KR102043372B1 - Copolymerized Polyester for Low-melting Binder with Excellent Touch and Color and Polyester Binder Fiber Using Same - Google Patents
Copolymerized Polyester for Low-melting Binder with Excellent Touch and Color and Polyester Binder Fiber Using Same Download PDFInfo
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- KR102043372B1 KR102043372B1 KR1020140118539A KR20140118539A KR102043372B1 KR 102043372 B1 KR102043372 B1 KR 102043372B1 KR 1020140118539 A KR1020140118539 A KR 1020140118539A KR 20140118539 A KR20140118539 A KR 20140118539A KR 102043372 B1 KR102043372 B1 KR 102043372B1
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- copolyester
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- 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
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5357—Esters of phosphonic acids cyclic
-
- 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
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- 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
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Copolymerized polyester resin for low melting point binder according to the present invention copolymerizes the acid component consisting of terephthalic acid or its ester-forming derivative and the diol component consisting of 2-methyl-1,3-propanediol, diethylene glycol and ethylene glycol It is characterized by being manufactured by. The 2-methyl-1,3-propanediol is preferably added in the range of 10 to 50 mol% based on the mole of the copolyester. In addition, in order to strengthen the intermolecular bonds, a multifunctional component in the range of 10 to 10,000 ppm may be further added to the copolyester.
Description
The present invention relates to copolyester for low melting point binder. More specifically, the present invention relates to a co-polyester for low melting point binder, which is excellent in touch and color and has a low content of a cyclic compound in the resin. The present invention also includes a composite fiber for a polyester binder made from the copolymerized polyester for the binder of the present invention.
Heat-sealed binder fibers may be used to bond the filaments or short fibers that make up the web or sheet of nonwoven fabric. The binder fiber should have a glass transition temperature close to that of general polyethylene terephthalate fiber with thermal bonding processing temperature of 140-150 ° C. To do this, it is necessary to remove the crystal structure in the polymer and make the polymer structure amorphous.
Polyester is used in textiles and engineering plastics because of its excellent mechanical properties, heat resistance, and chemical resistance, but it has a high melting point because of its molecular structure, which makes it difficult to use as a binder. In order to use polyester as a binder fiber, high temperature and pressure are required in a manufacturing process, and therefore, there are many process difficulties. Therefore, many studies have been continued for the development of the binder polyester.
In one of the methods, in synthesizing the polyester resin, there is a method of copolymerizing isophthalic acid and terephthalic acid. In this method, isophthalic acid is added in an amount of 20 to 45 mol% based on the moles of esters. The polyester resin thus synthesized has a molecular structure in an amorphous form and thus shows a final melting point in the range of 145 to 180 ° C., which can be used as a polyester fiber for a binder.
However, polyester resins for binders using isophthalic acid form a cyclic compound having a polymerization degree of 2 to 3 when synthesized. This cyclic compound has a disadvantage that the melting point does not melt at the polyester spinning temperature of about 325 ° C., which acts as a foreign matter during spinning, and thus shortens the pack replacement cycle. In addition, since the cost of isophthalic acid is also high, the cost rises. It becomes a factor.
U.S. Patent No. 4,129,675 discloses low melting copolymers copolymerized using terephthalic acid and isophthalic acid. However, the copolyester of this patent is capable of heat fusion at a high temperature of 190 ° C. or higher, which consumes a lot of energy in the process.
U.S. Patent No. 4,166,896 discloses a method for preparing unsaturated polyesters by copolymerizing unsaturated dicarboxylic acids with low molecular weight polymerized depolymerized polyesters, but this method is not only economically low but also has a high melting point and a high melting point for use as a binder. There is a disadvantage that is crystalline.
Korean Laid-Open Patent No. 2001-11548 is a polyester-based polycondensation product of dicarboxylic acid components of terephthalic acid and phthalic anhydride and diol components of ethylene glycol and diethylene glycol, and has excellent adhesion with polyester, and does not cause yellowing after adhesion. Although a binder for fibers is provided, the binder has a disadvantage in that the reaction mechanism is complicated by using phthalic anhydride directly, and thus the polycondensation temperature must be lowered to prevent the problem of poor color of the copolyester. In addition, such low-temperature condensation polymerization reaction has a problem of lowering the productivity.
