WO1999010573B1 - Improved copolymer binder fibers - Google Patents

Improved copolymer binder fibers

Info

Publication number
WO1999010573B1
WO1999010573B1 PCT/US1998/017813 US9817813W WO9910573B1 WO 1999010573 B1 WO1999010573 B1 WO 1999010573B1 US 9817813 W US9817813 W US 9817813W WO 9910573 B1 WO9910573 B1 WO 9910573B1
Authority
WO
WIPO (PCT)
Prior art keywords
copolyester
mole
binder fiber
dicarboxylic acid
ppm
Prior art date
Application number
PCT/US1998/017813
Other languages
French (fr)
Other versions
WO1999010573A1 (en
Inventor
Leron R Dean
William A Haile
Michael D Lambert
F Henry Dillow
Mark E Tincher
Original Assignee
Eastman Chem Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Chem Co filed Critical Eastman Chem Co
Priority to CA002301522A priority Critical patent/CA2301522A1/en
Priority to JP2000507874A priority patent/JP2001514336A/en
Priority to DE69836223T priority patent/DE69836223T2/en
Priority to EP98944567A priority patent/EP1015674B1/en
Publication of WO1999010573A1 publication Critical patent/WO1999010573A1/en
Publication of WO1999010573B1 publication Critical patent/WO1999010573B1/en

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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
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/44—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/46—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polyolefins
    • D—TEXTILES; PAPER
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    • D—TEXTILES; PAPER
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    • D01F6/82—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from polyester amides or polyether amides
    • D—TEXTILES; PAPER
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    • D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
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    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
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    • D01F8/14—Conjugated, i.e. bi- or multicomponent, artificial filaments or the like; Manufacture thereof from synthetic polymers with at least one polyester as constituent
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    • D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
    • D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
    • D04H1/4282—Addition polymers
    • D04H1/4291—Olefin series
    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
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    • D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
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    • D04H1/4326—Condensation or reaction polymers
    • D04H1/435—Polyesters
    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
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    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
    • D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
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    • D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
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    • D04H1/43832—Composite fibres side-by-side
    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
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    • D04H1/43835—Mixed fibres, e.g. at least two chemically different fibres or fibre blends
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    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
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    • D04H1/52—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties the fleeces or layers being consolidated by mechanical means, e.g. by rolling by applying or inserting filamentary binding elements
    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
    • D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
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    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
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    • D04H1/60—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in dry state, e.g. thermo-activatable agents in solid or molten state, and heat being applied subsequently
    • D04H1/62—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in dry state, e.g. thermo-activatable agents in solid or molten state, and heat being applied subsequently at spaced points or locations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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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
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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    • 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
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    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]

Abstract

The invention relates to binder fibers made from copolyester, the copolyesters themselves and catalysts and processes for producing the copolyesters. More particularly, the invention relates to copolyesters formed from 1,4-cyclohexanedimethanol, ethylene glycol and terephthalic acid, napthalenedicarboxylic acid, 1,4-cyclohexane dicarboxylic acid and esters or anhydrides thereof. Such copolyesters may be formed into a variety of products, especially binder fibers for nonwoven fabrics.

