JPS585370A - Composition for polyurethane coating and adhesive - Google Patents

Abstract

PURPOSE:To provide a compsn. consisting of an isocyanate component having an oxadiazinetrione ring, a polyol component and a tertiary amine or a tertiary phosphine and having excellent film-forming and curing properties. CONSTITUTION:An oxadiazinetrione ring-contg. isocyanate (A) obtained by interaction of poly- or mono-isocyanate (e.g. hexamethylene diisocyanate) and CO2, is made to react with a polyol (B) having at least two active hydrogen atoms and an MW of 62-100,000 (e.g. polyester polyol) in such proportions that the total number of oxadiazinetrione rings and isocyanate groups may be 0.1-10 times as much as that of hydroxyl groups in (B) in the presence of a tertiray amine (e.g. 1,5-diazabicyclo[5,4,0]-5-undecene) or a tertiary phosphine (e.g. triethyl phosphine).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel polyurethane paint/adhesive composition. More specifically, the present invention relates to a multi-component room-temperature curable polyurethane coating/adhesive composition containing an incyanate component having an oxadiazine ion ring, a polyol-μ component, and a tertiary amine or 8th-class phosphine.

Traditionally, polyurethane paints and adhesives have been replaced with other synthetic resin paints and adhesives.
Chemical and stain resistant compared to adhesives.

It has excellent properties in terms of adhesion, gloss, and abrasion resistance, and is used in woodworking, metals, roof tiles, concrete), and defmetics. It is used in a wide range of applications, including rubber and paper.

These polyurethane paint/adhesive compositions include -
Multi-component types such as a liquid type and a two-part type have been proposed, and the two-part type usually consists of a polyol-μ component as a main ingredient and a polyfunctional 19 isoV analyte component as a curing agent. The curing agent for keratin is usually made from diiso V-anate, which is then used as a polyol.

Urethane and urea are produced by reacting with water, amines, etc.

Polyisocyanates having biuret bonds and the like are derived, and polyisocyanate having an isocyanufut ring is obtained by performing a trimerization reaction using a catalyst. However, the content of iso-V anor-F in such derivatives is much lower than that of the raw material diiso-v-ana-F, and therefore a large amount of curing agent is required relative to the base polyop-p. Since curing agents are more expensive than the base resin, there is a demand for curing agents that can be cured even in small amounts. In addition, all of these derivatives have high viscosity,
In order to use it as a hardening agent, it is necessary to dilute it with a solvent, etc., and from the viewpoint of saving resources and preventing paper separation, it is desired that a hardening agent with a high solid content or a solvent-free type be developed. Furthermore, urethane paints and adhesives that cure at room temperature generally require a long time to completely cure the coated material, so they have drawbacks such as poor workability.

The present inventors discovered that the allophanate production reaction from an oxadiazinetrione ring and a hydroxyl compound proceeds easily even at room temperature in the presence of a tertiary amine or tertiary phosphine. As a result of extensive research in order to use the isocyanate component having an oxadiazinetrione ring as a curing agent, we used it and the polyol-μ component as a curing agent in the presence of an 8th class amine or a primary phosphine. React with the paint.

When used as an adhesive, only a small amount of curing agent is required, and it can be used as a high solids or solvent-free curing agent, and has superior curing properties compared to conventional V-tan type curing agents. Knowing that the above-mentioned problems such as The present invention relates to a multi-component room temperature curable polyurethane paint/adhesive composition containing an 8th class phosphine.

The isocyanate component having an oxadiazinetrione ring used in the present invention refers to a compound having both an oxadiazinetrione ring and an isocyanate group in the molecule. As a method for synthesizing such a compound, it is specifically convenient to use a reaction between an isocyanate and an elemental dioxide.

Such isocyanates include aliphatic and alicyclic isocyanates.

