Moisture-curing adhesives and articles

Abstract

This invention provides a novel technology that can reduce the viscosity of moisture-curing adhesives, even when using plant-derived polyols. [Solution] The moisture-curing adhesive 10 contains an isocyanate group-containing compound obtained by reacting a polyol containing a plant-derived polyol with a polyisocyanate, and the polyisocyanate itself, and the viscosity measured by a B-type viscometer under the conditions of rotor No. 4, rotation speed of 30 rpm, and temperature of 25°C is 5000 mPa·s or less.

Description

[Technical Field]

[0001] This disclosure relates to moisture-curing adhesives and articles. [Background technology]

[0002] Patent Document 1 discloses a solvent-free reactive adhesive comprising a polyol (A), a polyisocyanate (B) containing a reaction product of a polyol (b1) containing 30% by mass or more of a polyol derived from a vegetable oil and a polyisocyanate (b2) containing diphenylmethane diisocyanate, and a vegetable oil (C) substantially free of hydroxyl groups. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2024-092663 [Overview of the project] [Problems that the invention aims to solve]

[0004] The inventors of this application have been investigating moisture-curing adhesives containing isocyanate group-containing compounds, which are formed by reacting a polyol containing a plant-derived polyol with a polyisocyanate, in order to increase the biomass content. However, when using plant-derived polyols, there is a problem that the viscosity of the moisture-curing adhesive tends to become high.

[0005] This disclosure aims to provide a novel technology that can reduce the viscosity of moisture-curing adhesives, even when using plant-derived polyols. This disclosure can be implemented in the following forms. [Means for solving the problem]

[0006] An isocyanate group-containing compound obtained by reacting a polyol containing a plant-derived polyol with a polyisocyanate, The above polyisocyanate is contained, A moisture-curing adhesive whose viscosity, measured using a Type B viscometer under the conditions of rotor No. 4, rotation speed of 30 rpm, and temperature of 25°C, is 5000 mPa·s or less. [Effects of the Invention]

[0007] According to this disclosure, a novel technology is available that can reduce the viscosity of moisture-curing adhesives, even when using plant-derived polyols. [Brief explanation of the drawing]

[0008] [Figure 1] This is a schematic perspective view showing an article in which chips are bonded together with a moisture-curing adhesive. [Figure 2] This figure shows a partially enlarged view of the cross-section in Figure 1. [Figure 3] This is a diagram illustrating the method for evaluating compatibility. [Modes for carrying out the invention]

[0009] Herein lies a preferred example of this disclosure. [1] An isocyanate group-containing compound obtained by reacting a polyol containing a plant-derived polyol with a polyisocyanate. The above polyisocyanate is contained, A moisture-curing adhesive whose viscosity, measured using a Type B viscometer under the conditions of rotor No. 4, rotation speed of 30 rpm, and temperature of 25°C, is 5000 mPa·s or less. [2] A moisture-curing adhesive as described in [1], wherein the NCO% is 5% or more and 30% or less. [3] The moisture-curing adhesive according to [1] or [2], wherein the ratio of the total number of NCO groups of the polyisocyanate to the total number of OH groups of the polyol in the raw materials of the moisture-curing adhesive is 5 or more. [4] A moisture-curing adhesive as described in any one of items [1] to [3], wherein the biomass content is 3% or more and 40% or less. [5] An article in which chips are bonded together with a moisture-curing adhesive as described in any one of items [1] to [4].

[0010] The disclosure is described in detail below. In this specification, the upper and lower limits of each numerical range can be combined in any way. In this specification, when a numerical range is described using "-", it includes both the lower and upper limits unless otherwise specified. For example, the description "10-20" includes both the lower limit "10" and the upper limit "20". In other words, "10-20" has the same meaning as "10 or more and 20 or less". Furthermore, in this specification, the upper and lower limits of each numerical range can be combined in any way.

[0011] 1. Moisture-curing adhesive 10 The moisture-curing adhesive 10 contains an isocyanate group-containing compound obtained by reacting a polyol (A) containing a plant-derived polyol with a polyisocyanate (B), and polyisocyanate (B). The viscosity measured using a B-type viscometer under the conditions of rotor No. 4, rotation speed of 30 rpm, and temperature of 25°C is 5000 mPa·s or less. In the moisture-curing adhesive 10 of this disclosure, when reacting polyol (A) and polyisocyanate (B), an excess of polyisocyanate (B) is used relative to polyol (A), resulting in a state where the isocyanate group-containing compound formed by the reaction of polyol (A) and polyisocyanate (B) coexists with the excess polyisocyanate (B).

