US3725503A - Polyamides with dispersed oxyalkyated grafted polyamides - Google Patents

Polyamides with dispersed oxyalkyated grafted polyamides Download PDF

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US3725503A
US3725503A US00149778A US3725503DA US3725503A US 3725503 A US3725503 A US 3725503A US 00149778 A US00149778 A US 00149778A US 3725503D A US3725503D A US 3725503DA US 3725503 A US3725503 A US 3725503A
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polyamides
filaments
fibers
weight
percent
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J Kunde
H Pohlemann
H Hendus
G Ramlow
G Buechler
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof

Definitions

  • the filaments [51'] I t Cl C08 04 or fibers are notable for their excellentantistatic pron u g parties and their soil hiding effect- 8 Claims, No Drawings
  • This invention relates to filaments or taining oxyalkylated polyamides.
  • I 1 POLYAMIDES WITH DISPERSEDOXYALKYATED GRAFTED POLYAMIDES I fibers of synthetic linearhigh molecular weight polyamides c'on-.
  • US. Pat. No. 3,329,557 reveals a method of incorporating antistatic agents such as polyalkylene glycols starting materials.
  • antistatic agents such as polyalkylene glycols starting materials.
  • Particularly suitable are polycapro-' lactam and polyhexamethyleneadipamideJ
  • the filafonic acid groups or alkali metalsulfonate groups in a proportion of, say, from 50 to 150 milli-equivalents per kilogram.
  • plastics materials such as polyamides.
  • polyalkylene glycols -or oxyalkylated polyamides of the said relatively low degree of oxyalkylation does not provide the advantages achieved by. the present invention, as is demonstrated by comparative tests.
  • I 'It is an object of the invention to provide filaments or fibers of polyamides showing a greatly reduced tenments or fibers contain, as a separate phase dispersed therein, from lto 15 percent by weight of highly oxyalkylated polyamides in which the ratio of synthetic linear polyamide having recurring amide groups in the backbone to 1,2-alkylene oxide of from two to four carbon atoms and chemically combined therewith is from lzlOtolzlSbyweight.
  • synthetic linear high molecular weight polyamides we mean those having recurring amide groups in thebackbone.
  • filaments or fib ers we means, for example, those obtained by a usual melt-spinning technique followed, if desired, by drawing and having a round or profiled cross-section, for example a trilobate or tetralobate cross-section.
  • Two-component filaments or fibers are also suitable.
  • Other suitable filaments or fibers are those produced from polyamide sheeting by mechanical means,'for example by cutting or fibrillating.
  • the filaments or fibers may be texturized, for example by false-twist or stuffer box processes or by means of mov- Suitable filament-forming or.
  • fiber-forming'synthetic linear polyamides are, for example,- the polycondensatesof lactams of from four to.
  • highly oxyalkylated polyamides be present in the filaments or fibers-during their formation.
  • highly oxyalkylated polyamides we mean synthetic linear polyamides having recurring amide groups in the backbone andwhich contain from 1 0 .to
  • the production of the-highly oxyalkylated polyamides is not generally'effected'directly from the polyamides and the 1,2-alkylene oxides. It may be carried out, for example, by reacting oxyalkylated polyamides showing a low degree of oxyalkylation, i. e. synthetic linear polyamides containing l,2-alkylene oxide in a ratio of from 1 :l to l 4'byweight, with l,2 -alkylene oxides at elevated temperatureand pressure, if necessary in the presence of basic'oxyalkylationcatalysts,
  • a polyamide which contains com bined l,2-alkylene oxide in a ratio of from 1 10 to '1 50' and in particular from 1 15 to l 30by wei'ght.
