Stock material or miscellaneous articles – Coated or structually defined flake – particle – cell – strand,... – Rod – strand – filament or fiber
Reexamination Certificate
2000-02-11
2001-11-06
Acquah, Samuel A. (Department: 1711)
Stock material or miscellaneous articles
Coated or structually defined flake, particle, cell, strand,...
Rod, strand, filament or fiber
C528S272000, C528S288000, C528S293000, C528S302000, C525S437000, C525S444000, C525S540000, C560S001000, C560S147000, C562S400000, C562S512000, C562S552000
Reexamination Certificate
active
06312805
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to a cationic dyeability modifier that provides improved basic dyeability for polyesters and polyamides. The invention also relates to a basic dyeable copolyester derived from polyesters such as poly(alkylene terephthalates) and to a basic dyeable copolyamide derived from polyamides such as nylon 6 and nylon 66. The modified polyester and modified polyamide are suitable for use in manufacturing fibers, filaments and other useful articles.
BACKGROUND OF THE INVENTION
Polyesters, especially polyalkylene terephthalates, and polyamides, especially nylon 6 and nylon 66, have excellent physical and chemical properties and have been widely used for resins, films and fibers. In particular, polyester and polyamide fibers have relatively high melting points, and can attain high orientation and crystallinity. Accordingly, polyesters and polyamides have excellent fiber properties such as chemical, heat and light stability, and high strength.
However, polyesters, especially polyester fibers, are difficult to dye. The molecular structure and the high levels of orientation and crystallinity that impart desirable properties to the polyester also contribute to a resistance to coloration by dye compounds. Also contributing to the difficulty in dyeing polyester is the characteristics that polyesters, unlike protein fibers, do not have dye sites within the polymer chain that are reactive to basic or acid dye compounds. Although polyamides are not as difficult to dye as polyesters, one or more dyeability additives are nevertheless commonly incorporated into polyamides, e.g., in order to selectively increase the affinity of the polyamide fibers for certain types of dyes, e.g., acidic or basic, or to selectively increase the resistance of the fibers to staining with certain types of staining agents.
It is known that that certain materials, such as aromatic sulfonates and their sodium salts, including the sodium salt of 5-sulfoisophthalic acid or the sodium salt of dimethyl 5-sulfoisophthalate, can be copolymerized with the polyester or polyamide as a means of conferring basic dyeability. Other cationic dyeability modifiers have also been disclosed. For example, Sakurai, U.S. Pat. No. 3,313,778, discloses a modified polyester which has linked to the main chain thereof a minor proportion of at least one organo sulfonic acid ester having the formula (X—SO
2
—O)
n
—Y, where n is an integer from 1 to 4; X is, e.g., an alkyl group of 1 to 12 carbon atoms; and Y is, e.g., a lower alkyl group, having one or two ester-forming functional groups, for example beta-carbomethoxyethyl methanesulfonate.
Further, poly(trimethylene terephthalate) has many properties that make it desirable for use in manufacturing fibers for textile applications, including improved recovery and resilience, as compared with poly(ethylene terephthalate). However, cationic dyeability modifiers that are particularly useful for improving the basic dyeability of poly(trimethylene terephthalate) have not been proposed.
It is desireable to provide a cationic dyeability modifier which can be incorporated into polyesters, especially poly(alkylene terephthalate), and polyamides, especially nylon 6 and nylon 66, to confer improved basic dyeability and which can be produced at lower cost than conventional cationic dyeability modifiers.
It is also desirable to provide a basic dyeable polyester, in particular poly(alkylene terephthalate), and more particularly poly(trimethylene terephthalate), which can be easily processed into fibers, films or other shaped articles and basic-dyed without the use of expensive cationic dyeability modifiers or additives, special solutions, and/or complicated application procedures.
It is also desireable to provide a basic dyeable polyamide, in particular nylon 6 or nylon 66, which can be easily processed into fibers, films or other shaped articles and basic-dyed without the use of expensive cationic dyeability modifiers or additives, special solutions, and/or complicated application procedures. The present invention provides such a cationic dyeability modifier and basic dyeable polyester and polyamide.
