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Patent 2645226 Summary

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(12) Patent Application: (11) CA 2645226
(54) English Title: AN AQUEOUS CONVEYOR LUBRICANT COMPOSITION FOR USE IN THE FOODSTUFF INDUSTRY
(54) French Title: COMPOSITION DE LUBRIFIANT AQUEUX POUR CONVOYEUR CONCUE POUR L'INDUSTRIE ALIMENTAIRE
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • C10M 173/02 (2006.01)
(72) Inventors :
  • VIERBAUM, MELANIE (Germany)
  • DE RIJK, BEN (Germany)
  • MEIJER, HAMKE (Germany)
(73) Owners :
  • KAO CHEMICALS GMBH (Germany)
(71) Applicants :
  • KAO CHEMICALS GMBH (Germany)
(74) Agent: KIRBY EADES GALE BAKER
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 2007-03-28
(87) Open to Public Inspection: 2007-10-11
Examination requested: 2012-02-07
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP2007/002772
(87) International Publication Number: WO2007/112917
(85) National Entry: 2008-09-09

(30) Application Priority Data:
Application No. Country/Territory Date
06006957.2 European Patent Office (EPO) 2006-03-31

Abstracts

English Abstract

The invention refers to lubricant compositions, said lubricant compositions being particularly preferred for conveyor systems, especially in the foodstuff industry, which are suitable for lubricating, cleaning and disinfecting of the transport chains. More specifically, the invention refers to lubricant compositions for conveyor systems comprising: a) one or more phosphoric acid esters; and b) one or more ether carboxylates; and e) water; and c) one or more C6-C22 fatty acids, optionally ethoxylated with 1 to 20 moles of ethylene oxide; and/or d) one or more C6-C22 fatty alcohols, optionally ethoxylated with 1 to 20 moles of ethylene oxide wherein the weight ratio of component (a) to component (b) is in the range of 9:1 to 1:3. Said lubricant compositions can be used in conveyor systems for glass and/or plastic bottles, such as polyethylen terepthalate (PET) or polycarbonate (PC); cans, glass containers, drums, cardboard containers and similar items.


French Abstract

La présente invention concerne des compositions lubrifiantes, lesdites compositions lubrifiantes étant particulièrement préférées pour des systèmes de transport, plus particulièrement dans l'industrie des produits alimentaires, lesquelles compositions étant appropriées pour lubrifier, nettoyer et désinfecter les chaînes de transport. Plus spécifiquement, l'invention concerne des compositions lubrifiantes pour des systèmes de transport comprenant : a) un ou plusieurs esters d'acide phosphorique ; et b) un ou plusieurs carboxylates d'éther ; et e) de l'eau ; et c) un ou plusieurs acides gras en C6 à C22, éventuellement éthoxylés avec 1 à 20 moles d'oxyde d'éthylène ; et/ou d) un ou plusieurs alcools gras en C6 à C22, éventuellement éthoxylés avec 1 à 20 moles d'oxyde d'éthylène, le rapport en poids du composant (a) sur le composant (b) étant dans la gamme de 9/1 à 1/3. Lesdites compositions lubrifiantes peuvent être utilisées dans des systèmes de transport pour des bouteilles en verre et/ou en plastique, tels que le polyéthylène téréphtalate (PET) ou le polycarbonate (PC) ; des boîtes, des récipients en verre, des cylindres, des récipients en carton et des articles analogues.

Claims

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




Claims


1. A lubricant composition comprising the following
essential elements,
a) one or more phosphoric acid esters of formula (I)
Image
wherein
- R1 represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group, or a
R3 (OCH2CH2)m group;
- R2 represents hydrogen, a linear or branched,
saturated or unsaturated C6-C22 alkyl and/or alkenyl
group, or a R3 ( OCH2CH2) m group ;
- R3 represents hydrogen or a linear or branched,
saturated or unsaturated C6-C22 alkyl and/or alkenyl
group;
- m represents a number of from 1 to 15; and
- Z represents hydrogen or a cation
b) one or more ether carboxylates of formula (II)
R-O- (CH2CH2O)n-CH2COOM (II)

wherein
- R represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group;



2

- n represents a number of from 0.5 to 20, and-
- M represents hydrogen or a cation, selected from the
group consisting of an alkali metal, an alkaline
earth metal, ammonium, an alkylammonium, an
alkanolammonium or a glucammonium; and
e) water; and
c) one or more C6-C22 fatty acids, optionally ethoxylated
with 1 to 20 moles of ethylene oxide; and/or
d) one or more C6-C22 fatty alcohols, optionally
ethoxylated with 1 to 20 moles of ethylene oxide
wherein the weight ratio of component (a) to component
(b) is in the range of 9:1 to 1:3.

2. An aqueous lubricant composition according to claim
1, wherein the weight ratio of component (a) to component (b)
is in the range of 5:1 to 1:3.

3. An aqueous lubricant composition according to claim 1
or 2, wherein the phosphoric acid esters of formula (I)
comprise a mixture of mono- and di-esters.

4. An aqueous lubricant composition according to claim
3, wherein the weight ratio phosphoric mono-esters to
phosphoric di-esters is from 50:50 to 95:5.

5. An aqueous lubricant composition according to claims
1 to 3, wherein the C16-C18 proportion in the alkyl and/or
alkenyl groups of the phosphoric acid esters is higher than
70%.

6. An aqueous lubricant composition according to any of
the preceding claims, wherein the phosphoric acid esters of



3

formula (I) are ethoxylated having an average ethoxylation
degree from 2 to 8.

7. An aqueous lubricant composition according to any of
the preceding claims, wherein in the ether carboxylates of
formula (II) n has a value in the range of 1 to 10 and M is
hydrogen, sodium or potassium.

8. An aqueous lubricant composition according to any of
the preceding claims, wherein the C16-C18 proportion in the
fatty acids is higher than 70%.

9. An aqueous lubricant composition according to any of
the preceding claims, wherein the C16-C18 proportion in the
fatty alcohols is higher than 70%.

10. An aqueous lubricant composition according to any of
the preceding claims, comprising, expressed as weight
percentage,
a) 10-85% of the phosphoric acid esters of formula (I)
b) 5-60% of the ether carboxylates of formula (II)
c) 0.1-30% of the fatty acids
d) 0.1-30% of the fatty alcohols
e) water add up to 100%, .

11. An aqueous lubricant composition according to any of
the preceeding claims, wherein the ether carboxylates of
formula (II) are a mixture of
I) C6-C10 alkyl and/or alkenyl ether carboxylates
having an average ethoxylation degree from 2 to 8
II) C12-C18 alkyl and/or alkenyl ether carboxylates
having an average ethoxylation degree from 1 to 10



4

12. An aqueous lubricant composition according to claim
11, comprising, expressed as weight percentage,
a) 15-55% of the phosphoric acid esters of formula (I)
b1) 5-20% of C6-C10 alkyl and/or alkenyl ether
carboxylates having an average ethoxylation degree from
2 to 8
b2) 10-45% of C12-C18 alkyl and/or alkenyl ether
carboxylates having an average ethoxylation degree from
1 to 10
c) 1-20% of the fatty acids
d) 1-20% of the fatty alcohols
e) water add up to 100%.

13. An aqueous lubricant concentrated composition
according to claims 11 or 12, wherein the weight ratio of the
C12-C18 alkyl and/or alkenyl ether carboxylates to the C6-C10
alkyl and/or alkenyl ether carboxylates is in the range of
8:1 to 1:5.

14. An aqueous lubricant composition obtainable by
diluting an aqueous lubricant composition according to claims
to 13 by a factor of 2 to 10000 by volume, preferably from
5 to 1000.

