JPH03294352A - Resin composition and multilayer structure using the same - Google Patents

Abstract

PURPOSE:To obtain a resin composition useful as an adhesive resin of multi- layered structural matter comprising a reaction product of a specific end group- containing polyester, a specific functional group-containing polyolefin and a specific functional group-containing low-molecular weight compound. CONSTITUTION:(A) 80-20 pts.wt. polyester having a repeating unit expressed by the formula (R<1> and R<2> are 1-40C bifunctional organic group) and OH and/or COOH at chain ends is mixed with (B) 20-80 pts.wt. polyolefin having a functional group (preferably COOH, OH or activated N-methylol group, etc.) reactive with OH, COOH and/or NH2 and (C) 0.01-10 pts.wt. low-molecular weight compound (preferably diisocyanate) reactive with at least two OH and/or COOH in heating and reacted to obtain a resin composition. Then, a polyolefin resin layer, etc., is applied on at least a face of the resin composition of a layer composed of the composition to afford the aimed multilayered structural matter.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to an adhesive resin and a multilayer structure useful as packaging materials such as films, sheets, containers, etc.

(Prior Art) Polyester, particularly polyethylene terephthalate, has excellent chemical resistance, heat resistance, mechanical properties, electrical properties, etc., and is used in many industrial products as fibers, films, etc.

In addition, polyethylene terephthalate has gas barrier properties,
Because it has excellent transparency, it is used as a material for containers for seasonings, soft drinks, detergents, cosmetics, etc.

However, since polyethylene terephthalate has a high melting point, it has poor heat-sealing properties, and is rigid, which poses problems when used as some packaging materials. Therefore, in order to solve these drawbacks, the development of a multilayer film made of polyethylene terephthalate and polyolefin was investigated. However, even in this case, there remained a problem to be solved.

That is, the problem of adhesion between polyethylene terephthalate and polyolefin is that since the two have significantly different polarities, it is essentially difficult to bond them, and there has been no good adhesive resin.

(Problems to be Solved by the Present Invention) The present invention is intended to solve the above-mentioned conventional problems, and its purpose is to provide a resin that has excellent adhesion to both aromatic-containing polyester and polyolefin resin. Another object of the present invention is to provide a multilayer structure using the same.

(Means for Solving the Problems) The present invention comprises (A) a polyester whose terminal end is a hydroxyl group and/or a carboxyl group; and (B) a polyester having a functional group capable of reacting with a hydroxyl group, a carboxyl group, and/or an amino group in the molecule. A resin composition characterized by reacting a polyolefin with (C) a low molecular compound capable of reacting with at least two or more hydroxyl groups and/or carboxyl groups, and an aromatic ring-containing polyester or an aromatic ring-containing polyester on at least one side of the resin layer. It is a multilayer structure having a polyolefin resin layer.

The polyester (A) used in the present invention has a repeating unit represented by the formula (I) (in the formula, R1 and R2 represent a divalent organic group having 1 to 40 carbon atoms) and has 10 at the terminal. It has an H group and/or a -COOH group.

This polyester is obtained by a known method of condensing dicarboxylic acid compounds or their esters with diols. Examples of such dicarboxylic acid compounds include malonic acid, succinic acid, glutaric acid, adipic acid, and pimelic acid. , sebacic acid, azelaic acid, speric acid, dodecane dicarboxylic acid, 3-methyl azelaic acid, cyclohexane-1,3-dicarboxylic acid, cyclopencune-1,3
- dicarboxylic acids, terephthalic acid, methoxyterephthalic acid, ethoxyterephthalic acid, fluoroterephthalic acid, chloroterephthalic acid, methylterephthalic acid, isophthalic acid,
Phthalic acid, methoxyisophthalic acid, diphenylmethane
4,4'-dicarboxylic acid, diphenylmethane-3,3'
-dicarboxylic acid, diphenyl ether-4,4°-dicarboxylic acid, diphenyl-4,4″-dicarboxylic acid, naphthalene-2,6-dicarboxylic acid, naphthalene-1,5-
dicarboxylic acid, naphthalene-1,4-dicarboxylic acid, 2
．． 5-norbornanedicarboxylic acid, 4,4"-oxybenzoic acid, 4,4°-methylene dibenzoic acid, diglycolic acid, thiodipropionic acid, dibenzoic acid, p-oxy(p
-carboxyphenyl)benzoic acid, tetramethylene-bis(p-oxybenzoic acid), dimer acid, hydrogenated dimer acid, and esters thereof.

