JP5970925B2 - One-part moisture curable resin composition, sealing material and adhesive using the same - Google Patents

Description

  The present invention relates to a one-part moisture curable resin composition, a sealing material using the same, and an adhesive.

  Sealing materials are widely used in buildings and the like for filling joints and gaps between various members to ensure watertightness and airtightness. Typical sealing materials for buildings include sealing materials made of urethane resin, modified silicone resin, silicone resin, polysulfide resin and the like. Due to differences in curing methods, the sealing material has a two-component type (two-component type) that is cured by mixing the main agent and the curing agent, and a one-component type (one-component type) that is cured using moisture and oxygen in the air. )

  Of these, one-component sealants, especially one-component urethane sealants consisting of urethane prepolymers containing isocyanate groups at the ends, do not require the mixing of the main agent and curing agent, and cure due to mismeasurement of the main agent and curing agent. Since there is no defect, it is excellent in workability and can be used with confidence. In addition, a one-component urethane sealant composed of a urethane prepolymer containing an isocyanate group at the end is low in modulus and high elongation after curing, has good rubber elasticity, and has excellent adhesion and durability. The usage is increasing year by year.

  In order to improve heat resistance and heat-and-moisture resistance in a one-component urethane resin composition, a method using a castor oil-based polyol as a raw material for a urethane prepolymer has been proposed (for example, see Patent Documents 1 and 2).

JP 2010-150475 A JP 2011-1426 A

  However, when castor oil-based polyol is used as the raw material for the urethane prepolymer, the cured product of the one-component urethane resin composition decreases in elongation and increases in modulus, so that it can be applied to a one-component urethane sealant. Is difficult.

  Castor oil-based polyols have a lower molecular weight than general polyols (eg, polypropylene-based polyols), and the isocyanate content increases when prepolymerized. Become.

  In view of the above problems, the present invention provides a one-part moisture curable resin composition that suppresses a decrease in elongation and an increase in modulus, has good foamability and curability, and can improve heat resistance and moist heat resistance. The purpose is to do.

The present invention includes the following (1) to ( 6 ).
(1) a urethane prepolymer (A) having an isocyanate group at a terminal obtained by reacting a polyisocyanate and a polyol;
A latent curing agent (B),
The polyol contains a polypropylene-based polyol (C) having 2 or more functional groups, a castor oil-based polyol (D) having 2 or more functional groups, and a monool (E) .
Content of the said latent hardening agent (B) is 0.1 mass part or more and 10 weight part or less with respect to 100 mass parts of said urethane prepolymers (A), 1 liquid moisture-curable resin composition characterized by the above-mentioned. object.
(2) The one-component moisture-curable resin composition according to (1), wherein the castor oil-based polyol (D) content is 5% by mass or more and 30% by mass or less in the total amount of the urethane prepolymer (A). .
(3) The one-component moisture-curing property according to (1) or (2), wherein the content of the monool (E) is 1% by mass or more and 30% by mass or less in the total amount of the urethane prepolymer (A). Resin composition.
(4) The one-component moisture-curable resin composition according to any one of (1) to (3), wherein the monool (E) is at least one of a polypropylene-based hydroxyl group-containing compound or a castor oil-based hydroxyl group-containing compound. Thing .
(5 ) A sealing material comprising the one-component moisture-curable resin composition according to any one of (1) to ( 4 ) above.
( 6 ) An adhesive comprising the one-component moisture-curable resin composition according to any one of (1) to ( 4 ).

  According to the present invention, a decrease in elongation and an increase in modulus are suppressed, and foamability and curability are good, and heat resistance and heat-and-moisture resistance can be improved.

  The present invention will be described in detail below. The present invention is not limited by the following modes for carrying out the invention (hereinafter referred to as embodiments). In addition, constituent elements in the following embodiments include those that can be easily assumed by those skilled in the art, those that are substantially the same, and those in a so-called equivalent range. Furthermore, the constituent elements disclosed in the following embodiments can be appropriately combined.

  The one-component moisture curable resin composition according to the present embodiment (hereinafter referred to as “the composition of the present embodiment”) is a urethane prepolymer (A) having an isocyanate group at the terminal obtained by reacting a polyisocyanate and a polyol. And the latent curing agent (B), wherein the polyol includes a polypropylene-based polyol (C) having 2 or more functional groups, a castor oil-based polyol (D) having 2 or more functional groups, and a monool. (E) is a 1-component moisture-curable resin composition.

<Urethane prepolymer (A)>
The urethane prepolymer (A) contained in the composition of this embodiment is a urethane prepolymer containing a plurality of isocyanate groups in the molecule at the molecular ends. Hereinafter, the urethane prepolymer (A) of this embodiment is referred to as “isocyanate group-containing urethane prepolymer (A) or urethane prepolymer (A)”. The urethane prepolymer (A) is preferably liquid at room temperature from the viewpoint of handling. In addition, the room temperature in this embodiment is 20 degreeC or more and 30 degrees C or less, Preferably it is the temperature of 25 degreeC vicinity. The production method of the urethane prepolymer (A) is not particularly limited, and conventionally known methods can be mentioned. The urethane prepolymer (A) is, for example, a reaction product obtained by reacting a polyisocyanate compound and a polyol compound so that an isocyanate group (NCO group) is excessive with respect to a hydroxy group (OH group). is there. The urethane prepolymer (A) generally contains 0.5% by mass or more and 10% by mass or less of NCO groups at the molecular ends.

[Polyisocyanate compound]
The polyisocyanate compound contained in the isocyanate group-containing urethane prepolymer which is the urethane prepolymer (A) is particularly limited as long as it is used in the production of the urethane prepolymer and has two or more isocyanate groups in the molecule. Not. Examples of the polyisocyanate compound include an aromatic polyisocyanate in which an isocyanate group is bonded to an aromatic hydrocarbon, an aliphatic polyisocyanate in which an isocyanate group is bonded to an aliphatic hydrocarbon, and an isocyanate group having an alicyclic hydrocarbon. And an alicyclic polyisocyanate bonded to the.