  • the reaction of the l,2-alkylene oxides with the synthetic linear polyamides takes place at the NH groups of the polyamides to fOrmchemicaIIy combined polyalkylene' oxide chains.
  • the said oxyalkylated polyamides may be classified as graft polymers.
  • Suitable 1,2-alkylene oxide or containing from two to four carbon atoms such as l ,2- butylene oxide and, in particular, ethyleneoxide and/or 1,2propylene oxide.
  • Suitable polyamides from which the highly oxyalkylated polyamides used as antistatic agents may be prepared are, for example, conventionally produced polycondensates of lactamsof from four to 12 carbon atoms, such as caprolactam, octanolactam, dodecanolactam or mixtures thereof; salts of diamines with dicarboxylic.acids ;of from four -.to 12, carbon atoms, such as salts of adipic acid, suberi'c acid- .or
  • the finished filament-forming polyamide in the molten state for'example by kneading or extruhomogeneous phase with the filament-forming or fiber- I forming polyamides; after the composition has'been shaped to'filaments or fibers cooled, the highlyoxepoxides are those yalkylated polyamides form separate, elongated particles.
  • the highly oxyalkylated polyamides impart excellent antistatic properties to the filaments or fibers.
  • the filaments are treated with hot aqueous liquors, for example during dyeing or washing, at temperatures between 90 and 110C, some of the particles of highly oxyalkylated polyamides embedded in the filaments or fibers are dissolved out leaving cavities.
  • These filaments or fibers show excellent brilliance and opacity, which in turn weakens the impression of soiling and significantly improves the soil-hiding effect over known filaments.
  • the good antistatic properties of the filaments or fibers of the invention are surprisingly retained after several washes.
  • the proportion of highly oxyalkylated polyamides in the filaments or fibers is conveniently from I to percent by weight.
  • the proportion of said highly oxyalkylated polyamides in the non-extracted filaments or fibers is conveniently from 2 to 15 percent by weight and preferably from 3 to 10 percent by weight, whilst the proportion thereof in the extracted filaments or fibers is conveniently from 1 to 8 percent by weight and preferably from 1 to 5 percent by weight. It is possible, if desired, to incorporate larger proportions of oxyalkylated polyamides, but this entails certain changes in the properties of the filaments.
  • the filaments or fibers of the invention prepared with the addition of highly oxyalkylated polyamides show a significantly better soil-hiding effect than filaments or fibers prepared with the addition of polyalkylene glycols or oxyalkylated polyamides showing a low degree of oxyalkylation, i. e. polyamides containing not more than four times their weight of 1,2-alkylene oxide.
  • polyalkylene glycols or oxyalkylated polyamides showing a low degree of oxyalkylation, i. e. polyamides containing not more than four times their weight of 1,2-alkylene oxide.
  • polyamides containing not more than four times their weight of 1,2-alkylene oxide One would have expected the effect to have approached that of polyalkylene glycols when polyamides are increasingly oxyalkylated.
  • the filaments or fibers of the invention show, after extraction, a charge of less than 300 volts at 35 percent relative humidity and virtually no measurable charge at all at a relative humidity of 65 percent, whilst filaments in which polyethylene oxide having a molecularweight of 20,000 has been incorporated show, after extraction, values of more than 900 volts and 200 volts respectively. Unmodified filaments show charges of about 2,500 and 1,000 volts respectively.
