 45/1. Thepreferred sugar surfactant is alkyl polyglycoside.
The term anti-bacterial agent as used herein includes compounds which
are bacteriocidal and bacteriostatic.
The compositions and processes according to the invention are
particularly effective when the anti-bacterial compound is a halo-substituted
monohydric phenol, a halo-substituted dihydric phenol, a halo-substituted
trihydric phenol compound, halo-substituted hydroxybenzoic acid, and a halo-
substituted bis(hydroxyphenyl)alkane.
By "halo-substituted" it is meant that the compound has one or more
halogen atoms, preferably chlorine or bromine, covalently bonded to the phenolicring. The compounds may also have other substituents, e.g. alkyl groups,
aralkyl groups, alkaryl groups, alkoxy groups, aryloxy groups, alkaryloxy groups,
and aralkoxy groups. The terms dihydric phenol and trihydric phenol are meant
to include both compounds wherein the hydroxyl groups of the compound are all
on one phenyl group (e.g. a resorcinol derivative) and compounds wherein two
or more hydroxyl groups are distributed among two or more phenyl groups in the
compound (e.g. a hydroxyphenyl phenol derivative). The compounds can be in
the free hydroxyl form or a salt thereof, e.g. sodium, calcium, or ammonium.
Examples of suitable phenolic compounds include but are not limited to
halo-phenols, preferably ortho- or para-substituted (e.g. o-chlorophenol, p-
chlorophenol, o-bromophenol, and p-bromophenol), alkyl-halo-phenols, for
preferably C, to C7 normal alkyl-substituted halo-phenols (e.g. 2-chloro4-methyl-
phenol, 4-chloro-2-methyl-phenol, 2-bromo4-methyl-phenol, 4-bromo-2-methyl-
phenol, 2-chloro4-(n-heptyl)-phenol 4-chloro-3,5-dimethyl-phenol, and 4-chloro-




,

CA 0222~016 1997-12-18
WO 97/00~09 PCT~US96~09244

3,5-di(n-heptyl)-phenol), aralkyl-halo-phenois, preferably benzyl-halo-phenols
(e.g. p-chloro-o-benzyl-phenol), aryl-halo-phenols, preferably phenyl-halo-
phenols (e.g. p-chloro-o-phenyl-phenol), dihydric phenols, preferably hydroxy-
halo-phenyloxy-halo-phenols (e.g. 2,4,4'-trichloro-2'-hydroxydiphenyl ether) andbis(hydroxy-halo-phenyl)alkanes, preferably bis(hydroxy-halo-phenyl)methanes
(e.g. 2,2'-methylenebis(4-chlorophenol) and 2,2'-methylenebis(3,4,6-
trichlorophenol). The process according to the invention is most effective when
the anti-bacterial compound is 4-chloro-3,5-dimethyl-phenol (also known as p-
chloro-meta-xylenol, "PCMX") .
The process according to the invention is also particularly effective when
the anti-bacterial compound is one or more quaternary ammonium bromide
compounds selected from the group consisting of lauryl dimethylbenzyl
ammonium bromide, commercially available as, for example, AMOMYL~ BR
1244 a trademark product of Seppic; alkyl trimethyl ammonium bromide,
commercially available as, for example, EMPIGEN~ CHB 40, a trademark
product of Albright & Wilson; alkyl isoquinolinium bromide, commercially
available as, for example, CATINAL(~) CB 50, a trademark product of Toho
Chemical.
The amount of anti-bacterial compound which can be used in cleaning
compositions is any disinfecting amount or anti-bacterially effective amount andwill depend upon the concentration or the use dilution. The amount will typically
vary from 0.1% to 5% by weight.
The anionic surfactants that can be used in combination with the sugar
surfactants to produce cli~i"reclant cleaning compositions which are more stableat elevated total solids levels are selected from the group consisting of alkyl
sulfates, alkyl ether sulfates, alkyl sulfonates, alkyl ether sulfonates, and
sulfosuccinates. The preferred type of anionic surfactant is an alkyl ether sulfate.
The amount of such anionic surfactant is any amount which will produce a stable
composition that will not separate or become otherwise unstable upon prolonged
standing. The amount of anionic surfactant can be readily determined by one of
ordinary skill in the art and will typically vary from an anionic
sur~actanVantibacterial compound weight from about 8/1 to about 17/1 with the