These dicarboxylic acids or esters thereof may be used alone or in a mixture of two or more.

On the other hand, the diols used include ethylene glycol, diethylene glycol, polyethylene glycol, 1.3-propanediol, 1.2-
Propanediol, 1,3-butanediol, 1,4-
Butanediol, 2-ethylhexane-1,3-diol, 2,2.4-trimethyl-1,3-bentanediol, neopentyl glycol, 1,6-hexanediol, 112-dodecanediol, cyclohexane-1°4 -diol, cyclohexane-1,3-diol, 1
, 4-cyclohexane dimetatool, P-xylene diol, 4,4°-thiodiphenol, 4.4゛-methylenediphenol, 4,4゛-dihydroxybiphenyl, 4
, 4"-isopropylidene diphenol, 4,4"-isopropylidene bis(2,6-dichlorophenol),
2.5-naphthalenediol, 2.5-norbornanediol, hydroquinone, resorcinol, methylhydroquinone, chlorohydroquinone, acetylhydroquinone, acetoxyhydroquinone, nitrohydroquinone, dimethylaminohydroquinone, 1.4-dihydroxynaphthol, 1.5-dihydroxynaphthol , 1.
6-dihydroxynaphthol, 2,6-dihydroxynaphthol, 2.7-dihydroxynaphthol, 2.2-
Bis(4-hydroxy-3,5-dichlorophenyl)-
Propane, 2,2-bis(4-hydroxy-3-methylphenyl)-propane, 2,2-bis(4-hydroxy-3-chlorophenyl)propane, bis(4-hydroxy-3,5-dimethylphenyl)- Methane, bis(4-
Hydroxy-3゜5-dichlorophenyl)-methane, bis(4-hydroxy-3,5-dibromophenyl)-methane, 1,1-bis(4-hydroxyphenyl)cyclohexane, 4,4'-dihydroxydiphenylbis(
4-hydroxyphenyl)ketone, bis(4-hydroxy-3,5-dimethylphenyl)ketone, bis(4-hydroxy-3,5-dichlorophenyl)ketone, bis(
4-hydroxyphenyl) sulfide, bis(4-hydroxy-3-chlorophenyl) sulfide, bis(4-
Hydroxyphenyl) sulfone, bis(4-hydroxy-3°5-dichlorophenyl) ether, dimer acid hydrogenated reduced diol, polyolefin polyol, and the like. These diols may be used alone or in a mixture of two or more.

The polyester (A) of the present invention also includes a polyester obtained by reaction polymerization of (a) a monoepoxy compound represented by the following general formula (If), (b) a polyester or a polyester precursor, and (C) a dicarboxylic acid compound. Can be used.

(In the formula, R3 represents a monovalent organic group.) Examples of the monoepoxy compound represented by the general formula (II) include epoxy compounds in which the substituent R1 is an alkyl group having about 1 to 50 carbon atoms. Alkyl glycidyl ethers having about 1 to 50 carbon atoms, represented by
Epoxidized compounds of (poly)alkylene glycol monoalkyl ethers such as those represented by i-〇-CJs\/, and in which the key R” already represented is a perfluoroalkyl group having about 1 to 50 carbon atoms. Epoxy compounds, such as those in which R1 is an alkenyl group having about 1 to 50 carbon atoms, such as those in which R1 is -CHz OAr (Ar
is an aromatic group with about 6 to 50 carbon atoms which may have a substituent), and R1 is a silicon atom or nitrogen atom with about 1 to 50 carbon atoms, as shown in Examples include epoxy compounds containing organic groups.

These may be used alone or in combination of two or more.