  • the filaments of the invention may contain other additives such as pigments, e. g. titanium dioxide, or light stabilizers and heat stabilizers. They are suitable, for example, for the manufacture of textiles such as woven, knitted or non-woven fabrics and, in particular, carpets.
  • strands of yarn are made.
  • the strands are extracted for 1 hour in boiling water and then stored at optical microscope with light directed from the side, after the said filaments or fibers have been extracted for 1 hour with boiling water.
  • Unmodified filaments appear dark, whilst the modified filaments show various degrees of brightness according to the effect of the additive.
  • EXAMPLE I EXAMPLE 2 7.5 parts of a highly oxyalkylated polycaprolactam consisting of 1 part of polycaprolactam (1 2.4) and 25 parts of chemically combined ethylene oxide are mixed into 92.5 parts of polyhe xamethyleneadipamide (1 2.7) in a twin worm kneader. A yarn is spun from the resulting granules and drawnat a draw ratio of l 3.28. It has a weight of 40/10 denier and is extracted as described in Example 1.
  • EXAMPLE 3 parts of hexamethylenediamineadipate (AH salt), 25 parts of waterand 5 parts of highly oxyalkylatedpolycaprolactam from 1 part of polycaprolactam (17 2.4) and 18 parts of ethylene oxide chemically combined therewith in 20 parts of water are heated in an autoclave at 280C, the pressure being held at 18 atmospheres by bleeding off steam. The pressure is than allowed to fall to atmospheric over 1 hour and condensation is continued for a further 45 minutes at 280C in a stream ofnitrogen. The resulting polycondensate is melt-spun and drawn at a ratio ofl 3.2 to form a 210/ 30 denier yarn. A strand is extracted in the manner described in Example 1.
  • Example 1 is repeated except that the additive used is a highly oxyalkylated polyamide from 1 part of a mixed polyamide consisting of 40 percent by weight of polycaprolactam and 60 percent by weight of polyhexamethyleneadipamide and 20 parts of chemically combined ethylene oxide.
  • the additive used is a highly oxyalkylated polyamide from 1 part of a mixed polyamide consisting of 40 percent by weight of polycaprolactam and 60 percent by weight of polyhexamethyleneadipamide and 20 parts of chemically combined ethylene oxide.
  • Example I is repeated except that the additive used is 5 parts of the reaction product of l part of caprolactam with 4 parts of chemically combined ethylene oxide as proposed in German Published Application DOS 1,494,963.
  • Example 1 is repeated except that the additive used I is 5 parts of a. a polyethylene oxide having a molecular weight of b. a polyethylene oxide having a molecular weight of 18,000 or I c. a polyethylene oxide having a molecular weight of 36,000, as proposed in US. Pat. No. 3,329,557.
  • filaments or fibers contain, as a separate phase dispersed therein, from 1 to 15 percent'by weight of highly oxyalkylated grafter polyamides in which synthetic linear polyamide having recurring amide groups in the backbone is grafted with l,2-alkylene oxide of from two to four carbon atoms and in which the ratio of the polyamide and the chemically bonded alkylene oxide is from 1 15 to l 50 by weight.
  • Filaments or fibers as claimed in claim 1, wherein the said ratio of synthetic linear polyamide to chemically combined 1,2-alkylene oxide is from 1 15 to 1 30 by weight.
  • Filaments or fibers as claimed in claim l containing 3 to 10 percent by weight of the said highly oxyalkylated polyamides.
  • Filaments or fibers as-claimed in claim 1 containing, after extraction with water, cavities and from 1 to 8 percent by weight of said highly oxyalkylated polya- 6.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyamides (AREA)
  • Artificial Filaments (AREA)

