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Patent 2480283 Summary

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(12) Patent Application: (11) CA 2480283
(54) English Title: TEXTILE MILL APPLICATIONS OF CELLULOSIC BASED POLYMERS TO PROVIDE APPEARANCE AND INTEGRITY BENEFITS TO FABRICS DURING LAUNDERING AND IN-WEAR
(54) French Title: UTILISATIONS DANS UNE USINE TEXTILE DE POLYMERES A BASE DE CELLULOSE POUR CONFERER A DES TISSUS UN ASPECT ET UNE INTEGRITE NE S'ALTERANT PAS LORSQU'ILS SONT UTILISES ET LAVES
Status: Deemed Abandoned and Beyond the Period of Reinstatement - Pending Response to Notice of Disregarded Communication
Bibliographic Data
(51) International Patent Classification (IPC):
  • D06M 15/05 (2006.01)
  • C08B 11/193 (2006.01)
  • C08B 11/20 (2006.01)
  • C11D 3/22 (2006.01)
  • C11D 11/00 (2006.01)
  • D06M 15/07 (2006.01)
  • D06M 15/09 (2006.01)
(72) Inventors :
  • WANG, JIPING (United States of America)
  • WASHINGTON, NODIE MONROE (United States of America)
(73) Owners :
  • THE PROCTER & GAMBLE COMPANY
(71) Applicants :
  • THE PROCTER & GAMBLE COMPANY (United States of America)
(74) Agent: KIRBY EADES GALE BAKER
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 2003-04-16
(87) Open to Public Inspection: 2003-10-30
Examination requested: 2004-09-24
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US2003/011529
(87) International Publication Number: WO 2003089711
(85) National Entry: 2004-09-24

(30) Application Priority Data:
Application No. Country/Territory Date
60/372,877 (United States of America) 2002-04-16

Abstracts

English Abstract


Cellulosic based polymer or oligomer materials for use in textile mill
applications. The compositions of the present invention impart appearance and
integrity benefits to fabrics and textiles during laundering and in-wear. The
applications can be stand alone or incorporated into textile mill processes.
The materials can be applied onto yarns/fabrics/textiles/garments via pad-dry
processes or exhaustion methods.


French Abstract

L'invention concerne des polymères ou des oligomères à base de cellulose à utiliser dans des usines textiles. Les compositions présentées confèrent à des tissus et à des textiles un aspect et une intégrité ne s'altérant pas lorsqu'ils sont lavés et utilisés. Ces matières peuvent être utilisées seules ou bien dans le cadre de processus de fabrication de textiles. Ces matières peuvent être appliquées sur des fils/tissus/textiles/vêtements, selon des procédés de fixage par foulardage-séchage ou des procédés d'épuisement.

Claims

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


12
What is Claimed:
1. A textile mill treatment composition, said textile mill treatment
composition comprising:
a) a cellulosic based polymer or oligomer having the general formula:
<IMG>
wherein each R is selected from the group consisting of R2, R c, and
<IMG>
wherein:
- each R2 is independently selected from the group consisting of H and C1-C4
alkyl;
- each R c is
<IMG>
wherein each Z is independently selected from the group consisting of M, R2, R
c, and R H;
each R H is independently selected from the group consisting of C5-C20 alkyl,
C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl, C1-C20
alkoxy-2-hydroxyalkyl, C7-C20 alkylaryloxy-2-hydroxyalkyl, (R4)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (R4)3 N-alkyl, (R4)3 N-2-hydroxyalkyl, C6-C12 aryloxy-2-
hydroxyalkyl,
<IMGS>

13
- each R4 is independently selected from the group consisting of H, C1-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylaminoalkyl and
hydroxyalkyl;
- each R5 is independently selected from the group consisting of H, C1 -C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
(R4)2N-alkyl, and (R4)3N-alkyl;
wherein:
M is a suitable cation selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg;
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
- the Degree of Substitution for group R H is between about 0.0001 and 0.1,
more preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
- the Degree of Substitution for group R C wherein Z is H or M is between
about 0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
- if any R H bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
from the group
consisting of piperidine and morpholine.
2. The textile mill treatment composition of Claim 1 wherein said treatment
composition is added
to a padding bath, an exhaustion bath, or a spray applicator, preferably
wherein the pH of said
padding bath, exhaustion bath, or said spray application is from about 3 to
12.
3. The textile mill treatment composition of Claim 2 wherein said composition
is applied to a
woven fabric, a knit fabric, or a combination thereof.

