KR100377243B1 - Adhesive composition, tape and label easily peeled off after an extended time period - Google Patents

Abstract

The present invention provides an easily peelable pressure-sensitive adhesive composition prepared by adding a low molecular weight functionalized organopolysiloxane and / or a curing agent to an existing adhesive resin, an adhesive tape and a label using the same. The adhesive tape or label according to the present invention can be easily peeled off without contaminating or damaging the surface of the adherend even after prolonged use, since the adhesive tape or label does not damage the initial adhesive force and the adhesive force, and has no effect of increasing the adhesive force over time.

Description

Easy Release Adhesive, Tape and Label {ADHESIVE COMPOSITION, TAPE AND LABEL EASILY PEELED OFF AFTER AN EXTENDED TIME PERIOD}

The present invention relates to a peelable pressure-sensitive adhesive composition composed of a tacky resin, a low molecular weight functional organopolysiloxane, and an optional curing agent, which do not change the adhesion even during long term adhesion. More specifically, the present invention provides (1) 0.5 to 10 parts by weight of a low molecular weight functionalized organopolysiloxane having a molecular weight of 300 to 50,000, (2) natural rubber, butyl rubber, acrylic resin, urethane resin or silicone The present invention relates to a peelable pressure-sensitive adhesive composition composed of 100 parts by weight of an adhesive resin having a molecular weight of 50,000 to 2,000,000, and optionally (3) a curing agent, having excellent initial adhesive strength and adhesive strength, and having no increase in adhesive strength over time. It is easy to re-peel even after attachment and does not cause surface damage and contamination.

Adhesive tapes or adhesive labels are widely used for industrial, medical, office, and home use. The adhesive tape or label is in the form of a tape coated with adhesive on one or both sides of a support such as paper, fabric, plastic film, etc., and can be adhered only by applying a slight pressure at room temperature without using a solvent or heat. It is a tape that can be used, and has cohesiveness and elasticity, and that can be strongly adhered while being peeled off a hard smooth surface. The adhesive used for the adhesive tape or adhesive label should have excellent initial adhesive force, adhesive force and cohesion and a good balance between them, and should not cause surface damage and contamination of the adherend when peeled for removal after prolonged adhesion. .

The adhesive and the adhesive tape using the same are also referred to as pressure-sensitive adhesives and pressure-sensitive adhesive tapes because they are attached by pressure.

Existing pressure-sensitive adhesives used for pressure-sensitive adhesive tapes or adhesive labels are composed of pressure-sensitive adhesives, tackifiers, plasticizers and optionally adhesive aids (crosslinkers, stabilizers, anti-aging agents, etc.), and the pressure-sensitive adhesive resins may be thermoplastic rubbers, Butyl rubber, acrylic resin, urethane rubber, silicone rubber and the like are used, but their physical properties and performance are different. These adhesives are used in a variety of adhesive tapes or labels, as well as in the adhesion and adhesion of shoes, leather, ceramics, glass, construction, electronics, wallpaper, furniture, wood, packaging, paper, plastics and the like.

The adhesive adhered to the adherend generates adhesive strength due to the wetting phenomenon on the surface of the adherend, and as time passes, the physical adhesive surface of the adhesive resin and the adherend surface is increased, thereby improving the adhesive force. Heat) or the like deteriorates the cohesion force of the pressure-sensitive adhesive or the like, and the elastic force is reduced or lost.

Over time, the increase in adhesive strength and / or decrease in elasticity, which are found in conventional adhesives, makes it difficult to separate the bond between the adhesive layer and the adherend when the adhesive tape is peeled off for removal after being adhered to the adherend surface for a long time. It tends to lower the agglomeration of, which causes damage to the surface of the adherend or does not completely remove the pressure-sensitive adhesive layer from the surface of the adherend, leading to contamination of the adherend surface.

