CA2930343C - Method for curing an adhesive using microwave irradiation - Google Patents
Method for curing an adhesive using microwave irradiation Download PDFInfo
- Publication number
- CA2930343C CA2930343C CA2930343A CA2930343A CA2930343C CA 2930343 C CA2930343 C CA 2930343C CA 2930343 A CA2930343 A CA 2930343A CA 2930343 A CA2930343 A CA 2930343A CA 2930343 C CA2930343 C CA 2930343C
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- Prior art keywords
- alkyl
- cycloalkyl
- aryl
- residues
- independently
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 75
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000002608 ionic liquid Substances 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 150000001450 anions Chemical class 0.000 claims abstract description 15
- 150000001768 cations Chemical class 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 10
- -1 sulfonium cation Chemical class 0.000 claims description 217
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 63
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 27
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- 125000005843 halogen group Chemical group 0.000 claims description 26
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 22
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- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
- 229920002554 vinyl polymer Polymers 0.000 claims description 20
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 19
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 19
- 229920000877 Melamine resin Polymers 0.000 claims description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 19
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- 239000000463 material Substances 0.000 claims description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 6
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- 238000002844 melting Methods 0.000 claims description 6
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
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- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 claims description 5
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- 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 claims description 4
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- BXYHVFRRNNWPMB-UHFFFAOYSA-N tetramethylphosphanium Chemical compound C[P+](C)(C)C BXYHVFRRNNWPMB-UHFFFAOYSA-N 0.000 description 1
- CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052613 tourmaline Inorganic materials 0.000 description 1
- 239000011032 tourmaline Substances 0.000 description 1
- 229940070527 tourmaline Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- HOMONHWYLOPSLL-UHFFFAOYSA-N tributyl(ethyl)phosphanium Chemical compound CCCC[P+](CC)(CCCC)CCCC HOMONHWYLOPSLL-UHFFFAOYSA-N 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-O tributylphosphanium Chemical compound CCCC[PH+](CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-O 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- TZWFFXFQARPFJN-UHFFFAOYSA-N triethyl(methyl)phosphanium Chemical compound CC[P+](C)(CC)CC TZWFFXFQARPFJN-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-O triethylphosphanium Chemical compound CC[PH+](CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-O 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-O trioctylazanium Chemical compound CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-O 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-O tripropylphosphanium Chemical compound CCC[PH+](CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-O 0.000 description 1
- FVJLCPJDDAGIJE-UHFFFAOYSA-N tris(2-hydroxyethyl)-methylazanium Chemical compound OCC[N+](C)(CCO)CCO FVJLCPJDDAGIJE-UHFFFAOYSA-N 0.000 description 1
