CN117015560A - Compositions based on (meth) acrylate monomers - Google Patents
Compositions based on (meth) acrylate monomers Download PDFInfo
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- CN117015560A CN117015560A CN202280020268.4A CN202280020268A CN117015560A CN 117015560 A CN117015560 A CN 117015560A CN 202280020268 A CN202280020268 A CN 202280020268A CN 117015560 A CN117015560 A CN 117015560A
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- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 239000000178 monomer Substances 0.000 title claims abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000012949 free radical photoinitiator Substances 0.000 claims description 14
- 230000001070 adhesive effect Effects 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000853 adhesive Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 238000004132 cross linking Methods 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- -1 optical brighteners Substances 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000945 filler Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000005855 radiation Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000012764 mineral filler Substances 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 3
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000000518 rheometry Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- XYFXTIBDEAZMAH-UHFFFAOYSA-N 6-methoxycoumarin Natural products O1C(=O)C=CC2=C1C=CC=C2OC XYFXTIBDEAZMAH-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920001944 Plastisol Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- JUCDYAGBKUTTBC-UHFFFAOYSA-N [ethyl(phenyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(CC)C(=O)C1=C(C)C=C(C)C=C1C JUCDYAGBKUTTBC-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 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 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000004999 plastisol Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- BLDLNIJTYUZPCF-UHFFFAOYSA-N (2-methylmorpholin-2-yl)-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1(C)OCCNC1 BLDLNIJTYUZPCF-UHFFFAOYSA-N 0.000 description 1
- YCDUQXXFNZLWJU-CROMWVBPSA-N (2s,5r,6r)-6-[[(2r)-2-(4-hydroxyphenyl)-2-[[6-oxo-2-(4-sulfamoylanilino)-1h-pyrimidin-5-yl]carbamoylamino]acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)NC(C(N1)=O)=CN=C1NC1=CC=C(S(N)(=O)=O)C=C1 YCDUQXXFNZLWJU-CROMWVBPSA-N 0.000 description 1
- XVFXMRHAXWDKSU-UHFFFAOYSA-N 1,2-diphenyl-2-phenylmethoxyethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OCC1=CC=CC=C1 XVFXMRHAXWDKSU-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- JZKPKNSYAHAKJY-UHFFFAOYSA-N 1-[4-(4-benzoylphenyl)sulfanylphenyl]-2-methyl-2-(4-methylphenyl)sulfonylpropan-1-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C)(C)C(=O)C(C=C1)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 JZKPKNSYAHAKJY-UHFFFAOYSA-N 0.000 description 1
- DHAFFBOOYVWPBT-UHFFFAOYSA-N 1-chloro-4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2Cl DHAFFBOOYVWPBT-UHFFFAOYSA-N 0.000 description 1
- HDYFAPRLDWYIBU-UHFFFAOYSA-N 1-silylprop-2-en-1-one Chemical class [SiH3]C(=O)C=C HDYFAPRLDWYIBU-UHFFFAOYSA-N 0.000 description 1
- BKUSIKGSPSFQAC-RRKCRQDMSA-N 2'-deoxyinosine-5'-diphosphate Chemical compound O1[C@H](CO[P@@](O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(NC=NC2=O)=C2N=C1 BKUSIKGSPSFQAC-RRKCRQDMSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- WDFFWUVELIFAOP-UHFFFAOYSA-N 2,6-difluoro-4-nitroaniline Chemical compound NC1=C(F)C=C([N+]([O-])=O)C=C1F WDFFWUVELIFAOP-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXAMGWKESXGGNV-UHFFFAOYSA-N 7-(diethylamino)-1-benzopyran-2-one Chemical compound C1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 QXAMGWKESXGGNV-UHFFFAOYSA-N 0.000 description 1
- BBVARVTURNYWGV-UHFFFAOYSA-N 7-methyloctyl benzoate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1 BBVARVTURNYWGV-UHFFFAOYSA-N 0.000 description 1
- ODRDTKMYQDXVGG-UHFFFAOYSA-N 8-methoxycoumarin Natural products C1=CC(=O)OC2=C1C=CC=C2OC ODRDTKMYQDXVGG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-O Thiophenium Chemical compound [SH+]1C=CC=C1 YTPLMLYBLZKORZ-UHFFFAOYSA-O 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- ZQYCVIGMGPFQQS-UHFFFAOYSA-N [3-pentanoyloxy-2,2-bis(pentanoyloxymethyl)propyl] pentanoate Chemical compound CCCCC(=O)OCC(COC(=O)CCCC)(COC(=O)CCCC)COC(=O)CCCC ZQYCVIGMGPFQQS-UHFFFAOYSA-N 0.000 description 1
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 1
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012754 barrier agent Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- HORIEOQXBKUKGQ-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1CCCCC1C(=O)OCCCCCCC(C)C HORIEOQXBKUKGQ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 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
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- DKKXSNXGIOPYGQ-UHFFFAOYSA-N diphenylphosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(C=1C=CC=CC=1)C1=CC=CC=C1 DKKXSNXGIOPYGQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 239000003822 epoxy resin Substances 0.000 description 1
