CA1154455A - (n-substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters - Google Patents

(n-substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters

Info

Publication number: CA1154455A
Authority: CA; Canada
Prior art keywords: compound; photoinitiator; carbon atoms; composition; formula
Prior art date: 1980-03-21
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

CA000370814A

Other languages

English (en)

French (fr)

Inventor

Robert J. Knopf

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.)

Union Carbide Corp

Original Assignee

Union Carbide 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.)

1980-03-21

Filing date

1981-02-13

Publication date

1983-09-27

1981-02-13 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1983-09-27 Application granted granted Critical

1983-09-27 Publication of CA1154455A publication Critical patent/CA1154455A/en

Status Expired legal-status Critical Current

Links

-1 carbamoyloxy Chemical class 0.000 title claims abstract description 31
150000001252 acrylic acid derivatives Chemical class 0.000 title description 2
125000005041 acyloxyalkyl group Chemical group 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 31
150000001875 compounds Chemical class 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 5
125000002993 cycloalkylene group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
HKKDKUMUWRTAIA-UHFFFAOYSA-N nitridooxidocarbon(.) Chemical compound [O]C#N HKKDKUMUWRTAIA-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000000178 monomer Substances 0.000 abstract description 16
150000002596 lactones Chemical class 0.000 abstract description 10
239000012948 isocyanate Substances 0.000 abstract description 8
230000005855 radiation Effects 0.000 abstract description 8
150000002513 isocyanates Chemical class 0.000 abstract description 6
239000000853 adhesive Substances 0.000 abstract description 3
230000001070 adhesive effect Effects 0.000 abstract description 3
239000000976 ink Substances 0.000 abstract description 3
239000003973 paint Substances 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 20
239000003054 catalyst Substances 0.000 description 11
235000013350 formula milk Nutrition 0.000 description 11
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 6
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 6
239000000306 component Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
239000012975 dibutyltin dilaurate Substances 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 5
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
238000000576 coating method Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
GONFBOIJNUKKST-UHFFFAOYSA-N 5-ethylsulfanyl-2h-tetrazole Chemical compound CCSC=1N=NNN=1 GONFBOIJNUKKST-UHFFFAOYSA-N 0.000 description 3
239000005058 Isophorone diisocyanate Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000012190 activator Substances 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
229910052919 magnesium silicate Inorganic materials 0.000 description 3
235000019792 magnesium silicate Nutrition 0.000 description 3
239000000391 magnesium silicate Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229920001610 polycaprolactone Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
QCQXVTVJGLHITJ-UHFFFAOYSA-N 2-(methylcarbamoyloxy)ethyl prop-2-enoate Chemical compound CNC(=O)OCCOC(=O)C=C QCQXVTVJGLHITJ-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001261 isocyanato group Chemical group *N=C=O 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
239000003504 photosensitizing agent Substances 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
230000002035 prolonged effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000036647 reaction Effects 0.000 description 2
239000007787 solid Substances 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
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
YLPSXUVZWFTCEJ-UHFFFAOYSA-N (1-hydroxycyclooctyl) prop-2-enoate Chemical compound C=CC(=O)OC1(O)CCCCCCC1 YLPSXUVZWFTCEJ-UHFFFAOYSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
FYWJWWMKCARWQG-UHFFFAOYSA-N 1,2-dichloro-3-isocyanatobenzene Chemical class ClC1=CC=CC(N=C=O)=C1Cl FYWJWWMKCARWQG-UHFFFAOYSA-N 0.000 description 1
RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-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
BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical class ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
ZVFNUQWYLXXSJM-UHFFFAOYSA-N 1-ethyl-2-isocyanatobenzene Chemical compound CCC1=CC=CC=C1N=C=O ZVFNUQWYLXXSJM-UHFFFAOYSA-N 0.000 description 1
BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
DKLKFEPNKANTKA-UHFFFAOYSA-N 10-hydroxydecyl 2-cyanoprop-2-enoate Chemical compound OCCCCCCCCCCOC(=O)C(=C)C#N DKLKFEPNKANTKA-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
FCDPKPULJHOKEK-UHFFFAOYSA-N 2-hydroxyethyl 2-cyanoprop-2-enoate Chemical compound OCCOC(=O)C(=C)C#N FCDPKPULJHOKEK-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
WMBNZUVQVIDOOR-UHFFFAOYSA-N 3,3,4-tripropyloxepan-2-one Chemical class CCCC1CCCOC(=O)C1(CCC)CCC WMBNZUVQVIDOOR-UHFFFAOYSA-N 0.000 description 1
CJNWCYZELLHABH-UHFFFAOYSA-N 3,3-dimethyloxan-2-one Chemical class CC1(C)CCCOC1=O CJNWCYZELLHABH-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 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
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
229920001651 Cyanoacrylate Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
DLJMATWNNUQYRQ-UHFFFAOYSA-N FC(CS(=O)(=O)[Sn]S(=O)(=O)CC(F)(F)F)(F)F Chemical compound FC(CS(=O)(=O)[Sn]S(=O)(=O)CC(F)(F)F)(F)F DLJMATWNNUQYRQ-UHFFFAOYSA-N 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 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
125000005250 alkyl acrylate group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
VGDKSWYVLAPXJL-UHFFFAOYSA-N bis(2-isocyanatoethyl) bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate Chemical compound C1C2C=CC1C(C(=O)OCCN=C=O)C2C(=O)OCCN=C=O VGDKSWYVLAPXJL-UHFFFAOYSA-N 0.000 description 1
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000013036 cure process Methods 0.000 description 1
NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011953 free-radical catalyst Substances 0.000 description 1
ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 description 1
LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
229940063557 methacrylate Drugs 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004632 polycaprolactone Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007670 refining Methods 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 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
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromonomer-Based Addition Polymer (AREA)
Paints Or Removers (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polyurethanes Or Polyureas (AREA)