- OZHHAAKCLPQJDD-UHFFFAOYSA-N tris(2-methoxyethyl)-methylazanium Chemical compound COCC[N+](C)(CCOC)CCOC OZHHAAKCLPQJDD-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13195017 | 2013-11-29 | ||
| EP13195017.2 | 2013-11-29 | ||
| PCT/EP2014/075968 WO2015079028A1 (de) | 2013-11-29 | 2014-11-28 | Verrfahren zum aushärten eines klebstoffs mittels mikrowellenbestrahlung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2930343A1 CA2930343A1 (en) | 2015-06-04 |
| CA2930343C true CA2930343C (en) | 2021-06-08 |
Family
ID=49679401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2930343A Active CA2930343C (en) | 2013-11-29 | 2014-11-28 | Method for curing an adhesive using microwave irradiation |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20170015871A1 (en:Method) |
| EP (2) | EP3527639B1 (en:Method) |
| JP (1) | JP6483124B2 (en:Method) |
| KR (1) | KR102339016B1 (en:Method) |
| CN (1) | CN106029804B (en:Method) |
| BR (1) | BR112016011663B1 (en:Method) |
| CA (1) | CA2930343C (en:Method) |
| ES (1) | ES2906062T3 (en:Method) |
| PL (1) | PL3527639T3 (en:Method) |
| RU (1) | RU2680070C1 (en:Method) |
| WO (1) | WO2015079028A1 (en:Method) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2980797A1 (en) | 2014-07-28 | 2016-02-03 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Audio decoder, method and computer program using a zero-input-response to obtain a smooth transition |
| MX376824B (es) | 2015-10-14 | 2025-03-07 | Bristol Myers Squibb Co | 2,4-dihidroxi-nicotinamidas como agonistas del recepor de apelina (apj). |
| JP6948322B2 (ja) | 2015-12-16 | 2021-10-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | Ａｐｊ受容体のａｐｊアゴニストとしてのヘテロアリールヒドロキシピリミジノン |
| AU2017238504B2 (en) | 2016-03-24 | 2021-05-27 | Bristol-Myers Squibb Company | 6-hydroxy-4-oxo-1,4-dihydropyrimidine-5-carboxamides as APJ agonists |
| JP6974823B2 (ja) * | 2016-05-31 | 2021-12-01 | 国立大学法人神戸大学 | マイクロ波解体用接着組成物、及び、接着物の解体方法 |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| HRP20192165T4 (hr) | 2016-09-21 | 2025-07-18 | Celanese International Corporation | Acesulfam-kalij-pripravci i postupci njihove proizvodnje |
| CN118459423A (zh) | 2016-09-21 | 2024-08-09 | 国际人造丝公司 | 乙酰舒泛钾组合物和用于生产其的方法 |
| PT3319948T (pt) | 2016-09-21 | 2021-09-13 | Celanese Int Corp | Composições de acessulfame de potássio e processos para produzir as mesmas |
| HRP20201619T4 (hr) | 2016-09-21 | 2025-03-28 | Celanese International Corporation | Pripravci kalijevog acesulfama i postupci za njegovu proizvodnju |
| DE102016222088A1 (de) * | 2016-11-10 | 2018-05-17 | Robert Bosch Gmbh | Fügeverfahren zur Herstellung einer Batterie sowie Batterie |
| RS62899B1 (sr) | 2017-01-23 | 2022-03-31 | Cadent Therapeutics Inc | Modulatori kalijumovih kanala |
| JP6857625B2 (ja) * | 2017-02-28 | 2021-04-14 | 積水化成品工業株式会社 | 発熱性ポリマー、発熱剤、及び発熱性ポリマーによる発熱を用いた各種方法 |
| KR102037335B1 (ko) * | 2017-10-31 | 2019-10-29 | 한국과학기술원 | 개시제를 이용한 화학 기상 증착법을 이용한 고분자 감압 접착제의 제조방법 |
| CN108570019B (zh) * | 2018-05-31 | 2021-02-26 | 大连理工大学 | 一类酸性离子液体及其催化应用 |
| US11993586B2 (en) | 2018-10-22 | 2024-05-28 | Novartis Ag | Crystalline forms of potassium channel modulators |
| JP7543659B2 (ja) * | 2020-03-03 | 2024-09-03 | 日清紡ホールディングス株式会社 | イオン液体を用いた平滑材料の固定方法 |
| KR102698413B1 (ko) | 2020-05-05 | 2024-08-26 | 뉴베일런트, 아이엔씨. | 헤테로방향족 거대환식 에터 화학치료제 |
| DE102020126608A1 (de) | 2020-10-09 | 2022-04-14 | Woco Industrietechnik Gmbh | Verbindungsmasse zum stoffschlüssigen Verbinden von Kunststoffbauteilen, Bausatz zum Herstellen eines Kunststoffteils und dessen Verwendung, Verfahren zum Herstellen eines Kunststoffteils und Verfahren zum Verbinden von Kunststoffbauteilen sowie Kraftfahrzeugbauteil |
| CN114709068B (zh) * | 2022-06-07 | 2022-09-02 | 四川大学 | 微波场电场磁场耦合提升锰锌铁氧体磁性能的装置及方法 |
| CN116285829B (zh) * | 2023-04-04 | 2025-04-25 | 陕西师范大学 | 同时耐超低温与有机溶剂的组合类超分子粘合剂 |
| CN116589962B (zh) * | 2023-05-18 | 2025-11-25 | 陕西师范大学 | 耐受极端条件的离子型可逆粘合剂及其合成方法和双组份超分子粘合剂 |
