JPS6348917B2 - - Google Patents
Info
- Publication number
- JPS6348917B2 JPS6348917B2 JP3412381A JP3412381A JPS6348917B2 JP S6348917 B2 JPS6348917 B2 JP S6348917B2 JP 3412381 A JP3412381 A JP 3412381A JP 3412381 A JP3412381 A JP 3412381A JP S6348917 B2 JPS6348917 B2 JP S6348917B2
- Authority
- JP
- Japan
- Prior art keywords
- primer
- formula
- metals
- component
- mainly consists
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000853 adhesive Substances 0.000 claims description 15
- 230000001070 adhesive effect Effects 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 11
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 150000003077 polyols Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 5
- 239000005056 polyisocyanate Substances 0.000 claims description 5
- 239000013615 primer Substances 0.000 description 18
- 239000002987 primer (paints) Substances 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- -1 etc. Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Description
本発明は片方の液がポリイソシアネートからな
り、他方の液が主としてポリオールからなる二液
ウレタン系接着剤を用いて金属を接着する方法に
関する。
一般に二液ウレタン系接着剤は金属への接着性
が不良であるために、二液ウレタン系接着剤にて
金属同士又は金属と他の被着体を接着する場合に
は、接着の前に予めプライマーを使つて金属表面
を処理することが知られている。例えば、プライ
マーとしては、二液のエポキシ樹脂をそれぞれ揮
発性溶剤に溶解したもの、及びフエノール樹脂を
揮発性溶剤に溶解したものがあり、これらのプラ
イマーを金属表面に塗布する。いずれも接着性は
良好になるが、エポキシ樹脂の場合は二液を夫々
計量混合しなければならず、又硬化に加熱又は長
時間が必要であり、そしてフエノール樹脂の場合
も硬化に加熱が必要である。
本発明はこれらのプライマーの欠点を改良すべ
く、研究した結果、一液で加熱の必要がなく、短
時間で二液ウレタン系接着剤の金属への接着を可
能にするプライマーを見い出し、本発明に到達し
た。
即ち、本発明によれば、片方の液が主としてポ
リイソシアネートからなり、他方の液が主として
ポリオールからなる二液ウレタン系接着剤を用い
て金属を接着するに際し、金属面を予め
一般式
The present invention relates to a method for bonding metals using a two-component urethane adhesive in which one component is comprised of polyisocyanate and the other component is primarily comprised of polyol. In general, two-component urethane adhesives have poor adhesion to metals, so when using two-component urethane adhesives to bond metals to each other or metals to other adherends, it is necessary to It is known to treat metal surfaces using primers. For example, primers include two-component epoxy resins dissolved in volatile solvents and phenolic resins dissolved in volatile solvents, and these primers are applied to the metal surface. Both have good adhesion, but in the case of epoxy resin, the two components must be measured and mixed, and curing requires heating or a long time, and phenolic resin also requires heating to cure. It is. In order to improve the shortcomings of these primers, the present invention conducted research and discovered a primer that is one-component and does not require heating, allowing a two-component urethane adhesive to adhere to metal in a short time. reached. That is, according to the present invention, when bonding metals using a two-component urethane adhesive in which one liquid mainly consists of polyisocyanate and the other liquid mainly consists of polyol, the metal surface is preliminarily bonded to the general formula
【式】（式中、R1は末端に
OH基を１個有する有機基であり、R2はＨ又はR1
若しくはその他の有機基である。）で表わされる
化合物を揮発性溶剤に溶解したプライマーで処理
した後に接着することを特徴とする接着方法が提
供される。
本発明の接着方法に用いる二液ウレタン系接着
剤は、片方の液が主としてポリイソシアネートか
らなり、他方の液が主としてポリオールからな
る。ポリイソシアネートとしてはトルエンジイソ
シアネート、ジフエニルメタンジイソシアネー
ト、トリフエニルメタントリイソシアネート、ヘ
キサメチレンジイソシアネート及びこれらの誘導
体等が挙げられ、又ポリオールとしてはエチレン
グリコール、プロピレングリコール、グリセリ
ン、ヒマシ油及びこれらの誘導体であるポリエー
テルポリオール及びポリエステルポリオール等が
挙げられる。そして、この二液ウレタン系接着剤
のそれぞれの液には、必要に応じて触媒、充填
剤、樹脂、溶剤又は可塑剤等を添加することがで
きる。
本発明の接着方法では、プライマーとして一般
式[Formula] (In the formula, R 1 is an organic group having one OH group at the end, R 2 is H or R 1