The copolyester synthesized using the phthalic anhydride of Korean Patent Publication No. 2001-11548 has a color of the obtained polymer under the same conditions as in the polyethylene terephthalate polycondensation step of heating to 270 ° C. to 290 ° C. under a reduced pressure of 1 mmHg or less. There is a disadvantage to be poor. This is because the phthalic anhydride added in the composition of the reaction system at high temperature and high vacuum polymerization conditions participates in the reaction in which the ring-opening reaction, the direct esterification reaction, and the transesterification reaction are mixed in the reaction process, so that pyrolysis and side reactions occur to produce a colored material. Because.
In the present invention, in order to solve the problems of the prior art as described above, in the copolyester polyester resin for low-melting point binder, the content of the cyclic compound acting as a foreign matter is small, the present invention having excellent adhesion even at low temperature below 180 ℃ Copolymer polyester resin for low melting point binder was developed, and polyester resin composite fiber excellent in heat fusion, touch and color at low temperature was developed using this resin.
An object of the present invention, in the low-melting-point binder copolyester resin, the content of the cyclic compound acting as a foreign matter is small, excellent thermal adhesion at a low process temperature of 140 ~ 160 ℃, excellent touch and color after adhesion It is to provide a high quality new binder-based resin.
Another object of the present invention is to form a cyclic compound having a degree of polymerization of 2 to 3 in a polyester resin for a binder using isophthalic acid as a copolymerization component, which acts as a foreign matter during spinning, and thus has a short pack exchange cycle. It is to provide a new polyester-based resin for the binder that can increase the pack exchange cycle because no cyclic compound is formed.
Another object of the present invention is a low temperature to solve the problem of poor color and poor color problem due to the accumulation of coloring matter due to thermal decomposition and side reactions when polymerizing polyester using phthalic anhydride as a copolymerization component when polymerizing the polyester While there is a problem of deterioration of productivity through the polycondensation reaction, the phenol-phosphorus complex thermal stabilizer (hereinafter referred to as 'Ph-P complex thermal stabilizer') is used to protect the resin at high temperatures and to prevent discoloration, thereby causing yellowing. An object of the present invention is to provide a new polyester-based resin for binders having low color-b values.
Still another object of the present invention is to provide a high quality polyester-based binder composite fiber having excellent heat fusion at low temperature and excellent touch and color using the polyester-based binder resin of the present invention.
The above and other objects of the present invention can be achieved by the present invention described in detail below.
Copolymerized polyester resin for a low melting point binder according to the present invention copolymerizes the acid component consisting of terephthalic acid or its ester-forming derivative and the diol component consisting of 2-methyl-1,3-propanediol, diethylene glycol and ethylene glycol It is characterized by being manufactured by.
In order to achieve the above object of the present invention, 2-methyl-1,3-propanediol is used as a copolymer material capable of implementing an amorphous molecular structure, which is a methyl group on the second carbon of a conventional 1,3-propanediol. Is further combined. In the case of 2-methyl-1,3-propanediol, the methyl group of the second carbon facilitates the rotation of the polymer backbone and acts as if it is the terminal portion of the polymer, thereby extending the free space between the backbones. This has the same effect as the meta-structure of isophthalic acid forming a bending structure in the polymer backbone, preventing it from becoming a crystalline polymer and having an amorphous molecular structure. In addition, there is an advantage that does not participate in the formation of the cyclic compound formed by isophthalic acid, so that the pack exchange cycle can be increased, which is much more productive. The structure of 2-methyl-1,3-propanediol is as follows.
The 2-methyl-1,3-propanediol is preferably added in the range of 10 to 50 mol% based on the mole of the copolyester.
In the polycondensation reaction, it is preferable to further include a Ph-P composite thermal stabilizer having the following formula of 1 to 1,000 ppm of phosphorus (P) content.
In addition, in order to strengthen the intermolecular bonds, a multifunctional component in the range of 10 to 10,000 ppm may be further added to the copolyester.
Polyester binder composite fiber excellent in shape stability of the present invention is a core component of the general polyester; And a composite polyester resin for binder prepared by copolymerizing an acid component composed of terephthalic acid or an ester-forming derivative thereof and a diol component composed of 2-methyl-1,3-propanediol and ethylene glycol as a sheath component. Manufacture.
Hereinafter, specific contents of the present invention will be described in detail below.
