CA1094406A - Process for the production of plastics/metal composites - Google Patents

Process for the production of plastics/metal composites

Info

Publication number: CA1094406A
Authority: CA; Canada
Prior art keywords: och3; lea; polyurethane dispersion; polyurethane; aqueous polyurethane
Prior art date: 1976-07-28
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

Application number

CA283,335A

Other languages

English (en)

French (fr)

Inventor

Hans-Jurgen Lienert

Helmut Kleimann

Dieter Dieterich

Wulf Von Bonin

Klaus Friederich

Peter Markusch

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1976-07-28

Filing date

1977-07-22

Publication date

1981-01-27

1977-07-22 Application filed by Bayer AG filed Critical Bayer AG

1981-01-27 Application granted granted Critical

1981-01-27 Publication of CA1094406A publication Critical patent/CA1094406A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 48
230000008569 process Effects 0.000 title claims abstract description 32
229920003023 plastic Polymers 0.000 title claims abstract description 25
239000004033 plastic Substances 0.000 title claims abstract description 25
238000004519 manufacturing process Methods 0.000 title abstract description 18
239000002905 metal composite material Substances 0.000 title abstract description 4
239000002184 metal Substances 0.000 claims abstract description 68
229910052751 metal Inorganic materials 0.000 claims abstract description 68
239000005056 polyisocyanate Substances 0.000 claims abstract description 31
229920001228 polyisocyanate Polymers 0.000 claims abstract description 28
150000002739 metals Chemical class 0.000 claims abstract description 17
239000011541 reaction mixture Substances 0.000 claims abstract description 17
239000002318 adhesion promoter Substances 0.000 claims abstract description 9
239000002131 composite material Substances 0.000 claims abstract description 9
229920003009 polyurethane dispersion Polymers 0.000 claims description 48
-1 alkoxy silane Chemical compound 0.000 claims description 41
239000006185 dispersion Substances 0.000 claims description 23
229910000077 silane Inorganic materials 0.000 claims description 15
125000000129 anionic group Chemical group 0.000 claims description 11
125000002091 cationic group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229920005830 Polyurethane Foam Polymers 0.000 claims description 5
239000011496 polyurethane foam Substances 0.000 claims description 5
230000006872 improvement Effects 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
238000001035 drying Methods 0.000 claims description 2
NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 2
LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
239000011888 foil Substances 0.000 abstract description 19
238000006243 chemical reaction Methods 0.000 abstract description 12
239000004814 polyurethane Substances 0.000 description 41
229920002635 polyurethane Polymers 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 24
239000006260 foam Substances 0.000 description 23
229910052782 aluminium Inorganic materials 0.000 description 22
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 22
238000000465 moulding Methods 0.000 description 19
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
150000001875 compounds Chemical class 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
238000000926 separation method Methods 0.000 description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
229920000570 polyether Polymers 0.000 description 10
239000002253 acid Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
229920000728 polyester Polymers 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
239000000126 substance 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
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
238000000576 coating method Methods 0.000 description 6
229920006264 polyurethane film Polymers 0.000 description 6
150000004756 silanes Chemical class 0.000 description 6
239000004721 Polyphenylene oxide Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000000654 additive Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000011248 coating agent Substances 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
238000005187 foaming Methods 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229910000831 Steel Inorganic materials 0.000 description 4
239000001361 adipic acid Substances 0.000 description 4
235000011037 adipic acid Nutrition 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
230000001413 cellular effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000004872 foam stabilizing agent Substances 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 4
239000013518 molded foam Substances 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
229920006295 polythiol Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
230000003014 reinforcing effect Effects 0.000 description 4
239000010959 steel Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
239000004604 Blowing Agent Substances 0.000 description 3
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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
229920002396 Polyurea Polymers 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
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000011049 filling Methods 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
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000006082 mold release agent Substances 0.000 description 3
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
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
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
244000089486 Phragmites australis subsp australis Species 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
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 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
230000003385 bacteriostatic effect Effects 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
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 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
239000000975 dye Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
230000001408 fungistatic effect Effects 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
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 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
239000004417 polycarbonate Substances 0.000 description 2
229920000515 polycarbonate Polymers 0.000 description 2
229920006149 polyester-amide block copolymer Polymers 0.000 description 2
229920000582 polyisocyanurate Polymers 0.000 description 2
239000011495 polyisocyanurate Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920006324 polyoxymethylene Polymers 0.000 description 2
229920006389 polyphenyl polymer Polymers 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
150000003839 salts Chemical class 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
239000003381 stabilizer Substances 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 group [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
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
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 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
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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
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
KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-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
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
229940035437 1,3-propanediol Drugs 0.000 description 1
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Classifications

- 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)
Manufacture Of Macromolecular Shaped Articles (AREA)
Moulds For Moulding Plastics Or The Like (AREA)
Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Molding Of Porous Articles (AREA)

CA283,335A 1976-07-28 1977-07-22 Process for the production of plastics/metal composites Expired CA1094406A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2633764.4		1976-07-28
DE2633764A DE2633764C2 (de)	1976-07-28	1976-07-28	Verfahren zur Herstellung von Kunststoff -Metall-Verbunden

Publications (1)

Publication Number	Publication Date
CA1094406A true CA1094406A (en)	1981-01-27

Family

ID=5984065

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA283,335A Expired CA1094406A (en)	1976-07-28	1977-07-22	Process for the production of plastics/metal composites

Country Status (8)

Country	Link
US (1)	US4160851A (2)
JP (1)	JPS6026024B2 (2)
AT (1)	AT364535B (2)
CA (1)	CA1094406A (2)
CH (1)	CH625721A5 (2)
DE (1)	DE2633764C2 (2)
FR (1)	FR2359871A1 (2)
GB (1)	GB1531669A (2)

