CN1995256A - Bottom agent-free type single component moisture-curing polyurethane adhesive - Google Patents
Bottom agent-free type single component moisture-curing polyurethane adhesive Download PDFInfo
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- CN1995256A CN1995256A CN 200510132670 CN200510132670A CN1995256A CN 1995256 A CN1995256 A CN 1995256A CN 200510132670 CN200510132670 CN 200510132670 CN 200510132670 A CN200510132670 A CN 200510132670A CN 1995256 A CN1995256 A CN 1995256A
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- diisocyanate
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Abstract
The invention discloses a base agent-free single-component wet solidifying polyurethane binder, which is reacted by the following parts: polyurethane prepolymer, binding accelerant, 2,2-dimorphia diethyl ester and tin dibutyl dilaurate catalyst, elasticizer, fill, ultraviolet absorbent and stabilizer, wherein the single-component polyurethane binder possesses excellent binding property for binding and assembling automobile and other vehicle.
Description
Technical field
The present invention relates to a kind of single component, moisture curing, exempt from end formulation polyurethane adhesive and preparation method thereof.This bottom agent-free type single component moisture-curing polyurethane adhesive possesses outstanding adhesiveproperties to the glass of painted steel sheet and band ceramic coating, can be used for industrial circles such as automobile industry, railway transportation, freight container manufacturing, device fabrication, air-conditioning and ventilation plant, especially be fit to the vehicle window and the windshield assembling of vehicle.
Background technology
In the vehicle window and windshield assembly technology of automobile and other vehicles, generally adopt with the single-component moisture curing polyurethane caking agent of polyurethane prepolymer at present as main component.Polyurethane prepolymer wherein is to be generated by polyol compound and excessive isocyanic ester and polymer reaction thereof, and the prepolymer molecule is with the isocyanate groups end-blocking.
The general glass assembly technology that adopts is edge or the car body sash frame surface that polyurethane adhesive is coated in glass, then glass cementation to car body.In this bonding process, end agent is absolutely necessary usually, promptly must treat bonding surface and carry out end agent pre-treatment before the polyurethane coating caking agent.General end agent is to be the black liquor of main component with the polyisocyanate compounds, the time very easily pollutes the vehicle body finish paint in assembling, and as a procedure of bonding process, has increased the difficulty of using.So in the glass assembling process, bottom agent-free type single component moisture-curing polyurethane adhesive is popular.Yet, some are scribbled the steel plate of anti-acid rain lacquer, high solids content lacquer and easy maintenance paint, if be not very difficult by end agent.
Summary of the invention
According to top situation, the purpose of this invention is to provide a kind of single-component moisture curing polyurethane caking agent, improve it not by the adhesiveproperties of end agent.Found that, add special catalyzer and adhesion promoters, can make the single-component moisture curing polyurethane caking agent that painted steel sheet is possessed good adhesiveproperties.
The invention provides a kind of single-component moisture curing polyurethane caking agent, its main component is a polyurethane prepolymer, and:
(1) affixture of silane coupling agent and polyurethane prepolymer is as adhesion promoters
(2) 2,2 two morphine quinoline diethyl esters and dibutyltin dilaurate are as catalyzer
Single-component moisture curing polyurethane caking agent of the present invention with isocyanate-terminated polyurethane prepolymer as main component, the preparation of prepolymer can be by traditional method preparation, it is polyol compound and excessive isocyanate compound reaction, OH/NCO=1/1.3～1/5 usually.
Above-mentioned polyol compound comprises: polyether glycol, as the polyoxytrimethylene polyvalent alcohol; Modified polyether polylol; Polyester polyol is as condensation polyester polyol, open loop polyester polyol, polycarbonate diol; Other main chains contain the terminal hydroxy group compound of C-C.
Above-mentioned isocyanate compound comprises tolylene diisocyanate, diphenylmethanediisocyanate, 1, hexamethylene-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, naphthalene-1,5-vulcabond, Methylcyclohexyl diisocyanate or the like.
In the single-component moisture curing polyurethane caking agent of the present invention, contain above-mentioned isocyanate-terminated polyurethane prepolymer, the content of prepolymer is the 25%-65% of total mass part.
