JPH02247226A - Polyester amide resin and hot-melt adhesive composed thereof - Google Patents

Abstract

PURPOSE:To obtain a polyester amide resin giving a hot-melt adhesive having excellent color, moisture-resistance, heat-resistance and washing resistance and suitable for the bonding of cloth to cloth by carrying out polycondensation of a specific esterification reaction product and a specific depolymerized polyamide resin. CONSTITUTION:The objective polyester amide resin is produced by carrying out polycondensation reaction of (A) an esterification reaction product (preferably having a molecular weight of 300-2,000) obtained by the esterification reaction of a polybasic acid component (preferably terephthalic acid, etc.) and a polyhydric alcohol component (preferably 1,4-butylene glycol) and (B) a depolymerized polyamide resin having a number-average molecular weight of 250-1,500 (preferably 350-900) and obtained by the depolymerization of a polyamide resin (e.g. nylon 6) in the presence of a polybasic acid. The polycondensation reaction is carried out preferably at a weight ratio (A:B) of 75:25-40:60 in an inert gas atmosphere in the presence of a catalyst such as tetrabutyl titanate at 200-260 deg.C for 1-5hr.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a polyesteramide resin containing a depolymerized polyamide resin component in its molecule, and a hot melt adhesive using the same.

In the production of traditional technical clothing, the sewing process occupies a considerable part of the total process. Therefore, adhesive sewing has been adopted as a method for streamlining the sewing process. Adhesive sewing includes adhesive sewing of interlining, adhesive sewing of covering cloth, adhesive sewing of lining, adhesive sewing of ordinary clothing, etc., but adhesive sewing of interlining is particularly important.

The base fabric for adhesive interlining is woven fabric, non-woven fabric, or knitted fabric.

A powder-blown hot melt adhesive is applied to one or both sides of the adhesive. Conventionally, temporary adhesive types of hot melt adhesives for this purpose include low density polyethylene, ethylene-vinyl acetate copolymer, and polyvinyl chloride. However, permanent adhesive types use polyamide resin, polyester resin, polyurethane resin, etc. (“Adhesion Handbook”, published by Nikkan Kogyo Shimbun, July 1983)
(Refer to p. 604, 2nd edition published on May 5th, 4th printing, page 604) Among these, when considering performance (adhesiveness, dry cleaning resistance, etc.) and cost, polyamide resin-based hot We are interested in melt adhesives and polyester resin-based hot melt adhesives that have good adhesion to synthetic fibers.

Amide Modified Polyester Resin Hot melt adhesives using certain polyester amide resins are expected to have good adhesion to both natural fibers and synthetic fibers. From this point of view, the applicant has already developed the following two types of polyesteramide resin hot melt adhesives.
A number of applications have been filed.

That is, JP-A-51-22732 discloses an acid component consisting of terephthalic acid and adipic acid, a glycol component consisting of 1,4-butanediol and ethylene glycol, and a third acid component consisting of ε-caprolactam or ε-aminocaproic acid. There is a disclosure of a polyesteramide resin for adhesives containing three components in a specific ratio, and in Example 1, the third component was charged into a reactor together with an acid component and a glycol component from the beginning and reacted. Example 2 shows an example in which an acid component and a glycol component are first subjected to an esterification reaction, and then a third component is charged and reacted, and then polycondensation is performed. ing. It is also described that the polyesteramide resin thus obtained is useful as a hot melt adhesive for bonding fabrics together.

Furthermore, in JP-A-51-125194, after the esterification reaction between an acid component consisting of terephthalic acid and adipic acid and a glycol component consisting of 1,4-butanediol and ethylene glycol, ε-caprolactam or A method is disclosed for producing a polyesteramide resin by adding and reacting a third component consisting of ε-7 minocaproic acid and then performing polycondensation. It is also described that the obtained polyesteramide resin is suitable as a hot melt adhesive mainly for bonding cloth to cloth.

Problems to be Solved by the Invention However, in general, polyesteramide resin is a highly crystalline resin that was originally used as a molding material for fibers and films, and its suitability as a hot melt adhesive for bonding cloth to cloth is limited. It does not necessarily have.

In this regard, the above-mentioned inventions of JP-A-51-22732 and JP-A-51-125194 have the significance of making it possible to use polyesteramide resin as a hot melt resin for bonding cloth to cloth. However, the color of the resin is somewhat dark, hydrolysis or thermal decomposition may occur under high humidity or high temperature conditions, and the resin may change in quality, and the adhesive strength may deteriorate when washed with water or dry cleaned. There were problems such as a considerable decrease in

In view of this situation, the present invention has been developed to improve resin hue, moisture resistance,
The purpose of this invention is to provide a polyesteramide resin hot melt adhesive that has significantly improved heat resistance and washing resistance.

