TW201936594A - 2-cyanoacrylate compound and adhesive composition - Google Patents

Abstract

A 2-cyanoacrylate compound represented by Formula (1), and an adhesive composition comprising the 2-cyanoacrylate compound represented by Formula (1). In Formula (1), L1 denotes a divalent linking group having 1 to 20 carbon atoms, R1 to R3 independently denote a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, and two or more of R1 to R3 may form a ring structure by bonding.

Description

2-cyanoacrylate compound and adhesive composition

This invention relates to a novel 2-cyanoacrylate compound and an adhesive composition.

The adhesive composition containing a 2-cyanoacrylate compound is polymerized by a weak anion such as a slight moisture attached to the surface of the coated body by the specific anionic polymerizability of the main component 2-cyanoacrylate compound. And can firmly bond various materials in a short time. Therefore, it is used as a so-called instant adhesive in a wide range of fields such as industrial use, medical use, and household use.

A technical example of the adhesive composition containing a 2-cyanoacrylate compound is mentioned, and the technique of the patent documents 1-5 is mentioned.
Patent Document 1 describes a cyanoacrylate adhesive composition in which a water-soluble polyoxyalkylene glycol solvent and a water-soluble surfactant are blended in a cyanoacrylate, and water dissolution after hardening is improved. Sex. Patent Document 2 describes a 2-cyanoacrylate-based adhesive composition for foamed styrene, which contains 2-cyanoacrylate, a carbonate compound having a specific structure, and an anionic polymerization initiator, and a content of a carbonate compound. The total amount is from 15 to 60% by mass based on the total amount of the 2-cyanoacrylate and the carbonate compound. Patent Document 3 describes an adhesive composition in which a carbonate compound is blended in 2-cyanoacrylate and has excellent machinability. Patent Document 4 describes that various carbonate compounds are blended in a 2-cyanoacrylate compound in order to adjust the curing rate, adjust the adhesion strength, or dilute. Patent Document 5 describes that the adhesion can be adjusted and the flexibility can be imparted by blending ethylene carbonate with 2-cyanoacrylate.

Patent Document 1: Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Document 5: Japanese Patent Laid-Open No. 64-83057

[Problems to be solved by the invention]

The problem to be solved by the present invention is to provide a novel 2-cyanoacrylate compound.
Further, another object to be solved by the present invention is to provide an adhesive composition containing the above 2-cyanoacrylate compound.
[Means to solve the problem]

Means for solving the above problems include the following aspects.
<1> A 2-cyanoacrylate compound which is represented by the following formula (1):

[Chemical Formula 1]

In the formula (1), L ¹ represents a divalent linking group having 1 to 20 carbon atoms, and R ¹ to R ³ each independently represent a hydrogen atom, a halogen atom, an alkyl group or an aromatic group, and two of R ¹ to R ³ . The above may also be bonded to form a ring structure.

<2> The 2-cyanoacrylate compound according to <1>, wherein L ¹ is an alkylene group having 1 to 20 carbon atoms, or a combination of two or more alkylene groups and is selected from the group consisting of an ether bond and an ester bond. One or more of the groups have a carbon number of 1 to 20 divalent groups.
<3> A 2-cyanoacrylate compound according to <1> or <2>, wherein L ¹ is an alkylene group having 1 to 20 carbon atoms.
<4> The 2-cyanoacrylate compound according to any one of <1> to <3> wherein R ¹ to R ³ are each independently a hydrogen atom or an alkyl group.
<5> The 2-cyanoacrylate compound according to any one of <1> to <4> wherein R ¹ to R ³ are a hydrogen atom.
<6> The 2-cyanoacrylate compound according to any one of <1> to <5>, wherein the 2-cyanoacrylate compound represented by the above formula (1) is represented by the following formula (2): Cyanoacrylate compound.

[Chemical Formula 2]

<7> An adhesive composition comprising the 2-cyanoacrylate compound according to any one of <1> to <6>.
<8> The composition of the adhesive of <7>, which is a water-disintegrable adhesive composition.
[Effects of the Invention]

According to the present invention, a novel 2-cyanoacrylate compound can be provided.
Further, according to the present invention, an adhesive composition containing the above 2-cyanoacrylate compound can be provided.