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- 239000003063 flame retardant Substances 0.000 description 1
- 150000002211 flavins Chemical class 0.000 description 1
- 150000008377 fluorones Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- GNNILMDCYQGMRH-UHFFFAOYSA-N formyl benzoate Chemical class O=COC(=O)C1=CC=CC=C1 GNNILMDCYQGMRH-UHFFFAOYSA-N 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LIIALPBMIOVAHH-UHFFFAOYSA-N herniarin Chemical compound C1=CC(=O)OC2=CC(OC)=CC=C21 LIIALPBMIOVAHH-UHFFFAOYSA-N 0.000 description 1
- JHGVLAHJJNKSAW-UHFFFAOYSA-N herniarin Natural products C1CC(=O)OC2=CC(OC)=CC=C21 JHGVLAHJJNKSAW-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229950010703 piroxicillin Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000004588 polyurethane sealant Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- KHDBMTLGTSGEEG-UHFFFAOYSA-M sodium;2-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=CC=C1S([O-])=O KHDBMTLGTSGEEG-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical compound C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical class OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention relates to a crosslinkable two-component composition comprising: -component a comprising: -a compound having the following formula (I):-at least one (meth) acrylate monomer M1 having one of the formulae (II), (III) or (IV); -component B comprising at least one compound having the following formula (V): r is R c ‑SO 2 ‑ ,Q + (V) and uses thereof.
Description
Technical Field
The present invention relates to a composition based on (meth) acrylate monomers.
The invention also relates to the use of said composition for repairing and/or semi-structural or structural bonding of materials in the transportation, marine, assembly, electronic or construction fields.
Technical Field
Acrylic compositions are known as reactive systems crosslinked by free radical polymerization. They are used as adhesives, binders and coatings. Free radical polymerization is typically initiated by a redox system, which leads to the generation of free radicals by redox reactions.
Most acrylic systems are two-component systems. The first component typically contains a reducing agent and a reactive monomer and the second component contains an oxidizing agent. Once the two components are mixed, the reducing agent causes the O-O bond of the organic peroxide to break and initiates polymerization.
Typically, (meth) acrylic compositions comprise a redox system of the peroxide (oxidizing agent)/tertiary amine (reducing agent) type. However, these systems may have storage stability problems in the presence of (meth) acrylate monomers.
There is a need for new (meth) acrylic compositions that allow a good compromise between reactivity and storage stability.
In addition, there is a need for new (meth) acrylic compositions having good adhesion properties.
Disclosure of Invention
A. Composition and method for producing the same
The present invention relates to a crosslinkable two-component composition comprising:
-component a comprising:
-a compound having one of the following formulas (Ia) or (Ib):
wherein:
-R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R a and R is b Independently of each other, represents a group selected from a hydrogen atom or a halogen atom, an alkyl group, a cycloalkyl group or an aryl group;
-R f represents perhaloalkyl or haloalkyl;
-X - represents an anion;
and
-at least one (meth) acrylate monomer M1 having one of the following formulae (II), (III) or (IV):
wherein:
-R 9 represents H or methyl;
-R 10 represents H, methyl or ethyl;
-p represents 0 or 1; and
-Z represents H, O, S, alkyl, benzyl, aryl or alkoxy;
y represents O, S, NH or CH 2 ；
Is a single bond or a double bond,
provided that when Z represents O, then the bondIs a double bond;
-component B comprising at least one compound having the following formula (V):
R c -SO 2 - ,Q + (V)
wherein:
-R c represents a group selected from: heteroaryl, aryl, alkyl, said heteroaryl, aryl, and alkyl being optionally substituted with at least one of the following groups: F. OH, C (O) OMe, NHC (O) Me, methyl (Me), CF 3 OH or SO 2 - ；
-Q + Represents selected from Li + 、Na + Or K + Is a cation of (a).
In the context of the present invention, the term "alkyl" refers to a straight or branched chain group, preferably containing 1 to 20 carbon atoms. For example, methyl, ethyl and propyl groups may be mentioned.
In the context of the present invention, the term "aryl" refers to a mono-or bicyclic aromatic group, preferably containing from 6 to 12 carbon atoms. For example, phenyl may be mentioned.
In the context of the present invention, the term "cycloalkyl" refers to a saturated mono-or polycyclic ring system, preferably a mono-or bicyclic ring system, preferably containing 3 to 12 carbon atoms, which rings may be bridged or fused in pairs, such as cyclopropyl, cyclopentyl, cyclohexyl or norbornyl.
