JPH0258583A - Bonding - Google Patents
BondingInfo
- Publication number
- JPH0258583A JPH0258583A JP20946188A JP20946188A JPH0258583A JP H0258583 A JPH0258583 A JP H0258583A JP 20946188 A JP20946188 A JP 20946188A JP 20946188 A JP20946188 A JP 20946188A JP H0258583 A JPH0258583 A JP H0258583A
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- weight
- bonded
- parts
- imide
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 claims abstract description 53
- 230000001070 adhesive effect Effects 0.000 claims abstract description 53
- -1 imide compound Chemical class 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 15
- 229940015043 glyoxal Drugs 0.000 claims abstract description 13
- 229920000126 latex Polymers 0.000 claims abstract description 12
- 239000004816 latex Substances 0.000 claims abstract description 12
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 11
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 11
- 230000004048 modification Effects 0.000 claims abstract description 9
- 238000012986 modification Methods 0.000 claims abstract description 9
- 229920001577 copolymer Polymers 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 150000003949 imides Chemical class 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 20
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 abstract description 25
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000004593 Epoxy Substances 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000015271 coagulation Effects 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 7
- 239000002023 wood Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000005462 imide group Chemical group 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920005615 natural polymer Polymers 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 239000004830 Super Glue Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000007718 adhesive strength test Methods 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- OBRMNDMBJQTZHV-UHFFFAOYSA-N cresol red Chemical compound C1=C(O)C(C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C=C(C)C(O)=CC=2)=C1 OBRMNDMBJQTZHV-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- SJPFBRJHYRBAGV-UHFFFAOYSA-N n-[[3-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C=C(CN(CC2OC2)CC2OC2)C=CC=1)CC1CO1 SJPFBRJHYRBAGV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Landscapes
- Finished Plywoods (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は木質材料と木質材料、無機板、紙等を極めて短
時間に接着する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a method for bonding wood materials, inorganic boards, paper, etc. in an extremely short time.
(従来の技術)
従来、瞬間接着の手段としてはシアノアクリレート系接
着剤や分別塗付を基本とするアクリル系接着剤の使用が
ある。これらの接着剤は価格が高く、かつ取扱い上に制
約が多くて小面積の接着には適応できるが大面積、大規
模な接着作業には適応できない。(Prior Art) Conventionally, as means for instant bonding, cyanoacrylate adhesives and acrylic adhesives based on separate application have been used. These adhesives are expensive, have many restrictions in handling, and are suitable for bonding small areas, but cannot be used for large-scale bonding operations.
また特開昭56−90867によると分子内にアミド結
合あるいはイミド基を有する天然もしくは合成高分子水
溶液とジアルデヒド化合物の水溶液を被着材の両方の面
にEll々に塗付し速硬化性の接着剤として利用するこ
とが提案されている。この方法は互いの被着材の接着面
積と形状が同一の場合には問題はないが、枠材と桟材を
組合わせ骨組材とし面材を接着するフラッシュパネルの
製造のような場合、面材の全面に分子内にアミド結合あ
るいはイミド基を塗付することは接着部以外が全く無駄
な部分となって経済的に不利であると共に、面材は供給
された水分の為に反りを生じているので解圧時にその応
力から剥離を起こし易く好ましくない。また骨組材との
接着部に合わせて面材上に同様の作業を行なことは全く
繁雑で、作業コストも上りコストの上昇を招く。Furthermore, according to JP-A No. 56-90867, an aqueous solution of a natural or synthetic polymer having an amide bond or an imide group in the molecule and an aqueous solution of a dialdehyde compound are applied to both surfaces of the adherend in a fast-curing manner. It has been proposed to be used as an adhesive. There is no problem with this method when the bonding area and shape of the adherend materials are the same, but when manufacturing a flash panel where the frame material and crosspiece are combined as a frame material and the surface material is bonded, Applying amide bonds or imide groups in the molecules to the entire surface of the material is economically disadvantageous as the parts other than the bonded areas are completely wasted, and the facing material also warps due to the supplied moisture. This is undesirable because it tends to cause peeling due to the stress when the pressure is released. Further, it is quite complicated to carry out the same work on the face material in accordance with the bonding part with the frame material, and the work cost increases, leading to an increase in the cost.