Examples include araliphatic isocyanates, such as tetotumethylene diisocyanate, hexamethylene diisocyanate, and hexamethylene diisocyanate.
anato, tr, ;-diisoVana)dipropyl ether, 2,6-diisoVanatocaderonic acid esd/l/,
to L11-) liiso V anatomoundecane, bis(isolyanatomethy~)3/chlorohexane, bis(isocyanate group A/)$/chlorohexane, 1-isocyana)-8-
Isocyana Y Methyl & Methyfi-11 Talohexane, Bis(4-isoV ana)V talohedane y*) methane, etc.V9 DiisoV anaF, Bis(3-isocyanato group β)benzene IliisoV anasis are preferably used. These polyisoV-anates may be used alone or in mixtures with each other, such as monoiso-V-anates, such as methyl-iso-V-anate, ethyl-iso-V-anate, Il-buty-μ-iso-V-anate, j −
Kuro μheki Yfi/Iso V Ana-), V Talohex F/L
It can also be used as a mixture with /iyvana-Y, VterhekiVfi/methiμisoVanate, bendipisoVanorF, feuethylisoVanate, and the like.

The reaction between isocyanate and sulfur dioxide is carried out in the presence of a sulfur compound. As a catalyst, gS-class phosphines, chloride compounds, and 1-nitroquinones can be used.
Class phosphines are effective. IsoV with a diazinesilion ring that is oxidized by the reaction of isoY anate and fluorine dioxide
When Ana-F can be obtained, it can be used as the isocyanate component of the present invention, but usually various metal compounds are added to stop the reaction and to preserve the product stably beforehand. It is preferable to use an alkylating agent, a S/A/forming agent, an acid, and an esthetic agent as a stabilizer to stop the reaction.
/@conductors, pheno-μ, peroxides, sulfur, polysulfides, metal sulfites, halogens, etc. can be used. In particular, the isocyanate component having nine oxadiazinetrione rings and an additive selected from peroxide, iot, polysulfite, metal sulfite, and halogen is an isocyanate component having nine oxadiazinetrione rings and This is preferable from the viewpoint that the reaction between the isoV (ana-) and the I-Rio-μ component Qk-Droki-V group proceeds smoothly.

A lifting platform for synthesizing an incyanate component having a diazinetrione ring to be oxidized from *9, 19 iso V an-) and * element dioxide, 4! So Iso V Ana (and Po J O μ
Compounds (e.g., ethyl V glycol μ, propy V glycol μ, 44-butane V oh μ, gusoserine, trimethylo-μ propane.

Polyether μ Poly-P, Polyester Poly-P, Acrylic μ-Poly-P, Emeki V-Poli-P, etc.) or polyamine compounds (e.g., ethylene diamine, hexyl methane diamine, phenylene diamine, polyether polyamine, polyamide polyamine, etc.) in NC4. An adduct having terminal NC0J& obtained by reacting in excess can also be used as polyisoV Ana-F. In addition, 4M can be used in which a part of Boy Sonoanato 0NCO is blocked with a blocking agent, and in addition, these) lic.

Dimerized or octamerized groups can also be used in the same way.

Further, isocyaner l having an oxadiazinetrione ring obtained by the reaction of polyiso V anate and dioxylic acid gas.
can be used after being adducted, pulled, or multimerized as described above.Additionally, addition, blocking, or multimerization reactions can also be carried out simultaneously when synthesizing the oxadiazinetrione ring. The above adduct and plotter body are synthesized by Kubetsu.

Among the isoleanate components having an oxadiazinetrione ring of the present invention as described above, hexamethylene diisonoanate,! -IsoV Ana(-3-IsoV Anatomethiμm11.
&@-) Rimethy~V talihexane or bis(isoV
AnaF-MethiIV)V Those derived from chlorohexane provide particularly excellent properties in terms of coating performance and curability.