,

CA 0222~0l6 l997-l2-l8
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14
preferred amount being from about 1/1 to about 3/1.
The process according to the invention can be employed for any type of
odor masking or odor repressing agent such as those described in an article
entitled "Odor Modification" in Encyclopedia of Chemical Technoloqy. vol.16,
pp. 303-304 (Kirk-Othmer, eds., John Wiley & Sons, Inc. N.Y., N.Y., 3d ed.
1981). These compounds include 3,5,5-trimethylhexanal, oxygenated
monoterpenes such as citral, a- and ~-ionone, natural citrus oils, and mixtures
thereof. Preferred odor masking or odor repressing agents include Mask
#39741 and Fragrance 49627, which are combinations of aromatic aldehydes,
esters, alcohols, and oxygenated monoterpenes such as ionones, available from
Flavor and Fragrance Specialties, Franklin Lakes, NJ.
One preferred embodiment of the present invention is a composition
containing an effective amount of an alkyl polyglycoside surfactant of the formula
Vll
R,O(R2O)b(Z)~ Vl l
wherein R1 is a monovalent organic radical having from about 6 to about 30
carbon atoms; R2 is divalent alkylene radical having from 2 to 4 carbon atoms;
Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a
value from 0 to about 12; a is a number having a value from 1 to about 6 is
added to a composition comprised of an effective amount of 4-chloro-3,5-
dimethyl-phenol (p-chloro-meta-xylenol) and an effective amount of Mask
#39741. A preferred alkyl polyglycoside is one in which the alkyl group contains8 to 16 carbon atoms and having an average degree of polymerization of 1.55.
The following examples are meant to illustrate but not to limit the
invention.

EXAMPLE 1
A Concentrated Disinfectant Composition Containing Anionic Surfactant
The following disinfectant cleaning composition was a clear fluid product:
17.9 grams of GLUCOPON(I~ 600 Surfactant (50%)
53.8 g of C,2H25(EO)3SO4Na (50%)
20 g of 4-chloro-3,5-dimethyl-phenol (PCMX)
6.7 g of Mask #39741
1.6 g of ethanol

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W O 97/00609 PCT~US96/09244

E~CAMPLE 2
A Concentrated Disinfectant Composition Containing
A Mixture of Alkyl Polyglycosides
A clear, flowable, readily dilutable concentrate contained the following
ingredients:
Ingredient Wt. %
PLANTAREN~) 2000 37.42
GLUCOPON~ 625 37.42
Propylene glycol 13.00
PCMX 10.00
Fragrance 49627 1.67
The first three ingredients were heated together with mixing to 70~C. The
PCMX was then slowly mixed in while heating at 75-80~C. The mixture was
cooled to room temperature and the Fragrance 49627 was added. The pH was
15 adjusted to 7.0 with a 50% cil:ric acid solution.
A similar formulation containing either 74.8 % of PLANTAREN(~ 2000 or
74.8% of GLUCOPONOE) 625 did not form a clear uniform product.

Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 1996-06-17
(87) PCT Publication Date 1997-01-09
(85) National Entry 1997-12-18
Dead Application 2000-06-19

Abandonment History

Abandonment Date Reason Reinstatement Date
1999-06-17 FAILURE TO PAY APPLICATION MAINTENANCE FEE

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $300.00 1997-12-18
Maintenance Fee - Application - New Act 2 1998-06-17 $100.00 1997-12-18
Registration of a document - section 124 $100.00 1998-02-20
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
HENKEL CORPORATION
Past Owners on Record
DEMAIO, CHRISTINE
GESSLEIN, BRUCE W.
LAZAROWITZ, VIRGINIA L.
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 1997-12-18 1 44
Description 1997-12-18 15 703
Claims 1997-12-18 6 258
Cover Page 1998-04-14 1 30
Assignment 1997-12-18 8 277
PCT 1997-12-18 12 594