14
4. A fabric or textile, said fabric or textile comprising by weight from about
0.005% to 10% of
cellulosic based polymers or oligomers of the general formula:
<IMG>
wherein each R is selected from the group consisting of R2, R c, and
<IMG>
wherein:
- each R2 is independently selected from the group consisting of H and C 1-C4,
alkyl;
- each R c is
<IMG>
wherein each Z is independently selected from the group consisting of M, R2, R
c, and R H;
- each R H is independently selected from the group consisting of C5 -C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl, C1-C20
alkoxy-2-hydroxyalkyl, C7-C20 alkylaryloxy-2-hydroxyalkyl, (R4)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (R4)3 N-alkyl, (R4)3 N-2-hydroxyalkyl, C6-C12 aryloxy-2-
hydroxyalkyl,
<IMG>
- each R4, is independently selected from the group consisting of H, C 1-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,

15
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylaminoalkyl and
hydroxyalkyl;
- each R5 is independently selected from the group consisting of H, C1 -C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
(R4)2N-alkyl, and (R4)3 N-alkyl;
wherein:
M is a suitable cation selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg;
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
- the Degree of Substitution for group R H is between about 0.0001 and 0.1,
more preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
- the Degree of Substitution for group R c wherein Z is H or M is between
about 0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
- if any R H bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
from the group
consisting of piperidine and morpholine.
5. A method for treating fabrics or textiles, said method comprising the steps
of:
a) providing a treatment composition wherein said treatment composition is
comprised of a
cellulosic based polymer or oligomer, wherein said cellulosic based polymer or
oligomer
preferably has an average molecular weight of from about 5,000 to about
2,000,000, and wherein
said cellulosic based polymer or oligomer has the general formula:

16
<IMG>
wherein each R is selected from the group consisting of R2, R c, and
<IMG>
wherein:
- each R2 is independently selected from the group consisting of H and C1-C4,
alkyl;
- each R C is
<IMG>
wherein each Z is independently selected from the group consisting of M, R2, R
c, and R H;
- each R H is independently selected from the group consisting of C5-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl, C1-C20
alkoxy-2-hydroxyalkyl, C7-C20 alkylaryloxy-2-hydroxyalkyl, (R4)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (R4)3N-alkyl, (R4)3N-2-hydroxyalkyl, C6-C12 aryloxy-2-
hydroxyalkyl,
<IMG>
- each R4 is independently selected from the group consisting of H, C7-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylaminoalkyl and
hydroxyalkyl;

17
each R5 is independently selected from the group consisting of H, C1-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
(R4)2N-alkyl, and (R4)3 N-alkyl;
wherein:
M is a suitable canon selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg;
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
- the Degree of Substitution for group R H is between about 0.0001 and 0.1,
more preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
- the Degree of Substitution for group R c wherein Z is H or M is between
about 0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
- if any R H bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
from the group
consisting of piperidine and morpholine; and
b) applying said cellulosic based polymer or oligomer to a fabric or textile
in the amount of from
about 0.005% to 10% by weight preferably wherein said fabric or textile is a
woven fabric, a knit
fabric, a nonwoven fabric, or a combination thereof.
6. A method for treating fabrics or textiles, said method comprising the steps
of
a) providing a treatment composition wherein said treatment composition is
comprised of a
cellulosic based polymer or oligomer wherein said cellulosic based polymer or
oligomer
preferably has an average molecular weight of from about 5,000 to about
2,000,000, and wherein
said cellulosic based polymer or oligomer has the general formula:

18
<IMG>
wherein each R is selected from the group consisting of R2, R c, and
<IMG>
wherein:
- each R2 is independently selected from the group consisting of H and C1-C4
alkyl;
each R C is
<IMG>
wherein each Z is independently selected from the group consisting of M, R2, R
c, and R H;
- each R H is independently selected from the group consisting of C5-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl, C1-C20
alkoxy-2-hydroxyalkyl, C7-C20 alkylaryloxy-2-hydroxyalkyl, (R4)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (R4)3 N-alkyl, (R4)3 N-2-hydroxyalkyl, C6-C12 aryloxy-2-
hydroxyalkyl,
<IMGS>
- each R4 is independently selected from the group consisting of H, C1-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylaminoalkyl and
hydroxyalkyl;

19
each R5 is independently selected from the group consisting of H, C1-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
(R4)2N-alkyl, and (R4)3 N-alkyl;
wherein:
M is a suitable cation selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg;
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
- the Degree of Substitution for group R H is between about 0.0001 and 0.1,
more preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
- the Degree of Substitution for group R c wherein Z is H or M is between
about 0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
- if any R H bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
from the group
consisting of piperidine and morpholine; and
b) adding said cellulosic based polymer or oligomer to a padding bath or an
exhaustion bath,
preferably wherein the pH range of said padding bath or said exhaustion bath
is from about 3 to
12; and
c) adding a fabric or textile to said padding bath or said exhaustion bath
whereby said cellulosic
based polymer or oligomer is applied to said fabric or textile in the amount
of from about 0.005%
to 10% by weigh and preferably wherein said fabric or textile is a woven
fabric, a knit fabric, a
nonwoven fabric, or a combination thereof.
7. The textile mill treatment composition of Claim 1 wherein said cellulosic
based polymer or
oligomer has an average molecular weight of from about 5,000 to about
2,000,000.
8. The textile mill treatment composition of Claim 1 wherein said treatment
composition further
comprises a textile additive, preferably wherein said textile additive is a
softener, soil release
agent, water repellant, dye fixative, durable press finishing agent,
antibacterial agent, or a
combination thereof.

20
9. The method of Claim 6 further comprising adding a textile additive to said
padding bath or
said exhaustion bath, preferably wherein said textile additive is a softener,
soil release agent,
water repellent, dye fixative, durable press finishing agent, antibacterial
agent, or a combination
thereof.
10. A system for treating textiles, said system comprising:
a) a cellulosic based polymer or oligomer having the general formula:
<IMG>
wherein each R is selected from the group consisting of R2, R c, and
<IMG>
wherein:
- each R2 is independently selected from the group consisting of H and C1-C4,
alkyl;
- each R C is
<IMG>
wherein each Z is independently selected from the group consisting of M, R2, R
c, and R H;
- each R H is independently selected from the group consisting of C5-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl, C1-C20
alkoxy-2-hydroxyalkyl, C7-C20 alkylaryloxy-2-hydroxyalkyl, (R4)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (R4)3 N-alkyl, (R4)3 N-2-hydroxyalkyl, C6-C12 aryloxy-2-
hydroxyalkyl,

21
<IMGS>
- each R4 is independently selected from the group consisting of H, C1-C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylaminoalkyl and
hydroxyalkyl;
- each R5 is independently selected from the group consisting of H, C1 -C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
(R4)2N-alkyl, and (R4)3 N-alkyl;
wherein:
M is a suitable cation selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg;
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
- the Degree of Substitution for group R H is between about 0.0001 and 0.1,
more preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
- the Degree of Substitution for group R c wherein Z is H or M is between
about 0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
- if any R H bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
from the group
consisting of piperidine and morpholine; and
b) a textile additive, preferably wherein said textile additive is a softener,
soil release agent, water
repellant, dye fixative, durable press finishing agent, antibacterial agent,
or a combination thereof.

