JPH032469B2 - - Google Patents
Info
- Publication number
- JPH032469B2 JPH032469B2 JP60041710A JP4171085A JPH032469B2 JP H032469 B2 JPH032469 B2 JP H032469B2 JP 60041710 A JP60041710 A JP 60041710A JP 4171085 A JP4171085 A JP 4171085A JP H032469 B2 JPH032469 B2 JP H032469B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- acrylic
- urethane
- copolymer
- rubber
- 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 - Lifetime
Links
- 239000000853 adhesive Substances 0.000 claims description 41
- 230000001070 adhesive effect Effects 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 9
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 14
- -1 polypropylene Polymers 0.000 description 12
- 229920000098 polyolefin Polymers 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000005060 rubber Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003522 acrylic cement Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 239000004636 vulcanized rubber Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229920005672 polyolefin resin Polymers 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 229920003002 synthetic resin Polymers 0.000 description 5
- 239000000057 synthetic resin Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 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 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 238000003851 corona treatment Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WTXXSZUATXIAJO-OWBHPGMISA-N (Z)-14-methylpentadec-2-enoic acid Chemical compound CC(CCCCCCCCCC\C=C/C(=O)O)C WTXXSZUATXIAJO-OWBHPGMISA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- SNZYOYGFWBZAQY-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.CCC(CO)(CO)CO SNZYOYGFWBZAQY-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- BJUPZVQSAAGZJL-UHFFFAOYSA-N 2-methyloxirane;propane-1,2,3-triol Chemical compound CC1CO1.OCC(O)CO BJUPZVQSAAGZJL-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000921 polyethylene adipate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920006124 polyolefin elastomer Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 238000010998 test method Methods 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Landscapes
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
発明の目的
（産業上の利用分野）
本発明はポリオレフイン系樹脂やポリオレフイ
ン系加硫ゴムからなる各種基材の表面に塗布する
粘着剤に関するものである。
（従来の技術）
エチレン―プロピレン―ジエン三元共重合ゴム
（EPDM）やエチレン―プロピレン共重合ゴム
（EPM）などのポリオレフイン系加硫ゴムあるい
はポリプロピレン（PP）やポリエチレン（PE）
などのポリオレフイン系合成樹脂は天然ゴム
（NR）やスチレン―ブタジエン共重合ゴム
（SBR）、ポリブタジエンゴム（BR）、イソブチ
レン−イソプレン共重合ゴム（IIR）、ポリクロ
ロプレンゴム（CR）、アクリロニトリル―ブタジ
エン共重合ゴム（NBR）、ポリイソプレンゴム
（IR）などの合成ゴムあるいはABS樹脂、ポリス
チレン樹脂（PS）、アクリロニトリル―スチレン
共重合樹脂（AS）、エチレン―酢ビ共重合樹脂
（EVA）などの合成樹脂に比べ、耐候性、耐老化
性、性オゾン性などに卓越した性能を示し、優秀
な特徴を備えたゴム、合成樹脂であるため、現在
では多方面で使用されるようになつた。
（発明が解決しようとする問題点）
ところが、このEPDM、EPMなどのポリオレ
フイン系加硫ゴムやPP、PEなどのポリオレフイ