In the context of the present invention, the term "alkoxy" refers to an-O-alkyl group.
Component A
Compounds of formula (Ia) or (Ib)
Component A comprises a compound of formula (Ia) or (Ib) as defined above.
Anions X - Can be selected from FSO 3 - 、CF 3 SO 3 - 、CF 2 HSO 3 - 、Cl - 、Br - 、BF 4 - 、BF 3 Cl - And PF (physical filter) 6 - 。
In the above formula (Ia) or (Ib), R f Haloalkyl may be represented. For example, it may be a fluoroalkyl group, such as CHF 2 Or CH (CH) 2 F。
Preferably, in formula (Ia) or (Ib), R f Represents perfluoroalkyl groups, even more preferably CF 3 、C 2 F 5 、C 3 F 7 Or C 4 F 9 . According to a particularly preferred embodiment, R f Representing CF 3 。
The compound of formula (Ia) or (Ib) may be selected from compounds wherein:
-R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R a and R is b Independently of each other, represents a group selected from hydrogen or halogen atoms, or alkyl groups, preferably hydrogen or fluorine atoms;
-R f represents perfluoroalkyl or fluoroalkyl, preferably perfluoroalkyl;
-X - represents an anion, preferably selected from FSO3-, CF 3 SO 3-and BF4-.
According to a preferred embodiment, component a comprises a compound of formula (Ia), in particular selected from the group consisting of:
even more preferably from one of the following compounds:
the compounds of formula (Ia) can be prepared as described in WO 2016/107578. The compounds of formula (Ib) may be prepared as described in WO 2011/01337.
The total content of compounds of formula (Ia) or (Ib) may be from 0.05 wt% to 5.0 wt%, preferably from 0.1 wt% to 3.0 wt%, even more preferably from 0.1 wt% to 1.5 wt%, relative to the total weight of the crosslinkable two-component composition.
(meth) acrylate monomer M1
Component A according to the invention comprises at least one (meth) acrylate monomer M1 having one of the following formulae (II), (III) or (IV):
wherein:
-R 9 represents H or methyl;
-R 10 represents H, methyl or ethyl;
-p represents 0 or 1; and
-Z represents H, O, S, alkyl, benzyl, aryl or alkoxy;
y represents O, S, NH or CH 2 ；
Is a single bond or a double bond,
provided that when Z represents O, then the bondIs a double bond.
The (meth) acrylate monomer M1 may be selected from the following monomers:
the monomers M1 are preferably selected from the monomers of the formulae (II) or (III).
More preferably it is one of the following compounds or mixtures thereof:
the total content of the (meth) acrylate monomers M1 in the component a may be greater than or equal to 30 wt% relative to the total weight of the component a.
The content of the (meth) acrylate monomer M1 in the crosslinkable two-component composition according to the invention may be from 30 to 99% by weight, preferably from 50 to 99% by weight, even more preferably from 75 to 99% by weight, relative to the total weight of the crosslinkable two-component composition.
Component B
Component B comprises at least one compound having the formula (V):
R c -SO 2 - ,Q + (V)
wherein:
-R c represents a group selected from: heteroaryl, arylalkyl, aryl, alkyl, said heteroaryl, arylalkyl, aryl, and alkyl being optionally substituted with at least one of the following groups: F. OH, C (O) OMe, NHC (O) Me, methyl (Me), CF 3 OH or SO 2 - ；
-Q + Represents selected from Li + Na+ or K + Is a cation of (a).
According to a preferred embodiment, the compound of formula (V) is selected from the group consisting of compounds wherein:
-Q + as previously defined, Q + Preferably represents Na + Or K + And even more preferably represents Na + ，
-R c Represents a group selected from heteroaryl or aryl.
The compound of formula (V) may be selected from the following compounds:
according to a preferred embodiment, the compound of formula (V) is selected from the following compounds:
the total content of the compounds of formula (V) as defined above may be from 0.05 to 5.0% by weight.
The total content of compounds of formula (V) as defined above may be from 0.1 to 5.0 wt%, preferably from 0.1 to 3.0 wt%, even more preferably from 0.1 to 1.5 wt%, relative to the total weight of the crosslinkable two-component composition according to the invention.
In the crosslinkable two-component composition according to the invention, the molar ratio of the compound of formula (I)/the compound of formula (V) may be from 0.01 to 1.2, preferably from 0.02 to 1.1, preferably from 0.04 to 1.0, even more preferably from 0.08 to 0.8.
Composition and method for producing the same
According to a preferred embodiment, the crosslinkable two-component composition does not comprise a peroxide.
Preferably, the two-component composition according to the invention does not comprise any alkyl (meth) acrylate, such as methyl (meth) acrylate or benzyl (meth) acrylate.
