KR20170077890A - Environment-Friendly Hot-Melt Adhesive Resin Composition - Google Patents
Environment-Friendly Hot-Melt Adhesive Resin Composition Download PDFInfo
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- KR20170077890A KR20170077890A KR1020150187309A KR20150187309A KR20170077890A KR 20170077890 A KR20170077890 A KR 20170077890A KR 1020150187309 A KR1020150187309 A KR 1020150187309A KR 20150187309 A KR20150187309 A KR 20150187309A KR 20170077890 A KR20170077890 A KR 20170077890A
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- resin
- anhydride
- low density
- polyethylene
- polyol
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
- C09J123/06—Polyethene
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention relates to an adhesive resin composition comprising a polyetherester resin (TPEE), a low density linear polyethylene (LLDPE) resin or a low density polyethylene (LDPE) as a polyester elastomer, and a compatibilizing resin, Wherein the polyetherester resin is 10 to 30, low-density linear polyethylene (LLDPE) resin or low-density polyethylene (LDPE) 30 to 50, and compatibilizer resin 20 to 60.
Description
The present invention relates to a resin composition for eco-friendly hot melt adhesives, and more particularly to a resin composition using a polyetherester resin and a low-density polyethylene resin used for interlayer adhesion.
In general, synthetic fibers have a high melting point, and their use is often limited. Particularly, when it is used as an adhesive such as a wick in the use of a fiber or the like, or as an adhesive which is inserted between cloths on a tape to be pressure bonded, the fiber fabric itself may be thermally deteriorated by heating, It is required to easily adhere by a simple simple heating press without using such special equipment.
BACKGROUND ART [0002] Hot melt type binder fibers have been widely used in conventional low melting point polyester fibers for the purpose of bonding different types of fibers to each other in a mattress, an automobile interior or an interwoven fiber structure used for various nonwoven fabric padding applications.
Therefore, there is a high demand for a polyester resin having a low melting point, and it is used for a binder fiber or an adhesive. Copolyester (polyester) is generally used for such applications
For example, United States Patent No. 4,129,675 discloses a low melting polyester copolymerized with terephthalic acid (TPA) and isophthalic acid (IPA), but isophthalic acid (IPA) Low-melting polyesters using a large amount of isophthalic acid have a problem in that they are poor in competitiveness due to high production cost.
Japanese Unexamined Patent Application, First Publication No. Hei 10-298271 discloses that adipic acid is used instead of terephthalic acid in the polymerization process and 1,4-butanediol (BD) is used as a diol component instead of ethylene glycol ). However, the low melting point polyester produced by using adipic acid has a low melting point polyester having a melting point of 150 DEG C or less It is difficult to produce a low-melting-point polyester having a lower melting point.
In addition, conventionally used hot melt adhesives use a material in which a linear low density polyethylene resin and an ethylene vinyl acetate copolymer resin are blended. However, since the hot-melt adhesive film produced in this way generates a strong odor due to the volatile organic compounds generated from the ethylene vinyl acetate resin, a strong odor is generated even after the laminated molded article is completed, A big problem arises.
In order to solve the above problems, it is an object of the present invention to provide a resin composition having an excellent adhesive force and generating a volatile organic compound below a safety standard.
In order to achieve the above object, the present invention provides an adhesive resin composition comprising a polyetherester resin (TPEE), a low density linear polyethylene (LLDPE) resin or a low density polyethylene (LDPE) as a polyester elastomer and a compatibilizing resin, Wherein the weight ratio of the composition is 10 to 30 for a polyetherester resin, 30 to 50 for a low density linear polyethylene (LLDPE) resin or a low density polyethylene (LDPE), and 20 to 60 for a compatibilizer resin. do.
In the present invention, the polyetherester resin is obtained by esterifying a diol (diol) and a dicarbonic acid, which are a raw material of a hard segment, and polycondensation of a polyol as a soft segment raw material, (Diol) may be composed of a mixture of 1,4-butanediol (1,4-BD) or 1,4-butanediol (1,4-BD) and 2-methyl 1,3-propanediol (MPO) The dicarbonic acid may be one selected from the group consisting of dimethyl terephthalate (DMT) and dimethyl isophthalate (DMI), or a mixture of any of the above-described compositions with an anhydride resin, The present invention provides a resin composition for an environmentally friendly hot melt adhesive characterized in that the polyol can be composed of any one of poly (tetramethylene ether) glycol (PTMG), polyethylene glycol (PEG) and polypropylene glycol (PPG).