Specifically, in the case of the surface protection tape, which is a kind of industrial adhesive tape, it should be removed after the protection function of the product is completed after being attached to the adherend, and should not cause damage or contamination of the adherend surface. Office adhesive tape should also have good adhesiveness in the beginning, and when removed, it should be able to be clean and easily used on paper, which is generally used as an adhesive. In the case where the adherend is a paper adherend, if the adhesive force is too high, surface damage of the adherend occurs, and if the adhesive remains on the surface of the adherend and there is surface contamination, an organic solvent or the like cannot be used to remove it. Therefore, there is a great need for a pressure-sensitive adhesive having excellent initial adhesive strength and a lasting adhesive force but which does not increase over time so as not to cause surface damage or contamination upon removal.

Even in the case of medical adhesives, since the organic solvent cannot be used to remove the adhesive tape residues as well as the part directly touching the skin, the adhesive or the adhesive tapes used must be able to be removed.

Similarly, the most commonly used labels often need to be replaced with new ones as needed, so that the initial adhesion must be high so that they do not easily detach after adhesion, and they can be easily replaced with new labels without any surface damage or contamination. Should be able to be removed.

Therefore, for industrial, home, office, medical adhesive tapes or labels, it has excellent initial adhesive strength and high adhesive strength durability, and does not cause surface damage or contamination during removal or peeling, and does not change adhesive strength even after long-term attachment, and thus can be easily removed. There is a demand for an easily peelable or easy release adhesive.

USP 5,100,976 describes polydiorganosiloxanes represented by the formula R ¹ R ₂ SiO (R ₂ SiO) _n SiR ₂ R ¹ (wherein R is a monovalent hydrocarbon and R 1 is a monovalent hydrocarbon or hydroxy) and a multicomponent R _A silicone-based pressure-sensitive adhesive (PSA) with improved desorption and adhesion, consisting of a small amount of organopolysiloxane having ₃ SiO _1/2 units and a minor component (R ² O) _a SiO _{(4-a) / 2} units -sensitive adhesive).

USP 5,580,915 discloses pressure sensitive adhesive compositions consisting of silanol-containing siloxane resins, silicone polymer gums, and reaction mixtures of silicone fluids having functional groups capable of reacting with silanol groups. The silicone pressure sensitive adhesive composition has excellent quick adhesion, peelability and detachment / adhesion.

USP 5,907,018 discloses silicone pressure sensitive adhesives (PSAs) comprising organopolysiloxanes having terminal amino groups.

The above patents all relate to silicone pressure-sensitive adhesives, and silicone resins have low surface energy and excellent viscosity retention, and thus exhibit excellent adhesion even upon reattachment without showing surface damage or contamination of the adherend upon removal. It has been used a lot as an easily peelable pressure-sensitive adhesive or a pressure-sensitive adhesive for a long time.

However, the silicone pressure sensitive adhesive has a disadvantage in that the initial adhesive strength is poor because wetness or dispersibility on the surface of the adherend is poor due to its low surface energy. Above all, the above-mentioned documents do not mention the ease of peeling after long-term use, that is, the increase in adhesion over time and the change in elastic force and the difficulty of peeling due to this.

While the present inventors have studied a pressure-sensitive adhesive that can be easily removed even after long-term use without surface damage or contamination, when the specific organopolysiloxane is mixed with the existing pressure-sensitive adhesive resin, the initial adhesion and the pressure-sensitive adhesive strength of the existing pressure-sensitive adhesive resin are substantially maintained. The present invention was completed by discovering that the increase in adhesive force and elasticity change are prevented even after prolonged adhesion, and thus do not cause damage or contamination of the adherend surface upon removal even after prolonged adhesion.

An object of the present invention is to provide a peelable pressure-sensitive adhesive composition comprising a low molecular weight functionalized organopolysiloxane and an adhesive.

Another object of the present invention is (1) 0.5 to 10 parts by weight of a low molecular weight functionalized organopolysiloxane having a molecular weight of 300 to 50,000, (2) natural rubber, butyl rubber, acrylic resin, urethane resin or silicone resin It is to provide 100 parts by weight of an adhesive resin having a molecular weight of 50,000 to 2,000,000 selected from the above, and optionally (3) a peelable pressure-sensitive adhesive composition composed of a curing agent.