K, in which an isoleanate component having an oxadiazinetrione ring is used as a curing agent, is preferably one in which the number of flat functional groups in one molecule, including the oxadiazinetrione ring and isoV anato group, is about 10 to 10. , l which is the main ingredient
! Structure such as the number of functional groups of the OH μ component, OH value 0 molecular weight, etc.
It is determined as appropriate depending on the physical properties of the target coating material, the molecular structure of the curing agent, etc. If the above-mentioned isoVanate component having an oxadiazinetrione ring contains an isoleanate-enriched substrate with low productivity, etc., and is not suitable for use as a curing agent as it is, steaming 11. 〉 monomer by extraction, crystallization and other suitable methods.

It is also possible to remove the artificial substrate. The isoV anor F component having nine oxadiazinetrione rings obtained in this way may be used as a curing agent or not, but if necessary, it may be diluted with an organic solvent, V-coating agent, etc. Of course, it is also possible to make nine pure states suitable for use.

The d9 oh μ component that can be used in the present invention contains at least 4s active hydrogens and has a molecular weight of 1! ~10
Examples include OO-, preferably 4-oN6oI...O metal compounds. ) Preferably Ilc! in one molecule. Polio-p having ~6· OX doloki Vμ groups and a molecular weight of @HU@· is used. Metal compounds containing hydroxyl/II/N groups, amino groups,
It may also be a metal compound containing a functional group having active hydrogen such as a thiol group.

More specifically, polyester μ poly-O μ, polyether poly-μ, polyether-S-D poly-O-, dIl
Preferably, ester μamide polyol-μ, acrylic μll-oμ, polyurethane polyol) engineering V polyol μ, ebok V modified polyol-μ, dI rehydroki V-acane, oil-modified polyop-p, castor oil, or mixtures thereof are used. can do.

Examples of such polyethers include polyhydric alcohols.
Examples include μ and y features of polybasic acids. Examples of polyhydric alcohols include ethylene glycol) propylene glycol, buty V glycol μ, hex V lene glycol μ,
Neopentyl glyco-μ, V chlorohexanedimethanol #
diethylene glycol,)
Examples include l-lyethyl glycol, dipropylene glyco-μ, polyoxypropylene glycol*, dlyoxy-v butylene glyco-μ, glycerol μ, trimethyl-propane, pentaerythri F-μ, and so-ρ biF-.

Examples of polybasic acids include succinic acid, adipic acid, azefinic acid, and sepa-V acid.

Phthaμ acid, isophthaμ acid, terephtha! acid, tetofhydrophthaμ acid, hexahydroph! μ acid! Examples include leic acid, fumaric acid, and their acid anhydrides. In addition, 1-reste μ polyol obtained by ring-opening heavy metals such as Kabutotan and methyl caprotaton with glyco-fi/lk is also a suitable example.

Examples include ethyl oxide, propylene oxide, butylene oxide, tetophhydrofuran, styrene oxide, epichlorohydrin, fluoride 9v dylethe, aliμgurifi/ether, etc. The epoxide compounds can be prepared by reacting them with heavy metals in the presence of a catalyst such as boron trifluoride, or by adding these epoxide compounds, alone or in mixtures, alternately to a reactive hydrogen atom-containing initiator. can. Examples of the reactive hydrogen atom-containing initiator include water, ethyl glycol, propylene glyco-μ
, glyceryl μ, trimethylo μ propane, pentaerythritol, polyols such as soμ propane, aminoalcohols such as ethanolamine, and polyamines such as ethylenediamine.

Examples of polyolefins include those obtained by subjecting polyesterification reaction of the polybasic acid to polyesterification using the above-mentioned polyadene as a raw material, as well as ring-opening compounds of epoxide compounds and acid anhydrides. It is possible to contain both polyate μ and llieste μ segments in one molecule obtained by the polymerization reaction.

Examples of polyester polymers used in the above-mentioned polyester μ conversion reaction include ethylamine, propylene diamine, hexamethylene diamine, and chloride.
It can be obtained by using together raw materials having an amino group, such as hydrogenated diamine, hydrogenated diamine, ethanol-μ amine, and propano-μ amine.