The description of the constituent elements described below will be made in accordance with a representative embodiment of the present invention, but the present invention is not limited by such an embodiment. In addition, in the present specification, "~" is used in the sense that the numerical values described before and after are included as the lower limit and the upper limit.
In the numerical range recited in the specification, the upper limit or the lower limit described in one numerical range may be replaced with the upper limit or the lower limit of the numerical range described in other stages. In addition, in the numerical range described in the present specification, the upper limit or the lower limit of the numerical range may be substituted for the value disclosed in the examples.
In the present invention, "% by mass" is synonymous with "% by weight", and "parts by mass" is synonymous with "parts by weight".
Further, in the present invention, a combination of two or more suitable aspects is a more suitable aspect.
The details of the present invention are described below.

(2-cyanoacrylate compound represented by formula (1))
The 2-cyanoacrylate compound of the present invention is a 2-cyanoacrylate compound represented by the following formula (1).

[Chemical Formula 3]

In the formula (1), L ¹ represents a divalent linking group having 1 to 20 carbon atoms, and R ¹ to R ³ each independently represent a hydrogen atom, a halogen atom, an alkyl group or an aromatic group, and two of R ¹ to R ³ . The above may also be bonded to form a ring structure.

The 2-cyanoacrylate compound represented by the above formula (1) is a novel compound, and is not only a monomer but also a highly reactive compound which can be anionically polymerized by an anion polymerization initiating species such as water, and is suitably used as a compound. The subsequent components of the composition of the agent.

The carbon number of L ¹ in the formula (1) is exfoliated or removed by water after the curing and curing (also referred to as "water repellent property" for short), and the adhesion of the obtained cured product to the polar substrate. From the viewpoint, it is preferable that it is 1 to 12, 1 to 8 is preferable, 1 to 4 is more preferable, and 1 or 2 is particularly preferable.
L ¹ in the formula (1) is preferably an alkylene group having 1 to 20 carbon atoms or a divalent group having 1 to 20 carbon atoms from the viewpoint of stability and reactivity of the compound, and the carbon number is preferably The divalent group of 1 to 20 is a combination of two or more alkylene groups and one or more structures selected from the group consisting of an ether bond and an ester bond, and an alkylene group having 1 to 20 carbon atoms is Preferably, the alkylene group having a carbon number of from 1 to 4 is more preferred, and the methylene group or the ethyl group is particularly preferred.
Further, the alkylene group may be linear or branched, or may have a ring structure.

R ¹ to R ³ in the formula (1) are each independently, and from the viewpoint of stability and reactivity of the compound, a hydrogen atom, a halogen atom or an alkyl group is preferred, and a hydrogen atom, a fluorine atom or an alkyl group is preferred. A hydrogen atom or an alkyl group is more preferable, and a hydrogen atom is particularly preferable.
Further, the aforementioned alkyl group may be linear or branched, or may have a ring structure.
The carbon numbers of R ¹ to R ³ in the formula (1) are each independently, and from the viewpoint of stability and reactivity of the compound, it is preferably 0 to 20, more preferably 0 to 8, and more preferably 0 to 4. , 0 or 1 is especially good.
Further, in the case where two or more of R ¹ to R ³ in the formula (1) are bonded to each other to form a ring structure, the ring structure may be an aliphatic ring, an aromatic ring or a heterocyclic aliphatic ring, or even In order to condense the ring structure, an aliphatic ring is preferred, and a 5 or 6 member aliphatic ring is preferred. Further, it is preferred that R ¹ to R ³ in the formula (1) are bonded to each other in two or more groups.

L ¹ and R ¹ to R ³ in the formula (1) may have a substituent.
Examples of the substituent include an alkyl group, an aromatic group, a halogen atom, an alkoxy group, an aryloxy group, a cyano group, an alkoxycarbonyl group, an aryloxycarbonyl group, a decyl group, and a decyloxy group. In particular, a suitable example is an alkyl group, a halogen atom or an alkoxy group, and a more preferable example is an alkyl group.
Further, the aforementioned substituent may even have a substituent.

In particular, the 2-cyanoacrylate compound represented by the formula (1) is represented by the following formula (2) or formula from the viewpoints of reactivity, water-peelability, and adhesion of the obtained cured product to a substrate having polarity. (3) The 2-cyanoacrylate compound is preferred, and the 2-cyanoacrylate compound represented by the following formula (2) is particularly preferred.