The crosslinkable two-component composition according to the invention may comprise at least one additive selected from the group consisting of catalysts, fillers, antioxidants, light/UV absorbers, metal deactivators, antistatic agents, antifogging agents, foaming agents, biocides, plasticizers, lubricants, emulsifiers, dyes, pigments, rheology agents, impact modifiers, adhesion promoters, optical brighteners, flame retardants, barrier agents, nucleating agents, solvents, polymerization inhibitors and mixtures thereof.
These additives may be present in component a and/or component B of the composition according to the invention.
As examples of plasticizers that can be used, mention may be made of any plasticizer commonly used in the adhesive field, such as epoxy resins, phthalates, benzoates, trimethylol propane esters, trimethylol ethane esters, trimethylol methane esters, glycerol esters, pentaerythritol esters, naphthenic mineral oils, adipates, cyclohexyl dicarboxylic esters, paraffinic oils, natural oils (optionally epoxidized), polypropylene, polybutenes, hydrogenated polyisoprenes and mixtures thereof.
For example, it is possible to use:
diisodecyl phthalate, e.g. by BASF under the name Palatinol TM The DIDP is sold as such,
esters of alkylsulfonic acids and phenols, e.g. by Lanxess CorpIs sold in the form of a roll,
diisononyl 1, 2-cyclohexanedicarboxylate, e.g. under the name Hexamoll by BASFIs sold in the form of a roll,
pentaerythritol tetrapentanoate, e.g. by Perston under the name Pevalen TM Is sold in the form of a roll,
for example by the company Arkema under the name7170 epoxidized soybean oil.
As examples of (thixotropic) rheology agents that can be used, any rheology agent conventionally used in the field of adhesive compositions may be mentioned.
Preferably, the thixotropic agent is selected from:
PVC plastisol, corresponding to a suspension of PVC in a plasticizer miscible with PVC, obtained in situ by heating to a temperature of 60 to 80 ℃. These plastisols can be those described in particular in publication Polyurethane Sealants, robertM.Evans, ISBN 087762-998-6
Fumed silica, e.g. by Wacker under the nameN20 is sold;
urea derivatives resulting from the reaction of aromatic diisocyanate monomers such as 4,4' -MDI with aliphatic amines such as butylamine. The preparation of such urea derivatives is described in particular in patent application FR 1591172;
micronised amide waxes, for example sold by ArkemaSLT or->SLA。
The composition according to the invention may also comprise at least one organic and/or mineral filler.
The mineral fillers which can be used are advantageously selected to improve the mechanical properties of the compositions according to the invention in the crosslinked state.
As examples of mineral fillers that can be used, any mineral filler commonly used in the field of adhesive compositions can be used. These fillers are generally provided in the form of particles of different geometries. They may be, for example, spherical or fibrous or may have an irregular shape.
Preferably, the filler is selected from the group consisting of clay, quartz, carbonate filler, kaolin, gypsum, clay, and mixtures thereof; preferably, the filler is selected from carbonate fillers, such as alkali or alkaline earth metal carbonates, and more preferably calcium carbonate or chalk.
These fillers may be untreated or treated, for example, with organic acids such as stearic acid or mixtures of organic acids consisting essentially of stearic acid.
Hollow mineral microspheres, such as hollow glass microspheres, and more particularly those made of sodium calcium borosilicate or aluminosilicate, may also be used.
The composition according to the invention may further comprise at least one adhesion promoter, preferably selected from silanes, such as aminosilanes, epoxysilanes or acryloylsilanes, or phosphate-based adhesion promoters, such as 2-hydroxyethyl methacrylate phosphate, 2-methacryloxyethyl phosphate, bis (2-methacryloxyethyl phosphate), 2-acryloxyethyl phosphate, bis (2-acryloxyethyl phosphate), methyl- (2-methacryloxyethyl phosphate), ethyl- (2-methacryloxyethyl phosphate), 2-hydroxyethyl methacrylate mono-and di-phosphate mixtures.
When pigments are present in the composition, their content is preferably less than or equal to 3 wt%, more preferably less than or equal to 2 wt%, relative to the total weight of the composition. When present, the pigment may, for example, comprise from 0.1 wt% to 3 wt% or from 0.4 wt% to 2 wt% of the total weight of the composition. The pigment may be an organic or inorganic pigment.
For example, the pigment is TiO 2 In particular sold by Kronos company2059。
As polymerization inhibitors, there may be mentioned, for example, 4-hydroxy-2, 6-tetramethylpiperidinyloxy or TEMPOL (CAS: 2226-96-2) sold by the company BASF and Evonik.
The composition may comprise at least one UV stabilizer or antioxidant in an amount of 0.1% to 3%, preferably 1% to 3% by weight. These compounds are generally introduced to protect the composition from degradation by reaction with oxygen which is readily formed by thermal or light action. These compounds may include primary antioxidants that trap free radicals. The primary antioxidants may be used alone or in combination with other secondary antioxidants or UV stabilizers.