Hitoriki ViL/generally known as Akurimubo J-op
The group-containing polymer can be synthesized by copolymerizing a polymerizable 7-mer containing one or more 7-groups per molecule and another polymer copolymerizable with it. As a hydroxyl Vμ group-containing polymer, for example, 9μ acid, doro-IF ethyl, atariμ acid hydroxy sr.
f abiμ, atarip acid, dorokiVbutiμ, trimethyμpropaneacryμ acid (no ester, corresponding metatariμ acid derivatives, II!rehydrochloride, μkuma VneyF, fumarate, etc.) Examples of copolymerizable monomers include acrylic acid and its methyl p
, Echi μ, Propi A/, Buchi μ,! -ethy~hexvpesterp, methacrylic acid, maleic acid, thumaic acid, itaconic acid and their corresponding esters above, such as styrene, α-methylstyrene, vinyl acetate) acrylonitrile! , metatarlonite 9fi7, and other vinyl monomers.

As the polyol, for example, a reaction product of a polyol and 1-liiso-V ana-) having a hydroxy-V group at the end can be used. Examples of polio-μ include ethylene glycol-μ, propylene glycol, buty-V
Glyco-μ, hexyv daliko-μ, neopentyμ glyco-μ, V talohexane dimethanol μ, diethylene glyco-μ,) lyethylene glycol μ, dipropylene glyco-μ, g9-ka-py,) 9 methyl- to propane.

Examples include polio-μ such as bentaerythrito fi/, soμ pitot μ, or polymer polio-μ such as polyester μ polyol, polyester μ ether μ polyol, and polyester μ polyol such as It will be done. Examples of the 1-diiso-V-anate include tetofumethylene-diiso-V-anate and hexamethylene-diiso-V-anate.

Bird 6-diisoV anatomethyfi/caproate, s-isoV anatomethy-&4-)rimethypyytalohex V
fi/isoV anato, 44'-methylenobis(F chlorohexyHisoV anato), 11- or L4-bis(isoV anatomethypy) v talohexane, methylcyclohexane-milk 4-diisoV anasi, 0- or p
-Phenylene diiso V-anate, diphenylene μmethane-4
4'-diiso-V anate, λ4-1 or &6-tri-V-iso-V-anate, LI- or L4-di-iso-V-anate, or one of these polyiso-V-anates
Polyiso-V annates such as mercury and mercury can be used. 4! 9 Part of the above polyol: ethyl diamine, propylene diamine, hequinamethylene diamine, lylene diamine, bisaminomethy, A/I' clohexane, --aminomethy*-&&l-)rimethyμV
Chloheki Vfi/Amine.

49 flv
It can be used as an in-I Rio μ.

Examples of epoxy resins include condensed epoxy V resins obtained by reacting polyphenol compounds or their hydrogenated products with Ebiku Aμ Seven Tone), t
In addition to this, it is also possible to use epoxy V ester A/resin obtained by reacting nine fatty acids with engineered dlF resin, and modified epoxy V resin obtained by reacting with a~k~μ amine. . Examples of 19-oxy-V-acane include saponified products of vinyl acetate single heavy metal bodies or copolymers with other co-heavy metal polymers having ethylene bonds, or polybutadiene polyol*&. can give.

Furthermore, the nine compounds mentioned so far with relatively large molecular weights of 11'& 2000, A/0-), and 6! ~4
Low molecular weight polio-μ having a molecular weight in the range of 0.00 to 0.00 can be used alone or in combination. These low molecular weight polyolefins include, for example, ethyl V glycol μ, pripy V glycol μ, butylene glycol, hex V V glycol! , neoplier μ glyco-μ, V-cryhexane dimethanol μ.

Examples include glycerol) trimethylo-μ propane, pentaerythritol, diethylene glycol-μ,) lyethylene glycol lv, diderovy V glycol fi/, and the like.

