Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From reactant having at least one -n=c=x group as well as...
Reexamination Certificate
2002-07-15
2003-12-09
Gorr, Rachel (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From reactant having at least one -n=c=x group as well as...
C528S084000, C528S906000, C528S298000, C528S307000, C528S354000, C560S084000, C428S364000, C252S182240
Reexamination Certificate
active
06660825
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a spandex filament (a polyurethane elastic filament), which is excellent in a recovering ability of elasticity, high tensile strength, hydrolysis resistance, and heat resistance, and a polyurethane to provide the spandex filament and, further, relates to a lactone polyester diol to be used for the polyurethane.
BACKGROUND OF THE INVENTION
A polyurethane having a linear structure is obtained by allowing to react an organic diisocyanate with a long chain diol having hydroxyl groups at both terminals and a relatively low molecular weight diol or diamine having two active hydrogens, which diol or diamine is named a chain extender.
Various proposals have been made for improving a recovering ability of elasticity and hydrolysis resistance in the thus-obtained polyurethane.
As described in JP-A-58059212 Official Gazette, a polyurethane in which a polyethylene glycol adipate polyester is employed is excellent in a recovering ability of elasticity. However, it is poor in hydrolysis resistance.
Further, although a 1,4-butylene glycol adipate polyester has a certain extent of hydrolysis resistance, a polyurethane therefrom is poor in a recovering ability of elasticity. Still further, although a polyurethane obtained from a polycaprolactone polyol is excellent in hydrolysis resistance, weatherability, and heat resistance, it is poor in a recovering ability of elasticity.
As a method for solving a drawback of a polycaprolactone-based polyurethane, the Official Gazette discloses a technology using a specified polycaprolactone polyester polyol obtained by a transesterification reaction of a polyester polyol synthesized by a dehydration esterification of neopentylglycol and adipic acid with &egr;-caprolactone.
However, the polyurethane described in the Official Gazette does not always exhibit sufficient recovering ability of elasticity and hydrolysis resistance, and therefore, there has been desired a polyurethane in which those properties are further improved.
Further, JP-A-11001822 Official Gazette discloses polyurethane elastic filaments which are excellent in hydrolysis resistance in alkali, in which there are employed 2-n-butyl-2-ethyl-1,3-propane diol and 2,2-diethyl-1,3-propane diol, or the like, as diol components which constitute a polyester polyol.
However, although the polyurethane elastic filaments in the Official Gazette are excellent in hydrolysis resistance in alkali, it has been desired to further improve a recovering ability of elasticity and strength.
Still further, JP-A-11189637 Official Gazette discloses a polyurethane obtained by polyaddition reaction of a polyol compound with a polyisocyanate compound, in which the polyol compound is partially or completely comprised of a polyester polyol which has recurring units represented by general formula (i) and which has a hydroxyl group value of 10-200 and, moreover, 10-100% of residual groups A in the polyester polyol are a residual group of a diol represented by general formula (ii) or (iii).
—[—O—A—O—C(═O)—B—C(═O)—]— (i)
(in the formulae, R
1
represents an alkyl group or phenyl group having a carbon number of 1-4, R
2
is a hydrogen atom or a methyl group, and X represents a single bond or double bond)
However, the polyurethane disclosed in the Official Gazette includes problems that it is very rigid and poor in a recovering ability of elasticity.
Purpose of the present invention is to provide a spandex filament (a polyurethane elastic filament) which is excellent in a recovering ability of elasticity, strength, hydrolysis resistance, and heat resistance, and to provide a polyurethane to prepare thereof and, further, to provide a polyester diol to be used for the polyurethane.
The present inventor has found that the above-described problems can be solved by using a polyester diol obtained from a specific alicyclic diol, &egr;-caprolactone, and a dibasic acid, as starting materials for the polyurethane, and the present invention has been completed.