Mention may be made, for example1010、/>B561、/>245、/>168、/>328 or Tinuvin TM 770, which are sold by BASF.
The crosslinkable two-component composition may further comprise a free-radical photoinitiator, which may be present in component a and/or component B of the composition. The radical photoinitiator is in particular an additional compound for the components of the claimed two-component composition.
The composition according to the invention may comprise from 0.1% to 5% by weight, preferably from 0.5% to 3% by weight, even more preferably from 0.5% to 1.5% by weight, relative to the total weight of the composition, of a free radical photoinitiator.
The free-radical photoinitiator is preferably contained in component a.
The free radical photoinitiator may be any free radical photoinitiator known to those skilled in the art. Under the action of UV/visible radiation, the radical photoinitiators generate radicals responsible for initiating the photopolymerization reaction and in particular make it possible to increase the efficiency of the photopolymerization reaction. This is, of course, selected based on the light source used (based on its ability to effectively absorb the selected radiation). For example, a suitable free radical photoinitiator will be selected from its ultraviolet/visible absorption spectrum. Advantageously, the free radical photoinitiator is suitable for use with a radiation source emitting in the near region of visible light. Advantageously, the UV or visible radiation source may be a broad spectrum UVA-centered lamp of the LED or dellux 03S type.
The free radical photoinitiator may be selected from the group consisting of:
-a type I free radical photoinitiator selected from:
-acetophenone and alkoxyacetophenone families, such as 2, 2-dimethoxy-2-phenylacetophenone and 2-diethyl-2-phenylacetophenone;
a family of hydroxyacetophenones, such as 2, 2-dimethyl-2-hydroxyacetophenone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-4 '- (2-hydroxyethoxy) -2-methylpropophenone and 2-hydroxy-4' - (2-hydroxypropoxy) -2-methylpropophenone;
-family of alkylaminoacetophenones, such as 2-methyl-4' - (methylthio) -2-morpholinophenone, 2-benzyl-2- (dimethylamino) -4-morpholino Ding Bentong and 2- (4-methylbenzyl) -2- (dimethylamino) -4-morpholino Ding Bentong;
a family of benzoin ethers, such as benzoin benzyl ether, benzoin methyl ether and benzoin isopropyl ether;
phosphine oxide families such as diphenyl (2, 4, 6-Trimethylbenzoyl) Phosphine Oxide (TPO), ethyl (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide (TPO-L) and bis (2, 6-dimethoxybenzoyl) -2, 4-trimethylphenylphosphine oxide (BAPO);
a metallocene family such as ferrocene, bis (. Eta.5-2, 4-cyclopentadienyl-1-yl) bis (2, 6-difluoro) -3- (1H-pyrrol-1-yl) phenyl) titanium and (cumene) (cyclopentadienyl) iron hexafluorophosphate;
-type II radical photoinitiators are selected from:
a family of benzophenones, for example 4-phenylbenzophenone, 4- (4' -methylphenylsulfanyl) benzophenone or 1- [4- [ (4-benzoylphenyl) thio ] phenyl ] -2-methyl-2- [ (4-methylphenyl) sulfonyl ] -1-propanone;
a thioxanthone family such as Isopropylthioxanthone (ITX), 2, 4-diethylthioxanthone, 2, 4-dimethylthioxanthone, 2-chlorothioxanthone and 1-chloro-4-isopropylthioxanthone;
a family of benzoyl formates, such as methyl benzoyl formate;
-dibenzylidene ketone family, such as p-dimethylaminoketone;
a coumarin family such as 5-and 7-methoxycoumarin, 7-diethylaminocoumarin and N-phenylglycine coumarin;
-free radical photoinitiators of the dye family, such as triazines, fluorones, cyanines, basic safranins, 4,5,6, 7-dichloro-3 ',6' -dihydroxy-2 ',4',5',7' -tetraiodo-3H-spiro [ isobenzofuran-1, 9' -xanthen ] -3-one, pyrylium and thiopyrylium, thiazines, flavins, piroxicillin, oxazine or rhodamine;
-and mixtures thereof.
Preferably, the free radical photoinitiator is selected from the phosphine oxide family, such as diphenyl- (2, 4, 6-Trimethylbenzoyl) Phosphine Oxide (TPO), ethyl- (2, 4, 6-trimethylbenzoyl) phenylphosphine oxide (TPO-L) and bis (2, 6-dimethoxybenzoyl) -2, 4-trimethylphenylphosphine oxide (BAPO).