Hereinafter, the present invention will be described in more detail, and the molecular weight of orgonopolysiloxane means weight average molecular weight unless otherwise indicated.

Adhesion (tacky adhesion) means that the fluid material is in contact with the adherend, which requires a means of dissolution heating to make it fluid when contacting the adherend, but the viscosity itself Has the original liquid properties. When trying to peel off the adhesive after sticking, it shows viscoelastic resistance against external force.

Therefore, the pressure-sensitive adhesive should be excellent in adhesion (adhesion, adhesion), initial adhesion (tack) and cohesion (cohesion), and in order to fall off cleanly attached to the adherend not only has to be excellent cohesion but also the balance of the three physical properties It must be done. In addition, if there is a need for later removal, its adhesion should not increase to such an extent that surface damage or contamination may occur even after prolonged adhesion.

In general, the adhesive is generated by the wetting phenomenon on the surface of the adhesive, the physical adhesive surface between the adhesive resin and the surface of the adhesive increases with time, the adhesion is further improved and the external environment (light, heat), etc. As a result, the cohesive force and the like of the pressure-sensitive adhesive deteriorate, and the elastic force decreases or is lost. In addition, when the surface energy of the adhesive is low, such wet phenomenon does not occur well, and thus the initial adhesive strength is low, and when the surface energy is high, the wet phenomenon occurs well, but the cohesive force decreases, and thus it is likely to remain on the surface of the adherend. .

Silicone rubber has low surface energy and excellent cohesive force (i.e., viscous holding force), so it shows excellent adhesion even after reattachment without showing surface damage or contamination of the adherend upon removal. It has been used a lot as an adhesive. However, the low surface energy of the silicone rubber not only prevents the wetness with the adherend, thereby making the initial adhesive force poor, but also the poor compatibility with other adhesive resins, resulting in phase separation when mixed with other resins. Therefore, it shows little effect of the mixed use.

Due to the characteristics of such silicone resins, silicone resins are not well used for pressure-sensitive adhesives other than silicone-based pressure-sensitive adhesives, and it has been disclosed to solve the problem of miscibility in the form of silicone-containing resins. For example, US Pat. No. 5,556,636 discloses a medical adhesive composition comprising an oxyalkylene polymer having a silicone-containing group and a viscous resin, but does not substantially solve the above-mentioned problems.

In order to solve the shortcomings of the existing pressure-sensitive adhesive, the present inventors can increase cohesiveness without impairing adhesion and initial adhesion, and also as an additive capable of adjusting and improving the balance of the three physical properties described above. Organopolysiloxanes are used.

The low molecular weight functionalized organopolysiloxane used in the present invention is different from the high molecular weight silicone rubber used as the adhesive resin, and generally has a molecular weight of 300 to 50,000, preferably a molecular weight of 400 to 30,000, more Preferably it has a molecular weight of 500 to 10,000.

In the present invention, the functionalized group of the functionalized organopolysiloxane is for increasing the binding with the pressure sensitive adhesive resin, and is bonded with the pressure sensitive adhesive resin by condensation and / or addition reaction. Although the functional group which can be used is not specifically limited, For example, a hydroxyl group, an alkoxy group, an amino group, an alkenyl group, an alkynyl group, etc. are mentioned.

Since such functionalized organopolysiloxane is dissolved in a solvent and used, it may have any properties such as liquid, powder, paste, and solid phase, but a liquid phase is preferable, and it is generally 1 to 10,000 cps, preferably 10 Have a viscosity of ˜5,000 cps.