| WO2026008460A1 (en) | 2024-07-03 | 2026-01-08 | Heiq Materials Ag | Method for the production of ionic liquids |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3802881A1 (de) * | 1987-11-16 | 1989-05-24 | Utz Ag Georg | Mikrowellenaktivierbarer schmelzklebstoff |
| JP3742099B2 (ja) * | 1991-07-03 | 2006-02-01 | スリーエム カンパニー | マイクロ波活性化性接着物品及びその利用方法 |
| US5120176A (en) | 1991-07-29 | 1992-06-09 | Dennison Manufacturing Company | Fabrication of bound documents |
| US6103812A (en) | 1997-11-06 | 2000-08-15 | Lambda Technologies, Inc. | Microwave curable adhesive |
| AU774290B2 (en) | 1999-05-26 | 2004-06-24 | Personal Chemistry I Uppsala Ab | Preparation and use of ionic liquids in microwave-assisted chemical transformations |
| EP1228158B1 (de) | 1999-08-24 | 2008-07-30 | Henkel AG & Co. KGaA | Verklebung durch Klebstoffe enthaltend nanoskalige Teilchen |
| DK1472009T3 (da) * | 2002-01-29 | 2006-04-10 | Ciba Sc Holding Ag | Fremgangsmåde til fremstilling af stærkt hæftende belægninger |
| DE10229595A1 (de) | 2002-07-02 | 2004-01-15 | Bayer Cropscience Ag | Phenylbenzamide |
| CA2491587A1 (en) | 2002-07-05 | 2004-01-15 | Creavis Gesellschaft Fuer Technologie Und Innovation Mbh | Polymeric compositions containing polymers and ionic liquids |
| TW200617124A (en) * | 2004-06-01 | 2006-06-01 | Nitto Denko Corp | Pressure-sensitive adhesive composition, pressure-sensitive adhesive sheet and surface protecting film |
| WO2008071768A2 (de) * | 2006-12-15 | 2008-06-19 | Basf Se | Verfahren zum trennen verbundener substrate durch mikrowellenbestrahlung |
| JP2009149828A (ja) * | 2007-12-25 | 2009-07-09 | Sanyo Chem Ind Ltd | マイクロ波硬化性組成物 |
| JP2009167362A (ja) * | 2008-01-21 | 2009-07-30 | Sanyo Chem Ind Ltd | マイクロ波重合性組成物 |
| JP2009227949A (ja) * | 2008-02-28 | 2009-10-08 | Sanyo Chem Ind Ltd | マイクロ波硬化性組成物 |
| CA2763967C (en) * | 2009-06-08 | 2017-08-15 | Basf Se | Use of ionic liquids for the pretreatment of surfaces of plastics for metallization |
| CN102781921B (zh) * | 2009-08-28 | 2015-08-12 | 3M创新有限公司 | 包含可聚合离子液体混合物的组合物和制品及固化方法 |
-
2014
- 2014-11-28 JP JP2016535153A patent/JP6483124B2/ja active Active
- 2014-11-28 EP EP19160845.4A patent/EP3527639B1/de active Active
- 2014-11-28 CA CA2930343A patent/CA2930343C/en active Active
- 2014-11-28 EP EP14805585.8A patent/EP2997106B1/de not_active Not-in-force
- 2014-11-28 US US15/039,129 patent/US20170015871A1/en not_active Abandoned
- 2014-11-28 PL PL19160845T patent/PL3527639T3/pl unknown
- 2014-11-28 RU RU2016125758A patent/RU2680070C1/ru active
- 2014-11-28 BR BR112016011663-1A patent/BR112016011663B1/pt active IP Right Grant
- 2014-11-28 KR KR1020167014782A patent/KR102339016B1/ko active Active
- 2014-11-28 ES ES19160845T patent/ES2906062T3/es active Active
- 2014-11-28 CN CN201480065308.2A patent/CN106029804B/zh active Active
- 2014-11-28 WO PCT/EP2014/075968 patent/WO2015079028A1/de not_active Ceased
-
2019
- 2019-02-04 US US16/266,944 patent/US11084954B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR102339016B1 (ko) | 2021-12-14 |
| EP3527639A1 (de) | 2019-08-21 |
| BR112016011663B1 (pt) | 2022-02-22 |
| RU2680070C1 (ru) | 2019-02-14 |
| RU2016125758A (ru) | 2018-01-09 |
| BR112016011663A2 (en:Method) | 2017-08-08 |
| ES2906062T3 (es) | 2022-04-13 |
| PL3527639T3 (pl) | 2022-03-07 |
| CA2930343A1 (en) | 2015-06-04 |
| KR20160113097A (ko) | 2016-09-28 |
| JP2017504677A (ja) | 2017-02-09 |
| CN106029804B (zh) | 2019-09-24 |
| US20190169469A1 (en) | 2019-06-06 |
| US11084954B2 (en) | 2021-08-10 |
| WO2015079028A1 (de) | 2015-06-04 |
| JP6483124B2 (ja) | 2019-03-13 |
| EP3527639B1 (de) | 2021-09-08 |
| CN106029804A (zh) | 2016-10-12 |
| EP2997106A1 (de) | 2016-03-23 |
| US20170015871A1 (en) | 2017-01-19 |
| EP2997106B1 (de) | 2019-03-06 |
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| EEER | Examination request |
Effective date: 20190627 |