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Patent 2096077 Summary

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(12) Patent Application: (11) CA 2096077
(54) English Title: NITROGEN-FREE ACTIVE INGREDIENT COMPONENT IN FABRIC SOFTENER FORMULATIONS
(54) French Title: INGREDIENT ACTIF NON AZOTE, EN TANT QUE PARTIE COMPOSANTE DE FORMULATIONS D'ASSOUPLISSEUR
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • D06M 13/207 (2006.01)
  • C11D 1/74 (2006.01)
  • C11D 1/835 (2006.01)
  • C11D 3/00 (2006.01)
  • C11D 10/04 (2006.01)
  • D06M 13/10 (2006.01)
  • C11D 1/62 (2006.01)
(72) Inventors :
  • BROCK, MICHAEL (Germany)
  • HARDT, PETER (Germany)
  • KLIMMEK, HELMUT (Germany)
  • STOCKHAUSEN, DOLF (Germany)
(73) Owners :
  • HULS AKTIENGESELLSCHAFT (Germany)
(71) Applicants :
(74) Agent: FETHERSTONHAUGH & CO.
(74) Associate agent:
(45) Issued:
(22) Filed Date: 1993-05-12
(41) Open to Public Inspection: 1993-11-15
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
P 42 15 689.0 Germany 1992-05-14

Abstracts

English Abstract




Abstract:

The invention relates to nitrogen-free active ingredient
components in fabric softener formulations and to the use
thereof.

The nitrogen-containing cationic fabric softener active
ingredient components used hitherto often have an
unfavourable aquatic toxicity and are undesirable in view
of the possibility of nitrosamine formation. A novel,
nitrogen-free fabric softener active ingredient component
is therefore proposed. It comprises alkoxylated natural
fats or oils and may be used on its own or in combination
with conventional cationic nitrogen-containing active
ingredient components with and without the addition of
dispersants, emulsifiers and/or solubilisers. A
synergistic increase in effect is obtained in some cases.
A nitrogen-free or low-nitrogen fabric softener
formulation with a high softening potential, i.e. good
antistatic and rewetting properties, may thus be prepared.


Claims

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



Patent claims

1. Nitrogen-free active ingredient component for fabric
softener formulations comprising alkoxylated natural
fats, oils and mixtures thereof with free fatty
acids, mono- and/or diglycerides.

2. Nitrogen-free active ingredient component according
to Claim 1, characterised in that one or more
alkoxylating agents are used for the alkoxylation of
the natural fats, oils and mixtures thereof with free
fatty acids, mono- and/or diglycerides, and the
addition thereof takes place simultaneously or
successively.

3. Nitrogen-free active ingredient component according
to Claim 1, characterised in that mixtures of various
alkoxylated natural fats, oils and mixtures thereof
with free fatty acids, mono- and/or diglycerides are
used.

4. Nitrogen-free active ingredient component according
to Claim 1, characterised in that the mixing of
various natural fats, oils and mixtures thereof with
free fatty acids, mono- and/or diglycerides takes
place prior to alkoxylation.

5. Use of alkoxylated natural fats, oils and mixtures
thereof with free fatty acids, mono- and/or
diglycerides according to Claim 1 on their own as
nitrogen-free fabric softener active ingredient
component or in mixtures with nitrogen-containing
cationic fabric softener active ingredient components
and, if necessary, dispersants, emulsifiers and/or
solubilisers.

6. Use according to Claim 5, characterised in that the
proportion of alkoxylated natural fats, oils and
mixtures thereof with free fatty acids, mono- and/or


diglycerides is 1 to 100%, preferably 20 to 80%, of
the total quantity of fabric softener active
ingredient.

7. Use according to Claim 5, characterised in that the
cationic nitrogen-containing fabric softener active
ingredient component is N,N-distearyl-N,N-dimethyl-
ammonium salts, quaternised or protonated imida-
zolines, quaternised fatty acid esters of tri-
ethanolamine and 2,3-dihydroxypropyl-1-trimethyl-
ammonium salt derivatives or mixtures thereof.

8. Use according to Claim 5, characterised in that the
proportion of cationic nitrogen-containing fabric
softener active ingredients and mixtures thereof is
0 to 99%, preferably 20 to 80%, of the total quantity
of fabric softener active ingredient.

9. Use according to Claim 5, characterised in that the
dispersants, emulsifiers and/or solubilisers used are
anionic surfactants, nonionic surfactants, cationic
surfactants, solvents, ampholytes, betaines, metal
soaps or mixtures thereof.