SUMMARY OF THE INVENTION
That is, a first aspect of the present invention provides a polyurethane obtained by an organic diisocyanate and a lactone polyester diol obtained by the use of constructing component units comprising at least one of diol (A) selected from diols represented by formulae (1) and (2), &egr;-caprolactone (B), and a dibasic acid (C),
[in the formulae (1) and (2), bonds constructing the ring may be partially even a double bond, and R
1
represents an alkyl group or phenyl group having a carbon number of 1-4, and R
2
represents a hydrogen atom or a methyl group].
A second aspect of the present invention provides a lactone polyester diol described in the first aspect of the present invention wherein the dibasic acid (C) is an aliphatic dicarboxylic acid and/or aromatic dicarboxylic acid.
A third aspect of the present invention provides a lactone polyester diol described in the first aspect of the present invention wherein the dibasic acid (C) is adipic acid, glutaric acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanoic diacid, 1,11-undecane dicarboxylic acid, terephthalic acid, isophthalic acid, or 5-sulphosodium isophthalic acid, or a mixture thereof.
A fourth aspect of the present invention provides a lactone polyester diol described in the first to third aspects of the present invention wherein a number average molecular weight ranges in 500-5000.
A fifth aspect of the present invention provides a lactone polyester diol claimed in any one of the first to forth aspects of the present invention wherein the content of constructing unit composed of the diols (A) and the dibasic acid (C) in the polyester ranges in 5/95 to 80/20 (weight ratio) with respect to the content of &egr;-caprolactone (B) unit.
A sixth aspect of the present invention provides a polyurethane obtained from the lactone polyester diol described in the first to fifth aspects of the present invention and an organic diisocyanate.
A seventh aspect of the present invention provides a spandex filament which comprises the polyurethane described in the sixth aspect of the present invention.
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention is illustrated in detail.
<Diol (A)>
The diol (A) employed in the present invention is a diol having a specified alicyclic structure, and it is at least one of diols selected from diols represented by formulae (1) and (2) described below. The alicyclic structure includes a cyclohexane ring or a norbornane ring, or the like.
In the formulae (1) and (2), R
1
represents an alkyl group having a carbon number of 1-4, preferably, methyl group or ethyl group and, further, R
2
may be even any one of a hydrogen atom or a methyl group.
The diol (A) includes a compound having 1,1-cyclohexane dimethanol structure in which 2-position is substituted by an alkyl group or phenyl group having a carbon number of 1-4; a compound having 2,2-norbornane dimethanol structure in which 3-position is substituted by an alkyl group or phenyl group having a carbon number of 1-4; a compound having 3-cyclohexene-1,1-dimethanol structure in which 6-position is substituted by an alkyl group or phenyl group having a carbon number of 1-4; or a compound having 5-norbornene-2,2-dimethanol structure in which 3-position is substituted by an alkyl group or phenyl group having a carbon number of 1-4.
Specifically, it includes 2-methyl-1,1-cyclohexane dimethanol, 2-ethyl-1,1-cyclohexane dimethanol, 2-propyl-1,1-cyclohexane dimethanol, 2-butyl-1,1-cyclohexane dimethanol, 2-phenyl-1,1-cyclohexane dimethanol, 2,3-dimethyl-1,1-cyclohexane dimethanol, 2,4-dimethyl-1,1-cyclohexane dimethanol, 2,5-dimethyl-1,1-cyclohexane dimethanol, 2,6-dimethyl-1,1-cyclohexane dimethanol, 3-methyl-2,2-norbornane dimethanol, 3-ethyl-2,2-norbornane dimethanol, 3-propyl-2,2-norbornane dimethanol, 3-butyl-2,2-norbornane dimethanol, 3-phenyl-2,2-norbornane dimethanol, 6-methyl-3-cyclohexene-1,1-dimethanol, 6-ethyl-3-cyclohexene-1,1-dimethanol, 6-propyl-3-cyclohexene-1,1-dimethanol, 6-buty
Daicel Chemical Industries, LTD
Gorr Rachel
Morgan & Finnegan L.L.P.
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