Description

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


CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
1
TEXTILE MILL APPLICATIONS OF CELLULOSIC BASED POLYMERS TO
PROVIDE APPEARANCE AND INTEGRITY BENEFITS TO FABRICS DURING
LAUNDERING AND IN-WEAR
TECHNICAL FIELD
The present invention relates to textile mill applications of certain
cellulosic based polymer
or oligomer materials which impart appearance and integrity benefits to
fabrics and textiles
during laundering and in-wear. The applications can be stand alone or
incorporated into
traditional textile mill processes such as dyeing and finishing.
BACKGROUND OF THE INVENTION
It is, of course, well known that alternating cycles of using and laundering
fabrics and
textiles, such as articles of clothing and apparel, will inevitably adversely
affect the appearance
and integrity of the fabric and textile items so used and laundered. Fabrics
and textiles simply
wear out over time and with use. Laundering of fabrics and textiles is
necessary to remove soils
and stains which accumulate therein and thereon during ordinary use. However,
the laundering
and in-wear, over many cycles, can accentuate and contribute to the
deterioration of the integrity
and the appearance of such fabrics and textiles.
Deterioration of fabric integrity and appearance can manifest itself in
several ways. Short
fibers are dislodged from woven and knit fabric/textile structures by the
mechanical action of
laundering and abrasion/rubbing during in-wear. These dislodged fibers may
form lint, fuzz or
"pills" which are visible on the surface of fabrics and diminish the
appearance of newness of the
fabric. Further, repeated laundry-wear cycles of fabrics and textiles, can
remove dye from fabrics
and textiles and impart a faded, worn out appearance as a result of diminished
color intensity, and
in many cases, as a result of changes in hues or shades of color.
Given the foregoing, there is clearly an ongoing need to identify materials
which could be
added to textile mill applications which reduce or minimize the tendency of
fabric/textiles to
deteriorate in appearance during laundering and in-wear. Any applications of
such materials
should, of course, be able to benefit fabric appearance and integrity without
unduly interfering
with other fabric/textile properties such as fabric feel or hand feel,
draping, softness, smoothness,
etc.. The present invention is directed to the use of cellulosic based polymer
or oligomer
materials in textile mill application which perform in this desired manner.

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WO 03/089711 PCT/US03/11529
2
SUMMARY OF THE INVENTION
Cellulosic based polymer or oligomer materials which are suitable for textile
mill
applications and provide the desired fabric appearance and integrity benefits
can be characterized
by the following general formula:
R
O R
O~ ~ R
O O O
O
O O ~ ~O
I
O
R
wherein each R is selected from the group consisting of R~, Rc, and
CH2 CH O RH
R~ x
wherein:
- each R~ is independently selected from the group consisting of H and Cl-Cq,
alkyl;
O
I I
- each RC is ~CH2)y C-OZ~
wherein each Z is independently selected from the group consisting of M, R2,
R~, and RH;
- each RH is independently selected from the group consisting of C5 -CZp
alkyl, C5-C~
cycloalkyl, C~-CZp alkylaryl, C~-C2p arylalkyl, substituted alkyl,
hydroxyalkyl, C1-C20
alkoxy-2-hydroxyalkyl, C~-CZp alkylaryloxy-2-hydroxyalkyl, (Rq,)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (Rq,)3 N-alkyl, (Rq,)3 N-2-hydroxyalkyl, Cs-C12 aryloxy-2-
hydroxyalkyl,
O RS O RS O R5 O
-C CH C CH2, -C CH2 CH C-OM, ~d
O RS O
-C-CH-CH2-C-OM