As described above, according to the present invention, it is possible to provide a binder fiber excellent in low temperature fusion and excellent in touch and color after contact. In addition, while the thermal properties are very similar to isophthalic acid, it is not involved in the production of a cyclic compound having a degree of polymerization of 2 to 3 formed by isophthalic acid, thereby increasing the pack exchange cycle during spinning. On the other hand, in order to increase the thermal stability of the resin may be added to the phosphorus (P) content of 1 ~ 1,000ppm Ph-P composite thermal stabilizer. As a result, the resin can be protected through radical removal under high temperature condensation polymerization, and the discoloration of the resin can be prevented by decomposing the peroxide. On the other hand, in order to strengthen the intermolecular bonds, 10 to 10,000 ppm, more preferably 50 to 3,000 ppm, of a multifunctional component having a crosslinking action can be added. By doing so, the condensation polymerization reaction time can be shortened, and the processability can be improved, such as reducing the trimming rate when spinning and stretching into fibrous form.
The present invention relates to a co-polyester for low-melting point binder, and to a co-polyester for low-melting point binder having excellent feel and color and a low content of cyclic compound in the resin. The present invention also includes a composite fiber for a polyester binder made from the copolymerized polyester for a binder of the present invention.
Copolymerized polyester resin for low melting point binder according to the present invention copolymerizes the acid component consisting of terephthalic acid or its ester-forming derivative and the diol component consisting of 2-methyl-1,3-propanediol, diethylene glycol and ethylene glycol It is characterized by being manufactured by.
According to the present invention, when a resin is prepared using 2-methyl-1,3-propanediol, it is not involved in the production of a cyclic compound as a side reaction product. It can increase, and productivity can be improved.
In addition, the methyl group of the second carbon of 2-methyl-1,3-propanediol facilitates the rotation of the polymer backbone and acts as if it is the terminal portion of the polymer, thus expanding the free space between the backbones. Therefore, not only the thermal bonding between fibers is possible at low process temperatures, but also the shape stability is excellent even at a high temperature of 100 to 130 ° C after fabrication of the nonwoven fabric. However, the effect of lowering the melting temperature is great, but the glass transition temperature does not drop significantly, resulting in a high glass transition temperature of more than 65 ℃ even when the amorphous polymer when used alone. A high glass transition temperature is good for durability but has a stiff touch, which is not suitable for nonwoven fabrics or padding applications that require a soft touch. On the other hand, when copolymerizing with diethylene glycol, the glass transition temperature drop phenomenon is large, it is possible to prepare a resin having a desired glass transition temperature by adjusting the input amount of diethylene glycol. Therefore, when the binder fiber of the present invention is used, it is possible to produce a nonwoven fabric having excellent heat adhesion at low temperature and a soft touch after adhesion. In addition, the thermal properties are very similar to isophthalic acid, which can replace production of relatively expensive isophthalic acid, thereby lowering the production cost.
The copolyester-based binder fiber according to the present invention is a binder fiber in which a general polyester as a core component and a copolyester as a cis component are combined, and the copolyester is an acid component composed of terephthalic acid and ester-forming derivatives thereof. -Copolymer polyester obtained by copolymerizing a diol component consisting of -methyl-1,3-propanediol, diethylene glycol, and ethylene glycol, based on the mole of ester in the copolymer polyester. If the propanediol is 10 to 50 mol% and the content is less than 10 mol%, the melting point is not sufficiently lowered to obtain the desired polyester resin, and at 50 mol% or more, the crystallinity is sufficiently lowered, and further effects. Can not be obtained, but when excessively added, it acts as a main component in the diol component to increase crystallinity. The key is to get the opposite effect. The content of the diethylene glycol is preferably 1 to 25 mol% based on the ester mole, and if the content is less than 1 mol%, it is not possible to obtain a polyester resin that lowers the melting point and suppresses the formation of the cyclic compound, and 25 mol If it is higher than%, the glass transition temperature is lowered to 55 ° C. or lower, which may cause a change in fiber over time during spinning.
In the present invention, in order to increase thermal stability, a Ph-P composite-based thermal stabilizer of the following chemical formula may be used, and the input amount may be 1 to 1,000 ppm with respect to the copolyester.
If the amount of the thermal stabilizer is 1 ppm, it is not enough to improve the desired thermal stability, and if more than 1,000 ppm is added, there is a problem that the reactivity is lowered.