[0012] (1) Raw materials for moisture-curing adhesive 10 The moisture-curing adhesive 10 can be obtained from raw materials comprising a polyol (A) and a polyisocyanate (B). The raw materials of the moisture-curing adhesive 10 may further contain, if necessary, one or more selected from the group consisting of a diluent (C), a crosslinking agent (D), and other additives (E). In this specification, "the entire raw materials of the moisture-curing adhesive 10" means the sum of the polyol (A), polyisocyanate (B), diluent (C), crosslinking agent (D), and other additives (E).

[0013] (1.1) Polyol (A) The polyol (A) contains a plant-derived polyol (A1). The polyol (A) may contain only the plant-derived polyol (A1), or may use the plant-derived polyol (A1) and a petroleum-derived polyol (A2) in combination. When the total amount of the polyol (A) is 100 parts by mass, the blending amount of the plant-derived polyol (A1) is preferably 20 parts by mass or more, more preferably 50 parts by mass or more, and still more preferably 70 parts by mass or more from the viewpoint of improving the biomass ratio. The upper limit of the blending amount of the above plant-derived polyol (A1) is 100 parts by mass. The plant-derived polyol (A1) may be only one kind, or two or more kinds. The petroleum-derived polyol (A2) may also be only one kind, or two or more kinds.

[0014] The plant-derived polyol (A1) is preferably one or more selected from the group consisting of, for example, castor oil-based polyols, corn oil-based polyols, soybean oil-based polyols, cashew nut oil-based polyols, palm oil-based polyols, palm kernel oil-based polyols, coconut oil-based polyols, olive oil-based polyols, cottonseed oil-based polyols, safflower oil-based polyols, sesame oil-based polyols, sunflower oil-based polyols, and linseed oil-based polyols. The plant-derived polyol is particularly preferably a castor oil-based polyol.

[0015] Castor oil is a vegetable oil obtained from the seeds of the plant called castor of the Euphorbiaceae family. Castor oil is an ester of fatty acids and glycerin. The main component of castor oil fatty acids is ricinoleic acid. Ricinoleic acid usually occupies 80% by mass or more of the total fatty acids. Other components of castor oil fatty acids are, for example, unsaturated fatty acids such as oleic acid, linoleic acid, and linolenic acid, and saturated fatty acids such as palmitic acid and stearic acid.

[0016] Castor oil-based polyols are typically polyols produced using castor oil, castor oil fatty acids, hydrogenated castor oil obtained by hydrogenating castor oil, or hydrogenated castor oil fatty acids obtained by hydrogenating castor oil fatty acids. Examples of such castor oil-based polyols include one or more selected from the group consisting of castor oil, reaction products of castor oil and polyhydric alcohols, esterification reaction products of castor oil fatty acids and polyhydric alcohols, hydrogenated castor oil, reaction products of hydrogenated castor oil and polyhydric alcohols, and esterification reaction products of hydrogenated castor oil fatty acids and polyhydric alcohols. Examples of polyhydric alcohols used to obtain esterification reaction products include one or more selected from the group consisting of ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,6-hexanediol, neopentyl glycol, trimethylolpropane, ditrimethylolpropane, trimethylolethane, glycerin, diglycerin, pentaerythritol, dipentaerythritol, polyester polyol, polycaprolactone polyol, polytetramethylene glycol polyol, polybutadiene polyol, polycarbonate polyol, and acrylic polyol. Castor oil-based polyols may be made using only one of the above compounds or two or more.

[0017] Specific examples of castor oil-based polyols include, for example, URIC H-30, URIC H-31, URIC H-52, URIC H-57, URIC H-62, URIC H-73X, URIC H-81, URIC H-102, URIC H-420, URIC H-854, URIC H-870, URIC H-1823, URIC H-1824, URIC H-1830, URIC HF-2009, POLYCASTOR #10, POLYCASTOR #30, URIC Y-403, URIC Y-406, URIC AC-005, URIC AC-006, URIC AC-009, URIC H-368, URIC PH-319, URIC PH-5001, and URIC, all manufactured by Ito Oil Co., Ltd. Examples include HF-2009, and Toyokuni Oil Co., Ltd.'s TLM, LM-R, ELA-DR, HS CM, HS 2G-120, HS 2G-160R, HS 2G-270B, HS KA-001, HS CM-025P, HS CM-075P, and HS 3G-500B.