(本発明が解決しようとしている問題点)接着製品の生
産に於いても、生産性向上の手段としての接着に要する
時間の短縮、工程の単純化は広く熱望されているところ
である。そしてその手段は、接着しようとする材料双方
の面に接着剤成分を別々に塗付するような繁雑でまt;
非経済的な工程のものではなく、被着材の片方のみへ処
理と塗付の工程で作業性が良好でかつ接着剤も安価な接
着方法の開発が待たれていた。接着の工程には、被着材
に接着剤を塗付後引続いた圧締の工程がある。この場合
、接着剤を塗付後接着に充分な圧力がかかるまでの堆積
時間が充分とれることは作業上重要な接着剤の性質であ
る。本発明者等は、この接着工程部の解決方法について
鋭意研究を進めた結果、前記処理剤(a)および接着剤
(b)を使用することによって、充分な堆積時間を確保
して作業でき且つ極めて短時間に接着する方法を完成す
るに至った。(Problems to be Solved by the Invention) In the production of adhesive products, there is a widespread desire to shorten the time required for adhesion and simplify the process as a means of improving productivity. The method is complicated and involves applying adhesive components separately to both surfaces of the materials to be bonded;
There has been a long-awaited development of a bonding method that does not require an uneconomical process, but requires a process of treating and applying only one side of the adherend, which is easy to work with and uses an inexpensive adhesive. The adhesion process includes a process of applying an adhesive to the adherend and subsequent pressing. In this case, it is an important property of the adhesive to allow sufficient deposition time after application until sufficient pressure is applied for adhesion. The inventors of the present invention have carried out intensive research into solutions for this bonding process, and have found that by using the processing agent (a) and adhesive (b), sufficient deposition time can be secured for the work. We have completed a method of bonding in an extremely short time.
本発明は、枠材と桟材を組合わせた骨組材に面材を接着
するいわゆるフラッシュパネルの製造に特に好適な極め
て短時間に接着する方法に関するものである。The present invention relates to an extremely short-time bonding method that is particularly suitable for manufacturing so-called flash panels, in which a panel is bonded to a frame material that is a combination of a frame material and a crosspiece.
(問題点を解決するための手段)
本発明者等は上記目的を達成すべく鋭意研究の結果、特
定濃度でグリオキザールとヘキサメチレンテトラミンを
含んで成る水溶液である処理剤(a)と、特定の分子量
範囲を持ち分子内に特定範囲量のイミド基を持つイソブ
チレン−無水マレイン酸イミド変性化合物およびカルボ
キシ変性スチレン−ブタジエン系ラテックス、および必
要に応じて多官能エポキシ化合物から成る水性組成物で
ある接着剤(b)を組合わせて使用し、被着材の片方の
みへ重ねて塗付することにより、良好な作業性と強固な
接着強さを発現できることを見出し、本発明を完成する
至った。即ち本発明は、接着剤(b)を凝固させる処理
剤(a)を予め一方の被着材に塗付し乾燥後、次に該処
理被着材に接着剤(b)を重ねて塗付し他方の被着材を
重ねて貼り合わせる工程より成ることを特徴とする極め
て短時間に接着する方法に関する。(Means for Solving the Problem) As a result of intensive research to achieve the above object, the present inventors have developed a treatment agent (a) which is an aqueous solution containing glyoxal and hexamethylenetetramine at a specific concentration, and a specific An adhesive that is an aqueous composition consisting of an isobutylene-maleic anhydride-modified compound having a molecular weight range and a specific amount of imide groups in the molecule, a carboxy-modified styrene-butadiene latex, and optionally a polyfunctional epoxy compound. It has been discovered that good workability and strong adhesive strength can be achieved by using a combination of (b) and applying the adhesive to only one side of the adherend, thereby completing the present invention. That is, in the present invention, the treatment agent (a) for coagulating the adhesive (b) is applied to one adherend in advance, and after drying, the adhesive (b) is then overlaid and applied to the treated adherend. The present invention relates to a method for bonding in an extremely short period of time, which comprises the steps of overlapping and bonding the other adherend.
本発明に関する処理剤(a)は、グリオキザールおよび
ヘキサメチレンテトラミンを含んで成る水溶液である。The treatment agent (a) according to the present invention is an aqueous solution comprising glyoxal and hexamethylenetetramine.
グリオキザールの濃度は5〜25重量%の範囲であるが
、望ましくは10〜20重量%である。グリオキザール
が5重量%未満の場合には接着剤(b)の凝固が遅く、
目的とする効果が得られない。またグリオキザールの濃
度が25重量%を越える場合は処理剤(a)の塗布面で
の凝固が遅すぎて接着不良を起こし易く、好ましくない
。一方、ヘキサメチレンテトラミンの濃度は1〜101
i量%の範囲であるが、望ましくは2〜8重量%である
。ヘキサメチレンテトラミンの適量は処理剤(a)を中
性域にとどめイミド化合物の凝固速度を制御する他、耐
水接着強度を向上する効果がある。ヘキサメチレンテト
ラミンを配合しない場合には処理剤(a)の酸性度が強
く木材の損傷を起こし易く、好ましくない。また濃度が
高い場合にには処理剤(a)のpHが上がり接着剤の凝
固が遅れて期待する短時間の接着に好ましくない結果を
与える。処理剤(a)には塗付適性をよくするために水
溶性の溶剤、例えばアルコール系、ケトン系、エステル
系等を混合することができる。また同じ目的のために界
面活性剤を混合することができる。処理剤(a)の塗付
量は被着材の種類により適宜調整する。The concentration of glyoxal ranges from 5 to 25% by weight, preferably from 10 to 20% by weight. When glyoxal is less than 5% by weight, the adhesive (b) coagulates slowly;
The desired effect cannot be obtained. Moreover, if the concentration of glyoxal exceeds 25% by weight, the coagulation of the treatment agent (a) on the coated surface is too slow, which tends to cause poor adhesion, which is not preferable. On the other hand, the concentration of hexamethylenetetramine is 1 to 101
i amount%, preferably 2 to 8% by weight. An appropriate amount of hexamethylenetetramine has the effect of keeping the treatment agent (a) in a neutral range and controlling the coagulation rate of the imide compound, as well as improving the water-resistant adhesive strength. When hexamethylenetetramine is not blended, the acidity of the treatment agent (a) is strong and tends to damage the wood, which is not preferable. In addition, if the concentration is high, the pH of the treatment agent (a) will increase and coagulation of the adhesive will be delayed, resulting in unfavorable short-term adhesion. The treatment agent (a) may be mixed with a water-soluble solvent such as an alcohol, ketone, or ester solvent in order to improve its applicability. Surfactants can also be mixed for the same purpose. The amount of treatment agent (a) applied is adjusted as appropriate depending on the type of adherend.