The convenient ratio of the isoV anal) component having an oxadiazine silion ring and the polyol-y component is such that the sum of the number of oxadiazine silion rings and the number of isoV anal) groups is relative to the number of hydroxyl groups in the polyol-μ component. It is better to have an IC between 1 and 10 (0), more preferably between a6 and 8.When used as a paint, it is usually between 4 and 6, preferably between 6 and 8.
It is better to set it to L4.

The tertiary amine of the present invention includes aromatic and aliphatic tertiary amines, and aliphatic tertiary amines are preferably used. Aliphatic tertiary amines include chain and cyclic amines, and polyamines such as Vcy amines and triamines are used. Among such amines, preferable examples of 4110 include azabi compounds, chain polyamines, and cyclic cenoamines.

Some cyclic polyamines are used, and these amines are, for example, in the general formula 1! , 1' represents the alkylene group of Atsushi Hiromoto 1 to 6] In formula 1, 11=- represents a lower Al &/K μ group which may be substituted with a lower A μ co-V, respectively. , the lower alkylene group, -1'-N11L4-(W
is lower alkylene;
: Indicates NH, t, 11 and wings 2 or 13 and 14
Combined with lower grade A, IIL/Year Shin.

-1'-0-1'- (V has the same meaning as above) or -t'
-N1g -r- (*' has the same meaning as above, R6 is 1!1
= 14) may be formed]1
[In the formula, "IJ2-R8 represents a lower a[mu]kyl group which may be substituted with dolokiV[mu] or lower ay:1[k], respectively." [shown] is a lower alkyl μ optionally substituted with a lower alkyl V
This includes tertiary amines represented by:

Specifically, particularly preferred amines include, for example, Ls-
DiazabicycloC5,4,03-5-Undecene Nakazumi-Diazabicyclo[4Kame・)-5-/Azabicyclocarbons such as Nene, N, N, N- to'-tetofumethi! Ethylenediamine, N,N)c,w-tetofumethyj%/-L・-hexanediamine, NJi-bis(todimethylaminoethyl, A/)methylamine, N-(!-
Dimethyμaminoethyμ)morpholine, N-methyμmN'
-(x-dimethy~aminoethyl/L/) bibefudin, M
, 14. Chain-like and partially cyclic polyamines such as W-trimethy~-N'-(!-hydroxyVethyA/)ethylenediamine, bis<s-pmethylaminoethoxyy)methane, and teFwomethyμguanidine.

Examples include cyclic amino acids such as chimetacidine, N-meVapkin, N-alkylpiperidine, and alkylated derivatives thereof. When the above-mentioned aliphatic amine is used as a catalyst, although the pot life after mixing each component is relatively long, the curing properties of the coated product at room temperature are particularly excellent, and the coating If a little forced drying is performed afterwards, the coating will have even better curability. Furthermore, the cured product exhibits particularly excellent weather resistance, gloss, water resistance, and adhesive properties. 9. The above-mentioned tertiary amines, organic acids, amino acids, and inorganic acids can also be used.

As the 8th-class phosphine of the present invention, aromatic and aliphatic tertiary phosphines are used, such as triethylphosphine, Tri-Otori-Petitμ phosphine, dimethylphenylphosphine, triphenyμphosphine, diethyl/L/
V Chloheki Vfi/phosphine, 1-ethylphosphorane. 1---Petit μ phosphorinane, L4-diphosfabi V
Kuro [λλ friend] Octane,) Squirrel (Hydroki V Echiμ)
Phosphine, etc. can be removed.

The above-mentioned tertiary amine and tertiary phosphine act as a reaction catalyst between the isocyanate component having an oxadiazinetrione ring and the polyol-μ component, and the amount used is arbitrary depending on the type of base agent, curing agent, curing conditions, etc. However, it is usually about a@01 to 10, preferably about a0 to about 6,000, based on the weight of the solid content in the base agent and curing agent.