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* Cited by examiner, † Cited by third party
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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
US7344769B1 (en)	2000-07-24	2008-03-18	High Voltage Graphics, Inc.	Flocked transfer and article of manufacture including the flocked transfer
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
US8354050B2 (en)	2000-07-24	2013-01-15	High Voltage Graphics, Inc.	Co-molded direct flock and flock transfer and methods of making same
US6929771B1 (en)	2000-07-31	2005-08-16	High Voltage Graphics, Inc.	Method of decorating a molded article
US20050081985A1 (en) *	2003-10-08	2005-04-21	Abrams Louis B.	Processes for precutting laminated flocked articles
KR20040014431A (ko) *	2001-08-06	2004-02-14	가부시키가이샤 인덱스	명성의 음성적 특징분석에 기초하는 개의 감정판별장치 및방법
WO2003031083A1 (en)	2001-10-05	2003-04-17	High Voltage Graphics, Inc.	Screen printed resin film applique or transfer made from liquid plastic dispersion
JP2005532202A (ja) *	2002-07-03	2005-10-27	ハイボルテイジグラフィックスインコーポレイテッド	フロック加工品およびその製造方法
AU2003251790A1 (en) *	2002-07-03	2004-01-23	High Voltage Graphics, Inc.	Process for printing and molding a flocked article
DE10308582A1 (de) *	2003-02-27	2004-09-30	Arvinmeritor Gmbh	Verfahren zum Herstellen eines Fahrzeug-Karosserieteils
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
WO2006116706A2 (en)	2005-04-28	2006-11-02	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
JP2016502470A (ja)	2012-10-12	2016-01-28	ハイボルテイジグラフィックスインコーポレイテッドＨｉｇｈＶｏｌｔａｇｅＧｒａｐｈｉｃｓ，Ｉｎｃ．	熱融着可能な可撓性の装飾品およびそれを製造する方法
DE102019217139A1 (de) *	2019-11-06	2021-05-06	Robert Bosch Gmbh	Gasphasen-Beschichtungsverfahren mit einem mindestens zweifach funktionalisierten Organosilan als Präkursor

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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 AT AT0543177A patent/AT364535B/de not_active IP Right Cessation
- 1977-07-26 CH CH922677A patent/CH625721A5/de not_active IP Right Cessation
- 1977-07-26 GB GB31274/77A patent/GB1531669A/en not_active Expired
- 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
US4160851A (en)	1979-07-10
CH625721A5 (2)	1981-10-15
DE2633764C2 (de)	1978-09-07
GB1531669A (en)	1978-11-08
JPS6026024B2 (ja)	1985-06-21
JPS5316079A (en)	1978-02-14
DE2633764B1 (de)	1978-01-05
AT364535B (de)	1981-10-27
ATA543177A (de)	1981-03-15
FR2359871A1 (fr)	1978-02-24
FR2359871B1 (2)	1984-04-27

Legal Events

Date	Code	Title	Description
1998-01-27	MKEX	Expiry

Publication	Publication Date	Title
CA1094406A (en)	1981-01-27	Process for the production of plastics/metal composites
US4447486A (en)	1984-05-08	Surface-sealed moldings of cellular polyurethane elastomers and a process for their production
US3016365A (en)	1962-01-09	Polythioetherurethane casting and method of preparing same
US4098731A (en)	1978-07-04	Process for the production of foams
CA1078984A (en)	1980-06-03	Process for the production of inorganicorganic plastic composites
US4058492A (en)	1977-11-15	Process for molding polyurethane foams
US4350777A (en)	1982-09-21	Impermeable molded articles of cellular polyurethane elastomers produced with organofunctional polysiloxane-derivatives and their use as spring elements
US4246363A (en)	1981-01-20	Reaction injection molded polyurethanes having particular flexural modulus factors and at least two thermal transition temperatures in a particular range
US4331778A (en)	1982-05-25	Process for the production of polyurethane plastics
US20040214908A1 (en)	2004-10-28	Phthalate polyester polyl-based and high dimensionally stable all water-blown spray polyurethane foam derived therefrom
JPH09104781A (ja)	1997-04-22	イソシアナートを基礎とする硬質発泡体の製造方法
US4207128A (en)	1980-06-10	Reactive polyurethane coatings
US4046742A (en)	1977-09-06	Compositions containing hydroxyl groups and their use for the production of flameproof plastics
CA1173194A (en)	1984-08-21	Process for the production of polyurethanes using cyclic n-hydroxyalkyl-substituted compounds containing amidine groups as catalysts
US4225678A (en)	1980-09-30	Foamed polyurethane materials with a bitumen and a hydroxy fatty oil
US3505250A (en)	1970-04-07	Polyurethane plastics
US5013766A (en)	1991-05-07	Closed cell, rigid polyurethane foam
CA1206663A (en)	1986-06-24	Process for the production of combinations of organic polyisocyanates and at least partly blocked polyamines
US20060175575A1 (en)	2006-08-10	Method for preparing phthalate polyester polyol-based dimensionally stable spray polyurethane foam
US5488072A (en)	1996-01-30	Rigid closed cell polyisocyanate based foams for use as positive flotation materials in watercraft
US4801623A (en)	1989-01-31	Process for the production of a thixotropic agent, especially for storable reactive polyurethane systems
GB1587046A (en)	1981-03-25	Process for the production of filler-reinforced polyurethane elastomers
US4254229A (en)	1981-03-03	Polyurethane plastics containing thio groups
US4101468A (en)	1978-07-18	Process for cold-hardening polyurethane foams using sulfonamide emulsifiers
US10507621B2 (en)	2019-12-17	Polyurethane compound for producing an integrated insulation component