本発明に使用する接着剤(b)は(1)イミド化合物及
び(2)カルボキシ変性スチレン−ブタジエン系ラテッ
クスおよび必要に応じて耐水性を付与するための(3)
1分子に2個以上のエポキシ基を持つ多官能エポキシ化
合物から成る。The adhesive (b) used in the present invention is (1) an imide compound, (2) a carboxy-modified styrene-butadiene latex, and optionally (3) for imparting water resistance.
Consists of a polyfunctional epoxy compound with two or more epoxy groups in one molecule.
イミド化合物(])と]カルボキシ変性スチレンーブタ
ジェン系ラテックス2)とは20〜40重置部の(1)
と固形分として60〜80重量部の(2)との割合で使
用されるが、25〜35重量部と65〜75重量部の割
合が好適である。イミド化合物の量が20重量部より小
さい場合は地理剤(a)による凝固が弱くなり良好な接
着力を得ることができず、また40重量部より大きい場
合は耐水性が低くなり、また糊液が増粘する等で作業上
好ましくない。The imide compound (]) and the carboxy-modified styrene-butadiene latex 2) are (1) of 20 to 40 overlapping parts.
(2) is used in a ratio of 60 to 80 parts by weight as a solid content, but a ratio of 25 to 35 parts by weight and 65 to 75 parts by weight is suitable. If the amount of the imide compound is less than 20 parts by weight, coagulation by the geographical agent (a) will be weak and good adhesive strength cannot be obtained, and if it is more than 40 parts by weight, water resistance will be low and the size liquid This is not desirable for work as it increases the viscosity.
接着剤(b)には流動性の調節、接着強度の補強及び増
量の目的で必要に応じ充填剤を配合することができる。If necessary, a filler may be added to the adhesive (b) for the purpose of adjusting fluidity, reinforcing adhesive strength, and increasing the amount.
配合量は上記イミド化合物(1)と上記ラテックス(2
)の固形分との合計量に基いて100重量%以下が望ま
しい。接着剤(b)に使用する充填剤には炭酸カルシウ
ム、炭酸バリウム、ンリカ、クレー、タルク、木粉等が
ある。The blending amounts are the above imide compound (1) and the above latex (2).
) is desirably 100% by weight or less based on the total amount of solid content. Fillers used in adhesive (b) include calcium carbonate, barium carbonate, limestone, clay, talc, wood flour, and the like.
これらは単独で使用してもよく2種類以上を併用するこ
ともできる。These may be used alone or in combination of two or more.
接着剤(b)に使用するイミド化合物(1)で、イソブ
チレン−無水マレイン酸共重合物の分子量を8〜9×1
04に限定したのは、分子量の低い5.5〜6.5XI
OL付近では耐水性および解圧時の強度が充分でなく、
また分子量16〜17X10’付近の高いものを用いた
場合は糊液が増粘し、実用上使用できる接着剤とするた
めには低いイミド化率としなければならず、従って耐水
性が低くなり解圧時の強度も低くなる。The imide compound (1) used in the adhesive (b) has a molecular weight of 8 to 9 x 1 of the isobutylene-maleic anhydride copolymer.
04 is limited to 5.5 to 6.5XI, which has a low molecular weight.
Water resistance and strength at depressurization are not sufficient near OL,
Furthermore, if a high molecular weight material with a molecular weight of around 16 to 17 x 10' is used, the adhesive will thicken, and in order to make an adhesive that can be used for practical purposes, it must have a low imidization rate, resulting in low water resistance and degradation. The strength under pressure also decreases.