In the single-component moisture curing polyurethane caking agent of the present invention, except containing isocyanate-terminated polyurethane prepolymer, the affixture that also contains silane coupling agent and polyurethane prepolymer is as adhesion promoters.The affixture of silane coupling agent and polyurethane prepolymer is the 0.5%-10% of total mass part as the content of adhesion promoters in the single-component moisture curing polyurethane caking agent
Above-mentioned silane coupling agent comprises gamma-methyl allyl acyloxypropyl trimethoxysilane, mercapto alkylalkoxy silane, N-(β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan, phenyl alcoxyl yl alkyl alkoxy silane, γ-glycidyl ether oxygen propyl trimethoxy silicane, γ-An Bingjisanjiayangjiguiwan, allyltrimethoxysilanis, isocyanate group propyl trimethoxy silicane, isocyanate group propyl-triethoxysilicane etc.Silane coupling agent preferably is mercaptopropyl trimethoxysilane, mercapto propyl group methyl dimethoxysilane, phenylamino propyl trimethoxy silicane, isocyanate group propyl trimethoxy silicane.
The above-mentioned polyurethane prepolymer as adhesion promoters is a tolylene diisocyanate, diphenylmethanediisocyanate, 1, hexamethylene-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, naphthalene-1, the 5-vulcabond, the dimer of Methylcyclohexyl diisocyanate etc., tripolymer and with TriMethylolPropane(TMP) affixture etc.What be more suitable for is the hexamethylene diisocyanate derivative.Described hexamethylene diisocyanate derivative comprises biuret derivatives, hexamethylene diisocyanate tripolymer, hexamethylene diisocyanate and TriMethylolPropane(TMP) affixture etc.
In the single-component moisture curing polyurethane caking agent of the present invention, except containing isocyanate-terminated polyurethane prepolymer, adhesion promoters, also contain 2,2 two morphine quinoline diethyl esters and dibutyltin dilaurate as catalyzer.The content of 2,2 two morphine quinoline diethyl esters is the 0.05%-1.5% of total mass part, and the content of dibutyltin dilaurate is the 0.001%-0.5% of total mass part.
In the single-component moisture curing polyurethane caking agent of the present invention, except containing polyurethane prepolymer, adhesion promoters, catalyzer, also contain softening agent, filler, solvent, UV light absorber, ultra-violet stabilizer etc.
Above-mentioned softening agent is phthalate, alkyl sulfonates, tritolyl phosphate, clorafin etc.As dibutyl phthalate, diisononyl phthalate, dioctyl phthalate (DOP), Di Iso Decyl Phthalate etc.Softening agent is the 5%-50% of total mass part at the content of single-component moisture curing polyurethane caking agent
Above-mentioned filler comprises calcium oxide, silicon powder, carbon black, talcum powder, titanium dioxide, lime carbonate, kaolin or the like.Filler is the 10%-60% of total mass part at the content of single-component moisture curing polyurethane caking agent.
Above-mentioned solvent comprises toluene, dimethylbenzene, kerosene etc.Solvent is the 0%-20% of total mass part at the content of single-component moisture curing polyurethane caking agent.
Above-mentioned UV light absorber comprises salicylate class, benzophenone class, benzotriazole category, group-substituted acrylonitrile, triazines etc.The special company of cyanogen product for example: UV-3638, UV-2337, UV-5365, UV-5411, UV-24, UV-531, UV-9, UV-1084, UV-1164 etc.; Ciba produces brilliant: Tinuvin P, Tinuvin 1130, Tinuvin 99-2, Tinuvin 928, Tinuvin 326, Tinuvin 327, Tinuvin 329 etc.UV light absorber is the 0.1%-2.0% of total mass part at the content of single-component moisture curing polyurethane caking agent.
Above-mentioned ultra-violet stabilizer generally is a hindered amine light stabilizer.The special company of cyanogen product for example: UV-3346, UV-3529, UV-3581, UV-3853, UV-3853S, UV-2908 etc.; Ciba product: Tinuvin 770, Tinuvin 292, Tinuvin 5050, Tinuvin 5055, Tinuvin 5151, Tinuvin 5060 etc.Ultra-violet stabilizer is the 0.1%-2.0% of total mass part at the content of single-component moisture curing polyurethane caking agent.
The preparation method of single-component moisture curing polyurethane caking agent of the present invention is:
After at room temperature order added polyurethane prepolymer, softening agent, solvent, adhesion promoters, catalyzer, UV light absorber and UV stabilizer in stirring tank, blend was 30～45 minutes under vacuum protection, and thoroughly mixing gets final product.
