COMPOUND, METHOD FOR PRODUCING COMPOUND, ADHESIVE COMPOSITION AND ADHESIVE TAPE

Abstract

The present invention aims to provide a compound capable of increasing the adhesion strength of adhesive compositions, particularly, even to low polarity adherends. The present invention also aims to provide a method for producing the compound, an adhesive composition containing the compound, and an adhesive tape including an adhesive layer containing the adhesive composition. Provided is a compound including at least one structural unit (A) selected from the group consisting of a structural unit (A-1) and a structural unit (A-1′) that are represented by the following formulas:

##STR00001##

wherein each R.sup.1 represents a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a polar functional group, an aliphatic hydrocarbon group containing a polar functional group, or an aromatic hydrocarbon group containing a polar functional group; n represents an integer of 2 or greater and 4 or less; and n′ represents an integer of 2 or greater and 5 or less.

Claims

1. A compound comprising at least one structural unit (A) selected from the group consisting of a structural unit (A-1) and a structural unit (A-1′) that are represented by the following formulas: ##STR00008## wherein each R.sup.1 represents a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a polar functional group, an aliphatic hydrocarbon group containing a polar functional group, or an aromatic hydrocarbon group containing a polar functional group; n represents an integer of 2 or greater and 4 or less; and n′ represents an integer of 2 or greater and 5 or less.

2. The compound according to claim 1, having a Young’s modulus at 25° C. of 10 MPa or greater.

3. The compound according to claim 1, further comprising an aliphatic hydrocarbon group containing an unsaturated double bond.

4. The compound according to claim 1, further comprising a structural unit (B) derived from at least one monomer (b) selected from the group consisting of a terpene monomer, a vinyl monomer, and a conjugated diene monomer.

5. The compound according to claim 1, having a structural unit (A) content of 1 mol% or greater and 60 mol% or less.

6. The compound according to claim 1, having a weight average molecular weight of 400 or greater and 10,000 or less.

7. The compound according to claim 1, having a glass transition temperature of 0° C. or higher and 200° C. or lower.

8. The compound according to claim 1, wherein a bio-derived carbon content in carbon in the compound is 10% or greater.

9. The compound according to claim 1, wherein n and n′ in the structural unit (A) are 2.

10. The compound according to claim 1, wherein n and n′ in the structural unit (A) are 3.

11. The compound according to claim 1, wherein the structural unit (A) is in a backbone structure or at a terminal of the backbone structure.

12. A method for producing a compound including at least one structural unit (A) selected from the group consisting of a structural unit (A-1) and a structural unit (A-1′) that are represented by the following formulas and a structural unit (B) derived from at least one monomer (b) selected from the group consisting of a terpene monomer, a vinyl monomer, and a conjugated diene monomer, the method comprising copolymerizing a monomer (a) represented by the following formula and the monomer (b): ##STR00009## ##STR00010## wherein each R.sup.1 represents a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a polar functional group, an aliphatic hydrocarbon group containing a polar functional group, or an aromatic hydrocarbon group containing a polar functional group; n represents an integer of 2 or greater and 4 or less; n′ represents an integer of 2 or greater and 5 or less; and n″ represents an integer of 2 or greater and 5 or less.

13. The method for producing a compound according to claim 12, wherein the monomer (a) and the monomer (b) are copolymerized by cationic polymerization.

14. An adhesive composition comprising: a base polymer; and the compound (T1) according to claim 1.

15. The adhesive composition according to claim 14, wherein the compound (T1) is contained in an amount of 1 part by weight or greater and 35 parts by weight or less relative to 100 parts by weight of the base polymer.

16. The adhesive composition according to claim 14, further comprising at least one tackifier resin (T2) selected from the group consisting of a rosin ester resin, a terpene resin, and a petroleum resin.

17. The adhesive composition according to claim 16, wherein the tackifier resin (T2) is contained in an amount of 10 parts by weight or greater and 100 parts by weight or less relative to 100 parts by weight of the base polymer.

18. The adhesive composition according to claim 17, wherein the tackifier resin (T2) is contained in an amount of 10 parts by weight or greater and 50 parts by weight or less relative to 100 parts by weight of the base polymer.

19. The adhesive composition according to claim 14, wherein the base polymer is an acrylic polymer.

20. The adhesive composition according to claim 19, wherein the acrylic polymer includes a structural unit derived from a monomer containing a crosslinkable functional group.

