ES2998060T3 - Photopolymerizable compositions including a urethane component and a reactive diluent, orthodontic articles, and methods - Google Patents
Photopolymerizable compositions including a urethane component and a reactive diluent, orthodontic articles, and methods Download PDFInfo
- Publication number
- ES2998060T3 ES2998060T3 ES18839416T ES18839416T ES2998060T3 ES 2998060 T3 ES2998060 T3 ES 2998060T3 ES 18839416 T ES18839416 T ES 18839416T ES 18839416 T ES18839416 T ES 18839416T ES 2998060 T3 ES2998060 T3 ES 2998060T3
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- Spain
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- photopolymerizable composition
- inclusive
- urethane
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- 239000000203 mixture Substances 0.000 title claims abstract description 235
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 136
- 238000000034 method Methods 0.000 title claims abstract description 68
- 239000003085 diluting agent Substances 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 claims abstract description 70
- 239000000654 additive Substances 0.000 claims abstract description 38
- 230000000996 additive effect Effects 0.000 claims abstract description 32
- 239000003112 inhibitor Substances 0.000 claims abstract description 25
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000012360 testing method Methods 0.000 claims description 14
- 238000010146 3D printing Methods 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 229920000233 poly(alkylene oxides) Chemical group 0.000 claims description 4
- 239000004952 Polyamide Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- 238000004949 mass spectrometry Methods 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 229920002647 polyamide Chemical group 0.000 claims description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001281 polyalkylene Chemical group 0.000 claims description 2
- 229920000515 polycarbonate Chemical group 0.000 claims description 2
- 239000004417 polycarbonate Chemical group 0.000 claims description 2
- 229920000728 polyester Chemical group 0.000 claims description 2
- HYQASEVIBPSPMK-UHFFFAOYSA-N 12-(2-methylprop-2-enoyloxy)dodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(C)=C HYQASEVIBPSPMK-UHFFFAOYSA-N 0.000 claims 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims 1
- JSYQTJCNKUAUMM-UHFFFAOYSA-N ethyl carbamate;prop-2-enamide Chemical compound NC(=O)C=C.CCOC(N)=O JSYQTJCNKUAUMM-UHFFFAOYSA-N 0.000 claims 1
- 238000005259 measurement Methods 0.000 abstract description 4
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- 239000000463 material Substances 0.000 description 21
- -1 hydrogen compound Chemical class 0.000 description 20
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 11
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- 239000007788 liquid Substances 0.000 description 10
- 239000000049 pigment Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 238000011417 postcuring Methods 0.000 description 7
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 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 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011960 computer-aided design Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- 238000005516 engineering process Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical class CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
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- 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 2
- 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 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Chemical & Material Sciences (AREA)
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- Macromonomer-Based Addition Polymer (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762536568P | 2017-07-25 | 2017-07-25 | |
| PCT/US2018/042595 WO2019023009A1 (en) | 2017-07-25 | 2018-07-18 | PHOTOPOLYMERIZABLE COMPOSITIONS COMPRISING A URETHANE COMPONENT AND A REACTIVE DILUENT, ARTICLES AND METHODS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2998060T3 true ES2998060T3 (en) | 2025-02-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES18839416T Active ES2998060T3 (en) | 2017-07-25 | 2018-07-18 | Photopolymerizable compositions including a urethane component and a reactive diluent, orthodontic articles, and methods |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11584827B2 (enExample) |
| EP (1) | EP3658602B1 (enExample) |
| JP (2) | JP2020528479A (enExample) |
| KR (1) | KR102673971B1 (enExample) |
| CN (1) | CN110997744B (enExample) |
| BR (1) | BR112020001626A2 (enExample) |
| ES (1) | ES2998060T3 (enExample) |
| WO (1) | WO2019023009A1 (enExample) |
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| BR112018077517A2 (pt) | 2016-06-30 | 2019-04-02 | 3M Innovative Properties Company | composições imprimíveis incluindo componentes altamente viscosos e métodos para criar artigos 3d a partir das mesmas |
| US11602412B2 (en) | 2016-12-23 | 2023-03-14 | 3M Innovative Properties Company | Printable compositions including polymeric and polymerizable components, articles, and methods of making articles therefrom |
| AU2018307762C1 (en) | 2017-07-25 | 2022-02-10 | 3M Innovative Properties Company | Water-resistant polymer-based dental articles |
| CN110997744B (zh) | 2017-07-25 | 2022-06-24 | 3M创新有限公司 | 包含氨基甲酸酯组分和反应性稀释剂的光致聚合型组合物、制品和方法 |
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| CN110997744B (zh) | 2022-06-24 |
| WO2019023009A1 (en) | 2019-01-31 |
| KR20200035264A (ko) | 2020-04-02 |
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