ン系樹脂はその分子の主鎖中に極性基を含まない
ことから、その上に粘着剤を塗布しても生じた塗
膜は剥離しやすく、そのためこれらポリオレフイ
ン系のゴムや樹脂相互のあるいはゴムと樹脂との
もしくは金属・プラスチツクなど他物質との粘着
は困難を極めているのが現状である。
このような欠点に対しては従来、すでに数々の
対応策が試みられてはいるが、いまだ満足な解決
策は見出されていない。
本発明者は上記問題点の解決を目的として、ポ
リオレフイン系加硫ゴムやポリオレフイン系樹脂
の粘着剤につき長年の研究を続けた結果、これら
の基材に対して充分な密着力を備えた粘着剤を見
出すに至つた。
発明の構成
（問題点を解決するための手段）
本発明者はポリオレフイン系の加硫ゴムや樹脂
の表面に塗布する粘着剤として、炭素数18以下の
アクリル誘導体またはメタクリル誘導体と活性水
素含有化合物との共重合体に対し、ポリオールと
トリエタノールアミンの混合物をポリイソシアネ
ートと反応させて得られた末端にNCO基を備え
たポリウレタンを、両者の固形分重量比が100／
0.007〜500となるように混合してなる粘着剤を案
出することにより、上記問題点の解決を図つた。
（作用）
炭素数18以下のアクリル誘導体またはメタクリ
ル誘導体と活性水素含有化合物との共重合体に上
記特定組成よりなるポリウレタンを所定割合混合
してなるこの粘着剤は、極性基を含むことから反
応性に富んでいる。
そこで、この粘着剤をポリオレフイン系の加硫
ゴムや樹脂に塗布し、ポリオレフイン相互のもし
くは金属・プラスチツクなどの他物質との接着に
用いれば、強固な密着力を得ることができる。
また、前記共重合体とポリウレタンとの固形分
重量比を100／0.007〜500としたことにより、ポ
リウレタンの固形分重量比が0.007以下となつて
粘着力が極端に低下することや、逆に500を越え
て硬化時間が極端に長くなるということが確実に
防止される。
（実施例）
以下、この粘着剤につき実施例をあげて説明す
る。
炭素数18以下のアクリル誘導体とはアクリル酸
の外、メチルアクリレート、エチルアクリレー
ト、ｎ―ブチルアクリレート、iso―ブチルアク
リレート、２―エチルヘキシルアクリレート、イ
ソデシルアクリレート、ラウリルアクリレート、
C12〜C13混合アルキルアクリレート、ステアリル
アクリレートおよびC10〜C18混合アルキルアクリ
レートなどである。
また、炭素数18以下のメタクリル誘導体とはメ
タクリル酸の外、メチルメタクリレート、エチル
メタクリレート、ｎ−ブチルメタクリレート、
iso―ブチルメタクリレート、２―エチルヘキシ
ルメタクリレート、イソデシルメタクリレート、
ラウリルメタクリレート、C12〜C13混合アルキル
メタクリレート、ステアリルメタクリレート、
C10〜C18混合アルキルメタクリレートなどであ
る。
活性水素含有化合物とはアクリル酸、メタクリ
ル酸の外、２―ヒドロキシエチルアクリレート、
２―ヒドロキシエチルメタクリレート、２―ヒド
ロキシプロピルアクリレート、２―ヒドロキシプ
ロピルメタクリレートおよびマレイン酸、無水マ
レイン酸、フマル酸、シトラコン酸、無水シトラ
コン酸、イタコン酸、無水イタコン酸が例示でき
る。
上記炭素数18以下のメタクリル誘導体またはア
クリル誘導体を常法により活性水素含有化合物と
共重合させれば、活性水素含有アクリル粘着剤を
得ることができる。また、このときメタクリル誘
導体とアクリル誘導体とを混合して活性水素含有
化合物と共重合させてもよい。
次に、ポリウレタン（以下、単にウレタンとい
う）とはポリオールとトリエタノールアミンとの
混合物をポリイソシアネートと反応させて得られ
た、末端にNCO基を備えたものである。
ポリオールは少なくとも二官能基を備えたポリ
エーテルポリオールやポリエステルポリオールな
どが使用される。
ポリエーテルポリオールの例としてはポリエチ
レングリコール、ポリプロピレングリコール、ポ
リテトラメチレングリコール、ポリ（プロピレン
オキサイド―エチレンオキサイド）グリコールな
どのようなジオールやプロピレンオキサイド―グ
リセリン反応物、プロピレンオキサイド―トリメ
チロールプロパン反応物などがある。
ポリエステルポリオールはポリエチレンアジペ
ート、ポリブチレンアジペート、ポリエチレンブ
チレンアジペートなどのアジピン酸エステルが例
示できる。
また、ポリイソシアネートはトリレンジイソシ
アネート、４，4′―ジフエニルメタンジイソシア
ネート、水添４，4′―ジフエニルメタンジイソシ
アネート、１，５―ナフタレンジイソシアネー
ト、キシレンジイソシアネート、水添キシレンジ
イソシアネート、イソホロンジイソシアネート、
１，６―ヘキサメチレンジイソシアネートなどで
ある。
上記ウレタンを調整するにはトリクロルエチレ
ンなどの溶剤に溶解させた上記ポリオール、イソ
シアネートおよびトリエタノールアミンを常法に
より乾燥窒素ガス中で80℃、３時間反応させれば
よく、この反応によつて末端にNCO基を備えた
ウレタンを得ることができる。
この反応におけるポリオールとポリイソシアネ
ートとの配合比は当量比でOH／NCO＝１／1.5
〜７であることが好ましい。
NCOが1.5当量未満では粘着力が低下し、また
７当量以上加えても粘着力は向上しない。
また、ポリオールとトリエタノールアミンとの
配合比はポリオール１モルに対してトリエタノー
ルアミン0.05〜２モルである。
前記メタクリル誘導体および／またはアクリル
誘導体と活性水素含有化合物との共重合体である
活性水素含有アクリル粘着剤と上記ウレタンとを
溶剤中で混合したものが本発明の粘着剤である。
これらの混合比は活性水素含有アクリル粘着剤
の固形分100重量部に対してウレタン固形分が
0.007〜500重量部であることが好ましく、さらに
好ましくはウレタン固形分が0.007〜100重量部で
ある。
ウレタン固形分が0.007重量部以下では粘着力
が低下し、500重量部以上では粘着力は向上せず、
また硬化時間が長くなつてしまう。
なお、混合の際使用する溶剤はベンゼン、トル
エン、キシレンなどの芳香族炭化水素、メチルエ
チルケトン、メチルイソプロピルケトン、メチル
イソブチルケトンなどのケトン類、酢酸メチル、
酢酸エチル、酢酸イソプロピル、酢酸イソブチル
などの酢酸エステルあるいはｎ―ヘキサン、シク
ロヘキサンなどの飽和炭化水素である。