[Chemical Formula 4]

The method for synthesizing the 2-cyanoacrylate compound represented by the formula (1) is not particularly limited, and a known synthesis means can be combined and synthesized.
For example, a condensed polymer is obtained by subjecting a cyanoacetate compound to formaldehyde or a paraformaldehyde in a dehydration condensation reaction in the presence of a base catalyst, and heating and depolymerizing it to give an α-position having an ethylenically unsaturated bond. A method of a 2-cyanoacrylate compound. Further, the cyanoacetate compound can be easily produced by, for example, esterifying cyanoacetic acid with a corresponding alcohol compound in the presence of an acid catalyst.
Other methods, for example, a 2-cyanoacrylate compound different from the 2-cyanoacrylate compound represented by the formula (1), such as ethyl-2-cyanoacrylate, is reacted with a diene compound to produce an adduct, The carboxylic acid derivatized as an adduct by alkali hydrolysis is reacted with a corresponding alcohol compound in the presence of an acid catalyst to be esterified, and then thermally decomposed at an appropriate temperature, whereby the formula (1) can be obtained. A 2-cyanoacrylate compound is shown. Further, by subjecting an addition product of a 2-cyanoacrylate compound and a diene compound to a corresponding alcohol compound, a transesterification reaction is carried out in the presence of a Lewis acid catalyst, and the obtained ester compound is thermally decomposed Further, a 2-cyanoacrylate compound represented by the formula (1) can also be obtained.
In still another method, a 2-cyanoacrylate compound represented by the formula (1) can be obtained by reacting cyanoacrylic acid with a corresponding alcohol compound.

The 2-cyanoacrylate compound represented by the formula (1) is suitably used for the adhesive composition, and has a carbonate ring structure, so that it has a higher polarity than the conventional 2-cyanoacrylate compound, and is particularly suitable. Used in water disintegrable adhesive composition.
In addition, the water-disintegrable adhesive composition is an adhesive composition which is excellent in peeling or removability by water after curing.
In the case of being used as a water-disintegrable adhesive composition, it is preferred to contain a water-soluble compound described later from the viewpoint of easy disintegration of water.

In the case of using the composition of the adhesive, the content of the 2-cyanoacrylate compound represented by the formula (1) is from the viewpoint of water disintegration, adhesion, and hardenability, with respect to the composition of the adhesive. The total mass is preferably 1% by mass or more and 99% by mass or less, preferably 1% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 50% by mass or less, and particularly preferably 10% by mass or more and 40% by mass or less. 10% by mass or more and 30% by mass or less are most preferable.

In the case of using the composition of the adhesive, it is preferred to further contain a water-soluble compound.
In the present invention, the "water-soluble compound" means a compound which is mixed with water at an arbitrary mixing ratio to form a solution or has a solubility in water (25 ° C) of 1 g/100 g or more.

The solubility parameter (SP value) of the water-soluble compound is preferably 8.0 (cal/cm ³ ) 0.5 or more and 23.4 (cal/cm ³ ) 0.5 or less, and 8.3 (cal/cm) from the viewpoint of water disintegration. ³ ) 0.5 or more and 15.0 (cal/cm ³ ) 0.5 or less is preferable, 9.0 (cal/cm ³ ) 0.5 or more and 14.0 (cal/cm ³ ) 0.5 or less is more preferable, and 8.0 (cal/cm ³ ) is 0.5 or more and 12.0 ( Cal/cm ³ ) 0.5 or less is particularly preferable.

The water-soluble compound which can be used in the present invention may be a low molecular compound or a high molecular compound. The low molecular weight compound preferably has a molecular weight of less than 1,000, and the polymer compound preferably has a weight average molecular weight of 1,000 or more, and preferably has a weight average molecular weight of 1,000 or more and 1,000,000 or less.
Further, the values of the number average molecular weight (Mn) and the weight average molecular weight (Mw) of the polymer compound in the present invention are measured by gel permeation chromatography (GPC).