Embodiment
More specifically the present invention is made description now with reference to embodiment and the comparative example that is used for comparison, but be not limited to this.Unless add explanation in addition, otherwise " part " among the embodiment all is meant weight part.
Embodiment 1
Polyurethane prepolymer is prepared as follows:
Polyoxytrimethylene dibasic alcohol 385 grams (molecular-weight average 2000) and polyoxytrimethylene trivalent alcohol 560 grams (molecular-weight average 4500) join in the reactor that has mechanical stirring, nitrogen protection and heating unit.Under nitrogen protection, said mixture is heated to 50 ℃, add 160 gram diphenylmethanediisocyanates then, 10 gram tolylene diisocyanates stir, and add 0.1 gram dibutyltin dilaurate, stir 2h and get final product.
The preparation method of adhesion promoters is as follows:
Mercaptopropyl trimethoxysilane 100 grams mix with hexamethylene diisocyanate tripolymer 100 grams, and room temperature reaction 48h gets final product.
The preparation method of single-component moisture curing polyurethane caking agent is:
At room temperature order adds polyurethane prepolymer 400 grams, adhesion promoters 50g, dioctyl phthalate (DOP) 200 grams, dry carbon black 450 grams, dibutyltin dilaurate 2 grams, 2 in stirring tank; behind 2 two morphine quinoline diethyl esters, 4 grams, Tinuvin 327 UV light absorber 5 grams, Tinuvin770 ultra-violet stabilizer 5 grams; under vacuum protection, mix, obtain having thixotropic single-component moisture curing polyurethane caking agent.
Embodiment 2
Except mercaptopropyl trimethoxysilane being replaced with the phenylamino propyl trimethoxy silicane, repeat similar step, and obtain the single-component moisture curing polyurethane caking agent as embodiment 1.
The comparative example 1
Except not adding the adhesion promoters, repeat similar step, and obtain the single-component moisture curing polyurethane caking agent as embodiment 1.
The comparative example 2
Except not adding outside 2, the 2 two morphine quinoline diethyl esters, repeat similar step, and obtain the single-component moisture curing polyurethane caking agent as embodiment 1.
The single-component moisture curing polyurethane caking agent that evaluation obtains in embodiment 1, embodiment 2 and comparative example 1 and comparative example 2 is not by the adhesiveproperties under any end agent situation.The adhesiveproperties characterizing method is as follows:
Above-mentioned single-component moisture curing polyurethane caking agent is extruded into the triangle bar shaped on following japanning steel disc surface, flattens, and 3 millimeters of thickness, 20 ℃ and 65% humidity condition solidify 168h down, cut stripping test by cutter and estimate adhesiveproperties.Embodiment 1,2 and comparative example 1,2 the results are shown in table 1.
Table 1
| Embodiment | The comparative example | |||
| 1 | 2 | 1 | 2 | |
| Anti-acid rain lacquer high solids content lacquer | CF100 CF100 | CF100 CF100 | AF100 AF60 | CF100 AF60 |
| Easy maintenance paint | CF100 | CF100 | AF100 | CF100 |
CF: the cohesive failure rate, represent with area percentage (%) in the table.
AF: the interfacial failure rate, represent with area percentage (%) in the table.
Can find out significantly that from the result of table 1 single-component moisture curing polyurethane caking agent of the present invention (embodiment 1,2) is not possessing excellent adhesiveproperties under the situation by end agent.
Claims (5)
1, a kind of bottom agent-free type single component moisture-curing polyurethane adhesive, it is characterized in that containing polyurethane prepolymer, adhesion promoters and 2,2 two morphine quinoline diethyl esters and dibutyltin dilaurate catalyzer under the situation by end agent not, have outstanding adhesiveproperties to painted steel sheet.
2, single-component moisture curing polyurethane caking agent as claimed in claim 1 is characterized in that the base polyurethane prepolymer for use as based on polyol compound and the preparation of excessive isocyanate compound.Described isocyanic ester is a tolylene diisocyanate, diphenylmethanediisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, naphthalene-1,5-vulcabond, Methylcyclohexyl diisocyanate etc.Described polyol compound comprises: polyether glycol, as the polyoxytrimethylene polyvalent alcohol; Modified polyether polylol; Polyester polyol is as condensation polyester polyol, open loop polyester polyol, polycarbonate diol; Other main chains contain the terminal hydroxy group compound of C-C.