21. The adhesive composition according to claim 20, wherein the structural unit derived from a monomer containing a crosslinkable functional group is contained in an amount of 0.01% by weight or greater and 20% by weight or less in the acrylic polymer.

22. The adhesive composition according to claim 19, wherein the acrylic polymer has a weight average molecular weight of 200,000 or greater and 2,000,000 or less.

23. The adhesive composition according to claim 14, wherein the base polymer is a styrene elastomer that is a block copolymer including a block derived from a styrene monomer and a block derived from a conjugated diene monomer or a hydrogenated product of the block copolymer.

24. The adhesive composition according to claim 23, wherein the styrene elastomer is a styrene-isoprene-styrene (SIS) block copolymer or a styrene-butadiene-styrene (SBS) block copolymer.

25. The adhesive composition according to claim 23, wherein the styrene elastomer has a diblock proportion of 50% by weight or greater.

26. The adhesive composition according to claim 23, wherein the styrene elastomer has a styrene content of 20% by weight or less.

27. An adhesive tape comprising an adhesive layer containing the adhesive composition according to claim 14.

28. An adhesive tape comprising an adhesive layer containing the adhesive composition according to claim 19, the adhesive layer having a gel fraction of 10% by weight or greater and 70% by weight or less.

29. The adhesive tape according to claim 28, wherein the adhesive layer has a shear storage modulus at 25° C. of 1.0 × 10.sup.4 Pa or greater and 5.0 × 10.sup.5 Pa or less as measured using a dynamic viscoelastometer at a measurement frequency of 10 Hz.

30. The adhesive tape according to claim 28, wherein a loss tangent of the adhesive layer has a peak at a temperature of -20° C. or higher and 20° C. or lower as measured using a dynamic viscoelastometer at a measurement frequency of 10 Hz.

31. The adhesive tape according to claim 27, used for fixing an electronic device component or an in-vehicle component.

Description

DESCRIPTION OF EMBODIMENTS

[0132] The embodiments of the present invention are more specifically described in the following with reference to examples. These examples are not intended to limit the present invention.

Synthesis Example 1

Preparation of Acrylic Polymer

[0133] A reactor equipped with a thermometer, a stirrer, and a condenser was charged with 100 parts by weight of ethyl acetate, purged with nitrogen, and then heated to start reflux. Thirty minutes after the ethyl acetate came to a boil, 0.08 parts by weight of azobisisobutyronitrile as a polymerization initiator was added. The monomer mixture shown in Table 1 was then uniformly and gradually dropped over 1.5 hours for reaction. Thirty minutes after the termination of dropping, 0.1 parts by weight of azobisisobutyronitrile was added to continue the polymerization reaction for an additional 5 hours. The contents of the reactor were then cooled while being diluted by adding ethyl acetate into the reactor, whereby an acrylic polymer solution having a solid content of 25% by weight was obtained.

[0134] The obtained acrylic polymer solution was filtered through a filter (material: polytetrafluoroethylene, pore size: 0.2 .Math.m). The obtained filtrate was supplied to a gel permeation chromatograph (2690 Separations Model, produced by Waters) for GPC measurement at a sample flow rate of 1 mL/min and a column temperature of 40° C. The polystyrene equivalent molecular weight of the acrylic polymer was measured, and the weight average molecular weight (Mw) and the molecular weight distribution (Mw/Mn) were determined. A column used was GPC KF-806L (produced by Showa Denko K.K.). A detector used was a differential refractometer.

Synthesis Example 2

Preparation of Acrylic Polymer

[0135] An acrylic polymer was obtained as in Synthesis Example 1 except that the amount of ethyl acetate added was changed to 50 parts by weight.

Synthesis Example 3

Preparation of Acrylic Polymer

[0136] An acrylic polymer was obtained as in Synthesis Example 1 except that the monomer mixture was changed as shown in Table 1.