15. Process for lubricating conveyor systems consisting
of applying an aqueous lubricant diluted composition
according to any one of the preceding claims to a conveyor
system continuosly or at intervals.

16. Process according to claim 15 wherein the conveyor
system is for glass bottles, plastic bottles such as
polyethylene terephtalate (PET) or polycarbonate (PC)




bottles, cans, glass containers, drums, cardboard containers
and similar items.

17. Use of an aqueous lubricant diluted composition
according to any one of the preceding claims for lubricating
conveyor systems.

18. Use according to claim 17 wherein the conveyor
system is for glass bottles, plastic bottles such as
polyethylene terephtalate (PET) or polycarbonate (PC)
bottles, cans, glass containers, drums, cardboard containers
and similar items.

Description

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



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LUBRICANT COMPOSITION

DESCRIPTION
Technical field

The present invention refers to lubricant compositions,
said lubricant compositions being particularly preferred for
conveyor systems, especially in the foodstuff industry, which
are suitable for lubricating, cleaning and disinfecting of
the transport chains. More specifically, the invention refers
to the use of these compositions as lubricants, particularly
in conveyor systems for glass andJor plastic bottles, such as
polyethylen terepthalate (PET) or polycarbonate (PC); cans,
glass containers, drums, cardboard containers and similar
items.

Prior Art

Usually, in bottle and barrel plants of drinks' manu-
facturers and in food packaging, articulated plate conveyor
belts or other transport systems are used. Said systems are
maintained lubricated to reduce the mechanical strength of
the bottles and containers, and cleaned to remove dirt and to
avoid contamination by micro-organisms, with the aid of
appropriate aqueous lubricating agents, preferentially
applied with automatic lubrication systems for conveyor belts
or other transport systems, equipped with a sprayer system.
Normally, for this purpose soap-based lubricants (based
on inorganic or organic alkaline salts of a fatty acid or a
mixture of fatty acids that contain a minimum of 8 carbon
atoms) have been used.
However, soap-based lubricants present several
disadvantages:


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- To complex the water hardness the lubricants must
contain the corresponding amounts of ethylendiami-
notetraacetic or nitrylotriacetic acid. This prevents
the formation of calcium salts that can block the nozzle
of the lubrication system.
- For harder waters, larger amounts of complexing agent
are required in the lubricant compositions, making it
necessary to reduce the soap contents in the finished
product. However, this reduces the lubricant effect of
the preparation.
- Soap-based lubricant compositions have a relatively
intense foam production since it is very difficult to
defoam soaps that have already formed. The excess foam
produced by the lubricant is lost when lubricating the
conveyor belts and can penetrate the goods transported.
On the other hand, foam production on conveyor belts
hinders the automatic control of these recipients.
- The use of softened water to prevent calcium soap foam
formation in products with no complexing agent or with
only a reduced amount increases the cost of using these
products.
- The compound ethylendiaminotetraacetic acid (EDTA) is
not readily biodegradable in standard biodegradability
tests (ASTM or OECD criteria for ready or inherent

biodegradability)
Because of these drawbacks, soap-based lubricants have
been increasingly replaced by

- lubricants based on fatty amines and/or diamines, or
- lubricants based on phosphoric esters.

Furthermore, alkyl ether carboxylic acids or
carboxylates have also been used in lubricant compositions


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3
for conveyor systems either alone or in combination with
other chemicals.

For example, EP-A-0044458 describes mainly soap free
lubricants adapted for use as conveyor belt lubricants that
consist of:
a) a non ionic carboxylate compound of general formula
R- [O- (CH2) m] n-COOM
wherein R is a saturated or unsaturated alkyl group,
m=2-3, n=3-7 and M is H, an alkaline metal or an
alkanol amine cation,
b) an acylsarcosinate of general formula RCON(CH3)CH2COOM
wherein R is an alkyl or alkenyl group C11-C19, and M
is H, an alkaline metal or alkanol amine cation, and

c) water, and optionally a conventional non-ionic
surfactant that presents a HLB value between 10 and
12 to improve the detergency.

DE-A-4244536 describes lubricant compositions for bottle
conveyor belts that contain an N-alkyldiamine, its salt
obtained with an organic acid and, optionally, an organic
acid and an ether carboxylate of formula

R- ( OCZH4 ) XO ( CHZ ) yCOOH,
wherein R is an Clo-C2o alkyl group (preferably C16-C18),
x=1-20 (preferably 5-15) and finally y=0-5 (preferably 1).
DE-A-19642598 describes a lubricant concentrate for

conveyor belt installations in the food industry, based on
amines comprised by: i) one or more amines, ii) one or more
ether carboxylates, iii) one or more polyethyleneglycols and
iv) up to 99% in weight of the usual additives and adjuvants.
The ether carboxylates described are compounds of general
formula


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4
R- (O (CH2) m) nOCHzCOO-M+
wherein
R is selected from the group consisting of a saturated,
linear or branched C1-C22 alkyl rest, a mono or
polyunsaturated, linear or branched, alkenyl or alkynyl rest
with 2 to 22 carbon atoms and a mono or poly C1-C22 alkyl or
C2-C22 alkenyl or alkynyl substituted aryl rest; m is 2 or 3;
n is a positive number in the range of 1 to 30, and M is
hydrogen or an alkali metal.

US-A-5062979 describes an aqueous, optically clear,
substantially soap free lubricant composition having a pH
value in the range from 6 to 8, comprising water and:

(a) from 0.02 to 15% by weight based on the total
composition of alkyl benzene sulfonate molecules containing
to 18 carbon atoms in the alkyl part and having cations
that are selected from the group consisting of alkali metal
ions, ammonium ions and alkanolammonium ions containing 1 to
about 14 carbon atoms in the alkanolamine part;
(b) from 0.02 to 15% by weight based on the total
composition of partially esterified phosphonic acid or
phosphate molecules corresponding to general formula

R1-O ( -CH2-CH (R2) -O) n-PO3X
in which R1 is selected from the group consisting of
aliphatic monovalent hydrocarbon radicals containing about 12
to about 18 carbon atoms, R2 is H or CH3, X is hydrogen or an
alkali metal, and n is an integer in the range of about 8 to
about 12; and
(c) from 0.01 to 10% by weight of the total composition
of molecules selected from the group consisting of aliphatic
carboxylic acids containing about 6 to about 22 carbon atoms
and having a titer of not more than 20 C; and, optionally,

(d) conventional solubilizers, solvents, foam


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inhibitors, disinfectants, or mixtures thereof,

component (a) and component (b) being present in a ratio by
weight of about 3:1 to about 1:3 and component (c) being
present in a ratio by weight to the sum of components (a) and
(b) of from about 1:20 to about 1:4.