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
3
- each R4 is independently selected from the group consisting of H, C1-C~0
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylarninoalkyl and
hydroxyalkyl;
- each R5 is independently selected from the group consisting of H, C 1 -C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
~4)2N-alkyl, and (R4)3 N-alkyl;
wherein:
M is a suitable cation selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg; a
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
- the Degree of Substitution fox group RH is between about 0.0001 and 0.1,
more preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
- the Degree of Substitution for group R~ wherein Z is H or M is between about
0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
- if any RH bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
fxom the group
consisting of piperidine and morpholine.
The cellulosic based polymer or oligomer materials defined above can be used
as an
additive in dyeing, dyeing aftertreatments, softenex finishing, hand building
finishing, durable
press finishing, antibacterial finishing, soil release finishing, and even
mechanical finishings, etc.
The materials can be applied onto yarns/fabrics/textiles/garments via pad-dry
processes or
exhaustion methods
The amount of the cellulosic based fabric treatment materials of the present
invention
needed in the textile mill applications to provide the best fabric appearance
benefits depends on
many factors such as yarn/fabric constructions, types of textile processes and
types of textile
equipment. Based on weight of fabrics, from about 0.005% to 10% of the
cellulosic based
materials is needed to impart fabrics with the best fabric appearance and
integrity. The preferred
amount is from about 0.01% to 3% based on weight of fabrics treated with the
cellulosic based

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
4
materials. Such benefits can include improved overall appearance, pill/fuzz
reduction, antifading,
improved abrasion resistance, and/or enhanced softness.
All percentages, ratios and proportions herein are on a weight basis unless
otherwise
indicated. All documents cited herein are hereby incorporated by reference.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 is an example of the pad-dry treatment process.
Figure 2 is an example of the exhaustion treatment method.
DETAILED DESCRIPTION OF THE INVENTION
A) Cellulosic Based Polymer or Oli~omer Materials
The essential component of the compositions of the present invention comprises
one or
more cellulosic based polymer or oligomer. Such materials have been found to
impart a number
of appearance benefits to fabrics and textiles after applied onto fabrics
during textile mill
applications. Such fabric appearance benefits can include, for example,
improved overall
appearance of the laundered fabrics, reduction of the formation of pills and
fuzz, protection
against color fading, improved abrasion resistance, etc. The cellulosic based
fabric treatment
materials used in the compositions and methods herein can provide such fabric
appearance
benefits with acceptably little or no loss in other preferred textile
properties such as fabric
feel/hand, draping, softness, smoothness, etc.
As will be apparent to those skilled in the art, an oligomer is a molecule
consisting of only
a few monomer units while polymers comprise considerably more monomer units.
For the
present invention, oligomers are defined as molecules having an average
molecular weight below
about 1,000 and polymers are molecules having an average molecular weight of
greater than
about 1,000. One suitable type of cellulosic based polymer or oligomer fabric
treatment material
for use herein has an average molecular weight of from about 5,000 to 'about
2.,000,000,
preferably from about 50,000 to about 1,000,000.
One suitable group of cellulosic based polymer or oligomer materials for use
herein is
characterized by the following formula:

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
R
O
R
O' O ~ R
O O
O
o ~ ~ -O
I
R R O
R
wherein each R is selected from the group consisting of R2, R~, and
CH2 CH O RH
R2
x
wherein:
each R2 is independently selected from the group consisting of H and Cl-Cq.
alkyl;
O
I I
eaehRcis ~CH2)y C-OZ,
wherein each Z is independently selected from the group consisting of M, R2,
Rc, and RH;
- each RH is independently selected from the group consisting of CS -C20
alkyl, CS-C~
cycloalkyl, C~-C20 alkylaryl, C~-C20 arylalkyl, substituted alkyl,
hydroxyalkyl, Cl-C20
alkoxy-2-hydroxyalkyl, C~-C20 alkylaryloxy-2-hydroxyalkyl, (Rq.)2N-alkyl,
(R4)2N-2-
hydroxyalkyl, (R4)3 N-alkyl, (Rq,)3 N-2-hydroxyalkyl, C6-C22 aryloxy-2-
hydroxyalkyl,
o RS o RS o RS o
-C CH C CH2~ -C CH2 CH C-OM~ and
O RS O
-C-CH-CH2-C-OM
each R4 is independently selected from the group consisting of H, Cl-C20
alkyl, C5-C~
cycloalkyl, C~-C2p alkylaryl, C~-C20 arylalkyl, aminoalkyl, alkylaminoalkyl,
dialkylaminoalkyl, piperidinoalkyl, morpholinoalkyl, cycloalkylaminoalkyl and
hydroxyalkyl;

