CA1053440A - Methode de collage avec un adhesif a cure anaerobique - Google Patents

Methode de collage avec un adhesif a cure anaerobique

Info

Publication number: CA1053440A
Authority: CA; Canada
Prior art keywords: denotes; carbon atoms; shaped article; group; adhesive
Prior art date: 1973-04-14
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

CA195,352A

Other languages

English (en)

Other versions

CA195352S (en

Inventor

Bernard P. Stark

George E. Green

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.)

Novartis AG

Original Assignee

Ciba Geigy 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.)

1973-04-14

Filing date

1974-03-19

Publication date

1979-05-01

1973-04-14 Priority claimed from GB1811073A external-priority patent/GB1419800A/en

1974-03-19 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-05-01 Application granted granted Critical

1979-05-01 Publication of CA1053440A publication Critical patent/CA1053440A/fr

Status Expired legal-status Critical Current

Links

239000000853 adhesive Substances 0.000 title claims abstract description 43
230000001070 adhesive effect Effects 0.000 title claims abstract description 43
238000000034 method Methods 0.000 title claims abstract description 34
239000004576 sand Substances 0.000 claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
150000002148 esters Chemical class 0.000 claims abstract description 16
238000010438 heat treatment Methods 0.000 claims abstract description 14
239000011236 particulate material Substances 0.000 claims abstract description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
150000002978 peroxides Chemical class 0.000 claims abstract description 9
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
239000002245 particle Substances 0.000 claims abstract description 8
239000011261 inert gas Substances 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
238000000465 moulding Methods 0.000 claims abstract description 4
230000000977 initiatory effect Effects 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 42
-1 cycloaliphatic Chemical group 0.000 claims description 17
125000001931 aliphatic group Chemical group 0.000 claims description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
239000007789 gas Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
239000011248 coating agent Substances 0.000 claims description 7
238000000576 coating method Methods 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
239000001273 butane Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 5
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 4
150000002430 hydrocarbons Chemical group 0.000 claims description 4
229920003986 novolac Polymers 0.000 claims description 4
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 3
229920001568 phenolic resin Polymers 0.000 claims description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
YKJCDLPCROVLAM-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propoxy]butoxy]propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COCCCCOCC(O)COC(=O)C(C)=C YKJCDLPCROVLAM-UHFFFAOYSA-N 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
238000007789 sealing Methods 0.000 claims description 2
239000002685 polymerization catalyst Substances 0.000 claims 6
LUUIUSRHDNYICK-UHFFFAOYSA-N (2-hydroxy-3-propanoyloxypropyl) 2-methylprop-2-enoate Chemical compound CCC(=O)OCC(O)COC(=O)C(C)=C LUUIUSRHDNYICK-UHFFFAOYSA-N 0.000 claims 1
DQOKNNHAZSNFOC-UHFFFAOYSA-N (3-butoxy-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CCCCOCC(O)COC(=O)C(C)=C DQOKNNHAZSNFOC-UHFFFAOYSA-N 0.000 claims 1
JMWGZSWSTCGVLX-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO JMWGZSWSTCGVLX-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
PARFJNFTUWJVEF-UHFFFAOYSA-N bis[2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl] hexanedioate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)CCCCC(=O)OCC(O)COC(=O)C(C)=C PARFJNFTUWJVEF-UHFFFAOYSA-N 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
239000011343 solid material Substances 0.000 claims 1
230000006835 compression Effects 0.000 abstract description 6
238000007906 compression Methods 0.000 abstract description 6
239000003054 catalyst Substances 0.000 abstract description 3
239000000178 monomer Substances 0.000 abstract description 3
239000007787 solid Substances 0.000 abstract description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 9
IPHOGHLMDSHXJU-UHFFFAOYSA-N CC(C)C1=CC=CC=C1.NCCNCCNCCN.OO Chemical compound CC(C)C1=CC=CC=C1.NCCNCCNCCN.OO IPHOGHLMDSHXJU-UHFFFAOYSA-N 0.000 description 8
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 7
150000002118 epoxides Chemical class 0.000 description 7
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000002432 hydroperoxides Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
QYDKJTBNIBMBLZ-UHFFFAOYSA-N N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine 2-methylprop-2-enoic acid Chemical compound C(C(=C)C)(=O)O.NCCNCCNCCN QYDKJTBNIBMBLZ-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000010992 reflux Methods 0.000 description 2
IEQSQFMTSRBHSH-UHFFFAOYSA-N (3-hydroxy-2-propanoyloxypropyl) 2-methylprop-2-enoate Chemical compound CCC(=O)OC(CO)COC(=O)C(C)=C IEQSQFMTSRBHSH-UHFFFAOYSA-N 0.000 description 1
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
102100038916 Caspase-5 Human genes 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241001091551 Clio Species 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
VMWXFJWXHSAJIU-UHFFFAOYSA-N [3-[4-[2,3-bis(2-methylprop-2-enoyloxy)propoxy]butoxy]-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(OC(=O)C(C)=C)COCCCCOCC(OC(=O)C(C)=C)COC(=O)C(C)=C VMWXFJWXHSAJIU-UHFFFAOYSA-N 0.000 description 1
150000001253 acrylic acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
150000004705 aldimines Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
238000007664 blowing Methods 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
CABJOLBHWJIZSS-UHFFFAOYSA-N butan-2-one;hydrogen peroxide Chemical compound OO.CCC(C)=O CABJOLBHWJIZSS-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000012669 compression test Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000007599 discharging Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
KCWDJXPPZHMEIK-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1 KCWDJXPPZHMEIK-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
150000002976 peresters Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000005086 pumping Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011819 refractory material Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
235000002020 sage Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000005029 sieve analysis Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
150000003585 thioureas Chemical class 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
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1