[0018] The number of functional groups, hydroxyl value, and number-average molecular weight of the plant-derived polyol (A1) are not particularly limited. The number of functional groups in the plant-derived polyol is preferably 1 to 4, more preferably 1.5 to 3.5, and even more preferably 1.8 to 3. The hydroxyl value of the plant-derived polyol is preferably 40 mg KOH / g or more and 180 mg KOH / g or less, more preferably 50 mg KOH / g or more and 140 mg KOH / g or less, and even more preferably 60 mg KOH / g or more and 100 mg KOH / g or less. The number-average molecular weight of plant-derived polyols is preferably 500 to 3000, more preferably 800 to 2300, and even more preferably 900 to 1800. The number-average molecular weight of plant-derived polyols can be calculated, for example, from the number of functional groups and the hydroxyl value.

[0019] The amount of plant-derived polyol (A1) blended is preferably 3% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, and may also be 25% by mass or more, or 30% by mass or more, when the total amount of raw materials of the moisture-curing adhesive 10 is considered to be 100% by mass, from the viewpoint of increasing the biomass content. The amount of plant-derived polyol blended is preferably 40% by mass or less, more preferably 35% by mass or less, and even more preferably 30% by mass or less, from the viewpoint of reducing viscosity. From these viewpoints, the amount of plant-derived polyol (A1) blended is preferably 3% by mass or more and 40% by mass or less, more preferably 10% by mass or more and 35% by mass or less, and even more preferably 20% by mass or more and 30% by mass or less. If two or more types of plant-derived polyol (A1) are included, it is preferable that the total blended amount be within the above range.

[0020] Polyol (A) may contain petroleum-derived polyol (A2) with a number average molecular weight of 500 or more, from the viewpoint of ensuring various physical properties. The petroleum-derived polyol (A2) is not particularly limited. Examples of petroleum-derived polyol (A2) include polyether polyols, polymer polyols, polyester polyols, etc.

[0021] Polyether polyols are, for example, alkylene oxide adducts of polyhydric alcohols, polytetramethylene ether glycol, etc. Polyhydric alcohols are, for example, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, trimethylene glycol, glycerin, trimethylolpropane, pentaerythritol, etc. Alkylene oxides are, for example, one or more of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, epichlorohydrin, and styrene oxide.

[0022] The number of functional groups, hydroxyl value, and weight-average molecular weight of the petroleum-derived polyol (A2) are not particularly limited. The number of functional groups in the petroleum-derived polyol (A2) is preferably 2 to 4, more preferably 2 to 3, and even more preferably 2. The hydroxyl value of the petroleum-derived polyol (A2) is preferably 30 mg KOH / g or more and 140 mg KOH / g or less, more preferably 35 mg KOH / g or more and 110 mg KOH / g or less, and even more preferably 40 mg KOH / g or more and 80 mg KOH / g or less. The weight-average molecular weight of the petroleum-derived polyol (A2) is preferably 500 to 5000, more preferably 1000 to 4000, and even more preferably 1500 to 3500. In this disclosure, the weight-average molecular weight of the polyether polyol can be measured, for example, by gel permeation chromatography (GPC).

[0023] Polyol (A) may contain petroleum-derived polyol (A3) with a number average molecular weight of less than 500 from the viewpoint of improving tensile strength. Petroleum-derived polyol (A3) is a polyol used, for example, as a crosslinking agent or chain extender. Specific examples of petroleum-derived polyol (A3) include dipropylene glycol, ethylene glycol, ethylene glycol, propylene glycol, 1,4-butanediol, glycerin, trimethylolpropane, etc.

[0024] The amount of petroleum-derived polyol (A2) blended is preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less, when the total amount of raw materials of the moisture-curing adhesive 10 is considered to be 100% by mass, from the viewpoint of ensuring the amount of plant-derived polyol. The lower limit of the amount of petroleum-derived polyol (A2) blended is 0% by mass, but may also be 3% by mass or more, 5% by mass or more, or 10% by mass or more. If two or more types of petroleum-derived polyol (A2) are included, it is preferable that the total blended amount be within the above range.

[0025] (1.2) Polyisocyanate (B) Polyisocyanate (B) is not particularly limited as long as it is a compound having two or more isocyanate groups (NCO groups). It is preferable that the polyisocyanate be selected from the group consisting of aromatic, aliphatic, and alicyclic isocyanate compounds, and modified versions thereof. There may be only one polyisocyanate, or two or more.