Among these epoxy compounds, particularly preferred are monoepoxy compounds having a long chain alkyl group having 4 to 50 carbon atoms.

Further, Φ) The polyester or polyester precursor is a polyester obtained by condensing the dicarboxylic acid compound and diols, and the polyester precursor is a compound represented by the following general formulas (III) to (V), Examples include the aforementioned polyester oligomers, bishydroxyethyl terephthalate, bishydroxypropyl terephthalate, bishydroxybutyl terephthalate, and the like.

Furthermore, methyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, methyl 3-hydroxybenzoate, ethyl 3-hydroxybenzoate, etc. can also be used.

As the dicarboxylic acid compound (C), the dicarboxylic acids or esters thereof exemplified as the above-mentioned polyester constituents may be used alone or in a mixture of two or more.

The monoepoxy compound, dicarboxylic acid, and polyester or polyester precursor can be reacted in any quantitative ratio, but the monoepoxy compound may be reacted with 5 to 1 part by weight per 100 parts by weight of the polyester or polyester precursor.
00 parts by weight, more preferably 10 to 100 parts by weight, and 5 to 100 parts by weight of dicarboxylic acid, more preferably 10 to 1 part by weight.
It is particularly preferable to use 00 parts by weight of the monoepoxy compound and to react the monoepoxy compound in a molar ratio of 2 to the dicarboxylic acid.

The reaction may be performed by reacting the monoepoxy compound (n) with the dicarboxylic acid and then reacting with the polyester or polyester precursor, or by reacting the monoepoxy compound (n) with the dicarboxylic acid, or by reacting the monoepoxy compound (n) with a polyester or a polyester precursor.
The dicarboxylic acid and the polyester or polyester precursor may be reacted at the same time.

In either case, the reaction is first carried out at normal pressure at 50 to 300°C, preferably at 120 to 270°C for 5 minutes to 10 hours, and then at 150 to 350°C, preferably 170 to 300°C under reduced pressure.
Polymerization is completed at ℃.

At this time, the molar ratio of the epoxy compound to the dicarboxylic acid used in the reaction is set to 1.5 to λ0, and the reaction is carried out at normal pressure until the acid value of the reaction mixture becomes less than 10% of the initial acid value, and then the pressure is reduced. By starting the process, relatively high molecular weight polymers can be stably obtained.

When reducing the pressure, it is preferable to reduce the pressure gradually, and it is preferable that the time required to reduce the pressure from normal pressure to 1 Hg is 30 minutes or more. In particular, it is preferable to gradually reduce the pressure from 10 Hg to 1 Hg.

Although the reaction and polymerization can proceed without a catalyst, they may be carried out with the addition of a catalyst if necessary.

The catalysts used include tertiary amines such as benzyldimethylamine, dimethylaminopyridine, and tributylamine, and metal catalysts such as tetrabutoxytitanium, germanium dioxide, antimony trioxide, calcium acetate, magnesium acetate, and zinc acetate. can be mentioned.

These may be used alone or in combination of two or more. The amount of catalyst used is 1 to 5o, ooopp-, based on the polymer.

In the present invention, (B) the polyolefin having a functional group capable of reacting with a hydroxyl group, a carboxyl group, and/or an amino group in the molecule includes a hydroxyl group (-〇H), an isocyanate group (-NGO), an active N-ester group ( -0CN), polyethylene, polypropylene, and polyolefins obtained by copolymerizing ethylene with α-olefins such as propylene and butene, or dienes such as butadiene, having functional groups such as carbodiimide groups (-N=C=N-R). etc. Among these, those containing an acid anhydride group, an epoxy group, a carboxyl group, a hydroxyl group, an active N-methylol group, and an active N-alkoxymethyl group are preferably used.

The number of functional groups in a polyolefin molecule is preferably about 0.5 to 50 on average per molecule. If the number of functional groups is too small, the effects of the present invention cannot be obtained, and if the number is too large, problems such as gelation will occur.

The molecular weight of the polyolefin is preferably about 5,000 to 500,000. If the molecular weight is too small, the invention will not be effective, and if the molecular weight is too large, moldability will deteriorate.