DE-A-19846991 describes a chain lubricant for conveyor
and transport systems comprising water, a surfactant selected
from the group consisting of
a) a monoalkyl-polyalkyleneglycol ether carboxylic acid
of the following formula

Rl ( OC2H4 ) m (OC3H6 ) n0- ( CHz ) pCHR2C (O) OR3
wherein R1 is a saturated linear or branched C1-C22-alkyl
radical, a mono- or polyunsaturated linear or branched
alkenyl or alkynyl radical with 2 to 22 carbon atoms or
an aryl radical optionally substituted one or more times
by C1-C22-alkyl or alkenyl or alkynyl groups; m is a
number in the range of 0 to 30; n is a number in the
range of 0 to 30; p is a number in the range of 1 to 4;
R2 is a hydroxyl group or a hydrogen and R3 is hydrogen,
a methyl group or an alkali metal;
b) an alkyl-benzenesulphonic acid or one of its salts of
the following general formula

R4-C6H6-SO3 M (II)
wherein R4 is a saturated linear or branched C1-C22 -
alkyl radical or a mono- or poly-unsaturated linear or
branched alkenyl or alkynyl radical with 2 to 22 carbon
atoms and M is hydrogen or an alkali metal;
c) a monoalkyl-polyalkyleneglycol phosphoric acid mono
or diester of the general formula

(R5- (OCZH4) q- (OC3H6) r-O) s-PO2R6H
wherein RS is a saturated linear or branched C1-C22-alkyl
radical, a mono- or polyunsaturated linear or branched


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alkenyl or alkynyl radical with 2 to 22 carbon atoms or
an aryl radical optionally substituted one or more times
by C1-C22-alkyl or alkenyl or alkynyl groups; q is a
number in the range of 0 to 30; r is a number in the
range of 0 to 30; s is 1 or 2; R6 is hydroxyl if s is 1
and, if s is 2, R6 is not present; and

d) mixtures thereof;
and disinfection agents, as well as adjuvant and
additive materials, wherein said disinfection agent comprises
chlorine dioxide.

ES-A-2206052 describes the use as a lubricant of ether
carboxylates of formula

R- (OCH2CH2) -O-CH2COOX
wherein R is an alkyl, alkenyl or alkynyl residue
containing from 12 to 22 carbon atoms; n is a number
between 0.3 and 15; X is hydrogen, an alkaline metal, an
ammonium cation or an hydroxyalkylammonium cation.
According to ES-A-2206052, the described ether

carboxylates can be specifically used in conveyor systems.
EP-A-1652909 describes a corrosion inhibiting agent for
functional fluids, which are liquids used as lubricants,
abrasives, coolers for the metal working industry,
particularly hydraulic fluids (HF or HFA). EP-A-1652909
describes in Tables 1-3 water-mixable concentrates, which can
be used as corrosion inhibiting agents. Thus, Example 3 and
Comparative Example C of EP-A-1652909 describe water-mixable
concentrates comprising a fatty alcohol polyglycolether (3.6
wt.%), an oleic ether (5 EO) carboxylic acid (1.8 wt.%), tall
oil fatty acid (0.8 wt.o) and 2-ethylhexyl phosphoric acid
(2,0 wt.%). Although these compositions may present lubricant
properties, the disclosure of a fatty alcohol polyglycolether


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7
does not disclose a C6-C22 fatty alcohol, optionally
ethoxylated with 1 to 20 moles of ethylene oxide, as claimed
in the present invention.

US-A-4895668 describes an aqueous lubricant composition,
which comprises one or more carboxylated surfactants and one
or more non-carboxylated surfactants in combination with a
soap lubricant. Table 2 of US-A-4895668 describe lubricant
compositions comprising nonyl phenol ethoxylated with 9 moles
of ethylene oxide (5.0 wt.%), a sodium oleic ether (5 EO)
carboxylate (5.0 wt.%), and tall oil fatty acid (20.0 wt.%)
US-A-4895668 fails to disclose the phosphoric acid esters
according to the present invention. Furthermore, the
disclosure of the nonyl phenol ethoxylated does not
anticipate a C6-C22 fatty alcohol, optionally ethoxylated with
1 to 20 moles of ethylene oxide, as claimed in the present
invention. Finally, the lubricant properties of the
compositions described in US-A-4895668 are not appropriate
for both glass bottles and for PET bottles.

Fatty amines andJor diamines are chemicals of
environmental concern. In order to protect the environment
and human health, chemicals are tested and classified
according to their potential hazard. An important criterion
is the classification into Water Hazard Classes of the
Federal Environmental Agency of Germany (Umweltbundesamt).
Three Water Hazard Classes (WGK) are defined:

1: low hazard to water
2: hazard to water
3: severe hazard to water
One of the more commonly used diamines in conveyor
systems, oleyl diamine (N-Oleyl-1,3-diaminopropane) has been
classified as a chemical of severe hazard to water (Water


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Hazard Class 3)

On the other hand, phosphoric esters present stability
problems (2 phases formation) when they are diluted from a
concentrated composition and are sensitive to water hardness.
Furthermore, phosphoric esters alone do not show sufficient
lubricity in conveyor systems for plastic bottles, such as
polyethylen terepthalate (PET) or polycarbonate (PC).

It can be concluded from the existing prior art that the
industry still requires improvements in the field of
lubricant compositions for conveyor systems, which are free
from fatty amines and/or diamines, which can be obtained by
dilution from a concentrated composition whithout stability
problems, which do not present water hardness problems and
which can be applied to different materials (glass, PET,
cans, etc.) being more versatile.

Summary of the invention

The present invention offers an efficient solution to
the problems encountered in the prior art, by providing a
lubricant composition comprising the following elements,
a) one or more phosphoric acid esters of formula (I)
O

R1O-P-OR2 (I)
I
Oz
wherein

- R1 represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group, or a
R3 ( OCH2CH2 ) m group;


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- R2 represents hydrogen, a linear or branched,

saturated or unsaturated C6-C22 alkyl and/or alkenyl
group, or a R3 (OCH2CH2) m (group;

- R3 represents hydrogen or a linear or branched,
saturated or unsaturated C6-C22 alkyl and/or alkenyl
group;

- m represents a number of from 1 to 15; and

- Z represents hydrogen or an appropriate cation
b) one or more ether carboxylates of formula (II)
R-O- (CH2CH2O)n-CH2COOM (II)

wherein
- R represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group;

- n represents a number of from 0.5 to 20, and

- M represents hydrogen or an appropriate cation,
selected from the group consisting of an alkali
metal, an alkaline earth metal, ammonium, an
alkylammonium, an alkanolammonium or a glucammonium;
and

e) water; and
c) one or more C6-C22 fatty acids, optionally ethoxylated
with 1 to 20 moles of ethylene oxide; and/or

d) one or more C6-C22 fatty alcohols, optionally
ethoxylated with 1 to 20 moles of ethylene oxide
wherein the weight ratio of component (a) to component
(b) is in the range of 9:1 to 1:3, preferably in the range of
5:1 to 1:3, more preferably in the range of 2:1 to 1:2.

The subject matter of the present invention both
includes concentrated aqueous lubricant compositions and


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diluted aqueous lubricant coinpositions obtained by diluting
the previous lubricant compositions.
The present invention also provides a method for
lubricating conveyor systems consisting of applying an
aqueous lubricant diluted composition according to the
invention to a conveyor system continuosly or at intervals.