  Examples of the aromatic polyisocyanate include toluene such as TDI (for example, 2,4-tolylene diisocyanate (2,4-TDI), 2,6-tolylene diisocyanate (2,6-TDI), or a mixture thereof. Diisocyanate), MDI (e.g., diphenylmethane diisocyanate such as 4,4'-diphenylmethane diisocyanate (4,4'-MDI), 2,4'-diphenylmethane diisocyanate (2,4'-MDI), or mixtures thereof), 1 , 4-phenylene diisocyanate, diphenyl diisocyanate, polymethylene polyphenylene polyisocyanate, tolidine diisocyanate (TODI), 1,5-naphthalene diisocyanate (1,5-NDI), diphenyl ether diisocyanate, trif Such as methane triisocyanate.

  Aliphatic polyisocyanates include propylene diisocyanate, butylene diisocyanate, hexamethylene diisocyanate (HDI), pentamethylene diisocyanate, trimethylhexamethylene diisocyanate (TMHDI), lysine diisocyanate, norbornane diisocyanate (NBDI), xylylene diisocyanate (XDI), tetramethyl. And xylylene diisocyanate (TMXDI).

Examples of the alicyclic polyisocyanate include cyclohexane diisocyanate, methylene bis (cyclohexyl isocyanate), transcyclohexane-1,4-diisocyanate, isophorone diisocyanate (IPDI), bis (isocyanate methyl) cyclohexane (H ₆ XDI), dicyclohexylmethane diisocyanate (H ₁₂ MDI).

  These aromatic polyisocyanates, aliphatic polyisocyanates, alicyclic polyisocyanate carbodiimide-modified polyisocyanates, biuret-modified polyisocyanates, allophanate-modified polyisocyanates, polymethylene polyphenyl polyisocyanates (crude MDI or polymeric MDI), isocyanurates Examples thereof include modified polyisocyanates.

  Such polyisocyanate compounds can be used alone or in combination of two or more. Among these polyisocyanate compounds, TDI and MDI are preferable among the aromatic polyisocyanates, and among the aliphatic polyisocyanates, the viscosity becomes low after the reaction and the handling of the main agent containing the urethane-based prepolymer is easy. Among HDI, XDI and alicyclic polyisocyanate, IPDI is preferred.

[Polyol compound]
The polyol compound used in preparing the isocyanate group-containing urethane prepolymer (A) is composed of a polypropylene-based polyol (C) having 2 or more functional groups and a castor oil-based polyol (D) having 2 or more functional groups. And monool (E).

(Polypropylene polyol (C))
The polypropylene-based polyol (C) contained in the polyol compound of the composition of the present embodiment is not particularly limited as long as it has two or more hydroxy groups. Examples of the polypropylene-based polyol (C) include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerin, 1,1,1-trimethylolpropane, 1,2,5-hexanetriol, and 1,3-butanediol. It is obtained by adding at least one selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide and polyoxytetramethylene oxide to at least one selected from the group consisting of 1,4-butanediol and pentaerythritol. Polyol and the like. Specifically, for example, polyethylene glycol, polypropylene glycol (PPG), polypropylene triol, polyoxyethylene diol, polyoxyethylene triol, polyoxypropylene diol, polyoxypropylene triol, polyoxypropylene ether triol, ethylene oxide / propylene oxide Preferred examples include copolymers, polyethylene ether diols, polyethylene ether triols, polypropylene ether diols, polypropylene ether triols, polytetramethylene ether glycol (PTMEG), polytetraethylene glycol, sorbitol-based polyols and the like.

(Castor oil-based polyol (D))
The castor oil-based polyol (D) contained in the polyol compound of the composition of the present embodiment is not particularly limited as long as it contains a polyester polyol having two or more hydroxy groups and having a castor oil fatty acid as a skeleton.

  As the castor oil-based polyol (D), at least one of castor oil represented by the following formula (1) and an alkylene oxide adduct of castor oil, and at least one of alcohol, polyester polyol and polyether polyol are used. Transesterified product; castor oil fatty acid (a fatty acid obtained from castor oil, usually a mixture of ricinoleic acid and oleic acid, etc., may be ricinoleic acid alone), alcohol, polyester polyol and polyether polyol An ester compound with at least one of the following: a diol-type partially dehydrated or partially acylated product of castor oil; a transesterified product, an ester compound and a hydrogenated product of each compound of the partially dehydrated or partially acylated product, etc. Is mentioned. As the castor oil-based polyol, only one type may be used, or two or more types may be used. In addition, an oligomer can also be used as a castor oil and a castor oil fatty acid. As this oligomer, a 2-7mer, especially a 3-5mer is preferable, and it can also be set as a multimer. A saturated oligomer produced by hydrogenation of an unsaturated group can also be used.

  The castor oil-based polyol (D) may be produced according to a known production method, or a commercially available product may be used. As a commercial item of a castor oil type polyol (D), URIC H-30 (made by Ito Oil Co., Ltd.) etc. can be used, for example.

  The castor oil-based polyol (D) content is preferably 5% by mass or more and 30% by mass or less based on the total amount of the urethane prepolymer (A). When the content of the castor oil-based polyol (D) is 5% by mass or more, the composition of this embodiment is excellent in heat resistance and moist heat resistance. Further, when the content of the castor oil-based polyol (D) exceeds 30% by mass, the cured product of the composition of the present embodiment has a high modulus and a decrease in elongation occurs. Therefore, when the content of the castor oil-based polyol (D) is within the above range, the composition of the present embodiment has good foaming properties and excellent heat resistance and moist heat resistance.

  The composition of this embodiment can contain other polyol compounds in addition to the polypropylene-based polyol (C) and castor oil-based polyol (D). Examples of other polyol compounds include polyoxyalkylene polyols; polyester polyols; polymer polyols; polycarbonate polyols; polybutadiene polyols; hydrogenated polybutadiene polyols; acrylic polyols; ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and butanediol. , Low molecular weight polyols such as pentanediol and hexanediol. Of these, polyoxyalkylene polyols are preferred from the viewpoints of better compatibility and foam resistance, and excellent strength and elongation of the cured product.

(Monoall (E))
The monool (E) contained in the polyol compound of the composition of the present embodiment contains at least one of a polypropylene-based hydroxyl group-containing compound or a castor oil-based hydroxyl group-containing compound. Hereinafter, the polypropylene-based hydroxyl group-containing compound and castor oil-based hydroxyl group-containing compound of the present embodiment are referred to as “polypropylene-based monool, castor oil-based monool”.

  The polypropylene monool contained in the monool (E) of the composition of this embodiment will be described. The polypropylene monool contained in the monool (E) is not particularly limited as long as it has one hydroxy group and has a polypropylene ether skeleton as a main chain.

