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Publication numberUS3696078 A
Publication typeGrant
Publication dateOct 3, 1972
Filing dateAug 13, 1970
Priority dateAug 13, 1970
Publication numberUS 3696078 A, US 3696078A, US-A-3696078, US3696078 A, US3696078A
InventorsAndrew I Smith, Roland J Bryan Jr
Original AssigneeMonsanto Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Antistatic nylon filaments
US 3696078 A
Abstract  available in
Previous page
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Claims  available in
Description  (OCR text may contain errors)

United States Patent US. Cl. 260-78 S 7 Claims ABSTRACT OF THE DISCLOSURE The antistatic property of nylon filaments containing from about 2% to 15% by Weight of a oly(alkylene ether, polyethoxylated hydrogenated castor oil, or polyethoxylated distearylarnine dispersed therein) is greatly improved by also dispersing into the nylon from 0.5 to 5% by weight of a phosphonium bromide of the formula where R and each R are hydrocarbon radicals.

BACKGROUND OF THE INVENTION It is known that nylon yarns composed of filaments containing a polyethoxylated, hydrogenated castor oil or a high molecular Weight polyethylene glycol dispersed therein as a separate phase are more conductive than regular nylon yarns and, as a result, have an improved antistatic property. We have found that the conductivity of the poly(alkylene ether)-containing nylon yarns can be further improved by rinsing the yarns after scourings or dyeing operations in various salt solutions such as aqueous solutions of sodium acetate, sodium chloride, etc. Such treatment is apparently eifective because the salt solutions diffuse into the small pores of the yarns that are formed during the spinning process and from which a portion of the water-soluble polyethoxylated hydrogenated castor oil or polyethylene glycol is leached during the scouring or dyeing operations. However, this improved conductivity is either partially or completely lost when the treated yarns are either rinsed or further Washed in non-salt-containing water, e.g., as by machine laundering.

The primary object of the present invention is to improve the antistatic properties of nylon filaments containing a oly(alkylene ether), polyethoxylated hydrogenated castor oil or polyethoxylated dialkylamine therein.

SUMMARY OF THE INVENTION The present invention provides nylon (polycarbonamide) filaments containing dispersed therein, in addition to a poly(alkylene ether, polyethoxylated hydrogenated castor oil or polyethoxylated distearylamine) from 0.5 to 5% and, preferably, 0.5 to 3% by weight, based ice on the weight of the nylon, of a phosphonium bromide selected'from the group consisting of orm 2)m where m is 2 to 4, and of the structure where p is 0 to 4, etc. The phosphonium bromides may be prepared by reacting a tertiary phosphine (R P) with an organic bromide (RBr) or (R'Br).

Poly(alkylene ethers), polyethoxylated hydrogenated castor oils and polyethoxylated distearylamines which are useful in providing the nylon filaments of the present invention are those having a molecular weight of at least 1,000 (e.g. 1,000 to 30,000). The poly(alkylene ethers) have recurring R"O- units wherein R" is an alkylene radical having from 2 to 4 carbon atoms. The polyethoxylated distearyla-mines and polyethoxylated hydrogenated castor oils containing at least by Weight of recurring -CH CH O- units. These polyalkoxylated compounds may be formed by reacting an alcohol, hydrogenated castor oil or disterylarnine Wit han appropriate amount of a C to C alkylene oxide, such as ethylene oxide. Representative oly(alkylene ethers) include: polyethylene glycol, polypropylene glycol, block copolymers of polyethylene glycol and polypropylene glycol, polyethoxylated lauryl alcohol and the like. Generally, from 2% to 15% by weight of the polyalkoxylated compound is incorporated into the nylon polymer.

The term nylon is used herein to denote linear, fiberforming polycarbonamides which contain recurring carbonamide units separated from one another by at least The phosphonium bromides may be added to the nylon salt or salt solution prior to the evaporation or polymerization cycles, or during the polymerization cycles, or they may be estirred into the molten polymer during the holding (equilibrium) cycle when polymerization is essentially completed. Preferably, the phosphonium bromides are first mixed with one or more of the polyalkoxylated compounds described herein and then the resulting mixture or blend is stirred into the molten polymer during the holding cycle.

