JP4544592B2 - カプセル化されたマイケル付加触媒 - Google Patents
カプセル化されたマイケル付加触媒 Download PDFInfo
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- JP4544592B2 JP4544592B2 JP2007013490A JP2007013490A JP4544592B2 JP 4544592 B2 JP4544592 B2 JP 4544592B2 JP 2007013490 A JP2007013490 A JP 2007013490A JP 2007013490 A JP2007013490 A JP 2007013490A JP 4544592 B2 JP4544592 B2 JP 4544592B2
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- Japan
- Prior art keywords
- acetoacetate
- catalyst
- bisacetoacetate
- encapsulated
- potassium
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
- C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/068—Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09J165/00—Adhesives based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Adhesives based on derivatives of such polymers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Description
SR−259(商標)− Sartomer companyから得られるポリエチレングリコールジアクリレート
MorCure 2000(商標)− Rohm and Haas Companyから得られるビスフェノールAジグリシジルエポキシジアクリレート
TMPトリスAcAc − トリメチロールプロパントリスアセトアセテート
カプセル化された触媒を2グラムのNa2CO3から製造し、325メッシュのスクリーンを通過するように粉砕し、次いで110℃で2時間乾燥させ、コーティングとして5グラムのIsolene(商標)40と混合した。実施例10はラミネート接着剤配合物を記載する。
実施例10のラミネート接着剤配合物(66.42グラム)を、7グラムのIsolene40でコーティングされたNa2CO3(2.7%Na2CO3を与える)と、最終配合接着剤中で混合した。粘度データを接着剤について測定し、以下の通りであった:
実施例12
実施例12のラミネート接着剤配合物(100グラム)を前記のように10.4グラムのカプセル化された触媒と混合して、接着剤配合物中2.7重量%の触媒を得た。
実施例12のラミネート接着剤配合物(100グラム)を10.4グラムの触媒と混合して、最終接着剤配合物において2.7%の触媒を得た。粘度データを接着剤について測定し、次の通りであった:
Claims (6)
- (a)(i)構造(I)を有する少なくとも1つの官能基を有する化合物から選択される少なくとも1つのマイケル受容体:
(ii)メチルアセトアセテート、エチルアセトアセテート、n−プロピルアセトアセテート、イソプロピルアセトアセテート、n−ブチルアセトアセテート、t−ブチルアセトアセテート、エチレングリコールビスアセトアセテート、1,2プロパンジオールビスアセトアセテート、1,3プロパンジオールビスアセトアセテート、1,4ブタンジオールビスアセトアセテート、ネオペンチルグリコールビスアセトアセテート、イソソルビドビスアセトアセテート、トリメチロールプロパントリスアセトアセテート、グリセロールトリスアセトアセテート、ヒマシ油トリスアセトアセテート、グルコーストリスアセトアセテート、グルコーステトラアセトアセテート、スクロースアセトアセテート、ソルビトールトリスアセトアセテート、ソルビトールテトラアセトアセテート、エトキシル化およびプロポキシル化ジオール、トリオールおよびポリオールのアセトアセテート、エトキシル化ネオペンチルグリコールビスアセトアセテート、プロポキシル化グルコースアセトアセテート、プロポキシル化ソルビトールアセトアセテート、プロポキシル化スクロースアセトアセテート、ポリエステルが少なくとも1つの二酸および少なくとも1つのジオール由来であるポリエステルアセトアセテート、ポリエステルアミドが少なくとも1つの二酸および少なくとも1つのジアミン由来であるポリエステルアミドアセトアセテート、1,2エチレンビスアセトアミド、1,4ブタンビスアセトアミド、1,6ヘキサンビスアセトアセトアミド、ピペラジンビスアセトアミド、アミン末端ポリプロピレングリコールのアセトアミド、ポリエステルアミドが少なくとも1つの二酸および少なくとも1つのジアミン由来であるポリエステルアミドアセトアセテートのアセトアミド、アセトアセトキシ官能基を有するコモノマーを含有するポリアクリレート、ならびにアセトアセトキシ官能基およびシリル化コモノマーを含有するポリアクリレート:からなる群から選択される少なくとも1つのマイケル供与体;および