  Examples of the polypropylene monool include polyether monool. Examples of the polyether monool include aliphatic saturated alcohols such as methanol, ethanol, butanol and 2-ethylhexanol; alicyclic alcohols such as cyclopentanol and dimethylcyclohexanol; and aromatic alcohols such as benzyl alcohol. Carbocyclic alcohols such as furfuryl alcohol; at least one selected from monoalcohols of phenolic alcohols such as phenol and cresol, at least one selected from ethylene oxide, propylene oxide, butylene oxide, styrene oxide, etc. A polyether monool obtained by adding is suitably exemplified. Specific examples include polytetramethylene monool, polyethylene monool, polypropylene monool, polyoxypropylene monool, polyoxybutylene monool, and the like. Among these, polypropylene monool, polyoxypropylene monool, and the like are preferable. As a commercially available product of polypropylene monool, for example, Preminol 1004F (manufactured by Asahi Glass Co., Ltd.) can be used. Said polyether monool may be used individually by 1 type, and may be used in combination of 2 or more type.

  The number average molecular weight of the polypropylene monool is preferably 500 or more and 5000 or less, and preferably 1000 or more and 3000 from the viewpoint that the increase in the modulus and the decrease in the elongation rate of the cured product composed of the composition of the present embodiment can be suppressed. The following is more preferable.

  In addition, the production method of polypropylene monool is not particularly limited, but it is produced using a cesium compound, diethyl zinc, iron chloride, metal porphyrin, phosphazenium compound or a complex metal cyanide complex catalyst. A monool having a low degree is obtained, the content of low-molecular-weight impurities is small, and the coating film contamination property is low, which is preferable.

  The castor oil-based monool contained in the monool (E) of the composition of the present embodiment will be described. The castor oil-based monool contained in the monool (E) is not particularly limited as long as it has one hydroxy group and has a castor oil fatty acid skeleton as the main chain.

  Examples of castor oil monool include castor oil fatty acid (ricinoleic acid) lower alkyl ester, partially dehydrated castor oil, and partially acylated castor oil. Castor oil fatty acid lower alkyl ester can be obtained by transesterification of castor oil and lower alcohol, or esterification reaction of castor oil fatty acid and lower alcohol. Here, examples of the lower alcohol include methanol, propanol, and butanol. Partially dehydrated castor oil can be obtained by heating castor oil in the presence of an acidic catalyst such as sulfuric acid, phosphoric acid, p-toluenesulfonic acid and the like. Partially acylated castor oil can be obtained by partially acylating castor oil.

  Examples of the ester of castor oil or castor oil fatty acid and monool include monoglyceride of castor oil fatty acid, monoester of castor oil fatty acid and trimethylolpropane, monoester of castor oil fatty acid and polyethylene glycol, polypropylene glycol or polytetramethylene glycol It is done. As a commercial item of a castor oil type | system | group monool, URIC H-31 (made by Ito Oil Co., Ltd.) etc. can be used, for example. Said castor oil monool may be used individually by 1 type, and may be used in combination of 2 or more type.

  The content of the monool (E) is preferably 1% by mass or more and 30% by mass or less in the total amount of the urethane prepolymer (A). When the content of monool (E) is 1% by mass or less, the composition of the present embodiment does not sufficiently exhibit the effect of suppressing the decrease in elongation and the increase in modulus. Moreover, when content of monool (E) exceeds 30 mass%, the hardened | cured material of the composition of this embodiment may become too soft, and may not harden | cure. When the content of the monool (E) is within the above range, the cured product of the composition of the present embodiment can suppress a decrease in elongation and an increase in modulus, and can improve heat resistance and moist heat resistance.

  The monool (E) contained in the composition of this embodiment is a cured product comprising the composition of this embodiment by containing a predetermined amount of at least one or both of the above-described polypropylene-based hydroxyl group-containing compound or castor oil-based hydroxyl group-containing compound. The elastic recovery rate, modulus, and elongation rate of the object can be improved.

  The above-described polyol compounds can be used alone or in combination of two or more. The polyol compound is excellent in compatibility and foam resistance, and from the viewpoint of excellent strength and elongation of the cured product, a polypropylene-based polyol (C) having 2 or more functional groups and a castor oil-based polyol having 2 or more functional groups. It is preferable to contain (D) and monool (E).

  The amount of the polyisocyanate compound and the polyol compound in producing the urethane prepolymer (A) is such that the equivalent ratio of the isocyanate group to the hydrosyl group (isocyanate group (NCO group) / hydrosyl group (OH group)) is 1. It is preferably 2 or more and 2.5 or less, and more preferably 1.5 or more and 2.0 or less. When the equivalence ratio is within such a range, the viscosity of the urethane prepolymer (A) to be obtained becomes appropriate, and the residual amount of the unreacted polyisocyanate compound in the urethane prepolymer (A) can be reduced.

  The method for producing the urethane prepolymer (A) is not particularly limited. For example, the polyisocyanate compound and the polyol compound having the above-described equivalent ratio (NCO group / OH group) are heated and stirred at 50 ° C. or higher and 130 ° C. or lower. Can be produced. Moreover, if necessary, for example, a urethanization catalyst such as an organic tin compound, organic bismuth, or amine can be used.

  A urethane prepolymer (A) can be used individually or in combination of 2 or more types, respectively.

<Latent curing agent (B)>
The composition of this embodiment contains the latent hardening | curing agent (B) which reacts with a water | moisture content and produces | generates an active hydrogen group. The latent curing agent (B) does not function as a curing agent in a sealed state, that is, in a moisture blocking state, but is a hydrolyzed latent that opens as the sealed state and hydrolyzes in the presence of moisture to function as a curing agent. Curable hardener, does not function as a hardener at room temperature, but melts, dissolves or activates when a certain amount of heat is applied. Examples thereof include a photocuring initiator for initiating a group reaction. As the photocuring initiator, there are a visible curing initiator and an ultraviolet light (UV) curing initiator. A UV cure initiator is an initiator that initiates and induces cure in response to UV. A visible curing initiator is an initiator that initiates and induces curing in response to visible light. In the latent curing agent (B), two or more of these may be used in combination.

  Examples of the hydrolytic latent curing agent include ketimine compounds and oxazolidine compounds. Examples of the heat latent curing agent include dicyandiamide, imidazoles, hydrazines, epoxy adducts of amines, acid anhydrides, liquid phenols, aromatic amines, and the like. Examples of the photocuring initiator include aromatic diazonium salts, sulfonium salts, iodonium salts, and the like.