For example, when the UV or visible radiation source is an LED, the free radical photoinitiator may be selected from 2,4, 6-trimethylbenzoyl diphenylphosphine or TPO, such as that available from Lambson under commercial reference numbersTPO obtained (CAS: 75980-60-8) TPO, (2, 4, 6-trimethylbenzoyl) ethyl phenylphosphinate or TPO-L, e.g., commercially available from LambsonTPO-L is obtained (CAS: 84434-11-7), phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide or BAPO (CAS: 162881-26-7), for example from BASF under the trade name->819, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone (CAS: 119313-12-1), for example, commercially available from BASF369 obtained, 2-methyl-1- [4- (methylthio) phenyl ]]-2- (4-morpholinyl) -1-propanone (CAS: 71868-10-5), which can be obtained, for example, from BASF under the trade name +.>907, 1-hydroxycyclohexyl phenyl ketone (CAS: 947-19-3), e.g., as obtainable from BASF is commercially numbered->184 are obtained commercially, 2-isopropylthioxanthone or ITX (CAS: 5495-84-1), for example as described in reference number +.>Obtained under 2-ITX, or a mixture thereof.
When the composition according to the invention comprises a free radical photoinitiator, the total content of compounds of formula (Ia) or (Ib) may be from 0.05 to 5.0 wt%, preferably from 0.05 to 3.0 wt%, more preferably from 0.05 to 1.0 wt%, even more preferably from 0.05 to 0.5 wt%, and the total content of compounds of formula (V) may be from 0.05 to 5.0 wt%, preferably from 0.05 to 3.0 wt%, more preferably from 0.05 to 1.0 wt%, even more preferably from 0.05 to 0.5 wt%, relative to the total weight of the crosslinkable two-component composition according to the invention.
According to a preferred embodiment, the composition according to the invention does not comprise any peroxide.
In the composition according to the invention, the component A/component B volume ratio may be from 20/1 to 1/1, preferably from 10/1 to 1/1.
B. Instant kit
The invention also relates to a ready-to-use kit comprising, packaged in two separate compartments, a component a as defined above on the one hand and a component B as defined above on the other hand. For example, it may be a two-component cartridge.
In fact, the composition according to the invention may be in the form of two components, for example in a ready-to-use kit, in proportions suitable for direct mixing of the two components (for example using a metering pump), component a contained in a first compartment or cartridge on the one hand and component B contained in a second compartment or cartridge on the other hand.
According to one embodiment of the invention, the kit further comprises one or more means for mixing components a and B. Preferably, the mixing means are selected from metering pumps or static mixers of a diameter suitable for the amount used.
C. Use of a composition
The invention also relates to the use of a crosslinkable two-component composition as defined above as an adhesive, an adhesive or a coating, preferably as an adhesive.
The invention also relates to the use of said composition for repairing materials and/or for structural or semi-structural bonding in the fields of transportation, motor vehicles (cars, buses or trucks), assembly, ships, electronics or architecture.
The invention relates to a method for assembling two substrates by bonding, comprising:
-applying a composition obtained by mixing components a and B as defined above to at least one of the two substrates to be assembled; however
-bringing the two substrates into effective contact;
-crosslinking the composition.
The crosslinking step may be carried out at a temperature of from 0 ℃ to 200 ℃, preferably from 10 ℃ to 150 ℃, preferably from 23 to 80 ℃, in particular from 20 ℃ to 25 ℃.
Suitable substrates are, for example, inorganic substrates, such as concrete, metals or alloys (e.g. aluminum alloys, steel, nonferrous metals and galvanized metals); or organic substrates such as wood, plastics, e.g. PVC, polycarbonate, PMMA, polyethylene, polypropylene, polyester, epoxy; substrates made of painted metals and composites.
The crosslinking may be carried out under electromagnetic radiation, for example using a UV radiation source or using LEDs.
The crosslinking step under electromagnetic radiation may be carried out at a wavelength of more than 300nm, preferably 360nm to 680nm, even more preferably 360nm to 420 nm.
The compositions of the present invention are advantageously stable upon storage.
The composition according to the invention advantageously achieves a good compromise between storage stability and high reactivity.
The composition according to the invention advantageously has good adhesive properties after crosslinking.
Furthermore, the surface of the crosslinking composition is advantageously fast drying and may not be tacky, which in particular makes it possible to increase the productivity of the industrial process.
All the embodiments described above can be combined with each other. In particular, the different above-mentioned ingredients of the composition, in particular the preferred embodiments of the composition, may be combined with each other.
In the context of the present invention, the term "between x and y" or "x to y" refers to the range in which the endpoints x and y are included. For example, a range "between 0% and 25% specifically includes values of 0% and 25%.
The invention is now described in the following examples, which are given purely by way of illustration and should not be interpreted as limiting the scope of the invention.