上記組成からなる粘着剤をポリオレフイン系樹
脂やポリオレフイン系加硫ゴムからなる各種基材
の表面に塗布するにはデイツピング、スプレー、
ハケ塗りなどの通常の塗装方法を使用するだけで
よく、特殊な設備は必要ではない。
また粘着剤の塗布に先立ち、基材にコロナ放電
処理あるいはプラズマ処理を行つて、その表面を
活性化してもよい。
このコロナ放電処理は一例として、電力：
1kW、電極：ナイフ型、電極長さ：300mm、電極
―基材間隔：１mmの条件で行うことができる。
次に、以下の実施例により本発明の粘着剤の密
着力を調べた。
まず、表―１のEPDM配合物を160℃で30分加
硫処理し、２mm厚の試験片を調整した。
（以下、表中の部はすべて重量部である。）
Object of the Invention (Field of Industrial Application) The present invention relates to an adhesive that is applied to the surface of various substrates made of polyolefin resin or polyolefin vulcanized rubber. (Prior technology) Polyolefin vulcanized rubber such as ethylene-propylene-diene ternary copolymer rubber (EPDM) and ethylene-propylene copolymer rubber (EPM), or polypropylene (PP) and polyethylene (PE)
Polyolefin-based synthetic resins such as natural rubber (NR), styrene-butadiene copolymer rubber (SBR), polybutadiene rubber (BR), isobutylene-isoprene copolymer rubber (IIR), polychloroprene rubber (CR), acrylonitrile-butadiene etc. Synthetic rubbers such as polymerized rubber (NBR) and polyisoprene rubber (IR), or synthetic resins such as ABS resin, polystyrene resin (PS), acrylonitrile-styrene copolymer resin (AS), and ethylene-vinyl acetate copolymer resin (EVA) Rubber and synthetic resins have superior properties such as weather resistance, aging resistance, and ozone resistance, and are now used in a wide variety of fields. (Problem to be solved by the invention) However, polyolefin vulcanized rubbers such as EPDM and EPM, and polyolefin resins such as PP and PE do not contain polar groups in the main chain of their molecules. Even if an adhesive is applied to the adhesive, the resulting coating film is likely to peel off, making it extremely difficult for these polyolefin rubbers and resins to adhere to each other, to rubber and resin, or to other materials such as metals and plastics. This is the current situation. A number of countermeasures have been attempted to address these drawbacks, but no satisfactory solution has yet been found. In order to solve the above problems, the inventors of the present invention have conducted many years of research into adhesives for polyolefin vulcanized rubber and polyolefin resins, and have developed an adhesive that has sufficient adhesion to these base materials. I came to find out. Structure of the Invention (Means for Solving Problems) The present inventor has developed an acrylic derivative or methacrylic derivative having 18 or less carbon atoms and an active hydrogen-containing compound as an adhesive to be applied to the surface of polyolefin vulcanized rubber or resin. A polyurethane with an NCO group at the end obtained by reacting a mixture of polyol and triethanolamine with polyisocyanate was added to the copolymer with a solid content weight ratio of 100/1.
