DE2633764C2 - Verfahren zur Herstellung von Kunststoff -Metall-Verbunden - Google Patents
Verfahren zur Herstellung von Kunststoff -Metall-VerbundenInfo
- Publication number
- DE2633764C2 DE2633764C2 DE2633764A DE2633764A DE2633764C2 DE 2633764 C2 DE2633764 C2 DE 2633764C2 DE 2633764 A DE2633764 A DE 2633764A DE 2633764 A DE2633764 A DE 2633764A DE 2633764 C2 DE2633764 C2 DE 2633764C2
- Authority
- DE
- Germany
- Prior art keywords
- polyurethane
- metal
- plastic
- foam
- reaction mixture
- 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
- 238000000034 method Methods 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 239000002905 metal composite material Substances 0.000 title description 2
- 239000002184 metal Substances 0.000 claims description 71
- 229910052751 metal Inorganic materials 0.000 claims description 71
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 37
- 239000005056 polyisocyanate Substances 0.000 claims description 32
- 229920001228 polyisocyanate Polymers 0.000 claims description 32
- 229920003023 plastic Polymers 0.000 claims description 30
- 239000004033 plastic Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- 239000006260 foam Substances 0.000 claims description 27
- 239000011888 foil Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 150000002739 metals Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000002318 adhesion promoter Substances 0.000 claims description 11
- 239000002131 composite material Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 5
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 239000011496 polyurethane foam Substances 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 description 40
- 229920002635 polyurethane Polymers 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- -1 polybiuret Polymers 0.000 description 24
- 229910052782 aluminium Inorganic materials 0.000 description 18
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 18
- 239000006185 dispersion Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 229920000570 polyether Polymers 0.000 description 11
- 239000000853 adhesive Substances 0.000 description 10
- 230000001070 adhesive effect Effects 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 125000002091 cationic group Chemical group 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000005187 foaming Methods 0.000 description 9
- 229920002396 Polyurea Polymers 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 150000004756 silanes Chemical class 0.000 description 8
- 229920006264 polyurethane film Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000013518 molded foam Substances 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000004872 foam stabilizing agent Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000582 polyisocyanurate Polymers 0.000 description 4
- 239000011495 polyisocyanurate Substances 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004873 anchoring Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 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 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 239000002991 molded plastic Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- GGPLWEZGITVTJX-UHFFFAOYSA-N 2,2,4-trimethyl-1,4,2-oxazasilinane Chemical compound CN1CCO[Si](C)(C)C1 GGPLWEZGITVTJX-UHFFFAOYSA-N 0.000 description 1
- IVGRSQBDVIJNDA-UHFFFAOYSA-N 2-(2-aminoethylamino)ethanesulfonic acid Chemical compound NCCNCCS(O)(=O)=O IVGRSQBDVIJNDA-UHFFFAOYSA-N 0.000 description 1
- RZEWIYUUNKCGKA-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;octadecanoic acid Chemical compound OCCNCCO.CCCCCCCCCCCCCCCCCC(O)=O RZEWIYUUNKCGKA-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 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 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
- B05D7/16—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies using synthetic lacquers or varnishes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/16—Metal
