CA1107751A - Monomeres et calles anaerobiques - Google Patents

Monomeres et calles anaerobiques

Info

Publication number: CA1107751A
Authority: CA; Canada
Prior art keywords: group; carbon atoms; member selected; methyl; monomer
Prior art date: 1976-01-07
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

CA350,503A

Other languages

English (en)

Inventor

Gerhardt P. Werber

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.)

Estech Specialty Chemicals Corp

Original Assignee

Estech Specialty Chemicals Corp

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.)

1976-01-07

Filing date

1980-04-23

Publication date

1981-08-25

1976-01-07 Priority claimed from US05/647,217 external-priority patent/US4209604A/en

1980-04-23 Application filed by Estech Specialty Chemicals Corp filed Critical Estech Specialty Chemicals Corp

1980-04-23 Priority to CA350,503A priority Critical patent/CA1107751A/fr

1981-08-25 Application granted granted Critical

1981-08-25 Publication of CA1107751A publication Critical patent/CA1107751A/fr

Status Expired legal-status Critical Current

Links

239000000178 monomer Substances 0.000 title claims abstract description 105
239000000853 adhesive Substances 0.000 title abstract description 53
230000001070 adhesive effect Effects 0.000 title abstract description 53
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 40
-1 ethyl radicals Chemical class 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
150000003254 radicals Chemical class 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000000547 substituted alkyl group Chemical group 0.000 claims description 9
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 8
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 4
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
150000002432 hydroperoxides Chemical class 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
150000003949 imides Chemical class 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 11
239000002253 acid Substances 0.000 description 11
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 10
239000000376 reactant Substances 0.000 description 10
150000008064 anhydrides Chemical class 0.000 description 9
238000005273 aeration Methods 0.000 description 8
238000006116 polymerization reaction Methods 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
150000008065 acid anhydrides Chemical class 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
150000002118 epoxides Chemical class 0.000 description 6
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
238000005259 measurement Methods 0.000 description 5
229920005862 polyol Polymers 0.000 description 5
150000003077 polyols Chemical class 0.000 description 5
230000000087 stabilizing effect Effects 0.000 description 5
229910000975 Carbon steel Inorganic materials 0.000 description 4
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
238000012644 addition polymerization Methods 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
125000004386 diacrylate group Chemical group 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000013011 mating Effects 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
229940070721 polyacrylate Drugs 0.000 description 4
229920000058 polyacrylate Polymers 0.000 description 4
229920000647 polyepoxide Polymers 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
238000005698 Diels-Alder reaction Methods 0.000 description 3
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
125000004171 alkoxy aryl group Chemical group 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
239000007795 chemical reaction product Substances 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
229940116336 glycol dimethacrylate Drugs 0.000 description 3
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 description 2
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
229930185605 Bisphenol Natural products 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
229910014033 C-OH Inorganic materials 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
229940091173 hydantoin Drugs 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
229940102838 methylmethacrylate Drugs 0.000 description 2
125000005429 oxyalkyl group Chemical group 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
239000004926 polymethyl methacrylate Substances 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000012970 tertiary amine catalyst Substances 0.000 description 2
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
APXNRLPBXNJAGG-UHFFFAOYSA-N 1,2:3,4-diepoxycyclohexane Chemical compound C1CC2OC2C2OC12 APXNRLPBXNJAGG-UHFFFAOYSA-N 0.000 description 1
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
JFZBUNLOTDDXNY-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)OCC(C)OC(=O)C(C)=C JFZBUNLOTDDXNY-UHFFFAOYSA-N 0.000 description 1
HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
RIYDSTPQZDWTBD-UHFFFAOYSA-N 2-[2-[2-[2-(2-chloroprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-chloroprop-2-enoate Chemical compound ClC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(Cl)=C RIYDSTPQZDWTBD-UHFFFAOYSA-N 0.000 description 1
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 description 1
QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 description 1
TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 description 1
WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-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
KJWJZGGRAAABBZ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;oxolane-2-carbaldehyde Chemical compound CC(=C)C(O)=O.O=CC1CCCO1 KJWJZGGRAAABBZ-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
GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 1
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 1
SNCMCDMEYCLVBO-UHFFFAOYSA-N 3-aminopropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN SNCMCDMEYCLVBO-UHFFFAOYSA-N 0.000 description 1
OTKLRHWBZHQJOP-UHFFFAOYSA-N 3-aminopropyl prop-2-enoate Chemical compound NCCCOC(=O)C=C OTKLRHWBZHQJOP-UHFFFAOYSA-N 0.000 description 1
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-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
XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
OKGSJRHYRDICBC-UHFFFAOYSA-N N-methylethenamine 2-methylprop-2-enoic acid Chemical compound C(C(=C)C)(=O)O.CNC=C OKGSJRHYRDICBC-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
SIWFRAYSJGYECR-UHFFFAOYSA-N cyclopentadiene dioxide Chemical compound C1C2OC2C2OC12 SIWFRAYSJGYECR-UHFFFAOYSA-N 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 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
230000001747 exhibiting effect Effects 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000011521 glass Substances 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229940063557 methacrylate Drugs 0.000 description 1
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
230000036647 reaction Effects 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
235000019204 saccharin Nutrition 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
239000012207 thread-locking agent Substances 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Adhesives Or Adhesive Processes (AREA)