Means for Solving the Problems The polyesteramide resin of the present invention is obtained by esterifying an esterification reaction product (A) in which a polybasic acid component and a polyhydric alcohol component are esterified, and a polyamide resin in the presence of a polybasic acid. It consists of a polycondensation reaction product with a depolymerized polyamide resin (B) having a number average molecular weight of 250 to 1,500 obtained by polymerization.

Further, the hot melt adhesive of the present invention is made of the above-mentioned polyesteramide resin.

The present invention will be explained in detail below.

<Esterification reaction product (A)> The esterification reaction product (A) is obtained by esterifying a polybasic acid component and a polyhydric alcohol component.

As the polybasic acid component, polybasic acids having about 4 to 20 carbon atoms, particularly saturated dicarboxylic acids, are used.

Here, the saturated dicarboxylic acid components include terephthalic acid,
Isophthalic acid, phthalic acid, 2,5-norbornanedicarboxylic acid, 1,4-naphthalic acid.

1.5-Naphthalic acid, siphenic acid, 4,4°-oxybenzoic acid, aromatic dicarboxylic acids such as 2,5-naphthalene dicarboxylic acid, tetrahydrophthalic anhydride, 2.5
- norbornane dicarboxylic acid, het acid, oxalic acid, malonic acid, dimethylmalonic acid, succinic acid, geltaric acid,
Non-aromatic dicarboxylic acids such as 2.2-dimethylgeltaric acid, adipic acid, dodecanedicarboxylic acid, pimelic acid, superric acid, azelaic acid, sebacic acid, and 1,3-cyclohexanedicarboxylic acid are mentioned. Acid anhydrides, lower alkyl esters, and halogen-substituted products of the above-mentioned saturated dicarboxylic acids can also be used. Among the above, it is preferable to use at least a portion of terephthalic acid and/or isophthalic acid from the viewpoint of physical property balance.

Examples of polyhydric alcohol components include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, 1.2- or 1.3-propylene glycol, dipropylene glycol, polypropylene glycol, neopentyl glycol, 1, 3-11.
4- or 2.3-butylene gellicol 21.5-bentanediol, 1,6-hexanediol, 2-ethyl-1,3-hexanediol, 2,2.4-trimethyl-1,3-bentanediol, l,4-cyclohexane dimetatool, polytetramethylene glycol, bisphenol A, hydrogenated bisphenol A, and the like.

A small amount of trihydric or higher alcohol such as trimethylolethane, trimethylolpropane, glycerin, 1.3.6-hexanediol, pentaerythritol, bisphenol dioxypropyl ether, etc. can also be used in combination.

Among the above, from the viewpoint of physical property balance, it is preferable to use at least a portion of 1,4-butylene gellicol (eg, 30 mol % or more of the polyhydric alcohol component).

The esterification reaction product (A) is prepared by combining a polybasic acid component and a polyhydric alcohol component in an inert gas atmosphere at a temperature of 1.
It is produced by esterification at about 50 to 280°C. In this case, in addition to a method in which all components are charged at once and reacted, a method in which, for example, a portion of the glycol component is charged in portions and reacted is also adopted.

This esterification reaction can be carried out without a catalyst, but
Suitable esterification reaction catalyst (for example, one or two organic titanates such as tetrabutyl titanate and tetraisopropyl titanate, zinc acetate, antimony trioxide, zinc chloride, stannous lauryl, dibutyltin oxide, etc.)
The reaction proceeds more smoothly if the esterification reaction is carried out in the presence of

It is desirable that the esterification be carried out until the number average molecular weight of the resulting esterification reaction product (A) is 300 to 2000, because the desired effect is maximized within this range.

<Depolymerized polyamide resin (B)> Depolymerized polyamide resin (B) is a polyamide resin with a number average molecular weight of 25 obtained by depolymerizing a polyamide resin in the presence of a polybasic acid.
0-1500 depolymerized product.

Examples of polyamide resins before depolymerization include nylon 6, nylon 66, nylon 11. Nylon 12, nylon 61
In addition to 0, nylon 612, etc., various copolymerized nylons can be mentioned.