The water-soluble compound is not particularly limited, and has a group selected from the group consisting of an ester bond, a carbonate bond, and a sulfonate bond from the viewpoint of water dissociable property and compatibility with a 2-cyanoacrylate compound. A compound of at least one bond in the group is preferred, and a compound having at least one bond selected from the group consisting of a carbonate bond and a sulfonyl bond is preferred.
Further, as a suitable example of the water-soluble polymer compound, polyacrylic acid, polyacrylic acid salt, cellulose acetate, cellulose acetate butyrate or the like can be given.

In particular, the water-soluble compound is selected from the group consisting of ethylene carbonate, dimethyl hydrazine, cyclobutyl hydrazine, and γ-butane from the viewpoints of water disintegration and compatibility with the 2-cyanoacrylate compound. At least one compound selected from the group consisting of esters and propylene carbonate is preferred, and at least one compound selected from the group consisting of ethylene carbonate, dimethyl hydrazine, cyclobutyl hydrazine, and propylene carbonate is preferred.
Further, from the viewpoint of versatility, the water-soluble compound is preferably at least one compound selected from the group consisting of ethylene carbonate, γ-butyrolactone, dimethylhydrazine, and propylene carbonate.

The water-soluble compound used in the adhesive composition of the present invention may be used alone or in combination of two or more.
The content of the water-soluble compound is preferably 0.5% by mass or more and 50% by mass or less based on the total mass of the adhesive composition, and preferably 1% by mass or more and 40% by mass or less. 5 mass% or more and 35 mass% or less are more preferable, and 10 mass% or more and 30 mass% or less are particularly preferable.

When it is used for the adhesive composition, the 2-cyanoacrylate compound represented by the formula (1) and other components other than the water-soluble compound may be contained.
In terms of other components, an appropriate amount of an adhesive composition conventionally blended into a 2-cyanoacrylate-containing compound may be blended in an appropriate amount without impairing the hardenability and the subsequent strength of the adhesive composition. Stabilizers, hardening accelerators, plasticizers, tackifiers, particles, colorants, perfumes, solvents, strength enhancers, etc.

Examples of the stabilizer include (1) an aliphatic sulfonic acid such as sulfur dioxide or methanesulfonic acid, an aromatic sulfonic acid such as p-toluenesulfonic acid, boron trifluoride methanol or boron trifluoride diethyl ether. Free radical polymerization of compounds such as anionic polymerization inhibitors such as HBF ₄ and trialkyl borate, and (2) hydroquinone, hydroquinone monomethyl ether, tert-butylcatechol, catechol and gallic phenol Agents, etc. These stabilizers may be used alone or in combination of two or more.

Any of the hardening accelerators can be used as long as it can promote anionic polymerization of the 2-cyanoacrylate-based adhesive composition. Examples of the hardening accelerator include a polyether compound, a calixarene, a thiacalix aromatic hydrocarbon, a gallic phenol aromatic hydrocarbon, and a phosphonium salt. These hardening accelerators may be used alone or in combination of two or more.

In addition, examples of the plasticizer include ethyl triethyl citrate, tributyl ethyl citrate, dimethyl adipate, diethyl adipate, dimethyl phthalate, and phthalic acid. Dimethyl formate, diethyl phthalate, dibutyl phthalate, diisononyl phthalate, dihexyl phthalate, diheptyl phthalate, phthalic acid Dioctyl ester, bis(2-ethylhexyl) phthalate, diisononyl phthalate, diisotridecyl phthalate, dipentadecyl phthalate , dioctyl terephthalate, diisononyl isophthalate, decyl toluate, bis(2-ethylhexyl) camphorate, 2-ethylhexylcyclohexyl carboxylate, fumaric acid Isobutyl ester, diisobutyl maleate, triglyceride caproate, 2-ethylhexyl benzoate, dipropylene glycol dibenzoate, and the like. Among these, from the viewpoint of good compatibility with the 2-cyanoacrylate compound and high plasticizing efficiency, tributyl citrate, dimethyl adipate, and phthalic acid are used. Dimethyl ester, 2-ethylhexyl benzoate, and dipropylene glycol dibenzoate are preferred. These plasticizers may be used alone or in combination of two or more.

Examples of tackifiers include polymethyl methacrylate, copolymers of methyl methacrylate and acrylate, copolymers of methyl methacrylate with other methacrylates, acrylic rubber, polyvinyl acetate, and polychlorinated chloride. Ethylene, polyurethane resin, polyamide resin, polystyrene, cellulose ester, polyalkyl-2-cyanoacrylate, and ethylene-vinyl acetate copolymer. These tackifiers may be used alone or in combination of two or more.