CA 02480283 2004-09-24
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6
- each R5 is independently selected from the group consisting of H, C1 -C20
alkyl, C5-C7
cycloalkyl, C7-C20 alkylaryl, C7-C20 arylalkyl, substituted alkyl,
hydroxyalkyl,
(R4)2N-allcyl, and (R4)3 N-alkyl;
wherein:
M is a suitable cation selected from the group consisting of Na, K, 1/2Ca, and
1/2Mg;
each x is from 0 to about 5;
each y is from about 1 to about 5; and
provided that:
the Degree of Substitution for group RH is between about 0.0001 and 0.1, more
preferably
between about 0.0005 and 0.05, and most preferably between about 0.0008 and
0.01;
the Degree of Substitution for group Rc wherein Z is H or M is between about
0.2 and 2.0,
more preferably between about 0.3 and 1.0, and most preferably between about
0.4 and
0.7;
if any RH bears a positive charge, it is balanced by a suitable anion; and
- two R4's on the same nitrogen can together form a ring structure selected
from the group
consisting of piperidine and morpholine.
The "Degree of Substitution" for group RH, which is sometimes abbreviated
herein
"DSO", means the number of moles of group RH components that are substituted
per anhydrous
glucose unit, wherein an anhydrous glucose unit is a six membered ring as
shown in the repeating
unit of the general structure above.
The "Degree of Substitution" for group R~, which is sometimes abbreviated
herein
"DSR~", means the number of moles of group R~ components, wherein Z is H or M,
that are
substituted per anhydrous glucose unit, wherein an anhydrous glucose unit is a
six membered ring
as shown in the repeating unit of the general structure above. The requirement
that Z be H or M
is necessary to insure that there are a sufficient number of carboxy methyl
groups such that the
resulting polymer is soluble. It is understood that in addition to the
required number of RC
components wherein Z is H or M, there can be, and most preferably are,
additional R~
components wherein Z is a group other than H or M.
Other suitable cellulosic based polymer and/or oligomer materials are
described in WO
97/31950 published on September 4, 1997 and WO 98/56825 published December 17,
1998.
The production of materials according to the present invention is further
defined in the
Examples below.
B) Textile Mill Applications