本発明に使用するイミド化合物(1)はイソブチレン−
無水マレイン酸共重合物をイミド変性することによって
得られる。変性率は30〜50モル%がよく、さらに望
ましくは35〜45モル%である。変性率が30モル%
未満の場合は処理剤(a)による凝固が弱くなり短時間
の圧締では接着力を得ることができない。また変性率が
50モル%を越える場合は糊液は強い曳糸性を示し、か
つ処理剤(a)による凝固も強過ぎて接着剤(b)を重
ねて塗付し圧締した場合、被着材への漏れが悪く望まし
い強度が得られない。The imide compound (1) used in the present invention is isobutylene-
It is obtained by imide-modifying a maleic anhydride copolymer. The modification rate is preferably 30 to 50 mol%, more preferably 35 to 45 mol%. Modification rate is 30 mol%
If it is less than 1, the coagulation by the treatment agent (a) becomes weak and adhesive strength cannot be obtained by pressing for a short time. In addition, if the modification rate exceeds 50 mol%, the size liquid exhibits strong stringiness, and the coagulation by the processing agent (a) is too strong, and when the adhesive (b) is applied and pressed in layers, it becomes difficult to coat the adhesive. Leakage into the material is poor and the desired strength cannot be obtained.
本明細書においていう「変性率」とは、下記の如く規定
されるものである。イソブチレン−無水マレイン酸共重
合物のアンモニヤ付加物よりイミド化合物(1)へ変性
する反応は脱アンモニヤ・脱水反応であり、反応によっ
て生じた水は反応系外へ溜去される。即ち、溜去された
水量を計測して、次式によってイミド反応の変性率(モ
ル%)を求めることができる。The term "denaturation rate" as used herein is defined as follows. The reaction of modifying the ammonia adduct of the isobutylene-maleic anhydride copolymer into the imide compound (1) is a deammonization/dehydration reaction, and the water produced by the reaction is distilled out of the reaction system. That is, by measuring the amount of water distilled off, the modification rate (mol %) of the imide reaction can be determined using the following equation.
[式中、Aは脱水fk(g)、Wはイソブチレン−無水
マレイン酸共重物の採取量(g)、154(g)はイン
ブチレン・無水マレイン酸共重物の繰返し単位の分子量
(g)である。]
上記イミド化合物(1)は水酸化ナトリウム、水酸化カ
リウム、炭酸ソーダ、燐酸アンモニウム、水酸化アンモ
ニウム、アミン等の塩基性物質の単独または2種以上を
併用して溶解した水溶液として使用する。[In the formula, A is the dehydration fk (g), W is the amount of isobutylene-maleic anhydride copolymer collected (g), and 154 (g) is the molecular weight of the repeating unit of the inbutylene-maleic anhydride copolymer (g). ). ] The imide compound (1) is used as an aqueous solution prepared by dissolving basic substances such as sodium hydroxide, potassium hydroxide, sodium carbonate, ammonium phosphate, ammonium hydroxide, and amines alone or in combination of two or more.
接着剤(b)に使用する水性ラテックスを特にカルボキ
シ変性スチレン−ブタジエン系ラテックス(2)に限定
したのは、解圧時の強度が高く、かつ架橋剤として使用
する多官能エポキシ化合物によって高度な耐水性が得ら
れるためである。The water-based latex used for adhesive (b) was specifically limited to carboxy-modified styrene-butadiene latex (2) because it has high strength when decompressed and has high water resistance due to the polyfunctional epoxy compound used as a crosslinking agent. This is because it gives you sex.
接着剤(b)に使用する1分子中に2個以上のエポキシ
基を持つ多官能エボキン化合物(3)は、低粘度の液体
が好ましく、例えばN、N、N’、N’−テトラグリシ
ジル−1,3−キシリレンジアミン、1.3−ビス(N
−ジグリシジルアミノメチル)ンクロヘキサン等の4官
能工ポキシ化合物と、グリセロール−トリグリシジルエ
ーテルの3官能工ポキン化合物および0−7タリツクア
シツドージグリシジルエステル、エチレングリコール−
ジグリシジルエーテル、グリセロール−ジグリシジルエ
ーテル、1.6−ヘキサンシオールージグリシジルエー
テル、ネオベンチールグリコール−ジグリシジルエーテ
ル等の2官能工ポキシ化合物等が使用される。これらは
単独で使用してもよく、2種以上を併用して使用するこ
ともできる。これらの多官能エポキシ化合物(3)の混
合割合は特に規定するものではないが、通常は求める性
能により、上記イミド化合物(1)と上記ラテックス(
2)の固形分との合計量に基いて1〜30重量%とされ
る。1重量%未満では耐水性向上の効果は少く、また3
0重量%を越えると本発明の目的とする極めて短時間の
接着方法には解圧時の高い強度が期待できなく、接着剤
(b)の粘度変化も大きくなる等、作業に困難を来たす
場合があるので好ましくない。The polyfunctional Evoquin compound (3) having two or more epoxy groups in one molecule used in the adhesive (b) is preferably a low viscosity liquid, such as N,N,N',N'-tetraglycidyl- 1,3-xylylenediamine, 1,3-bis(N
- Tetrafunctional poxy compounds such as diglycidylaminomethyl)cyclohexane, trifunctional poxy compounds such as glycerol triglycidyl ether, 0-7 triglycidyl ester, ethylene glycol -
Difunctional poxy compounds such as diglycidyl ether, glycerol-diglycidyl ether, 1,6-hexanethiol-diglycidyl ether, and neobentyl glycol-diglycidyl ether are used. These may be used alone or in combination of two or more. The mixing ratio of these polyfunctional epoxy compounds (3) is not particularly specified, but usually the imide compound (1) and the latex (
The amount is 1 to 30% by weight based on the total amount including the solid content of 2). If it is less than 1% by weight, the effect of improving water resistance will be small;
If it exceeds 0% by weight, high strength upon decompression cannot be expected for the very short-time bonding method that is the object of the present invention, and the viscosity of the adhesive (b) will change significantly, making the work difficult. I don't like it because there is.