The above-mentioned problem was solved by devising a pressure-sensitive adhesive made by mixing 0.007 to 500%. (Function) This adhesive is made by mixing a copolymer of an acrylic derivative or methacrylic derivative with 18 or less carbon atoms and an active hydrogen-containing compound with a predetermined proportion of polyurethane having the above-mentioned specific composition, and is reactive because it contains a polar group. rich in Therefore, if this adhesive is applied to a polyolefin-based vulcanized rubber or resin and used to bond the polyolefins to each other or to other materials such as metals and plastics, strong adhesion can be obtained. In addition, by setting the solid content weight ratio of the copolymer and polyurethane to 100/0.007 to 500, the solid content weight ratio of the polyurethane becomes 0.007 or less, resulting in an extremely low adhesive strength, It is reliably prevented that the curing time becomes extremely long. (Example) This adhesive will be described below by giving examples. Acrylic derivatives having 18 or fewer carbon atoms include acrylic acid, methyl acrylate, ethyl acrylate, n-butyl acrylate, iso-butyl acrylate, 2-ethylhexyl acrylate, isodecyl acrylate, lauryl acrylate,
C12 - C13 mixed alkyl acrylate, stearyl acrylate, and C10 - C18 mixed alkyl acrylate. In addition to methacrylic acid, methacrylic derivatives having 18 or fewer carbon atoms include methyl methacrylate, ethyl methacrylate, n-butyl methacrylate,
iso-butyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate,
Lauryl methacrylate, C12 - C13 mixed alkyl methacrylate, stearyl methacrylate,
C10 - C18 mixed alkyl methacrylates and the like. Active hydrogen-containing compounds include acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate,
Examples include 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, and maleic acid, maleic anhydride, fumaric acid, citraconic acid, citraconic anhydride, itaconic acid, and itaconic anhydride. An active hydrogen-containing acrylic pressure-sensitive adhesive can be obtained by copolymerizing the above-mentioned methacrylic derivative or acrylic derivative having 18 or less carbon atoms with an active hydrogen-containing compound by a conventional method. Further, at this time, the methacrylic derivative and the acrylic derivative may be mixed and copolymerized with the active hydrogen-containing compound. Next, polyurethane (hereinafter simply referred to as urethane) is obtained by reacting a mixture of polyol and triethanolamine with polyisocyanate, and has NCO groups at the ends. As the polyol, a polyether polyol or a polyester polyol having at least two functional groups is used. Examples of polyether polyols include diols such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, poly(propylene oxide-ethylene oxide) glycol, propylene oxide-glycerin reaction products, propylene oxide-trimethylolpropane reaction products, etc. be. Examples of polyester polyols include adipic acid esters such as polyethylene adipate, polybutylene adipate, and polyethylene butylene adipate. In addition, polyisocyanates include tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, hydrogenated 4,4'-diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, xylene diisocyanate, hydrogenated xylene diisocyanate, isophorone diisocyanate,
1,6-hexamethylene diisocyanate and the like. To prepare the above urethane, the above polyol, isocyanate and triethanolamine dissolved in a solvent such as trichloroethylene may be reacted in a dry nitrogen gas at 80°C for 3 hours by a conventional method. A urethane with NCO groups can be obtained. The blending ratio of polyol and polyisocyanate in this reaction is equivalent ratio: OH/NCO = 1/1.5
It is preferable that it is 7. If NCO is less than 1.5 equivalents, the adhesive strength will decrease, and even if 7 equivalents or more is added, the adhesive strength will not improve. The blending ratio of polyol and triethanolamine is 0.05 to 2 moles of triethanolamine per mole of polyol. The adhesive of the present invention is a mixture of the urethane and the active hydrogen-containing acrylic adhesive, which is a copolymer of the methacrylic derivative and/or acrylic derivative and the active hydrogen-containing compound, in a solvent. These mixing ratios are urethane solid content to 100 parts by weight of solid content of active hydrogen-containing acrylic adhesive.