  In the present embodiment, among these, a hydrolytic latent curing agent that reacts with moisture as a curing component to generate an active hydrogen group is suitably used. Specific examples include amine-based latent curing agents such as ketimines and enamines that are a reaction product of a polyamine and a carbonyl compound; and oxazolidine compounds that are a reaction product of an amino alcohol and a carbonyl compound.

  The ketimine compound is not particularly limited as long as it is a compound having a ketimine bond (N = C), and examples thereof include a ketimine compound obtained by reacting a ketone with an amine.

  Examples of the ketone include methyl ethyl ketone, methyl isopropyl ketone, methyl tertiary butyl ketone, methyl cyclohexyl ketone, diethyl ketone, ethyl propyl ketone, ethyl butyl ketone, dipropyl ketone, dibutyl ketone, and diisobutyl ketone.

  The amine is not particularly limited, and specifically, for example, aromatic such as o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, m-xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, and diaminodiethyldiphenylmethane. Polyamine: ethylenediamine, propylenediamine, butylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexamethylenediamine, trimethylhexamethylenediamine, 1,2-propanediamine, iminobispropylamine, methyliminobispropyl Amine, aliphatic polyamines such as DuPont Japan products MPMD; N-aminoethylpiperazine, 3-butoxyisopropylamine, etc. A monoamine having an ether bond to the diamine and a diamine having a polyether skeleton represented by Jeffamine EDR148 manufactured by Sun Techno Chemical Co .; isophorone diamine, 1,3-bisaminomethylcyclohexane, 1-cyclohexylamino-3-aminopropane, 3-aminomethyl An alicyclic polyamine such as 3,3,5-trimethylcyclohexylamine; a diamine having a norbornane skeleton typified by Mitsui Chemicals, Inc. NBDA; a polyamide amine having an amino group at the molecular end of the polyamide; 2,5-dimethyl-2, Jeffermin D230, product of Sun Techno Chemical Co., which has 5-hexamethylenediamine, mensendiamine, 1,4-bis (2-amino-2-methylpropyl) piperazine, polypropylene glycol (PPG) as the skeleton Down D400 and the like.

  The oxazolidine compound is not particularly limited as long as it has one or more, preferably 2 to 6, oxazolidine rings in the molecule, which is a saturated 5-membered heterocyclic ring containing an oxygen atom and a nitrogen atom. The oxazolidine compound reacts with moisture (humidity) in the atmosphere to undergo hydrolysis, and the oxazolidine ring generates (regenerates) a secondary amino group and an alcoholic hydroxyl group, thereby causing a latent curing agent for an isocyanate group-containing prepolymer. It functions as. When the isocyanate group of the isocyanate group-containing prepolymer reacts with moisture, it forms a urea bond and cures, but at this time, carbon dioxide gas is also generated, bubbles are generated in the cured product due to carbon dioxide gas, and the appearance is deteriorated. However, when a mixture of an isocyanate group-containing prepolymer and an oxazolidine compound is exposed to moisture, the oxazolidine ring of the oxazolidine compound will react before the moisture reacts with the isocyanate group. Hydrolysis by moisture regenerates secondary amino groups and alcoholic hydroxyl groups, and these active hydrogens react with isocyanate groups and cure without generating carbon dioxide gas, so that the carbonic acid of the composition of this embodiment can be obtained. It can prevent foaming due to gas. From the viewpoint of shortening the curing time and storage stability of the composition of the present embodiment, it is preferable to use an oxazolidine compound as the latent curing agent (B).

  By using the oxazolidine compound as the latent curing agent (B), the composition of the present embodiment obtained can be moisture-cured at room temperature, has excellent storage stability, excellent curability, and has a curing rate. It can be adjusted and the curing time can be greatly shortened. Also, the foam resistance can be improved.

  Examples of the oxazolidine compound include a urethane bond-containing oxazolidine compound, an ester group-containing oxazolidine compound, an oxazolidine silyl ether, and a carbonate group-containing oxazolidine. These oxazolidine compounds are obtained by reacting a hydroxyl group of a compound having a hydroxyl group and an oxazolidine ring with an isocyanate group of a polyisocyanate compound or a carboxyl group of an organic carboxylic acid compound. Of these oxazolidine compounds, urethane bond-containing oxazolidine compounds are preferred from the viewpoint of easy production and low viscosity.

  Specific examples of the compound having a hydroxyl group and an oxazolidine ring include N-hydroxyalkyloxazolidine obtained by a dehydration condensation reaction between a secondary amino group of an alkanolamine and a carbonyl group of a ketone compound or an aldehyde compound. As a method for synthesizing the compound having a hydroxyl group and an oxazolidine ring, the carbonyl group of the aldehyde compound or the ketone compound is 1.0 mol or more, preferably 1.0 times mol with respect to 1.0 mol of the secondary amino group of alkanolamine. 1.5 times mol or less, more preferably 1.0 times mol or more and 1.2 times mol or less, and heating and refluxing in a solvent such as toluene, xylene, etc., dehydrating condensation while removing by-product water The method of performing reaction is mentioned. Excess aldehyde compounds and ketone compounds may be removed by distillation.

  Examples of the alkanolamine include diethanolamine, dipropanolamine, N- (2-hydroxyethyl) -N- (2-hydroxypropyl) amine and the like. Examples of the ketone compound include acetone, diethyl ketone, isopropyl ketone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl tert-butyl ketone, diisobutyl ketone, cyclopentanone, and cyclohexanone. Examples of the aldehyde compound include acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, 2-methylbutyraldehyde, n-hexylaldehyde, 2-methylpentylaldehyde, n-octylaldehyde, 3, 5 Aliphatic aldehyde compounds such as 1,5-trimethylhexylaldehyde; aromatic aldehyde compounds such as benzaldehyde, methylbenzaldehyde, trimethylbenzaldehyde, ethylbenzaldehyde, isopropylbenzaldehyde, isobutylbenzaldehyde, methoxybenzaldehyde, dimethoxybenzaldehyde, and trimethoxybenzaldehyde. Any of these may be used alone or in admixture of two or more.

  Of these, diethanolamine is preferred as the alkanolamine in terms of ease of production of the compound having a hydroxyl group and an oxazolidine ring, and excellent antifoaming properties when the resulting one-component room temperature curable sealing material is cured. Of the ketone compounds or aldehyde compounds, aldehyde compounds are preferred, and isobutyraldehyde, 2-methylpentylaldehyde, and benzaldehyde are more preferred.