(iii)グアニジン、アミジン、ヒドロキシド、アルコキシド、オキシド、ターシャリーアミン、アルカリ金属炭酸塩、アルカリ金属重炭酸塩、アルカリ金属リン酸塩、アルカリ金属リン酸水素塩、ホスフィン、カルボン酸のアルカリ金属塩、アルカリ珪酸塩、テトラメチルグアニジン、1,8−ジアザビシクロ(5.4.0)ウンデセ−7−エン、1,5−ジアザビシクロ(4.3.0)ノン−5−エン、1,4ジアザビシクロ(2.2.2)オクタン、ターシャリーブチルアンモニウムヒドロキシド、水酸化ナトリウム、水酸化カリウム、ナトリウムメトキシド、ナトリウムエトキシド、リン酸三カリウム、酸化カルシウム、トリエチルアミン、炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウム、重炭酸カリウム、リン酸水素カリウム(一塩基性および二塩基性)、トリフェニルホスフィン、トリエチルホスフィン、珪酸ナトリウム、酢酸カリウム、アクリル酸カリウム、およびオクタン酸カリウム:からなる群から選択される少なくとも1つのカプセル化された触媒、ここで該1以上のカプセル化された触媒のカプセルは0.1〜500μmの粒子サイズを有する:
を含む組成物を少なくとも1つの基体に適用する工程;
(b)前記組成物を第二の基体に接触させる工程;
(c)圧力により前記カプセルを破裂させる工程;並びに
(d)前記工程(b)の後のマイケル付加により前記組成物を硬化させる工程:
を含む、少なくとも2つの基体を接着する方法。 - 前記R1、R2、およびR4はそれぞれ、独立して、水素;並びにアルキル、アリール、アリール置換アルキルおよびアルキル置換アリールから選択される有機基;から選択され、R3は酸素;窒素含有基;またはアルキル、アリール、アリール置換アルキルおよびアルキル置換アリールから選択される有機基である、請求項1記載の方法。
- 前記1以上のカプセル化された触媒のカプセルが、0.1〜100μmの粒子サイズ有する、請求項1記載の方法。
- 前記カプセル化された触媒をカプセル化するために用いられる物質が、合成ワックス、微結晶ワックス、植物性ワックス、ポリエチレンワックス、ポリアミド、ポリ尿素、マイケル付加ポリマー、ポリアクリレート、側鎖結晶性ポリアクリレート、ポリビニルアルコール、ボレートなどのクロスリンカーを使用する架橋ポリビニルアルコール、ポリジメチルシロキサン、カルボキシメチルセルロース、ポリスチレン、ポリエチレンビニルアセテートコポリマー、ポリエチレンアクリレートコポリマー、ポリアルファオレフィン、ポリエチレン、不均一触媒反応により製造されたポリエチレン、ポリプロピレンおよびポリプロピレンから選択される、請求項1記載の方法。
- 前記触媒が4〜11のpKbを有する、請求項1記載の方法。
- 前記組成物が、前記(i)、前記(ii)及び前記(iii)から成る、請求項1記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US76220206P | 2006-01-25 | 2006-01-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007217686A JP2007217686A (ja) | 2007-08-30 |
JP4544592B2 true JP4544592B2 (ja) | 2010-09-15 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2007013490A Expired - Fee Related JP4544592B2 (ja) | 2006-01-25 | 2007-01-24 | カプセル化されたマイケル付加触媒 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20070173602A1 (ja) |
EP (1) | EP1813630B1 (ja) |
JP (1) | JP4544592B2 (ja) |
KR (1) | KR20070078063A (ja) |
CN (1) | CN101012291B (ja) |
BR (1) | BRPI0700100B1 (ja) |
CA (1) | CA2573695A1 (ja) |
DE (1) | DE602007005031D1 (ja) |
MX (1) | MX2007000747A (ja) |
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Also Published As
Publication number | Publication date |
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BRPI0700100A (pt) | 2007-11-06 |
DE602007005031D1 (de) | 2010-04-15 |
CA2573695A1 (en) | 2007-07-25 |
BRPI0700100A8 (pt) | 2017-07-11 |
KR20070078063A (ko) | 2007-07-30 |
BRPI0700100B1 (pt) | 2018-02-14 |
EP1813630A2 (en) | 2007-08-01 |
JP2007217686A (ja) | 2007-08-30 |
CN101012291A (zh) | 2007-08-08 |
US20070173602A1 (en) | 2007-07-26 |
EP1813630A3 (en) | 2007-11-28 |
CN101012291B (zh) | 2010-04-07 |
EP1813630B1 (en) | 2010-03-03 |
MX2007000747A (es) | 2008-10-29 |
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