[0026] Aromatic isocyanate compounds include, for example, crude diphenylmethane diisocyanate (polymeric MDI), diphenylmethane diisocyanate (monomeric MDI), tolylene diisocyanate (TDI), naphthalene diisocyanate (NDI), p-phenylene diisocyanate (PPDI), xylene diisocyanate (XDI), tetramethylxylene diisocyanate (TMXDI), and tolidine diisocyanate (TODI). Aliphatic isocyanate compounds include, for example, hexamethylene diisocyanate (HDI), lysine diisocyanate (LDI), and lysine triisocyanate (LTI). Alicyclic isocyanate compounds include, for example, isophorone diisocyanate (IPDI), cyclohexyl diisocyanate (CHDI), hydrogenated XDI (H6XDI), and hydrogenated MDI (H12MDI).

[0027] Crude diphenylmethane diisocyanate (polymeric MDI) is, for example, a mixture of dinuclear MDI and polynuclear MDI with three or more nuclei. Polymeric MDI may be untreated crude MDI obtained by an MDI synthesis reaction, or it may be obtained by separating a desired amount of monomeric MDI from the above crude MDI by vacuum distillation and adjusting the composition.

[0028] Diphenylmethane diisocyanates (monomeric MDIs) include 4,4'-diphenylmethane diisocyanate, 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, and mixtures of two or more of these.

[0029] The polyisocyanate may be polymeric MDI, or a mixture of polymeric MDI and monomeric MDI. The mass ratio (polymeric MDI:monomeric MDI) of the polymeric MDI to monomeric MDI mixture is preferably 10:0-4:6, more preferably 9:1-5:5, and more preferably 8.5:1.5-5.5:4.5.

[0030] In the raw materials for the moisture-curing adhesive 10, the ratio of the total number of NCO groups in polyisocyanate (B) to the total number of OH groups in polyol (A) (hereinafter also referred to as "NCO / OH") is not particularly limited. From the viewpoint of reducing the viscosity of the moisture-curing adhesive 10, NCO / OH is preferably 5 or more, but may be 6 or more, 8 or more, 10 or more, 12 or more, 14 or more, 16 or more, 18 or more, 20 or more, or 22 or more. The upper limit of NCO / OH is not particularly limited, and may be, for example, 40 or less, 30 or less, or 25 or less.

[0031] If the NCO / OH ratio is above the lower limit mentioned above, a sufficient amount of polyisocyanate (B) can be contained in the moisture-curing adhesive 10 without reacting with polyol (A). Polyisocyanate (B) has a smaller molecular weight than the isocyanate group-containing compound which is a reaction product with polyol (A). Therefore, it is presumed that by containing polyisocyanate (B) in the moisture-curing adhesive 10, the polyisocyanate (B) acts like a diluent (plasticizer), thereby reducing the viscosity of the moisture-curing adhesive 10. Furthermore, since polyisocyanate (B) contains two or more NCO groups as reactive groups, it is presumed that it can contribute to ensuring the performance of the moisture-curing adhesive 10 compared to diluents (plasticizers) that do not have reactive groups.

[0032] (1.3) Diluent (C) The moisture-curing adhesive 10 preferably contains a diluent (C) from the viewpoint of reducing viscosity. The diluent (C) is not particularly limited. A compound also called a plasticizer is preferred as the diluent (C). The diluent (C) is preferably one or more selected from the group consisting of aliphatic dibasic acid esters, phthalic acid esters, epoxy esters, and phosphate esters, and an aliphatic dibasic acid-based plasticizer is more preferred. The diluent (C) may be only one type or two or more types.

[0033] The aliphatic dibasic acid ester is preferably one or more selected from the group consisting of adipic acid esters, sebacate acid esters, and azelaic acid esters. In these esters, the alcohol constituting the ester by dehydration condensation is preferably an aliphatic alcohol having 3 to 13 carbon atoms. Specific examples of aliphatic dibasic acid esters include diisononyl adipate (DINA), dioctyl adipate (DOA), diisodecyl adipate, dibutyl sebacate (DBS), dioctyl sebacate (DOS), and dioctyl azelaic acid (DOZ).