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
7
The cellulosic based polymer or oligomer materials defined above can be used
as an
additive in dyeing, dyeing aftertreatments, softener finishing, hand building
finishing, durable
press finishing, soil release finishing, antibacterial finishing and even
mechanical finishings, etc.
The materials can be also used either by themselves alone or in conjunction
with other textile
additives such as but not limited to wetting agents, chelating agents, pH
control agents, softeners,
soil release agents, water xepellants, dye fixatives, durable press finishing
agents, antibacterial
agents, etc.. With regard to the textile processing process, the cellulosic
based polymer or
oligomer materials are commonly utilized during the dyeing and/or finishing
stages
The materials can be applied onto yarns/fabrics/textiles/garments via both pad-
dry
processes and exhaustion methods as shown in Figures 1 and 2 respectively or
via spray
application (not shown). The materials can be applied to woven fabric, lrnit
fabric, nonwoven
fabric, or combinations thereof. The pad-dry process is common for the dyeing
and finishing of
woven fabrics. No curing is necessary to fix the materials onto fabrics
although they are safe to
go through high temperature curing processes. Examples of high temperature
curing processes
include but are not limited to finishes such as durable press finishes and
antibacterial finishes.
The exhaustion method is commonly used to treat knit fabrics in the textile
mill
applications although some knit fabrics may be treated in the pad-dry process.
The amount of the cellulosic based fabric treatment materials of the present
invention
needed in the textile mill applications to provide the best fabric appearance
benefits depends on
many factors such as yarn/fabric constructions, types of textile processes and
types of textile
equipment. Based on the weight of the fabric, from about 0.005% to 10% of the
cellulosic based
materials is needed to impart fabrics with the best fabric appearance and
integrity. The preferred
amount is from about 0.01% to 3% based on the weight of the fabric treated
with the cellulosic
based materials. Such benefits can include improved overall appearance,
pill/fuzz reduction,
antifading, improved abrasion resistance, and/or enhanced softness.
With regard to the pad-dry process, referring to Figure 1, the concentration
of the cellulosic
based materials in the padding solution 20 should be determined by wet pick-
up. For example,
1% of the aqueous solution is needed in the padding bath 40 if the wet pick-up
is controlled as
100% based on the weight of the fabric 10 and 1 % of the cellulosic based
materials are needed to
deliver the fabric 10 appearance and integrity benefits.
Referring to Figure 2, for the exhaustion method, the amount of the cellulosic
based
materials added into the exhaustion bath 60 is determined by the weight of the
fabric 10. A non

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
limiting example would be, if a 1 % add-on level of the cellulosic based
materials to the fabric 10
is desired, this would be accomplished for example by adding 1 kg of the
cellulosic based
materials to the exhaustion bath 60 to treat 100 kg of fabric 10.
The pH range for fabric treatment is preferably from about 3 to 12 and more
preferably
from about 4 to 10.
EXAMPLES
The following examples illustrate the compositions and methods of the present
invention,
but are not necessarily meant to limit or otherwise define the scope of the
invention.
EXAMPLE I
Material composition for uad-dry application with a fabric softener
Materials Composition
Cellulose Based Polymer 0.5%
Wetting Agent 0.1 %
Fabric Softener 2.0%
Water 97.4%
pH 6-7
EXAMPLE II
Material comuosition fox uad-dry application with durable press
Materials Composition
Cellulose Based Polymer 10 g/1
Crosslinker Agent 60 g/1
Catalyst 15 g/1
Fabric Softener 20 g/1

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
9
Wetting Agent 3 g/1
Chelating Agent 5 g/1
pH 4-5
EXAMPLE III
Material composition for exhaustion application after dyeing
Materials Composition
Knitted Fabric 100 kg
Cellulose Based Polymer 1 kg
pH 7-8
EXAMPLE IV
Synthesis of modified CMC Materials
The carboxylation of cellulose to produce CMC is a procedure that is well
known to
those skilled in the art. To produce the modified CMC materials of this
invention, one adds
during the CMC making process the material, or materials, to be substituted.
An example of such
as procedure is given below. This same procedure can be utilized with the
other substituent
materials described herein by replacing the hexylchloride with the substituent
material, or
materials, of interest, for example, cetylchloride. The amount of material
that should be added to
the CMC making process to achieve the desired degree of substitution will be
easily calculated by
those skilled in the art in light of the following Examples.
Synthesis of Hexylether of CMC
This example illustrates the preparation of a carboxymethyl hydrophobically
modified
carboxymethyl cellulose and is representative of preparation of all of the
cellulose ether
derivatives of this invention.

