CA1093726A - Compositions adhesives et enduit a retardateur de prise - Google Patents

Compositions adhesives et enduit a retardateur de prise

Info

Publication number: CA1093726A
Authority: CA; Canada
Prior art keywords: composition; solvent; curable; organic; initiator
Prior art date: 1975-12-30
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

CA268,680A

Other languages

English (en)

Inventor

Francis R. Martin

Bernard J. Bolger

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.)

Henkel Loctite Ireland Ltd

Original Assignee

Henkel Loctite Ireland Ltd

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.)

1975-12-30

Filing date

1976-12-23

Publication date

1981-01-13

1976-12-23 Application filed by Henkel Loctite Ireland Ltd filed Critical Henkel Loctite Ireland Ltd

1981-01-13 Application granted granted Critical

1981-01-13 Publication of CA1093726A publication Critical patent/CA1093726A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 130
239000000853 adhesive Substances 0.000 title claims abstract description 15
230000001070 adhesive effect Effects 0.000 title claims abstract description 15
238000000576 coating method Methods 0.000 title abstract description 8
239000011248 coating agent Substances 0.000 title description 6
239000002904 solvent Substances 0.000 claims abstract description 46
239000000178 monomer Substances 0.000 claims abstract description 33
239000000126 substance Substances 0.000 claims abstract description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
239000001301 oxygen Substances 0.000 claims abstract description 23
229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
239000003999 initiator Substances 0.000 claims abstract description 21
238000001704 evaporation Methods 0.000 claims abstract description 12
230000008020 evaporation Effects 0.000 claims abstract description 11
239000003960 organic solvent Substances 0.000 claims abstract description 10
230000009477 glass transition Effects 0.000 claims abstract description 9
238000009877 rendering Methods 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 12
229920000058 polyacrylate Polymers 0.000 claims description 10
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
150000002432 hydroperoxides Chemical class 0.000 claims description 9
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
229920000620 organic polymer Polymers 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 6
239000000654 additive Substances 0.000 claims description 5
239000008199 coating composition Substances 0.000 claims description 5
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 4
238000010526 radical polymerization reaction Methods 0.000 claims description 4
230000000996 additive effect Effects 0.000 claims description 3
150000002976 peresters Chemical class 0.000 claims description 3
150000001451 organic peroxides Chemical group 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical group 0.000 claims 2
150000003254 radicals Chemical class 0.000 abstract description 22
230000005540 biological transmission Effects 0.000 abstract 1
230000002708 enhancing effect Effects 0.000 abstract 1
-1 polyethylene Polymers 0.000 description 28
125000004432 carbon atom Chemical group C* 0.000 description 24
125000000217 alkyl group Chemical group 0.000 description 15
239000004615 ingredient Substances 0.000 description 13
239000000463 material Substances 0.000 description 10
150000002430 hydrocarbons Chemical class 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
238000006116 polymerization reaction Methods 0.000 description 7
230000002411 adverse Effects 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
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 6
150000002431 hydrogen Chemical class 0.000 description 6
229940063557 methacrylate Drugs 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229920001228 polyisocyanate Polymers 0.000 description 6
239000005056 polyisocyanate Substances 0.000 description 6
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
125000005442 diisocyanate group Chemical group 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
125000000864 peroxy group Chemical group O(O*)* 0.000 description 4
239000004014 plasticizer Substances 0.000 description 4
150000003335 secondary amines Chemical group 0.000 description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229940106691 bisphenol a Drugs 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
239000004926 polymethyl methacrylate Substances 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
239000000565 sealant Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
150000007945 N-acyl ureas Chemical group 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001252 acrylic acid derivatives Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000010408 film Substances 0.000 description 2
230000008570 general process Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
150000004053 quinones Chemical class 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
229960002317 succinimide Drugs 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
239000010409 thin film Substances 0.000 description 2
239000001993 wax Substances 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
RXUVWJWQFPJWOV-OWOJBTEDSA-N (e)-1,2-diisocyanatoethene Chemical compound O=C=N\C=C\N=C=O RXUVWJWQFPJWOV-OWOJBTEDSA-N 0.000 description 1
OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 1
VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 description 1
IPEBJCNYCFJZHC-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,6-diisocyanatobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(N=C=O)C(N=C=O)=C1Cl IPEBJCNYCFJZHC-UHFFFAOYSA-N 0.000 description 1
IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
ZPOUDMYDJJMHOO-UHFFFAOYSA-N 1-(1-hydroxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(O)CCCCC1 ZPOUDMYDJJMHOO-UHFFFAOYSA-N 0.000 description 1
NMGPHUOPSWFUEB-UHFFFAOYSA-N 2-(butylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCCNCCOC(=O)C(C)=C NMGPHUOPSWFUEB-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
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
SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 description 1
GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-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
BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-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
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
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000518994 Conta Species 0.000 description 1
241000811158 Developea Species 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
229910001209 Low-carbon steel Inorganic materials 0.000 description 1
VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 description 1
QKWFLYJSEPQZQR-UHFFFAOYSA-N N=C=O.N=C=O.CC(C)Cl Chemical compound N=C=O.N=C=O.CC(C)Cl QKWFLYJSEPQZQR-UHFFFAOYSA-N 0.000 description 1
DXCPEDGVEJWXRB-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC(C)=C(C)C=C1C Chemical compound N=C=O.N=C=O.CC1=CC(C)=C(C)C=C1C DXCPEDGVEJWXRB-UHFFFAOYSA-N 0.000 description 1
229930192627 Naphthoquinone Natural products 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001328 Polyvinylidene chloride Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-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
230000001133 acceleration Effects 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
150000001253 acrylic acids Chemical class 0.000 description 1
239000013466 adhesive and sealant Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001555 benzenes Chemical group 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229920006217 cellulose acetate butyrate Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000008021 deposition Effects 0.000 description 1
ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
125000005639 glycero group Chemical group 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
229960002163 hydrogen peroxide Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000005865 ionizing radiation Effects 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008204 material by function Substances 0.000 description 1
230000013011 mating Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000002184 metal Substances 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
229940075566 naphthalene Drugs 0.000 description 1
150000002791 naphthoquinones Chemical class 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
229940117969 neopentyl glycol Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
230000035699 permeability Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
238000004382 potting Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000008569 process Effects 0.000 description 1
BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
150000003152 propanolamines Chemical class 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000013008 thixotropic agent Substances 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
229940086542 triethylamine Drugs 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Adhesives Or Adhesive Processes (AREA)
Paints Or Removers (AREA)