As one embodiment of the low molecular weight functionalized or unorganized organopolysiloxane used in the present invention, R ₃ SiO _1/2 units (wherein R hydroxy groups, alkoxy groups having 1 to 20 carbon atoms or 1 to 20 carbon atoms) And (R ² O) _a SiO _{(4-a) / 2} (wherein R ² hydroxy group, alkoxy group having 1 to 20 carbon atoms or hydrocarbon group having 1 to 20 carbon atoms, and a is 1 or 2 Organopolysiloxanes), but is not particularly limited thereto.

As one embodiment of the low molecular weight functionalized organopolysiloxane used in the present invention, organopolysiloxanes used as surface treatment agents such as coupling agents can be used. More particularly, organopolysiloxanes having a molecular weight of 500 to 10,000 and having hydroxyl groups at both ends of the molecule are most suitable.

In the present invention, the amount of the low molecular weight functionalized organopolysiloxane is used in an amount of 0.5 to 10 parts by weight, preferably 1 to 7 parts by weight, per 100 parts by weight of the pressure-sensitive adhesive resin. If the amount is 0.5 parts by weight or less, the effect of adding organopolysiloxane is not well exhibited. If it is 10 parts by weight or more, the cohesive force is excellent, but the initial adhesiveness tends to be lowered. In the present invention, the addition amount of organopolysiloxane can be easily adjusted by those skilled in the art according to the type of adhesive, adhesive force, initial adhesive force, adherend surface component, surface roughness, and degree of contamination of adherend surface.

The pressure-sensitive adhesive used in the present invention is composed of a resin selected from existing adhesive resins, for example, natural rubber, butyl rubber, acrylic resin, urethane resin, silicone resin.

There is no particular limitation on the kind of the adhesive resin that can be used in the present invention, and most of the currently used adhesive resins can be used. The adhesive resin usable in the present invention generally has a molecular weight of 50,000 to 2,000,000, preferably a molecular weight of 100,000 to 1,500,000. When the molecular weight of the pressure-sensitive adhesive resin is 50,000 or less, the cohesive force of the pressure-sensitive adhesive decreases, so that a phenomenon in which a part of the pressure-sensitive adhesive layer remains on the surface of the adherend may occur when it is attached to the adherend and then removed. When the molecular weight of the adhesive resin is 2,000,000 or more, since the cohesive force of the adhesive resin is very large, it can be easily removed even after long-term adhesion to the adherend. However, since the wet phenomenon on the adherend surface is very low, the initial adhesive force is lowered. Therefore, when organopolysiloxane which lowers surface energy is added, initial stage adhesive force falls further, and it loses the function as an adhesive.

In the easy-release peelable pressure-sensitive adhesive composition of the present invention, the added organopolysiloxane prevents the increase of the adhesive strength over time, and lowers the surface energy of the pressure-sensitive adhesive layer to help the pressure-sensitive adhesive evenly distributed on the surface of the adherend. Dispersion of the pressure-sensitive adhesive evenly on the surface of the adherend means the same as the excellent wet phenomenon of the surface of the adherend, thereby improving the initial adhesive strength of the pressure-sensitive adhesive.

In the present invention, the organopolysiloxane and the pressure-sensitive adhesive may be chemically bonded to a pressure-sensitive adhesive composition composed of a low molecular weight functionalized organopolysiloxane and pressure-sensitive adhesive.

It is therefore a further object of the present invention to provide a pressure sensitive adhesive composition composed of a low molecular weight functionalized organopolysiloxane, an adhesive resin and a curing agent or catalyst.

As described above, the silicone resin has a low surface energy and thus may have low compatibility with other adhesive resins. When organopolysiloxane is added to other adhesives, the organopolysiloxane is transferred from the adhesive layer to the adherend surface and deposited. This may cause fine contamination. Therefore, when the organopolysiloxane is difficult or miscible with the pressure-sensitive adhesive resin, the organopolysiloxane may be chemically combined with the pressure-sensitive resin by adding a curing agent and / or a curing catalyst together.

The added curing agent not only improves the bonding between the organopolysiloxane and the adhesive resin, but also prevents the increase of the chemical bonding force between the adhesive layer and the adherend surface and serves to maintain the elasticity of the adhesive resin for a long time.