The present invention also relates to an anhydride resin, wherein the anhydride resin is selected from the group consisting of methyltetrahydrophthalic anhydride (MeTHPA), methylhexahydrophthalic anhydride (MeHHPA), terahydophthalic anhydride (THPA) Wherein the resin composition is at least one of ropthalic anhydride (HHPA) and ropthalic anhydride (HHPA).
The present invention also relates to a process for preparing the conjugated diene-conjugated diene-anhydride resin by reacting a conjugated diene having two double bonds with a maleic anhydride in a Diels-Alder reaction The present invention also provides a resin composition for eco-friendly hot-melt adhesives.
The present invention also provides a resin composition for eco-friendly hot-melt adhesive characterized in that the molecular weight of the polyol is 400 to 20,000, and the polyether ester resin is 10 to 80% by weight.
The present invention also provides a resin composition for an environmentally friendly hot melt adhesive characterized by adding a compatibilizing agent to increase the compatibility of the polyetherester resin and the low density linear polyethylene resin.
The present invention also provides a resin composition for eco-friendly hot-melt adhesive characterized in that the compatibilizer resin is copolymerized with ethylene, vinyl acetate, acrylic acid or methyl acrylate.
The present invention is composed of a polyetherester resin, a linear low density polyethylene resin, and a compatibilizer that allows the properties of the two materials to be well-miscible, thereby providing an excellent adhesive strength and a safe range of volatile organic compounds.
As used herein, the terms " about, " " substantially, " " etc. ", when used to refer to a manufacturing or material tolerance inherent in the stated sense, Accurate or absolute numbers are used to help prevent unauthorized exploitation by unauthorized intruders of the referenced disclosure.
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an adhesive resin composition comprising a polyester elastomer (TPEE) resin, a low density linear polyethylene (LDPE) resin and a compatibilizing resin,
The weight ratio of the composition is 10 to 30 for a polyetherester resin, 30 to 50 for a low density linear polyethylene (LLDPE) resin or a low density polyethylene (LDPE), and 20 to 60 for a compatibilizer.
The polyether ester resin is obtained by esterifying a diol (diol) and a dicarbonic acid (hard segment raw material) and condensing a polyol (polyol) as a soft segment raw material,
The diol may be composed of a mixture of 1,4-butanediol (1,4-BD) or 1,4-butanediol (1,4-BD) and 2-methyl 1,3-propanediol (MPO) ,
The dicarbonic acid may be any one selected from the group consisting of dimethyl terephthalate (DMT) and dimethyl isophthalate (DMI), or a mixture of any of the above-described compositions with an anhydride resin
The polyol is characterized in that it can be composed of any one of poly (tetramethylene ether) glycol (PTMG), polyethylene glycol (PEG) and polypropylene glycol (PPG).
The dimethylisophthalate (DMI) is dimethyl terephthalate (DMT) and its structural isomer, which is expensive but has the same effect.
The anhydride resin may also be selected from the group consisting of methyl tetrahydrophthalic anhydride (MeTHPA), methylhexahydrophthalic anhydride (MeHHPA), terahydrophthalic anhydride (THPA), and hexahydrophthalic anhydride And hydride (HHPA) may be added,
The polyol may be composed of any one of poly (tetramethylene ether) glycol (PTMG), polyethylene glycol (PEG), and polypropylene glycol (PPG).
Although an anhydride resin in the above dicarbonic acid can be directly used as a starting material for the esterification reaction, it is also possible to use a conjugated diene having two double bonds and a maleic anhydride The product through a Diels-Alder reaction of maleic anhydride may also be used.
To describe the esterification reaction of the polyester-based elastic adhesive resin composition, a low molecular weight diol component of 1,4-butanediol (1,4-BD) and a low molecular weight diol component of 1,4-butanediol (DMT).