The depolymerization of the polyamide resin is achieved by reacting the polyamide resin and the polycarboxylic acid at high temperature, preferably under an inert gas atmosphere, normal pressure or pressurization.

The amount of polybasic acid used for depolymerization of polyamide resin is:
Approximately 1 to 4 moles per 1000 g of polyamide resin is appropriate; if the amount is too small, the degree of depolymerization will be insufficient, while if the amount is too large, the depolymerization reaction will proceed excessively and the desired effect will not be achieved. is no longer played.

The appropriate reaction temperature for depolymerization is about 180 to 280°C; if the reaction temperature is too low, the depolymerization reaction will not proceed smoothly, while if the reaction temperature is too high, the resin will deteriorate due to thermal decomposition of the polyamide resin. There is a risk of deterioration of hue and reduction of moisture resistance.

A reaction time of about 20 minutes to 5 hours is usually sufficient.

As the polybasic acid used for depolymerization, the saturated dicarboxylic acid mentioned above in the description of the esterification reaction product (A) is used.

After depolymerization, it can be esterified with a polyhydric alcohol, and this esterified product can also be used as the depolymerized polyamide tree I'll (B).

The number average molecular weight of the depolymerized polyamide resin (B) obtained by depolymerization is adjusted to be 250 to 1,500. If the number average molecular weight is less than 250, crystallization may occur, and the effect of improving moisture resistance, heat resistance, or washing resistance may not be sufficiently obtained. However, a resin with a high melting point is obtained, making it impossible to use it for interlining. A particularly preferred range is 350-900. In addition, the ratio Mw of the double average molecular weight Mw to the number average molecular weight Mn of such depolymerized polyamide resin (B)
/Mn is approximately 1.3 to 3.0.

They have the same molecular weight.

Therefore, in producing the depolymerized polyamide resin CB), care should be taken to set the depolymerization reaction conditions so that the number average molecular weight of the target product falls within the above range.

<Polyesteramide resin> The polyesteramide resin of the present invention comprises the above-mentioned esterification reaction product (A) and the above-mentioned depolymerized polyamide tree If1 (B).
It is obtained by polycondensation reaction.

Esterification reaction product (A) and depolymerized polyamide resin (B)
The reaction ratio with the depolymerized polyamide resin (B) is preferably 90:10 to 30% by weight, especially 75:25 to 40:60.When the ratio of the depolymerized polyamide resin (B) is out of this range, properties, heat resistance.

The effect of improving wash resistance may be insufficient, and depending on whether the object to be bonded is natural fiber or synthetic fiber, the adhesive force may be insufficient.

Esterification reaction product (A) and depolymerized polyamide resin (B)
The polycondensation reaction with 0.05% is preferably obtained by reacting both in the presence of a catalyst under an inert gas atmosphere, and the desired reaction temperature is 200 to 260°C. If the reaction temperature is too low, polycondensation may occur. A reaction time of about 60 minutes to 5 hours is sufficient, since the reaction becomes insufficient, and if the reaction time is too high, the resulting reaction product becomes colored and its commercial value decreases.

As the catalyst used in the polycondensation reaction, the esterification reaction catalyst described in the description of the esterification reaction product (A) is often used, and germanium oxide and other catalysts are also used. Esterification reaction product (A
) If the amount of the esterification catalyst is increased during the production of esterification or the polycondensation catalyst is added at the time of the esterification reaction, it may not be necessary to add the polycondensation catalyst again.

<Hot Melt Adhesive> The polyesteramide resin thus obtained can be suitably freeze-pulverized or chemically pulverized to a predetermined particle size and used for the purpose of a hot-melt adhesive. Optionally, it can also be formed into a film and used for hot melt adhesive purposes.

It is also possible to add fillers, colorants, other hot-melt resins, etc. during the manufacturing process of the polyesteramide resin or at any stage after manufacturing.

(Applications) The polyesteramide resin of the present invention can be used as a hot melt adhesive, particularly for adhesive sewing of interlining, adhesive sewing of covered cloth,
It can be suitably used in applications such as adhesive sewing of linings, adhesive sewing of regular clothing, and adhesive sewing of cloth to cloth in the production of clothing. , # is important to glue and sew the interlining.

Other applications include melt sizing, nonwoven fabric production, and carpet backing. Depending on the case,
It can also be used to bond plastics, rubber, metals, glass, leather, paper, wood, etc.

