RU2346016C2 - Отверждение покрытий, индуцированное плазмой - Google Patents
Отверждение покрытий, индуцированное плазмой Download PDFInfo
- Publication number
- RU2346016C2 RU2346016C2 RU2004133886/04A RU2004133886A RU2346016C2 RU 2346016 C2 RU2346016 C2 RU 2346016C2 RU 2004133886/04 A RU2004133886/04 A RU 2004133886/04A RU 2004133886 A RU2004133886 A RU 2004133886A RU 2346016 C2 RU2346016 C2 RU 2346016C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- phenyl
- compound
- composition
- hydrogen atom
- Prior art date
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- 238000000576 coating method Methods 0.000 title claims abstract description 128
- 239000011248 coating agent Substances 0.000 title claims abstract description 86
- 230000008023 solidification Effects 0.000 title abstract 4
- 238000007711 solidification Methods 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 claims abstract description 188
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- 238000000034 method Methods 0.000 claims abstract description 84
- 239000000758 substrate Substances 0.000 claims abstract description 50
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- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000003254 radicals Chemical class 0.000 claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 17
- 239000002131 composite material Substances 0.000 claims abstract description 8
- 239000012949 free radical photoinitiator Substances 0.000 claims abstract description 7
- 150000001768 cations Chemical class 0.000 claims abstract description 6
- -1 siloxane radical Chemical class 0.000 claims description 228
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 27
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- 125000005843 halogen group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
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- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 239000004593 Epoxy Chemical group 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 19
- 239000000049 pigment Substances 0.000 claims description 18
- 230000009471 action Effects 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 150000002170 ethers Chemical class 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 229920000877 Melamine resin Polymers 0.000 claims description 13
- 238000007639 printing Methods 0.000 claims description 13
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000004611 light stabiliser Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 239000000975 dye Substances 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 150000008064 anhydrides Chemical class 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 238000010526 radical polymerization reaction Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 claims description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 6
- 150000008366 benzophenones Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 150000008062 acetophenones Chemical class 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 150000007974 melamines Chemical class 0.000 claims description 4
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 238000002203 pretreatment Methods 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
- FNDFKMXAOATGJU-UHFFFAOYSA-N 1-phenyl-2-sulfonylethanone Chemical class O=S(=O)=CC(=O)C1=CC=CC=C1 FNDFKMXAOATGJU-UHFFFAOYSA-N 0.000 claims description 2
- MXFOQZLUCVHVRD-UHFFFAOYSA-N 2-methylsulfonyloxyethyl-[2,3,4,5-tetrahydroxy-6-(2-methylsulfonyloxyethylamino)hexyl]azanium;chloride Chemical compound [Cl-].CS(=O)(=O)OCCNCC(O)C(O)C(O)C(O)C[NH2+]CCOS(C)(=O)=O MXFOQZLUCVHVRD-UHFFFAOYSA-N 0.000 claims description 2
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- 229910015892 BF 4 Inorganic materials 0.000 claims description 2
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 2
- 229910021115 PF 6 Inorganic materials 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 2
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- 125000006331 halo benzoyl group Chemical group 0.000 claims description 2
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- 230000001235 sensitizing effect Effects 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical compound C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 claims 2
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/14—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by electrical means
