JP2014162749A - 高感度(メタ)アクリレート及びラジカル硬化材料 - Google Patents
高感度(メタ)アクリレート及びラジカル硬化材料 Download PDFInfo
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- JP2014162749A JP2014162749A JP2013034935A JP2013034935A JP2014162749A JP 2014162749 A JP2014162749 A JP 2014162749A JP 2013034935 A JP2013034935 A JP 2013034935A JP 2013034935 A JP2013034935 A JP 2013034935A JP 2014162749 A JP2014162749 A JP 2014162749A
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- Prior art keywords
- acrylate
- meth
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- radical
- sensitivity
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 163
- 239000000463 material Substances 0.000 title claims abstract description 76
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 230000035945 sensitivity Effects 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002184 metal Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 20
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 14
- 230000000704 physical effect Effects 0.000 abstract description 8
- 230000002411 adverse Effects 0.000 abstract description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- -1 acrylate compound Chemical class 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 30
- 239000012948 isocyanate Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000001723 curing Methods 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 19
- 239000012986 chain transfer agent Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 7
- 229920006362 Teflon® Polymers 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 238000010526 radical polymerization reaction Methods 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 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 6
- 238000012546 transfer Methods 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 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 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 3
- 208000034189 Sclerosis Diseases 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- QDERNBXNXJCIQK-UHFFFAOYSA-N ethylisopropylamiloride Chemical compound CCN(C(C)C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl QDERNBXNXJCIQK-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 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 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 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
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- YBMAWNCLJNNCMV-PAMPIZDHSA-L (z)-1,1,1,5,5,5-hexafluoro-4-oxopent-2-en-2-olate;nickel(2+) Chemical compound [Ni+2].FC(F)(F)C(/[O-])=C/C(=O)C(F)(F)F.FC(F)(F)C(/[O-])=C/C(=O)C(F)(F)F YBMAWNCLJNNCMV-PAMPIZDHSA-L 0.000 description 1
- KFDRXQXGGQXFNP-DERJAXIWSA-J (z)-1,2-dicyanoethene-1,2-dithiolate;nickel(2+);tetrabutylazanium Chemical compound [Ni+2].N#CC(/[S-])=C(/[S-])C#N.N#CC(/[S-])=C(/[S-])C#N.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC KFDRXQXGGQXFNP-DERJAXIWSA-J 0.000 description 1
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-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
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- HSKPJQYAHCKJQC-UHFFFAOYSA-N 1-ethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC HSKPJQYAHCKJQC-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-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
