U.S. patent application number 11/322994 was filed with the patent office on 2006-05-25 for water-soluble fiber and a method for manufacture thereof.
This patent application is currently assigned to Dai-ichi Kogyo Seiyaku Co., Ltd.. Invention is credited to Takeshi Fujita, Chuzo Isoda, Sejin Pu.
Application Number | 20060111544 11/322994 |
Document ID | / |
Family ID | 27468603 |
Filed Date | 2006-05-25 |
United States Patent
Application |
20060111544 |
Kind Code |
A1 |
Fujita; Takeshi ; et
al. |
May 25, 2006 |
Water-soluble fiber and a method for manufacture thereof
Abstract
This invention relates to a water-soluble fiber and a method of
manufacturing the fiber. The water-soluble fiber of the invention
is composed of a high molecular compound with a weight average
molecular weight of not less than 10,000, which high molecular
compound is obtainable by reacting a polyalkylene oxide compound,
which is obtainable by addition polymerization of an ethylene
oxide-containing alkylene oxide and an organic compound containing
two active hydrogen atoms, with a polycarboxylic acid, an anhydride
thereof, a lower alkyl ester thereof, or a diisocyanate and is
manufactured by spinning the same high molecular compound. The
water-soluble fiber of the invention is not only high in elongation
and tensile strength but is readily soluble in water.
Inventors: |
Fujita; Takeshi; (Kyoto,
JP) ; Isoda; Chuzo; (Kyoto, JP) ; Pu;
Sejin; (Kyoto, JP) |
Correspondence
Address: |
JORDAN AND HAMBURG LLP
122 EAST 42ND STREET
SUITE 4000
NEW YORK
NY
10168
US
|
Assignee: |
Dai-ichi Kogyo Seiyaku Co.,
Ltd.
Kyoto-shi
JP
|
Family ID: |
27468603 |
Appl. No.: |
11/322994 |
Filed: |
December 30, 2005 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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|
10422140 |
Apr 24, 2003 |
7001976 |
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11322994 |
Dec 30, 2005 |
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09596668 |
Jun 19, 2000 |
6566485 |
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10422140 |
Apr 24, 2003 |
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08591243 |
Jan 18, 1996 |
6093783 |
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09596668 |
Jun 19, 2000 |
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08371661 |
Jan 11, 1995 |
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08591243 |
Jan 18, 1996 |
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08065060 |
May 20, 1993 |
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08371661 |
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07682055 |
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08065060 |
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Current U.S.
Class: |
528/76 ;
528/301 |
Current CPC
Class: |
Y10T 428/2904 20150115;
D01F 6/70 20130101; Y10S 528/906 20130101; C08G 18/4837 20130101;
C08G 63/668 20130101; D01F 6/86 20130101; C08G 18/6674 20130101;
D01F 6/62 20130101 |
Class at
Publication: |
528/076 ;
528/301 |
International
Class: |
C08G 18/52 20060101
C08G018/52; C08G 63/66 20060101 C08G063/66 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 13, 1990 |
JP |
2-98087 |
Claims
1. A water-soluble fiber composed of a high molecular compound with
a weight average molecular weight of not less than 10,000, which
high molecular-compound is obtainable by reacting a polyalkylene
oxide compound, which is obtainable by addition polymerization of
an ethylene oxide-containing alkylene oxide and an organic compound
containing two active hydrogen atoms, with a polycarboxylic acid,
an anhydride thereof, a lower alkyl ester thereof, or a
diisocyanate.
2. A water-soluble fiber according to claim 1 which has an
elongation of 500 to 3,000 percent.
3. A method of manufacturing a water-soluble fiber which comprises
spinning a high molecular compound with a weight average molecular
weight of not less than 10,000, which high molecular compound is
obtainable by reacting a polyalkylene oxide compound, which is
obtainable by addition polymerization of an ethylene
oxide-containing alkylene oxide and an organic compound containing
two active hydrogen atoms, with a polycarboxylic acid, an anhydride
thereof, a lower alkyl ester thereof, or a diisocyanate.