On the other hand, the polyfunctional component used in the preparation of the copolyester of the present invention is selected from the group consisting of polycarboxylic acid, polyol and polyoxycarboxylic acid, in particular, trimellitic acid, trimesic acid, 3,3 ', 4, It is preferably selected from the group consisting of 4'-benzophenonetetracarboxylic acid, 1,2,3,4-butanetetracarboxylic acid and derivatives thereof such as acid esters and acid anhydrides, glycerin, pentaerythritol and sorbitol. At this time, the multifunctional component lowers excessive temperature rise of the resin due to exothermic reaction during condensation polymerization of the binder according to the present invention, shortens the reaction time to improve color defects, and workability when spinning and stretching into fibrous form. It is preferable to include 10 to 10,000 ppm for each copolyester component to improve, but more preferably 50 to 3,000 ppm is added since it is advantageous that the melt viscosity is not too high for the adhesive use. At this time, if the addition amount of the multifunctional component is less than 10ppm, the role of the desired crosslinking agent can not be achieved, if the addition amount exceeds 10,000ppm causes problems during polymerization, spinning and stretching due to the rapid crosslinking phenomenon.
Hereinafter, the present invention will be described in more detail with reference to the following examples, but these examples are merely illustrative of the present invention and are not intended to limit or limit the protection scope of the present invention.
Examples 1-3
Terephthalic acid and ethylene glycol were added to the ester reactor, followed by reaction at a temperature of 258 ° C. in a conventional manner to prepare an oligomer having a reaction rate of 96%. To the oligomer obtained therein, 2-methyl-1,3-propanediol, diethylene glycol and ethylene glycol were added to the oligomer based on the molar amount of polyethylene terephthalic acid together with a Ph-P composite thermal stabilizer and a conventional transesterification catalyst. To a transesterification reaction at 250 ℃. Trimethylolpropane (TMP), which is a type of polyfunctional reactor, and a conventional condensation polymerization catalyst were added to the esterified oligomer thus obtained, and then the mixture was heated up to 280 ° C while gradually depressurizing to a final pressure of 0.1 mmHg. Was carried out. The performance of the polyester resin thus prepared was evaluated as described above, and the results are shown in Table 1 below.
Comparative Examples 1 to 3
In order to verify the effects of the thermal stabilizer and the multifunctional reactor, the diol component input ratio was added in the same manner as in Example 1. The polymerization was carried out in the same manner as in Examples 1 to 3, except that the same was added or not added. The performance of the polyester resin thus prepared was evaluated as described above, and the results are shown in Table 1 below.
Comparative Examples 4-6
Isophthalic acid other than 2-methyl-1,3-propanediol was added by content, and the same method as in Examples 1 to 3 except that the thermal stabilizer type and the multifunctional reactor were not added or added as shown in Table 1. Polymerize with. The performance of the polyester resin thus prepared was evaluated as described above, and the results are shown in Table 1 below.
MPD: 2-methyl-1,3-propanediol, DEG: diethylene glycol, EG: ethylene glycol
IPA: isophthalic acid, TMP: trimethylolpropane
The measurement of the evaluation item shown to the said Example and the comparative example was performed as follows.
1. Measurement of Cyclic Compounds and TMP Content: The additive mole% of the copolyester was dissolved in trifluoroacetic acid using Bruker's DRX-300 proton nuclear magnetic resonance apparatus (1H NMR). Measured.
2. Melting Point / Glass Transition Temperature and Softening Behavior: Measured using a differential thermal scanning calorimeter (Perkin Elmer, DSC-7), a dynamic thermal measuring instrument when no heat absorption peak is present, ie, no melting point. Softening behavior was measured using (Perkin Elmer, DMA-7; TMA mode).
3. Measurement of Intrinsic Viscosity (IV): The copolyester was dissolved in phenol / tetrachloroethane (50/50 by weight) to make a 0.5% by weight solution, and then measured at 35 ° C with a Uberod viscometer.
4. Room Temperature Adhesion: The prepared heat-sealed nonwoven fabric was fixed at a density of 2 g / 100 cm 2, and the ambient temperature was measured at 25 ° C. by the method of ASTM D1424.