本発明に使用する処理剤(a)と接着剤(b)とを意識
的に混合すると瞬間的に凝固する。この凝固は処理剤(
a)に含有するアルデヒド基と接着剤(b)に含有する
イミド基の活性水素による水素結合に由来するものと推
定される。この瞬間的な凝固現象が解圧時の強度として
発現されるものである。When the treatment agent (a) and adhesive (b) used in the present invention are intentionally mixed, they coagulate instantaneously. This coagulation is caused by the processing agent (
It is presumed that this is due to hydrogen bonding between the aldehyde group contained in a) and the imide group contained in the adhesive (b) due to active hydrogen. This instantaneous solidification phenomenon is expressed as strength upon decompression.
次に本発明を実施例により説明するが実施例および比較
例における部数および%は全て重量部ならびに重量%で
ある。Next, the present invention will be explained with reference to examples, and all parts and percentages in the examples and comparative examples are parts by weight and percentages by weight.
(1) 処理剤(a)の調製
40%濃度のグリオキザール水溶液およびヘキサンメチ
レンテトラミンを用いてグリオキザール量およびヘキサ
メチレンテトラミン量の異なる処理剤(a)液を調製し
た。(1) Preparation of processing agent (a) Using a 40% concentration glyoxal aqueous solution and hexamethylenetetramine, processing agent (a) solutions having different amounts of glyoxal and hexamethylenetetramine were prepared.
(2) イミド化合物水溶液の調製
イソブチレン−無水マレイン酸共重合物[(株)クラレ
製:商品名イソパン04、分子量5.5〜6.5×10
4;イソパン06、分子量8〜9X10′;イソパンI
O1分子量16〜17XlO’1150gを撹はん下6
0°Cに加温しアンモニヤガスを吹込んでアンモニヤ付
加物とし、次に撹はん下180°Cに加温し窒素気流中
でイミド化反応を行い、下表に示すような変性率の異な
るイミド化合物を得た。このイミド化合物を水酸化ナト
リウムにより溶解し、固形分40%、pH7,2(pH
試験紙クレゾール・レッド)の水溶液としlこ 。(2) Preparation of imide compound aqueous solution Isobutylene-maleic anhydride copolymer [manufactured by Kuraray Co., Ltd.: trade name Isopan 04, molecular weight 5.5-6.5×10
4; Isopane 06, molecular weight 8-9X10'; Isopane I
1150 g of O1 molecular weight 16-17XlO' was stirred 6
The mixture was heated to 0°C and ammonia gas was blown into it to form an ammonia adduct, then heated to 180°C with stirring to perform an imidization reaction in a nitrogen stream, resulting in different modification rates as shown in the table below. An imide compound was obtained. This imide compound was dissolved in sodium hydroxide, solid content 40%, pH 7.2 (pH
An aqueous solution of test paper (cresol red).
(3) 接着剤(b)の調製
イ) イミド化合物水溶液、
口) 下表に示すようなカルボキン変性スチレン−ブタ
ジエン系ラテックス[日本合成ゴム(株)製:商品名J
SR○668、固形分48%;日本ゼオン(株>’s:
商品名二ボールLZ−430,固形分49%;住友ノー
ガタツタ(株)製:5N−307、固形分48%J、比
較例として非カルボキシ変性スチレン−ブタジエン系ラ
テックス[旭化成工業(株)製:商品名DL−[312
、固形分48%1、
ハ) 炭酸力ルンウムE日束粉化工業(株)製:商品名
N5−fool、および
二) 4官能工ポキシ化合物[三菱瓦斯化学(株)製:
商品名TETRAD−X、TETRAD−C] 、3官
能工ポキシ化合物[ナガセ化成(株)製:商品名ブナコ
ールEX−313] 、2官能工ポキシ化合物[ナガセ
化成(株)製商品名デナコールE等を加え、よく混合し
て接着剤(b)を調製した。(3) Preparation of adhesive (b) a) Imide compound aqueous solution, carboquine-modified styrene-butadiene latex as shown in the table below [manufactured by Japan Synthetic Rubber Co., Ltd.: product name J]
SR○668, solid content 48%; Nippon Zeon Co., Ltd.'s:
Product name: 2-ball LZ-430, solid content 49%; produced by Sumitomo Nogatatsuta Co., Ltd.: 5N-307, solid content 48% J; as a comparative example, non-carboxy modified styrene-butadiene latex [produced by Asahi Kasei Industries, Ltd.] Name DL-[312
, solid content 48%1, c) carbonic acid runium E manufactured by Nichizuka Funka Kogyo Co., Ltd.: trade name N5-fool, and 2) tetrafunctional poxy compound [manufactured by Mitsubishi Gas Chemical Co., Ltd.:
TETRAD-X, TETRAD-C], trifunctional poxy compounds [manufactured by Nagase Kasei Co., Ltd., trade name Bunacol EX-313], bifunctional poxy compounds [manufactured by Nagase Kasei Co., Ltd., trade name Denacol E, etc.] and mixed well to prepare adhesive (b).
