JP6274965B2 - 可逆性ポリマー接着剤組成物 - Google Patents
可逆性ポリマー接着剤組成物 Download PDFInfo
- Publication number
- JP6274965B2 JP6274965B2 JP2014100000A JP2014100000A JP6274965B2 JP 6274965 B2 JP6274965 B2 JP 6274965B2 JP 2014100000 A JP2014100000 A JP 2014100000A JP 2014100000 A JP2014100000 A JP 2014100000A JP 6274965 B2 JP6274965 B2 JP 6274965B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive composition
- reversible
- furan
- maleimide
- adhesive
- 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
- 239000000203 mixture Substances 0.000 title claims description 162
- 230000001070 adhesive effect Effects 0.000 title claims description 111
- 239000000853 adhesive Substances 0.000 title claims description 107
- 230000002441 reversible effect Effects 0.000 title claims description 66
- 229920000642 polymer Polymers 0.000 title claims description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 93
- 239000000463 material Substances 0.000 claims description 57
- 239000007788 liquid Substances 0.000 claims description 52
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 43
- 239000007787 solid Substances 0.000 claims description 41
- -1 maleimide compound Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 238000006352 cycloaddition reaction Methods 0.000 claims description 23
- 125000005647 linker group Chemical group 0.000 claims description 19
- 238000001816 cooling Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000002861 polymer material Substances 0.000 claims description 12
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 11
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 3
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- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 6
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
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- 238000006117 Diels-Alder cycloaddition reaction Methods 0.000 description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 description 3
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- 125000006850 spacer group Chemical group 0.000 description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- RPDUDBYMNGAHEM-UHFFFAOYSA-N PROXYL Chemical group CC1(C)CCC(C)(C)N1[O] RPDUDBYMNGAHEM-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 230000003078 antioxidant effect Effects 0.000 description 2
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- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B37/1284—Application of adhesive
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B37/1284—Application of adhesive
- B32B37/1292—Application of adhesive selectively, e.g. in stripes, in patterns
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/121—Preparatory processes from unsaturated precursors and polyamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/128—Unsaturated polyimide precursors the unsaturated precursors containing heterocyclic moieties in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- 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
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
-
- 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
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09J179/085—Unsaturated polyimide precursors
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B37/1207—Heat-activated adhesive
- B32B2037/1215—Hot-melt adhesive
- B32B2037/1223—Hot-melt adhesive film-shaped
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/31—Heat sealable
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2309/00—Parameters for the laminating or treatment process; Apparatus details
- B32B2309/02—Temperature
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2355/00—Specific polymers obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of index codes B32B2323/00 - B32B2333/00
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2405/00—Adhesive articles, e.g. adhesive tapes
-
- 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
- C09J2477/00—Presence of polyamide
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/905,729 | 2013-05-30 | ||
| US13/905,729 US9193139B2 (en) | 2013-05-30 | 2013-05-30 | Reversible polymer adhesive composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014234514A JP2014234514A (ja) | 2014-12-15 |
| JP2014234514A5 JP2014234514A5 (OSRAM) | 2017-06-22 |
| JP6274965B2 true JP6274965B2 (ja) | 2018-02-07 |
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ID=51899632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014100000A Expired - Fee Related JP6274965B2 (ja) | 2013-05-30 | 2014-05-13 | 可逆性ポリマー接着剤組成物 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US9193139B2 (OSRAM) |
| JP (1) | JP6274965B2 (OSRAM) |
| DE (1) | DE102014209708A1 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6613649B2 (ja) * | 2014-06-23 | 2019-12-04 | 東洋インキScホールディングス株式会社 | 接着剤組成物、積層シート、太陽電池用裏面保護シート |
| CN112750741B (zh) * | 2019-10-29 | 2023-01-03 | 成都辰显光电有限公司 | 一种微元件的转移基板及转移方法 |
| US20240271012A1 (en) * | 2023-02-14 | 2024-08-15 | The Boeing Company | Thermoreversible urethane-based adhesive compositions and associated methods for bonding and bonded articles |
| EP4461758A1 (en) * | 2023-05-11 | 2024-11-13 | Vito NV | Reversible lignin adhesive |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4303924A (en) | 1978-12-26 | 1981-12-01 | The Mead Corporation | Jet drop printing process utilizing a radiation curable ink |
| US4978969A (en) | 1989-07-05 | 1990-12-18 | Hewlett-Packard Company | Method for printing using ultra-violet curable ink |
| US5270368A (en) | 1992-07-15 | 1993-12-14 | Videojet Systems International, Inc. | Etch-resistant jet ink and process |
| IL111014A (en) | 1994-09-21 | 1999-05-09 | Scitex Corp Ltd | Ink compositions and a method for making same |
| TW338044B (en) * | 1994-11-15 | 1998-08-11 | Shell Internattonale Res Mij B V | A cross linked resin |
| US5840215A (en) * | 1996-12-16 | 1998-11-24 | Shell Oil Company | Anisotropic conductive adhesive compositions |
| US5760337A (en) * | 1996-12-16 | 1998-06-02 | Shell Oil Company | Thermally reworkable binders for flip-chip devices |
| US5844020A (en) | 1997-03-31 | 1998-12-01 | Xerox Corporation | Phase change ink compositions |
| JP4031866B2 (ja) * | 1998-06-16 | 2008-01-09 | 横浜ゴム株式会社 | リサイクル性エラストマー |
| US6042227A (en) | 1998-05-19 | 2000-03-28 | Xerox Corporation | Hot melt phase change ink containing Diels-Alder polymerization precursor |
| JP2000037802A (ja) * | 1998-07-24 | 2000-02-08 | Dainippon Ink & Chem Inc | 大面積積層体の製造法 |
| US6883908B2 (en) * | 2001-01-08 | 2005-04-26 | 3M Innovative Properties Company | Methods and compositions for ink jet printing of pressure sensitive adhesive patterns or films on a wide range of substrates |
| US6825315B2 (en) * | 2001-12-21 | 2004-11-30 | Sandia Corporation | Method of making thermally removable adhesives |
| DE102007062316A1 (de) * | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | Reaktive Isocyanatzusammensetzungen |
| JP5544615B2 (ja) * | 2009-05-14 | 2014-07-09 | 独立行政法人産業技術総合研究所 | 熱可逆反応型高分子組成物 |
| EP2440627B1 (en) * | 2009-06-11 | 2015-03-04 | Henkel US IP LLC | Thermally reversible hot melt adhesive composition containing multifunctional diene and dienophile compounds |
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- 2013-05-30 US US13/905,729 patent/US9193139B2/en active Active
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2014
- 2014-05-13 JP JP2014100000A patent/JP6274965B2/ja not_active Expired - Fee Related
- 2014-05-21 DE DE102014209708.8A patent/DE102014209708A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20140352884A1 (en) | 2014-12-04 |
| US9193139B2 (en) | 2015-11-24 |
| DE102014209708A1 (de) | 2014-12-04 |
| JP2014234514A (ja) | 2014-12-15 |
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