CA2442997C - Solid mixtures of alpha-hydroxycarbonyl derivatives of alpha-methylstyrene oligomers and their use - Google Patents
Solid mixtures of alpha-hydroxycarbonyl derivatives of alpha-methylstyrene oligomers and their use Download PDFInfo
- Publication number
- CA2442997C CA2442997C CA002442997A CA2442997A CA2442997C CA 2442997 C CA2442997 C CA 2442997C CA 002442997 A CA002442997 A CA 002442997A CA 2442997 A CA2442997 A CA 2442997A CA 2442997 C CA2442997 C CA 2442997C
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- mixture
- dimer
- oligomers
- methylstyrene
- Prior art date
- 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.)
- Expired - Fee Related
Links
- 239000008247 solid mixture Substances 0.000 title claims abstract description 31
- 239000000539 dimer Substances 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims description 43
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- -1 hydroxycarbonyl derivatives of alpha-methylstyrene Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000009257 reactivity Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 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 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- 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
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/12—Separation of polymers from solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001VA000011A ITVA20010011A1 (it) | 2001-04-24 | 2001-04-24 | Miscele solide di derivati alfa-idrossicarbonilici di oligomeri dell'alfa-metilstirene e loro uso. |
| ITVA2001A000011 | 2001-04-24 | ||
| PCT/EP2002/003674 WO2002085832A2 (en) | 2001-04-24 | 2002-04-03 | Solid mixtures of alpha-hydroxycarbonyl derivatives of alpha-methylstyrene oligomers and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2442997A1 CA2442997A1 (en) | 2002-10-31 |
| CA2442997C true CA2442997C (en) | 2009-07-07 |
Family
ID=11460852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002442997A Expired - Fee Related CA2442997C (en) | 2001-04-24 | 2002-04-03 | Solid mixtures of alpha-hydroxycarbonyl derivatives of alpha-methylstyrene oligomers and their use |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6995290B2 (enExample) |
| EP (1) | EP1389177B1 (enExample) |
| JP (1) | JP4355497B2 (enExample) |
| KR (1) | KR100877045B1 (enExample) |
| CN (1) | CN1288123C (enExample) |
| AT (1) | ATE410402T1 (enExample) |
| BR (1) | BR0209159A (enExample) |
| CA (1) | CA2442997C (enExample) |
| DE (1) | DE60229234D1 (enExample) |
| ES (1) | ES2314063T3 (enExample) |
| IT (1) | ITVA20010011A1 (enExample) |
| WO (1) | WO2002085832A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004163904A (ja) * | 2002-09-30 | 2004-06-10 | Rohm & Haas Electronic Materials Llc | 改善された光開始剤 |
| JP4589916B2 (ja) * | 2003-05-05 | 2010-12-01 | チバ ホールディング インコーポレーテッド | １−フェニルインダン光開始剤の製造方法 |
| ITVA20060021A1 (it) * | 2006-05-02 | 2007-11-03 | Lamberti Spa | Processo per la preparazione di miscele di derivati alfa-idrossicarbonilici di oligomeri dell'alfa-metilstirene |
| US8507726B2 (en) | 2008-11-03 | 2013-08-13 | Basf Se | Photoinitiator mixtures |
| IT1393223B1 (it) | 2009-03-11 | 2012-04-11 | Lamberti Spa | Procedimento per la preparazione di miscele cristalline di derivati alfa-idrossicarbonilici di dimeri dell'alfa-metilstirene |
| CN102060684B (zh) | 2010-11-12 | 2014-07-16 | 深圳市有为化学技术有限公司 | 对位或间位官能团化芳香酮类化合物、其制备方法及其光聚合引发剂 |
| US20140347429A1 (en) | 2011-12-21 | 2014-11-27 | Sericol Limited | Inks |
| KR102089834B1 (ko) * | 2014-06-10 | 2020-04-24 | 아이지엠 레진스 이탈리아 에스.알.엘. | 페닐인단 화합물의 제조 방법 |
| KR102454846B1 (ko) | 2014-06-10 | 2022-10-13 | 아이지엠 레진스 이탈리아 에스.알.엘. | 페닐인단 광개시제의 제조 방법 |
| CN112698547B (zh) * | 2019-10-23 | 2022-02-22 | 常州强力电子新材料股份有限公司 | 一种光固化组合物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2722264C2 (de) * | 1977-05-17 | 1984-06-28 | Merck Patent Gmbh, 6100 Darmstadt | Verwendung von substituierten Oxyalkylphenonen als Photosensibilisatoren |
| US4987159A (en) * | 1990-04-11 | 1991-01-22 | Fratelli Lamberti S.P.A. | Carbonyl derivatives of 1-phenylindan suitable for use as polymerization photoinitiators, their preparation and use |
-
2001
- 2001-04-24 IT IT2001VA000011A patent/ITVA20010011A1/it unknown
-
2002
- 2002-04-03 JP JP2002583363A patent/JP4355497B2/ja not_active Expired - Lifetime
- 2002-04-03 DE DE60229234T patent/DE60229234D1/de not_active Expired - Lifetime
- 2002-04-03 KR KR1020037013521A patent/KR100877045B1/ko not_active Expired - Fee Related
- 2002-04-03 WO PCT/EP2002/003674 patent/WO2002085832A2/en not_active Ceased
- 2002-04-03 AT AT02735213T patent/ATE410402T1/de not_active IP Right Cessation
- 2002-04-03 CN CNB028085647A patent/CN1288123C/zh not_active Expired - Lifetime
- 2002-04-03 US US10/475,065 patent/US6995290B2/en not_active Expired - Lifetime
- 2002-04-03 ES ES02735213T patent/ES2314063T3/es not_active Expired - Lifetime
- 2002-04-03 EP EP02735213A patent/EP1389177B1/en not_active Expired - Lifetime
- 2002-04-03 CA CA002442997A patent/CA2442997C/en not_active Expired - Fee Related
- 2002-04-03 BR BR0209159-3A patent/BR0209159A/pt active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| ITVA20010011A1 (it) | 2002-10-24 |
| EP1389177B1 (en) | 2008-10-08 |
| KR20040014497A (ko) | 2004-02-14 |
| CN1288123C (zh) | 2006-12-06 |
| US6995290B2 (en) | 2006-02-07 |
| BR0209159A (pt) | 2004-08-03 |
| JP2004527542A (ja) | 2004-09-09 |
| ES2314063T3 (es) | 2009-03-16 |
| ATE410402T1 (de) | 2008-10-15 |
| JP4355497B2 (ja) | 2009-11-04 |
| KR100877045B1 (ko) | 2008-12-31 |
| EP1389177A2 (en) | 2004-02-18 |
| US20040116549A1 (en) | 2004-06-17 |
| CN1529688A (zh) | 2004-09-15 |
| WO2002085832A2 (en) | 2002-10-31 |
| CA2442997A1 (en) | 2002-10-31 |
| DE60229234D1 (de) | 2008-11-20 |
| WO2002085832A3 (en) | 2002-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180403 |