The present invention also provides the use of the
lubricant compositions for lubricanting conveyor systems.
Detailed description of the invention

The phosphoric acid esters

The phosphoric acid esters according to the invention
may be prepared by reacting in aqueous media C6-C22 fatty
alcohols with phosphorous pentoxide (P205).
The C6-C22 fatty alcohols are preferably derived from
natural fat and oil as well as synthetic origin. Preferred
fats and oils include palm oil, coconut oil, sunflower oil,
rapeseed oil, castor oil, olive oil, soybean oil; and animal
fat such as tallow, bone oil; fish oil, hardened oils and
semihardened oils thereof; and mixtures thereof. As a result
of its natural origin, the C6-C22 fatty alcohols that react
with the phosphorous pentoxide (P205) may contain a great
variety of alkyl and/or alkenyl groups, said groups being
linear or branched, saturated or unsaturated.
Particularly preferred are C6-C22 fatty alcohols are
derived from coconut oil, palm oil and olive oil. It is
particularly preferred that the C6-C22 fatty alcohols to be
reacted with the phosphoric acid esters are derived from
olive oil.
The phosphoric acid esters obtained by reacting in C6-C22


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fatty alcohols with phosphorous pentoxide (P205) are a mixture
of phosphoric mono-esters (mono-alkyl esters) and phosphoric
di-esters (di-alkyl esters) and the products obtained and the
reaction are well known to the skilled person (O'Lenick et
al., Soap Cosmetics and Chemical Specialities, July 1986, p.
26 . )
According to the invention it is preferred that the
weight ratio phosphoric mono-esters to phosphoric di-esters
is from 50:50 to 95:5, more preferred from 55:45 to 90:10.
According to the invention in the phosphoric acid esters
of formula (I) Z represents hydrogen or an appropriate
cation, said cation preferably being selected from the group
consisting of an alkali metal, an alkaline earth metal,
ammonium, an alkylammonium, an alkanolammonium or a
glucammonium. It is further preferred that Z represents
hydrogen or an alkali metal, preferably lithium, sodium or
potassium.
According to the invention, it is also preferred that
the C16-C18 proportion in the alkyl and/or alkenyl groups of
the phosphoric acid esters is higher than 70%, preferably
higher than 800, even more preferably higher than 850.
Optionally, the C6-C22 fatty alcohols are ethoxylated,
having an average ethoxylation degree from 1 to 10,
preferably from 2 to 8.
Examples of commercially available phosphoric acid
esters are FOSFODET 20 M (potassium salt of phosphoric
ester of lauric alcohol, mono-ester to di-ester ratio 80:20);

FOSFODET 0 20 D (potassium salt of phosphoric ester of lauric
alcohol, mono-ester to di-ester ratio 50:50), FOSFODET 0 8050
(phosphoric ester of hydrogenated tallow, mono-ester to di-
ester ratio 60:40), FOSFODET @ FJZ 903 (phosphoric ester of
ethoxylated (3 EO) oleyl alcohol, mono-ester to di-ester
ratio 55:45), all marketed by KAO Chemicals Europe.


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The ether carboxylates

Ether carboxylates of formula (II) are products well
known in the art. They are usually obtained by alkoxylation
and subsequent carboxymethylation of fatty alcohols as
described by Meijer and Smid in Polyether Carboxylates;
Anionic Surfactants; Surfactant Sciencie Series, Vol. 56 (p.
313-361), edited by Helmut W. Stache, ISBN: 0-8247-9394-3.
The process is divided into two steps. The first one is
the alkoxylation of alcohols under standard conditions known
by the skilled in the art. For instance, the polyoxyethylene
group is obtained by addition of ethylene oxide to fatty
alcohols, mostly with an alkaline catalyst such as NaOH, KOH
or NaOCH3, giving a broad polyoxyethylene oxide distribution
(broad ethoxylation degree). For special applications the
ethoxylation can be catalyzed by Lewis acids or by using
metallic Na or NaH to achieve a narrow range distribution
(narrow ethoxylation degree).
However, one may also start from commercially available
ethoxylated alcohols.
In the second step, the ethoxylated alcohols are reacted
with a strong base, like sodium or potassium hydroxide, in
presence of a reducing agent, i.e. sodium borohydride, to
obtain the corresponding alkoxylate, which is
carboxymethylated with sodium monochloroacetate (SMCA).
The ether carboxylates of formula (II) are derived from
C6-C22 fatty alcohols, which are preferably derived from
natural fat and oil as well as synthetic origin. Preferred
fats and oils include palm oil, coconut oil, sunflower oil,
rapeseed oil, castor oil, olive oil, soybean oil; and animal
fat such as tallow, bone oil; fish oil, hardened oils and


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semihardened oils thereof; and mixtures thereof. As a result
of its natural origin, the C6-C22 fatty alcohols that are
alkoxylated and subsequently carboxymethylated may contain a
great variety of alkyl and/or alkenyl groups, said groups
being linear or branched, saturated or unsaturated.
Particularly preferred are C6-C22 fatty alcohols are
derived from coconut oil, palm oil and olive oil. It is
particularly preferred that the C6-C22 fatty alcohols that are
alkoxylated and subsequently carboxymethylated are derived
from olive oil.
According to the invention, it is preferred that in the
ether carboxylates of formula (II) n has a value in the range
of 1 to 10, preferably in the range of 1 to 7, and M is

hydrogen, sodium or potassium.
Furthermore, it is also preferred that in the C6-C22
alkyl and/or alkenyl group in the ether carboxylates of
formula (II) the C16-C18 proportion is higher than 80%, more
preferred higher than 80%, even more preferred higher than
85a.
Examples of commercially available ether carboxylates of
formula (II) are AKYPO RO 10 VG (Oleic ether carboxylic
acid with an average ethoxylation degree of 1), AKYPO RO 20
VG (Oleic ether carboxylic acid with an average ethoxylation
degree of 2), AKYPO RO 50 VG (Oleic ether carboxylic acid
with an average ethoxylation degree of 5), and AKYPO RO 90
VG (Oleic ether carboxylic acid with an average ethoxylation
degree of 9), all marketed by KAO Chemicals Europe.

The fatty acids

According to the invention, the C6-C22 fatty acids can be
selected from natural and/or synthetic origin. Accordingly,


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natural fatty acids may also be used in addition to synthetic
fatty acids. The natural acids do not normally occur in pure
form and.are therefore preferably used for the purposes of
the invention in the form of mixtures, which may be obtained
from a variety of natural sources. Accordingly, the fatty
acids are preferably selected from hexanoic acid, heptanoic
acid, octanoic acid, nonanoic acid, 9-hexadecenoic acid,
9,12-octadecadienoic acid, 9,12,15-octadecatrienoic acid,
5,8,11,14-eicosatetraenoic acid, 4,8,12,15,19-
docosapentaenoic acid, sperm oil acid, coconut oil acid,
oleic acid, tall oil acid, sunflower oil acid, linseed oil
acid, and/or rapeseed oil acid.
The C6-C22 fatty acids are optionally ethoxylated with 1
to 20 moles of ethylene oxide, preferably with 1 to 10 moles
of ethylene oxide.
It is preferred that the C16-Cla proportion in the fatty
acids according to the invention is higher than 70%,
preferably higher than 80%, even more preferably higher than
85o.

The fatty alcohols

Fatty alcohols are aliphatic alcohols derived from
natural fats and oils. Due to their amphipathic nature, fatty
alcohols behave as nonionic surfactants. They find use as
emulsifiers, emollients and thickeners in cosmetics and food
industry.
Fatty alcohols are a common component of waxes, mostly
as esters with fatty acids but also as alcohols themselves.
Examples of C6-C22 fatty alcohols include capryl alcohol

(1-octanol), pelargonic alcohol (1-nonanol), capric alcohol
(1-decanol), lauryl alcohol (1-dodecanol), myristyl alcohol


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(1-tetradecanol), cetyl alcohol (1-hexadecanol), palmitoleyl
alcohol (cis-9-hexadecan-l-ol), stearyl alcohol (1-
octadecanol), isostearyl alcohol (16-methylheptadecan-l-ol),
elaidyl alcohol (9E-octadecen-l-ol), oleyl alcohol (cis-9-
octadecen-l-ol), linoleyl alcohol (9Z, 12Z-octadecadien-l-
ol), elaidolinoleyl alcohol (9E, 12E-octadecadien-l-ol),
linolenyl alcohol (9Z, 12Z, 15Z-octadecatrien-l-ol),
elaidolinolenyl alcohol (9E, 12E, 15-E-octadecatrien-l-ol),
ricinoleyl alcohol (12-hydroxy-9-octadecen-l-ol), arachidyl
alcohol (1-eicosanol), behenyl alcohol (1-docosanol), and
erucyl alcohol (cis-13-docosen-l-ol).
The C6-C22 fatty alcohols are optionally ethoxylated with
1 to 20 moles of ethylene oxide, preferably with.1 to 10
moles of ethylene oxide.
It is preferred that the C16-C18 proportion in the fatty
alcohols according to the invention is higher than 70%,
preferably higher than 80%, even more preferably higher than
850.