- B05D3/141—Plasma treatment
- B05D3/145—After-treatment
- B05D3/147—Curing
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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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/52—Polymerisation initiated by wave energy or particle radiation by electric discharge, e.g. voltolisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/14—Chemical modification with acids, their salts or anhydrides
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Polyurethanes Or Polyureas (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coating By Spraying Or Casting (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
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| EP02008254 | 2002-04-19 | ||
| EP02008254.1 | 2002-04-19 |
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| EP (1) | EP1497338B1 (enExample) |
| JP (1) | JP5073155B2 (enExample) |
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| BR (1) | BR0309389B1 (enExample) |
| CA (1) | CA2482470C (enExample) |
| DE (1) | DE60333991D1 (enExample) |
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| RU2543878C2 (ru) * | 2009-03-05 | 2015-03-10 | Акцо Нобель Коатингс Интернэшнл Б.В. | Гидроксилфункциональные полиолы на основе масла и композиции для нанесения покрытия, полученные из гидроксилфункциональных полиолов на основе масла |
| RU2615406C2 (ru) * | 2011-04-27 | 2017-04-04 | СиПиФИЛМЗ ИНК. | Атмосферостойкий композит внешней пленки |
| US10647876B2 (en) | 2011-10-07 | 2020-05-12 | Allnex Netherlands B.V. | Crosslinkable composition cross-linkable by real Michael addition reaction and resins for use in said composition |
| US10604622B2 (en) | 2013-04-08 | 2020-03-31 | Allnex Netherlands B.V. | Composition crosslinkable by Real Michael Addition (RMA) reaction |
| RU2629295C2 (ru) * | 2013-04-10 | 2017-08-28 | Вэлспар Сорсинг, Инк | Покрытие, устойчивое к высокосернистому газу |
| RU2675555C2 (ru) * | 2013-11-05 | 2018-12-19 | Констракшн Рисёрч Энд Текнолоджи Гмбх | Новые системы связывающих агентов |
| US10767074B2 (en) | 2015-04-17 | 2020-09-08 | Allnex Netherlands B.V. | Process for the manufacture of a crosslinkable composition |
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| RU2721703C2 (ru) * | 2015-04-17 | 2020-05-21 | Аллнекс Незерландс Б.В. | Rma-сшиваемые композиции и rma-сшиваемые смолы для получения покрытий, легко поддающихся очистке |
| US10920101B2 (en) | 2015-04-17 | 2021-02-16 | Allnex Netherlands B.V. | RMA crosslinkable compositions and RMA crosslinkable resins for easy to clean coatings |
| US11072724B2 (en) | 2015-04-17 | 2021-07-27 | Allnex Netherlands B.V. | Adhesion promotor for real michael addition crosslinkable compositions |
| US11414565B2 (en) | 2015-04-17 | 2022-08-16 | Allnex Netherlands B.V. | Process for the manufacture of a crosslinkable composition |
| US11674055B2 (en) | 2015-04-17 | 2023-06-13 | Allnex Netherlands B.V. | RMA crosslinkable compositions and RMA crosslinkable resins for easy to clean coatings |
| US11674054B2 (en) | 2015-04-17 | 2023-06-13 | Allnex Netherlands B.V. | Method for curing a RMA crosslinkable resin coating, RMA crosslinkable compositions and resins for use therein |
| US11713402B2 (en) | 2015-04-17 | 2023-08-01 | Allnex Netherlands B.V. | RMA crosslinkable compositions and RMA crosslinkable resins for easy to clean coatings |
| US11814536B2 (en) | 2015-04-17 | 2023-11-14 | Allnex Netherlands B.V. | Floor coating compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003227644A1 (en) | 2003-11-03 |
| CA2482470C (en) | 2011-06-07 |
| AU2003227644B2 (en) | 2008-08-21 |
| BR0309389B1 (pt) | 2014-04-22 |
| US8003169B2 (en) | 2011-08-23 |
| ZA200407710B (en) | 2006-06-28 |
| EP1497338A2 (en) | 2005-01-19 |
| WO2003089479A2 (en) | 2003-10-30 |
| JP2005523803A (ja) | 2005-08-11 |
| KR100996585B1 (ko) | 2010-11-25 |
| CN1646572A (zh) | 2005-07-27 |
| EP1497338B1 (en) | 2010-09-01 |
| PL207529B1 (pl) | 2010-12-31 |
| MXPA04009790A (es) | 2004-12-13 |
| US20050129859A1 (en) | 2005-06-16 |
| ATE479713T1 (de) | 2010-09-15 |
| RU2004133886A (ru) | 2005-08-10 |
| DE60333991D1 (de) | 2010-10-14 |
| KR20040103960A (ko) | 2004-12-09 |
| WO2003089479A3 (en) | 2004-09-16 |
| BR0309389A (pt) | 2005-04-19 |
| PL371730A1 (en) | 2005-06-27 |
| CN100482694C (zh) | 2009-04-29 |
| JP5073155B2 (ja) | 2012-11-14 |
| CA2482470A1 (en) | 2003-10-30 |
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