The phosphonium bromides by themselves do not improve the conductivity of nylon yarn. However, when the bromides are added to nylon in addition to one or more of the polyalkoxylated compounds described herein yarns made therefrom are more conductive than like yarns containing only said polyalkoxylated compound(s).

DESCRIPTION OF THE PREFERRED EMBODIMENTS The following example is given to more fully illustrate the invention. In the example percentages and parts are by weight unless otherwise specified.

Example Twelve yarns were prepared, each according to the following procedure:

To a stanless steel, high pressure autoclave was added 151 parts of hexamethylene ammonium adipate and 50 parts of water. The autoclave was equipped with stirring means to permit the contents to be agitated. The phosphonium bromide (and the amount thereof) indicated in the table was dissolved in water and added to the adipate salt solution. The autoclave was purged of oxygen by use of purified nitrogen and the temperature and pressure were slowly raised until values of 243 C. and 250 p.s.i.g. were reached. During this time steam was continuously removed from the autoclave as a condensate. The pressure was then gradually reduced to atmospheric over a 25 minute period. The polymer was then permitted to equilibrate for 30 minutes at 278 C., during which time an amount of a polyethoxylated compound, indicated in the table, was blended into the polymer melt by stirring at 244 rpm. for 25 minutes. The finished polymer was melt spun directly from the bottom of the autoclave through a 13-hole spinneret to yield white multifilament yarn. The yarn was drawn to provide a yarn having a denier of approximately 7 with a 35% elongation. Each of the twelve yarns was knitted into a tubular fabric and tested for static build-up.

In testing for static build-up each fabric was blankdyed for one hour at the boil with a 40:1 liquor-to-goods ratio with 0.5% of sodium-N-methyl-N-oleoyl taurate. The fabric was rinsed for 15-20 seconds with deionized water (:1 ratio) and then, after drawing for seconds, was rinsed for 20 minutes with occasional stirring at a 40:1 ratio with deionized water. After drying for at least 16 hours at ambient conditions, the fabric was placed in a room with a Hayek-Chromey static instrument and permitted to equilibrate at 40% relative humidity for at least 2 days before static measurements were made. Then the tubular fabrics were folded lengthwise and placed in the Hayek-Chromey instrument sample holders. The instrument was run for one minute without contact between the sample fabric and the contact arm, which was covered with a finish-free nylon fabric, to determine the ground or starting charge (zero for all conducting yarns). The contact arm was then contacted with the rotating fabrics for 60 seconds to build up a static charge on the sample fabric. After the contact between the sample fabric and arm was broken, the time for half the accumulated charge on the sample fabric to dissipate therefrom was measured. The results of these tests are given in the table.

TAB LE Polyethoxylated compound Phospho- Bromide Static nlum amount, Amount, half-life, type percent Type percent seconds Yarn sample:

1 0 X 6. 5 185 1 X 6. 5 2 X 7 13 3 X 7 18 2 X 7 l 45, 14 2 0 3 10 0 Y 7 1 484 2 Y 7 l 153 3 0. 4 X 7 12 l X 7 63 3 0. 4 X 7 32 1 X 7 71 1 Blank-dyed fabric heated 20 minutes at C. 9 Minutes. 3 Added with poly(alkylene ether) during equilibrium cycle.


A=Methyltriphenyl phosphonium bromide B =(n-Butyl) triphenyl phosphonium bromide C p-Xylylenebis (triphenyl phosphonium bromide) X=Hydrogenated castor oil polyethoxylated with 200 moles of ethylene oxide per mole of oil having the structure:

O CH2CH2O H o (L cHroh (CH2)10 H(CH2) CH3 Q l O CHzCHzO H GHQ-Q l Q:OL (CH2)1o incnm m Y=Polyethylene glycol (MW-20,000)

The phosphonium bromides (A, B and C) were purchased from Aldrich Chemical Co. and were used as received.