Functions and Effects of the Invention The polyesteramide resin of the present invention can be said to be a block copolymer in which polyester units as soft segments and polyamide units as hard segments are copolymerized in blocks. Moreover, since the polyamide unit uses a depolymerized polyamide resin, it has the characteristic that the molecular weight is uniform (the width of the molecular weight distribution is narrow).

On the other hand, as mentioned in the section of the prior art,
As can be seen from the fact that the polyesteramide resin described in Example 1 of Publication No. 732 was prepared by charging the acid component, glycol component, and third component all at once and reacting them,
It is a random or nearly random copolymer. Also,
The polyesteramide resin described in Example 2 of JP-A-51-22732 and the polyesteramide resin described in JP-A-51-125194 described in the section of the prior art are a type of block copolymer. However, the molecular weight distribution of the polyamide units in the polymer will be wide.

The hot melt adhesive made of the polyester amide resin of the present invention is based on the polyester resin disclosed in JP-A-51-22732 and JP-A-51-125194, as evidenced by the comparison between Examples and Comparative Examples described below. Compared to hot melt adhesives made of amide resin, resin color, moisture resistance,
The effect is that heat resistance and washing resistance are significantly improved. The reason for this is thought to be due to the difference in polymer structure as described above.

Example Next, the present invention will be further explained with reference to Examples.

Hereinafter, "part" and "1%" refer to melt viscosity retention rate (%)
Except for , all figures are expressed on a weight basis.

In the following, the melt viscosity was measured using a flow tester manufactured by Shimadzu Corporation, with a diameter of 1 mm and a load of 30 kg/cm.
, and was measured at a temperature of 190°C. The number average molecular weight was measured by GPC (gel permeation chromatography).

Example 1 Ester A In reaction vessel 1, 184 parts of terephthalic acid and 88 parts of adipic acid were added.
1.6-hexanediol, 0.1 part of dibutyltin oxide and 0.03 parts of tetrabutyl titanium as catalysts, heated to 260°C in a nitrogen stream, and heated at the same temperature for 1 hour. 163 parts of 1,4-butylene gelicol was added to the reacted nitride and heated at 200 to 230°C.
The mixture was allowed to react for 3 hours.

As a result, the number average molecular weight is 750. Acid value 8. OKOHm
g/g of esterification reaction product (A) was obtained.

The reaction vessel 2 of polyamide was replaced with nitrogen gas, and the number average molecular weight was 470.
00, 6 nylon having a weight average molecular weight of 72,000 (Mitsubishi Kasei Corporation r Tsubami, DO 1020J) and 44 parts of adipic acid were charged, and a depolymerization reaction was carried out at 240° C. for 2 hours.

Next, 62 parts of 1,4-butylene gelicol was charged into the system, and an esterification reaction was carried out at 200 to 230°C for 3 hours.

As a result, number average molecular weight 745, acid value 15KOH+w
g/g of depolymerized polyamide resin (B) was obtained.

The contents of reaction vessel 2 of polynis-suramide were transferred to reaction vessel 1, and 0.0% of phosphoric acid was added.
1 part of tetrabutyl titanate, and 0.2 part of antimony trioxide were added, and a polycondensation reaction was carried out at 240° C. for 3 hours under reduced pressure of 1 mmHg or less.

This allows the melt viscosity η. 750 pg/190℃, acid value 1.5KOHmg/g, softening point 95℃, melting point 124
A pale-colored polyesteramide resin at a temperature of 0.degree. C. was obtained.

Hotmelt The polyesteramide resin obtained above was frozen and ground, and the powder of 60 mesh or less was sieved and subjected to the test described below.

Comparative Example 1 In a reaction vessel, 259 parts of terephthalic acid and 123 parts of adipic acid were added.
1,4-butylene glycol, 162 parts, ethylene glycol, 119 parts, ε-caprolactam, 163 parts, and 0.18 parts of zinc acetate as a catalyst were charged, and reacted at 160 to 230°C in a nitrogen stream.

As a result, an esterification reaction product having an acid value of 12.3 KOHmg/g was obtained.

Next, 0.13 parts of phosphoric acid, tetrabutyl titanate) 0
．． 08 parts and 0.2 parts of antimony trioxide were added.

Polycondensation reaction was carried out at 235° C. for 3 hours under reduced pressure of 1 mmHg or less.

As a result, the melt viscosity 'Q. 820 pg/190"O
.

Acid value 2.8KOHmg/g, softening point 66℃, melting point 10
A yellow-brown polyesteramide resin at 4° C. was obtained.