CA268,680A 1975-12-30 1976-12-23 Compositions adhesives et enduit a retardateur de prise Expired CA1093726A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IE282875A IE42764L (en)	1975-12-30	1975-12-30	Curable composition comprising a dissolved polymer
IE2828/75		1975-12-30

Publications (1)

Publication Number	Publication Date
CA1093726A true CA1093726A (fr)	1981-01-13

Family

ID=11036664

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA268,680A Expired CA1093726A (fr)	1975-12-30	1976-12-23	Compositions adhesives et enduit a retardateur de prise

Country Status (8)

Country	Link
JP (1)	JPS5298047A (fr)
AU (1)	AU517529B2 (fr)
CA (1)	CA1093726A (fr)
DE (1)	DE2659663A1 (fr)
FR (1)	FR2337187A1 (fr)
GB (1)	GB1561180A (fr)
IE (1)	IE42764L (fr)
IT (1)	IT1069262B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3923023A1 (de) *	1989-07-12	1991-01-24	Siemens Ag	Uv-haertbarer klebstoff fuer ein halbleiterchipmontageverfahren
JPH03111469A (ja) *	1989-09-27	1991-05-13	Toray Ind Inc	接着剤組成物
JP3864605B2 (ja) *	1998-02-27	2007-01-10	藤倉化成株式会社	紫外線硬化性被覆用樹脂組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3832274A (en) *	1973-06-06	1974-08-27	Lord Corp	Fast curing adhesives
DE2531180C2 (de) *	1975-07-11	1982-04-01	Institut chimi&ccaron;eskoj fiziki Akademii Nauk SSSR, Moskva	Anaerobe Mischung