(4) 割裂接着強さの測定
比重0.45±0.02、含水率10±1%のスブルー
ス材を40X40XIOmmに切断し被着材とし、この
被着材に処理剤(a)を50g/m”塗付し乾燥させる
。次に該処理面に接着剤(b)を350 g/m”重ね
て塗付する。この塗付面に比重0.45±0.02、含
水率IO±1%の40X50X5.5mmラワン合板を
、合板表面の繊維方向とスブルース材の繊維方向が直交
するように貼り合わせる。堆積時間3分子i、°I O
k g / c m 2で1分間圧締する。解圧後直ち
に(株)東洋ボードウィン製引張り試験機を用い、引張
り速度毎5’) 100 m mで割裂強さを測定した
。(4) Measurement of Splitting Adhesive Strength Stainless steel material with a specific gravity of 0.45 ± 0.02 and a water content of 10 ± 1% was cut into 40 x 40 x IO mm pieces as an adherend, and 50 g of treatment agent (a) was applied to this adherend. The adhesive (b) is then applied to the treated surface in an overlapping layer of 350 g/m". A 40 x 50 x 5.5 mm lauan plywood having a specific gravity of 0.45±0.02 and a moisture content of IO±1% is bonded to this coated surface so that the fiber direction of the plywood surface and the fiber direction of the Stainless Steel material are orthogonal. Deposition time 3 molecules i, °IO
Press at kg/cm2 for 1 minute. Immediately after depressurization, the splitting strength was measured using a tensile tester manufactured by Toyo Baudouin Co., Ltd. at a tensile rate of 5') 100 mm.
上記試験は20℃で行った。単位はkgである。The above test was conducted at 20°C. The unit is kg.
(5) 圧縮せん断接着強さの測定
比重0.65±0.05、含水率11±1%のカバ材を
150X200XIOmmに切断し被着材とした。被着
材の片面に処理剤(a)を50g/m2塗付し乾燥させ
る。次に該処理面に接着剤(b)を350 g/m”重
ねて塗付し、他方の被着材を直ちに貼り合わせ12kg
/cm”で24時間圧締する。20℃で3日養生後、J
IS・K−6852r接着剤の圧締せん断接着強さ試験
方法」に準じて試験片を作製し、(株)森試験機製作所
製のアムスラー型試験機を用いて荷重速度、毎分900
kgで圧縮せん断強さを測定した。単位はk g /
c m”、0内は木破率%である。試験片の処理はJ
Is−に−6801rユリア樹脂木材接着剤」およびJ
Is−に−6802[フェノール樹脂木材接着剤」に
よった。(5) Measurement of compression shear adhesive strength A cover material having a specific gravity of 0.65±0.05 and a water content of 11±1% was cut into a size of 150×200×IO mm and used as an adherend. Apply treatment agent (a) at 50 g/m2 to one side of the adherend and dry. Next, apply adhesive (b) in layers of 350 g/m" to the treated surface, and immediately attach the other adherend to 12 kg of adhesive.
/cm" for 24 hours. After curing for 3 days at 20℃, J
A test piece was prepared in accordance with the IS・K-6852r Adhesive Pressure Shear Adhesive Strength Test Method, and was tested at a loading rate of 900 per minute using an Amsler type testing machine manufactured by Mori Shikenki Seisakusho Co., Ltd.
Compressive shear strength was measured in kg. The unit is kg/
cm”, the value within 0 is the wood breakage percentage.The treatment of the test piece was J.
IS-N-6801R urea resin wood adhesive” and J
Is-ni-6802 [phenolic resin wood adhesive].
実施例1〜7、比較例1〜6を第1表に、実施例8〜1
0、比較例7〜8を第2表に、実施例11〜13、比較
例9〜lOを第2表に、実施例14、比較例ll−13
を第4表に、実施例15〜21を表5表に表わす。Examples 1 to 7 and Comparative Examples 1 to 6 are shown in Table 1, Examples 8 to 1
0, Comparative Examples 7-8 are in Table 2, Examples 11-13, Comparative Examples 9-1O are in Table 2, Example 14, Comparative Example ll-13
are shown in Table 4, and Examples 15 to 21 are shown in Table 5.