This polyesteramide resin was frozen and ground, and the powder of 60 mesh or less was sieved and subjected to the test described below.

Comparative Example 2 In a reaction vessel, 196 parts of terephthalic acid and 115 parts of adipic acid were added.
1.4-butylene glycol, 283 parts, and 0.15 parts of tetrabutyl titanate as a catalyst were charged, and the mixture was reacted for 4 hours while distilling off the water produced at 190 to 210° C. in a nitrogen stream.

As a result, an esterification reaction product having an acid value of 19 KOH layer gnog was obtained.

Next, the system was reduced to a reduced pressure of 210 mmHH and reacted for an additional 1 hour, and then 133 parts of (-caprolactam) was charged and reacted for 2 hours at normal pressure.
The pressure was reduced to 3 parts Hg, and the polycondensation reaction was carried out at a reaction temperature of 240° C. for 1 hour.

This allows the melt viscosity η. 850 ps/190℃, acid value 2.3KO! (1g/g, softening point 74℃, melting point 11
A yellow-brown polyesteramide resin at 4° C. was obtained.

This polyesteramide resin was frozen and ground, and the powder of 60 mesh or less was sieved and subjected to the test described below.

Comparative Example 3 In a reaction vessel, 184 parts of terephthalic acid and 132 parts of adipic acid were added.
1,64 parts of 1,6-hexanediol, 137 parts of nylon 6 (Tsubamitsudo-1020), 225 parts of 14-butylene gelicol, and 0.1 part of dibutyltin oxide and 0.03 part of tetrabutyl titanate as catalysts. The esterification reaction was carried out at 220 to 230°C for 3 hours in a nitrogen stream to obtain an esterification reaction product with an acid value of 15 KOHmg/g.

Next, add 0.1 part of phosphoric acid and 0.0 parts of tetrabutyl titanate to the system.
．． 1 part and 0.2 part of antimony trioxide to prepare 2
Polycondensation reaction was carried out at 40°C for 2.5 hours.

As a result, melt viscosity η 860 ps/190°C, acid value 3.2 KOH g/g, softening point 75°C or less, melting point 1
A light brown polyesteramide resin at 10° C. was obtained.

This polyesteramide resin was frozen and ground, and the powder of 60 mesh or less was sieved and subjected to the test described below.

Example 2 Esul A In reaction vessel 1, 183 parts of terephthalic acid and 12 parts of adipic acid were added.
9 parts, 159 parts of 1,4-butylene glycol, 0.08 parts of dibutyltin oxide as a catalyst, and o and u parts of tetrapyne a-buil titanate were charged, and after reacting at 200°C for 2 hours in a nitrogen stream, ethylene was added. 82 parts of glycol was charged and reacted at 220 to 230°C for 2 hours.

As a result, an esterification reaction product (A) having an acid value of 23 KOH g/g was obtained.

The reaction vessel 2 for polyamide B was replaced with nitrogen gas, 99 parts of nylon 66 and 32 parts of adipic acid were charged, and a depolymerization reaction was carried out at 270°C for 2 hours. Next, 40 parts of 1,4-butylene gelicol was charged into the system, and an esterification reaction was carried out at 200 to 230°C for 3 hours.

As a result, number average molecular weight 742, acid value 1B, 8KOH
A depolymerized polyamide resin (B) of mg/H was obtained.

The contents of polyesteramide reaction vessel z were transferred to reaction vessel 1, and 0.0% of phosphoric acid was added.
1 part of tetrabutyl titanate, 0.1 part of tetrabutyl titanate, and 0.2 part of antimony trioxide were added, and a polycondensation reaction was carried out at 240° C. for 3 hours under reduced pressure of lsmHg or less.

This allows the melt viscosity η. 820 ps/190℃, acid value 1.4KOHmg/g, softening point 99℃, melting point 126
A pale yellow polyesteramide resin was obtained.

Hotmelt The polyesteramide resin obtained above was frozen and ground, and the powder of 60 mesh or less was sieved and subjected to the test described below.

Example 3 Ester A In reaction vessel 1, 228 parts of terephthalic acid and 10 parts of adipic acid were added.
0 parts, 206 parts of 1,4-butylene glycol, and 0.1 part of dibutyltin oxide and 0.08 parts of tetraisopropyl titanate as catalysts, and reacted at 180 to 210°C for 2 hours in a nitrogen stream, and then 57 parts of ethylene glycol was charged and reacted at 230°C for 3 hours.

As a result, an esterification reaction product (A) having an acid value of 20 and 1 g/g of KOH was obtained.