Abstract

Filaments or fibers of synthetic linear polyamides containing highly oxyalkylated polyamides. The filaments or fibers are notable for their excellent antistatic properties and their soilhiding effect.

Description

United States Patent 1191 Field of Search "260/857 TW, 857 PB .Kunde et al. 1 1* Apr. 1973 [54] POLYAMIDES WITH DISPERSED [56] References Cited XYAL RAFTED v g gag- G UNITED STATES PATENTS Inventors: Jochim- Kunde Frankemhal; Gen gka'zaki ..260/857 est ..260/857 Ludwfgshafen; 3,522,329 7/1970 Ok'azaki ..260/857 7 Gum!" r, 1 be g; 3,549,724 12/1970 Okazaki ..260/857 Heinz Pohlemann, Limburgerhof; Hans Hendus, Ludwigshafen, all of FOREIGN PATENTS 0R APPLICATIONS Germany 1,1 10,394 4/1968 Great Britain ..260/857 Assigneez Badische Anilhh Ak- 665,0l8 6/l965 Belgium .5. ...l.. 2V60 /857 e I I gigfiz g l ig udwlgs are", Primary Examiner-Paul Lieberman I v Attorney-Johnston, Root, O'Keeffe, Keil, Thompson [22] Filed: June 3, 1971 & Shurtleff [21] IAppl. No.1 149,778 I [57] ABSTRACT I Y I Q 7 I I l I v v Filaments or fibers of synthetic linear polyamideseon 1 [52.] Cl "260/857 260/37 2 332 taining highly oxy'alkylated polyamide s. The filaments [51'] I t Cl C08 04 or fibers are notable for their excellentantistatic pron u g parties and their soil hiding effect- 8 Claims, No Drawings This invention relates to filaments or taining oxyalkylated polyamides.
' ing gaseous media.
. I 1 POLYAMIDES WITH DISPERSEDOXYALKYATED GRAFTED POLYAMIDES I fibers of synthetic linearhigh molecular weight polyamides c'on-.
There is a great demand, forexample in the carpet industry, for fibers and filaments which show a reduced tendency to build up static charges and also exhibit increased brillianceand opacity, which in turn weaken the impression of soiling (soil-hiding effect) There have been a number of attempts to improve the antistatic properties of filaments or fibers by applying antistatic agents thereto. However, the stability of ,such finishes is unsatisfactory, since the agents are generally removed during washing or are dislodged by mechanical influences. v
US. Pat. No. 3,329,557 reveals a method of incorporating antistatic agents such as polyalkylene glycols starting materials. Particularly suitable are polycapro-' lactam and polyhexamethyleneadipamideJ The filafonic acid groups or alkali metalsulfonate groups in a proportion of, say, from 50 to 150 milli-equivalents per kilogram.
LII
plastics materials such as polyamides. However, the incorporation of polyalkylene glycols -or oxyalkylated polyamides of the said relatively low degree of oxyalkylation does not provide the advantages achieved by. the present invention, as is demonstrated by comparative tests.
I 'It is an object of the invention to provide filaments or fibers of polyamides showing a greatly reduced tenments or fibers contain, as a separate phase dispersed therein, from lto 15 percent by weight of highly oxyalkylated polyamides in which the ratio of synthetic linear polyamide having recurring amide groups in the backbone to 1,2-alkylene oxide of from two to four carbon atoms and chemically combined therewith is from lzlOtolzlSbyweight. By synthetic linear high molecular weight polyamides we mean those having recurring amide groups in thebackbone. f
By filaments or fib ers we means, for example, those obtained by a usual melt-spinning technique followed, if desired, by drawing and having a round or profiled cross-section, for example a trilobate or tetralobate cross-section. Two-component filaments or fibers are also suitable. Other suitable filaments or fibers are those produced from polyamide sheeting by mechanical means,'for example by cutting or fibrillating. The filaments or fibers may be texturized, for example by false-twist or stuffer box processes or by means of mov- Suitable filament-forming or. fiber-forming'synthetic linear polyamides are, for example,- the polycondensatesof lactams of from four to. 12 carbon atoms, such It is important that highly oxyalkylated polyamides be present in the filaments or fibers-during their formation. By highly oxyalkylated polyamides we mean synthetic linear polyamides having recurring amide groups in the backbone andwhich contain from 1 0 .to
50 times their weight of l ,2 -alkylene oxide chemically combined therewith. v
