US2938914A - Alkyl trialkylammonium salts as disperse dyes for acrylic fibers - Google Patents

Alkyl trialkylammonium salts as disperse dyes for acrylic fibers Download PDF

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US2938914A
US2938914A US753124A US75312458A US2938914A US 2938914 A US2938914 A US 2938914A US 753124 A US753124 A US 753124A US 75312458 A US75312458 A US 75312458A US 2938914 A US2938914 A US 2938914A
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Joyce Asa Willard
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Wyeth Holdings LLC
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American Cyanamid Co
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/207—Dyes with amino groups and with onium groups

Definitions

  • the polyacrylonitrile fibers which have become increasingly useful articles of commerce, are diflicult to dye. Most of the commercially available fibers of this type contain a major proportion of polyacrylonitrile. In most cases over 85% of the fiber is acrylonitrile. Few of the standard dyestuffs available show afiinity for these high acrylonitrile content fibers. Especially it has been hard to obtain deep shades on these fibers since deep shades require a strong aifinity of the fiber for the dyestuif. The only way to achieve deep shades has been to increase the time and temperatures of the dyeing process. Such drastic conditions of dyeing result in injury to the fabrics. The resistant properties of these fibers are desirable for general textile use because they render the fiber physically durable.
  • R" is hydrogen or alkyl of less than seven carbon atoms, R is lower alkyl, R is lower alkyl or cyclohexyl; n is an integer from 2 to 4 and A- is an anion, have excellent affinity for polyacrylonitrile fibers with major ingly' soluble in water, dyeing acrylic fibers with major proportion of acrylonitrile with great ease by the usual disperse methods.
  • the dyes of my invention are usually prepared from 2,938,914 Patented May 31,
  • the alkyl groups need not' be the same so that one can use methylethylaminoethylamine o methylethylaminopropylamine and the like.
  • Thenitro group may be replaced with ammonia to give the free amine or with a lower alkyl amine such as methylamine, ethylamine, butylamine, isobutylamine, isopropylamine, tert-butylamine or with cyclohexylamine.
  • a lower alkyl amine such as methylamine, ethylamine, butylamine, isobutylamine, isopropylamine, tert-butylamine or with cyclohexylamine.
  • the quaternization is eifected by reaction with a compound of the general formula RA in which R is the quaternizing group and A is the anion which may contain an alkyl or other organic residue.
  • dialkyl sulfates such as dimethyl sulfate, diethyl sulfate, dipropyl sulfate or dibutyl sulfate
  • alkyl halides such as methyl iodide, ethyl iodide, methyl chloride, ethyl chloride, butyl bromide, hexyl bromide, and the like, aralkyl halides such as benzyl chloride, phenylethylbromide and the like or alkyl esters of aryl sulfonic acids such as the methyl, ethyl, propyl or butyl esters of para-toluene sulfonic acid or substituted alkyl halides such as ethylene chlorohydrin, propylene chlorohydrin and the like, or alkenyl halides such as alkyl brornide
  • alkyl halides such as methyl iodide,
  • Polyacrylonitriles which may be dyed with the compound of my invention. and which fall within the scope of my invention are those polymers and copolymers of acrylonitrile which contain a major proportion by weight of acrylonitrile, they may also contain basic comonomers as methyl vinyl pyridine and vinyl pyridine or comonomer-s such as methyl acrylatc, vinyl acetate and vinyl chloride.
  • polyacrylonitriles available commercially which can be used to form the colored polyacrylonitriles of my invention, one is 100% polyacrylonitrile, another is approximately 95% acrylonitrile and approximately 5% methyl acrylate, another'has 89% of acrylonitrile, 6% methyl vinyl pyridine and 5% vinyl acetate, and still another has a composition of 94% acrylonitrile, 5% methyl vinyl pyridine and 1% vinyl acetate.
  • Polymers having as little as 50% acrylonitrile can be dyed by the class of dyes of my invention to form the dyed fibers of my invention.
  • the new dyes which I have invented are surprisingly soluble in water and dye acrylic fibers having a major proportion of acrylonitrile with ease by the usual disperse dyeing methods.
  • the preferred method of application is at the boil in an aqueous dye bath which is neutral to weakly alkaline, although fibers can also be dyed in an acidic medium.
  • the dyes are orange .red to red violet shades of good fastness to washing.
  • a mixture of 6.3 parts by weight of the above product, 75 parts by volume of toluene, and 4.1 parts by volume of 70% ethylamine is gradually warmed to C.