The particles which can be blended into the adhesive composition are used to adjust the thickness of the adhesive layer when the adhesive composition is used.
The average particle diameter of the particles is preferably 10 μm to 200 μm, more preferably 15 μm to 200 μm, still more preferably 15 μm to 150 μm.
The material of the particles is not particularly limited as long as it is insoluble in the 2-cyanoacrylate compound to be used and does not cause deterioration such as polymerization. For example, polyethylene, polypropylene, polymethylpentene, acrylic resin, polyvinyl chloride, polytetrafluoroethylene, polyethylene terephthalate, polybutylene terephthalate, polyfluorene, polyphenylene Thermoplastic resin such as ether; unsaturated polyester, divinylbenzene polymer, divinylbenzene-styrene copolymer, divinylbenzene-(meth)acrylate copolymer, diallyl phthalate a crosslinked resin such as a polymer; an inorganic compound such as spherical cerium oxide, glass beads, or glass fiber; a polyfluorene oxide compound; an organic-inorganic composite particle containing an organic polymer skeleton and a polyoxyalkylene skeleton.
Further, the content of the particles is not particularly limited, and the content of the 2-cyanoacrylate compound is preferably 100 to 10 parts by mass, preferably 1 to 5 parts by mass, more preferably 1 to 3 parts by mass. Better. If it is in the range of 0.1 to 10 parts by mass, the influence on the curing rate or the subsequent strength can be reduced.
The average particle diameter of the particles in the present invention is an average value of a volume basis measured by a laser diffraction type particle size distribution measuring apparatus.

The above-mentioned adhesive composition is not particularly limited and can be used for various purposes.
In particular, in the case of being used as a water-disintegrable adhesive composition, the water-disintegrable adhesive composition may be composed of an adhesive composition which has been attached or an adhesive which is adhered to an unnecessary place and hardened. Since the material is easily peeled off or removed by water, it is suitably used as, for example, a temporarily fixed water-disintegrable adhesive composition or a teaching material water-disintegrable adhesive composition. The water disintegrable adhesive composition can of course be easily peeled off or removed in a short time by hot water or pressurized hot water, and can also be immersed in a temperature such as normal temperature (15 to 25 ° C) to warm water. Water or the like in the range of (30 to 45 ° C) is peeled off or removed. Therefore, even if it adheres to an unnecessary place such as a finger or the like and is hardened, it can be easily peeled off by water. Further, since it can be peeled off or removed by water in a temperature range from room temperature to warm water, when it is temporarily fixed for industrial use, the amount of heat necessary for peeling can be reduced, and the cost is reduced.
Here, for the temporary fixation of the industrial use, for example, various electronic materials such as a semiconductor wafer, optical materials such as lenses, and temporary fixing of various jigs such as a polishing platen can be cited.
Further, the binder to be bonded by the above-mentioned adhesive composition is not particularly limited, and may be an inorganic compound, an organic compound or an inorganic-organic composite, and may be the same material or a different material. Further, the above-mentioned adhesive composition can be followed by an object of any shape in a solid state.

Further, the method for storing the 2-cyanoacrylate compound represented by the formula (1) and the above-mentioned adhesive composition is not particularly limited, and may be stored by using a well-known cyanoacrylate storage method. Suitable examples include storage under an anhydrous inert gas, storage in a light-shielding sealed container, and the like.
[Examples]

Hereinafter, the present invention will be specifically described based on examples. Further, the invention is not limited by the embodiments. In addition, the following "parts" and "%" mean "mass parts" and "% by mass" unless otherwise specified.