- UOCMXZLNHQBBOS-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol zinc Chemical compound [Zn].Oc1ccccc1-c1nc2ccccc2o1.Oc1ccccc1-c1nc2ccccc2o1 UOCMXZLNHQBBOS-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- YPGYFPCHCFXUKD-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)COC(=O)C=C YPGYFPCHCFXUKD-UHFFFAOYSA-N 0.000 description 1
- SMWOQEYXSYVTQR-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid copper Chemical compound [Cu].[Cu].OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O SMWOQEYXSYVTQR-UHFFFAOYSA-N 0.000 description 1
- YCPMSWJCWKUXRH-UHFFFAOYSA-N 2-[4-[9-[4-(2-prop-2-enoyloxyethoxy)phenyl]fluoren-9-yl]phenoxy]ethyl prop-2-enoate Chemical compound C1=CC(OCCOC(=O)C=C)=CC=C1C1(C=2C=CC(OCCOC(=O)C=C)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YCPMSWJCWKUXRH-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
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- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
- LLVONELOQJAYBZ-UHFFFAOYSA-N tin(ii) phthalocyanine Chemical compound N1=C(C2=CC=CC=C2C2=NC=3C4=CC=CC=C4C(=N4)N=3)N2[Sn]N2C4=C(C=CC=C3)C3=C2N=C2C3=CC=CC=C3C1=N2 LLVONELOQJAYBZ-UHFFFAOYSA-N 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
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JGOIIPRSFZFFHG-UHFFFAOYSA-N trimethyl(2-tributylstannylethynyl)silane Chemical compound CCCC[Sn](CCCC)(CCCC)C#C[Si](C)(C)C JGOIIPRSFZFFHG-UHFFFAOYSA-N 0.000 description 1
- HDWHGDDNMJOCCU-UHFFFAOYSA-N trimethyl(pyridin-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=N1 HDWHGDDNMJOCCU-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- CYDXJXDAFPJUQE-SYWGCQIGSA-L zinc;(e)-4-oxopent-2-en-2-olate Chemical compound [Zn+2].C\C([O-])=C/C(C)=O.C\C([O-])=C/C(C)=O CYDXJXDAFPJUQE-SYWGCQIGSA-L 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- C08L35/00—Compositions of 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 a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
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- C08L33/04—Homopolymers or copolymers of esters
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Abstract
Description
下記式1に示す構造を分子内に1つ以上有し、ラジカル硬化に用いることで、感度が向上することを要旨とするものである。
〔(メタ)アクリレート〕
・IBA:イソボルニルアクリレート
・DPGA:ジプロピレングリコールジアクリレート
・HPGA:ヘプタプロピレングリコールジアクリレート
・STA(合成例1)
・IPHA(合成例2)
・IPIPA(合成例3)
・EIPA(合成例4)
・BIPA(合成例5)
・IPTA(合成例6)
〔光(紫外線)重合開始剤〕
・HCHPK:1−ヒドロキシシクロヘキシルフェニルケトン
〔熱重合開始剤〕
・AIBN:アゾビスイソブチロニトリル
〔含金属化合物〕
・BPDZ:ビス(2,4−ペンタンジオナート)亜鉛(II)
攪拌機を備えた反応容器に、ステアリルイソシアネート(MW295.5)100g(0.338mol)とヒドロキシプロピルアクリレート(MW130.1)44g(0.338mol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT−IRを測定して2300cm−1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。その吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。得られたアクリレートは式4に示す化合物である。これをSTAとした。
攪拌機を備えた反応容器に、ヘキサメチレンジイソシアネート(MW168.1)100g(0.595mol)とヒドロキシプロピルアクリレート(MW130.1)154.8g(1.190mol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT−IRを測定して2300cm−1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。その吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。得られたアクリレートは式5に示す化合物である。これをIPHAとした。
攪拌機を備えた反応容器に、イソホロンジイソシアネート(MW222.3)132.3g(0.595mol)とヒドロキシプロピルアクリレート(MW130.1)154.8g(1.190mol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT−IRを測定して2300cm−1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。その吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。得られたアクリレートは式6に示す化合物である。これをIPIPAとした。
ヒドロキシプロピルアクリレートをヒドロキシエチルアクリレート(MW116.1)138.2g(1.190mol)に変更した以外は合成例3と同様の操作で合成し、無色粘調性液体を得た。得られたアクリレートは式7に示す化合物である。これをEIPAとした。
ヒドロキシプロピルアクリレートを4−ヒドロキシブチルアクリレート(MW144.2)171.6g(1.190mol)に変更した以外は合成例3と同様の操作で合成し、無色粘調性液体を得た。得られたアクリレートは式8に示す化合物である。これをBIPAとした。