TABLE-US-00001 Synthesis Example 1 Synthesis Example 2 Synthesis Example 3 Acrylic polymer [% by weight] 2EHA (2-ethylhexyl acrylate) 96.9 96.9 80.0 AAc (acrylic acid) 3 3 1 HEA (2-hydroxyethyl acrylate) 0.1 0.1 19 Weight average molecular weight Mw [ × 10.sup.4] 53 148 50 Molecular weight distribution Mw/Mn 4.8 4.1 5.1

Synthesis Example A

Preparation of Compound (T1)

[0137] A reactor equipped with a thermometer, a stirrer, and a condenser was charged with 50 parts by weight of toluene, purged with nitrogen, and then heated to start reflux. After 30 minutes, while the toluene was kept at 75° C., 2 parts by weight of aluminum chloride (AlCl.sub.3) was added. Then, a solution containing 22.3 parts by weight of the monomer (a) and 27.7 parts by weight of the monomer (b) (the molar ratio was as shown in Table 2) shown in Table 2 in 50 parts by weight of toluene was gradually dropped over 1.5 hours for reaction. After 4 hours of polymerization reaction, the contents of the reactor were cooled while 0.1 parts by weight of pyridine was added into the reactor to neutralize hydrochloric acid produced from aluminum chloride (AlCl.sub.3). The precipitate resulting from neutralization was filtered out, and the obtained filtrate was subjected to liquid separation. Toluene was then evaporated, whereby a solid compound (T1) was obtained.

[0138] .sup.1H-NMR measurement of the obtained compound (T1) showed that the compound (T1) was a copolymer including a structural unit (A) derived from pyrocatechol, the monomer (a), and a structural unit (B) derived from α-pinene, the monomer (b).

[0139] A solution of the compound (T1) in tetrahydrofuran was filtered through a filter (material: polytetrafluoroethylene, pore size: 0.2 .Math.m). The obtained filtrate was supplied to a gel permeation chromatograph (2690 Separations Model, produced by Waters) for GPC measurement at a sample flow rate of 1 mL/min and a column temperature of 40° C. The polystyrene equivalent molecular weight of the compound (T1) was measured, and the weight average molecular weight (Mw) was determined. A column used was GPC KF-802.5L (produced by Showa Denko K.K.). A detector used was a differential refractometer.

[0140] The obtained compound (T1) was subjected to measurement using a differential scanning calorimeter (SII Exstar 6000/DSC 6220, produced by Hitachi High-Tech Science Corporation) in a nitrogen atmosphere at a heating rate of 10° C./min. The value obtained in the first run was used to determine the glass transition temperature.

[0141] A mold having a size of 10 × 50 mm was filled with the obtained compound (T1) and melted at a temperature 100° C. higher than the glass transition temperature of the compound to form a specimen having a thickness of 1 mm. This specimen was subjected to a tensile test using a tensile tester (TENSILON, produced by ORIENTEC) at a tensile speed of 200 mm/min, a clamp distance of 15 mm, and 25° C., whereby the Young’s modulus at 25° C. was measured.

[0142] First, 0.250 g of the obtained compound (T1) was weighed and diluted with 50 mL of cyclohexane. Next, 10.0 mL of a Wijs reagent (produced by Wako Pure Chemical Industries, Ltd., 0.1 mol/L iodine chloride/acetic acid solution) was added and sufficiently shaken. The mixture was left to stand for 30 minutes to allow reaction to proceed. Then, 10 mL of a 15% by weight aqueous potassium iodide solution and 30 mL of water were added and stirred. Further, a 0.1 N aqueous sodium thiosulfate solution (produced by Wako Pure Chemical Industries, Ltd.) was gradually dropped. When the solution turned pale yellow, three drops of a starch solution (10 g/L) was added. Thereafter, a 0.1 N aqueous sodium thiosulfate solution (produced by Wako Pure Chemical Industries, Ltd.) was gradually dropped (drop amount Y mL) until the solution was no longer blue. Subsequently, the drop amount (drop amount Z mL) for a blank was determined in the same manner except that no sample (compound (T1)) was added. The iodine value of the compound (T1) was determined using the following equation.

[00002]$\text{Iodine value}\left(\text{g}/100\text{g}\right)=\left(\text{Z - Y}\right)\times 1.269/0.250$

[0143] The bio-derived carbon content of the obtained compound (T1) was measured in conformity with ASTM D6866-20.

Synthesis Examples B to M

Preparation of Compound (T1)

[0144] A compound (T1) was obtained as in Synthesis Example A except that the monomers (a) and (b) were changed as shown in Table 2.