(Example 1: Synthesis of a compound represented by the above formula (2) (glycerol carbonate-2-cyanoacrylate))
Ethyl-2-cyanoacrylate (125 g, 1 mol) was dissolved in toluene (200 mL) and cooled in an ice bath. The internal temperature was maintained at 25 ° C or lower while cyclopentadiene (70.1 g, 1.06 mol) was added thereto. After further stirring to room temperature for 1 hour, toluene and excess cyclopentadiene were distilled off under reduced pressure. The mixture was distilled under reduced pressure (87 ° C, 30 Pa) to afford ethyl (ethyl ether) (ethyl ether) (yield: 94%).
In a solution of ethyl-2-cyanoacrylate/cyclopentadiene adduct (191 g, 1 mol) in toluene (200 mL), it took 1 hour to add potassium hydroxide (84.2 g, 1.5 mol) dissolved in distilled water. An aqueous solution (500 mL) was stirred at 60 ° C for 1 hour. 35% hydrochloric acid (314 g, 3.0 mol) was added to bring the pH to 1, and the mixture was transferred to a separating funnel, the aqueous layer was separated, and the toluene layer was washed with water. The toluene was distilled off under reduced pressure to give 124 g (yield: 76%) of 2-cyanoacrylic acid/cyclopentadiene adduct.
Addition of 2-cyanoacrylic acid/cyclopentadiene adduct (163 g, 1 mol), glycerol carbonate (130 g, 1.1 mol), p-toluenesulfonic acid hydrate (9.5 g, 0.05 mol) to toluene (1 L) In the middle, the generated water is separated while heating and refluxing. At 8 hours, the amount of dehydration reached 80% (15.3 mL) of the theoretical amount. Once the reaction solution was returned to room temperature, the solid precipitated. The precipitated solid was filtered, washed with toluene, and the obtained solid was recrystallized from methanol to give glycerol carbonate-2-cyanoacrylate/cyclopentadiene adduct 79 g (yield 30). %).
The glycerol carbonate-2-cyanoacrylate/cyclopentadiene adduct (26.3 g, 0.1 mol) was thermally decomposed under a pressure of 100 Pa or less and at 150 ° C to obtain glycerol carbonate-2- Cyanoacrylate 19.0 g (yield 96%).

The ¹ H and ¹³ C-NMR spectra of the obtained compound of the formula (2) are as follows.
¹ H-NMR (CD ₃ CN): δ=7.05 (s, 1H), 6.82 (s, 1H), 5.06-5.01 (m, 1H), 4.60-4.32 (m, 4H)
¹³ C-NMR (CD ₃ CN): δ = 161.2, 155.8, 145.9, 116.4, 115.3, 74.8, 66.9, 66.1
[Industrial availability]

The 2-cyanoacrylate compound of the present invention is suitably used as a hardening component of the adhesive composition. For example, it can be used in general households, teaching materials, building materials, medical fields, and the like as a so-called instant adhesive, and can be used in various products and technical fields such as various industries.
Further, the adhesive composition containing the 2-cyanoacrylate compound of the present invention is not only suitable for use between the same kinds of the materials to be bonded, but is particularly suitable for use in the subsequent connection between the different kinds of the materials (for example, between metal and resin).
Further, the adhesive composition containing the 2-cyanoacrylate compound of the present invention is excellent in adhesion to a polarized member after curing.

Claims (8)

A 2-cyanoacrylate compound which is represented by the following formula (1): [Chemical Formula 1] In the formula (1), L ¹ represents a divalent linking group having 1 to 20 carbon atoms, and R ¹ to R ³ each independently represent a hydrogen atom, a halogen atom, an alkyl group or an aromatic group, and two of R ¹ to R ³ . The above may also be bonded to form a ring structure. The 2-cyanoacrylate compound according to claim 1, wherein the L ¹ is an alkylene group having 1 to 20 carbon atoms, or a combination of two or more alkylene groups and is selected from the group consisting of an ether bond and an ester bond. The divalent group having 1 to 20 carbon atoms formed by one or more structures. The 2-cyanoacrylate compound according to claim 1, wherein L ¹ is an alkylene group having 1 to 20 carbon atoms. The 2-cyanoacrylate compound according to claim 1, wherein each of R ¹ to R ^{3 is} independently a hydrogen atom or an alkyl group. The 2-cyanoacrylate compound according to claim 1, wherein R ¹ to R ³ are a hydrogen atom. The 2-cyanoacrylate compound according to claim 1, wherein the 2-cyanoacrylate compound represented by the above formula (1) is a 2-cyanoacrylate compound represented by the following formula (2): [Chemical Formula 2] . An adhesive composition comprising the 2-cyanoacrylate compound according to any one of claims 1 to 6. The adhesive composition of claim 7, which is a water-disintegrable adhesive composition.