The lubricant composition

It is preferred that the lubricant composition according
to the invention comprises the following elements,
a) one or more phosphoric acid esters of formula (I)


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16
0
(1
R10-P-OR2 (I)
I
OZ
wherein

R1 represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group, or a
R3 ( OCH2CH2 ) n, group;

- R2 represents hydrogen, a linear or branched,
saturated or unsaturated C6-C22 alkyl and/or alkenyl
group, or a R3 ( OCH2CH2 ) m group;

R3 represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group;

- m represents a number of from 1 to 15; and

- Z represents hydrogen or an appropriate cation
b) one or more ether carboxylates of formula (II)
R-0- (CH2CH20) õ-CH2COOM ( I I )

wherein
- R represents a linear or branched, saturated or
unsaturated C6-C22 alkyl and/or alkenyl group;

- n represents a number of from 0.5 to 20, and

- M represents hydrogen or an appropriate cation,
selected from the group consisting of an alkali
metal, an alkaline earth metal, ammonium, an
alkylammonium, an alkanolammonium or a glucammonium;
and
c) one or more C6-C22 fatty acids, optionally ethoxylated
with 1 to 20 moles of ethylene oxide; and
d) one or more C6-C22 fatty alcohols, optionally


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ethoxylated with 1 to 20 moles of ethylene oxide

e) water; and
wherein the weight ratio of component (a) to component
(b) is in the range of 9:1 to 1:3, preferably in the
range of 5:1 to 1:3, more preferably in the range of 2:1
to 1:2.

The subject matter of the present invention also
includes an aqueous lubricant concentrated composition
comprising,-expressed as weight percentage,
a) 10-85% of the phosphoric acid esters of formula (I)
b) 5-60% of the ether carboxylates of formula (II)

c) 0.1-30% of the fatty acids
d) 0.1-300 of the fatty alcohols
e) water add up to 100%.

According to the invention, it is preferred that in the
aqueous lubricant concentrated composition the ether
carboxylates of formula (II) are a mixture of
I) C6-C10 alkyl and/or alkenyl ether carboxylates
having an average ethoxylation degree from 2 to 8
II) C12-C18 alkyl and/or alkenyl ether carboxylates

having an average ethoxylation degree from 1 to 10,
preferably from 1 to 7.

If is further preferred that the aqueous lubricant
concentrated composition according to the invention
comprises, expressed as weight percentage,
a) 15-55% of the phosphoric acid esters of formula (I)
bl) 5-20% of C6-Clo alkyl and/or alkenyl ether
carboxylates having an average ethoxylation degree from
2 to 8
b2) 10-45% of C12-C18 alkyl and/or alkenyl ether


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carboxylates having an average ethoxylation degree from
1 to 10

c) 1-20% of the fatty acids

d) 1-20% of the fatty alcohols
e) water add up to 100%.

Preferably, the weight ratio of the C12-C18 alkyl and/or
alkenyl ether carboxylates to the C6-Clo alkyl and/or alkenyl
ether carboxylates in the aqueous lubricant concentrated
composition according to the invention is in the range of 8:1
to 1:5, preferably in_the range of 5:1 to 1:2.
The active matter content of the aqueous lubricant
concentrated composition according to the invention is
preferably at least 30% by weight, more preferably at least
50% by weight, even more preferably at least 65% by weight,
the active matter of the composition is substantially
provided by components (a), (b), (c) and (d).

According to the invention, an aqueous lubricant diluted
composition can be obtained by diluting an aqueous lubricant
concentrated composition as described before by a factor of 2
to 10000 by volume, preferably from 5 to 1000. Said dilution
can be done directly in one step or through intermediate

partially diluted compositions, i.e. starting from a
concentrate, diluting it by a factor of 2 to 100, and finally
diluting it again to the desirable final concentration. This
procedure is commonly used to avoid transport and storage of
highly diluted compositions.
Aqueous lubricant compositions are usually applied in
very dilute form such that the active concentration applied
in the conveyor systems ranges from 0.01o to 2% by weight.
The total active matter (substantially provided by components
(a), (b), (c) and (d)) present in the lubricant diluted


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composition ranges from 0.01 to 1%, preferably from 0.02 to
0.5% by weight. Dilution of the lubricant concentrated -
composition to obtain lubricant diluted compositions, which
are those that are directly applied to the conveyor systems
can be done with hard water, semi-hard water or soft water.

The aqueous lubricant compositions according to the
invention can also contain additives such as ionic
surfactants, non ionic surfactants, amphoteric surfactants,
foam inhibitor agents, foam regulators, foam stabilizers,
complexing agents, chelating agents, solubilizers,
emulsifiers, biocides, bactericides, disinfectants,
fungicides, antioxidants, corrosion inhibitors and pH
regulators, either in the form of aqueous lubricant
concentrated compositions or aqueous lubricant diluted
compositions.
The pH of these aqueous lubricant compositions for
conveyor systems is preferably between 6.0 and 8.5, more
preferably between 6.5 and B.O.
The viscosity of the aqueous lubricant concentrated
composition of the present invention ranges from 50 to 20,000
mPa's at 20 C, more preferably from 100 to 10,000 mPa-s at
20 C.
When the aqueous lubricant concentrated composition of
the present invention is partially diluted to obtain a
partially diluted composition, i.e. in the range from 8 to
10% by weight, the viscosity of said partially diluted ranges
from 100 to 6,000 mPa's at 20 C, and it is preferably less
than 1,000 mPa's at 20 C.
The aqueous lubricant diluted composition of the present
invention has a viscosity equal or similar to the viscosity
of water at 20 C.


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As solubilizing agents, the compositions of the

invention may contain solubilizing agents that can be mixed
with water or that are water-soluble. Preferably, the
following solubilizers are used: urea, ethanol, n-propanol,
i-propanol, n-butanol, ethylene glycol and/or butyldi
glycol, propylene glycol, polyethylene glycol, lower and
higher molecular weight polyethylene-glycols [HO-(CHZ-CH2-
O)n-H] such as PEG-150, PEG-300, PEG-500, PEG-2000, PEG-3500
or PEG-8000, methoxy polyethylene glycols [CH3O-(CH2-CH2-O)n-
H] having an average molecular weight ranging from 150 to
5000, such as MPEG-350, MPEG-500, MPEG-750, MPEG-1000, MPEG-
2000, MPEG-3000 or MPEG-5000, vegetable oils, mixtures of
alkoxylated glycerides derived from carboxylic acids
containing between 6 and 22 carbons and alkoxylated glycerin
such as those commercially available under the trademark
LEVENOL 0 and marketed by KAO Chemicals Europe, alkoxylated,
preferably ethoxylated glycerol, etc., in an amount
corresponding to between 10 and 40 % by weight of one or
several of these solubilizing agents, relative to 100 parts
by weight of the total amount of the compounds a), b) c) and
d). These solubilizing agents are appropriate, in the context
of the present invention, provided that they do not reduce
the lubricant effect of the aqueous lubricant compositions.