These functional group-containing polyolefins can be obtained by known methods. For example, it can be obtained by radical copolymerization of the above-mentioned functional group-containing vinyl monomer with ethylene, or by graft polymerization of a functional group-containing vinyl monomer with a polyolefin such as polyethylene in an organic solvent or in the presence of a radical generator. . Further, such polyolefins are also available as commercial products.

These functional group-containing polyolefins can also be used in combination with polyolefins that do not have functional groups. At this time, the weight ratio of the polyolefin having no functional group is preferably 50% or less of the sum of the polyolefin having a functional group and the polyolefin having no functional group.

The low-molecular compound (C) that can react with at least two hydroxyl groups and/or carboxyl groups used in the present invention is a compound that has at least two or more functional groups that can react with hydroxyl groups and/or carboxyl groups in its molecule. or a compound in which a functional group in a molecule reacts with a hydroxyl group and/or a carboxyl group to generate a new functional group that reacts with the hydroxyl group and/or carboxyl group.

Examples of the former compounds include polyisocyanates such as diphenylmethane diisocyanate, toluylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, triphenylmethane triisocyanate, and polymethylene polyphenylisocyanate, and these polyisocyanates together with trimethylolpropane, ethylene glycol, and propylene. Polyisocyanates such as adducts or prepolymers with polyols such as glycols, and blocked isocyanate compounds in which the isocyanate groups of these polyisocyanates, adducts, and prepolymers are blocked with phenols, lactams, etc., and their derivatives, bisphenol. Bisphenol-type epoxy compounds obtained by reacting A with epichlorohydrin in various proportions, novolak-type epoxy compounds obtained from novolak resin and epichlorohydrin, polyglycidyl esters obtained from polycarboxylic acid and epichlorohydrin, alicyclic compounds (e.g. dicyclopenta Aliphatic compounds with alcoholic hydroxyl groups (e.g. butanediol, glycerin, etc.) and glycidyl ethers obtained from epichlorohydrin, epoxidized polybutadiene, unsaturated monomers containing epoxy groups and other unsaturated Epoxy compounds such as epoxy group-containing polymers consisting of sulfuric acid, hexamethylene diethylene urea, phenylene diethylene urea,
Polyaziridine compounds such as trimethylolpropane tri-aziridinylpropionate, polyaldehydes such as terephthalaldehyde and glutaraldehyde, dimethylolmelamine, trimethylolmelamine, hexamethylolmelamine, dimethoxymelamine, trimethoxymelamine, hexa Active methylol and active alkoxymethyl group-containing compounds such as methoxymelamine, polyacyloyl lactams such as phenylene diacylolylphyl prolactam and tetramethylene diacyloyl prolactam, other polyfunctional cyanate ester compounds, tetraethoxysilane and their partial condensations Examples include things. Among these, preferred compounds are diisocyanate compounds, jepoxy compounds, active dimethylol compounds, and active dialkoxymethyl compounds. Particularly preferred are diisocyanate compounds.

An example of the latter compound is isatoic anhydride.

In the present invention, the ratio of (A) polyester (B) functional group-containing polyolefin and (C) functional group-containing compound to be heated and blended is usually 80 to 20 parts by weight of (A) polyester;
(B) 20 to 80 parts by weight of the functional group-containing polyolefin and (C) 0.01 to 10 parts by weight of the functional group-containing compound.

This is because outside these ranges, the effect of improving adhesion to substrates such as polyolefins and aromatic ring-containing polyesters is small.

The heating and blending is carried out at a temperature higher than the temperature at which both the resins (A) and (B) melt, usually from 150 to 300''C, using a Brabender plasticorder, an extruder, or the like.

If necessary, it can also be carried out in an organic solvent such as toluene or xylene.

During heating and blending, both the resins (A) and (B) and the compound (C) undergo a reaction, and a known reaction accelerator may be added for the purpose of promoting this reaction.