1975
- 1975-12-30 IE IE282875A patent/IE42764L/xx unknown
1976
- 1976-12-23 CA CA268,680A patent/CA1093726A/fr not_active Expired
- 1976-12-30 JP JP16082276A patent/JPS5298047A/ja active Pending
- 1976-12-30 IT IT5284276A patent/IT1069262B/it active
- 1976-12-30 GB GB5430476A patent/GB1561180A/en not_active Expired
- 1976-12-30 FR FR7639597A patent/FR2337187A1/fr active Granted
- 1976-12-30 DE DE19762659663 patent/DE2659663A1/de not_active Withdrawn
- 1976-12-31 AU AU20984/76A patent/AU517529B2/en not_active Expired

Also Published As

Publication number	Publication date
DE2659663A1 (de)	1977-09-01
AU517529B2 (en)	1981-08-06
JPS5298047A (en)	1977-08-17
FR2337187A1 (fr)	1977-07-29
IE42764L (en)	1977-06-30
IT1069262B (it)	1985-03-25
AU2098476A (en)	1978-07-06
FR2337187B1 (fr)	1981-05-29
GB1561180A (en)	1980-02-13

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
CA1109596A (fr)	1981-09-22	Accelerateurs pour substances durcissables a base d'ester d'acrylate
CA1062846A (fr)	1979-09-18	Accelerateur de type derive de l'hydrazine utilise dans les adhesifs de type acrylate et les produits de scellement
US4321349A (en)	1982-03-23	Accelerator for curable compositions
US4309334A (en)	1982-01-05	Thermally-resistant glass-filled adhesive/sealant compositions
US4118442A (en)	1978-10-03	Anaerobic pressure sensitive adhesive composition
US4574142A (en)	1986-03-04	Curable adhesive composition toughened with styrene-butadiene block copolymer rubbers
US3970505A (en)	1976-07-20	Anaerobic compositions and surface activator therefor
US4039705A (en)	1977-08-02	Anaerobic pressure sensitive adhesive stocks
US3435012A (en)	1969-03-25	Anaerobic sealant composition containing monoacrylate esters
US4322509A (en)	1982-03-30	Fast curing phosphate modified anaerobic adhesive compositions
US4574138A (en)	1986-03-04	Rapid cure acrylic monomer systems containing elemental aluminum metal
CA1102948A (fr)	1981-06-09	Colle bi-element a prise rapide
JPH0233049B2 (fr)	1990-07-25
US4404345A (en)	1983-09-13	Novel adhesive compositions
JPS63142001A (ja)	1988-06-14	構造接着剤組成物
CA1283992C (fr)	1991-05-07	Compositions adhesives
US4043982A (en)	1977-08-23	Peroxide initiated polymerizable acrylate-isocyanate monomer compositions
US3634379A (en)	1972-01-11	Acrylic anaerobic compositions containing a hydroperoxide and a dialkylperoxide
US5385958A (en)	1995-01-31	Activator formulation and composition utilizing same
WO2022223737A1 (fr)	2022-10-27	Compositions durcissables par voie anaérobie
CA1183629A (fr)	1985-03-05	Composition adhesive renforcee a l'aide de polyisoprene
US4007323A (en)	1977-02-08	Initiator for anaerobic compositions
US4413108A (en)	1983-11-01	Anaerobically-curing compositions
US4442267A (en)	1984-04-10	Heat resistant toughened adhesive composition
CA1093726A (fr)	1981-01-13	Compositions adhesives et enduit a retardateur de prise