接着剤(b):イミド化合物水溶液(イソパン06、イ
ミド変性率42%、固形
分40%) 31部
0668 30部
LX−43023部
MS−10016部
TETRAD−X 5部
処理剤(a):グリオキザール 15g/ヘキサメチレ
ンテトラミン 5部/水
80部
イミド化合物水溶液:イソパン06、イミド変性率42
%、固形分40%
処理剤(a)
接着剤(b)
:グリオキザール 15部/ヘキサ
メヂレンテトラミン 5部/水
80部
:イミド化合物水溶液(イソパン
06 固形分40%) 28部
5N−30758部
NS−10016部
TETRAD−X 2.5部
TETRAD−C2,5部
処理剤(a):
接着剤(b):
グリオキザール 15部/ヘキサ
メチレンテトラミン 5部/水
80部
イミド化合物水溶液(イソパン
06 固形分40%) 28部
SBR(r0668J
またはr61:2+) 56部
NS−10016部
TETRAD−X 5部
(発明の効果)
本発明は主として木質材料の接着に係わるもので、その
目的とする所は経済的にも有利な極めて短時間の接着方
法にあり、その効果は優れた接着工程とそれに用いるn
徴ある接着剤組成に預かるところが大きい。本発明の接
着方法は特に高度な耐水性を要求するフラッシュパネル
の接着分野において実用上の価値が極めて高いと言える
。Adhesive (b): Imide compound aqueous solution (isopane 06, imide modification rate 42%, solid content 40%) 31 parts 0668 30 parts LX-43023 parts MS-10016 parts TETRAD-X 5 parts Treatment agent (a): Glyoxal 15 g /Hexamethylenetetramine 5 parts/Water 80 parts Imide compound aqueous solution: Isopane 06, imide modification rate 42
%, solid content 40% Treatment agent (a) Adhesive (b): Glyoxal 15 parts/Hexamylenetetramine 5 parts/Water 80 parts: Imide compound aqueous solution (isopane 06 solid content 40%) 28 parts 5N-30758 parts NS-100 16 parts TETRAD-X 2.5 parts TETRAD-C2, 5 parts Treatment agent (a): Adhesive (b): Glyoxal 15 parts/hexamethylenetetramine 5 parts/water 80 parts Imide compound aqueous solution (isopane 06 solid content 40%) 28 parts SBR (r0668J or r61:2+) 56 parts NS-10016 parts TETRAD-X 5 parts (Effects of the invention) The present invention mainly relates to adhesion of wood materials, and its purpose is to achieve economical It is an extremely short-time bonding method that is advantageous for
This is largely due to the unique adhesive composition. It can be said that the adhesion method of the present invention has extremely high practical value, particularly in the field of adhesion of flash panels that require a high degree of water resistance.
手続補正口
(1)明細書第3頁第2行の「イミド基を塗布する」昭
和63年lO月6 日
特許庁長官 吉 1)文 N 殿
1、事件の表示
昭和63年特許願第209461号
2、発明の名称
接着方法
3、補正をする者
事件との関係 特許出願人
名 称 ミサワセラミンクケミカル株式会社4、代理人
〒107
5、補正命令の日付
な し
別紙のとおり
を、
rイミド基を有する天然もしくは合成高分子水溶液また
はジアルデヒド化合物の水溶液を塗布する」と訂正する
。Procedural amendment entry (1) "Coating an imide group" on page 3, line 2 of the specification, 10/6, 1985, Director General of the Patent Office, Yoshi 1) Written by Mr. N. 1, Indication of the case, 1988 Patent Application No. 209461 No. 2, Invention name adhesion method 3, Relationship with the case of the person making the amendment Patent applicant name Misawa Ceraminck Chemical Co., Ltd. 4, Agent 107 5, No date of amendment order As shown in the attached document, r-imide group "Applying an aqueous solution of a natural or synthetic polymer or an aqueous solution of a dialdehyde compound having a
(2)明細書第3頁第15行の「片方のみへ処理」を、 「片方のみへの処理」と訂正する。(2) “Process to only one side” on page 3, line 15 of the specification, Correct it to "processing for only one side".
(3)明細書環5亘!17行の「遅」を、「速」と訂正
する。(3) Specification ring 5 times! Correct "slow" in line 17 to "fast".
(4)明細書第6頁第6行の「場合ににJを、「場合に
」と訂正する。(4) On page 6, line 6 of the specification, ``J in case'' is corrected to ``in case''.
(5)明細書第11頁末行のrサンメチレン」を、「サ
メチレン」と訂正する。(5) "r-samethylene" at the end of page 11 of the specification is corrected to "sameethylene."
(6)明細書第13頁第2行のrLZJを、rLXJと
訂正する。(6) rLZJ on page 13, line 2 of the specification is corrected to rLXJ.