The disinfectants that could be contained in the aqueous
lubricant compositions for conveyor systems are, for example,
those described in the "Gula de Plaguicidas utilizados en
Higiene Alimentaria y Salud Publica" published by the
Spanish Health Ministry (ISBN: 84-7607-499-2). Preferably,
according to the invention disinfectants should be used when
there is a risk of germs in the reserve tanks or on the
conveyor systems. These disinfectants or mixtures thereof
can be used in amounts of 5 to 50 parts by weight, relative
to 100 parts by weight the total amount of the compounds a),


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b) c) and d). A preferred disinfectant agent according to
the invention is chlorine dioxide (C102)

The subject matter of the present invention also
includes a process for lubricating conveyor systems
consisting in applying an aqueous lubricant diluted
composition according to the invention to a conveyor system

continuosly or at intervals.
The conveyor systems, which can be lubricated by the
process according to the invention, can be systems for glass
bottles, plastic bottles such as polyethylene terephtalate
(PET) or polycarbonate (PC) bottles, cans, glass containers,
drums, cardboard containers and similar items. Preferably,
the systems are suitable for glass bottles, polyethylene
terephtalate (PET) bottles, and cans.

The subject matter of the present invention also
includes the use of the aqueous diluted lubricant composition
according to the invention for lubricating conveyor systems.
Said conveyor systems can be systems for glass bottles,
plastic bottles such as polyethylene terephtalate (PET) or
polycarbonate (PC) bottles, cans, glass containers, drums,
cardboard containers and similar items. Preferably, the
systems are suitable for glass bottles, polyethylene
terephtalate (PET) bottles, and cans.

The following examples are given in order to pfovide a
person skilled in the art with a sufficiently clear and
complete explanation of the present invention, but should not
be considered as limiting of the essential aspects of its
subject, as set out in the preceding portions of this
description.


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Examples

Example 1. Aqueous lubricant compositions

The following aqueous lubricant compositions were
prepared. The values are referred to weight percentage.

Table 1. - Lubricant compositions according to the invention
(components as active matter)

1 2 3 4 5 6
Polyoxyethylene (3) 72.7 54.1 36.1 32.8 29.5 42.4
oleyl phosphate esterl

Polyoxyethylene (2)
oleyl ether carboxylic 10.4 22.0 33.7 30.7 27.6 39.6
acid2
Polyoxyethylene (5)
oleyl ether carboxylic 8.4 6.3 4.2 3.8 3.4 4.9
acid3
Polyoxyethylene (8)
capryl ether carboxylic --- --- --- 8.4 16.7 ---
acid4
Oleic Acid 4.6 9.7 14.8 13.4 12.1
Oleyl alcohol 2.7 5.8 8.8 8.1 7.3 10.3
Deionized water 1.8 2.1 2.4 2.9 3.4 2.8


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1Phosphoric ester of ethoxylated (3 EO) oleyl alcohol,
mono-ester to di-ester ratio 55:45
2Oleic ether carboxylic acid with an average
ethoxylation degree of 2
3Oleic ether carboxylic acid with an average
ethoxylation degree of 5
4Caprylic ether carboxylic acid with an average
ethoxylation degree of 8

Table 2. - Comparative Experiments (components as active
matter)

C1 C2 C3
Polyoxyethylene (3) oleyl 36.1 99.3 ---
phosphate esterl
Oleic Acid 14.8 --- ---
Oleyl alcohol 8.8 --- ---
Polyoxyethylene (1) oleyl --- 95.0
ether carboxylic acid 2

Sodium dodecyl 37.9
benzenesulf onate3
Deionized water 2.4 0.7 5.0
1Phosphoric ester of ethoxylated (3 EO) oleyl alcohol,
mono-ester to di-ester ratio 55:45

2Oleic ether carboxylic acid with an average
ethoxylation degree of 1

3As described in US-A-5062979


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Example 2. Lubrication in conveyor systems for glass
bottles.
Tests to measure friction resistance were performed on a
stainless steel bottle conveyor belt under the following
conditions:

- Measurement of the resistance of 7 beer bottles type Ale
0.5 L, filled with water, as a tensile force using a
dynamometer. These bottles are arranged in a plastic
crate for beer that permits their.rotation on the belt
but prevents them from toppling over.

- Speed of bottles: approximately 0.5 m/s.

- Continuous spraying of the bottle conveyor belt with a
lubricant solution of 0.03% by weight.

- Spraying volume of the nozzle: approximately 3.5 L/hour.
The dynamic friction coefficient ( ) is defined as the
coefficient between the tensile force measured for a bottle
and the weight of this bottle expressed in grams. This
coefficient is determined when a constant value is obtained.
Foam production is controlled visually. The compositions
according to the invention present no foam formation or
slightly foam formation.

Dilution of the lubricant compositions according to the
invention (Table 1 of Example 1) as well as the comparative
experiments (Table 2 of Example 1) was carried out with tap
water from Emmerich am Rhein (Germany), specifically of

hardness 17 dH (German degrees) according to the regulation
UNE-EN 12829.

Table 3 shows the friction coefficients obtained for the
lubricant compositions described in Table 1 and Table 2 of


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Example 1.

Table 3. - Friction coefficients for glass bottles ( )
Lubricant compositions

1 0.10
2 0.11
3 0.12
4 0.10
5 0.10
6 0.13
C1 0.16
C2 0.13
C3 0.16
C4* 0.17
* Commercial product based on:

- N-Oleyl-1,3-diaminopropane,

- C13 branched alcohol with average ethoxylation degree
of 8,

- Acetic acid and

- Oleic ether carboxylic acid with an average
ethoxylation degree of 9

Example 3. Lubrication in conveyor systems for PET
bottles.
Tests to measure friction resistance were performed on a
stainless steel bottle conveyor belt under the following
conditions:

- Measurement of the resistance of 6 PET bottles type
"weii3e Brunnen-Einheitsflaschen 0.5L" (Rostiprimpac),
filled with water, as a tensile force using a


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26
dynamometer. These bottles are arranged in a steel frame
for the PET bottles that permits their rotation on the
belt but prevents them from toppling over.

- Speed of bottles: approximately 0.5 m/s.

- Continuous spraying of the bottle conveyor belt with a
lubricant solution of 0.03% by weight.

- Spraying volume of the nozzle: approximately 3.5 L/hour.
The dynamic friction coefficient ( ) is defined as the
coefficient between the tensile force measured for a bottle
and the weight of this bottle expressed in grams. This
coefficient is determined when a constant value is obtained.
Foam production is controlled visually. The compositions
according to the invention present no foam formation or

slightly foam formation.

Dilution of the lubricant compositions according to the
invention (Table 1 of Example 1) as well as the comparative
experiments (Table 2 of Example 1) was carried out with tap
water from Emmerich am Rhein (Germany), specifically of

hardness 17 dH (German degrees) according to the regulation
UNE-EN 12829.

Table 4 shows the friction coefficients obtained for the
lubricant compositions described in Table 1 and Table 2 of
Example 1.


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Table 4. - Friction coefficients for PET bottles ( )

Lubricant compositions
1 0.15
2 0.13
3 0.13
4 0.11
0.13
6 0.16
C1 0.17
C2 0.20
C3 0.18
From the experimental results it can be shown that the

lubricant compositions according to the invention permit to
reduce the friction over the conveyor system (lower friction
coefficients) in comparison with the comparative experiments
both for glass bottles and for PET bottles.
Thus, more versatile lubricant compositions for conveyor
systems can be obtained.
Compositions 1 and 2 are particularly advantageous for
glass bottles.
Furthermore, Compositions 4 and 5, where the ether
carboxylic acid is a mixture of
I) Ca ether carboxylic acid having an average
ethoxylation degree of 8, and
II) oleyl ether carboxylic acid having an average
ethoxylation degree of 2, and
III) oleyl ether carboxylic acid having an average
ethoxylation degree of 5
are particularly advantageous for both glass and PET bottles.