[0034] From the viewpoint of reducing viscosity, the amount of diluent (C) to be blended is preferably 5% by mass or more, more preferably 10% by mass or more, and even more preferably 15% by mass or more, when the total amount of raw materials of the moisture-curing adhesive 10 is considered to be 100% by mass. From the viewpoint of ensuring the performance of the moisture-curing adhesive 10, the amount of diluent (C) to be blended is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 28% by mass or less. From these viewpoints, the amount of diluent (C) to be blended is preferably 5% by mass or more and 35% by mass or less, more preferably 10% by mass or more and 30% by mass or less, and even more preferably 15% by mass or more and 28% by mass or less.

[0035] (1.4) Crosslinking agent (D) The moisture-curing adhesive 10 may contain a crosslinking agent (D) from the viewpoint of improving tensile strength. Examples of crosslinking agents (D) include ethylenediamine, propylenediamine, hexamethylenediamine, tolylenediamine, xylylenediamine, diphenyldiamine, diaminodiphenylmethane, diaminocyclohexylmethane, piperazine, 2-methylpiperazine, isophoronediamine, and the like.

[0036] (1.5) Other additives (E) The moisture-curing adhesive 10 may further contain additives such as monools, antioxidants, UV absorbers, hydrolysis inhibitors, anti-bacterial agents, thickeners, plasticizers, defoamers, pigments, and fillers, as needed. Furthermore, to further enhance adhesive performance, it may contain adhesive aids such as silane coupling agents, phosphoric acid, phosphoric acid derivatives, acid anhydrides, and adhesive resins. It may also contain known catalysts, additives, etc., to adjust the curing reaction. These other components may consist of only one type or two or more types.

[0037] (2) Requirements regarding viscosity The moisture-curing adhesive 10 has a viscosity of 5000 mPa·s or less, as measured by a Type B viscometer under the conditions of rotor No. 4, rotation speed of 30 rpm, and temperature of 25°C. From the viewpoint of ease of adhesion to the object to be used, the viscosity is preferably 3000 mPa·s or less, more preferably 1500 mPa·s or less, and even more preferably 1000 mPa·s or less. The lower limit of the viscosity is not particularly limited, and is usually 100 mPa·s or more.

[0038] The viscosity of the moisture-curing adhesive 10 tends to be reduced, for example, by increasing the NCO / OH ratio. In addition, the viscosity of the moisture-curing adhesive 10 tends to be reduced, for example, by increasing the amount of diluent (C) added, within a range that does not impair the adhesive strength of the moisture-curing adhesive 10.

[0039] (3) Requirements regarding NCO% The NCO% of the moisture-curing adhesive 10 is preferably 5% to 30%, more preferably 8% to 25%, and even more preferably 10% to 23%, from the viewpoint of balancing adhesive strength and reactivity. Here, the method for measuring NCO% is in accordance with the method for determining the isocyanate group content described in JIS K 1603-1:2007 Method B.

[0040] The NCO% of the moisture-curing adhesive 10 can be controlled, for example, by adjusting the number of functional groups and the amount of polyol (A) and polyisocyanate (B) depending on the amount of components other than polyol (A) and polyisocyanate (B).

[0041] (4) Requirements regarding biomass content The biomass content of the moisture-curing adhesive 10 is preferably 3% to 40%, more preferably 10% to 35%, and even more preferably 20% to 30%. The biomass content of the moisture-curing adhesive 10 represents the total weight ratio of biomass-derived raw materials used in the manufacture of the moisture-curing adhesive 10 to the total amount of raw materials for the moisture-curing adhesive 10. For example, when only plant-derived polyols are used as biomass-derived raw materials, the biomass content of the moisture-curing adhesive 10 can be calculated using the following formula (1).

[0042] Biomass content of moisture-curing adhesive = ((A × B) / C) × 100 ... (1) A: Amount of plant-derived polyol (parts by mass) B: Plant-derived polyol content (%) / 100 C: Total amount (parts by mass) of raw materials for moisture-curing adhesive "Plant-derived polyol content (%) / 100" refers to the mass percentage of plant-derived materials among the raw materials of the plant-derived polyol. "Total amount of raw materials for moisture-curing adhesive" refers to the total mass parts of all components contained in the raw materials of the moisture-curing adhesive. All components include polyol (A), polyisocyanate (B), diluent (C), crosslinking agent (D), and other additives (E), etc.

[0043] The biomass content of the moisture-curing adhesive 10 can be increased, for example, by increasing the amount of plant-derived polyols used. Alternatively, the biomass content of the moisture-curing adhesive 10 can also be increased by using plant-derived polyols with a high plant content (e.g., 80% or more).