  • the mixture is heated at 85-95 C. until the reaction is complete.
  • the partially precipitated product is isolated by evaporation and dried.
  • the product is l-ethylamino- 6-dimethylaminopropylaminosulfonyl anthraquinone.
  • Example 2 2.7 parts of the product of Example 1 in 100 parts by volume of water are treated with 10 parts of potassium iodide. The sulfate anion is thus replaced by an iodide anion. The product is isolated by filtration.
  • Example 1 If in Example 1 the ethylamine is replaced with 1.4 parts of methylamine, a corresponding cationic anthraquinone dyestuflf of the above formula is obtained which dyes polyacrylonitrile fibers having a high acrylonitrile content reddish-violet shades.
  • Example 4 CHaCHzCILCHg-NH 0 02H soiNn-omomomonr-r r cnnsor i 1 02 5 0 10.6 parts of 1-nitro-G-anthraquinonylsulfonyl chloride are slurried in 75 parts by volume of benzene. To this is added 8.7 parts of diethylaminobutylamine and the 70 mixture warmed at 50 C. until reaction is complete.
  • the product (1-nitro-6-diethylaminobutylaminosulfonyl anthraquinone) is isolated by filtration and washed with benzene.
  • This product is then mixed with parts by volume of 75 toluene and 7.3 parts of butylamine is added.
  • the mixa ma ture is heated at 85-95 C. until the nitro group is substantially replaced by butylamino groups.
  • the product is isolated by evaporation.
  • the product obtained (l-butylamino-G-diethylaminobutylaminosulfonyl anthraquinone) is added to 200 parts by volume of orthodichlorohenzene and heated at reflux until dissolved. To this solution is added 6.1 parts of diethyl sulfate and the mixture is heated at 85 C. until quaternization is complete.
  • the product of the formula above is then isolated by filtration, washed with orthodichlorobenzene and dried. It dyes acrylonitrile polymers, both those with basic comonomers and from weakly alkaline baths, reddishwiolet shades.
  • the product is added to 150 parts by volume of toluene. To this is added 8.9 parts of cyclohexylamine and the mixture heated at 85-95 C. until the nitro group is substantially replaced with a cyclohexylamino group.
  • the product is isolated by evaporation and quaternized using an excess (about 2.6 parts) of ethyl chloride, using the solvent and quaternization method of Example 4.
  • the reaction mixture is cooled to 50 C. and filtered.
  • the product is washed with orthodichlorobenzene and dried. It dyes acrylic fibers having a high acrylonitrile content reddish-violet shades.
  • Example 2 If in Example 1, 10.6 parts of 1-nitro-6-anthraquinony1- sulfonyl chloride are replaced by the same amount of 1-nitro-7-anthraquinonylsulfonyl chloride, 21 water soluble cationic dyestutf is obtained which dyes Orlon a violet shade, which is somewhat redder than the dye produced in Example 1.
  • Example 7 H The procedure of Example 1 is followed except that the second step (replacement of the nitro group by ethylamine) is carried out in o-dichlorobeuzene instead of toluene (in equal amount) by passing ammonia gas through the solution, the mixture being held at 160 C. and the ethylamine being omitted.
  • the final product is the dye of the above structure which dyes acrylic fibers a bright orange red.
  • Acrylic fibers may be dyed with the dyes of the preced ing examples by the following preferred procedure: To a dye bath is added a piece of acrylic cloth consisting of between -l00% acrylonitrile plus 40 parts of water per unit weight of the fabric and one part by weight of the dyestuff of Example 1 and 1 part by weight of sodium carbonate solution. The dye bath is boiled for 1 hour at the end of which time the cloth is removed, rinsed and dried. A reddish-violet shade of good Wash fastness is obtained.
  • Example 1 The procedure of Example 1 is followed except that methylcyclohexylaminopropylamine is used in equivalent quantity instead of dimethylaminopropylamine.
  • Alpha-amino anthraquinone beta sulfonamides having no other ring substituents in which the amino group is on a different ring from the sulfonamide; the said amino group being selected from the group consisting of free amino groups, amino groups substituted by lower alkyl radicals and amino groups substituted by a cyclohexyl radical; the said sulfonamide group being a substituted sulfonamide in which the substituting group is a quaternary ammonium alkylene group, the said quaternary ammonium group having three substituents selected from the group consisting of lower alkyl and cyclohexyl, at least two of which are lower alkyl.