TABLE-US-00002 Synthesis Example A Synthesis Example B Synthesis Example C Synthesis Example D Synthesis Example E Synthesis Example F Synthesis Example G Synthesis Example H Synthesis Example I Synthesis Example J Synthesis Example K Synthesis Example L Synthesis Example M Compound (T1) [mol %] Monomer (a) Pyrocatechol 50 - - - - - - - - - - - 10 Pyrogallol - 60 50 30 10 3 0.5 10 10 10 10 10 - Monomer (b) Terpene monomer α-Pinene 50 40 50 70 90 97 99.5 - - 80 80 - - β-Pinene - - - - - - - 90 - - - - - Limonene - - - - - - - - 90 - - - - Vinyl monomer Styrene - - - - - - - - - 10 - 90 - Conjugated diene monomer Isoprene - - - - - - - - - - 10 - 90 Iodine value (C═C bond content) g/100 g 93 75 93 130 168 180 185 168 168 149 186 0 213 Weight average molecular weight Mw 790 510 540 530 560 620 710 1500 900 900 850 3500 1000 Glass transition temperature [° C] 30 32 31 30 32 34 36 40 42 45 30 48 -20 Young’s modulus (25° C.) [MPa] 78 81 80 80 85 85 86 91 90 96 74 104 0.6 Bio-derived carbon content [%] 63 100 100 100 100 100 100 100 100 91 95 8 0

Example 1

Production of Adhesive Tape

[0145] Thirty parts by weight of the compound (T1) (Synthesis Example A) was added to 100 parts by weight of the solids of the acrylic polymer (Synthesis Example 1). Further, 30 parts by weight of ethyl acetate (produced by Fuji Chemicals Ltd.) and 2.5 parts by weight of an isocyanate crosslinking agent (produced by Nippon Polyurethane Industry Co., Ltd., product name “Coronate L45”) were added and stirred to prepare an adhesive composition solution.

[0146] A release film having a thickness of 150 .Math.m was provided. The adhesive composition solution was applied to the release-treated side of the release film and dried at 100° C. for five minutes to form an adhesive layer having a thickness of 50 .Math.m. This adhesive layer was bonded to a surface of a corona-treated PET film having a thickness of 50 .Math.m as a substrate. Subsequently, the same adhesive layer as above was bonded to the opposite surface of the substrate in the same manner. The adhesive layers were aged by heating at 40° C. for 48 hours. This produced an adhesive tape in which the adhesive layers were laminated on both surfaces of the substrate and the release films covered the surfaces of the adhesive layers.

Measurement of Gel Fraction

[0147] The adhesive tape was cut to a flat rectangular shape with a size of 50 mm × 100 mm to prepare a specimen. The specimen was immersed in ethyl acetate at 23° C. for 24 hours, then taken out of the ethyl acetate, and dried at 110° C. for 1 hour. The weight of the dried specimen was measured, and the gel fraction was calculated using the following equation (1). No release film for protecting the adhesive layers was laminated on the specimen.

[00003]$\begin{array}{cc}\text{Gel fraction}\left(\%\text{by weight}\right)=100\times \left({\text{W}}_2{\text{- W}}_0\right)/\left({\text{W}}_1{\text{- W}}_0\right)& \text{­­­(1)}\end{array}$

(W.sub.0: weight of substrate, W.sub.1: weight of specimen before immersion, W.sub.2: weight of specimen after immersion and drying)

Measurement of Shear Storage Modulus

[0148] A measurement sample consisting only of the adhesive layer was prepared. A dynamic viscoelastic spectrum from -50° C. to 200° C. of the obtained measurement sample was measured using a viscoelastic spectrometer (DVA-200, produced by IT Measurement Co., Ltd.) at 5° C./min and a measurement frequency of 10 Hz in a low-heating-rate, shear deformation mode, and the storage modulus at 25° C. was determined.

Measurement of Loss Tangent (tanδ) Peak Temperature

[0149] A measurement sample consisting only of the adhesive layer was prepared. A dynamic viscoelastic spectrum from -100° C. to 200° C. of the obtained measurement sample was measured using a viscoelastic spectrometer (DVA-200 produced by IT Measurement Co., Ltd.) at 5° C./min and a measurement frequency of 10 Hz in a low-heating-rate, shear deformation mode. From the obtained dynamic viscoelastic spectrum, the loss tangent (tanδ) peak temperature was determined.

Examples 2 to 23 and Comparative Examples 1 and 2

[0150] An adhesive tape was obtained as in Example 1 except that the type and amount of the acrylic polymer, the compound (T1), the tackifier resin (T2), and the crosslinking agent were changed as shown in Table 3. The tackifier resins (T2) and crosslinking agents used are as follows.