[0044] (5) Objects to be used The materials to which the moisture-curing adhesive 10 can be used are not particularly limited. Examples of materials to which the moisture-curing adhesive 10 can be used include rubber, resin, metal, wood, and glass. Even when using plant-derived polyols, the viscosity of the moisture-curing adhesive 10 is reduced, resulting in good adhesion to the material to which it can be used. Therefore, the moisture-curing adhesive 10 is suitable for bonding chip-shaped and particulate materials.

[0045] 2. Method for manufacturing moisture-curing adhesive 10 The moisture-curing adhesive 10 can be manufactured by mixing raw materials containing polyol (A) and polyisocyanate (B) and reacting them for a predetermined time. When diluents (C), crosslinking agents (D), and other additives (E) are included as raw materials, they should be mixed together with the polyol (A) and polyisocyanate (B). The predetermined time and reaction temperature should be appropriately set so as to obtain an isocyanate group-containing compound obtained by reacting polyol (A) and polyisocyanate (B).

[0046] 3. Goods 20 Article 20 is an article in which chips 21 are bonded by the moisture-curing adhesive 10 described above, as shown in Figures 1 and 2. Figure 1 schematically shows the outer shape of some of the chips 21 that appear on the surface of article 20. The chips 21 are not particularly limited, and various chips can be used. From the viewpoint of material recycling, it is preferable that the chips 21 be made of recycled material.

[0047] The chip 21 is preferably a rubber chip or a resin foam chip. Rubber chips are, for example, chips made of known rubbers such as natural rubber, styrene-butadiene rubber, acrylonitrile-butadiene rubber, polyurethane rubber, and ethylene-propylene-diene rubber (EPDM). Resin foam chips are, for example, foam chips made of polyolefin resin, polyurethane resin, melamine resin, phenolic resin, or ethylene-vinyl acetate copolymer (EVA) resin.

[0048] The particle size and density of the chip 21 are not particularly limited. The particle size of the chip 21 is, for example, 3 mm or more and 30 mm or less. The particle size of the chip 21 can be specified as the dimension of the largest part of the chip 21. The density of the chip 21 (according to JIS K 7222) is, for example, 5 kg / m³. 3 More than 200kg / m 3 The following applies:

[0049] The moisture-curing adhesive 10 adheres to the surface of the chip 21 and hardens. The moisture-curing adhesive 10 may bond the chips 21 together in such a way that gaps are formed between them, or it may fill the gaps between the chips 21 completely and bond them together. Figure 2 shows how gaps are formed between the chips 21.

[0050] The amount of moisture-curing adhesive 10 relative to the chip 21 is not particularly limited. When the total amount of the chip 21 is 100 parts by mass, the amount of moisture-curing adhesive 10 is preferably 5 parts by mass or more and 40 parts by mass or less, more preferably 8 parts by mass or more and 30 parts by mass or less, and even more preferably 10 parts by mass or more and 25 parts by mass or less.

[0051] The tensile strength and elongation of article 20 are not particularly limited. The tensile strength of article 20, measured according to the following measurement method in accordance with JIS K6251:2017, is preferably 15 N / cm². 2 The above is more preferable: 20 N / cm 2 That is all. 25 N / cm 2 More than 30N / cm 2 Above, 35N / cm2 It may be as described above. The upper limit value of the tensile strength of the above-described article 20 is not particularly limited, and for example, it may be 50 N / cm 2 or less. The elongation rate of the article 20 measured by the following measurement method in accordance with JIS K6251:2017 is preferably 3% or more, more preferably 5% or more, and still more preferably 9% or more. The upper limit value of the elongation rate of the above-described article 20 is not particularly limited, and for example, it may be 30% or less. [Measurement method] The test piece is prepared by punching out a test piece with a thickness of 10 mm, which is made by mixing an EPDM rubber chip of 3 mm or more and 30 mm or less and a moisture-curing adhesive 10 at a ratio of 100 / 18 (chip / moisture-curing adhesive, mass ratio), using a No. 1 dumbbell. The tensile test is performed in accordance with JIS K6251:2017. The tensile speed is 500 mm / min and the distance between the gauge lines is 40 mm. The tensile strength is calculated as the value obtained by dividing the maximum tensile force (N) recorded when the test piece is pulled until it is cut by the cross-sectional area of 1 cm of the test piece before the test. The elongation rate E is calculated by the following formula (2). 2 It is calculated as the value obtained by dividing the maximum tensile force (N) recorded when the test piece is pulled until it is cut by the cross-sectional area of 1 cm of the test piece before the test. The elongation rate E is calculated by the following formula (2). E = ((L1 - L0) / L0) × 100 ···(2) L0: Distance between the gauge lines before the test (mm), L1: Distance between the gauge lines at the time of cutting (mm)