Claims

[received by the International Bureau on 2 April 1999 (02.04.99); original claims 1, 7, 18 and 23 amended; new claims 26-28 added; remaining claims unchanged (4 pages)]
1. A binder fiber comprising a copolyester formed from the reaction product of: a glycol component with a dicarboxylic acid component, wherein the glycol component comprises 1,4-cyclohexanedimethanol in an amount ranging from about 10 to about 60 mole % and ethylene glycol in an amount ranging from about 40 to about 90 mole %, wherein at least about 90 mole % of the dicarboxylic acid component is selected from the group consisting of acids, esters and anhydrides of terephthalic acid, naphthalenedicarboxylic acid, 1 ,4-cyclohexanedicarboxylic acid and mixtures thereof, and wherein the copolyester has an IN. of between about 0.36 to 0.58.
2. The binder fiber of claim 1, wherein at an activation temperature of less than about 275 °F, the binder fiber possesses superior bonding strength when compared to a binder fiber formed from a copolyester having an IN. of 0.6 or higher.
3. The binder fiber of claim 1 , wherein the binder fiber may be activated by ultrasonic and radio frequencies.
4. The binder fiber of claim 1 wherein the binder fiber has a denier ranging from about 1 to about 20.
5. The binder fiber of claim 1 wherein the binder fiber is a unicomponent binder fiber.
6. The binder fiber of claim 1 wherein the binder fiber is a bicomponent binder fiber.
7. A copolyester comprising the reaction product of: a glycol component with a dicarboxylic acid component, wherein the glycol component comprises 1 ,4-cyclohexanedimethanol in an amount ranging from about 10 to about 60 mole % and ethylene glycol in an amount ranging from about 40 to about 90 mole %, wherein at least about 90 mole % of the dicarboxylic acid component is selected from the group consisting of acids, or esters or anhydrides of terephthalic acid, naphthalenedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid and
2 8 mixtures thereof, and wherein the copolyester has an IN. of between about 0.36 to 0.58 and an L* value of greater than about 65.
8. A copolyester according to claim 7, wherein the L* value is greater than about 65 and the b* value ranges from about -2.5 to about +2.5.
9. A copolyester according to claim 7, wherein the dicarboxylic acid component is an ester or mixture of esters of terephthalic acid, napthalenedicarboxylic acid or 1,4-cyclohexane dicarboxylic acid.
10. A copolyester according to claim 7, wherein the copolyester is formed in the presence of a catalyst system comprising about 10 to about 35 ppm Ti, about 30 to about 70 ppm Mn, about 0 to about 90 ppm Co and in the presence of a catalytic inhibitor comprising about 40 to about 90 ppm P based on the weight of the copolyester.
11. A copolyester according to claim 7, further comprising an additional dicarboxylic acid component in an amount of up to 10 mole % of the dicarboxylic acid component, wherein the additional dicarboxylic acid component is selected from the group consisting of aromatic dicarboxylic acids having about 8 to 14 carbon atoms, aliphatic dicarboxylic acids having about 4 to 12 carbon atoms, cycloaliphatic dicarboxylic acids having about 8 to 12 carbon atoms and esters or anhydrides thereof.
12. A copolyester according to claim 7, wherein the glycol component comprises 1, 4 cyclohexanedimethanol in an amount ranging from 20 to 40 mole % and ethylene glycol in an amount ranging from about 60 to about 80 mole %.
13. A copolyester according to claim 7, wherein the glycol component comprises 1, 4 cyclohexanedimethanol in an amount ranging from 25 to 35 mole % and ethylene glycol in an amount ranging from about 65 to about 75 mole %.
2 9
14. A copolyester according to claim 7, wherein the glycol component contains diethylene glycol in an amount up to 20 mole%.
15. A copolyester according to claim 7, wherein the IN. value ranges from about 0.41 to 0.49.
16. A copolyester according to claim 7, wherein the copolyester is formed in the presence of a branching agent.
17. A copolyester according to claim 7, wherein the copolyester is capable of being melt spun into a fiber at a temperature of less than about 270 °C.
18. A copolyester composition comprising the copolyester according to claim 7 and an additive selected from the group consisting of a pigment, a colorant, a stabilizer, an antioxidant, an extrusion aid, a slip agent, carbon black, a nucleating agent, a flame retardant, a filler, a conductive material, an adhesion promoter, a toughener, a viscosity modifier, a dye promoter and mixtures thereof.
19. A copolyester of claim 7, wherein the copolyester is in fibrous form.
20. The copolyester of claim 19, wherein the fibrous form of the copolyester has a denier ranging from 20 to microdenier sizes.
21. A fibrous structure comprising a fiber formed by melt blending a polyolefin or a functionalized polyolefin with the copolyester of claim 7.
22. A copolyester comprising the reaction product of: a glycol component with a dicarboxylic acid component, wherein the glycol component comprises 1 , 4 cyclohexanedimethanol in an amount ranging from 10 to 60 mole % and ethylene glycol in an amount ranging from about 40 to about 90 mole %, wherein at least about 90 mole % of the dicarboxylic acid component is
30 selected from the group consisting of acids, esters or anhydrides of terephthalic acid, napthalenedicarboxylic acid, 1,4-cyclohexane dicarboxylic acid and mixtures thereof, wherein the copolyester is formed in the presence of a catalyst system comprising about 10 to about 35 ppm Ti and wherein the copolyester has an IN. of between about 0.36 to 0.58.
23. A catalyst system for producing a copolyester comprising: a catalytic material comprising about 10 to about 35 ppm Ti and about 30 to about 70 ppm Mn, wherein the total amount of catalytic materials in the catalyst system is less than or equal to about 125 ppm; a catalytic inhibitor comprising about 40 to about 90 ppm P; and an effective amount of a colorant other than cobalt to produce a desired color; and wherein the amounts of the catalyst system components are based upon the weight of the copolyester product formed with the catalyst system.
24. The catalyst system of claim 23, wherein the total amount of catalytic materials in the catalyst system is less than 100 ppm.
25. The catalyst system of claim 23, wherein the catalyst is substantially free of Sb and Zn catalysts.
26. The copolyester of claim 7, wherein the copolyester is melt blended with another polymer.
27. A fibrous structure comprising a fiber formed from a melt blend of the copolyester of claim 7 and another polymer.
28. An additive comprising a melt blend of the copolyester of claim 7 and a first polymer, wherein the additive when blended with a second polymer is capable of forming a fiber and wherein the first and second polymers may be the same polymer.
3 1
PCT/US1998/017813 1997-08-28 1998-08-28 Improved copolymer binder fibers WO1999010573A1 (en)

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US6139954A (en) 2000-10-31

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