Examples
The following ingredients were used:
531: cyclic trimethylolpropane formal acrylate sold by Acomax (CAS: 66492-51-1);
thiophenium I:5- (trifluoromethyl) dibenzothiophenium, 1-trifluoromethanesulfonic acid salt (CAS: 129946-88-9), available from Sigma-Aldrich;
visiomer Glyfoma (CAS: 1620329-57-8), sold by Evonik;
thiophene III:2, 8-difluoro-5-trifluoromethyl dibenzothiophenium 1, 1-trifluoromethane sulfonate (CAS: 1961266-44-3), obtained from TCI chemicals;
sodium toluene sulfinate (CAS: 824-79-3), available from Sigma-Aldrich;
sodium benzene sulfinate (CAS: 873-55-2), available from Sigma-Aldrich;
-Visiomer benzyl methacrylate (CAS: 2495-37-6), available from Evonik;
-RETIC TM BP50, obtainable from Luperox (benzoyl peroxide in isononyl benzoate/ethylene glycol mixture);
bisomer PTE (CAS: 103671-44-9), sold by GEO Specialty Chemicals;
matte: (difluoromethyl) bis (2, 5-dimethylphenyl) sulfonium tetrafluoroborate (CAS: 2133476-51-2), which is available from TCI.
Example 1: preparation of composition 1
The ingredients of component a were mixed in the proportions shown in the table below at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
The different ingredients constituting component B were mixed in the proportions shown in the following table at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
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UsingThe Mixpac mixer mixes component a and component B at a volume ratio of 1:1 at an ambient temperature of 23 ℃.
Example 2: preparation of composition 2
The ingredients of component a were mixed in the proportions shown in the table below at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
The different ingredients constituting component B were mixed in the proportions shown in the following table at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
UsingThe Mixpac mixer mixes component a and component B at a volume ratio of 1:1 at an ambient temperature of 23 ℃.
Example 3: preparation of composition 3
The ingredients of component a were mixed in the proportions shown in the table below at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
The different ingredients constituting component B were mixed in the proportions shown in the following table at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
Component A and component B useThe Mixpac mixer was mixed at an ambient temperature of 23℃in a volume ratio of 1:1.
Example 4: preparation of composition 4 (comparative example)
The ingredients of component a were mixed in the proportions shown in the table below at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
The different ingredients constituting component B were mixed in the proportions shown in the following table at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
Component A and component B useThe Mixpac mixer was mixed at an ambient temperature of 23℃in a volume ratio of 1:1.
Example 5: preparation of composition 5 (comparative example)
The ingredients of component a were mixed in the proportions shown in the table below at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
The different ingredients constituting component B were mixed in the proportions shown in the following table at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
Component A and component B useThe Mixpac mixer was mixed at an ambient temperature of 23℃in a volume ratio of 1:1.
Example 6: preparation of composition 6 (comparative example)
The ingredients of component a were mixed in the proportions shown in the table below at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
The different ingredients constituting component B were mixed in the proportions shown in the following table at a temperature of 23 ℃ in a mixer maintaining continuous stirring and under nitrogen.
Component A and component B useThe Mixpac mixer was mixed at an ambient temperature of 23℃in a volume ratio of 1:1.
Example 7: properties of the composition
The adhesion test was performed under the following conditions:
compositions No.1, 2, 3, 4,5 and 6 (by use in examples 1,2, 3, 4,5 and 6, respectively)Obtained by mixing components a and B in a Mixpac mixer) applied to a first microscope slide (25 x76 mm);
-fixing a second microscope slide (25 x76 mm) to the first slide receiving compositions No.1, 2, 3, 4,5 and 6;
a step of sliding the two microscope slides to allow a uniform distribution of the compositions No.1, 2, 3, 4,5 and 6 between the two slides (here reducing the oxygen exposure).
The time from this was recorded when it was no longer possible to separate the two slides.
Reactivity (exotherm) was continuously analyzed using pyrometer and thermal imaging. Gel time (or lag time) is the time required to initiate polymerization of the sample.
An Omega OS552-V1-6 industrial infrared thermometer (OmegaInc., stamford, CT) generates a time/temperature profile for the polymerization of 2g (about 4.0mm height) and 0.25g (1.4 mm height).
The results are summarized in the following table:
from this table, it is seen that compositions No.1, 2 and 3 (according to the invention) advantageously polymerize rapidly (after mixing components A and B) due to the short gel times (48, 180 and 60 seconds, respectively). On the other hand, comparative compositions No.4 and 5 (examples 4 and 5) were observed not to polymerize in the open air. Composition No.6 did polymerize, but in contrast to part B of examples 1,2 and 3, part B was unstable and polymerized over time (24 h), which made composition No.6 practically unusable in commercial products. Furthermore, comparative composition 6 resulted in long gel times relative to compositions No.1, 2 and 3 according to the invention: 246 seconds.
Moreover, compositions No.1, 2 and 3 advantageously resulted in adhesion with a fast setting time compared to composition No.4, which did not allow adhesion.