The production of the-highly oxyalkylated polyamides, which is not claimed in the present specification, is not generally'effected'directly from the polyamides and the 1,2-alkylene oxides. It may be carried out, for example, by reacting oxyalkylated polyamides showing a low degree of oxyalkylation, i. e. synthetic linear polyamides containing l,2-alkylene oxide in a ratio of from 1 :l to l 4'byweight, with l,2 -alkylene oxides at elevated temperatureand pressure, if necessary in the presence of basic'oxyalkylationcatalysts,
' such that a polyamide is produced which contains com bined l,2-alkylene oxide in a ratio of from 1 10 to '1 50' and in particular from 1 15 to l 30by wei'ght. The reaction of the l,2-alkylene oxides with the synthetic linear polyamides takes place at the NH groups of the polyamides to fOrmchemicaIIy combined polyalkylene' oxide chains. The said oxyalkylated polyamides may be classified as graft polymers.
Suitable 1,2-alkylene oxide or containing from two to four carbon atoms, such as l ,2- butylene oxide and, in particular, ethyleneoxide and/or 1,2propylene oxide.
Suitable polyamides from which the highly oxyalkylated polyamides used as antistatic agents may be prepared are, for example, conventionally produced polycondensates of lactamsof from four to 12 carbon atoms, such as caprolactam, octanolactam, dodecanolactam or mixtures thereof; salts of diamines with dicarboxylic.acids ;of from four -.to 12, carbon atoms, such as salts of adipic acid, suberi'c acid- .or
sebacic acid with hexamethylene diamine, ocv relative viscosities between l .5-and 2.9 to be particularly suitable. The incorporation of the highly oxyalkylated polyamides may be effected in any conventional manner, for example by thorough distribution in, ad-
as e-caprolactam, octanolactam, dodecanolactam or jtamethylene diamine .or dodecamethylene dia'mine, or mixed condensates of the above polyamide-forming vantageously, the finished filament-forming polyamide in the molten state, for'example by kneading or extruhomogeneous phase with the filament-forming or fiber- I forming polyamides; after the composition has'been shaped to'filaments or fibers cooled, the highlyoxepoxides are those yalkylated polyamides form separate, elongated particles.
The highly oxyalkylated polyamides impart excellent antistatic properties to the filaments or fibers. When the filaments are treated with hot aqueous liquors, for example during dyeing or washing, at temperatures between 90 and 110C, some of the particles of highly oxyalkylated polyamides embedded in the filaments or fibers are dissolved out leaving cavities. These filaments or fibers show excellent brilliance and opacity, which in turn weakens the impression of soiling and significantly improves the soil-hiding effect over known filaments. The good antistatic properties of the filaments or fibers of the invention are surprisingly retained after several washes.
The proportion of highly oxyalkylated polyamides in the filaments or fibersis conveniently from I to percent by weight. The proportion of said highly oxyalkylated polyamides in the non-extracted filaments or fibers is conveniently from 2 to 15 percent by weight and preferably from 3 to 10 percent by weight, whilst the proportion thereof in the extracted filaments or fibers is conveniently from 1 to 8 percent by weight and preferably from 1 to 5 percent by weight. it is possible, if desired, to incorporate larger proportions of oxyalkylated polyamides, but this entails certain changes in the properties of the filaments.
Suprisingly, the filaments or fibers of the invention prepared with the addition of highly oxyalkylated polyamides show a significantly better soil-hiding effect than filaments or fibers prepared with the addition of polyalkylene glycols or oxyalkylated polyamides showing a low degree of oxyalkylation, i. e. polyamides containing not more than four times their weight of 1,2-alkylene oxide. One would have expected the effect to have approached that of polyalkylene glycols when polyamides are increasingly oxyalkylated.
The filaments or fibers of the invention show, after extraction, a charge of less than 300 volts at 35 percent relative humidity and virtually no measurable charge at all at a relative humidity of 65 percent, whilst filaments in which polyethylene oxide having a molecularweight of 20,000 has been incorporated show, after extraction, values of more than 900 volts and 200 volts respectively. Unmodified filaments show charges of about 2,500 and 1,000 volts respectively.