In addition, in order to carry out the reaction of the oxadiazinetrione ring, it is sufficient to add the above-mentioned primary amine and 8th class phosphine, but for the purpose of adjusting the reactivity of the NCO group in the curing agent, tin, lead, nickel, etc. Zinc, titanium, antimony, iron, cobalt, bismuth, uranium, cadmium, aluminum,
It is also effective to add compounds that adjust the degree of reaction between the known 0NCO group and OHJ&, such as vanadium, mercury, potassium, fluorium, diμconium, and other O metal organic compounds, organic acid salts, and inorganic compounds. In addition, pigments, leveling agents, antifoaming agents, anti-sagging agents, etc. can be used as appropriate.

The composition of the present invention obtained in this way is usually used as a so-called two-part type consisting of an isocyanate component having an oxdiazinetrione ring and a polyol component.
Both components are mixed during final use. At this time, the tertiary amine and tertiary phosphine may be mixed with either the isocyanate component or the polyol-μ component, but in order to prevent deterioration of the isocyanate component, they should be mixed with the polyol-μ component. It is preferable to keep it. First, dissolve the amine and phosphine alone in a solvent together with a leveling agent, etc. When using the solution, add the isoV annate component,
It can also be used as a so-called three-part type, which is mixed with a polyol component. When the composition of the present invention is actually used, each component is mixed as is or in the form of a solution, and the mixture is applied to a painted or adhesive surface and cured at room temperature.

The composition of the present invention is useful for painting and adhering wood, iron, metals such as aluminum, plastics, rubber, paper, summer, concrete, etc. The composition of the present invention requires only a small amount of curing agent to be used, about "A" to "A", compared to conventional urethane-based curing agents. Furthermore, since the curing agent has a low viscosity, it can be used as a solvent-free paint adhesive or a paint adhesive with a high solids content. Furthermore, the pot life during mixing is relatively long.
However, the curability of the coated material is good. In particular, it has the characteristic that a practically excellent cured product can be obtained by coating, applying some force, and drying (@0-110' x 110-go minutes). Furthermore, the resulting coating film has excellent weather resistance and is attractive to the eye.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.

Reference example 1 Hexamethylene diiso V ana-) 841F to 4f
While blowing carbon dioxide gas with JC, add Tory Dew-Petit μ phosphine Lllf and carry out the reaction for 6 hours while stirring. Stop the supply of 9th acid gas, add sulfur powder a, and stir for 80 minutes, then cool. friend. When this raw material was removed using a horizontal film evaporator, a pale yellow slightly viscous liquid mf was obtained. This C) also has a tiNco content of 4 to 8 cm, an oxadiazine trione content of @77 Wam'/'t, and a residual hair tsum amount of A4.

Reference creativity Hatake-bis (isocyanatomethylic Vri-1-lohexane)
Tory-Petit μ phosphine sot was added to the if at 10° C. while blowing carbon dioxide gas, and the reaction was carried out for 6 hours while stirring. The supply of carbon dioxide gas was replaced with nitrogen, and Peroxide Pency and A/Kame 8f were added and stirred for 80 minutes. The raw material is removed by evaporation of the product using a thin film evaporator, and a pale yellow viscous liquid 180f is obtained, fF4, which has an NCO content of ts.
sm/Vt oxadiazine) ion content z2P is the amount of residual monomer (LSI).

Reference example 8 λ8-bis(isocyanatomethyl)V chlorohexane 19
A reaction was carried out for 8 hours in the same manner as in the reference invention using 4F and Tory Otori-Petit μ phosphine got, and
/λ6f to stop the reaction and transfer the teacher's material to F〃en10
・-, n-hexane 500- was added thereto, and the solvent layer was removed by shaking well. After repeating this extraction operation eight times, acetic acid butylene chloride was added to the extraction residue to obtain a solution with a non-volatile content of 85%. This tooONCO food amount is tSOsan VtmOxadiazinetrione content is 11℃m
IIIVf.