4. A method of manufacturing a water-soluble fiber according to
claim 3 wherein the fiber as spun or in the course of spinning is
stretched in a draw ratio of 5 to 30.
Description
BACKGROUND OF THE INVENTION
[0001] The present invention relates to water-soluble fiber and a
method for manufacture thereof.
[0002] Among the water-soluble fibers heretofore known is polyvinyl
alcohol fiber which is generally fabricated into a twisted yarn,
woven fabric or non-woven fabric and put to use in a diversity of
applications. For example, it has been used for provisional
reinforcing or adhesion in a variety of industrial processes.
[0003] However, polyvinyl alcohol fiber is not readily soluble in
water and requires heating to at least about 80.degree. C. for
dissolution, thus being poor in workability. Moreover, when exposed
to a temperature over 100.degree. C., it undergoes crosslinking so
that dissolution is often made difficult.
SUMMARY OF THE INVENTION
[0004] The object of the present invention is to provide a
water-soluble fiber which is tough and readily soluble in water at
ambient temperature and does not suffer losses in water solubility
on exposure to heat and a method for manufacturing the fiber.
[0005] The present invention is directed to a water-soluble fiber
composed of a high molecular compound with a weight average
molecular weight of not less than 10,000, which high molecular
compound is obtainable by reacting a polyalkylene oxide compound,
which is obtainable by addition polymerization of an ethylene
oxide-containing alkylene oxide and an organic compound containing
two active hydrogen atoms, with a polycarboxylic acid, an anhydride
thereof, or a lower alkyl ester thereof, or a diisocyanate
compound.
[0006] The manufacture of said water-soluble fiber comprises
spinning said high molecular compound.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0007] The polyalkylene oxide compound as a major starting material
for the high molecular compound of the present invention is
preferably a compound having a weight average molecular weight of
not less than 100 and can be prepared by addition polymerization of
an ethylene oxide-containing alkylene oxide and an organic compound
containing two active hydrogen atoms.
[0008] The organic compound containing two active hydrogen atoms
includes, inter alia, ethylene glycol, propylene glycol,
polyethylene glycol, polypropylene glycol, polytetramethylene
glycol, 1,6-hexanediol, bisphenol A, aniline and so on.
[0009] The ethylene oxide-containing alkylene oxide includes, inter
alia, ethylene oxide and mixtures of ethylene oxide with propylene
oxide, butylene oxide, styrene oxide, .alpha.-olefin oxides,
glycidyl ethers and so on.
[0010] The addition reaction of such an alkylene oxide can be
carried out in the known manner, and the mode of addition
polymerization of ethylene oxide and other alkylene oxides may be
optionally random or block.
[0011] The polycarboxylic acid, anhydride thereof, or lower alkyl
ester thereof, which is reacted with said polyalkylene oxide
compound, include, inter alia, phthalic acid, isophthalic acid,
terephthalic acid, sebacic acid, dimer acid, pyromellitic acid, and
so on, anhydrides thereof, and methyl esters, dimethyl esters,
diethyl esters, and so on thereof. The preferred are dimethyl
terephthalate, dimethyl phthalate, dimethyl isophthalate, dimethyl
sebacate, pyromellitic anhydride and so on.
[0012] The polyester-forming reaction between said polyalkylene
oxide compound and said polycarboxylic acid, anhydride thereof or
lower alkyl ester thereof is preferably conducted at
120-250.degree. C. and 10.sup.-4-10 Torr.
[0013] The diisocyanate to be reacted with said polyalkylene oxide
compound includes, inter alia, tolylene diisocyanate,
diphenylmethane diisocyanate, hexamethylene diisocyanate,
isophorone diisocyanate, xylylene diisocyanate,
4,4'-methylene-bis-(cyclohexyl isocyanate) and so on.