[0151] Rosin ester resin (produced by Arakawa Chemical Industries Ltd., product name “Pinecrystal KE359”)

[0152] Terpene phenolic resin (produced by Yasuhara Chemical Co., Ltd., product name “YS Polyster G150”)

[0153] Isocyanate crosslinking agent (produced by Nippon Polyurethane Industry Co., Ltd., product name “Coronate L45”)

[0154] Epoxy crosslinking agent (produced by Mitsubishi Gas Chemical Company, Inc., product name “Tetrad E5XM”)

Example 24

[0155] Thirty parts by weight of the compound (T1) (Synthesis Example A) was added to 100 parts by weight of the solids of a styrene elastomer (SIS block copolymer, produced by Zeon Corporation, Quintac 3520, styrene content: 15% by weight, diblock proportion: 78% by weight). Further, 30 parts by weight of toluene (produced by Fuji Chemicals Ltd.) was added and stirred to prepare an adhesive composition solution.

[0156] A release film having a thickness of 150 .Math.m was provided. The adhesive composition solution was applied to the release-treated side of the release film and dried at 100° C. for five minutes to form an adhesive layer having a thickness of 50 .Math.m. This adhesive layer was bonded to a surface of a corona-treated PET film having a thickness of 50 .Math.m as a substrate. Subsequently, the same adhesive layer as above was bonded to the opposite surface of the substrate in the same manner. The adhesive layers were aged by heating at 40° C. for 48 hours. This produced an adhesive tape in which the adhesive layers were laminated on both surface of the substrate and the release films covered the surfaces of the adhesive layers.

Examples 25 to 53 and Comparative Examples 3 and 4

[0157] An adhesive tape was obtained as in Example 24 except that the type and amount of the styrene elastomer, the compound (T1), and the tackifier resin (T2) were changed as shown in Table 4 or 5. The styrene elastomers and tackifier resins (T2) used are as follows.

[0158] Styrene elastomer (SIS block copolymer, produced by Zeon Corporation, Quintac 3520, styrene content: 15% by weight, diblock proportion: 78% by weight)

[0159] Styrene elastomer (SIS block copolymer, produced by Zeon Corporation, Quintac 3433N, styrene content: 16% by weight, diblock proportion: 56% by weight)

[0160] Styrene elastomer (SIS block copolymer, produced by Zeon Corporation, Quintac 3421, styrene content: 14% by weight, diblock proportion: 26% by weight)

[0161] Styrene elastomer (SIS block copolymer, produced by Zeon Corporation, Quintac 3450, styrene content: 19% by weight, diblock proportion: 30% by weight)

[0162] Styrene elastomer (SIS block copolymer, produced by Zeon Corporation, Quintac 3280, styrene content: 25% by weight, diblock proportion: 17% by weight)

[0163] Styrene elastomer (SBS block copolymer, produced by Kraton Performance Polymer Japan, Kraton DX410, styrene content: 18% by weight, diblock proportion: 60% by weight)

[0164] Terpene resin (produced by Yasuhara Chemical Co., Ltd., product name “YS Resin PX 1150”)

Evaluation

[0165] The adhesive tapes obtained in the examples and the comparative examples were evaluated as follows. Tables 3 to 5 show the results.

180° Peel Test

[0166] The adhesive tape was cut into a 25-mm-wide specimen. The adhesive layer of the obtained specimen was placed on a stainless steel (SUS304) plate (produced by Nippon Testpanel Co., Ltd.), a polypropylene (PP) plate (produced by Nippon Testpanel Co., Ltd.), or a polytetrafluoroethylene (PTFE) plate (produced by Nippon Testpanel Co., Ltd.). Subsequently, a 2-kg rubber roller was moved back and forth once on the specimen at a rate of 300 mm/min to bond the specimen and the stainless steel (SUS304) plate, polypropylene (PP) plate, or polytetrafluoroethylene (PTFE) plate. The specimen was then left to stand at 23° C. for one hour to prepare a test sample. The test sample after standing was subjected to a tensile test in the 180° direction at a peeling rate of 300 mm/min in conformity with JIS Z0237, and the peeling force was measured.