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Example 4. Viscosity of the lubricant compositions for
conveyor systems.

Some of the aqueous lubricant compositions for conveyor
systems of Table 1 of Example 1 were slightly diluted to
obtain intermediate partially diluted compositions (8 % by
weight on active matter). Their viscosity at 20 C was
measured a Brookfield viscometer LVT (supplied by Brookfield
Engineering Laboratories Inc. Stoughton, MA, USA) in
accordance with DIN 1341 (spindle 2 at 30 rpm for viscosities
in the range of up to 1,000 mPa.s; spindle 3 at 12 rpm for
viscosities in the range of 1,000 to 7,000 mPa.s; spindle 4
at 12 rpm for viscosities in the range of more than 7,000
mPa.s)

Dilution of the lubricant compositions according to the
invention was carried out with tap water from Emmerich am
Rhein (Germany), specifically of hardness 17 dH (German
degrees) according to the regulation UNE-EN 12829.

Table 5. - Viscosity values (20 C)
Lubricant compositions Viscosity
(8 wt.% a.m.) (mPa.s)

1 5100
2 500
3 300
4 150
All the compositions were visually clear without

formation of any deposit, precipation or oil layer.
From the experimental results it can be concluded that
the aqueous lubricant compositions for conveyor systems
according to the invention are pumpable and homogeneous at


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29
room temperature. Furthermore, it has to be remarked that the
compositions where the ether carboxylic acid is a mixture of

I) C8 ether carboxylic acid having an average
ethoxylation degree of 8, and
II) oleyl ether carboxylic acid having an average
ethoxylation degree of 2, and
III) oleyl ether carboxylic acid having an average
ethoxylation degree of 5
are particularly advantageous f"rom the viscosity point of
view (better pumpability)


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Example 5 Other lubricant compositions according to the
invention

Table 6 - Other lubricant compositions according to the
invention (components as active matter)

7 8 9 10 11 12
Polyoxyethylene .(3) 30.0
--- --- --- --- ---
octanol phosphate esterl
Polyoxyethylene (2,5)
lauryl-myristyl --- 30.0 --- --- --- ---
phosphate ester2

Polyoxyethylene (2) 30.0 ---
--- --- --- ---
oleyl phosphate ester3

Polyoxyethylene (3) 30.0 -- - - -
oleyl phosphate ester' - - - - - - - - -

Polyoxyethylene (5) - - - - - - - - - - - - 30.0 - - -
oleyl phosphate ester5

Polyoxyethylene (9) 30.0
--- --- --- --- ---
oleyl phosphate ester6
Polyoxyethylene (2)
oleyl ether carboxylic 27.8 27.8 27.8 27.8 27.8 27.8
acid'
Polyoxyethylene (5)
oleyl ether carboxylic 3.5 3.5 3.5 3.5 3.5 3.5
acide
Polyoxyethylene (8)
capryl ether carboxylic 15.6 15.6 15.6 15.6 15.6 15.6
acid9
Oleic Acid 12.2 12.2 12.2 12.2 12.2 12.2
Oleyl alcohol 7.3 7.3 7.3 7.3 7.3 7.3
Deionized water Up to Up to Up to Up to Up to Up to
100 100 100 100 100 100


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'Phosphoric ester of ethoxylated (3 EO) octanol, mono-
ester to di-ester ratio 65:35

2Phosphoric ester of ethoxylated (2,5 EO) lauryl-
myristyl alcohol, mono-ester to di-ester ratio 60:40
3Phosphoric ester of ethoxylated (2 EO) oleyl alcohol,
mono-ester to di-ester ratio 60:40

4Phosphoric ester of ethoxylated (3 EO) oleyl alcohol,
mono-ester to di-ester ratio 67:33

5Phosphoric ester of ethoxylated (5 EO) oleyl alcohol,
mono-ester to di-ester ratio 60:40

6Phosphoric ester of ethoxylated (9 EO) oleyl alcohol,
mono-ester to di-ester ratio 65:35

'Oleic ether carboxylic acid with an average
ethoxylation degree of 2

8Oleic ether carboxylic acid with an average
ethoxylation degree of 5

9Caprylic ether carboxylic acid with an average
ethoxylation degree of 8


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Table 7 - Other lubricant compositions according to the

invention (components as active matter)

13 14 15 16 17 18
Lauryl-myristyl 30.0
--- --- --- --- --
phosphate esterl
Polyoxyethylene (12)
Lauryl-myristyl --- 30.0 --- ---
phosphate --- ---
ester 2
Cetyl phosphate ester3 --- --- 30.0 --- --- ---
Polyoxyethylene (12) 30.0 --- - - -
cetyl phosphate ester4 - - - - - - - - -

Oleyl phosphate ester5 --- --- --- --- 30.0 ---
Polyoxyethylene (5) --- 30.0
--- --- --- ---
oleyl phosphate ester6
Polyoxyethylene (2)
oleyl ether carboxylic 27.8 27.8 27.8 27.8 27.8 27.8
acid'
Polyoxyethylene (5)
oleyl ether carboxylic 3.5 3.5 3.5 3.5 3.5 3.5
acide
Polyoxyethylene (8)
capryl ether carboxylic 15.6 15.6 15.6 15.6 15.6 15.6
acid9
Oleic Acid 12.2 12.2 12.2 12.2 12.2 12.2
Oleyl alcohol 7.3 7.3 7.3 7.3 7.3 7.3
Deionized water Up to Up to Up to Up to Up to Up to
100 100 100 100 100 100


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1Lauryl-miristyl phosphate ester, mono-ester to di-ester
ratio 55:45

2Phosphoric ester of ethoxylated (12 EO) lauryl-miristyl
alcohol, mono-ester to di-ester ratio 67:33

3 Cetyl phosphate ester, mono-ester to di-ester ratio
67:33

4Phosphoric ester of ethoxylated (12 EO) cetyl alcohol,
mono-ester to di-ester ratio 67:33

501eyl phosphate ester, mono-ester to di-ester ratio
55:45

6Phosphoric ester of ethoxylated (12 EO) oleyl alcohol,
mono-ester to di-ester ratio 67:33

'Oleic ether carboxylic acid with an average
ethoxylation degree of 2

8 Oleic ether carboxylic acid with an average
ethoxylation degree of 5

9Caprylic ether carboxylic acid with an average
ethoxylation degree of 8


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Table 8- Other lubricant compositions according to the

invention (components as active matter)

19 20 21 22 23 24 25
Polyoxyethylene (3)
l 30.0 30.0 30.0 30.0 30.0 30.0 30:0
oleyl phosphate ester
Polyoxyethylene (2)
oleyl ether carboxylic 31.4 --- --- --- --- --- 27.8
acid2
Polyoxyethylene (5)
oleyl ether carboxylic --- 30.5 --- --- --- --- 3.5
acid3
Polyoxyethylene (9)
oleyl ether carboxylic --- --- 29.8 --- --- --- ---
acid4
Polyoxyethylene(2.5)
lauryl-miristyl ether --- --- --- 31.4 --- --- ---
carboxylic acid5
Polyoxyethylene (4.5)
lauryl-miristyl ether --- --- --- --- 30.5 --- ---
carboxylic acid6
Polyoxyethylene (3)
octyl ether carboxylic --- --- --- --- --- 30.8 ---
acid'
Polyoxyethylene (8)
capryl ether 15.6 15.6 15.6 15.6 15.6 15.6 ---
carboxylic acide
Polyoxyethylene (8)
capryl ether
carboxylic acid8+
--- --- --- - - --- -- 15.6
Polyoxyethylene (3)
hexyl ether carboxylic
acid9
Oleic Acid 12.2 12.2 12.2 12.2 12.2 12.2 12.2
Oleyl alcohol 7.3 7.3 7.3 7.3 7.3 7.3 7.3
Deionized water Up to Up to Up to Up to Up to Up to Up to
100 100 100 100 100 100 100