The results show that the addition of a phosphonium bromide per se to the nylon polymer did not improve the conductivity of the yarn, whereas the addition of both a phosphonium bromide and a polyalkoxylated compound of the type described herein to the nylon polymer rendered the yarn substantially more conductive than yarn containing only the said polyalkoxylated compound.

Similar results are also attained when other nylons, bromides and polyalkoxylated compounds of the type described herein are used instead of those specifically illustrated in the example.

We claim:

1. A static-resistant polycarbonamide filament containing dispersed therein (A) from 2 to 15% by weight of a compound having a molecular weight of at least 1,000, said compound being selected from the group consisting of poly(alkylene ethers) having recurring R"O- units in which R" is a C to C alkylene radical, polyethoxylated distearylamine, polyethoxylated hydrogenated castor oil and mixtures thereof, wherein said polyethoxylated distearylamine and said polyethoxylated hydrogenated castor oil contain at least 70% by weight of recurring CH CH O units and (B) from 0.5 to 5% by weight of a phosphonium bromide selected from the group consisting of /P\ Brand Br- 2. The filament of claim 1 wherein the said compound 5. The filament of claim 1 wherein the phosphonium is polyethoxylated hydrogenated castor oil of the formula bromide is n-butyltriphenyl phosphonium bromide.

6. The filament of claim 1 wherein the phosphonium O OH0H,0 H bromide is p-xy1ylenebis(triphenyl phosphonium bro- 5 mide). HQCO wHmoCHCQHH 7. The filament of claim 1 wherein the said compound is polyethylene glycol. 0--cH1cH,0-- E I References Cited H o UNITED STATES PATENTS H 3,206,496 9/1965 Rauhut 16-Dig. 0 3,226,178 12/1965 Walker 17--Dig. 0A c J 3,388,104 6/1968 Crovatt 26078 S 3,496,147 2/ 1970 Cubbon 26078 S in which the sum of x, y and z equals an integer between and 450.

3. The filament of claim 1 wherein the phosphonium HAROLD ANDERSON Pnmary Exammer bromide is a C to C alkyltriphenyl phosphonium bro- CL mide.

4. The filament of claim 1 wherein the phosphonium 0 57-140 8 N, 78 R, Dig. 16, 17, 19 bromide is methyltriphenyl phosphonium bromide.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3879928 *Nov 1, 1973Apr 29, 1975Perfect Thread Company IncProcess for the manufacture of yarn and the resulting product
US4038258 *Oct 22, 1976Jul 26, 1977E. I. Du Pont De Nemours And CompanyAntistatic composition containing an aliphatic polyester or polyether ester and a phosphonium salt
US4559151 *May 7, 1984Dec 17, 1985Sterling Drug Inc.Antistatic fabric conditioner compositions and method
US5407982 *Nov 19, 1993Apr 18, 1995Shell Oil CompanyAdding onium iodide salt of nitrogen, phosphorus, or arsenic
US6124386 *Jun 16, 1998Sep 26, 2000Asahi Glass Company Ltd.Blend with a polyarylene thioether such as polyphenylene sulfide which blend also includes an organic onium compound such as tetrabutylphosphonium bromide in given weight ratio; excellent mechanical properties
USRE29572 *Jan 12, 1977Mar 14, 1978Perfect Thread Company, Inc.Process for the manufacture of yarn and the resulting product
U.S. Classification524/121, 524/154, 260/DIG.170, 528/335, 57/901, 260/DIG.160, 260/DIG.190, 524/602, 528/323, 528/336, 528/313
International ClassificationC08K5/50
Cooperative ClassificationY10S260/17, Y10S260/16, Y10S260/19, Y10S57/901, C08K5/50
European ClassificationC08K5/50