CA000370814A 1980-03-21 1981-02-13 (n-substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters Expired CA1154455A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US132,650		1980-03-21
US06/132,650 US4340497A (en)	1980-03-21	1980-03-21	(N-Substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters

Publications (1)

Publication Number	Publication Date
CA1154455A true CA1154455A (en)	1983-09-27

Family

ID=22454975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000370814A Expired CA1154455A (en)	1980-03-21	1981-02-13	(n-substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters

Country Status (5)

Country	Link
US (1)	US4340497A (2)
EP (1)	EP0037314B2 (2)
JP (1)	JPS56145266A (2)
CA (1)	CA1154455A (2)
DE (1)	DE3162212D1 (2)

Families Citing this family (84)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4704470A (en) *	1981-09-02	1987-11-03	The Dow Chemical Company	Polymerizable antioxidants from isocyanatoalkyl esters of unsaturated carboxylic acids
AU557449B2 (en) *	1981-10-21	1986-12-24	Loctite Corporation	Gasket forming process and composition
US4504635A (en) *	1982-11-02	1985-03-12	Union Carbide Corporation	Process for the preparation of polymeric compositions
DE3345104A1 (de) *	1983-12-13	1985-06-13	Bayer Ag, 5090 Leverkusen	In ungesaettigte harze einpolymerisierbare arylamin-derivate, ihre herstellung und ihre verwendung als haertungsbeschleuniger
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- 1981-03-20 DE DE8181400436T patent/DE3162212D1/de not_active Expired
- 1981-03-20 JP JP3972581A patent/JPS56145266A/ja active Granted
- 1981-03-20 EP EP81400436A patent/EP0037314B2/en not_active Expired

Also Published As

Publication number	Publication date
EP0037314B2 (en)	1988-02-10
EP0037314A1 (en)	1981-10-07
DE3162212D1 (en)	1984-03-22
US4340497A (en)	1982-07-20
JPS56145266A (en)	1981-11-11
EP0037314B1 (en)	1984-02-15
JPS628429B2 (2)	1987-02-23

Legal Events

Date	Code	Title	Description
2000-09-27	MKEX	Expiry

Publication	Publication Date	Title
CA1154455A (en)	1983-09-27	(n-substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters
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JPS62285959A (ja)	1987-12-11	耐熱性光硬化型被覆組成物