Example 1 Iso V ananate component 16f obtained in Reference Example 1 was added to Acrylic μ Polyol μ Acriditor A-Hatago
After mixing with non-volatile fraction OX (manufactured by Dainippon Ink Chemical) 6af1t, it can be diluted with a mixed solvent of F〃eneacetic acid butylene　 and #' acid celloprop, and this can be used as a tattoo diazabicyclo [Kan 403-6- After adding and mixing 110 sv of undecene formate as a lOx isopropanol solution, the mixture was spray-painted onto a mild steel plate to obtain a coating film with a film thickness of fIOμ.

Table 1 shows the physical properties of the coating film when it was left at room temperature for days. As a comparative example, Dehata Funate N (F form of Hesamethylene diiso V Ana-F, amine equivalent 8, Hatake,
Non-volatile content: 86%, manufactured by Asahi Kasei Industries, Ltd.) 1-T and Acrydatum-850st, @t were mixed, diluted with the above f# rope, and coated with Subv-V. The physical properties of the coating film are also shown.

Table 1 Example 2 After dissolving the isoV anor F component obtained in the reference invention in ~10 t of butylacetate, polyester polyol-μ
Takewotsuta → '1 (OR value 14 J, non-volatile content 6 ml, manufactured by Takeda Pharmaceutical Co., Ltd.) Mixed with 61 〒f, and further) µ-dibutylene acetate µ.

It was diluted with a mixed solvent of cellosolve acetate. Add this to N, ml
,)r-)rimethiμ-N-(hydroxyVethiμ)ethiV
7 diamine sO@Misaki and diptyltin difluoride) 1
Add and mix each toluene solution of q, and after 9 minutes, spray paint on a mild steel plate and apply llI! ! I about 6 @PO! ! ! A membrane was obtained. Table 2 shows the physical properties of the coating film when it was left at room temperature for a few minutes. As a comparative example, Takenate 1! Om(1,1
-Bis(isocyanatomethylμ)S/Chloe IF↑n)
Rimethylo-propane adduct, amine equivalent Isma, non-volatile fraction S, Takeda Pharmaceutical) set and Tagawotsuta 17
Table 8 shows the physical properties of the coatings that can be mixed and diluted with -II ILlF.Examples Hot Reference Examples Synthesis of methyμ metataryl F, hydroxyl V ethyl acrylate, ethyl acrylate, buty μ metataryl F, molecular weight approx.
oo on@so.

Non-volatile content 110) was mixed with each of the catalysts shown in Table 8, and the mixture was coated on a glass plate.
Solvent resistance test (ethyl acetate μ Lavinda) on fresh vegetables dried at 80°C for 30 minutes and those left at room temperature for S days.
was carried out.

Also, the same sample was coated on release paper to form a film, dried and left under the above conditions! Spectrum ~ was measured, and the amount of disappearance of NCO group 016 Steel-1) and oxydiazinetrione group 01-5C1) was determined.As a comparative example, Takenate D-1! The same tests are also carried out on coatings and films obtained similarly from ON 1alt and the above-mentioned AgμPolio-/1150f. The results are shown in Table 8.

Table 8 DIIU: 1,5-diazabicyclo(ri, 4.
o) -r-Kunten Example 4 10 tons of the incyanate component obtained in Reference Example 1 was mixed with polyester polyol Takelac A-606 (OH value 40.
After mixing with 200 t of non-volatile matter (601 G, manufactured by Kurade Yakuhin Kogyo), it was diluted with 300 y of ethyl acetate.

0.13F of 1,5-diazabicyclo(5,4,0-5-undecene) was added and mixed, and this was applied to a nylon film, dried, and a polypropylene film was attached.The amount of coating was 3.5'/ , = closed.

After the bonded film was left at 40° C. for S days, the adhesive strength was measured and found to be 1ooo715□.

Claims (1)

[Claims] A multi-component room-temperature curable polyurethane paint/adhesive composition comprising an isoV anate component having an oxtsF azine Y lyon ring, a polyol component, and an 8th class amine and an 8th class phosphine.