Description

(1 -ALKYLAMINO 6 (7) ANTHRAQUINONYL- SULFONAMIDO)ALKYL TRIALKYLAMMONIIM SALI'IIS AS DISPERSE DYES FOR ACRYLIC FIB RS Asa Willard Joyce, Plainfield, N. assign'or to American Cyanamid Company, New York, N.Y., a corporation 'of Maine No Drawing. Original application Sept. 25, 1957, Ser. No. 686,048. Divided and this application Aug. 4, 1958, Ser. No. 753,124
8 Claims. (Cl. 260-371) .the said amino group being, when not free amino, substituted by an aliphatic group which, when not lower alkyl, is cyclohcxyl; the said sulfonamide group being a substituted sulfonamide in which the substituting group is a quaternary ammonium alkylene group, the said quaternary ammonium group having three substituents, at least two of which are lower alkyl and the other, when not lower alkyl, being cyclohexyl.
This application is a division of my copending applicaton, Serial No. 686,048, filed September 25, 1957, now abandoned.
The polyacrylonitrile fibers, which have become increasingly useful articles of commerce, are diflicult to dye. Most of the commercially available fibers of this type contain a major proportion of polyacrylonitrile. In most cases over 85% of the fiber is acrylonitrile. Few of the standard dyestuffs available show afiinity for these high acrylonitrile content fibers. Especially it has been hard to obtain deep shades on these fibers since deep shades require a strong aifinity of the fiber for the dyestuif. The only way to achieve deep shades has been to increase the time and temperatures of the dyeing process. Such drastic conditions of dyeing result in injury to the fabrics. The resistant properties of these fibers are desirable for general textile use because they render the fiber physically durable. However, the problem of dyeing has been so great that these durable types may have to be superseded by more dyeable types which are less durable physically unless methods of-dyeing them readily are found. The usual disperse dyes have little or no aflinity for fibers made of polyacrylonitrile. Those basic dyes which do dye fibers of this type give dyes of poor fastness to light and in addition, such dyes usually need dispersing or solubilizing agents to form the dyebath.
I have found, that cationic anthraquinone dyes of the.
formula:
R",NH h) V /R V SO2-NH-(CH2)-ll A- R R r t in which R" is hydrogen or alkyl of less than seven carbon atoms, R is lower alkyl, R is lower alkyl or cyclohexyl; n is an integer from 2 to 4 and A- is an anion, have excellent affinity for polyacrylonitrile fibers with major ingly' soluble in water, dyeing acrylic fibers with major proportion of acrylonitrile with great ease by the usual disperse methods.
The dyes of my invention are usually prepared from 2,938,914 Patented May 31,
2 l-nitro-6-anthraquinonesulfonyl chloride, 1 nitro 7 anthraquinonesulfonyl chloride or mixtures of the two isomers. The sulfonyl chloride group is reacted with an alkylated alkylene diamine after which the nitro group is replaced by an amino or a substituted amino. The quaternizable dye thus formed is then quaternized to form the cationic anthraquinone disperse dyes of my invention. These reactions can be shown by the following equation:
can be placed on the amino group, such as propyl butyl and hexyl. Similarly, the alkyl groups need not' be the same so that one can use methylethylaminoethylamine o methylethylaminopropylamine and the like.
Thenitro group may be replaced with ammonia to give the free amine or with a lower alkyl amine such as methylamine, ethylamine, butylamine, isobutylamine, isopropylamine, tert-butylamine or with cyclohexylamine. The quaternization is eifected by reaction with a compound of the general formula RA in which R is the quaternizing group and A is the anion which may contain an alkyl or other organic residue. The following quaternizing agents may be used: dialkyl sulfates, such as dimethyl sulfate, diethyl sulfate, dipropyl sulfate or dibutyl sulfate; alkyl halides such as methyl iodide, ethyl iodide, methyl chloride, ethyl chloride, butyl bromide, hexyl bromide, and the like, aralkyl halides such as benzyl chloride, phenylethylbromide and the like or alkyl esters of aryl sulfonic acids such as the methyl, ethyl, propyl or butyl esters of para-toluene sulfonic acid or substituted alkyl halides such as ethylene chlorohydrin, propylene chlorohydrin and the like, or alkenyl halides such as alkyl brornide Usually it is preferredthat the quatemizingagents contain the lower alkyl groups such as methyl and ethyl, as these are the preferred guaternizing groups.