The reaction vessel 2 for polyamide B was replaced with nitrogen gas, 156 parts of nylon 6 and 33 parts of adipic acid were charged, and a depolymerization reaction was carried out at 240°C for 2 hours. Then, 42 parts of 1,4-butylene gelicol was charged into the system, and an esterification reaction was carried out at 200 to 230°C for 3 hours.

This resulted in a number average molecular weight of 980 and an acid value of 15.6.
wg/g of depolymerized polyamide resin (B) was obtained.

Polyesteramide reaction vessel? Transfer the contents into reaction vessel 1 and add 0.0% phosphoric acid.
1 part of tetrabutyl titanate, and 0.2 part of antimony trioxide were added, and a polycondensation reaction was carried out at 240° C. for 3 hours under reduced pressure of 1 mmHg or less.

As a result, the melt viscosity η, 780 ps/190°C,
Acid value 1.3KOHmg/g, softening point 96℃, melting point 11
A pale yellow polyesteramide resin at 4° C. was obtained.

The polyesteramide resin obtained from Hot Melt Wakasukuki was frozen and crushed, and the powder of 60 mesh or less was sieved and subjected to the test described below.

<Evaluation Test, Adhesion Test) Betsu 1 Keikouou A1 The powdered hot melt adhesives obtained in Examples 1 to 3 and Comparative Examples 1 to 3 were measured for their melt viscosity η and heated to 180°C for 30 minutes. The melt viscosity η when maintained was measured, and the melt viscosity retention rate toox (η1/
η,) was determined to evaluate moisture resistance.

In addition, the melt viscosity ηt after being left for 7 days under the conditions of 40° C. and 80% R) was measured, and the melt viscosity retention rate toox (η21η0) with respect to the initial value was determined to evaluate moisture resistance.

11 Hill Powdered hot melt adhesives of Examples 1 to 3 and Comparative Examples 1 to 3 were applied to the cotton core at 5 g/m', 14 points/25+a.
After forming dots at a ratio of m, they were melted and temporarily bonded.

Next, a cotton cloth or polyester cloth was placed on the processed surface, and the temperature was 130°C or 150°C, and the press pressure was 300 g.
/Cm", bonded by thermocompression for 10 seconds, T
Initial adhesive strength was measured by beer test.

In addition, when the sample after bonding in the above was washed with water at 40°C, 0.3% detergent, 60 minutes in a laundry meter, and 40℃, perchlorethylene, 60 minutes in a laundry meter. The adhesive strength was measured after dry cleaning under the following conditions.

Test results> The results are shown in Table 1.

As is clear from Table 1, the hot melt adhesives of each example had a lighter resin color than those of each comparative example, and had greater adhesion to both natural fibers and synthetic fibers.
Moreover, it can be seen that it has excellent moisture resistance, heat resistance, and washing resistance.

Procedural amendment (voluntary) March 30, 1990 1999 Patent Application No. 66871 2, Name of the invention Polyesteramide resin and hot melt adhesive made of the resin 3, Person making the amendment Relationship with weight Patent Applicant Address: 9-6 Nozaki-cho, Kita-ku, Osaka Name (410) Representative: Nippon Gosei Chemical Industry Co., Ltd.
Masaru Ohashi - 4, Agent 〒533 6, Contents of amendment (1) "Happened" on page 11, line 16 of the specification of the present application is corrected to "difficult to proceed."

(2) On page 25, line 11, "1st position [" tang h] is corrected to ``Cast J character.''

(3) "Moisture resistance" on page 25, line 16 is corrected to "heat resistance."

that's all

Claims (1)

[Claims] 1. A number obtained by depolymerizing an esterification reaction product (A) obtained by esterifying a polybasic acid component and a polyhydric alcohol component and a polyamide resin in the presence of a polybasic acid. Average molecular weight 25
A polyesteramide resin consisting of a polycondensation reaction product with a depolymerized polyamide resin (B) having a molecular weight of 0 to 1,500. 2. The number average molecular weight of the esterification reaction product (A) is 300~
2000. The polyesteramide resin according to claim 1. 3. Esterification reaction product (A) and depolymerized polyamide resin (
The polyesteramide resin according to claim 1, wherein the reaction ratio with B) is 90:10 to 30:70 by weight. 4. A hot melt adhesive comprising the polyesteramide resin according to claim 1. 5. The hot melt adhesive according to claim 4, which is used for adhering cloth to cloth.