CA350,503A 1976-01-07 1980-04-23 Monomeres et calles anaerobiques Expired CA1107751A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA350,503A CA1107751A (fr)	1976-01-07	1980-04-23	Monomeres et calles anaerobiques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/647,217 US4209604A (en)	1976-01-07	1976-01-07	Anaerobic monomers and adhesives
US647,217		1976-01-07
CA263,442A CA1083597A (fr)	1976-01-07	1976-10-15	Monomeres et adhesifs anaerobies
CA350,503A CA1107751A (fr)	1976-01-07	1980-04-23	Monomeres et calles anaerobiques

Publications (1)

Publication Number	Publication Date
CA1107751A true CA1107751A (fr)	1981-08-25

Family

ID=27164692

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA350,503A Expired CA1107751A (fr)	1976-01-07	1980-04-23	Monomeres et calles anaerobiques

Country Status (1)

Country	Link
CA (1)	CA1107751A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5876210A (en)	1994-04-22	1999-03-02	Dentsply G.M.B.H.	Dental polymer product
US5998499A (en)	1994-03-25	1999-12-07	Dentsply G.M.B.H.	Liquid crystalline (meth)acrylate compounds, composition and method
US6353061B1 (en)	1993-05-26	2002-03-05	Dentsply Gmbh	α, ω-methacrylate terminated macromonomer compounds
US6369164B1 (en)	1993-05-26	2002-04-09	Dentsply G.M.B.H.	Polymerizable compounds and compositions

1980
- 1980-04-23 CA CA350,503A patent/CA1107751A/fr not_active Expired

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6339114B1 (en)	1993-05-26	2002-01-15	Dentsply Detrey Gmbh	Liquid crystalline (meth)acrylate compounds, composition and method
US6353061B1 (en)	1993-05-26	2002-03-05	Dentsply Gmbh	α, ω-methacrylate terminated macromonomer compounds
US6369164B1 (en)	1993-05-26	2002-04-09	Dentsply G.M.B.H.	Polymerizable compounds and compositions
US5998499A (en)	1994-03-25	1999-12-07	Dentsply G.M.B.H.	Liquid crystalline (meth)acrylate compounds, composition and method
US5876210A (en)	1994-04-22	1999-03-02	Dentsply G.M.B.H.	Dental polymer product

Legal Events

Date	Code	Title	Description
1998-08-25	MKEX	Expiry

Publication	Publication Date	Title
CA1083597A (fr)	1980-08-12	Monomeres et adhesifs anaerobies
US4431787A (en)	1984-02-14	Anaerobic adhesives
KR930008924B1 (ko)	1993-09-17	(n-치환된 카바모일옥시)알카노일옥시알킬 아크릴레이트 중합체 및 이로부터 제조된 조성물
EP0233651B1 (fr)	1991-08-28	Polymères et compositions réticulées faites de ces polymères
US4049750A (en)	1977-09-20	One component shelf stable low shrinkage structural adhesive systems
US4548992A (en)	1985-10-22	Two-part type adhesives
CA1107751A (fr)	1981-08-25	Monomeres et calles anaerobiques
US4569977A (en)	1986-02-11	Anaerobic adhesives
US4302570A (en)	1981-11-24	Reactive plasticizer for anaerobic adhesives
GB1563412A (en)	1980-03-26	Anaerobic curing compositions
US4530988A (en)	1985-07-23	Anaerobic adhesives
EP0517167A2 (fr)	1992-12-09	Polyétheramines souples utilisés dans des compositions de résines époxyde
CA1223999A (fr)	1987-07-07	Adhesifs anaerobies
US3864358A (en)	1975-02-04	Epoxy-acrylic acid esters
US4463150A (en)	1984-07-31	Acrylic or methacrylic terminated oligomers
EP0065735B1 (fr)	1986-09-24	Résines thermodurcissables stabilisées à l'aide d'acide oxalique et de phénothiazine
US4336359A (en)	1982-06-22	Nitric acid stabilized thermosettable resins
US5861466A (en)	1999-01-19	Synergistic improvement in vinyl ester resin shelf life
US5292841A (en)	1994-03-08	Laminating resins having low organic emissions
JPS58147425A (ja)	1983-09-02	カルボキシル基含有反応性ポリマ−、その製法及び粉体塗料バインダ−成分としての使用
JPH0730146B2 (ja)	1995-04-05	重合性組成物
US3660526A (en)	1972-05-02	Adhesive composition containing a vinyl ester resin and an acrylic ester of tetrahydrofurfuryl alcohol or dihydrodicyclopentadienol
EP0296141A2 (fr)	1988-12-21	Revêtement activé par un composé allyloxy
US5298631A (en)	1994-03-29	Spiroorthocarbonate compound and copolymers obtained therefrom
EP0072114B1 (fr)	1984-11-07	Compositions de polyester insaturé durcissable