[0052] The manufacturing method of the article 20 is not particularly limited. An example of the manufacturing method of the article 20 is to mix the chip 21 and the moisture-curing adhesive 10, put the mixture of the chip 21 and the moisture-curing adhesive 10 into a mold, and cure the moisture-curing adhesive 10 to bond the chips 21 together. The manufacturing method of the article 20 may cure the moisture-curing adhesive 10 by moisture in the atmosphere, or may supply water vapor to cure the moisture-curing adhesive 10. The curing of the moisture-curing adhesive 10 may be performed by heating, or may be performed at room temperature (non-heating). In the process of curing the moisture-curing adhesive 10, the mixture of the chip 21 and the moisture-curing adhesive 10 may not be pressurized, or may be compressed by pressure.

[0053] The use of article 20 is not particularly limited. Article 20 is suitable for use as an elastic paving material, carpet underlay as a building material, underfloor material, parcel shelf as an interior material for vehicles, trunk mat, floor mat, floor riser, spacer, etc. [Examples]

[0054] The following will provide a more detailed explanation using examples.

[0055] 1. Preparation of moisture-curing adhesive Polyol (A), polyisocyanate (B), and diluent (C) were mixed in the proportions shown in Table 1-3, and reacted at 70±5°C for 2 hours to prepare moisture-curing adhesives for the examples and comparative examples.

[0056] Details of each ingredient are as follows: Polyol (A): • Plant-derived polyol 1; Castor oil-based polyol (100% plant-derived), 2.7 functional groups, 161 mg KOH / g hydroxyl value, catalog number; URIC H-30, manufactured by Ito Oil Co., Ltd. • Plant-derived polyol 2; Castor oil-based polyol (100% plant-derived), 2.3 functional groups, 66 mg KOH / g hydroxyl value, catalog number: URIC H-1824, manufactured by Ito Oil Co., Ltd. • Petroleum-derived polyol 1; polyether polyol, 2 functional groups, weight-average molecular weight 3000 • Petroleum-derived polyol 2; dipropylene glycol, molecular weight 134

[0057] Polyisocyanate (B): • Polyisocyanate 1; a mixture of polymeric MDI and monomeric MDI, mass ratio polymeric MDI / monomeric MDI = 6 / 4 • Polyisocyanate 2; a mixture of polymeric MDI and monomeric MDI, mass ratio polymeric MDI / monomeric MDI = 8 / 2 • Polyisocyanate 3; Polymeric MDI The polymeric MDI mentioned above is Luplanate 200B, manufactured by BASF. The monomeric MDI is Luplanate MI, also manufactured by BASF.

[0058] Diluent (C): Diisononyl adipate (DINA)

[0059] [Table 1]

[0060] [Table 2]

[0061] [Table 3]

[0062] [Table 4]

[0063] Furthermore, polyol (A) and polyisocyanate (B) were mixed in the proportions shown in Table 4 and reacted at 70±5℃ for 2 hours to produce the moisture-curing adhesive of Example 12. Note that Example 12 is an example that does not include the diluent (C).

[0064] Details of each ingredient are as follows: Polyol (A): • Plant-derived polyol 3; Castor oil-based polyol (100% plant-derived), 2 functional groups, hydroxyl value 43 mgKOH / g, catalog number; URIC HF-2009, manufactured by Ito Oil Co., Ltd. • Petroleum-derived polyol 3; polypropylene glycol, 3 functional groups, weight-average molecular weight 5500, LUPRANOL 2095, manufactured by BASF. • Petroleum-derived polyol 4; polypropylene glycol, 4 functional groups, weight-average molecular weight 7400, SPECFLEX NC 630, manufactured by Dow.

[0065] Polyisocyanate (B): • Polyisocyanate 4; Monomeric MDI, LUPRANATE MI, NCO% 33.5%, Liquid diphenylmethane diisocyanate, manufactured by BASF. • Polyisocyanate 5; Monomeric MDI, LUPRANATE MS, NCO% 33.5%, Diphenylmethane diisocyanate, manufactured by BASF.