or other organic groups. There is provided an adhesion method characterized in that the compound represented by ) is bonded after being treated with a primer dissolved in a volatile solvent. In the two-part urethane adhesive used in the bonding method of the present invention, one part mainly consists of polyisocyanate and the other part mainly consists of polyol. Examples of polyisocyanates include toluene diisocyanate, diphenylmethane diisocyanate, triphenylmethane triisocyanate, hexamethylene diisocyanate, and derivatives thereof, and examples of polyols include ethylene glycol, propylene glycol, glycerin, castor oil, and derivatives thereof. Examples include polyether polyols and polyester polyols. A catalyst, a filler, a resin, a solvent, a plasticizer, etc. can be added to each liquid of the two-component urethane adhesive, if necessary. In the adhesion method of the present invention, the general formula
【式】（式中、R1は未端にOH基を
１個有する有機基であり、R2はＨ又はR1若しく
はその他の有機基である。）で表わされる化合物
を揮発性溶剤に溶解したものを用いる。上記一般
式で表わされる化合物としては、リン酸とエチレ
ングリコール等前記のポリオール成分として使え
る化合物とのモノ又はジエステルであり、アルコ
ール性水酸基が１個以上残つていることが必要で
あり、モノエステルの場合、更にリン酸基がアル
コール性水酸基を１個含む化合物とエステル化し
ているジエステルとなすこともできるし、或いは
モノエステルをアミン等で塩にしていてもよい。
プライマーの揮発性溶剤としては、メタノール及
びエタノールが好ましいが、上記一般式で表わさ
れる化合物が溶解できれば、いずれのものでもよ
く、例えばアセトン、酢酸エチル及び水等やこれ
らの混合物が用いられる。プライマー中の上記一
般式で表わされる化合物の含有量は0.01〜10重量
％が好ましく、0.05〜３重量％の範囲が特に好ま
しい。
本発明の接着方法によれば、金属同士又は金属
と他の被着体例えば、金属と布、木材、エポキシ
FRP及びポリエステルFRP等の熱硬化性樹脂、
並びにエポキシ樹脂及びフエノール樹脂等の塗装
面等の接着が迅速かつ容易に実施可能で、そして
強力な接着力が得られる。
実施例 １[Formula] (wherein, R 1 is an organic group having one OH group at the end, and R 2 is H or R 1 or another organic group) is dissolved in a volatile solvent. Use the one you made. The compound represented by the above general formula is a mono- or diester of phosphoric acid and a compound that can be used as the above-mentioned polyol component such as ethylene glycol, and it is necessary that one or more alcoholic hydroxyl groups remain. In this case, a diester in which a phosphoric acid group is further esterified with a compound containing one alcoholic hydroxyl group, or a monoester may be made into a salt with an amine or the like.
As the volatile solvent for the primer, methanol and ethanol are preferred, but any solvent may be used as long as it can dissolve the compound represented by the above general formula, such as acetone, ethyl acetate, water, etc., and mixtures thereof. The content of the compound represented by the above general formula in the primer is preferably 0.01 to 10% by weight, particularly preferably 0.05 to 3% by weight. According to the bonding method of the present invention, metals can be bonded to each other, or metals and other adherends, such as metals and cloth, wood, epoxy
Thermosetting resins such as FRP and polyester FRP,
Furthermore, it is possible to quickly and easily bond surfaces coated with epoxy resins, phenolic resins, etc., and a strong adhesive force can be obtained. Example 1
【式】をエタノールに溶
解して１重量％溶液をつくり、これをプライマー
とした。
厚さ0.3mmの鉄片（JIS G314SPCC−SB）２枚
に上記プライマーをはけ塗りし、乾燥した。
下記の二液ウレタン接着剤のＡ液とＢ液を重量
比でＡ液／Ｂ液＝1.6／1.0の割合で混合し、混合
液を上記２枚の鉄片のプライマー塗布面に塗布し
接着せしめた。
接着後室温にて１週間養生した後、Ｔ剥離強度
を測定した。
又、比較のためにプライマーの処理を行なわな
いで、上記接着剤を用いて同様にして上記と同質
の鉄片を接着し、Ｔ剥離強度を測定した。
使用したウレタン接着剤
Ａ液：ジフエニルメタンジイソシアネート変性物
（住友バイエルウレタン社製 商品名スミジユ
ールＥ−21−１）
Ｂ液：ポリエーテルポリオール（アサヒデンカ社
製 商品名アデカポリエーテルポリオールＧ−
400と同Ｇ−1500の等重量混合物）
接着試験結果
Ｔ剥離強度
プライマー処理したもの（本発明）6.5Kg／2.5cm
プライマー処理しないもの（比較例）
0.5Kg／2.5cm
実施例 ２
厚さ２mmのアルミニウム試験片（JIS H4000
A5052P）に実施例１で用いたプライマーを塗布
し、乾燥した後、実施例１で用いた接着剤を塗布
した。別に同じ接着剤を９号綿キヤンバスに塗布