10. Use according to Claims 5 and 9, characterised in
that the dispersants, emulsifiers and/or solubilisers
used are alkylpolyglycosides, alkoxylated natural
fats, oils and mixtures thereof with free fatty
acids, mono- and/or diglycerides.

11. Use according to Claim 5, characterised in that the
ratio of dispersants, emulsifiers and/or solubilisers
to the total quantity of fabric softener active
ingredient is 0 to 10:1.

Description

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


2~9~ 7
Hul~ Ak$iengesellschaft ~ O.Z. 4656
Patent ~epartment
Nitroqen-free active ingredient com~onent in fabric
softener formulation~

The invention relates to alkoxylated natural oils and fat~
as ni~rogen-free active ingredient component in ~abric
softener formulations and to their us9 therefor. The
alkoxylated natural oils and fat~ may be u~ad both on
their own and in mixtura with conventional nitrogen-
containing cationic active ingredient components with and
without the addition of disper~ants, emulsifiers and/or
- solubiliser~.

It is known to use nitrogen-containing cationic compou~d~
a~ the sole active ingredient components ln fabric
softener formulation~. The active ingredient N,N-
distearyl-N~N-dimethylammonium chloride (VSDMAC~ u~ed over
many years in fabxic softener~ is, however, increa~ingly
being replaced, on account of its unfavourable aqua-
toxicity, by ~ubstitutes e.g., imidazoline derivative~
(see inter alia, ~uch a~, for example, US-A 4 762 685,
EP-A 0 199 383), quaternised fatty acid ester~ of
triethanolamine ~known as esterquats, see inter alia
US-A 4 830 771) or 2,3-dihydroxypropyl-1-trimethyl-
ammonium ~alt deri~atives (DE-A 27 28 841).
In the medium and long term, it is likely that nitrogen-
contaLning fabric softener active ingredient component~
will have to be replaced partially or completely by
largely nitrogen-free alternatives, inter alia, in YieW of
the possibility of nitrosamine formation. Said alter-
natives should be characterised by a high softening
potential, anti~tatic and rewetting properties and
advantageous ecotoxicological behaviour. DE-A 34 16 669
describes the use of crystalline layer silicates and
alkaline salts thereof as softening active ingredients in
detergents. A sLmLlar situation is described in
DE-A 23 34 899 and DE-A 33 12 774, which claim the u~e
of saponites, hectorites and montmorillonites as softenLng


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2 O.Z. 4656
active ingredients in detergents. Tha ~oft~ning ~ffact of
said substances is evidently based on their function as
cation exchangers and thu~ as water softeners. In ~oft
water, therefore, ~aid ~ubstance~ are ineffective.




The ob~ect of the invention i~ therefore to find nitrogen-
free active ingredient component~ which may be used a~ an
al~ernative to the ~ole use of nitrogen-containing fabric
~oftener active ingredient component~ or in combination
with ~aid components, if necessary after appropriate
emulsiflcation or di~persion and/or the addition of
solubili~ers. They should not only be miscible and
compatible with said suh~tances but al~o h~ve a
synergi~tlc effect, if po~sible, or alternatively exhibit
~often~ng propertie~ on their own.

The ob~ect 1~ achieved according to the invention by the
u~e of alkoxylated natural o~l~ and fats a~ nitrogen-frea
active ingredient component~ In principle, the oils and
fats which can be u~ed according to the invention as
starting material include all tri~lyceride~ and mixture~
thereof with free fatty acids/ mono- and/or diglycerides.
Alkoxylation may taXe plsce in accordance wlth
DE-A 36 17 657 and DE-~ 38 26 179.
The invention therefore relate~ to a nitrogen-free active
ingredient component for fabric ~oftener formulation~,
comprising alkoxylated natural fat~, oils and mix~urss
thereof with frea fatty acids, mono- and~or diglycerides.
The invention furthermoxe relates to the use of
alkoxylated natural fats, oils and mixtures thereof with
free fatty acids, mono- and/or diglycerides on their own
as nitrogen-free fabric softener active ingredient
component or in mixture~ with nitrogen-containing cationic
fabric softener active ingredient components and, if
nece~sary, dl~persants, emulsifiers and/or solubilisers.