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Adhesives Or Adhesive Processes (AREA)

CA195,352A 1973-04-14 1974-03-19 Methode de collage avec un adhesif a cure anaerobique Expired CA1053440A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1811073A GB1419800A (en)	1973-04-14	1973-04-14	Making shaped articles from particulate material and an anaerobic adhesive

Publications (1)

Publication Number	Publication Date
CA1053440A true CA1053440A (fr)	1979-05-01

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ID=10106829

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Application Number	Title	Priority Date	Filing Date
CA195,352A Expired CA1053440A (fr)	1973-04-14	1974-03-19	Methode de collage avec un adhesif a cure anaerobique

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CA (1)	CA1053440A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526219A (en) *	1980-01-07	1985-07-02	Ashland Oil, Inc.	Process of forming foundry cores and molds utilizing binder curable by free radical polymerization

1974
- 1974-03-19 CA CA195,352A patent/CA1053440A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526219A (en) *	1980-01-07	1985-07-02	Ashland Oil, Inc.	Process of forming foundry cores and molds utilizing binder curable by free radical polymerization

Publication	Publication Date	Title
US4921921A (en)	1990-05-01	Meltable aerobically cured plastic compositions
US4526219A (en)	1985-07-02	Process of forming foundry cores and molds utilizing binder curable by free radical polymerization
US4836878A (en)	1989-06-06	Method of adhering two surfaces with an anaerobically polymerizable acrylic ester composition
CA1191996A (fr)	1985-08-13	Compositions d'epoxy et d'acrylate thermodurcissables
US3986546A (en)	1976-10-19	Method of making a foundry mold or core with an anaerobically cured adhesive
US4444806A (en)	1984-04-24	Process for forming an epoxy-acrylate coating
JPS61180762A (ja)	1986-08-13	（アシルチオプロピル）ポリフェノールを含有する組成物
CN102549059A (zh)	2012-07-04	厌氧固化组合物
CA1068063A (fr)	1979-12-18	Methode de collage par adhesifs anaerobies
CA1128234A (fr)	1982-07-20	Colles
CA1053440A (fr)	1979-05-01	Methode de collage avec un adhesif a cure anaerobique
US4287106A (en)	1981-09-01	Adhesive or adhesive component containing chlorosulfonated amide or imide
HK128694A (en)	1994-11-25	Radical polymerizable compositions and their use
US5096963A (en)	1992-03-17	Stabilized polymerizable compositions
JPH07252334A (ja)	1995-10-03	液体の樹脂形成組成物及び２パッケージ系並びにそれにより透過性基材をシールする方法
CN117377706A (zh)	2024-01-09	两部分可固化组合物
JPS6111701B2 (fr)	1986-04-04
JPS5935707B2 (ja)	1984-08-30	微粒子状固体物質から成形物品を成形する方法
US5373075A (en)	1994-12-13	Anaerobic compositions which expand when post-cured
JPS6156265B2 (fr)	1986-12-01
HK138095A (en)	1995-09-08	Radical polymerizable compositions and their use
JP4627258B2 (ja)	2011-02-09	接着性組成物、接着剤、接着方法及び家具
US4631325A (en)	1986-12-23	Accelerator combinations for anaerobic polymerization
JPS6156264B2 (fr)	1986-12-01
JPH0372625B2 (fr)	1991-11-19

CA1053440A - Methode de collage avec un adhesif a cure anaerobique - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=10106829

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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