[0167] 180° Peel test for SUS [0168] oo (Excellent): peeling force of 20 N/inch or greater [0169] o (Good): peeling force of 15 N/inch or greater and less than 20 N/inch [0170] Δ (Fair): peeling force of 10 N/inch or greater and less than 15 N/inch [0171] × (Poor): peeling force of less than 10 N/inch

[0172] 180° Peel test for PP [0173] oo (Excellent): peeling force of 15 N/inch or greater [0174] o (Good): peeling force of 10 N/inch or greater and less than 15 N/inch [0175] Δ (Fair): peeling force of 5 N/inch or greater and less than 10 N/inch [0176] × (Poor): peeling force of less than 5 N/inch

[0177] 180° Peel test for PTFE [0178] oo (Excellent): peeling force of 5 N/inch or greater [0179] o (Good): peeling force of 3 N/inch or greater and less than 5 N/inch [0180] Δ (Fair): peeling force of 1 N/inch or greater and less than 3 N/inch [0181] × (Poor): peeling force of less than 1 N/inch

Alkali Resistance Test

[0182] The adhesive tape was cut into a size of 25 mm × 75 mm, and the release film on one surface was removed. The tape was bonded, as a backing, to a polyethylene terephthalate (PET) film having a thickness of 23 .Math.m to prepare a specimen. In an environment at 23° C., the release film covering the other adhesive surface of the specimen was removed, and the specimen was compression bonded to a surface of a stainless-steel (SUS304) plate by moving a 2-kg roller back and forth once thereon. Thus, a test sample before chemical solution immersion was obtained. Sodium hydroxide was diluted with ion-exchanged water to prepare an alkaline chemical solution having a pH of 12. The test sample before chemical solution immersion was immersed in the alkaline chemical solution for one day in an atmosphere of 60° C. The test sample was then taken out from the alkaline chemical solution, washed with ion-exchanged water, and then dried at 23° C. for one hour to prepare a test sample after chemical solution immersion. The obtained test sample before and after chemical solution immersion was checked for peeling of the adhesive tape from the stainless-steel plate. [0183] o (Good): The adhesive tape did not peel off at all. [0184] Δ (Fair): The adhesive tape only slightly peeled off at its edge. [0185] × (Poor): The entire adhesive tape peeled off.

TABLE-US-00003 Example Comparative Example 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 1 2 Base polymer [% by weight] Synthesis Example 1 (acrylic polymer) 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 - - 100 100 100 100 100 100 100 Synthesis Example 2 (acrylic polymer) - - - - - - - - - - - - - - - - 100 - - - - - - - - Synthesis Example 3 (acrylic polymer) - - - - - - - - - - - - - - - - - 100 - - - - - - - Compound (T1) [% by weight] Synthesis Example A (pyrocatechol/ α-pinene) 30 - - - - - - - - - - - - - - - - - - - - - - - - Synthesis Example B (pyrogallol 60 mol%/ α-pinene) - 30 - - - - - - - - - - - - - - - - - - - - - - - Synthesis Example C (pyrogallol 50 mol%/ α-pinene) - - 30 - - - - - - - - 1 10 35 10 40 30 30 30 30 30 - - - - Synthesis Example D (pyrogallol 30 mol%/ α-pinene) - - - 30 - - - - - - - - - - - - - - - - - - - - - Synthesis Example E (pyrogallol 10 mol%/ α-pinene) - - - - 30 - - - - - - - - - - - - - - - - - - - - Synthesis Example F (pyrogallol 3 mol%/ α-pinene) - - - - - 30 - - - - - - - - - - - - - - - - - - - Synthesis Example G (pyrogallol 0.5 mol%/ α-pinene) - - - - - - 30 - - - - - - - - - - - - - - - - - - Synthesis Example H (pyrogallol / β-pinene) - - - - - - - 30 - - - - - - - - - - - - - - - - - Synthesis Example I (pyrogallol/limonene) - - - - - - - - 30 - - - - - - - - - - - - - - - - Synthesis Example J (pyrogallol / α-pinene/styrene) - - - - - - - - - 30 - - - - - - - - - - - - - - - Synthesis Example K (pyrogallol / α-pinene/isoprene) - - - - - - - - - - 30 - - - - - - - - - - - - - - Synthesis Example L (pyrogallol/styrene) - - - - - - - - - - - - - - - - - - - - - 30 - - - Synthesis Example M (pyrocatechol/isoprene) - - - - - - - - - - - - - - - - - - - - - - 30 - - Tackifier resin (T2) [% by weight] KE359 (rosin ester resin) - - - - - - - - - - - - - - - - - - - - - - - 30 - G150 (terpene phenolic resin) - - - - - - - - - - - 39 30 5 50 - - - - - - - - - 30 Crosslinking agent [% by weight] L-45 (isocyanate crosslinking agent) 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 1.0 0.5 4.0 - 2.5 2.5 2.5 2.5 E5XM (epoxy crosslinking agent) - - - - - - - - - - - - - - - - - - - - 0.5 - - - - Physical properties Shear storage modulus (25° C.) [Pa/10.sup.5] 0.7 1.1 0.9 0.9 0.8 0.8 0.8 1.0 0.9 1.0 0.8 4.1 3.5 1. 7 4. 8 1.0 0.9 1.0 0.8 1.0 1. 2 1.1 0.7 2.0 3.1 Loss tangent peak temperature [° C] -9 7 3 -1 -5 -6 -6 0 -3 4 -7 22 19 8 29 7 4 13 3 3 3.0 8 -15 0 17 Gel fraction [% by weight] 30 20 25 30 35 35 40 25 25 25 25 35 30 20 30 20 25 25 10 70 80 35 30 30 30 Evaluation 180° Peel test for SUS ○ ○ ○○ ○○ ○○ ○ ○ ○○ ○ ○○ ○○ ○○ ○○ ○○ ○ ○ ○○ ○○ ○○ ○○ ○ ○ ○ ○ ○ 180° Peel test for PP Δ ○ ○○ ○○ ○○ ○ Δ ○○ ○○ ○○ ○○ ○ ○○ ○○ ○ ○ ○○ ○○ ○○ ○○ ○ Δ Δ × × 180° Peel test for PTFE Δ ○ ○○ ○○ ○○ ○ Δ ○○ ○○ ○○ ○○ Δ ○○ ○○ Δ ○ ○○ ○○ ○○ ○○ ○ Δ Δ × ×