[0066] 2. Evaluation of moisture-curing adhesives The "NCO%", "viscosity", "NCO / OH", and "biomass content" were determined using the method described in the embodiment. A single-cylinder rotational viscometer (Type B viscometer) as specified in JIS Z 8803 was used to measure viscosity. The results are shown in Table 1-4.

[0067] Furthermore, the compatibility (liquid turbidity) of moisture-curing adhesives was evaluated using the following evaluation method. [Evaluation Method] The sample was placed in a standard 24 ml clear wide-mouth bottle (manufactured by AS ONE). Three black lines were drawn on a piece of white paper with a black marker. At room temperature (20-25°C), the sample was placed in front of the paper, and the condition of the black lines when viewed through the sample was evaluated according to the following criteria. A: The black line is clearly visible even through the sample. B: When viewed through the sample, the black line is unclear or invisible.

[0068] Note that the sample shown in Figure 3(A) is an example of a sample with an evaluation of "A". The sample shown in Figure 3(B) is an example of a sample with an evaluation of "B".

[0069] 3. Manufacturing of goods EPDM rubber chips (manufactured by Kokubu Green Farm, color rubber chip KG-13 (gray)) with a diameter of 3 mm to 30 mm were prepared. A mold was made by placing an aluminum frame on a metal plate. The rubber chips and the moisture-curing adhesive of the example were mixed in a ratio of 100 / 18 (chips / moisture-curing adhesive, by mass). The mixture of rubber chips and moisture-curing adhesive was placed in the mold and leveled to a thickness of 10 mm, and left to stand at room temperature under atmospheric pressure until the moisture-curing adhesive cured. No pressure compression was applied to the mixture of rubber chips and moisture-curing adhesive during the curing process. Furthermore, the moisture-curing adhesives in Comparative Examples 1 and 2 had excessively high viscosity and could not be adequately adhered to the chips, so no products were manufactured using them.

[0070] 4. Evaluation of goods The tensile strength and elongation were determined using the methods described in the embodiments. Tensile tests were performed using a Shimadzu Autograph AG-X plus in accordance with JIS K 6251. The results are shown in Table 1-4.

[0071] 5.Results The evaluation results are shown in Table 1-4. Experimental Examples 1-12 satisfy the following requirements (1)-(3). • Requirement (1): Contains an isocyanate group-containing compound obtained by reacting a polyol, including a plant-derived polyol, with a polyisocyanate. • Requirement (2): Contains polyisocyanate. Requirement (3): The viscosity measured using a Type B viscometer under the conditions of rotor No. 4, rotation speed 30 rpm, and temperature 25°C is 5000 mPa·s or less. In contrast, Comparative Examples 1 and 2 do not meet the following requirements. Comparative Example 1 and Comparative Example 2 do not meet requirement (3).

[0072] The moisture-curing adhesives of Examples 1-12 adhered uniformly to the chips, clinging to them evenly. The moisture-curing adhesives of Examples 1-12 achieved a biomass content of 5.0% or more. The moisture-curing adhesives of Examples 1-12 achieved practical tensile strength, elongation, and other performance characteristics while using plant-derived polyols. These Examples 1-12 were judged to be practical and given a "pass" rating. On the other hand, the moisture-curing adhesives in Comparative Example 1 and Comparative Example 2 were deemed "failures" because they could not be adequately adhered to the chips.

[0073] This example provides a novel technology that can reduce the viscosity of moisture-curing adhesives, even when using plant-derived polyols.

[0074] This disclosure is not limited to the embodiments detailed above, and various modifications or changes are possible within the scope of this disclosure.

Claims

1. An isocyanate group-containing compound obtained by reacting a polyol containing a plant-derived polyol with a polyisocyanate, The above polyisocyanate is contained, A moisture-curing adhesive whose viscosity, measured using a Type B viscometer under the conditions of rotor No. 4, rotation speed of 30 rpm, and temperature of 25°C, is 5000 mPa·s or less.

2. A moisture-curing adhesive according to claim 1, wherein the NCO% is 5% or more and 30% or less.

3. The moisture-curing adhesive according to claim 1, wherein the ratio of the total number of NCO groups of the polyisocyanate to the total number of OH groups of the polyol in the raw materials of the moisture-curing adhesive is 5 or more.

4. A moisture-curing adhesive according to claim 1, wherein the biomass content is 3% or more and 40% or less.

5. An article having chips bonded together with a moisture-curing adhesive according to any one of claims 1 to 4.

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