- C09J2400/166—Metal in the pretreated surface to be joined
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Laminated Bodies (AREA)
- Casting Or Compression Moulding Of Plastics Or The Like (AREA)
- Molding Of Porous Articles (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2633764A DE2633764C2 (de) | 1976-07-28 | 1976-07-28 | Verfahren zur Herstellung von Kunststoff -Metall-Verbunden |
| US05/817,880 US4160851A (en) | 1976-07-28 | 1977-07-21 | Process for the production of plastics/metal composites |
| CA283,335A CA1094406A (en) | 1976-07-28 | 1977-07-22 | Process for the production of plastics/metal composites |
| GB31274/77A GB1531669A (en) | 1976-07-28 | 1977-07-26 | Process for the production of plastics/metal composites |
| AT0543177A AT364535B (de) | 1976-07-28 | 1977-07-26 | Verfahren zur herstellung von kunststoff-metall-verbunden |
| CH922677A CH625721A5 (enExample) | 1976-07-28 | 1977-07-26 | |
| JP52089379A JPS6026024B2 (ja) | 1976-07-28 | 1977-07-27 | プラスチツク−金属複合材料の製法 |
| FR7723303A FR2359871A1 (fr) | 1976-07-28 | 1977-07-28 | Emploi de dispersions aqueuses de polyurethanne comme agents d'adherence dans la preparation de composites metal-resine a base de polyisocyanate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2633764A DE2633764C2 (de) | 1976-07-28 | 1976-07-28 | Verfahren zur Herstellung von Kunststoff -Metall-Verbunden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2633764B1 DE2633764B1 (de) | 1978-01-05 |
| DE2633764C2 true DE2633764C2 (de) | 1978-09-07 |
Family
ID=5984065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2633764A Expired DE2633764C2 (de) | 1976-07-28 | 1976-07-28 | Verfahren zur Herstellung von Kunststoff -Metall-Verbunden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4160851A (enExample) |
| JP (1) | JPS6026024B2 (enExample) |
| AT (1) | AT364535B (enExample) |
| CA (1) | CA1094406A (enExample) |
| CH (1) | CH625721A5 (enExample) |
| DE (1) | DE2633764C2 (enExample) |
| FR (1) | FR2359871A1 (enExample) |
| GB (1) | GB1531669A (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2852001A1 (de) * | 1978-12-01 | 1980-06-12 | Metallgesellschaft Ag | Verfahren zum ummanteln von rotationssymmetrischen, metallischen formkoerpern |
| JPS55111877A (en) * | 1979-02-20 | 1980-08-28 | Nissan Motor Co Ltd | Preparation of polyurethane coated substrate |
| JPS57184475A (en) * | 1981-05-08 | 1982-11-13 | Ihara Chem Ind Co Ltd | Method of bonding urethane elastomer to metal |
| JPS59152845A (ja) * | 1983-02-18 | 1984-08-31 | セイコ−化成株式会社 | 新規な複合素材 |
| JPS6164441A (ja) * | 1984-09-07 | 1986-04-02 | 新日本製鐵株式会社 | 重防食被覆鋼材 |
| DE3541478A1 (de) * | 1985-11-23 | 1987-05-27 | Beiersdorf Ag | Herzklappenprothese und verfahren zu deren herstellung |
| JP3080979B2 (ja) * | 1990-10-04 | 2000-08-28 | ポリプラスチックス株式会社 | ポリアセタール樹脂製の接着製品 |
| DE4131203A1 (de) * | 1991-09-19 | 1993-03-25 | Bayer Ag | Salzgetriebener pur-folienverbund |
| JP3400298B2 (ja) * | 1997-06-11 | 2003-04-28 | ワイケイケイ株式会社 | 樹脂複合アルミニウム形材、断熱アルミニウム形材、それらの製造方法及びそれに用いる装置 |
| DE19825087B4 (de) * | 1998-06-05 | 2018-12-27 | Basf Se | Verfahren zur Herstellung von Schiffsrümpfen, Laderaumabdeckungen oder Brücken enthaltend Verbundelemente |
| US7338697B2 (en) | 2000-07-24 | 2008-03-04 | High Voltage Graphics, Inc. | Co-molded direct flock and flock transfer and methods of making same |
| US7364782B2 (en) | 2000-07-24 | 2008-04-29 | High Voltage Graphics, Inc. | Flocked transfer and article of manufacture including the application of the transfer by thermoplastic polymer film |
| US6929771B1 (en) | 2000-07-31 | 2005-08-16 | High Voltage Graphics, Inc. | Method of decorating a molded article |
| US8354050B2 (en) | 2000-07-24 | 2013-01-15 | High Voltage Graphics, Inc. | Co-molded direct flock and flock transfer and methods of making same |
| US7344769B1 (en) * | 2000-07-24 | 2008-03-18 | High Voltage Graphics, Inc. | Flocked transfer and article of manufacture including the flocked transfer |