CA 02645226 2008-09-09
WO 2007/112917 PCT/EP2007/002772
1Phosphoric ester of ethoxylated (3 EO) oleyl alcohol,
mono-ester to di-ester ratio 55:45

20leic ether carboxylic acid with an average
ethoxylation degree of 2

30leic ether carboxylic acid with an average
ethoxylation degree of 5

40leic ether carboxylic acid with an average
ethoxylation degree of 9

5Lauryl-miristyl ether carboxylic acid with an average
ethoxylation degree of 2.5

6Lauryl-miristyl ether carboxylic acid with an average
ethoxylation degree of 4.5

'Octyl ether carboxylic acid with an average
ethoxylation degree of 3

8Caprylic ether carboxylic acid with an average
ethoxylation degree of 8

9Hexyl ether carboxylic acid with an average
ethoxylation degree of 3


CA 02645226 2008-09-09
WO 2007/112917 PCT/EP2007/002772
36
Table 9 - Other lubricant compositions according to the

invention (components as active matter)

26 27 28 29 30 31 32
Polyoxyethylene (3)
i 30.0 30.0 30.0 30.0 30.0 30.0 30.0
oleyl phosphate ester
Polyoxyethylene (2)
oleyl ether carboxylic 27.8 27.8 27.8 27.8 --- --- ---
acid2
Polyoxyethylene (5)
oleyl ether carboxylic 3.5 3.5 3.5 3.5 --- --- ---
acid3
Polyoxyethylene (8)
capryl ether 15.6 15.6 15.6 15.6 15.6 15.6 15.6
carboxylic acid4
Oleic acid --- --- 12.2 12.2 12.2 12.2 12.2
Coco fatty acid 12.2 --- --- --- --- --- ---
Tall oil fatty acid --- 12.2 --- --- --- --- ---
Oleyl alcohol 7.3 7.3 --- --- 7.3 7.3 7.3
Lauryl alcohol --- --- 7.3 --- --- --- ---
Octanol --- --- --- 7.3 --- --- ---
Polyoxyethylene (2)
--- --- --- --- 33.1 --- ---
oleyl alcohol ether5
Polyoxyethylene (5)
--- --- --- --- --- 33.1 oleyl alcohol ether6

Polyoxyethylene (9)
--- --- --- --- --- --- 33.1
oleyl alcohol ether'

Deionized water Up to Up to Up ta Up to Up to Up to Up to
100 100 100 100 100 100 100


CA 02645226 2008-09-09
WO 2007/112917 PCT/EP2007/002772
37
1Phosphoric ester of ethoxylated (3 EO) oleyl alcohol,
mono-ester to di-ester ratio 55:45

2Oleic ether carboxylic acid with an average
ethoxylation degree of 2

30leic ether carboxylic acid with an average
ethoxylation degree of 5

4Caprylic ether carboxylic acid with an average
ethoxylation degree of 8

5Ethoxylated oleyl alcohol with an average ethoxylation
degree of 2

6Ethoxylated oleyl alcohol with an average ethoxylation
degree of 5

'Ethoxylated oleyl alcohol with an average ethoxylation
degree of 9


CA 02645226 2008-09-09
WO 2007/112917 PCT/EP2007/002772
38
Example 6. Lubricant compositions described in US-A-
4895668

A lubricant composition as described in US 4 895 668
(composition C5) and a similar lubricant composition, but
containing phosphate ester and fatty alcohol (Example 33)
were prepared. Their compositions are shown in Table 10. The
values refer to weight percentages (components as active
matter).

Table 10

C5 33
Xylene sulphonic acid,
sodium salt (30o aq. 13.00 13.00
solution)

EDTA tetrasodium salt 20.00 20.00
(30% aq. solution)

Nonyl phenol ethoxylated 5.00 ---
(9 EO)
Iso-propanol 10.00 10.00
Linear alkylbenzene 4.25 4.25
sulphonic acid
Sodium polyoxyethylene
(4) oleyl ether 5.00 3.75
carboxylatel
Monoethanolamine 5.40 5.40
Tall oil fatty acid 20.00 20.00
Polyoxyethylene (3) --- 1.25
oleyl phosphate ester2

Lauryl alcohol --- 5.00
ethoxylated (9 EO)
Deionized water 17.35 17.35


CA 02645226 2008-09-09
WO 2007/112917 PCT/EP2007/002772
39
1Sodium oleic ether carboxylate with an average
ethoxylation degree of 4

1Phosphoric ester of ethoxylated (3 EO) oleyl alcohol,
mono-ester to di-ester ratio 55:45

The dynamic friction coefficient ( ) for glass bottles
and for PET bottles for the above-indicated compositions was
measured following the methods described in Examples 2 and 3.
The results are indicated in Table 11.

Table 11. - Friction coefficients for PET and glass bottles
( )

Lubricant compositions F~ !l
Glass PET
33 0.14 0.16
C5 0.17 0.18

These results show that the composition of the present
invention is superior to the one of US 4 895 668 in terms of
lubrication for both glass and PET bottles.

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 2007-03-28
(87) PCT Publication Date 2007-10-11
(85) National Entry 2008-09-09
Examination Requested 2012-02-07
Dead Application 2015-03-30

Abandonment History

Abandonment Date Reason Reinstatement Date
2012-03-28 FAILURE TO PAY APPLICATION MAINTENANCE FEE 2012-04-23
2014-03-28 FAILURE TO PAY APPLICATION MAINTENANCE FEE
2014-05-22 R30(2) - Failure to Respond

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $400.00 2008-09-09
Maintenance Fee - Application - New Act 2 2009-03-30 $100.00 2009-03-13
Maintenance Fee - Application - New Act 3 2010-03-29 $100.00 2010-03-22
Maintenance Fee - Application - New Act 4 2011-03-28 $100.00 2011-02-03
Request for Examination $800.00 2012-02-07
Reinstatement: Failure to Pay Application Maintenance Fees $200.00 2012-04-23
Maintenance Fee - Application - New Act 5 2012-03-28 $200.00 2012-04-23
Maintenance Fee - Application - New Act 6 2013-03-28 $200.00 2013-02-25
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
KAO CHEMICALS GMBH
Past Owners on Record
DE RIJK, BEN
MEIJER, HAMKE
VIERBAUM, MELANIE
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Abstract 2008-09-09 1 65
Claims 2008-09-09 5 200
Description 2008-09-09 39 1,226
Cover Page 2009-01-15 1 36
Abstract 2013-07-16 1 22
Description 2013-07-16 40 1,236
Claims 2013-07-16 5 111
Abstract 2013-08-06 1 22
Description 2013-08-06 40 1,237
PCT 2008-09-09 16 500
Assignment 2008-09-09 3 88
Correspondence 2009-01-08 1 24
Correspondence 2010-02-12 1 17
Correspondence 2010-03-04 3 76
Prosecution-Amendment 2012-02-07 1 38
Fees 2012-04-23 1 163
Prosecution-Amendment 2013-01-22 4 181
Prosecution-Amendment 2013-07-16 14 377
Prosecution-Amendment 2013-08-06 7 223
Prosecution-Amendment 2013-11-22 2 87