Polyacrylonitriles which may be dyed with the compound of my invention. and which fall within the scope of my invention are those polymers and copolymers of acrylonitrile which contain a major proportion by weight of acrylonitrile, they may also contain basic comonomers as methyl vinyl pyridine and vinyl pyridine or comonomer-s such as methyl acrylatc, vinyl acetate and vinyl chloride. .Of the polyacrylonitriles available commercially which can be used to form the colored polyacrylonitriles of my invention, one is 100% polyacrylonitrile, another is approximately 95% acrylonitrile and approximately 5% methyl acrylate, another'has 89% of acrylonitrile, 6% methyl vinyl pyridine and 5% vinyl acetate, and still another has a composition of 94% acrylonitrile, 5% methyl vinyl pyridine and 1% vinyl acetate. Polymers having as little as 50% acrylonitrile can be dyed by the class of dyes of my invention to form the dyed fibers of my invention.
It is an advantage of my invention that the new dyes which I have invented are surprisingly soluble in water and dye acrylic fibers having a major proportion of acrylonitrile with ease by the usual disperse dyeing methods. The preferred method of application is at the boil in an aqueous dye bath which is neutral to weakly alkaline, although fibers can also be dyed in an acidic medium.
It is a further advantage of our invention that the dyes are orange .red to red violet shades of good fastness to washing. For example, the dyestuff of the formula:
a s- 1 l Example 1 Cfil -NH CH1 Oa-NH-OH1OHg-CHr-N CHaSOr I CH: 0
To 10.6 parts of 1-nitro-6-anthraquinony1sulfonyl chlo- 4 aminopropylaminosulfonyl anthraquinone thus prepared is further purified by grinding to a smooth paste with water, diluting with parts of water and adjusting the alkalinity with about 3 parts by weight of sodium carbonate until alkaline to phenolphthalein indicator paper. After stirring in this alkaline medium, the product isagain isolated by filtration, washed free from alkali with water, followed by a small methanol wash, and dried.
A mixture of 6.3 parts by weight of the above product, 75 parts by volume of toluene, and 4.1 parts by volume of 70% ethylamine is gradually warmed to C. The mixture is heated at 85-95 C. until the reaction is complete. The partially precipitated product is isolated by evaporation and dried. The product is l-ethylamino- 6-dimethylaminopropylaminosulfonyl anthraquinone.
3.1 parts of the above product is dissolvedin parts I by volume of orthodichlorobenzene by heating at reflux. The solution is then cooled to 50 C. and 1.35 parts of dimethyl sulfate solution added. The reaction mixture 7 C. for a shorttime (one half hour when parts are grams), and then held at about 85 C. until quaternization is complete. The mixture is then cooled to 50 C. and the product is isolated by filtration. It is then ground and reslurried in orthodichloro benzene and again filtered and washed with orthodichlorobenzene, followed by benzene, and dried. The product has the above structure.
is then warmed to 100 Example 2 CzHs-NH O I H CH5 SOz-NHCH CHrCHrN I H CH: 0
2.7 parts of the product of Example 1 in 100 parts by volume of water are treated with 10 parts of potassium iodide. The sulfate anion is thus replaced by an iodide anion. The product is isolated by filtration.
If in Example 1 the ethylamine is replaced with 1.4 parts of methylamine, a corresponding cationic anthraquinone dyestuflf of the above formula is obtained which dyes polyacrylonitrile fibers having a high acrylonitrile content reddish-violet shades.
Example 4 CHaCHzCILCHg-NH 0 02H soiNn-omomomonr-r r cnnsor i 1 02 5 0 10.6 parts of 1-nitro-G-anthraquinonylsulfonyl chloride are slurried in 75 parts by volume of benzene. To this is added 8.7 parts of diethylaminobutylamine and the 70 mixture warmed at 50 C. until reaction is complete.
The product (1-nitro-6-diethylaminobutylaminosulfonyl anthraquinone) is isolated by filtration and washed with benzene.
This product is then mixed with parts by volume of 75 toluene and 7.3 parts of butylamine is added. The mixa ma ture is heated at 85-95 C. until the nitro group is substantially replaced by butylamino groups. The product is isolated by evaporation.
The product obtained (l-butylamino-G-diethylaminobutylaminosulfonyl anthraquinone) is added to 200 parts by volume of orthodichlorohenzene and heated at reflux until dissolved. To this solution is added 6.1 parts of diethyl sulfate and the mixture is heated at 85 C. until quaternization is complete. The product of the formula above is then isolated by filtration, washed with orthodichlorobenzene and dried. It dyes acrylonitrile polymers, both those with basic comonomers and from weakly alkaline baths, reddishwiolet shades.