3, single-component moisture curing polyurethane caking agent as claimed in claim 1, it is characterized in that reaction product with silane coupling agent and isocyanate derivates as adhesion promoters, described silane coupling agent is meant γ-Qiu Jibingjisanjiayangjiguiwan, N-(β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan, γ-glycidyl ether oxygen propyl trimethoxy silicane, γ-An Bingjisanjiayangjiguiwan, gamma-methyl allyl acyloxypropyl trimethoxysilane etc.Described isocyanate derivates is a tolylene diisocyanate, diphenylmethanediisocyanate, 1, hexamethylene-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, naphthalene-1, the 5-vulcabond, the dimer of Methylcyclohexyl diisocyanate etc., tripolymer and with TriMethylolPropane(TMP) affixture etc.
4, single-component moisture curing polyurethane caking agent as claimed in claim 1 is characterized in that with 2,2 two morphine quinoline diethyl esters and dibutyltin dilaurate as catalyzer.
5, single-component moisture curing polyurethane caking agent as claimed in claim 1 is characterized in that containing softening agent, filler, solvent, UV light absorber, ultra-violet stabilizer etc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200510132670XA CN100509986C (en) | 2005-12-28 | 2005-12-28 | Bottom agent-free type single component moisture-curing polyurethane adhesive |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200510132670XA CN100509986C (en) | 2005-12-28 | 2005-12-28 | Bottom agent-free type single component moisture-curing polyurethane adhesive |
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| CN1995256A true CN1995256A (en) | 2007-07-11 |
| CN100509986C CN100509986C (en) | 2009-07-08 |
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Cited By (16)
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| CN101818039A (en) * | 2010-04-01 | 2010-09-01 | 濮阳市万泉化工有限公司 | Single-component low-modulus polyurethane building sealant and preparation method thereof |
| CN102796483A (en) * | 2012-09-04 | 2012-11-28 | 北京高盟新材料股份有限公司 | Preparation method of transparent one-component polyurethane corner-combining adhesive |
| CN102796484A (en) * | 2012-09-04 | 2012-11-28 | 北京高盟新材料股份有限公司 | Preparation method of white one-component polyurethane corner-combining adhesive |
| CN101629061B (en) * | 2008-07-14 | 2013-06-05 | 上海新光化工有限公司 | Monocomponent moisture cure urethanes adhesive |
| CN103834345A (en) * | 2012-11-22 | 2014-06-04 | 湖北回天胶业股份有限公司 | One-component moisture-cured polyurethane sealant with excellent ultraviolet resistance |
| CN105038681A (en) * | 2015-08-28 | 2015-11-11 | 上海蒂姆新材料科技有限公司 | Silane modified resin sealing gum and preparing method thereof |
| CN105086914A (en) * | 2015-08-28 | 2015-11-25 | 上海蒂姆新材料科技有限公司 | One-component polyurethane sealing glue applicable to metal bonding and preparing method of one-component polyurethane sealing glue |
| CN105176439A (en) * | 2015-08-28 | 2015-12-23 | 上海蒂姆新材料科技有限公司 | Adhesive used adhesion promoter, and synthetic method and applications thereof |
| CN105176479A (en) * | 2015-08-28 | 2015-12-23 | 上海蒂姆新材料科技有限公司 | High-strength silicone rubber and preparation method therefor |
| CN105368366A (en) * | 2015-12-15 | 2016-03-02 | 山东北方现代化学工业有限公司 | Silane-terminated polyether sealant and preparation method thereof |
| CN108239516A (en) * | 2018-01-02 | 2018-07-03 | 杭州之江有机硅化工有限公司 | A kind of high intensity exempts from primary coat monocomponent polyurethane windshield glue and preparation method thereof |
| CN109021212A (en) * | 2018-07-13 | 2018-12-18 | 杭州之江新材料有限公司 | A kind of transparent group of angle glue of mono-component polyurethane and preparation method thereof |
| CN110484190A (en) * | 2019-09-05 | 2019-11-22 | 山西省应用化学研究所(有限公司) | Caravan vehicle body solvent-free single-component moisture cure urethanes adhesive and preparation method thereof |
| CN111094497A (en) * | 2017-09-12 | 2020-05-01 | 横滨橡胶株式会社 | Urethane adhesive composition |