イソホロンジイソシアネートをトリレンジイソシアネート(MW174.16)103.6g(0.595mol)に変更した以外は合成例3と同様の操作で合成し、無色粘調性液体を得た。得られたアクリレートは式9に示す化合物である。これをIPTAとした。
表1又は表2に示された組成物それぞれを、底面をテフロン(テフロンは登録商標である)栓で塞いだ内径10mmの硬質テフロンチューブ中に液面の高さが50mmになるように入れ、表1組成の光硬化材料に関しては、上面からUVランプ(SEN特殊光源社製100mW/cm2)で2秒間紫外線照射を行い、表2組成の熱硬化材料に関しては、上面から約100℃の熱風を15秒間あてた。ラジカル重合反応が起こっていれば組成物は硬化して固化するため、底面のテフロン栓を抜いた際、ラジカル重合反応が起こっていない液体のままの組成物は流れ落ち、固化物(ラジカル重合物)はテフロンチューブ中に残留する。すなわち、テフロンチューブ中の残留硬化物の長さが長い程、光や熱の届き難い深部でもラジカル重合反応が進行していることとなり、一定量の光又は熱エネルギーでより高感度に硬化反応を起こすことができるということとなる。よって、表1又は表2に前記テフロンチューブ中の残留硬化物の長さを示し、硬化性の指標とした。
比較例1〜6は既存の(メタ)アクリレートを用いており、高感度化されていないため、30mm以上より深部では硬化が十分で無く、照射した光又は熱エネルギーではラジカル重合反応が十分に起こっていない事を示している。これに対し、実施例1〜28の本発明品の(メタ)アクリレートを用いた組成物では、比較例の組成よりも残留硬化物の長さが明らかに伸びており、従来の光又は熱硬化材料では硬化させることができなかった光や熱の届き難い深部においてもラジカル重合反応による硬化を達成しており、硬化材料が高感度化されていることが確認された。これはすなわち低エネルギーで、複雑な形状や厚みのある形状に硬化材料を硬化させる事が可能であることを意味するものである。
表3に示す各成分を、それぞれの表に示す組成(質量部)で、攪拌機を用いて混合し溶解又は分散させ、実施例29、30比較例7、8に示される硬化材料を得た。比較例は、重合物を用いた連鎖移動剤(UP−1:合成例7)を用いて調製した硬化材料を用いた。それぞれの材料は調製直後に目視で濁度を観察し、25℃における粘度を回転粘度計によって測定した。その後、0.5mm厚の8号ダンベル片形状に硬化させて、20mm/miNでの引張り試験を行って、その破断伸び(%)を測定した。表3に濁度、粘度、破断伸びの測定結果を示した。
攪拌機を備えた反応容器に、数平均分子量が400のポリプロピレングリコール80g(200mmol)、ヘキサメチレンジイソシアネート40g(238mmol)とジブチルスズジラウレート0.05gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT−IRを測定して2300cm−1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。FT−IRの吸収面積から残留イソシアネート基の含有量を計算し、反応前と比較して約15%まで減少して変化が無くなった時を反応終了とし、無色透明粘調性液体を得た。次にこの粘調性液体100g(33mmol)と2−ヒドロキシエチルアクリレート8.2g(70.6mmol)、ペンタエリトリトールテトラキス[3−(3,5−ジ−teRt−ブチル−4−ヒドロキシフェニル)プロピオナート]0.02gを仕込み、攪拌しながら液温度を室温から50℃まで1時間かけて上げた。その後少量をサンプリングしFT−IRを測定して2300cm−1付近のイソシアネートの吸収を確認しながら、50℃にて攪拌を続けた。FT−IRの吸収面積から残留イソシアネート基の含有量見積り、その吸収が消失した時を反応終了とし、無色透明粘調性液体を得た。これをUP−1とする。UP−1は数分子量約3200、末端がアクリレート基の含ウレタン結合化合物である。
比較例7、8は重合物である連鎖移動剤を用いているため、他の成分と相溶性が十分でなく、目視においても微濁を呈してした。また硬化材料の粘度は5Pa・S以上であった。また、破断伸びは200%以下であり、実施例29、30と比較すると低い値であった。これは前述の様に重合物である連鎖移動剤と他の成分との相溶性が十分でないためと推定される。これに対し、実施例29、30の本発明品の(メタ)アクリレートを用いた組成物は澄明で十分な相溶性を持ち、破断伸びも300%以上と良好であった。粘度も1Pa・S以下であり、低粘度仕様の硬化材料作成が可能であった。
Claims (6)
- 前記、式2または式3構造のモル含有量(官能基・結合基mol/(メタ)アクリレートの質量)が0.001mol/g以上であることを特徴とする(メタ)アクリレート。
- 請求項1又は2記載の(メタ)アクリレートを含んでいることを特徴とするラジカル硬化材料。
- 含金属化合物を含んでいる事を特徴とする請求項3記載のラジカル硬化材料。
- 前記含金属化合物が、スズ、銅、亜鉛、コバルト、ニッケルから選択される少なくとも1種の金属を含むことを特徴とする請求項4記載のラジカル硬化材料。
- 前記式1中のR4が、C1〜C18の直鎖状アルキル基、分岐状アルキル基、環状アルキル鎖、又はその誘導体のいずれかであることを特徴とする請求項3〜5のいずれか1項に記載のラジカル硬化材料。
Priority Applications (5)
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CN109206550B (zh) * | 2017-06-30 | 2022-09-09 | 厦门天策材料科技有限公司 | 一种杂化超分子作用动态聚合物 |
CN109207110B (zh) * | 2017-06-30 | 2022-08-12 | 厦门天策材料科技有限公司 | 一种杂化交联动态聚合物 |
CN107699040A (zh) * | 2017-10-17 | 2018-02-16 | 浙江浦江永进工贸有限公司 | 一种聚氨酯型油墨的制备方法 |
CN108948285B (zh) * | 2018-06-19 | 2021-10-22 | 武汉源锦建材科技有限公司 | 一种高减水高保坍型聚羧酸减水剂及其制备方法 |
CN111056976A (zh) * | 2019-12-31 | 2020-04-24 | 海聚高分子材料科技(广州)有限公司 | 一种氨基甲酸酯多(甲基)丙烯酸酯及其制备方法和应用 |
CN111393567A (zh) * | 2020-04-22 | 2020-07-10 | 珠海赛纳三维科技有限公司 | 一种三维成型材料及其制备方法和应用 |
CN113201087B (zh) * | 2020-11-20 | 2022-08-19 | 联固新材料科技(广州)有限公司 | 羟基丙烯酸分散体及其制备方法和双组分聚氨酯漆 |
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EP2960230A1 (en) | 2015-12-30 |
EP2960230A4 (en) | 2015-12-30 |
WO2014128992A1 (ja) | 2014-08-28 |
US9708432B2 (en) | 2017-07-18 |
JP6088287B2 (ja) | 2017-03-01 |
CN105008326B (zh) | 2018-09-11 |
CN105008326A (zh) | 2015-10-28 |
US20160017071A1 (en) | 2016-01-21 |
EP2960230B1 (en) | 2020-05-06 |
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