The proportion of alkoxylated natural fats, oil8 and



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2~0~ o.z. 4~56
mixture~ thereof with free fatty acids, mono- and/or
diglycerides as fabric ~oftener active ingredisnt
component i~ 1 to 100%, preferably 20 to 80~, of the total
quantity of fabric softener active ingredient.




Mixtures of variou~ alkoxylated natur~l ats t oils and
mixture~ thereof with free fatty acids and/or mono- snd/or
diglycerides may al~o be used.

Moreover, the mixing of various natural fats, oil~ and
mix~ure~ thereof with free fatty acids, mono- and/or
diglycerld2~ may al80 take place prior to alkoxylation.

The following epoxides that can be used for alkoxylation
are mentio~ed by way of examples
Ethylene o~ide, propylene oxide, butylene oxideJ 2 methyl-
but-2-ene oxide, 3,3-dimethylbut-1-ene oxide, C6-C2,-
epoxides, styrene oxide, 1,2-epoxybutadiene~ 1,2-epoxy-
cyclohexene and glycidic ester3 and ether~. If more than
one epoxide i~ used, said epoxide~ may be reacted with the
fatty substances either successively or simultaneou~ly.

The proportion of cationic ni.trogen-containing fabric
softener active ingredients and mixtures thereof as fabric
2S softener actiYs ingredient component is 0 to 99~, prefer-
ably 20 to 80%, ba~ed on the total quantity of fabric
softener activs ingredien~.

~he following are mentioned by way of example a~ cationic
nitrogen-containing fabric ~oftener active ingredient
component~: NIN-distearyl-N,N-dimethylammonium 8alt8
imidazoline derivative~ (quatarnised or protonatsd),
quaternised fatty acid esters of triethanolamina and 2,3-
dihydroxypropyl-l-trimethylammonium salt derivatives.
Both the alkoxylated natural oils and fats on their own
and mlxtures thereof with the cationic nitrogen-containing
fabric softener active ingredient component~ may be used
for a further lncrea~e in effect, if nece~ary with
di~persant~, emul~ifiers and/or solubiliflera.


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2Q~ 7 o.z. 4656
The ratio of di~persant6, emul~ifiers and~or solub11iser~
or mixtures thereof to the fabric ~oftener active
ingredien~ component~ mentioned iB O to 10:1.

Apart from the fabric softener active ingredient
component~ and, if nece~ary, dispersant~, emul~ffier~
and/or solublll~ers or mLxture~ thereof, other additives,
such as, for example, fragrance~, dyes, visco~ity
regulator~ and water, may be added.
~s ha3 been found, even only 0.3 to 0.4 g of the
alkoxylated oil5 and fat~ per litre of rinsing liguor used
cau3e~ 8ignificant ~oftening in compari~on with terry
towel~ not treated with 90ftener. If the recommended
added quantitie~ of softener~ are adhered to and converted
: to the amount of water required in one washing machine
rinsing cycle, the re~ult i~ ~u5t such a quantity of
approx. 0.3 g of active substancQ per litra of rin~ing
l~quor, if the active content of the softener i~ known.
If customary nitrogen-containing fabric softener active
ingredient components or softener formulations ~re mixed
with the alkoxylated oils and fats, it become~ apparent
that, in ~ome ca~e8 up to a mixing ratio of ~ s 1 with an
unchanged total concentration of 0.35 g~l, the softenlng
effect remains the same or even Lmproves in compari~on
with the pure nltrogen-containing fabric softener activa
ingredient components or ~oftener formulations. Said
mixture~ have the advantage of havin~ a substantially
lowar nitrogen content with the same performance profile.
Even smaller proportion6 of the cu~tomary fabric ~oftener
active ingredient components or softener formulations may
be u~ed if conventional emulsifiers, disper~ants and/or
~olubili~er~ are added. The proportion of the customary
nitrogen-containing fabric softener active ingredient
component~ or fabric softener formulations needed to
obtain the softening effact may thu~ be reduced to as low
a~ 0%.



