JP2009074070A5 - - Google Patents

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Publication number: JP2009074070A5
Authority: JP; Japan
Prior art keywords: group; radiation curable; optionally; groups; compound
Prior art date: 2008-08-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP2008215332A

Other languages

English (en)

Japanese (ja)

Other versions

JP5591457B2 (ja

JP2009074070A (ja

Filing date

2008-08-25

Publication date

2011-10-06

2007-08-25 Priority claimed from DE200710040240 external-priority patent/DE102007040240A1/de

2008-08-25 Application filed filed Critical

2009-04-09 Publication of JP2009074070A publication Critical patent/JP2009074070A/ja

2011-10-06 Publication of JP2009074070A5 publication Critical patent/JP2009074070A5/ja

2014-09-17 Application granted granted Critical

2014-09-17 Publication of JP5591457B2 publication Critical patent/JP5591457B2/ja

Status Expired - Fee Related legal-status Critical Current

2028-08-25 Anticipated expiration legal-status Critical

Links

230000005855 radiation Effects 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 13
238000000576 coating method Methods 0.000 claims description 12
239000011248 coating agent Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 4
238000006116 polymerization reaction Methods 0.000 claims description 4
239000000463 material Substances 0.000 claims description 3
239000003973 paint Substances 0.000 claims description 3
229920001228 polyisocyanate Polymers 0.000 claims description 3
239000005056 polyisocyanate Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 2
239000008199 coating composition Substances 0.000 claims description 2
238000009472 formulation Methods 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000003999 initiator Substances 0.000 claims description 2
239000000976 ink Substances 0.000 claims description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 2
150000003512 tertiary amines Chemical class 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
239000000853 adhesive Substances 0.000 claims 1
230000001070 adhesive effect Effects 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
238000005266 casting Methods 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000000805 composite resin Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
239000000178 monomer Substances 0.000 claims 1
229920002120 photoresistant polymer Polymers 0.000 claims 1
230000009257 reactivity Effects 0.000 claims 1
239000011347 resin Substances 0.000 claims 1
229920005989 resin Polymers 0.000 claims 1
239000000565 sealant Substances 0.000 claims 1
238000004513 sizing Methods 0.000 claims 1
239000000758 substrate Substances 0.000 claims 1
CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
238000001723 curing Methods 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
-1 polybutylene Polymers 0.000 description 4
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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 2
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
239000004146 Propane-1,2-diol Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
239000004417 polycarbonate Substances 0.000 description 2
229920000515 polycarbonate Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
229960004063 propylene glycol Drugs 0.000 description 2
235000013772 propylene glycol Nutrition 0.000 description 2
IUYYVMKHUXDWEU-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,1-diol Chemical compound CC(C)CC(C)(C)C(O)O IUYYVMKHUXDWEU-UHFFFAOYSA-N 0.000 description 1
WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
IUGOPULVANEDRX-UHFFFAOYSA-N 2-ethylhexane-1,1-diol Chemical compound CCCCC(CC)C(O)O IUGOPULVANEDRX-UHFFFAOYSA-N 0.000 description 1
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
238000003848 UV Light-Curing Methods 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
FGUUNXDRMVKHCF-UHFFFAOYSA-N bis(hydroxymethyl)tricyclo[5.2.1.0(2,6)]decane Chemical compound C12CCCC2(CO)C2(CO)CC1CC2 FGUUNXDRMVKHCF-UHFFFAOYSA-N 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229940051250 hexylene glycol Drugs 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000009434 installation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

JP2008215332A 2007-08-25 2008-08-25 低粘性の化学線硬化性基含有アロファネートの製造方法 Expired - Fee Related JP5591457B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE102007040240.8		2007-08-25
DE200710040240 DE102007040240A1 (de)	2007-08-25	2007-08-25	Verfahren zur Herstellung von niedrigviskosen Allophanaten mit aktinisch härtbaren Gruppen

Publications (3)

Publication Number	Publication Date
JP2009074070A JP2009074070A (ja)	2009-04-09
JP2009074070A5 true JP2009074070A5 (2)	2011-10-06
JP5591457B2 JP5591457B2 (ja)	2014-09-17

Family

ID=40039714

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2008215332A Expired - Fee Related JP5591457B2 (ja)	2007-08-25	2008-08-25	低粘性の化学線硬化性基含有アロファネートの製造方法

Country Status (13)

Country	Link
US (1)	US8071659B2 (2)
EP (1)	EP2031005B1 (2)
JP (1)	JP5591457B2 (2)
KR (2)	KR101504356B1 (2)
CN (1)	CN101372528B (2)
AT (1)	ATE496953T1 (2)
AU (1)	AU2008203814B2 (2)
BR (1)	BRPI0803675A2 (2)
CA (1)	CA2639063C (2)
DE (2)	DE102007040240A1 (2)
ES (1)	ES2358301T3 (2)
PL (1)	PL2031005T3 (2)
TW (1)	TWI433861B (2)