5. Touch: Relative evaluation by touch. (◎ (excellent), ○ (good), △ (normal), X (bad))
As shown in Table 1 above, when Examples 1 to 3 using 2-methyl-1,3-propanediol and Comparative Examples 1 to 4 using isophthalic acid are compared, they have at least equivalent intrinsic viscosities. When methyl-1,3-propanediol is added, the b value indicating yellowing is lower, so the color is better and the touch is softer. As can be seen from the results of room temperature adhesion, even when polymerized with 2-methyl-1,3-propanediol, the adhesion is the same level, and when the multifunctional reactor is added when comparing the Example 1 and Comparative Example 1 This increased adhesion and better reaction time. Comparing Example 1 with Comparative Example 2, when the Ph-P composite thermal stabilizer is added to the conventional P-based thermal stabilizer, the b-value is lower and the color is better. In addition, isophthalic acid reacts with ethylene glycol to produce a cyclic dimer, which acts as a foreign material, shortens the pack exchange cycle, deteriorates radioactivity, and has a disadvantage in that isophthalic acid is generally expensive. 2-Methyl-1,3-propanediol and diethylene glycol are not involved in the production of cyclic dimers, which contributes to lower foreign matter content in polyester, longer pack exchange cycles, and lower production costs due to lower raw material prices. There is this.
Simple modifications and variations of the present invention can be easily made by those skilled in the art, and all such modifications or changes can be seen to be included in the scope of the present invention.
Claims (10)
Acid components composed of terephthalic acid or ester-forming derivatives thereof as the sheath component;
Dimethyl component consisting of 2-methyl-1,3-propanediol, diethylene glycol and ethylene glycol;
In the polyester-based binder composite fiber excellent in touch and color produced by the composite spinning of a copolymerized polyester binder prepared by copolymerizing
The 2-methyl-1,3-propanediol is 15 to 25 mol% or less based on the mole of ester in the copolyester and the diethylene glycol is characterized in that the input in the range of 15 to 25 mol% or less Polyester binder composite fiber with excellent touch and color.
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| KR1020140118539A KR102043372B1 (en) | 2014-09-05 | 2014-09-05 | Copolymerized Polyester for Low-melting Binder with Excellent Touch and Color and Polyester Binder Fiber Using Same |
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| KR1020140118539A KR102043372B1 (en) | 2014-09-05 | 2014-09-05 | Copolymerized Polyester for Low-melting Binder with Excellent Touch and Color and Polyester Binder Fiber Using Same |
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| KR1020170121262A Division KR20170110064A (en) | 2017-09-20 | 2017-09-20 | Polyester Fiber with Excellent Touch and Color |
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| KR102043372B1 true KR102043372B1 (en) | 2019-11-11 |
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| KR102043373B1 (en) * | 2017-11-28 | 2019-12-02 | 주식회사 휴비스 | Vehicle interior panel comprising low melting polyester fiber |
| KR102648800B1 (en) * | 2021-08-09 | 2024-03-15 | 도레이첨단소재 주식회사 | Polyester resin, preparing method thereof, thermally adhesive polyester fiber made thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007254702A (en) * | 2006-02-24 | 2007-10-04 | Toyobo Co Ltd | Crystalline polyester resin, hot melt adhesive using the same, and extrudable coating agent |
| JP2009084348A (en) | 2007-09-28 | 2009-04-23 | Toyobo Co Ltd | Adhesive composition, laminate, and flexible flat cable using solvent-soluble crystalline polyester resin |
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| JP3778808B2 (en) * | 2001-04-04 | 2006-05-24 | 帝人ファイバー株式会社 | Polyester-based heat-adhesive conjugate fiber and method for producing the same |
| KR20040100213A (en) * | 2003-05-22 | 2004-12-02 | 홍명선 | Modified polyester binder fiber and its manufacturing process |
| US7008698B2 (en) * | 2003-06-17 | 2006-03-07 | Mitsubishi Polyester Film, Llc | Propane diol-based polyester resin and shrink film |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007254702A (en) * | 2006-02-24 | 2007-10-04 | Toyobo Co Ltd | Crystalline polyester resin, hot melt adhesive using the same, and extrudable coating agent |
| JP2009084348A (en) | 2007-09-28 | 2009-04-23 | Toyobo Co Ltd | Adhesive composition, laminate, and flexible flat cable using solvent-soluble crystalline polyester resin |
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