To 10.6 parts of 1-nitro-6-anthraquinonylsulfonyl chloride in 75 parts by volume of benzene at 15-20 C. is added 5.3 parts of dimethylaminoethylamine in 25 parts by volume of benzene. The mixture is warmed at 50 C. until replacement of the chlorine in complete. The reaction mixture is then cooled, filtered and the product Washed with benzene and dried.
The product is added to 150 parts by volume of toluene. To this is added 8.9 parts of cyclohexylamine and the mixture heated at 85-95 C. until the nitro group is substantially replaced with a cyclohexylamino group. The product is isolated by evaporation and quaternized using an excess (about 2.6 parts) of ethyl chloride, using the solvent and quaternization method of Example 4. The reaction mixture is cooled to 50 C. and filtered. The product is washed with orthodichlorobenzene and dried. It dyes acrylic fibers having a high acrylonitrile content reddish-violet shades.
Example 6 Chin-NH I ll SOBNHmmcHZGm-FJ omso;
. CHs CH: (lg
If in Example 1, 10.6 parts of 1-nitro-6-anthraquinony1- sulfonyl chloride are replaced by the same amount of 1-nitro-7-anthraquinonylsulfonyl chloride, 21 water soluble cationic dyestutf is obtained which dyes Orlon a violet shade, which is somewhat redder than the dye produced in Example 1.
Example 7 H: The procedure of Example 1 is followed except that the second step (replacement of the nitro group by ethylamine) is carried out in o-dichlorobeuzene instead of toluene (in equal amount) by passing ammonia gas through the solution, the mixture being held at 160 C. and the ethylamine being omitted. The final product is the dye of the above structure which dyes acrylic fibers a bright orange red.
Example 9 Acrylic fibers may be dyed with the dyes of the preced ing examples by the following preferred procedure: To a dye bath is added a piece of acrylic cloth consisting of between -l00% acrylonitrile plus 40 parts of water per unit weight of the fabric and one part by weight of the dyestuff of Example 1 and 1 part by weight of sodium carbonate solution. The dye bath is boiled for 1 hour at the end of which time the cloth is removed, rinsed and dried. A reddish-violet shade of good Wash fastness is obtained.
If a fabric composed of acrylonitrile and 5% methyl acrylate is used, a similar result is obtained. Also, a similar but slightly deeper shade is obtained with a fiber consisting of 88.7% acrylonitrile, 6.3% methyl vinyl pyridine and 5% vinyl acetate.
Example 10 C2H5NH O CHa SO2NH-CH2CHzCH -N CHgSO; CH: 0
re r r CH2 CH The procedure of Example 1 is followed except that methylcyclohexylaminopropylamine is used in equivalent quantity instead of dimethylaminopropylamine.
I claim:
1. Alpha-amino anthraquinone beta sulfonamides having no other ring substituents in which the amino group is on a different ring from the sulfonamide; the said amino group being selected from the group consisting of free amino groups, amino groups substituted by lower alkyl radicals and amino groups substituted by a cyclohexyl radical; the said sulfonamide group being a substituted sulfonamide in which the substituting group is a quaternary ammonium alkylene group, the said quaternary ammonium group having three substituents selected from the group consisting of lower alkyl and cyclohexyl, at least two of which are lower alkyl.
2. [3 (1 ethylamino 6 anthraquinonylsulfonamido)-propyl]-trimethylammonium methyl sulfate.
3. [3 (1 ethylamino 6 anthraquinonylsulfonamido) propyl] -trimethylammonium iodide.
4. [3 (1 methylamino 6 anthraquinonylsulfonamido) -propyl] -trimethylammonium methyl sulfate.
5. [4 (1 butylamino 6 anthraquinonylsulfonamido) -butyl] -triethylammonium ethyl sulfate.
6. [2 (1 cyclohexylamino 6 anthraquinonylsulfonamido) -ethyl] -ethyldimethyl ammonium chloride.
7. [3 (1 ethylamino 7 anthraquinonylsulfonamido) -propyl] -trimethylammonium methyl sulfate.
8. [3 (1 amino 6 anthraquinonylsulfonamido)- propyll-trimethylammonium methyl sulfate.
References Cited in the file of this patent UNITED STATES PATENTS 2,371,101 Kienle et a1 Mar. 6, 1945 FOREIGN PATENTS 1,140,531 France Mar. 4, 1957 Patent should f major" read fibers and are surpris- UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 2,338,914 May 31, 1960 Asa Willard Joyce It is hereby certified the t error appears in the printed specification of the above numbered patent re quiring correction and that the said Letters readas corrected below.