(7)明細書第15頁第1O行のrloを第2表に」を
、
「10を第3表に」と訂正する。(7) "rlo in Table 2" on page 15, line 1 O of the specification is corrected to "10 in Table 3."
Claims (1)
のち、該塗布面の上に接着剤(b)を塗布し、これに他
方の被着材を貼り合わせて圧締することから成り、該処
理剤(a)が5〜25重量%のグリオキザールおよび1
〜10重量%のヘキサメチレンテトラミンを含む水溶液
であり、該接着剤(b)が(1)分子量8〜9×10^
4のイソブチレン−無水マレイン酸共重合物をイミド変
性率30〜50モル%としたイミド化合物20〜40重
量部および(2)カルボキシ変性スチレン−ブタジエン
系ラテックス固形分として60〜80重量部および必要
に応じて上記イミド化合物(1)と上記ラテックス(2
)の固形分との合計量に基いて1〜30重量%の(3)
多官能エポキシ化食物を含む水性組成物である、ことを
特徴とする被着材を作業性良く且つ極めて短時間で接着
する方法。After applying the treatment agent (a) to the surface of one adherend and drying it, apply the adhesive (b) on the applied surface, and bond the other adherend to this and press it. The treatment agent (a) contains 5 to 25% by weight of glyoxal and 1
It is an aqueous solution containing ~10% by weight of hexamethylenetetramine, and the adhesive (b) has (1) a molecular weight of 8 to 9 x 10^
20 to 40 parts by weight of an imide compound in which the isobutylene-maleic anhydride copolymer of 4 has an imide modification rate of 30 to 50 mol%, and (2) 60 to 80 parts by weight of carboxy-modified styrene-butadiene latex solid content, and as necessary. Accordingly, the imide compound (1) and the latex (2)
) from 1 to 30% by weight based on the total amount of solids (3)
A method for bonding adherends with good workability and in an extremely short time, characterized in that the composition is an aqueous composition containing a polyfunctional epoxidized food.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63209461A JP2537984B2 (en) | 1988-08-25 | 1988-08-25 | Adhesion method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63209461A JP2537984B2 (en) | 1988-08-25 | 1988-08-25 | Adhesion method |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0258583A true JPH0258583A (en) | 1990-02-27 |
JP2537984B2 JP2537984B2 (en) | 1996-09-25 |
Family
ID=16573257
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63209461A Expired - Fee Related JP2537984B2 (en) | 1988-08-25 | 1988-08-25 | Adhesion method |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2537984B2 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08113762A (en) * | 1994-10-17 | 1996-05-07 | Misawa Homes Co Ltd | Formation of the part to be bonded |
WO2000039237A1 (en) * | 1998-12-28 | 2000-07-06 | Bridgestone Corporation | Adhesive composition, resin material, rubber article and pneumatic tire |
JP2000248254A (en) * | 1998-12-28 | 2000-09-12 | Bridgestone Corp | Adhesive composition, resin material, rubber article and pneumatic tire |
JP2001019927A (en) * | 1999-07-06 | 2001-01-23 | Bridgestone Corp | Adhesive composition, resin material treated therewith and rubber article reinforced with the resin material |
JP2001049212A (en) * | 1999-08-11 | 2001-02-20 | Konishi Co Ltd | Two-part-separately-applying fast-curing aqueous adhesive |
JP2008304748A (en) * | 2007-06-08 | 2008-12-18 | Brother Ind Ltd | Image forming apparatus |
JP2011241402A (en) * | 2011-06-27 | 2011-12-01 | Bridgestone Corp | Adhesive composition, resin material, rubber article and pneumatic tire |
-
1988
- 1988-08-25 JP JP63209461A patent/JP2537984B2/en not_active Expired - Fee Related
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08113762A (en) * | 1994-10-17 | 1996-05-07 | Misawa Homes Co Ltd | Formation of the part to be bonded |
WO2000039237A1 (en) * | 1998-12-28 | 2000-07-06 | Bridgestone Corporation | Adhesive composition, resin material, rubber article and pneumatic tire |
JP2000248254A (en) * | 1998-12-28 | 2000-09-12 | Bridgestone Corp | Adhesive composition, resin material, rubber article and pneumatic tire |
JP2001019927A (en) * | 1999-07-06 | 2001-01-23 | Bridgestone Corp | Adhesive composition, resin material treated therewith and rubber article reinforced with the resin material |
JP2001049212A (en) * | 1999-08-11 | 2001-02-20 | Konishi Co Ltd | Two-part-separately-applying fast-curing aqueous adhesive |
JP2008304748A (en) * | 2007-06-08 | 2008-12-18 | Brother Ind Ltd | Image forming apparatus |
JP2011241402A (en) * | 2011-06-27 | 2011-12-01 | Bridgestone Corp | Adhesive composition, resin material, rubber article and pneumatic tire |
Also Published As
Publication number | Publication date |
---|---|
JP2537984B2 (en) | 1996-09-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
LAPS | Cancellation because of no payment of annual fees |