The curing agent is not particularly limited, and compounds or mixtures commonly used as curing agents in the art may be used. In this invention, a hardening | curing agent is suitably selected according to the kind of adhesive resin used. For example, difunctional or diisocyanate compounds such as dicarboxylic acid or diisocyanate can be used. The type and amount of such curing agents can be readily selected by those skilled in the art within the scope of not impairing the properties of the composition of the present invention, and generally 0.1 to the organopolysiloxane used. To 20% by weight.

When the curing agent is used in the present invention, a curing catalyst may be additionally used, and the type and amount of the curing catalyst are used in the range of not impairing the properties of the composition of the present invention. And amounts appropriately selected by those skilled in the art. For example, when an isocyanate compound is used as the curing agent, an organotin compound is generally used as the curing catalyst, and preferably dibutyltin diacetate or dibutyltin dilaurate may be mentioned. In the present invention, such a curing catalyst is not essential.

Moreover, when it is necessary to adjust the characteristic of an adhesive composition once again, or to accelerate hardening, methylhydrosiloxane can be added in the quantity of 0.1-10 weight% (solid content basis) with respect to organopolysiloxane.

The adhesive composition prepared according to the present invention has a polarity for maintaining a constant adhesive strength to the adherend, but because the surface energy of the adhesive is not high, it adheres well to the surface of the adherend so that the initial adhesive strength is high, and the adhesive force increases with time. Since this does not occur, it does not cause surface damage or contamination even after peeling after long-term use.

The pressure-sensitive adhesive composition prepared according to the present invention may be prepared as a pressure-sensitive adhesive tape or label for industrial, household, medical, office and surface protection by applying it on one or both sides of the support according to a method known in part or in whole.

The pressure-sensitive adhesive composition prepared according to the present invention may add additives commonly used in the pressure-sensitive adhesive field, such as tackifiers, crosslinking agents, stabilizers, antioxidants, or any active ingredients. The use type and the usage amount thereof can be appropriately determined by those skilled in the art within the range not impairing the properties of the pressure-sensitive adhesive composition of the present invention.

Example

The present invention is explained in more detail below. Parts and percentages are by weight unless otherwise indicated, and molecular weight means weight average molecular weight. The meanings of the abbreviations used in the present invention are as follows.

AN acrylonitrile

BA Butyl Acrylate

EA ethyl acrylate

2-EHA ethylhexyl acrylate

2-HEMA 2-hexylethyl methacrylate

MMA Methyl Methacrylate

Example 1

The adhesive is prepared by mixing the following. Hereinafter, the pressure-sensitive adhesive A is called.

- 100 parts of suspension polymerized acrylic pressure-sensitive adhesive to the BA / EA / AN,

, A tackifier, 10 parts [polyterpene phenol resin],

, Organopolysiloxane, 5 parts [trade name: SH2311, GOLDSCHMIDT A GROUP COMPANY manufactured,

Organo tin, 0.5 parts [trade name DABCO T-12 CATALYST, AIR PRODUCTS manufactured,

Isocyanate, 5 parts [trade name: CA-75, Songwon manufactured as a curing agent, and

700 parts of toluene, as a solvent.

Example 2

The adhesive is prepared by mixing the following. Hereinafter, it is called adhesive B.

· MMA / 2-HEMA / 2 -EHA / BA solution of 100 parts of polymerized acrylic pressure-sensitive adhesive in,

· Organopolysiloxane 3 parts [trade name: SH2311, GOLDSCHMIDT A GROUP COMPANY manufactured,

Organo tin, 0.5 parts [trade name DABCO T-12 CATALYST, AIR PRODUCTS manufactured and

Isocyanate, 5 parts [trade name: CA-75, Songwon manufactured as a curing agent, and

· 800 parts of toluene as solvent.

Example 3

The adhesive is prepared by mixing the following. Hereinafter, it is referred to as pressure-sensitive adhesive C.