As a reaction accelerator, 1,8-diazabicyclo(5,4,
O) Tertiary amines such as undec-7-ene, benzyldimethylamine, dimethylaminopyridine, tributylamine, dibutyltin dilaurate, dibutyltin dioctoate, tetrabutoxytitanium, germanium dioxide, antimony dioxide, calcium acetate, magnesium acetate, acetic acid metal catalysts such as zinc or sulfosalicylic acid,
Examples include organic sulfonic acid compounds such as P-)luenesulfonic acid and 0-sulfoanzoic anhydride.

Furthermore, after the resins (A), (B), and (C) are reacted by heating and blending, a polyolefin such as polyethylene or polypropylene can be blended.

The multilayer structure in the present invention is a resin composition layer obtained by reacting (A) a polyester, (B) a functional group-containing polyolefin, and (C) a functional group-containing compound, and has a known aromatic aroma on at least one side of the resin composition layer. It has a group ring-containing polyester resin layer and/or a polyolefin resin layer.

The aromatic ring-containing polyester used in the present invention is one selected from the above-mentioned (b) polyesters, and has an aromatic ring in the dicarboxylic acid or its ester and/or diol, which is a polyester forming component. In particular, polyesters formed from aromatic dicarboxylic acids or esters thereof.

Examples of the polyolefin used in the present invention include low-density polyethylene, medium-low density polyethylene, high-density polyethylene, polypropylene, and ethylene-vinyl acetate copolymer. Therefore, the multilayer structure of the present invention includes the resin composition of the present invention/polyester and the resin composition of the present invention/polyolefin.

It is a multilayer structure consisting of a combination of the resin composition of the present invention/polyester/the resin composition of the present invention/polyolefin, etc. The thickness of each layer constituting the multilayer structure is not particularly limited, but in the case of a multilayer film, it is usually 1 to 50 μm. In coextrusion, the composition layer of the present invention used as the adhesive resin layer is usually thinner than other layer components, and is used in a thickness of 5 to 25 μm. These can also be used as multilayer structures laminated with aluminum foil, paper, iron plates, other plastic films, sheets, etc.

These multilayered structures can be easily manufactured by laminating and heat pressing films and sheets, but industrially, multiple extruders are used to join molten resin in the same die. A coextrusion method or a coextrusion/costretching method for further stretching is used, and molded products such as multilayer films, sheets, and bottles can be obtained. In addition, if necessary, the resin composition of the present invention may be dispersed or dissolved in an organic solvent, applied to a polyester or polyolefin film or sheet, dried,
Further lamination is also possible.

〔Example〕

EXAMPLES The present invention will be explained in more detail with reference to examples below, but the present invention is not limited to the following examples unless the gist of the invention is exceeded.

Reference example 1 A glass polymerization tube equipped with a stirring blade, a nitrogen inlet, and a pressure reduction port,
1.96 g (0,0118 mol) phthalic acid, 30.0
g (0,118 mol) of bishydroxyethyl terephthalate, 6.51 g of a linear monoepoxy compound having 16 and 18 carbon atoms (manufactured by Daicel, trade name AOEX-68), and 0.005 g of tetrabutoxytitanium were charged, and the mixture was heated under reduced pressure.
Nitrogen substitution was repeated three times.

The polymerization tube was heated to 150°C and reacted at normal pressure for 4 hours, and then the pressure was gradually reduced to maintain the pressure at 0.5 mm HH.

The reaction temperature was gradually raised to 270°C, and polymerization was carried out for 2 hours. Thereafter, nitrogen was introduced into the polymerization tube to return the pressure to normal pressure, and the polymerization was stopped. The product could be extracted from the bottom of the polymerization tube. The obtained polymer was light brown and transparent, with a concentration of phenol/tetrachloroethane=50150 (weight ratio) in a solvent of 0.5 g·z-' and an intrinsic viscosity ηin at 30°C.
h was 0.47d1g-'.

Reference Example 2 1.72g (0,
0118 mol) of adipic acid, 30.0 g (0°118 mol)
mol) of bishydroxyethyl terephthalate, 6.51 g of a linear monoepoxy compound having 16 and 18 carbon atoms (manufactured by Daicel, trade name AOE Repeated times.