Finally, it was observed that for compositions No.1 (example 1) and No.2 (example 2) and No.3 (example 3), the polymers obtained after crosslinking were advantageously surface-dried (non-tacky).
Claims (15)
1. A crosslinkable two-part composition comprising:
-component a comprising:
-a compound having one of the following formulas (Ia) or (Ib):
wherein:
-R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R a and R is b Independently of each other, represents a group selected from a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group or an aryl group;
-R f represents perhaloalkyl or haloalkyl;
-X - represents an anion;
and
-at least one (meth) acrylate monomer M1 having one of the following formulae (II), (III) or (IV):
wherein:
-R 9 represents H or methyl;
-R 10 represents H, methyl or ethyl;
-p represents 0 or 1; and
-Z represents H, O, S, alkyl, benzyl, aryl or alkoxy;
y represents O, S, NH or CH 2 ；
Is a single bond or a double bond,
provided that when Z represents O, then the bondIs a double bond;
-component B comprising at least one compound having the following formula (V):
R c -SO 2 - ,Q + (V)
wherein:
-R c represents a group selected from heteroaryl, aryl, alkyl, said heteroaryl, aryl and alkyl being optionally substituted with at least one of the following groups: F. OH, C (O) OMe, NHC (O) Me, methyl (Me), CF 3 OH or SO 2 - ；
-Q + Represents selected from Li + 、Na + Or K + Is a cation of (a).
2. The composition according to claim 1, wherein in formula (Ia) or (Ib), the anion X - Selected from FSO 3 - 、CF 3 SO 3 - 、CF 2 HSO 3 -。 、Cl - 、Br - 、BF 4 - 、BF 3 Cl - 、PF 6 - 。
3. The composition according to claim 1 or 2, characterized in that in formula (Ia) or (Ib):
-R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R a and R is b Independently of each other, represents a group selected from a hydrogen atom, a halogen atom or an alkyl group, preferably a hydrogen or fluorine atom;
-R f represents perfluoroalkyl or fluoroalkyl, preferably perfluoroalkyl;
-X - representing yinIons, preferably selected from FSO 3 - 、CF 3 SO 3 - And BF 4 - 。
4. A composition according to any one of claims 1 to 3, wherein the compound of formula (Ia) is selected from the group consisting of:
5. the composition according to any one of claims 1 to 4, wherein the total content of compounds of formula (Ia) or (Ib) is from 0.05 to 5.0 wt%, preferably from 0.1 to 3.0 wt%, more preferably from 0.1 to 1.5 wt%, relative to the total weight of the crosslinkable two-component composition.
6. Composition according to any one of claims 1 to 5, characterized in that the (meth) acrylate monomer M1 is chosen from the following monomers:
7. composition according to any one of claims 1 to 6, characterized in that the total content of (meth) acrylate monomers M1 is from 30 to 99% by weight, preferably from 50 to 99% by weight, and more preferably from 75 to 99% by weight, relative to the total weight of the crosslinkable two-component composition.
8. Composition according to any one of claims 1 to 7, characterized in that the compound of formula (V) is selected from those in which Rc represents a group selected from heteroaryl or aryl.
9. Composition according to any one of claims 1 to 7, characterized in that the compound of formula (V) is chosen from the following compounds:
10. composition according to any one of claims 1 to 9, characterized in that the compound of formula (V) is chosen from the following compounds:
11. composition according to any one of claims 1 to 10, characterized in that the total content of compounds of formula (V) is from 0.1% to 5.0% by weight, preferably from 0.1% to 3.0% by weight, and more preferably from 0.1% to 1.5% by weight, relative to the total weight of the crosslinkable two-component composition.
12. Composition according to any one of claims 1 to 11, characterized in that it does not comprise a peroxide.
13. Composition according to any one of claims 1 to 12, characterized in that it further comprises a free radical photoinitiator.
14. Use of a composition as defined in any one of claims 1 to 13 as an adhesive, an adhesive or a coating, preferably as an adhesive.
15. A method of assembling two substrates by bonding, comprising:
-applying a composition obtained by mixing components a and B as defined in any one of claims 1 to 13 onto at least one of the two substrates to be assembled; then
-bringing the two substrates into effective contact; and
-crosslinking the composition.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FRFR2102661 | 2021-03-17 | ||
| FR2105517A FR3120872A1 (en) | 2021-03-17 | 2021-05-27 | Composition based on (meth)acrylate monomers |
| FRFR2105517 | 2021-05-27 | ||
| PCT/FR2022/050473 WO2022195221A1 (en) | 2021-03-17 | 2022-03-16 | Composition based on (meth)acrylate monomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117015560A true CN117015560A (en) | 2023-11-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280020268.4A Pending CN117015560A (en) | 2021-03-17 | 2022-03-16 | Compositions based on (meth) acrylate monomers |
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| Country | Link |
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| CN (1) | CN117015560A (en) |
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2022
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