- butyl rubber 100 parts [trade name: MML-100, EXXON manufactured,

, Polybutene rubber, 100 parts [trade name: PB-1400, Daelim Industrial Manufacturing Co.],

, A tackifier, 10 parts [polyterpene phenol resin],

, Organopolysiloxane, 5 parts [trade name: SH2311, GOLDSCHMIDT A GROUP COMPANY manufactured,

Organo tin, 0.5 parts [trade name DABCO T-12 CATALYST, AIR PRODUCTS manufactured, and

Isocyanate, curing agent [trade name: CA-75, Songwon manufactured as 5 parts, and

900 parts of toluene, as a solvent.

Comparative Example 1

The adhesive is prepared by mixing the following. Hereinafter, it is referred to as pressure-sensitive adhesive D.

- 100 parts of suspension polymerized acrylic pressure-sensitive adhesive as BA / EA / AN,

, A tackifier, 10 parts [polyterpene phenol resin],

Isocyanate, 5 parts [trade name: CA-75, Songwon manufactured as a curing agent, and

700 parts of toluene, as a solvent.

Comparative Example 2

The adhesive is prepared by mixing the following. Hereinafter, the pressure-sensitive adhesive E is called.

· MMA / 2-HEMA / 2 -EHA / BA solution of 100 parts of polymerized acrylic pressure-sensitive adhesive in,

Isocyanate, 5 parts [trade name: CA-75, Songwon manufactured as a curing agent, and

800 parts of toluene, as a solvent.

Comparative Example 3

The adhesive is prepared by mixing the following. Hereinafter, the pressure-sensitive adhesive F is called.

- butyl rubber 100 parts [trade name: MML-100, EXXON manufactured,

, Polybutene rubber, 100 parts [trade name: PB-1400, Daelim Industrial Manufacturing Co.],

, A tackifier, 10 parts [polyterpene phenol resin],

900 parts of toluene, as a solvent.

Test Example

In order to test each of the prepared adhesives, a sample was prepared as follows: 0.1 mm thick PE film support (width 25 mm, length 300 mm) on one side of which was discharged on the basis of the solid content. After apply | coating in the quantity of 10 g / mm <2>, it drys at 80 degreeC for 5 minutes. Then, it is aged for 24 hours at 50 ℃ to crosslink the pressure-sensitive adhesive to obtain a test piece.

1) Adhesion test

Each sample prepared above is attached on a 304BA stainless steel plate and the force required to peel off at a constant rate of 300 mm / min at a 90 ° angle is measured (see Korean Industrial Standard A 1104). The results are shown in Table 1 below.

2) Test of adhesive force change over time

Prepare 7 test pieces for each pressure-sensitive adhesive in the same manner as prepared in the above adhesive test. Thus prepared test pieces after adhesion 1 day 5 days 15 days 30 days 60 days 90 days 120 days after the measurement of the adhesive strength by the above test method. The results are shown in Table 1 below.

3) Adhesive surface contamination test.

After the adhesive tape test piece prepared above is prepared to a width of 150mm and a length of 300mm, it is attached to a 304BA steel plate having a width of 150mm and a length of 300mm. The attached test piece is visually inspected for contamination such as adhesive transfer on the surface of the adherend while peeling off the adhesive tape after 200 hours of testing in a weather resistance measuring instrument. The results are shown in Table 1 below.

Changes in adhesion over time and effects at peeling Example Adhesive force change (gf / 25mm) Surface contamination Peel Test 1 day 5 days 15th 30 days 60 days 90 days 120 days Example 1 150 150 160 170 170 170 180 none Good Example 2 200 200 220 230 230 240 250 none Good Example 3 180 180 180 190 190 200 200 none Good Comparative Example 1 180 250 350 400 450 500 500 none difficulty Comparative Example 2 240 370 420 520 580 580 580 none difficulty Comparative Example 3 240 340 400 500 550 550 550 none difficulty

Table 1 is a result of measuring the adhesive strength with respect to the pressure-sensitive adhesive and the conventional pressure-sensitive adhesive according to the present invention over time. From Table 1, it can be seen that the novel easy-release peelable pressure-sensitive adhesive of the present invention is a very small pressure-sensitive adhesive changes in the initial and final adhesive strength. Therefore, even when the adhesive is attached to the paper, even when peeling after a long time does not cause damage such as tearing or peeling of the paper surface.