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
Cellulose (20 g), sodium hydroxide (10 g), water (30 g), and ethanol (150 g)
are charged
into a 500 ml glass reactor. The resulting alkali cellulose is stirred 45
minutes at 25°C. Then
monochloroacetic acid (15 g) and hexylchloride (1 g) are added and the
temperature raised over
time to 95°C and held at 95°C for 150 minutes. The reaction is
cooled to 70°C, and then cooled
to 25°C. Neutralization is accomplished by the addition of a sufficient
amount of nitric
acid/acetic acid to achieve a slurry pH of between 8 and 9. The slurry is
filtered to obtain a
hexylether of CMC.
Table D
Specific Polymer Parameters
ID Polymer Type of Types of Chemistry
Modification*~
*A Hexyl CMC Hexyl ether Chlorohexane added
to CMC
making process
'~B Decyl CMC Decyl ether Chlorodecane added
to CMC
making process
C C 12-C 13 alkoxy-2C 12-C 13 alkoxy-2C 12-C 13 alkyl glycidyl
ether
hydroxypropyl hydroxypropyl added to CMC making
CMC
ether process
*D Hexadecyl CMC Hexadecyl etherChlorohexadecane added
to
CMC making process
~E Chloride salt chloride salt 2,3-epoxypropyltrimethyl
of 3- of 3-
trimethylammonio-2-trimethylammonio-ammonium chloride
added to
hydroxypropyl 2-hydroxypropylthe CMC making process
ether
of CMC ether

CA 02480283 2004-09-24
WO 03/089711 PCT/US03/11529
11
*F [-(C(O)- Cetyl Ketene Dimer added to
CH(C16H33)- CMC making process.
C(O)CH2,(C16H33) ]
ester of CMC or 1,3-
dioxo-2-
hexadecyloctadecyl
ester of CMC
CMC = Carboxymethylcellulose
* Manufactured by Noviant Specialty Chemicals
**DS~ for these materials was in the range of from about 0.001 to about 0.1
While particular embodiments of the present invention have been illustrated
and
described, it would be obvious to those skilled in the art that various other
changes and
modifications can be made without departing from the spirit and scope of the
invention. It is
therefore intended to cover in the appended claims all such changes and
modifications that are
within the scope of this invention.

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Administrative Status

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Event History

Description Date
Time Limit for Reversal Expired 2007-04-16
Application Not Reinstated by Deadline 2007-04-16
Deemed Abandoned - Failure to Respond to Maintenance Fee Notice 2006-04-18
Inactive: IPC from MCD 2006-03-12
Inactive: IPC from MCD 2006-03-12
Inactive: IPC from MCD 2006-03-12
Inactive: Cover page published 2004-12-08
Inactive: First IPC assigned 2004-11-28
Letter Sent 2004-11-26
Letter Sent 2004-11-26
Inactive: Acknowledgment of national entry - RFE 2004-11-26
Application Received - PCT 2004-10-26
National Entry Requirements Determined Compliant 2004-09-24
Request for Examination Requirements Determined Compliant 2004-09-24
All Requirements for Examination Determined Compliant 2004-09-24
Application Published (Open to Public Inspection) 2003-10-30

Abandonment History

Abandonment Date Reason Reinstatement Date
2006-04-18

Maintenance Fee

The last payment was received on 2004-09-24

Note : If the full payment has not been received on or before the date indicated, a further fee may be required which may be one of the following

  • the reinstatement fee;
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Fee History

Fee Type Anniversary Year Due Date Paid Date
Request for examination - standard 2004-09-24
MF (application, 2nd anniv.) - standard 02 2005-04-18 2004-09-24
Registration of a document 2004-09-24
Basic national fee - standard 2004-09-24
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
THE PROCTER & GAMBLE COMPANY
Past Owners on Record
JIPING WANG
NODIE MONROE WASHINGTON
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) 
Description 2004-09-24 11 451
Claims 2004-09-24 10 334
Drawings 2004-09-24 1 13
Abstract 2004-09-24 1 54
Cover Page 2004-12-08 1 33
Description 2004-09-25 11 446
Claims 2004-09-25 11 295
Acknowledgement of Request for Examination 2004-11-26 1 177
Notice of National Entry 2004-11-26 1 201
Courtesy - Certificate of registration (related document(s)) 2004-11-26 1 106
Courtesy - Abandonment Letter (Maintenance Fee) 2006-06-13 1 175
PCT 2004-09-24 6 216