The polymerization tube was heated to 150°C and reacted for 3.5 hours at normal pressure, and then the pressure was gradually reduced and maintained at 0.5 wa Hg.
The reaction temperature was gradually raised to 270''C and polymerization was carried out for 2 hours.Nitrogen was then introduced into the polymerization tube to return to normal pressure and polymerization was stopped.The product could be extracted from the bottom of the polymerization tube. The obtained polymer was light brown and transparent, and ηinh
=0.42 dlg-' (conditions are the same as Reference Example 1)
Met.

Reference Example 3 Into a polymerization tube similar to that used in Reference Example 1, 1.72 g (0
,0118 mol) of adipic acid, 30.0 g (0°11
8 mol) of bishydroxyethyl terephthalate, 5.7 g of C 12 and 140 linear monoengineered poxy compounds (manufactured by Daicel, trade name AOE X-24), and 0.8 mol of tetrabutoxytitanium. 5 g of OO was charged and the same operation as in Reference Example 2 was performed. The product could be extracted from the bottom of the polymerization tube. The obtained polymer was pale yellow and transparent, and η1
nh=0.63d1g-' (conditions are the same as Reference Example 1)
Met.

Reference Example 4 In a polymerization tube similar to that used in Reference Example 1, 1.72 g (0
,0118 mol) of adipic acid, 6.51 g carbon number 1
6 and 18 linear monoepoxy compounds (manufactured by Daicel,
A zero-polymerization tube charged with AOE The temperature was raised to 280°C and the reaction was continued for 1 hour. Thereafter, the pressure was gradually reduced and stirring was continued for 1 hour, and the pressure was restored by introducing nitrogen into the polymerization tube to stop the polymerization. The product could be extracted from the bottom of the polymerization tube.

The obtained polymer was pale yellow and transparent, η1nh=0°45
dlg-' (conditions were the same as in Reference Example 1).

Reference Example 5 In a polymerization tube similar to that used in Reference Example 1, 35 g of dimethyl terephthalate, 7.0 g of 2-methyl-1,3-propanediol, and 22 g of 1,6-hexanediol were added to 0.05 g of Prepared with tetrabutoxytitanium, heated at 180°C for 1 hour under normal pressure and nitrogen flow, then heated at 230°C.
The mixture was heated at C for 2.5 hours to elute about 90% of the theoretical amount of methanol, a by-product. Next, after adding 0.05 g of tridecyl phosphite to the reaction mixture, the temperature was raised to 250°C, and the pressure in the system was reduced to 0.2 ■Hg over 40 minutes, and polymerization was carried out under these conditions for 3.5 hours. I did it. The intrinsic viscosity of the obtained polyester was 0.60 dl/g.

Example 1 25g of polyester obtained in Reference Example 1, 42oopp
-25g of polyolefin containing an acid anhydride group (modified with maleic anhydride, trade name Tubatic AP730T, manufactured by Mitsubishi Kasei Corporation) and modified diphenylmethane diisocyanate (trade name 15ONATE@143L, manufactured by Mitsubishi Kasei Dow Corporation) 0 .45 g was placed in a Prabender plasticorder set at 190°C and kneaded and reacted at 30 rpm+ for 5 minutes.

The resulting reaction product was an off-white solid at room temperature.

This reaction product was heat-pressed at 200°C to form a film with a thickness of about 100 μm, which was then sandwiched between a low-density polyethylene film and a polyethylene terephthalate film and heated again at 200°C.
A multilayer film was obtained by hot pressing at °C/2 minutes and a pressure of 10 kg/c11I. The obtained multilayer film was cut into strips with a width of 10 m and the T-peel strength was measured, and the result was 1.5.
kg/Cm, indicating cohesive failure.

Comparative Example 1 A multilayer film was produced by reacting in exactly the same manner as in Example 1, except that modified diphenylmethane diisocyanate was not used in Example 1.

The T peel strength was 0.3 kg/cm.