| EP1416471B1 (en) * | 2001-08-06 | 2006-09-13 | Index Corporation | Device and method for judging dog s feeling from cry vocal c haracter analysis |
| WO2003031083A1 (en) | 2001-10-05 | 2003-04-17 | High Voltage Graphics, Inc. | Screen printed resin film applique or transfer made from liquid plastic dispersion |
| CA2489868A1 (en) * | 2002-07-03 | 2004-01-15 | High Voltage Graphics, Inc. | Process for printing and molding a flocked article |
| US20040050482A1 (en) * | 2002-07-03 | 2004-03-18 | Abrams Louis Brown | Flocked articles and methods of making same |
| DE10308582A1 (de) * | 2003-02-27 | 2004-09-30 | Arvinmeritor Gmbh | Verfahren zum Herstellen eines Fahrzeug-Karosserieteils |
| CA2541821A1 (en) * | 2003-10-08 | 2005-04-21 | High Voltage Graphics, Inc. | Processes for precutting laminated flocked articles |
| US7465485B2 (en) | 2003-12-23 | 2008-12-16 | High Voltage Graphics, Inc. | Process for dimensionalizing flocked articles or wear, wash and abrasion resistant flocked articles |
| US7393576B2 (en) | 2004-01-16 | 2008-07-01 | High Voltage Graphics, Inc. | Process for printing and molding a flocked article |
| US8007889B2 (en) | 2005-04-28 | 2011-08-30 | High Voltage Graphics, Inc. | Flocked multi-colored adhesive article with bright lustered flock and methods for making the same |
| WO2007016342A2 (en) | 2005-07-28 | 2007-02-08 | High Voltage Graphics, Inc. | Flocked articles having noncompatible insert and porous film |
| US7749589B2 (en) * | 2005-09-20 | 2010-07-06 | High Voltage Graphics, Inc. | Flocked elastomeric articles |
| US20070148397A1 (en) * | 2005-12-07 | 2007-06-28 | High Voltage Graphics, Inc. | Flocked multi-colored adhesive article with bright lustered flock |
| WO2008101115A1 (en) | 2007-02-14 | 2008-08-21 | High Voltage Graphics, Inc. | Sublimation dye printed textile |
| DE102008040967A1 (de) * | 2008-08-04 | 2010-02-11 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Werkstoff-Kunststoff-Verbunde und Verfahren zu ihrer Herstellung |
| US9193214B2 (en) | 2012-10-12 | 2015-11-24 | High Voltage Graphics, Inc. | Flexible heat sealable decorative articles and method for making the same |
| DE102019217139A1 (de) * | 2019-11-06 | 2021-05-06 | Robert Bosch Gmbh | Gasphasen-Beschichtungsverfahren mit einem mindestens zweifach funktionalisierten Organosilan als Präkursor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2850424A (en) * | 1956-02-01 | 1958-09-02 | Goodyear Tire & Rubber | Adhesive process |
| US3309261A (en) * | 1966-04-21 | 1967-03-14 | American Cyanamid Co | Adhesion of urethane adhesives to metals |
| US3589932A (en) * | 1969-03-13 | 1971-06-29 | Gen Mills Inc | Process of coating metal substrates and resulting coated metal substrates |
| US4004050A (en) * | 1974-08-26 | 1977-01-18 | The Goodyear Tire & Rubber Company | Two-part primer system for FRP bonding |
-
1976
- 1976-07-28 DE DE2633764A patent/DE2633764C2/de not_active Expired
-
1977
- 1977-07-21 US US05/817,880 patent/US4160851A/en not_active Expired - Lifetime
- 1977-07-22 CA CA283,335A patent/CA1094406A/en not_active Expired
- 1977-07-26 GB GB31274/77A patent/GB1531669A/en not_active Expired
- 1977-07-26 CH CH922677A patent/CH625721A5/de not_active IP Right Cessation
- 1977-07-26 AT AT0543177A patent/AT364535B/de not_active IP Right Cessation
- 1977-07-27 JP JP52089379A patent/JPS6026024B2/ja not_active Expired
- 1977-07-28 FR FR7723303A patent/FR2359871A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2359871A1 (fr) | 1978-02-24 |
| JPS5316079A (en) | 1978-02-14 |
| US4160851A (en) | 1979-07-10 |
| JPS6026024B2 (ja) | 1985-06-21 |
| ATA543177A (de) | 1981-03-15 |
| FR2359871B1 (enExample) | 1984-04-27 |
| CH625721A5 (enExample) | 1981-10-15 |
| AT364535B (de) | 1981-10-27 |
| CA1094406A (en) | 1981-01-27 |
| DE2633764B1 (de) | 1978-01-05 |
| GB1531669A (en) | 1978-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Publication of the examined application without previous publication of unexamined application | ||
| C2 | Grant after previous publication (2nd publication) |