The urethane solid content is preferably 0.007 to 500 parts by weight, and more preferably 0.007 to 100 parts by weight. If the urethane solid content is less than 0.007 parts by weight, the adhesive strength will decrease, and if it is more than 500 parts by weight, the adhesive strength will not improve.
Moreover, the curing time becomes longer. The solvents used during mixing include aromatic hydrocarbons such as benzene, toluene, and xylene, ketones such as methyl ethyl ketone, methyl isopropyl ketone, and methyl isobutyl ketone, methyl acetate,
These are acetate esters such as ethyl acetate, isopropyl acetate, and isobutyl acetate, or saturated hydrocarbons such as n-hexane and cyclohexane. To apply the adhesive consisting of the above composition to the surface of various base materials made of polyolefin resin or polyolefin vulcanized rubber, dipping, spraying,
All you need to do is use normal painting methods, such as brushing, and no special equipment is required. Furthermore, prior to applying the adhesive, the surface of the base material may be activated by subjecting it to corona discharge treatment or plasma treatment. As an example of this corona discharge treatment, electric power:
It can be performed under the following conditions: 1kW, electrode: knife type, electrode length: 300mm, electrode-substrate distance: 1mm. Next, the adhesive strength of the adhesive of the present invention was investigated using the following examples. First, the EPDM composition shown in Table 1 was vulcanized at 160°C for 30 minutes to prepare a 2 mm thick test piece. (All parts in the table below are parts by weight.)
【表】
この試験片の表面に前記の条件でコロナ放電処
理を行つた。
次に、この試験片の表面に活性水素含有アクリ
ル粘着剤とウレタンとの混合物からなる粘着剤を
塗布し、100℃で２分間乾燥させた。
この粘着剤を塗布した試験片同士を貼り合わせ
て室温で20日間放置後、引張り速度30mm／分の条
件で剪断試験を行つた。
使用した粘着剤中のウレタンの組成、ウレタン
とアクリル粘着剤との混合比および剪断強さを表
―２に示す。
実施例１〜15で使用したアクリル粘着剤はいず
れも、無水マレイン酸とｎ―ブチルアクリレート
をトルエン／シクロヘキサン／酢酸エチル＝１／
１／１からなる混合溶剤中で共重合させた酸価＝
20〜25、固形分37％の活性水素含有アクリル粘着
剤である。
また、各実施例中のウレタンはポリオールとト
リエタノールアミンとの混合比やイソシアネート
の種類などを適宜変えて調整したものである。
例えば、実施例１のウレタンはトリクロルエチ
レン中において、ポリプロピレングリコール（分
子量＝3000）１モルに対しトリエタノールアミン
0.7モルを加え、さらにOH／NCO＝１／４とな
るように４，4′―ジフエニルメタンジイソシアネ
ートを加えたものを乾燥窒素ガス中で80℃、３時
間反応させ、得られた溶液（固形分83％）１部に
対しトルエン19部を加えて調整したものである。
また、実施例１の粘着剤は上記アクリル粘着剤
100部に対し、このウレタン１部を混合したもの
である。
なお、表―２中の比較例１はアクリル粘着剤の
みを使用した場合であり、その剪断強さはほぼ０
であつた。
また、比較例２および３の粘着剤は硬化時間が
長すぎて剪断強さの測定ができなかつた。
この剪断試験の結果から、実施例１〜15の粘着
剤は極めて強固な粘着力を備えていることがわか
る。[Table] The surface of this test piece was subjected to corona discharge treatment under the above conditions. Next, an adhesive consisting of a mixture of an active hydrogen-containing acrylic adhesive and urethane was applied to the surface of this test piece, and the adhesive was dried at 100°C for 2 minutes. The test pieces coated with this adhesive were pasted together and allowed to stand at room temperature for 20 days, after which a shear test was conducted at a pulling speed of 30 mm/min. Table 2 shows the composition of the urethane in the adhesive used, the mixing ratio of urethane and acrylic adhesive, and the shear strength. The acrylic adhesives used in Examples 1 to 15 all contained maleic anhydride and n-butyl acrylate in toluene/cyclohexane/ethyl acetate = 1/
Acid value copolymerized in a mixed solvent consisting of 1/1 =
20-25, an active hydrogen-containing acrylic adhesive with a solid content of 37%. Further, the urethane in each example was prepared by appropriately changing the mixing ratio of polyol and triethanolamine, the type of isocyanate, etc. For example, the urethane of Example 1 is triethanolamine per mol of polypropylene glycol (molecular weight = 3000) in trichlorethylene.