Therefore, applying this new adhesive to labels, medical adhesive tapes, office adhesive tapes, and surface protective adhesive tapes, it is possible to produce adhesive tapes that are very easy to attach and peel without damaging the initial adhesive strength and adhesive strength. In addition, using the pressure-sensitive adhesive composition according to the present invention, it is possible to maintain the surface state of the initial stage of adhesion without contamination or damage to the surface of the adherend after peeling.

According to the present invention, by adding a low molecular weight functionalized organopolysiloxane and an optional curing agent and curing catalyst to the existing adhesive, it is possible to easily peel off even after prolonged adhesion to the adherend, thereby causing damage to the surface of the adherend and contamination. There is no

Claims (14)

(1) 0.5 to 10 parts by weight of organopolysiloxane having a weight average molecular weight of 300 to 50,000 and functionalized with a hydroxyl group, alkoxy group, amino group, alkenyl group or alkynyl group, (2) natural rubber, butyl rubber, acrylic resin , 100 parts by weight of an adhesive resin having a molecular weight of 50,000 to 2,000,000 selected from a urethane resin or a silicone resin, and (3) an easily releasing adhesive composition comprising 0 to 30% by weight of a curing agent based on the organopolysiloxane described above. The composition of claim 1, wherein the low molecular weight functionalized organopolysiloxane described above has a weight average molecular weight of 400 to 30,000. The composition of claim 1 or 2, wherein the low molecular weight functionalized organopolysiloxane described above is an organopolysiloxane used as a surface treatment agent such as a coupling agent. The composition according to claim 1 or 2, wherein the low molecular weight functionalized organopolysiloxane described above is functionalized with a hydroxyl group. The composition of claim 1 or 2, wherein the low molecular weight functionalized organopolysiloxane described above has a molecular weight of 500 to 10,000 and has hydroxyl groups at both ends of the molecule. The composition according to claim 1 or 2, wherein the amount of the low molecular weight functionalized organopolysiloxane described above is 1 to 10 parts by weight per 100 parts by weight of the adhesive resin. The composition according to claim 1 or 2, wherein the above-mentioned adhesive resin is butyl rubber or acrylic resin. The composition according to claim 1 or 2, wherein the above-mentioned adhesive resin has a molecular weight of 100,000 to 1,500,000. The composition of claim 1 or 2, wherein the curing agent described above is an isocyanate compound or a mixture of isocyanates and organotin. 10. The composition of claim 9, wherein the curing agent described above is used in an amount of 0.1 to 20% by weight relative to the organopolysiloxane. The composition according to claim 1 or 2, wherein the methylhydrosiloxane is contained in an amount of 0.1 to 10% by weight (based on solids) relative to the organopolysiloxane. A pressure-sensitive adhesive tape prepared by applying the pressure-sensitive adhesive composition according to claim 1 partially or entirely on one or both sides of a support. A label prepared by applying the pressure-sensitive adhesive composition according to claim 1 partially or entirely on one or both sides of the support. (1) 0.5 to 10 parts by weight of organopolysiloxane having a weight average molecular weight of 300 to 50,000 and functionalized with a hydroxyl group, an alkoxy group, an amino group, an alkenyl group or an alkynyl group, (2) natural rubber, butyl rubber, acrylic resin , 100 parts by weight of an adhesive resin having a molecular weight of 50,000 to 2,000,000 selected from urethane resins or silicone resins, and (3) 0 to 30% by weight of a curing agent based on the organopolysiloxane. Manufacturing method.