[0014] The urethane-forming reaction between said polyalkylene
oxide compound and said diisocyanate is conducted by mixing the
starting compounds in an NCO/OH ratio of, for example, 1.5 through
0.5 and heating the mixture at 80 to 150.degree. C. for 1 to 5
hours.
[0015] A high molecular compound obtained by reacting a
polyalkylene oxide compound with a diphenylmethane diisocyanate has
a tendency to be insoluble in water for the following reason.
[0016] When preparing a polyalkelene oxide compound, an alkaline
metal hydroxide is used, which is usually neutralized with organic
acid to give an alkaline metal salt of organic acid. When the
polyalkylene oxide compound is reacted with diphenylmethane
diisocyanate without removing the salt, a high-molecular compound
which is insoluble in water is obtained as the salt works as a
catalyst for gelation.
[0017] In order to obtain a water-soluble compound, a retardant to
inhibit the gelation is employed for the reaction of the
polyalkylene oxide compound with diphenylmethane diisocyanate.
[0018] The weight average molecular weight of the high molecular
compound according to the present invention is not less than
10,000. If the molecular weight is less than 10,000, the fiber will
not be sufficiently high in mechanical strength, giving rise to
yarn breakage in the spinning process.
[0019] This high molecular compound can be processed into fiber by
any known relevant technique such as meltspinning, dry spinning,
wet-spinning, and so on, although the melt-spinning process is
preferred if only from economic points of view.
[0020] In the melt-spinning process, the high molecular compound is
melted at 50-200.degree. C. in a nitrogen gas atmosphere and
extruded from the conventional spinning nozzle.
[0021] In this process, such additives as a plasticizer, lubricant,
stabilizer, colorant, filler, and so on can be added. According to
the intended application, a perfume, fungicide, agrochemical,
fertilizer, and so on can also be incorporated.
[0022] The water-soluble fiber as spun has large elongation. For
example, the elongation of a fiber with a diameter of 10 .mu.m to 5
mm is approximately 500 to 3,000 percent.
[0023] After spinning, the fiber may be treated with a sizing or
bundling agent in the hydrocarbon series or stretched. When it is
stretched in a draw ratio of 5 to 30, its tensile strength is
remarkably increased. The stretching may be performed concurrently
with spinning.
[0024] The fiber thus obtained is subjected to various processings
such as twisting and cutting. The fiber can also be constructed
into mixed fabrics with other fibers.
[0025] The water-soluble fiber according to the present invention
is not only high in elongation and tensile strength but is readily
soluble in water. Moreover, this water solubility is not
appreciably affected by heating. Therefore, as processed into a
thread or yarn or a web, the fiber remains tough and
self-supporting in application and, yet, can be completely
dissolved out swiftly as needed. In this and other ways, this
material can contribute to rationalization of various industrial
processes.
[0026] The following examples and comparative examples are further
illustrative of the invention, it being to be understood, however,
that the invention is by no means limited thereof but limited only
by the claims appended hereto.
EXAMPLE 1
[0027] A polyethylene glycol having weight average molecular weight
of 10,000 was obtained by addition polymerization of ethylene oxide
and ethylene glycol. One hundred parts (parts by weight; the same
applies hereinafter) of the polyethylene glycol and 2.2 parts of
dimethyl terephthalate were used to give a polyester compound with
a weight average molecular weight of 130,000 (hereinafter referred
to as high molecular compound A).
[0028] This high molecular compound A was fed to a melt-spinning
apparatus, where it was melted at 120.degree. C. in a nitrogen gas
atmosphere and extruded through a spinning nozzle at a rate of 50
m/min, rapidly cooled under tension and taken up. A plain-weave
fabric was then constructed using a thread-like bundle of ten
filaments.
[0029] When put in water, this plain-weave fabric disappeared in 15
seconds. On the other hand, the same plain-weave fabric was locally
heat-sealed (120.degree. C., 1.5 seconds) to provide a firm local
bond. When this fabric was put in water, the whole fabric inclusive
of the bond disappeared in 18 seconds.