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2~9~ 7
5 O.Z. 46S6
Conventional emulsifiers, dispersants and solubili~ers
that may be used according to the invention are, ~or
example, those mentioned in "Encyclopedia of Emulsion
~echnology' Vol. 1 - 3, 1983, New York, and all mixtures
thereof. The following may be mentioned by way of
examples

(13 from the group of anionic ~urfactan~s:
sulphate~, sulphonatesl alkoxylated sulphates,
alkoxylated sulphonates, carboxylate~, alkoxylated
carboxylates, pho~phates and alkoxylated pho~phatea;

(2) from the group of nonionlc ~urfactantR:
fatty alcohol alkoxylate~, arylalkoxylate~,
alkoxylated oils and fats, amines, amides,
alkoxylated amine~, alkoxylated amides and am~na
oxide~;

(3) from the group of cationic surfactantss
cetylpyridinium chloride and bromide and the
nitrogen-containing fabric softener actlve ingredient
components already mentioned;

(4~ fr~m the group of ~olubil~sers:
l~opropanol, ethanol, ethylene glycol~, p~opylene
glycols, butyl glycol~;

(5) ampholytes and betaine~

(6) metal ~oap~

and additionally alkyl polyglyco~ides and the alkoxylated
oils and fat~ them~elves.




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6 O.Z. 4656
Descript~ion of the softenin~g efect test m_thod [triangle

The softening effect of the alkoxylated fat~, oils or
mixtures thereof with free fatty acid~ and/or mono- and/or
diglyceride~ or mixture~ thereof with cu~tomary fa~ric
~oftener active ingredient components was determined as
follows. a load of 72 terry towel~ (44 cm x 30 cm,
approx. 60 g, from WFX Te~tgewebe GmbH) wers washed once
by machine at 95 C with 100 g of a commercial heavy duty
d~tergent (PERSIL, Henkel), even if not all 72 towel~ ware
u~ed (for rea~on~ of uniform wear and tear), rinsed and
spun. ~here followed a wash cycle at 95 ~C without
deter~ent lncluding a rin~e and ~hort epin, ~o that clean,
damp towel~ containing about 2.5 time~ the~r dry weight of
water could be removed for manual ~oftening.

For a test plan as in Table A, in each ca~e 9 towel~ were
xin6ed in 9 rinsing liguor~ with the standard ~= S) and 9
towels were rineed in 9 rin3ing liquor~ with the test
substance (= T). To thi~ end, in each case 2 litre~ of
tap water and 0.00 or 0.35 g/l tandard (calc~lated a~
active substance) or a freely chosen amount of te~t
substance were predisper~ed in plastic bowl# and the damp
towels were left therein for 10 min. After 5 minutes the
towel~ were turned once. The rinsed towels were each spun
individually for 30 seconds and dried on the laundry
: stand~ in still air.
'~
- ~able A~ Te~t plan for the sensory ~oft feel test with 6
testers.
--~=. = ~
Tester Towel combination with keyed marking


~ SST
STT

6 STT
, = comparat: .ve subst~nce (st ~ test
substance)


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7 O.Z. 4656


In each case, 3 towal~ in keyed form were placed before
the tes~ pPr~ons in accordance with the tes~ plan
according to Ta~le A ( triangle test). The tester~ ta~k
was to pick out the differently treated towel by ~en~ory
apprai~al.

If this was pos~.Lble, the tester noted down whether the
different towel felt ~ofter or hsrder. If at least 5 of
the 6 testers picked out the differently treated towel (T
in the case of testers 1 to 3, S in the case of te ter~ 4
to 6), there i~ a significant difference between the test
subs~ance and the standard according to DIN 10 951 with a
probability of mors than 95%. The result $8 expre~sed
: with the a~d of 3 figure~: the fir6t figure gives the
number of te~ter~ who found the towels treated with the
standard ~ofter or found those treated with tha te~t
substance hardex. The second f.igure give~ the nu~ber of
testers who found the towels treated with the ~t~ndard
harder or found ~hose treated with the test ~ubs~ance
softer. Finally, the third f.igure gives the number of
testers who, in view of the ~mall sensory differences
between the towels treated with the test substance or the
standard, were unable to determi.ne the differently treated
towel or did not give the correct an~wer.

Example 1: .
: Towel~ treated with 0.2 - O.S g of the product of the
- 30 reaction of sk~n grease with 10% by wt. of othylene oxlde
and lOS by wt. oi propylene o~ida per litre of rinsing
liquor were te~ted in comparison with towels that had not
been treatad with a softener. The result i~ summari~ed
in Table 1.

~.



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2~9~Q~!7 o.z. ~65~
Table 1:
, ~ ~ _
Concentration [g/l] Triangle te~t Sample no.
__ . ~
0.2 1 : ~ s 5
0.3 0 s 4 s 2 2
0.4 0 s 5 s 1 3
0.5 0 ~ 5 s 1 4
, . ,, , _-- _. "~ . ~
Upward~ of a concentration of 0.4 g of the tes~ ~ubstanca
per litre of rinsing liquor, a signiicant difference in
the softne~ in favour of the towels treated with tha te~t
substance can thus be established in comparison with
untrea~ed towel~.