TABLE-US-00004 Example 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 Base polymer [% by weight] SIS: Quintac 3520 Styrene content: 15% by weight Diblock proportion: 78% by weight 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 - - SIS: Quintac 3433N Styrene content: 16% by weight Diblock proportion: 56% by weight - - - - - - - - - - - - - - - - - - - - 100 - SIS: Quintac 3421 Styrene content: 14% by weight Diblock proportion: 26% by weight - - - - - - - - - - - - - - - - - - - - - 100 SIS: Quintac 3450 Styrene content: 19% by weight Diblock proportion: 30% by weight - - - - - - - - - - - - - - - - - - - - - - SIS: Quintac 3280 Styrene content: 25% by weight Diblock proportion: 17% by weight - - - - - - - - - - - - - - - - - - - - - - SBS:Kraton DX410 Styrene content: 18% by weight Diblock proportion: 60% by weight - - - - - - - - - - - - - - - - - - - - - - Compound (T1) [% by weight] Synthesis Example A (pyrocatechol/ α-pinene) 30 - - - - - - - - - - - - - - - - - - - - - Synthesis Example B (pyrogallol 60 mol%/ α-pinene) - 30 - - - - - - - - - - - - - - - - - - - - Synthesis Example C (pyrogallol 50 mol%/ α-pinene) - - 30 - - - - - - - 1 10 35 40 10 10 10 10 10 10 30 30 Synthesis Example D (pyrogallol 30 mol%/ α-pinene) - - - 30 - - - - - - - - - - - - - - - - - - Synthesis Example E (pyrogallol 10 mol%/ α-pinene) - - - - 30 - - - - - - - - - - - - - - - - - Synthesis Example F (pyrogallol 3 mol%/ α-pinene) - - - - - 30 - - - - - - - - - - - - - - - - Synthesis Example G (pyrogallol 0.5 mol%/ α-pinene) - - - - - - 30 - - - - - - - - - - - - - - - Synthesis Example H (pyrogallol/ β-pinene) - - - - - - - 30 - - - - - - - - - - - - - - Synthesis Example I (pyrogallol/limonene) - - - - - - - - 30 - - - - - - - - - - - - - Synthesis Example J (pyrogallol / α-pinene/styrene) - - - - - - - - - 30 - - - - - - - - - - - - Synthesis Example K (pyrogallol / α-pinene/isoprene) - - - - - - - - - - - - - - - - - - - - - - Synthesis Example L (pyrogallol / α-pinene/isoprene) - - - - - - - - - - - - - - - - - - - - - - Synthesis Example L (pyrogallol/styrene) - - - - - - - - - - - - - - - - - - - - - - Synthesis Example M (pyrocatechol/isoprene) - - - - - - - - - - - - - - - - - - - - - - Tackifier resin (T2) [% by weight] PX1150 (terpene resin) - - - - - - - - - - 39 30 5 - - 40 90 100 - - - - KE359 (rosin ester resin) - - - - - - - - - - - - - - - - - - 30 - - - G150 (terpene phenolic resin) - - - - - - - - - - - - - - - - - - - 30 - - Physical properties Shear storage modulus (25° C.) [Pa/10.sup.5] 1.9 1.8 1.9 1.8 1.7 1.7 1.7 1.8 1.8 1.7 2.3 2.0 1.9 2.5 3.7 2.3 4.0 4.6 2.1 2.5 1.8 1.8 Loss tangent peak temperature [° C] -34 -31 -31 -32 -31 -32 -33 -31 -31 -29 -17 -19 -27 -28 -40 -13 17 21 -21 -8 -30 -28 Evaluation 180° Peel test for SUS O O OO OO OO O O OO OO OO OO OO OO OO O OO OO O OO OO OO O 180° Peel test for PP Δ O OO OO OO O Δ OO OO OO O OO OO O O OO OO O OO OO OO Δ 180° Peel test for PTFE Δ Δ O O O Δ Δ O O O O OO O Δ Δ OO OO Δ O OO O Δ Alkali resistance test Δ O O O O O Δ O O O Δ O O O O O O O O O O O