The molar fraction of dicarbonic acid and diol is 1: 1.0 ~ 1.5, and the excess diol component is mostly recovered through the depressurization process during condensation polymerization. (Dicarbonic acid) and Diol (Diol) have a value of 30 to 90% by weight in the whole elastic adhesive resin composition.
Also, the mixture of 1,4-butanediol (1,4-BD) and 2-methyl 1,3-propanediol (MPO)
70 to 95 mol% of 1,4-butanediol (1,4-BD) and 5 to 30 mol% of 2-methyl 1,3-propanediol (MPO) can be used. When a certain amount of 2-methyl-1,3-propanediol (MPO) is added, the tendency of the hardness of the polyester-based elastic adhesive resin is lowered and the property to restore the original state is increased.
In addition, the dimethyl terephthalate (DMT) and the anhydride resin mixture may be composed of 80 to 95 mol% of dimethyl terephthalate (DMT) and 5 to 20 mol% of an anhydride resin .
In addition, the anhydride resin may have a molar ratio of methyl tertahydrophthalic anhydride (MeTHPA) and methyl hexahydrophthalic anhydride (MeHHPA) of 4 to 6 to 6 to 4.
Conventionally, aromatic or aliphatic tricarboxylic acids such as isophthalic acid, adipic acid and succinic acid have been used as a copolymerization raw material in order to control the melting point of the polyester-based elastic adhesive resin without using only dimethyl terephthalate (DMT)
The present invention relates to an anhydride resin such as methyltetrahydrophthalic anhydride (MeTHPA), methylhexahydrophthalic anhydride (MeHHPA), terahydophthalic anhydride (THPA), and hexahydrophthalic anhydride (HHPA) is added to terephthalate (DMT), it is possible to easily control various melting points required in the molding process of the final product while maintaining elastic properties and physical properties, which are important characteristics of the present invention .
Even when only a small amount of methyltetrahydrophthalic anhydride (MeTHPA) is substantially introduced, a melting point lowering phenomenon occurs, and a drop of about 4 ° C per mole can be obtained, and methyltetrahydrophthalic anhydride (MeTHPA), methyl When hexahydrophthalic anhydride (MeHHPA) is used in a molar ratio of 4 to 6 to 6 to 4, a lowering of the melting point occurs more greatly.
For example, when mixed with MeTHPA alone, a decrease of about 5 ° C per 1 mole of the mixture results in a greater effect of lowering the melting point.
The catalyst used in the esterification reaction is selected from the group consisting of zinc acetate, sodium acetate, magnesium acetate, tetranomalbutoxy titanate, tetraisopropyl titanate, titanium oxide / silicon oxide microcopolymer, and nano titanate And is used in a range of 50 to 1000 ppm with respect to 100 parts by weight of the polyester based elastic adhesive resin. If the amount of the catalyst is insufficient, the esterification reaction rate is slowed. If the amount of the catalyst is insufficient, the thermal stability of the polyester- It gets worse.
After the esterification reaction, the condensation polymerization proceeds.
The oligomer solution obtained by the esterification reaction and the soft segment polyol were introduced into a pressure resistance and heat resistance reactor capable of undergoing vacuum decompression together with a condensation polymerization catalyst, a heat stabilizer and a photo stabilizer, and then a pressure of 760 to 1000 Torr and a pressure of 200 After an excessive amount of diol (Doil) is distilled off at a temperature of ~ 270 ° C, condensation polymerization is completed under a high vacuum of 1 mmHg or less to obtain a polyester elastomeric bonding resin of the present invention.
Here, the polyol may be selected from poly (tetramethylene ether) glycol (PTMG), polyethylene glycol (PEG) or polypropylene glycol (PPG), the molecular weight of the polyol is 400 to 20,000, 10 to 80% by weight based on the total weight of the resin.
The polymerization catalyst used in the condensation polymerization step may be one selected from the group consisting of antimony trioxide, antimony acetate, tetranormalbutoxy titanate, tetraisopropyl titanate, titanium oxide / silica oxide microcopolymer, and nano titanate And may be used in the range of 50 to 2000 ppm based on 100 parts by weight of the polyester-based elastic bonding resin.