した。アルミニウムと綿キヤンバスの接着剤塗布
面を合せ、室温で１週間養生した後、180度剥離
強度を測定した。
比較のために、上記と同質のアルミニウム試験
片にプライマー処理をせずに、上記と同様の接着
試験を行なつた。結果は次の通りであつた。
180度剥離強度
プライマー処理したもの（本発明）9.5Kg／2.5cm
プライマー処理しないもの（比較例）
0.9Kg／2.5cm[Formula] was dissolved in ethanol to prepare a 1% by weight solution, which was used as a primer. The above primer was brushed onto two pieces of iron (JIS G314SPCC-SB) with a thickness of 0.3 mm and dried. The following two-component urethane adhesive liquids A and B were mixed at a weight ratio of liquid A/liquid B = 1.6/1.0, and the mixed liquid was applied to the primer-coated surfaces of the two iron pieces and bonded. . After being cured for one week at room temperature after adhesion, the T-peel strength was measured. For comparison, an iron piece of the same quality as above was adhered in the same manner using the above adhesive without any primer treatment, and the T-peel strength was measured. Urethane adhesive used Liquid A: Diphenylmethane diisocyanate modified product (manufactured by Sumitomo Bayer Urethane Co., Ltd., trade name: Sumidyur E-21-1) Liquid B: Polyether polyol (manufactured by Asahi Denka Co., Ltd., trade name: ADEKA Polyether Polyol G-)
400 and the same weight of G-1500) Adhesion test results T peel strength Primer treated (invention) 6.5Kg/2.5cm No primer treatment (comparative example)
0.5Kg/2.5cm Example 2 2mm thick aluminum test piece (JIS H4000
A5052P) was coated with the primer used in Example 1, dried, and then coated with the adhesive used in Example 1. Separately, the same adhesive was applied to a No. 9 cotton canvas. The adhesive-coated surfaces of the aluminum and cotton canvas were placed together, cured at room temperature for one week, and then the 180 degree peel strength was measured. For comparison, an adhesion test similar to that described above was conducted on an aluminum test piece of the same quality as above, but without primer treatment. The results were as follows. 180 degree peel strength Primer treated (invention) 9.5Kg/2.5cm No primer treatment (comparative example)
0.9Kg/2.5cm
Claims (1)
なり、他方の液が主としてポリオールからなる二
液ウレタン系接着剤を用いて金属を接着するに際
し、金属面を予め 一般式【式】（式中、R1は末端に OH基を１個有する有機基であり、R2はＨ又はR1
若しくはその他の有機基である。）で表わされる
化合物を揮発性溶剤に溶解したプライマーで処理
した後に接着することを特徴とする接着方法。[Claims] 1. When bonding metals using a two-component urethane adhesive in which one liquid mainly consists of polyisocyanate and the other liquid mainly consists of polyol, the metal surface is preliminarily bonded to the general formula [formula] ( In the formula, R 1 is an organic group having one OH group at the end, and R 2 is H or R 1
or other organic groups. ) A bonding method characterized in that the compound is treated with a primer dissolved in a volatile solvent and then bonded.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3412381A JPS57149374A (en) | 1981-03-10 | 1981-03-10 | Bonding method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3412381A JPS57149374A (en) | 1981-03-10 | 1981-03-10 | Bonding method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57149374A JPS57149374A (en) | 1982-09-14 |
| JPS6348917B2 true JPS6348917B2 (en) | 1988-10-03 |
Family
ID=12405464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3412381A Granted JPS57149374A (en) | 1981-03-10 | 1981-03-10 | Bonding method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57149374A (en) |
-
1981
- 1981-03-10 JP JP3412381A patent/JPS57149374A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57149374A (en) | 1982-09-14 |
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