Exampl~ 2i
Towels treated with 0.2 - 0.5 g of the product of the
reaction of skin grea~e wlth 15~ by wt. of propylene o~ids
per litre of rinsing liquor were tested in comparison with
towels that had not been treated with a softener, The
result i~ summarised in Table 2.
Table 2
~,
Concen~ration [g~l] Triangle test Sample noO
_
0 ~ 3 0 3 3 6
O~q~ 0 2 5 ~ 1 7
- ~ ~ 6 ~ O _=_

Upwards of a concentration of 0.4 g of the te~t sub~tance
per litre of rinsing liquor, a siqnificant difference in
the softnes3 in favour of the towel~ treated wi~h the test
substance can thu4 be e~tabli~hed in compari~on with
untreated towels.

Example 3
Towels treated with 0.2 - 0.5 g of the product of the
reaction of palm oil with 15~ by wt. of propylene o~lde
per litre of rinsing liquor were tested in comparison with



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2~9~7 o.z. ~656
towels that had not been treated with a ~oftener. The
result i~ summarised in Table 3.

Table 3~
_ ~
¦Concentration [g/l] Triangle te~t Sample no.
0.2 1 : 0 a 5 9
0.3 ~ : 5 : ~ 10
0.4 0 : 6 : 0 1l
0.5 0 . 6 : 0 12

Upward~ of a concentration of 0.~ g/l of the te~t
substance, a ~ignificant di~ference in the softness in
favour of the towels treated with the test substance can
thus be e~tablished in comparison with untreated towels.
Example 4
Towel~ treated with ~i~ture~ of the product of the
reaction of lard oil with 15~ by wt~ of propylene oxide
with a customary qua~e~nised fatty acid e~ter oi
~ri~thanolamine (e~terquat, STEPANTEX VR 85, Stepan) of
varying ~omposition ~constant total concentratlon: 0.35 g
per litre of rinsing liquor) were tested in comparison
with towelR that had been txeated only with th2 customary
esterquat (constant concentration: likewise 0.35 g per
: 25 litre of rinsing li~uor), The re~ult i~ summarised in
Table 4.

Table 4 t
~ - -- . , .. .,, ~ l
Mixing ratio (~ by wt.)
30 Test Triangle Sample
~ub~ taDce Esterquat test no.
0 100 0 : 0 : 6 13
0 : 0 : 6 14
0 : 0 : 6 1
0 : 1 : 5 16
0 : 1 : 5 17
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O.Z. 4656
It i~, ther~fore, pos~ible to limit the amount of
esterquat to 30% by wt. without los~ of soft feel, and to
make up the deficient amount with the test sub0tance (see
sample no. 17).




Example Ss
Towels treated with mi~tures of the product of the
reaction of ~kin fat with 15 % by wt. of propylene o~lde
with a customary esterquat o~ ~arying compo~ition
(con3tant total concentration. 0.35 g per litre of rinsing
liquor) were tested in comparison with towel~ that had
been treated only with the customary e~terquat (con~tant
concentration; likewise 0.35 g per litre of rin~lng
liquor). The result i8 summarised in Table 5.
Table 5
_ . z~. ~ .
Mixing ratLo (~ by wt.)
Test Triangle 5ample
: substance Esterquat test no.
2 0 _ . 10 0 0 1) a 6 18
0 2 4 19
41D 60 0 1 s 5 2~
4() 1 0 5 21
~ . -- 2 0 4 22

The result i~ ~imilar to that o~ Ex~mple 4 (~ee sample no.
; 21).

Example 6:
Towela treated with mi~tures of the product of the
reac~ion of ~kin fat with 15% by wt. o~ propylene oxide
with a customa~y softener 1 containing the ditallo~ fatt~
acid ester of 2,3-dihydro~ypropyl-1-trimethylammon~um
chloride (ROBIJN softener, Unilever), of varying
composition (con~tant total concentration: 0.35 g per
litre of rlnsing liquor) were te~ted in compari~on wi~h
towels that had been treated only with 1 (constant
concentration: likewise 0.35 g per litr~ o~ rinsing


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11 O. Z . 4656
liquor). The re~ult i8 sununarised in Table 6.