The filaments of the invention may contain other additives such as pigments, e. g. titanium dioxide, or light stabilizers and heat stabilizers. They are suitable, for example, for the manufacture of textiles such as woven, knitted or non-woven fabrics and, in particular, carpets.
For the purpose of measuring the electrostatic charges, strands of yarn are made. The strands are extracted for 1 hour in boiling water and then stored at optical microscope with light directed from the side, after the said filaments or fibers have been extracted for 1 hour with boiling water. Unmodified filaments appear dark, whilst the modified filaments show various degrees of brightness according to the effect of the additive.
'In the following Examples the parts and percentages are by weight. The relative viscosities given (11 are measured in 1 percent w/w solution in 98 percent sulfuric acid at 20C.
EXAMPLE I EXAMPLE 2 7.5 parts of a highly oxyalkylated polycaprolactam consisting of 1 part of polycaprolactam (1 2.4) and 25 parts of chemically combined ethylene oxide are mixed into 92.5 parts of polyhe xamethyleneadipamide (1 2.7) in a twin worm kneader. A yarn is spun from the resulting granules and drawnat a draw ratio of l 3.28. It has a weight of 40/10 denier and is extracted as described in Example 1.
EXAMPLE 3 parts of hexamethylenediamineadipate (AH salt), 25 parts of waterand 5 parts of highly oxyalkylatedpolycaprolactam from 1 part of polycaprolactam (17 2.4) and 18 parts of ethylene oxide chemically combined therewith in 20 parts of water are heated in an autoclave at 280C, the pressure being held at 18 atmospheres by bleeding off steam. The pressure is than allowed to fall to atmospheric over 1 hour and condensation is continued for a further 45 minutes at 280C in a stream ofnitrogen. The resulting polycondensate is melt-spun and drawn at a ratio ofl 3.2 to form a 210/ 30 denier yarn. A strand is extracted in the manner described in Example 1.
EXAMPLE 4 Example 1 is repeated except that the additive used is a highly oxyalkylated polyamide from 1 part of a mixed polyamide consisting of 40 percent by weight of polycaprolactam and 60 percent by weight of polyhexamethyleneadipamide and 20 parts of chemically combined ethylene oxide.
COMPARATIVE EXAMPLE I Example I is repeated except that the additive used is 5 parts of the reaction product of l part of caprolactam with 4 parts of chemically combined ethylene oxide as proposed in German Published Application DOS 1,494,963.
Example 1 is repeated except that the additive used I is 5 parts of a. a polyethylene oxide having a molecular weight of b. a polyethylene oxide having a molecular weight of 18,000 or I c. a polyethylene oxide having a molecular weight of 36,000, as proposed in US. Pat. No. 3,329,557.
The effects achieved as regards reduction in static build-up and increase in brightness or brilliance are demonstrated in the following Table. Brightness is rated in grades 1 to 5 (5 very good).
Example Elecktrostatic Charge in Volts reached at a relative humidity of Brightness l 200 2 150 0 5 3 200 0 5 4 250 0 5 l 500 50 1 lla 900 150 2 llb 1500 450 3 He I400 450 2 Unmodified polycaprolactam 2300 1200 l mides.
groups in the backbone, which filaments or fibers contain, as a separate phase dispersed therein, from 1 to 15 percent'by weight of highly oxyalkylated grafter polyamides in which synthetic linear polyamide having recurring amide groups in the backbone is grafted with l,2-alkylene oxide of from two to four carbon atoms and in which the ratio of the polyamide and the chemically bonded alkylene oxide is from 1 15 to l 50 by weight.
2. Filaments or fibers as claimed in claim 1, wherein the said ratio of synthetic linear polyamide to chemically combined 1,2-alkylene oxide is from 1 15 to 1 30 by weight.
3. Filaments or fibers as claimed in claim l,containing 3 to 10 percent by weight of the said highly oxyalkylated polyamides.
4. Filaments or fibers as claimed in claim 1, containing highly oxyalkylated polyamides prepared with ethylene oxide.
5. Filaments or fibers as-claimed in claim 1, containing, after extraction with water, cavities and from 1 to 8 percent by weight of said highly oxyalkylated polya- 6. Filaments or fibers as claimed in claim 1, containing, after extraction with water, cavities and from -1 to 5 percent by, weight of said highly oxyalkylatedpolyarnidesf a 7. Filaments or fibers as claimed in claim 1, composed of polycaprolactam.
posed of polyhexamethyleneadipamide.
t il 1. Filaments or fibers of synthetic linear high molecular weight polyamides having recurring amide-