0.7 mol was added, and 4,4'-diphenylmethane diisocyanate was added so that OH/NCO = 1/4, and the mixture was reacted at 80°C for 3 hours in dry nitrogen gas. It was adjusted by adding 19 parts of toluene to 1 part (83%). In addition, the adhesive of Example 1 was the above-mentioned acrylic adhesive.
This is a mixture of 1 part of this urethane per 100 parts. In addition, Comparative Example 1 in Table 2 is a case where only acrylic adhesive was used, and its shear strength was almost 0.
It was hot. Moreover, the curing time of the adhesives of Comparative Examples 2 and 3 was too long, so that the shear strength could not be measured. The results of this shear test show that the adhesives of Examples 1 to 15 have extremely strong adhesive strength.
ポリエチレンの５倍発泡体からなるスポンジを
基材とし、この表面に前記活性水素含有アクリル
粘着剤とウレタンとからなる粘着剤を塗布した。
次に、この基材をアクリル塗装鉄板に貼り付け
て24時間放置後、引張り速度30mm／分の条件で剪
断強さを調べた。
粘着剤の組成およびそれぞれの剪断強さを表―
３に示す。なお、表―３中の比較例４はアクリル
粘着剤を単独で使用したものであり、その剪断強
さはほぼ０であつた。
比較例５および６の粘着剤は硬化時間が長すぎ
て剪断強さの測定ができなかつた。
また、比較例７は市販の両面粘着テープ（日東
電工＃500）を使用したものである。
A sponge made of a 5x polyethylene foam was used as a base material, and an adhesive made of the active hydrogen-containing acrylic adhesive and urethane was applied to the surface of the sponge. Next, this base material was attached to an acrylic-coated iron plate and left for 24 hours, and then the shear strength was examined at a tensile speed of 30 mm/min. The composition of adhesives and their respective shear strengths are shown.
Shown in 3. In addition, Comparative Example 4 in Table 3 uses an acrylic adhesive alone, and its shear strength was approximately 0. The curing time of the adhesives of Comparative Examples 5 and 6 was so long that the shear strength could not be measured. Comparative Example 7 uses a commercially available double-sided adhesive tape (Nitto Denko #500).
【表】
表―３の剪断試験の結果から、実施例16〜30の
粘着剤はいずれも極めて強固な密着力を備え、前
記モールの取付構造に用いて充分な効果を発揮す
ることがわかつた。
第１図は両面粘着テープ４の基材５に本発明の
粘着剤３を塗布したモール２の取付構造である。
なおこのとき、基材５のモール２側にはこの粘
着剤３に代えてクロロプレンゴム系、ウレタン系
などの粘着剤を用いてもよい。
さらに、この粘着剤３を用いた取付構造は自動
車ボデイ１へのモール２の装着のみならず、一般
に両面粘着テープ４を介して合成樹脂材料を金属
その他の部材に取り付ける際にも具体化すること
ができる。
発明の効果
以上詳述したように、本発明の粘着剤はこれを
ポリオレフイン系の加硫ゴムや樹脂に塗布し、ポ
リオレフイン相互の、もしくは金属や各種の合成
樹脂との接着に用いれば、強固な密着力を得るこ
とができるという効果を発揮し、広範な用途に利
用可能な優れた発明である。[Table] From the shear test results shown in Table 3, it was found that the adhesives of Examples 16 to 30 all had extremely strong adhesion and were sufficiently effective when used in the mounting structure of the molding. . FIG. 1 shows a mounting structure of a molding 2 in which a base material 5 of a double-sided adhesive tape 4 is coated with the adhesive 3 of the present invention. At this time, instead of the adhesive 3, a chloroprene rubber adhesive, a urethane adhesive, or the like may be used on the side of the molding 2 of the base material 5. Furthermore, the mounting structure using this adhesive 3 can be applied not only to attaching the molding 2 to the automobile body 1, but also generally when attaching a synthetic resin material to metal or other members via double-sided adhesive tape 4. Can be done. Effects of the Invention As detailed above, the adhesive of the present invention can be applied to polyolefin-based vulcanized rubber or resin and used for adhesion between polyolefins or with metals and various synthetic resins. This is an excellent invention that can be used for a wide range of purposes, and has the effect of providing good adhesion.