Column 1, fourth line below the formula for "fibers with Signed and sealed this 1st day of November 1960.
SEAL) ttest: ARL H. AXLINE ROBERT C. WATSON ttesting Oflicer Commissioner of Patents

Claims (1)

1. ALPHA-AMINO ANTHRAQUINONE BETA SULFONAMIDES HAVING NO OTHER RING SUBSTITUENTS IN WHICH THE AMINO GROUP IS ON A DIFFERENT RING FROM THE SULFONAMIDE, THE SAID AMINO GROUP BEING SELECTED FROM THE GROUP CONSISTING OF FREE AMINO GROUPS, AMINO GROUPS SUBSTITUTED BY LOWER ALKYL RADICALS AND AMINO GROUPS SUBSTITUTED BY A CYCLOHEXYL RADICAL, THE SAID SULFONAMIDE GROUP BEING A SUBSTITUTED SULFONAMIDE IN WHICH THE SUBSTITUTING GROUP IS A QUATERNARY AMMONIUM ALKYLENE GROUP, THE SAID QUATERNARY AMMONIUM GROUP HAVING THREE SUBSTITUENTS SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL AND CYCLOHEXYL, AT LEAST TWO OF WHICH ARE LOWER ALKYL.
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US3256275A (en) * 1961-02-16 1966-06-14 Basf Ag Phthalocyanine dyes
US4264511A (en) * 1978-05-13 1981-04-28 Bayer Aktiengesellschaft Anthraquinone compounds
US4276224A (en) * 1978-06-07 1981-06-30 Ciba-Geigy Corporation Anthraquinone sulphonamide compounds and preparation
US6359052B1 (en) 1997-07-21 2002-03-19 Jack Wesley Trexler, Jr. Polyester/platelet particle compositions displaying improved dispersion
US6384121B1 (en) 1998-12-07 2002-05-07 Eastman Chemical Company Polymeter/clay nanocomposite comprising a functionalized polymer or oligomer and a process for preparing same
US6486254B1 (en) 1998-12-07 2002-11-26 University Of South Carolina Research Foundation Colorant composition, a polymer nanocomposite comprising the colorant composition and articles produced therefrom
US6486252B1 (en) 1997-12-22 2002-11-26 Eastman Chemical Company Nanocomposites for high barrier applications
US6486253B1 (en) 1999-12-01 2002-11-26 University Of South Carolina Research Foundation Polymer/clay nanocomposite having improved gas barrier comprising a clay material with a mixture of two or more organic cations and a process for preparing same
US6548587B1 (en) 1998-12-07 2003-04-15 University Of South Carolina Research Foundation Polyamide composition comprising a layered clay material modified with an alkoxylated onium compound
US6552114B2 (en) 1998-12-07 2003-04-22 University Of South Carolina Research Foundation Process for preparing a high barrier amorphous polyamide-clay nanocomposite
US6552113B2 (en) 1999-12-01 2003-04-22 University Of South Carolina Research Foundation Polymer-clay nanocomposite comprising an amorphous oligomer
US6586500B2 (en) 2000-05-30 2003-07-01 University Of South Carolina Research Foundation Polymer nanocomposite comprising a matrix polymer and a layered clay material having an improved level of extractable material
US6596803B2 (en) 2000-05-30 2003-07-22 Amcol International Corporation Layered clay intercalates and exfoliates having a low quartz content
US6610772B1 (en) 1999-08-10 2003-08-26 Eastman Chemical Company Platelet particle polymer composite with oxygen scavenging organic cations
US6653388B1 (en) 1998-12-07 2003-11-25 University Of South Carolina Research Foundation Polymer/clay nanocomposite comprising a clay mixture and a process for making same
US20040063841A1 (en) * 1998-12-07 2004-04-01 Gilmer John Walker Process for preparing an exfoliated, high I. V. polymer nanocomposite with an oligomer resin precursor and an article produced therefrom
US20040127627A1 (en) * 1998-12-07 2004-07-01 Gilmer John Walker Polymer/clay nanocomposite comprising a clay treated with a mixture of two or more onium salts and a process for making same
US6777479B1 (en) 1999-08-10 2004-08-17 Eastman Chemical Company Polyamide nanocomposites with oxygen scavenging capability
US20050159526A1 (en) * 2004-01-15 2005-07-21 Bernard Linda G. Polymamide nanocomposites with oxygen scavenging capability

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3256275A (en) * 1961-02-16 1966-06-14 Basf Ag Phthalocyanine dyes
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