SUMMARY OF THE INVENTION
The invention comprises a cationic dyeability modifier for incorporation into polyesters and polyamides to increase their affinity for basic dyes, said cationic dyeability modifier having the following formula:
R
1
OOC—(CH
2
)
n
—CH(CH
2
CH
2
SO
3
X)—(CH
2
)
m
—COOR
2
where n is an integer from 1 to 10, m is an integer from 1 to 10, X is an alkali metal selected from the group consisting of lithium, sodium and potassium, and R
1
and R
2
are independently selected from hydrogen and alkyl groups having one to four carbon atoms.
The invention further comprises a basic dyeable copolymer selected from the group consisting of copolyesters and copolyamides, wherein said copolymer comprises a comonomer of the formula:
R
1
OOC—(CH
2
)
n
—CH(CH
2
CH
2
SO
3
X)—(CH
2
)
m
—COOR
2
where n is an integer from 1 to 10, m is an integer from 1 to 10, X is an alkali metal selected from the group consisting of lithium, sodium and potassium, and R
1
and R
2
are independently selected from hydrogen and alkyl groups having one to four carbon atoms, and wherein said comonomer is incorporated into the polymer chain of said copolymer in an amount sufficient to improve its affinity for basic dyes.
The invention further comprises a process for preparing a basic dyeable copolyester comprising the steps of: (a) combining one or more materials selected from the group consisting of poly(alkylene terephthalate)-forming monomers and polyoxyalkylene glycol oligomers with a comonomer of the formula:
R
1
OOC—(CH
2
)
n
—CH(CH
2
CH
2
SO
3
X)—(CH
2
)
m
—COOR
2
where n is an integer from 1 to 10, m is an integer from 1 to 10, X is an alkali metal selected from the group consisting of lithium, sodium and potassium, and R
1
and R
2
are independently selected from hydrogen and alkyl groups having one to four carbon atoms; and (b) mixing and heating said materials and said comonomer at a temperature sufficient to cause copolymerization to form a copolyester containing said comonomer in an amount sufficient to improve its affinity for basic dyes.
DETAILED DESCRIPTION OF THE INVENTION
The cationic dyeability modifier of the invention is an aliphatic sulfonate of the following formula:
R
1
OOC—(CH
2
)
n
—CH(CH
2
CH
2
SO
3
X)—(CH
2
)
m
—COOR
2
I
where n is an integer from 1 to 10, m is an integer from 1 to 10, X is an alkali metal selected from lithium, sodium and potassium, and R
1
and R
2
are independently selected from hydrogen and alkyl groups having one to four carbon atoms. The preferred cationic dyeability modifier is 3-(2-sulfoethyl)hexanedioic acid, sodium salt, which has the following formula:
HOOC—(CH
2
)—CH(CH
2
CH
2
SO
3
Na)—(CH
2
)
2
—COOH II
and its dimethyl ester, namely dimethyl-3-(2-sulfoethyl)adipate, sodium salt, which has the following formula:
H
3
COOC—(CH
2
)—CH(CH
2
CH
2
SO
3
Na)—(CH
2
)
2
—COOCH
3
III
3-(2-Sulfoethyl)hexanedioic acid, sodium salt is prepared by addition
reaction of 4-vinyl cyclohexene and formic acid in the presence of hydrogen peroxide to form a mixture of 4-vinylcyclohexane 1,2-diformate, 4-vinylcyclohexane 1-monoformate, and 4-vinylcyclohexane 2-monoformate, followed by a hydrolysis with sodium hydroxide and then an addition reaction with sodium bisulfite and sodium persulfate in the presence of sodium hydroxide to form the sodium salt of 4-(2-sulfoethyl)cyclohexane-1,2-diol, followed by oxidation in the presence of tungstic acid and hydrogen peroxide to form 3-(2-sulfoethyl)hexanedioic acid, sodium salt, as set forth in greater detail in Examples I to III. Dimethyl-3-(2-sulfoethyl) adipate, sodium salt is prepared from 3-(2-sulfoethyl) hexanedioic acid, sodium salt by reaction with anhydrous methanol, as described in greater detail in Example IV.
The cationic dyeability modifier of formula I is incorporated into the polymer chain of a polyester or polyamide to provide dye sites for basic dyes. Polyester and pol
Acquah Samuel A.
E.I. Du Pont de Nemours and Company
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