TABLE-US-00005 Exam ple Compar Exam rative ple 46 47 48 49 50 51 52 53 3 4 Base polymer [% by weight] SIS: Quintac 3520 Styrene content: 15% by weight Diblock proportion: 78% by weight - - - - 100 100 - - 100 100 SIS: Quintac 3433N Styrene content: 16% by weight Diblock proportion: 56% by weight - - - - - - - - - - SIS: Quintac 3421 Styrene content: 14% by weight Diblock proportion: 26% by weight - - - - - - - - - SIS: Quintac 3450 Styrene content: 19% by weight Diblock proportion: 30% by weight 100 100 100 100 - - - - - - SIS: Quintac 3280 Styrene content: 25% by weight Diblock proportion: 17% by weight - - - - - - 100 - - - SBS: Kraton DX410 Styrene content: 18% by weight Diblock proportion: 60% by weight - - - - - - - 100 - - Compound (T1) [% by weight] Synthesis Example A (pyrocatechol / α -pinene) - - - - - - - - - - Synthesis Example B (pyrogallol 60 mol%/ α-pinene) - - - - - - - - - - Synthesis Example C (pyrogallol 50 mol%/ a -pinene) 10 10 10 10 - - 30 30 - - Synthesis Example D (pyrogallol 30 mol%/ α-pinene) - - - - - - - - - - Synthesis Example E (pyrogallol 10 mol%/ a-pinene) - - - - - - - - - - Synthesis Example F (pyrogallol 3 mol%/ a pinene) - - - - - - - - - - Synthesis Example G (pyrogallol 0.5 mol%/ a-pinene) - - - - - - - - - - Synthesis Example H (pyrogallol/ β -pinene) - - - - - - - - - - Synthesis Example I (pyrogallol/limonene) - - - - - - - - - - Synthesis Example J (pvrogallol/ a -pinene/styrene) - - - - - - - - - - Synthesis Example K (pyrogallol / α-pinene/isoprene) - - - - 30 - - - - - Synthesis Example L (pyrogallol/styrene) - - - - - - - - - - Synthesis Example M (pyrocatechol/isoprene) - - - - - 30 - - - - Tackifier resin (T2) [% by weight] PX1150 (terpene resin) - 40 90 100 - - - - - - KE359 (rosin ester resin) - - - - - - - - 30 - G150 (terpene phenolic resin) - - - - - - - - - 30 Physical properties Shear storage modulus (25° C.) [Pa/10.sup.5] 1.9 2. 3 3.5 6.0 1.8 1.3 2.1 1.9 2.0 2.2 Loss tangent peak temperature [° C] -29 -10 18 22 -33 -38 -29 -30 -25 -16 180° Peel test for SUS O OO OO O O O O O O O Evaluation 180° Peel test for PP O OO OO O O Δ Δ O × × 180° Peel test for PTFE Δ OO OO Δ Δ Δ Δ Δ × × Alkali resistance test O O O O O Δ O O × Δ

INDUSTRIAL APPLICABILITY

[0186] The present invention can provide a compound capable of increasing the adhesion strength of adhesive compositions, particularly, even to low polarity adherends. The present invention can also provide a method for producing the compound, an adhesive composition containing the compound, and an adhesive tape including an adhesive layer containing the adhesive composition.