Tahle 6-
~ .,.. = ~
Mixing ratio (% by ~t. )
Test ~riangle Sample
sub4tance 1 test no .
_ _ .
0 100 0 : 0 s 6 23
1 : 0 s 5 24
~ 0 : 5 : 1 25
0 : 5 s 1 26
0 : 0 s 6 27
.~ . - __ ~ .
With the aid of the tast ~ubstance it i~ even po sible to
significantly improve the ~oftening properties i~ 40 to
60~ by wt. of the test substance are added to 1 (~ee
sample nos. 25 and 26). If a test ~ub~tance~l (4:1)
mixture is used, the softening propertie~ are the same as
those of pure 1 ~see ~ample no. 27~.

Example 7:
Towels treated with mi2ture~ of the product of the
reaction of palm oil with 15% by wt. of propylene o~ide
with a cu~tomary ~oftener 1 containing the ditall~w fa~ty
acid e8ter of 2,3~dihydro~ypropyl-1-trLme~hylammoni~
chloride, of varying composition (const~nt total
concentration: 0.35 g per litre of rinsing liquor) were
te~ted in comparl~on with towels that had been treated
only with 1 tconstant concentration: likewi6e 0.~5 g per
litre of rin~ing liquor). The result i~ ~ummarised in
Table 7.




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2 ~ 0 '7 ~
12 O.Z. 4656
Table 7~
. ~ -~ ~
Mixing ratio (% by wt.~
Te~t Triangle Sample
substance 1 test no.
_ . ...
O 100 O s O s 6 28
2 : 1 : 3 29
1 : O s 5 30
~0 1 : 1 : 4 31
_ . . _ _ ~ 4 32
The result is similar to that of Example 4 (see ~ample no.
32).

: Example ~s
Towel~ treated with mi~ure~ of the product of the
reaction of skin fat with 15~ by ~t. of propylene o~ide
with l-met~yl-2-~lkyl-3-alkylamido-ethylLmida~olin~um
methosulphate 2 (MARLOSOFT IQ 90, H~l~) of varying
composition (con~tant total concentration: 0,35 g per
litre of rin~ing liquor) were testPd in compari~on wlth
tow918 that had been treated only with 2 (con~tant
concentration: 0.35 g per litre of rin~ing liquor). The
: result i8 summar$sed in Table 8.

~able 8s
, . .~ . ._ ~
Mlxing ratio (% by wt.~
Test Triangle Sample
substance 2 te~t . no.
. .. . __ _ _ _ _ _ .,
O 100 O : O : 6 33
30 20 80 O : 1 : 5 34
O : 4 : 2 35
O s 2 : 4 36
~0 1 : 1 : 4 37
-- -- ~ . ~K=~ ___
The test substance can be mixed with 2 ln all the mixtures
examined, the soft feal of the treated towels not being
impaired, and even improving in some caseR (Ree sample


- "
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, . . . . ...
,

~0~3~n77
13 O.Z. 4656
nos. 34 - 36).

Example 9:
Towel~ treated with mixtures of the product of the
reaction of skin fat with 15~ by wt. o~ propylene o~ide
with a cu~tomary ~oftener 3 containing the protonated 2-
alkyl-3-o~oacylalkyl-ethylimidazoline salt of acstic acid
or lactic acid (LENOR, Procter & Gamble), of varying
compo~ition (constant total concentrationt 0.35 g per
litre of rin3ing liquor) were tested in compari~on with
towel~ that had been treated only with 3 ( constant
concentration: likewi~e 0.35 g per litre of rinsing
liquor~. ~he re~ult 1~ summarised in Table 9.

: 15 Table ~. -
.... ~ .. _ _ . . ~
: Mixing ratio (% by wt.)
Te~t Triangle Sample
: substance ~ te~t no.
: 0 100 0 : 0 ~ 6 38
0 . 1 : 5 39
~0 60 0 : 1 s 5 40
1 ~ 0 ~ 5 41
: 80 20 1 : 0 : 5 42
~ ~ - ~ ~
The test ~ubstance can be mixed with 3 in all tha ratio~
~xamined, the ~oft feel of the treated towels remaining
the sa~e.