  Specific examples of the compound having a hydroxyl group and an oxazolidine ring include 2-isopropyl-3- (2-hydroxyethyl) oxazolidine, 2- (1-methylbutyl) -3- (2-hydroxyethyl) oxazolidine, 3- (2 -Hydroxyethyl) -2- (1-methylbutyl) oxazolidine, 2-phenyl-3- (2-hydroxyethyl) oxazolidine and the like.

  As the urethane bond-containing oxazolidine compound, the hydroxyl group and the hydroxyl group of the compound having an oxazolidine ring and the isocyanate group of the organic isocyanate compound have an isocyanate group / hydroxyl molar ratio in the range of 0.9 to 1.2, preferably 0. Suitable examples include those obtained by reacting at a temperature of 50 ° C. or higher and 120 ° C. or lower in the presence or absence of an organic solvent.

  Examples of the organic isocyanate compound used for the synthesis of the urethane bond-containing oxazolidine compound include the same as those used for the synthesis of the aforementioned isocyanate group-containing prepolymer, and among them, the crystallinity of the urethane bond-containing oxazolidine compound is lowered. In view of improving the workability of the sealing material, aliphatic polyisocyanates are preferred, and hexamethylene diisocyanate (HDI) is particularly preferred.

  The ester group-containing oxazolidine compound can be obtained by reacting the aforementioned compound having a hydroxyl group and an oxazolidine ring with a lower alkyl ester of dicarboxylic acid or polycarboxylic acid.

  The oxazolidine silyl ether includes a compound having a hydroxyl group and an oxazolidine ring as described above, trimethoxysilane, tetramethoxysilane, triethoxysilane, dimethoxydimethylsilane, vinyltrimethoxysilane, vinyltriethoxysilane, 3-glycidoxypropyltri It can be obtained by dealcoholization reaction with alkoxysilane such as methoxysilane and 3-glycidoxypropyltriethoxysilane.

  The carbonate group-containing oxazolidine can be obtained by reacting the above-mentioned compound having a hydroxyl group and an oxazolidine ring with a carbonate such as diallyl carbonate using a polyhydric alcohol such as diethylene glycol or glycerin.

  Any of these may be used alone or in admixture of two or more.

  The oxazolidine compound preferably does not have an active hydrogen group-containing functional group such as an amino group or a hydroxyl group that reacts with an isocyanate group of a urethane-based prepolymer containing an isocyanate group at room temperature or an isocyanate group in the molecule. . This is to prevent a rise in the viscosity of the urethane-based prepolymer and a decrease in the anti-foaming performance of the oxazolidine compound. However, in the synthesis of the urethane bond-containing oxazolidine compound described above, a small amount of active hydrogen group-containing functional group or isocyanate group may remain in the molecule depending on the molar ratio selected. In this case, the object of the present invention is achieved. It can be regarded as not having above. The “small amount” means that the amount of the active hydrogen group-containing functional group or isocyanate group remaining in the molecule is preferably 0.05 mmol or less, more preferably 0.02 mmol or less per 1 g of the oxazolidine compound. .

  The amount of the oxazolidine compound used is such that the active hydrogen of the secondary amino group regenerated by hydrolysis of the oxazolidine compound is 0.3 mol or more and 1.0 mol relative to 1.0 mol of the isocyanate group in the isocyanate group-containing prepolymer. It is preferable to use so that it may become below, and it is more preferable to use so that it may become 0.5 mol or more and 1.0 mol or less.

  Examples of the imidazoles include imidazole compounds such as 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, and 2-phenyl-4-methylimidazole. Etc. An addition reaction product (epoxy adduct) between these and an epoxy compound is used as the thermal latent curing agent.

  Examples of the hydrazines include adipic acid dihydrazide and isophthalic acid dihydrazide. An addition reaction product (epoxy adduct) between these and an epoxy compound is used as the thermal latent curing agent.

  Examples of the amines include 2-dimethylaminoethylamine and 3-dimethylamino-N-propylamine. An addition reaction product (epoxy adduct) of these and an epoxy compound is used as a thermal latent curing agent.

  Examples of the acid anhydride include trimellitic acid anhydride, pyromellitic acid anhydride, hexahydrophthalic acid anhydride, methylhexahydrophthalic acid anhydride, nadic acid anhydride, methyl nadic acid anhydride, tetrahydrophthalic acid anhydride. Products, methyltetrahydrophthalic anhydride, dodecenyl succinic anhydride (DSA) and the like.

  Examples of the liquid phenol include diallyl bisphenol A, diallyl bisphenol F, allylated phenol novolac resin, allylated dihydronaphthalene, diallyl resorcin and the like.

  Examples of the aromatic amines include m-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, diaminodiethyldiphenylmethane, monomethyldiethyl-m-phenylenediamine, and the like.

  In the UV curing initiator, examples of the aromatic diazonium salt include p-methoxybenzenediazonium hexafluorophosphate. Examples of the aromatic sulfonium salt include triphenylsulfonium hexafluorophosphate. Examples of the aromatic iodonium salt include diphenyliodonium hexafluorophosphate. As other UV curing initiators, aromatic iodosyl salts, aromatic sulfoxonium salts, metallocene compounds, and the like can also be used.

  From the viewpoint of adjusting the curing rate of the isocyanate group-containing prepolymer, the content of the latent curing agent (B) is 0.1 parts by mass or more and 10 parts by mass with respect to 100 parts by mass of the isocyanate group-containing prepolymer (A). The following is preferable, and 1 to 10 parts by mass is more preferable. If the content of the latent curing agent (B) is less than 0.1 part by mass, the cured product of the composition of the present embodiment takes too much time until curing, resulting in poor curability and poor foamability. If the content of the latent curing agent (B) exceeds 10 parts by mass, the cured product of the composition of the present embodiment becomes too soft and the strength properties of the cured product are lowered. Therefore, when the content of the latent curing agent (B) is within the above range, the composition of the present embodiment can be moisture-cured within a predetermined time, and is excellent in storage stability and curability. The foam resistance can also be improved.