Examples 2 to 5 25 g of polyester obtained in Reference Examples 2 to 4, acid anhydride group-containing polyolefin (trade name Tubatic AP730)
25 g of T) and 0.45 g of modified diphenylmethane diisocyanate (trade name 15ONATE.143L) were reacted in the same manner as in Example 1.

All of the obtained reaction products were off-white solids at room temperature.

A multilayer film was obtained using these reactants in the same manner as in Example 1. Table 1 shows the results of measuring the T peel strength.

Examples 6 to 10 In Examples 1 to 5, the component (C) was isatoic anhydride, and the temperature of the Brabender plasticorder was set at 210°C.
The reaction was performed in the same manner except that All of the obtained reaction products were off-white solids at room temperature. A multilayer film was obtained using these reactants in the same manner as in Example 1. T1111
Table 1 shows the results of measuring the strength.

Example 11 25 g of polyester obtained in Reference Example 2, glycidyl group-containing polyethylene (trade name LEXPAR 8RA305
0, manufactured by Nippon Petrochemical Co., Ltd.) 25 g and modified diphenylmethane diisocyanate (trade name I 5ONATEe)
143 L) 0.45 g was charged into a Brabender plasticorder set at 210°C, and heated at 30 rpm for 5 g.
The mixture was reacted for a minute.

The resulting reaction product was an off-white solid at room temperature.

A multilayer film was produced using this reaction product in the same manner as in Example 1. As a result of measuring this T peel strength, it was 1°8 kg/c.
The base material was destroyed at m.

Example 12 A multilayer film was obtained in the same manner as in Example 11, except that carboxyl group-containing polyethylene (trade name: Nucrel 410, manufactured by DuPont Mitsui) was used instead of the glycidyl group-containing polyethylene. When the T peel strength was measured, it was found that the base material was destroyed at 1°6 kg/cm.

Example 13.14 The same procedure as in Examples 11 and 12 was carried out except that 0.75 g of isatoic anhydride was used instead of the modified diphenylmethane diisocyanate. The results are shown in Table 2.

Example 15.16 25 g of the polyester obtained in Reference Example 2, polyolefin containing a carboxyl group (trade name Nucrel@41
0) 25g and hexamethylene diisocyanate) 0.2
5g or 0.30g of isophorone diisocyanate at 21
The mixture was placed in a Prabender plasticorder set at 0° C., and kneaded and reacted at 30 rpm+ for 5 minutes. All of the obtained reaction products were grayish-white solids at room temperature. A multilayer film was produced using this reaction product in the same manner as in Example 1. Table 2 shows the results of measuring the T peel strength.

Examples 17 to 20, Comparative Example 2.3 A multilayer film was produced in the same manner as in Example 1, except that the polyester and component (C) were changed as shown in Table 3. Table 3 shows the results of measuring the T peel strength.

〔Effect of the invention〕

The resin composition of the present invention is useful as an adhesive resin for multilayer structures, and the resulting multilayer structure with aromatic ring-containing polyester and/or polyolefin resins is useful as packaging materials and the like.

The resin composition of the present invention can also be used as a modifier for various plastics, a polymer alloy, a compatibility improver for polymer alloys, an adhesive, and the like.

Claims (2)

[Claims] (1) (A) a polyester whose terminal end is a hydroxyl group and/or a carboxyl group; (B) a polyolefin having a functional group capable of reacting with a hydroxyl group, a carboxyl group, and/or an amino group in the molecule; and (C) a polyester having at least two or more A resin composition obtained by reacting a low molecular compound that can react with a hydroxyl group and/or a carboxyl group. (2) (A) a polyester whose terminal end is a hydroxyl group and/or a carboxyl group; (B) a polyolefin having a functional group capable of reacting with a hydroxyl group, a carboxyl group, and/or an amino group in the molecule; and (C) a polyester having at least two or more A multilayer structure comprising an aromatic ring-containing polyester or polyolefin resin layer on at least one side of a resin composition layer obtained by reacting a low-molecular compound capable of reacting with a hydroxyl group and/or a carboxyl group.