Claims (7)

  1. 2. Filaments or fibers as claimed in claim 1, wherein the said ratio of synthetic linear polyamide to chemically combined 1,2-alkylene oxide is from 1 : 15 to 1 : 30 by weight.
  2. 3. Filaments or fibers as claimed in claim 1, containing 3 to 10 percent by weight of the said highly oxyalkylated polyamides.
  3. 4. Filaments or fibers as claimed in claim 1, containing highly oxyalkylated polyamides prepared with ethylene oxide.
  4. 5. Filaments or fibers as claimed in claim 1, containing, after extraction with water, cavities and from 1 to 8 percent by weight of said highly oxyalkylated polyamides.
  5. 6. Filaments or fibers as claimed in claim 1, containing, after extraction with water, cavities and from 1 to 5 percent by weight of said highly oxyalkylated polyamides.
  6. 7. Filaments or fibers as claimed in claim 1, composed of polycaprolactam.
  7. 8. Filaments or fibers as claimed in claim 1, composed of polyhexamethyleneadipamide.
US00149778A 1971-06-03 1971-06-03 Polyamides with dispersed oxyalkyated grafted polyamides Expired - Lifetime US3725503A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932340A (en) * 1973-08-21 1976-01-13 Daicel Ltd. Nylon coating composition
US4546151A (en) * 1983-01-13 1985-10-08 Basf Aktiengesellschaft Oxyalkylated polyamidoamines and their preparation
US11078331B2 (en) 2018-04-06 2021-08-03 Workers First LLC Acid neutralizing polymer materal and method of making same
US11952463B2 (en) 2018-04-06 2024-04-09 Workers First LLC Acid neutralizing polymer powder

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3038885A (en) * 1958-11-12 1962-06-12 Firestone Tire & Rubber Co Preparation of nylon derivatives
BE665018A (en) * 1964-06-05 1965-12-06
GB1110394A (en) * 1964-07-31 1968-04-18 Basf Ag Polyamide polymers having an antistatic finish
US3514498A (en) * 1966-11-01 1970-05-26 Toray Industries Antistatic synthetic resin composition containing a polyether - polyamide block copolymer wherein an ionic functional group is made to coexist
US3522329A (en) * 1968-02-06 1970-07-28 Kaoru Okazaki Composition comprising polyester and polyether-polyamide blockcopolymer
US3549724A (en) * 1966-02-11 1970-12-22 Toray Industries Polyamide - polyether - polyamide block copolymer blend composition,a process for the production thereof and shaped articles thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3038885A (en) * 1958-11-12 1962-06-12 Firestone Tire & Rubber Co Preparation of nylon derivatives
BE665018A (en) * 1964-06-05 1965-12-06
GB1110394A (en) * 1964-07-31 1968-04-18 Basf Ag Polyamide polymers having an antistatic finish
US3549724A (en) * 1966-02-11 1970-12-22 Toray Industries Polyamide - polyether - polyamide block copolymer blend composition,a process for the production thereof and shaped articles thereof
US3514498A (en) * 1966-11-01 1970-05-26 Toray Industries Antistatic synthetic resin composition containing a polyether - polyamide block copolymer wherein an ionic functional group is made to coexist
US3522329A (en) * 1968-02-06 1970-07-28 Kaoru Okazaki Composition comprising polyester and polyether-polyamide blockcopolymer

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932340A (en) * 1973-08-21 1976-01-13 Daicel Ltd. Nylon coating composition
US4546151A (en) * 1983-01-13 1985-10-08 Basf Aktiengesellschaft Oxyalkylated polyamidoamines and their preparation
US11078331B2 (en) 2018-04-06 2021-08-03 Workers First LLC Acid neutralizing polymer materal and method of making same
US11952463B2 (en) 2018-04-06 2024-04-09 Workers First LLC Acid neutralizing polymer powder

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