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DE102004048873A1 (de) *	2004-10-07	2006-04-13	Bayer Materialscience Ag	Verfahren zur Herstellung von niedrigviskosen Allophanaten mit aktinisch härtbaren Gruppen
DE102009008569A1 (de)	2009-02-12	2010-08-19	Bayer Materialscience Ag	Verfahren zur Herstellung von besonders reaktiven und niedrigviskosen Allophanaten mit aktinisch härtbaren Gruppen und deren Verwendung zur Herstellung besonders kratzfester Beschichtungen
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US9023916B2 (en)	2010-09-30	2015-05-05	Voco Gmbh	Composite material comprising a monomer with a polyalicyclic structure element
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US9079828B2 (en)	2010-09-30	2015-07-14	Voco Gmbh	Polymerizable compounds comprising a polyalicylic structure element
EP2436364B1 (de)	2010-09-30	2017-05-31	VOCO GmbH	Lackzusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement
EP2436363B1 (de)	2010-09-30	2017-01-18	VOCO GmbH	Zusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement zum Füllen und/oder Versiegeln eines Wurzelkanals
EP2726525B1 (en)	2011-06-30	2020-12-30	Dow Global Technologies LLC	Improved process for making low viscosity, fast curing silane terminated polymers
ES2523277T3 (es) *	2011-10-14	2014-11-24	Allnex Ip S.À.R.L.	Procedimiento para la preparación de alofanatos emulsionables en agua, de baja viscosidad, que contienen grupos endurecibles por radiaciones
EP2581397B1 (de)	2011-10-14	2014-12-10	Allnex IP S.à.r.l.	Verfahren zur herstellung von niedrigviskosen, wasserverdünnbaren urethan(meth)acrylaten
FR3003255B1 (fr)	2013-03-14	2015-10-02	Vencorex France	Allophanate polyacrylate
JP6281188B2 (ja) *	2013-03-28	2018-02-21	日油株式会社	ウレタン（メタ）アクリレート及びこれを含有する光硬化型樹脂組成物
US20160168397A1 (en) *	2013-07-17	2016-06-16	Jun Liu	Substrate coating compositions and methods
JP6241727B2 (ja) *	2013-10-31	2017-12-06	日油株式会社	ウレタン（メタ）アクリレート組成物
BR112016029755A2 (pt)	2014-06-23	2017-08-22	Carbon Inc	métodos de produção de objetos tridimensionais a partir de materiais tendo múltiplos mecanismos de endurecimento
US10316213B1 (en)	2017-05-01	2019-06-11	Formlabs, Inc.	Dual-cure resins and related methods
EP3424971A1 (de) *	2017-07-03	2019-01-09	HILTI Aktiengesellschaft	Urethanmethacrylat-verbindungen enthaltende reaktivharze, reaktivharzkomponenten sowie reaktivharz-systeme und deren verwendung
WO2025192236A1 (ja) *	2024-03-14	2025-09-18	三井化学株式会社	（メタ）アクリレート化合物の製造方法

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US6150476A (en) *	1998-12-23	2000-11-21	Bayer Corporation	Coating compositions containing a mixture of ethylenically unsaturated polyurethanes
JP4678466B2 (ja) *	2001-08-09	2011-04-27	Ｄｉｃ株式会社	エネルギー線硬化型樹脂組成物
DE10205608A1 (de)	2002-02-11	2003-08-21	Degussa	Bei niedriger Temperatur härtbare feste uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen
DE10246512A1 (de)	2002-10-04	2004-04-15	Bayer Ag	Niedrigviskose strahlenhärtende und thermisch härtende Polyisocyanate
DE102004012903A1 (de) *	2004-03-17	2005-10-06	Bayer Materialscience Ag	Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
DE102004043538A1 (de) *	2004-09-09	2006-03-16	Bayer Materialscience Ag	Herstellung von neuen strahlenhärtenden Bindemitteln
DE102004043539A1 (de) *	2004-09-09	2006-03-30	Bayer Materialscience Ag	Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
DE102004043540A1 (de) *	2004-09-09	2006-03-30	Bayer Materialscience Ag	Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
JP2006083273A (ja) *	2004-09-15	2006-03-30	Mitsui Chemicals Inc	アロファネート基含有（メタ）アクリレート樹脂組成物
DE102004048873A1 (de)	2004-10-07	2006-04-13	Bayer Materialscience Ag	Verfahren zur Herstellung von niedrigviskosen Allophanaten mit aktinisch härtbaren Gruppen
US20060128923A1 (en) *	2004-12-15	2006-06-15	Bayer Materialscience Llc	Radiation curable compositions
DE102005011231A1 (de) *	2005-03-11	2006-09-14	Bayer Materialscience Ag	Spezielle Allophanate enthaltende, modifizierte Polyurethane

2007
- 2007-08-25 DE DE200710040240 patent/DE102007040240A1/de not_active Withdrawn
2008
- 2008-08-09 EP EP20080014258 patent/EP2031005B1/de active Active
- 2008-08-09 ES ES08014258T patent/ES2358301T3/es active Active
- 2008-08-09 PL PL08014258T patent/PL2031005T3/pl unknown
- 2008-08-09 DE DE200850002449 patent/DE502008002449D1/de active Active
- 2008-08-09 AT AT08014258T patent/ATE496953T1/de active
- 2008-08-11 AU AU2008203814A patent/AU2008203814B2/en not_active Ceased
- 2008-08-20 US US12/229,185 patent/US8071659B2/en active Active
- 2008-08-22 BR BRPI0803675-6A patent/BRPI0803675A2/pt not_active IP Right Cessation
- 2008-08-22 KR KR1020080082280A patent/KR101504356B1/ko active Active
- 2008-08-22 CA CA2639063A patent/CA2639063C/en not_active Expired - Fee Related
- 2008-08-22 TW TW97132005A patent/TWI433861B/zh active
- 2008-08-25 CN CN2008101463255A patent/CN101372528B/zh active Active
- 2008-08-25 JP JP2008215332A patent/JP5591457B2/ja not_active Expired - Fee Related
2014
- 2014-11-18 KR KR20140161197A patent/KR20140143733A/ko not_active Ceased

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JP2009074070A5 (2)	2011-10-06
JP2009062533A5 (2)	2011-10-06
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