Example 10:
Towels treated with ~istures of the product of the
reaction of palm oil with 15~ by wt. of propyl~e o~ide
with the came fioftener 3 as in Example 9 of varying
composition ~constant total concentrations 0.35 g per
litre of rinsing liquor) were tested in compari~on with
towels that had been treated only with 3 (constant
: conaentrations likewise 0.35 g per litre of rinsing
liquor)~ ~he result i8 ~ummarised in Table 10~



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21~49 ~ O.Z. 4656
Table lOs
I ~ ~ __ ~
Mixing ratio (~ by wt.~
Test ~rriangle Sample
~ubstance 3 test no.
__ _ .. . _ _ . , _ _
0 100 0 s 0 : 6 43
1 s 1 ~ 4 44
1 ~ 1 : 4 45
~0 ~0 1 : 1 ~ 4 46
_ . _ _ _ _ 0 ~ 1 : 5 47
1~
It i8, therefore, pos~ible to limit the amount of 3 to
30 % by wt. withou~ 108~ of the soft feel, and to make up
:~: the deficient amount with the test ~ubstance ~see sample
no. 47).
Examination of the rew*tt n~ prop~rty
In accordance with DIN 53 924 (ri~e in height method),
rewetting te~ts were carri~d out in a simplified form on
; terry fabricO To this end, terry towels were treated with
the test substances in accordance with the method
described in the section "Description of the softening
ef fec~ test method" . After drying, strips 30 cm long and
8 cm wide were cut (in a crosswise direction) and
suspended vertically ~n a beaker filled with 500 ml of
25 deionised water. The depth of immer~ion of tha fabric wa~
1 cm.

In order to make the rise in height more discernible,
0.5 g of K2CrO~ was added to the water. The immer~ion time
was 5 minutes in each case. The water wa~ then removed
and the ris2 in height reached was m~a~ured. The rise in
height that followed without further addition of water wa~
mea~ured after 65 minutes.

The rise~ in height ascertained in respect of the terry
fabric treated with samples 1 - 47 from Example~ 1 - 10
are listed in Table 11. They are means of double
determinations.



.

- . .
, . : ;
~ , . , , , ~.


77 o.z. 4656
Table_11 s Rise~ in height found for terry fabric treated
with ~ample~ 1 - 47 from Examples 1 - 10.
I . .. . _
Example no. Sample no. ri~e in height [Cml
_ _ after 5 min. after 65 min.
1 O ample 10 . 2 18 . 5
. __
1 1 10.4 18.9
. . .. . _ .. . __ _____
1 2 10 . 0 18 .5
1_ _ . _ 17.2---
1 4 9.S 17.8
~ - ! --. _ ___ _ = __ _ __ _
2 5 10 . 4 19 .5
, .. . ~ , ~ ~ .
2 6 8 . 8 16 . 5
- . . _ _ ~I
2 7 9.5 16.3
~ _ . ..... ~ . . _ _ _
2 ~ îQ.5 17.8
~ ~ _~ _ . . _.- - . .
3 9 10.3 18.4
_ . . . -----~i
3 10 8.9 1~.0
3 11 9.0 15.9
: ~ ~ _ __ I_____~
3 12 8.9 15.1
. --,- --.-----,,. ~_ ~ _,, _
~: 4 13* 6.9 1~.2
_ _
4 - 14 6 . 2 _ 11 1
~ 15 6.4 12.1
.. __ _ - . .__ .
4 16 6 . 8 12 . 2
.... _ . __ . _
4 17 8.0 14.0
~ . ~ ~ - . ~, --~ ~.-.--=--_
* Comparatlve example

~5




,

~ ' . i ' . .

.i . ., :,

~al~6~77 -Z- 4656
~ .. _, _.
Example no . Sample no . rise in heigh~ [ cm ]
after 5 min. after 65 min.
. ..-- _
5. 18* 6.9 12.2
19 5 . 7 10 . ~
S 20 6.4 11.3
I _ .. .__ .. ___ .. __
1 5 21 6.612.3
._ ___ _ ~ . .__ _
22 7.5 14.0
- --_
6 23* d~.8 8.6
I . ,. _ . . ...... . .__. . _ _
6 24 6.3 11.3
I . _ . . .__ . ._ _._
1 6 ~5 5.3 10.3
. . . _ ~__
1 6 ~6 ~.5 10,7 l
~ .. _ _ ... . _
6 277.0 12.2
~ =~= _= =_~
7 28* 4.8 8 6
7 _ ~ 29__ _5 09 ~ 5 __
7 305.1 9.1
. _ . _ ~--
7 314.2 lO.S
I _ . ... ~
7 325.5 ll.q
=~ __ _~ ~_
8 33~ 6.0 10.0
I _. ... _ .. _ -- ___ . _ _~. _
8 34 6.0 11.1
_ .. _ _ --~
B 35 7 .1 13 . 3
.. . . _ _ _
8 36 i.4 13.5
.. .. _ - ... i.. __ . 11
8 37 ~.7 15.5
- _ __ ~_ .. ~ ~_.-------:~:=5C
~ Comparative example




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.. . ..