第１図は本発明の粘着剤を用いたモールの取付
構造を示す断面図、また第２図は従来のモールの
取付構造を示す断面図である。
１…自動車ボデイ、２…モール、３…粘着剤。
FIG. 1 is a sectional view showing a molding mounting structure using the adhesive of the present invention, and FIG. 2 is a sectional view showing a conventional molding mounting structure. 1...Automobile body, 2...Mall, 3...Adhesive.
Claims (1)
リル誘導体と活性水素含有化合物との共重合体に
対して下記ポリウレタン(A)を前記共重合体とポリ
ウレタン(A)との固形分重量比が100／0.007〜500
となるように混合されていることを特徴とする粘
着剤。 (A) ポリオールとトリエタノールアミンの混合物
をポリイソシアネートと反応させて得られた末
端にNCO基を備えたポリウレタン。[Claims] 1. For a copolymer of an acrylic derivative or methacrylic derivative having 18 or less carbon atoms and an active hydrogen-containing compound, the following polyurethane (A) is added to the solid weight of the copolymer and polyurethane (A). Ratio is 100/0.007~500
An adhesive characterized by being mixed so that (A) Polyurethane with terminal NCO groups obtained by reacting a mixture of polyol and triethanolamine with polyisocyanate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4171085A JPS61200185A (en) | 1985-03-01 | 1985-03-01 | Pressure-sensitive adhesive |
| DE19863601272 DE3601272A1 (en) | 1985-01-17 | 1986-01-17 | Adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4171085A JPS61200185A (en) | 1985-03-01 | 1985-03-01 | Pressure-sensitive adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61200185A JPS61200185A (en) | 1986-09-04 |
| JPH032469B2 true JPH032469B2 (en) | 1991-01-16 |
Family
ID=12615978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4171085A Granted JPS61200185A (en) | 1985-01-17 | 1985-03-01 | Pressure-sensitive adhesive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61200185A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6393620A (en) * | 1986-10-06 | 1988-04-23 | Toyoda Gosei Co Ltd | Installation structure of automobile parts |
| JP5474297B2 (en) * | 2007-12-27 | 2014-04-16 | 日本カーバイド工業株式会社 | Adhesive composition and adhesive sheet |
| KR102086441B1 (en) * | 2012-03-30 | 2020-03-09 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | Urea-based and urethane-based pressure sensitive adhesive blends |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS539838A (en) * | 1976-07-14 | 1978-01-28 | Pratt & Lambert Inc | Adhesive and adhesion method |
| JPS5580425A (en) * | 1978-12-07 | 1980-06-17 | Usm Corp | Improved adhesive |
| JPS5695970A (en) * | 1979-12-28 | 1981-08-03 | Yokohama Rubber Co Ltd:The | Adhesive and use thereof |
| JPS56125471A (en) * | 1980-03-05 | 1981-10-01 | Nitto Electric Ind Co Ltd | Pressure-sensitive adhesive composition |
| JPS56136867A (en) * | 1980-03-31 | 1981-10-26 | Toyoda Gosei Co Ltd | Adhesive for inserting plastic bead |
| JPS56155271A (en) * | 1980-04-30 | 1981-12-01 | Toyoda Gosei Co Ltd | Adhesive for synthetic resin molding |
-
1985
- 1985-03-01 JP JP4171085A patent/JPS61200185A/en active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS539838A (en) * | 1976-07-14 | 1978-01-28 | Pratt & Lambert Inc | Adhesive and adhesion method |
| JPS5580425A (en) * | 1978-12-07 | 1980-06-17 | Usm Corp | Improved adhesive |
| JPS5695970A (en) * | 1979-12-28 | 1981-08-03 | Yokohama Rubber Co Ltd:The | Adhesive and use thereof |
| JPS56125471A (en) * | 1980-03-05 | 1981-10-01 | Nitto Electric Ind Co Ltd | Pressure-sensitive adhesive composition |
| JPS56136867A (en) * | 1980-03-31 | 1981-10-26 | Toyoda Gosei Co Ltd | Adhesive for inserting plastic bead |
| JPS56155271A (en) * | 1980-04-30 | 1981-12-01 | Toyoda Gosei Co Ltd | Adhesive for synthetic resin molding |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61200185A (en) | 1986-09-04 |
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