  The composition which concerns on this embodiment can contain various additives other than each component mentioned above as needed in the range which does not impair the objective of this invention. Examples of the additive include a filler, a plasticizer, a pigment, a dye, an anti-aging agent, an antioxidant, an antistatic agent, a flame retardant, an adhesion imparting agent, a stabilizer, a dispersant, and a solvent.

  Examples of the filler include organic or inorganic materials having various shapes. For example, wax clay, kaolin clay, calcined clay; silica sand, fumed silica, calcined silica, precipitated silica, ground silica, fused silica; diatomaceous earth; calcium carbonate, heavy calcium carbonate, precipitated calcium carbonate (light calcium carbonate) Colloidal calcium carbonate, iron oxide, zinc oxide, titanium oxide, barium oxide, magnesium oxide; magnesium carbonate, zinc carbonate; organic or inorganic filler such as carbon black; surface treatment with these fatty acids, resin acids, fatty acid esters, etc. Treated products, treated products surface-treated with a fatty acid ester urethane compound, and the like.

  Examples of the plasticizer include polypropylene glycol, diisononyl phthalate (DINP), dioctyl phthalate (DOP), dibutyl phthalate (DBP); dioctyl adipate, isodecyl succinate; diethylene glycol dibenzoate, pentaerythritol ester; butyl oleate And methyl acetylricinoleate; tricresyl phosphate, trioctyl phosphate; propylene glycol adipate polyester, butylene glycol adipate polyester; alkylsulfonic acid phenyl ester (for example, mezamol manufactured by Bayer) and the like. These may be used alone or in combination of two or more.

  The pigment may be either an inorganic pigment or an organic pigment. For example, organic pigments such as titanium dioxide, zinc oxide, ultramarine blue, bengara, lithopone, lead, cadmium, iron, cobalt, aluminum, hydrochloride, sulfate inorganic pigments, azo pigments, copper phthalocyanine pigments, and the like can be used.

  The dye is not particularly limited, and conventionally known dyes can be used. For example, black dye, yellow dye, red dye, blue dye, and brown dye can be mentioned.

  Examples of the antiaging agent include hindered phenol compounds, hindered amine compounds, and benzotriazole compounds.

  Examples of the antioxidant include butylhydroxytoluene (BHT) and butylhydroxyanisole (BHA).

  Examples of the antistatic agent include quaternary ammonium salts; hydrophilic compounds such as polyglycols and ethylene oxide derivatives.

  Examples of the flame retardant include chloroalkyl phosphate, dimethyl / methylphosphonate, bromine / phosphorus compound, ammonium polyphosphate, neopentyl bromide-polyether, and brominated polyether.

  Examples of the adhesion-imparting agent include terpene resins, phenol resins, terpene-phenol resins, rosin resins, xylene resins, and various silane coupling agents.

  Examples of the stabilizer include fatty acid silyl esters and fatty acid amide trimethylsilyl compounds.

  The dispersant refers to a substance that makes a solid into fine particles and disperses it in a liquid. Examples thereof include sodium hexametaphosphate, condensed sodium naphthalene sulfonate, and a surfactant.

  The solvent preferably has good compatibility with the solvent contained in the synthesis of other components in the composition of the present embodiment. Examples include methyl ethyl ketone (MEK), ethyl acetate, butyl acetate, cellosolve acetate, mineral spirit, toluene, xylene, and acetone. A solvent can be used individually or in combination of 2 or more types. The solvent is preferably used after sufficiently dehydrated and dried.

  The various additives described above can be used in appropriate combination.

  The method for producing the composition according to the present embodiment is not particularly limited. For example, the above essential components and optional components are rolled, kneader, extruder, universal stirrer under reduced pressure or in an inert gas atmosphere such as nitrogen. And a method of mixing by sufficiently kneading and uniformly dispersing using a stirring device such as a mixing mixer.

  Thus, the composition according to the present embodiment includes the urethane prepolymer (A) having an isocyanate group at the terminal obtained by reacting polyisocyanate and polyol, and the latent curing agent (B), and the polyol Contains a polypropylene-based polyol (C) having 2 or more functional groups, a castor oil-based polyol (D) having 2 or more functional groups, and a monool (E), thereby reducing elongation and modulus. While suppressing the rise, the foamability and curability are good, and the heat resistance and moist heat resistance can be improved.

  The composition according to the present embodiment is a moisture-curable type, and can be used as a one-component curable composition that is prepared by pre-mixing and storing all of the compounding components in advance and curing with moisture in the air after construction. Further, as a curing agent, components such as a curing catalyst, a filler, a plasticizer, and water are blended in advance and used as a two-component type in which the blending agent (material) and the polymer composition are mixed before use. You can also.

  The composition according to the present embodiment is a one-component type, and since all the blending components are blended in advance, the blending components containing moisture are used after being dehydrated and dried in advance, or by reducing the pressure during blending and kneading. It is preferable to dehydrate. When the composition according to this embodiment is exposed to moisture, the latent curing agent (B) undergoes a curing reaction due to hydrolysis and generates an amino group, and thus has excellent curability. Therefore, the obtained composition according to the present embodiment is stored in a closed container, and a cured product can be obtained at room temperature due to moisture in the air at the time of use. In addition, the curing reaction can be advanced by appropriately supplying water.

  Although the use of the composition according to the present embodiment is not particularly limited, the composition according to the present embodiment has the excellent characteristics as described above, so that it is for civil engineering, concrete, wood, metal, glass It is suitably used for applications such as sealing materials for plastics, adhesives, sealing agents, potting agents, elastic adhesives, coating materials, lining materials, structural adhesives in concrete and mortar, and cracking injection materials.

  As described above, the one-component moisture-curable resin composition of the present invention has been described in detail, but the present invention is not limited to the above examples, and various modifications and improvements can be made without departing from the gist of the present invention. Good.

  Hereinafter, the composition according to the present embodiment will be specifically described with reference to examples. However, the composition according to the present embodiment is not limited to these.

<Preparation of urethane prepolymer (A)>
Polypropylene polyols (C) 1 and (C) 2 shown in Table 1, castor oil polyol (D), polypropylene hydroxyl group-containing compound (E) 1, and castor oil hydroxyl group-containing compound (E) 2 are the same. After charging at a mass ratio (parts by mass) shown in the table and dehydrating at 120 ° C. under reduced pressure, the polyisocyanate compound was added in an amount such that the equivalent ratio of NCO groups / OH groups was 1.9, and the nitrogen substitution was performed at 80 ° C. for 24 hours. After mixing and stirring, urethane prepolymers (A) 1 to (A) 6 shown in Table 1 were prepared. Table 1 shows the amount of each component.