2 ~ ~ ~ 0 7 ~
17 O.Z. 4656
_ _ _ _ . ._ . . _.
Example no. Sample no. ri~e in height [cm]
after 5 min. after 65 min.
. _ _ . _ ,. .__ I
9_ __ 38* 3.9 _5 3
9 39 4.2 5.5
. . _. _____ T _r . . ________ ~
: g 40 4.~ 8.0
_ . - . _ _, ___ _
9 _ 41 ~ _ 6.3 _ _ _ 11.5
9 42 6.8 11.9
__ _ _ -- -=--=
43* 3.g 5.3
: 10 44 4.7 _
. _ _ . . . .. ___ . I
:~ _ ~ _ 45 ~_ 6.4
1~ 46 4.9 9.3
47 5.2 8.8
_ ; . . _ . ,_ , . . . .
*Compara~lve example

Explanation of the ri e in height re~ults:
In order to be able to clas~ify the test re~ults better,
the ri~es in height found for the 0 ~ample (terry fabric,
treated only with the commercial heavy duty deterqent
(PERSIL, Henkel) after 5 min.: 10.2 cm, after 65 min.:
: 18.5 cm) should be compared flr~t with those of ~ample
no~. 13 and 18 (treated wlth pure e~terquat, after 5 min.:
-~ 6.9 cm, after 65 min.s 12.2 cm), 23 and 28 ~treated with
pure 1, after 5 min.: 4.8 cm, af~er 65 min. 8.6 cm), 33
~treated with pure 2, after 5 min.: 6.0 cm, after S5 min.:
lO.0 cm) and 38 and 43 (treated with pure 3, after 5 min.:
3.9 cm, after 65 min.: 5.3 cm~. It can clearly be seen
that all the cationic nitrogen-containing fabric softener
active ingredient component~ or their ready-for-use
formulations examined cau~e ~ignificantly lower rises in
heiyh~ compaxed with the 0 ahmple, which i~ equivalent to
a greatly reduced rewetting capacity. ~he alkoxylated
natural fat~, oils and mixtures thereof with free fatty
acids, mo~o- and/or diglycerides do thi~ to a vary small
:


. ' ' , , .,'',,, ~ .~,:
- .. .

" ,.~ '"' ' :.

18 O.Z. 4656
extent, or not at all, at a similar u~e concentration of
0.3 or 0.4 g per litre of rinslng liquor, a~ ~mple no~.
2, 3, 6, 7, 10 and 11 show by way of example. Terry
fabric traated with alko~ylated natural fats, oils and
mixtures thereof with free fatty acids, mono- and/or
diglycerides thus exhibit~ an excellent rewetting
capacity. If the alkoxylated natural fat-~, oil~ and
mixtures thereof with Pree fatty acid3, mono- and/or
diglycer1des are used in mixture with the abovementioned
cationic nitrogen-containing fabric softener active
ingredien~ components or the ready-for-u~e formulati~ns
thereof, the following i~ found, taking the rises in
height after 5 and 65 minutes into account: none of the
mixtures rerommended in ~xample~ 1 - 10 causes a reductlon
in the rises in height in comparison with ~he corre~-
ponding cationic ~ubstance6. There i~ frequently even a
substantial increase.




.

;- , - , ,. ~
.: : .. ~, : .

Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(22) Filed 1993-05-12
(41) Open to Public Inspection 1993-11-15
Dead Application 1995-11-13

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1993-05-12
Registration of a document - section 124 $0.00 1993-10-22
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
HULS AKTIENGESELLSCHAFT
Past Owners on Record
BROCK, MICHAEL
HARDT, PETER
KLIMMEK, HELMUT
STOCKHAUSEN, DOLF
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) 
Drawings 1993-11-15 1 16
Claims 1993-11-15 2 94
Abstract 1993-11-15 1 30
Cover Page 1993-11-15 1 32
Description 1993-11-15 18 824