The low density polyethylene (LDPE) resin has a considerably large number of branching points of the polymer, resulting in a low density product having a density of about 0.916 to 0.935. The linear low density polyethylene (LLDPE) has a similar molecular structure to high density polyethylene but has a density similar to that of low density polyethylene.
Generally, when two or more polymers are mixed, it is difficult to mix them depending on the properties of the composition. Therefore, the compatibilizer resin is used to uniformly disperse the mixed polymers and improve the physical properties.
A specific compatibilizing resin is used according to the resin to be mixed. In the present invention, ethylene, vinyl acetate, acrylic acid or methyl (meth) acrylate is added to increase the compatibility of the polyetherester resin with the linear polyethylene (LLDPE) resin or the low density polyethylene Acrylate is used.
The features and other advantages of the present invention as described above will become more apparent from the following examples, which should not be construed as limiting or limiting the scope of protection of the present invention, .
Example And comparison
As shown in Table 1, the examples were prepared by mixing the polyetherester elastomer resin (PTEE) (A) as the compatibilizer, the ethylene acrylic acid copolymer resin (B), and the low density linear polyethylene (LLDPE) resin (C) Melted and kneaded in a Bender mixer,
In the comparative example, a low density linear polyethylene (LLDPE) resin (C) and an ethylene vinyl acetate (EVA) resin or vinyl acetate (VA) (D) were melted and kneaded in a Brabender mixer at a weight ratio shown in the table.
◎ Tensile strength, tensile elongation: ASTM D638
◎ Adhesive strength: To evaluate the adhesive strength of each polymer in the examples and comparative examples, the analysis is compared with reference to NIKE's adhesive film for footwear (Film) analysis method. The sample to be analyzed is made of a film having a thickness of 200 to 250 μm by using a hot press or the like. Adhesive film is inserted between the standard fabric (using polyester fabric) and thermocompressed for 30 seconds at a pressure of 3 kgf / cm 2 and a temperature of 150 ° C in a hot press. The thermally bonded sample was cut to a width of 1 inch and the tensile strength was measured according to the measurement method of ASTM D882 (Tensile Testing of Thin Plastic Sheet) to evaluate the adhesive strength.
division
(weight%)
Film Properties
(kgf / cm 2 )
(%)
(kgf / in.)
Composition A: Polyetherester elastomer resin (TPEE)
Composition B: 6.5% by weight of an ethylene acrylic acid copolymer (EAA) resin (product of Dow Corp., Primacor 3330), a melt index (Melt Index) of 5.8 g / 10 min, and acrylic acid (AA, Acrylic Acid) comonomer
Composition C: linear polyethylene resin having a low density linear polyethylene (LLDPE) resin (manufactured by LG Chemical), a melt index (MI) index of 1.6 g / 10 min and a density of 0.922 g /
Composition D: Ethylene vinyl acetate (EVA) resin (Lotte Chemical VA 900 product), vinyl acetate (VA, vinyl acetate) content 28 wt%
From the results of Table 1, it can be seen that the examples are superior to the comparative examples in tensile strength, adhesive strength and generation of volatile organic compounds.
Average
(JAMA)
(Ministry of Health and Welfare)
(tuv)
Benzene
Table 2 above shows the evaluation results of volatile organic compounds (VOCs) of the resin compositions for environmentally friendly hot melt adhesives of the present invention by comparing the VOC standards of each country.
As a result of the analysis, the average value of the embodiment of the present invention is 34.1 ppm in the toluene value, which is better than the comparative example average of 292.6 ppm. Although comparative average is satisfactory for Korean and Chinese standard values of 1000 V and 1100 ppm in automobile VOC standards, the comparative example average exceeds the standard and the average value of the embodiment meets the standards of 260 and 200 ppm of Japan and Germany standards.
The composition of the present invention, which satisfies foreign standards as automobiles exported worldwide, has significance.
It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the inventions. It will be clear to those who have knowledge of.
Claims (7)
Low density linear polyethylene (LLDPE) resin or low density polyethylene (LDPE),
And an adhesive resin composition comprising a compatibilizing resin,
Wherein the weight ratio of the composition is 10 to 30 for a polyetherester resin, 30 to 50 for a low density linear polyethylene (LLDPE) resin or a low density polyethylene (LDPE), and 20 to 60 for a compatibilizer resin.