上記表１に示される各成分は、以下の通りである。
・ポリプロピレン系ポリオール（Ｃ）１：ポリオキシプロピレンジオール、官能基数２、数平均分子量３２００、商品名「エクセノール３０２０」、旭硝子株式会社製
・ポリプロピレン系ポリオール（Ｃ）２：ポリオキシプロピレントリオール、官能基数３、数平均分子量５１００、商品名「エクセノール５０３０」、旭硝子株式会社製
・ひまし油系ポリオール（Ｄ）：官能基数２．７、商品名「ＵＲＩＣ Ｈ３０」、伊藤製油株式会社製
・ポリプロピレン系水酸基含有化合物（Ｅ）１：ポリオキシプロピレンアルキルエーテル、商品名「プレミノール１００４Ｆ」、旭硝子株式会社製
・ひまし油系水酸基含有化合物（Ｅ）２：官能基数１、商品名「ＵＲＩＣ Ｈ３１」、伊藤製油株式会社製
・ポリイソシアネート化合物：トリレンジイソシアネート、商品名「コスモネートＴ−８０」、三井化学株式会社製

Each component shown in Table 1 is as follows.
Polypropylene polyol (C) 1: polyoxypropylene diol, number of functional groups 2, number average molecular weight 3200, trade name “Excenol 3020”, manufactured by Asahi Glass Co., Ltd. • Polypropylene polyol (C) 2: polyoxypropylene triol, number of functional groups 3, number average molecular weight 5100, trade name “Excenol 5030”, manufactured by Asahi Glass Co., Ltd. ・ castor oil-based polyol (D): functional group number 2.7, trade name “URIC H30”, manufactured by Ito Oil Co., Ltd. ・ polypropylene hydroxyl group-containing compound (E) 1: Polyoxypropylene alkyl ether, trade name “Preminol 1004F”, manufactured by Asahi Glass Co., Ltd. • Castor oil-based hydroxyl group-containing compound (E) 2: Functional group number 1, trade name “URIC H31”, manufactured by Ito Oil Co., Ltd. Polyisocyanate compound: Tolylene diisocyanate Anate, trade name “Cosmonate T-80”, manufactured by Mitsui Chemicals, Inc.

<Preparation of one-part moisture curable resin composition>
The urethane prepolymers (A) 1 to (A) 6 obtained above and the respective components shown in Table 2 below are blended in the mass ratio (parts by mass) shown in Table 2, and these are sufficiently used using an electric stirrer or the like. By mixing, each composition of Examples 1-8 and Comparative Examples 1-5 was prepared.

  About each composition obtained above, tensile adhesiveness was evaluated by the method shown below. The results are shown in Table 2.

<Tensile adhesion>
In accordance with the tensile adhesiveness test of JIS A1439 using each composition obtained, an H-type tensile test body (hereinafter referred to as a test body) was prepared using an anodized aluminum plate. The specimen was cured under conditions.
(Curing and curing conditions)
Initial adhesiveness: after curing for 14 days under conditions of 23 ° C. and 50% RH, curing for 14 days at 30 ° C. (hereinafter referred to as standard curing)
・ Heat and heat resistance: Standard curing (cured for 14 days at 23 ° C. and 50% RH, then cured for 14 days at 30 ° C.) and then cured for 28 days at 80 ° C. and 95% RH ・ Heat resistant adhesive: standard After curing (cured for 14 days at 23 ° C and 50% RH, then cured for 14 days at 30 ° C) and then cured at 80 ° C for 56 days

About each obtained test body, the tension test of each composition is performed according to the tensile adhesiveness test of JIS A1439, strength at the time of 50% elongation [N / cm ² ], maximum tensile strength at break [N / mm ² ] and the elongation [%] at the maximum elongation at break. The results are shown in Table 2. The evaluation criteria in Table 2 are as follows.
(Evaluation criteria)
- 50% strength at elongation ^{[N / cm 2]: 4N} / cm 2 or more 25 N / cm ² or less in the range, was evaluated as can be suitably used as a sealing material or the like.
Maximum tensile strength [N / cm ² ]: It was evaluated that the initial adhesiveness was 45 N / cm ² or more and that it was not melted due to wet heat and heat resistant adhesive properties.
Elongation rate [%] at maximum extension: It was evaluated that 400% or more was good as a sealing material.

<Curing property (tack free time)>
The tack-free time was measured by applying each obtained composition to the adherend surface and curing at 23 ° C. and about 50% RH. If the tack free time at about 23 ° C. was in the range of 1 to 7 hours, it was judged that the workability was good. Table 2 shows the measurement results of the tack free time.

<Foaming properties>
After the initial adhesion test of the H-type tensile test body prepared above, the fracture surface of the test body was visually observed to confirm the presence or absence of foaming. The case where foaming was not confirmed visually was evaluated as “◯”. The case where foaming was confirmed visually was evaluated as “x”. The evaluation results are shown in Table 2 below.

Each component shown in Table 2 is as follows.
Urethane prepolymers (A) 1 to (A) 6: Urethane prepolymers prepared as described above Latent curing agent (B): 3- (2-hydroxyethyl) -2- (1-methylbutyl) Oxazolidine, trade name “PHO”, manufactured by Yokohama Rubber Co., Ltd. ・ Surface treatment calcium carbonate: Sealets 200, manufactured by Maruo Calcium Co., Ltd. ・ Heavy calcium carbonate: Super S, manufactured by Maruo Calcium Co., Ltd. ・ Plasticizer: Diisononyl phthalate (DINP) ), Manufactured by Shin Nippon Chemical Co., Ltd. ・ Solvent: Isoparaffinic solvent, mineral spirit, manufactured by Nippon Oil Corporation

<Tensile adhesion>
From the results shown in Table 2, the initial for adhesion, in Examples 1-8, 50% strength at elongation is ^{18N / cm 2 ~22N / cm 2} , the maximum tensile strength ^{120N / cm 2 ~150N / cm 2} , The elongation at the maximum elongation was 700% or more, and it was confirmed that the tensile adhesion was excellent.

  With respect to wet heat resistance and heat resistance, in Examples 1 to 8, it was confirmed that the increase in modulus was suppressed, the elongation at the maximum extension was as high as 500% or more, and excellent in tensile adhesiveness.