| CN112080244A (en) * | 2020-09-24 | 2020-12-15 | 杭州之江新材料有限公司 | High-strength and fast-curing one-component primer-free polyurethane sealant and preparation method thereof |
| CN113429926A (en) * | 2021-06-29 | 2021-09-24 | 东风汽车有限公司东风日产乘用车公司 | Polyurethane adhesive and preparation method and application thereof |
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2005
- 2005-12-28 CN CNB200510132670XA patent/CN100509986C/en active Active
Cited By (22)
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|---|---|---|---|---|
| CN101629061B (en) * | 2008-07-14 | 2013-06-05 | 上海新光化工有限公司 | Monocomponent moisture cure urethanes adhesive |
| CN101818039A (en) * | 2010-04-01 | 2010-09-01 | 濮阳市万泉化工有限公司 | Single-component low-modulus polyurethane building sealant and preparation method thereof |
| CN101818039B (en) * | 2010-04-01 | 2013-02-13 | 濮阳市万泉化工有限公司 | Single-component low-modulus polyurethane building sealant and preparation method thereof |
| CN102796483A (en) * | 2012-09-04 | 2012-11-28 | 北京高盟新材料股份有限公司 | Preparation method of transparent one-component polyurethane corner-combining adhesive |
| CN102796484A (en) * | 2012-09-04 | 2012-11-28 | 北京高盟新材料股份有限公司 | Preparation method of white one-component polyurethane corner-combining adhesive |
| CN102796484B (en) * | 2012-09-04 | 2013-10-30 | 北京高盟新材料股份有限公司 | Preparation method of white one-component polyurethane corner-combining adhesive |
| CN102796483B (en) * | 2012-09-04 | 2013-10-30 | 北京高盟新材料股份有限公司 | Preparation method of transparent one-component polyurethane corner-combining adhesive |
| CN103834345A (en) * | 2012-11-22 | 2014-06-04 | 湖北回天胶业股份有限公司 | One-component moisture-cured polyurethane sealant with excellent ultraviolet resistance |
| CN103834345B (en) * | 2012-11-22 | 2017-05-31 | 湖北回天新材料股份有限公司 | A kind of excellent one-component damp solidifying polyurethane fluid sealant of UV resistant performance |
| CN105176439A (en) * | 2015-08-28 | 2015-12-23 | 上海蒂姆新材料科技有限公司 | Adhesive used adhesion promoter, and synthetic method and applications thereof |
| CN105086914A (en) * | 2015-08-28 | 2015-11-25 | 上海蒂姆新材料科技有限公司 | One-component polyurethane sealing glue applicable to metal bonding and preparing method of one-component polyurethane sealing glue |
| CN105176479A (en) * | 2015-08-28 | 2015-12-23 | 上海蒂姆新材料科技有限公司 | High-strength silicone rubber and preparation method therefor |
| CN105038681A (en) * | 2015-08-28 | 2015-11-11 | 上海蒂姆新材料科技有限公司 | Silane modified resin sealing gum and preparing method thereof |
| CN105368366A (en) * | 2015-12-15 | 2016-03-02 | 山东北方现代化学工业有限公司 | Silane-terminated polyether sealant and preparation method thereof |
| CN105368366B (en) * | 2015-12-15 | 2018-05-25 | 山东北方现代化学工业有限公司 | A kind of silane-terminated polyether fluid sealant and preparation method thereof |
| CN111094497A (en) * | 2017-09-12 | 2020-05-01 | 横滨橡胶株式会社 | Urethane adhesive composition |
| CN111094497B (en) * | 2017-09-12 | 2021-12-21 | 西卡豪马泰特株式会社 | Urethane adhesive composition |
| CN108239516A (en) * | 2018-01-02 | 2018-07-03 | 杭州之江有机硅化工有限公司 | A kind of high intensity exempts from primary coat monocomponent polyurethane windshield glue and preparation method thereof |
| CN109021212A (en) * | 2018-07-13 | 2018-12-18 | 杭州之江新材料有限公司 | A kind of transparent group of angle glue of mono-component polyurethane and preparation method thereof |
| CN110484190A (en) * | 2019-09-05 | 2019-11-22 | 山西省应用化学研究所(有限公司) | Caravan vehicle body solvent-free single-component moisture cure urethanes adhesive and preparation method thereof |
| CN112080244A (en) * | 2020-09-24 | 2020-12-15 | 杭州之江新材料有限公司 | High-strength and fast-curing one-component primer-free polyurethane sealant and preparation method thereof |
| CN113429926A (en) * | 2021-06-29 | 2021-09-24 | 东风汽车有限公司东风日产乘用车公司 | Polyurethane adhesive and preparation method and application thereof |
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