The polyether ester resin is obtained by esterifying a diol (diol) and a dicarbonic acid (hard segment raw material) and condensing a polyol (polyol) as a soft segment raw material,
The diol may be 1,4-butanediol (1,4-BD)
1,4-butanediol (1,4-BD) and 2-methyl 1,3-propanediol (MPO)
The dicarbonic acid may be any one selected from the group consisting of dimethyl terephthalate (DMT) and dimethyl isophthalate (DMI), or a mixture of any of the above-described compositions with an anhydride resin
Wherein the polyol is composed of any one of poly (tetramethylene ether) glycol (PTMG), polyethylene glycol (PEG) and polypropylene glycol (PPG).
The anhydride resin may be selected from the group consisting of methyl tetrahydrophthalic anhydride (MeTHPA), methylhexahydrophthalic anhydride (MeHHPA), terahydrophthalic anhydride (THPA) and hexahydrophthalic anhydride (HHPA). ≪ RTI ID = 0.0 > 11. < / RTI >
The anhydride resin contains a product of a conjugated diene having two double bonds and a product of a Diels-Alder reaction of maleic anhydride. Wherein the resin composition is an epoxy resin.
The molecular weight of the polyol is 400 to 20,000,
Based resin is 10 to 80% by weight based on the polyether ester-based resin.
Wherein a compatibilizing agent is added to increase the compatibility of the polyetherester resin and the low density linear polyethylene resin.
Wherein the compatibilizer resin is copolymerized with any one of ethylene, vinyl acetate, acrylic acid or methyl acrylate.
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| KR1020150187309A KR101819723B1 (en) | 2015-12-28 | 2015-12-28 | Environment-Friendly Hot-Melt Adhesive Resin Composition |
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| KR1020150187309A KR101819723B1 (en) | 2015-12-28 | 2015-12-28 | Environment-Friendly Hot-Melt Adhesive Resin Composition |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018236094A1 (en) | 2017-06-20 | 2018-12-27 | 주식회사 엘지화학 | Polymer electrolyte membrane, electrochemical cell and flow cell each comprising same, composition for polymer electrolyte membrane, and method for preparing polymer electrolyte membrane |
| CN109609066A (en) * | 2018-12-13 | 2019-04-12 | 河北金天塑胶新材料有限公司 | A kind of hot melt adhesive and preparation method thereof for plastic-steel-wound drainage pipe |
| KR20190063902A (en) * | 2017-11-30 | 2019-06-10 | 롯데케미칼 주식회사 | Resin composition for preparing sheet and sheet prepared using the same |
| KR102649253B1 (en) * | 2023-05-02 | 2024-03-22 | 주식회사 조아라그룹 | Banner attached with hot melt adhesive as a substitute for sewing machine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19632474C2 (en) | 1996-08-12 | 2000-06-29 | Inventa Ag | Copolyetherester hot melt adhesives |
| JP2002173654A (en) * | 2000-12-05 | 2002-06-21 | Taoka Chem Co Ltd | Hot-melt adhesive composition |
| KR100964050B1 (en) * | 2005-05-19 | 2010-06-16 | 닛토덴코 가부시키가이샤 | Laminated tape for packaging material |
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2015
- 2015-12-28 KR KR1020150187309A patent/KR101819723B1/en active IP Right Grant
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018236094A1 (en) | 2017-06-20 | 2018-12-27 | 주식회사 엘지화학 | Polymer electrolyte membrane, electrochemical cell and flow cell each comprising same, composition for polymer electrolyte membrane, and method for preparing polymer electrolyte membrane |
| KR20190063902A (en) * | 2017-11-30 | 2019-06-10 | 롯데케미칼 주식회사 | Resin composition for preparing sheet and sheet prepared using the same |
| CN109609066A (en) * | 2018-12-13 | 2019-04-12 | 河北金天塑胶新材料有限公司 | A kind of hot melt adhesive and preparation method thereof for plastic-steel-wound drainage pipe |
| KR102649253B1 (en) * | 2023-05-02 | 2024-03-22 | 주식회사 조아라그룹 | Banner attached with hot melt adhesive as a substitute for sewing machine |
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| KR101819723B1 (en) | 2018-03-02 |
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