EXAMPLE 2
[0030] One-hundred parts of a polyalkylene oxide compound (weight
average molecular weight 20,000) prepared by block polymerization
of ethylene oxide (85%), propylene oxide (15%) and bisphenol A was
mixed with 0.84 part of hexamethylene diisocyanate and a small
amount of dibutyltin dilaurate and the mixture was heated at
100.degree. C. to give a high molecular compound with a weight
average molecular weight of 250,000.
[0031] This compound was extruded in the same manner as Example 1,
cut to 2-3 mm and processed into a nonwoven fabric. Using this
nonwoven fabric as a filter, a used vacuum pump oil (containing
0.50 of water) was purified. As a result, the water content was
reduced to 0.02% and the oil came clear. This purified oil could be
reused with full competence.
COMPARATIVE EXAMPLE 1
[0032] When a plain-weave fabric of polyvinyl alcohol fiber was put
in hot water at 80.degree. C., it disappeared in about 10 seconds.
In water at 25.degree. C., however, the fabric swelled as its
surface was wetted but remained to be dissolved completely as yet
even after one hour. On the other hand, the same plain-weave fabric
with a heat-sealed local bond remained partially undissolved even
in hot water at 80.degree. C.
EXAMPLE 3
[0033] The high molecular compound A synthesized in Example 1 was
fed to a melt-spinning apparatus, where it was melted at
120.degree. C. and extruded from a 1 mm (dia.) spinning nozzle at a
take-up rate of 30 m/min. The resulting monofilament-had a diameter
of 40 .mu.m and a tensile strength of 200 kg/cm.sup.2.
[0034] This fiber could be stretched in a draw ratio of 13 at
20.degree. C. and the stretched fiber had a diameter of 12 .mu.m
and a tensile strength of 390 kg/cm.sup.2.
[0035] At 50.degree. C., the fiber could be stretched in a draw
ratio of 20 to give a filament with a diameter of 9 .mu.m. The
tensile strength of this filament was 550 kg/cm.sup.2.
COMPARATIVE EXAMPLE 2
[0036] A wet-spun polyvinyl alcohol filament with a diameter of 40
.mu.m could be stretched only to twice its initial length at
20.degree. C. The stretched filament had a diameter of 28 .mu.m and
a tensile strength of 500 kg/cm.sup.2.
[0037] It is, thus, apparent that in the case of the water-soluble
fiber according to the present invention, its large elongation
permits stretching into finer fiber even if the filament as spun is
not so fine. Moreover, spinning troubles such as yarn breakage can
be prevented in accordance with the invention.
EXAMPLE 4
[0038] A polyalkylene oxide compound having weight average
molecular weight of 5,000 was obtained by addition polymerization
of 1,650 parts of propylene oxide, 3,850 parts of ethylene oxide
and 62 parts of dipropylene glycol with 10 parts of calcium
hydroxide as a catalyst.
[0039] One hundred parts of the polyalkylene oxide compound was put
into another vessel and melted at 100.degree. C. After 0.003 parts
of benzoyl chloride was added to the melt and the mixture was
stirred for 30 minutes, 4.8 parts of 4,4'-diphenylmethane
diisocyanate was added to the mixture and reacted with the
polyalkylene oxide compound for 5 hours to form urethane. A
water-soluble compound having weight average molecular weight of
150,000 was obtained.
[0040] The water-soluble compound was fed to a melt-spinning
apparatus, melted at 120.degree. C., and extruded through a
spinning nozzle having a diameter of 1 mm at a speed of 30 mm/min
to give a filament with a diameter of 40 .mu.m and a tensile
strength of 220 kg/cm.sup.2. When the filament was put into water
at 25.degree. C., it disappeared in 15 seconds.
[0041] At 20.degree. C., the filament was stretched in a draw ratio
of 13 to give a filament with a diameter of 12 .mu.m and a tensile
strength of 420 kg/cm.sup.2.
* * * * *