In contrast, in Comparative Examples 1 to 3, the initial adhesion strength at 50% elongation is ^{15N / cm 2 ~20N / cm 2} , the maximum tensile strength ^{120N / cm 2 ~150N / cm 2} , the maximum elongation It was confirmed that the elongation at time was 800% or more and excellent in tensile adhesion. However, in Comparative Examples 4 and 5, high modulus strength at 50% elongation is at ^{35N / cm 2 ~60N / cm 2} , the maximum tensile strength at ^{160N / cm 2 ~180N / cm 2} , an elongation at maximum extension Was 200% or less, the elongation at the maximum elongation was low, and it was confirmed that the tensile adhesion was inferior. That is, Comparative Example 4 containing no polypropylene polyol (C) and monool (E) having 2 or more functional groups and Comparative Example 5 containing no monool (E) have high strength at 50% elongation. It was unsuitable as a sealing material, and although it was excellent in maximum tensile strength, it was confirmed that it was inferior in elongation at the time of maximum extension.

Moreover, in Comparative Examples 2 and 3, the specimen was melted and could not be measured, and it was confirmed that the heat and heat resistance was poor. In Comparative Example 4, wet heat adhesiveness, 55N / cm ^2, the strength at 50% elongation, ultimate tensile strength of 170N / cm ^2, the maximum elongation when the elongation ratio is 40%, 80 ℃ · 95% RH After wet heat resistance, the change from the initial adhesion is small, but the modulus is high at 55 N / cm ² , the elongation at the maximum extension is low at 40%, and it was confirmed that the strength as a sealing material is unsuitable. . In Comparative Example 5, wet heat adhesive property, the intensity at 50% elongation was 18N / cm ^2, the maximum tensile strength is 150 N / cm ^2, the maximum elongation when the stretch rate is 250%, After 80 ° C. and 95% RH wet heat resistance, the elongation at the maximum elongation is 250% or less and low. That is, Comparative Example 2 containing no castor oil-based polyol (D) having a functional group number of 2 or more and monool (E), and Comparative Example 3 not containing a castor oil-based polyol (D) having 2 or more functional groups It was confirmed that the adhesiveness was poor. Further, Comparative Example 4 containing no polypropylene polyol (C) and monool (E) having 2 or more functional groups and Comparative Example 5 containing no monool (E) are superior in moisture and heat resistance but have a sealing property. It was confirmed that the strength as a material was unsuitable.

Moreover, in Comparative Examples 2 and 3, the specimen was melted and could not be measured, and it was confirmed that the heat resistant adhesiveness was poor. In Comparative Examples 4 and 5, heat adhesion, 50% strength at elongation is ^{25N / cm 2 ~60N / cm 2} , the maximum tensile strength ^{160N / cm 2 ~190N / cm 2} , an elongation at maximum extension is Although the change from the initial adhesiveness after heating at 80 ° C. is small, the modulus is high at 25 N / cm ² or more, and the elongation at the maximum extension is low at 250% or less. That is, Comparative Example 2 containing no castor oil-based polyol (D) and monool (E) having 2 or more functional groups and Comparative Example 3 containing no castor oil-based polyol (D) having 2 or more functional groups are heat resistant adhesives. It was confirmed that it was inferior in sex. In addition, Comparative Example 4 containing no polypropylene polyol (C) and monool (E) having 2 or more functional groups and Comparative Example 5 containing no monool (E) are excellent in heat-resistant adhesiveness, but are sealing materials. It was confirmed that the strength was unsuitable.

<Curing property (tack free time)>
From the results shown in Table 2, it was confirmed that Comparative Example 1 had a tack-free time of 24 hours or longer and was inferior in curability. In Comparative Examples 2 to 5, the tack free time was about 7 hours and was within a predetermined range, and the curability was good. In Examples 1 to 8, the tack-free time was about 2 to 7 hours and was within a predetermined range, and the curability was good. That is, it was confirmed that Comparative Example 1 not containing the latent curing agent (B) was inferior in curability.

<Foaming properties>
From the results shown in Table 2, it was confirmed that Comparative Examples 2 to 5 had good foamability, but Comparative Example 1 was inferior in foamability. It was confirmed that Examples 1-8 had good foamability. That is, it was confirmed that the comparative example 1 which does not contain a latent hardening agent (B) is inferior in foamability.

  Accordingly, the urethane-based prepolymer (A) having an isocyanate group at the terminal obtained by reacting the polyisocyanate and the polyol and the latent curing agent (B), and the polyol is a polypropylene type having two or more functional groups The one-part moisture curable resin composition containing a polyol (C), a castor oil-based polyol (D) having 2 or more functional groups, and a monool (E) is a cured product as compared with a conventional composition. After the heat and humidity resistance, the increase in modulus after heat resistance can be suppressed and the elongation at the maximum extension can be improved. Therefore, the composition of this example is excellent in initial adhesiveness, heat and moisture resistance adhesiveness, heat resistant adhesiveness, suppresses a decrease in elongation and an increase in modulus, and has good foamability and curability. It has been found that a highly reliable one-component moisture curable resin composition can be obtained as a composition such as an adhesive.

Claims (6)

A urethane prepolymer (A) having an isocyanate group at a terminal obtained by reacting a polyisocyanate and a polyol;
A latent curing agent (B),
The polyol contains a polypropylene-based polyol (C) having 2 or more functional groups, a castor oil-based polyol (D) having 2 or more functional groups, and a monool (E) .
Content of the said latent hardening agent (B) is 0.1 mass part or more and 10 weight part or less with respect to 100 mass parts of said urethane prepolymers (A), 1 liquid moisture-curable resin composition characterized by the above-mentioned. object.   The one-component moisture curable resin composition according to claim 1, wherein a content of the castor oil-based polyol (D) is 5% by mass or more and 30% by mass or less in the total amount of the urethane prepolymer (A).   The one-component moisture-curable resin composition according to claim 1 or 2, wherein a content of the monool (E) is 1% by mass or more and 30% by mass or less in the total amount of the urethane prepolymer (A).   The one-component moisture-curable resin composition according to any one of claims 1 to 3, wherein the monool (E) is at least one of a polypropylene-based hydroxyl group-containing compound or a castor oil-based hydroxyl group-containing compound. A sealing material comprising the one-component moisture-curable resin composition according to any one of claims 1 to 4 . An adhesive comprising the one-component moisture-curable resin composition according to any one of claims 1 to 4 .