JP6924255B2 - 水性感圧接着剤組成物およびその製造方法 - Google Patents
水性感圧接着剤組成物およびその製造方法 Download PDFInfo
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- JP6924255B2 JP6924255B2 JP2019506521A JP2019506521A JP6924255B2 JP 6924255 B2 JP6924255 B2 JP 6924255B2 JP 2019506521 A JP2019506521 A JP 2019506521A JP 2019506521 A JP2019506521 A JP 2019506521A JP 6924255 B2 JP6924255 B2 JP 6924255B2
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- unsaturated monomer
- acrylate
- mixture
- interpolymer
- adhesive composition
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 3
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- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
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- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
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- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
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- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
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- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
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- YOTGRUGZMVCBLS-UHFFFAOYSA-N pentadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C(C)=C YOTGRUGZMVCBLS-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
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- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
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- UCWBKJOCRGQBNW-UHFFFAOYSA-M sodium;hydroxymethanesulfinate;dihydrate Chemical compound O.O.[Na+].OCS([O-])=O UCWBKJOCRGQBNW-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- 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
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
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Description
接着剤組成物は、多種多様な目的に有用である。接着剤組成物の1つの特に有用なサブセットは、水性感圧接着剤である。異なる最終使用用途における水性感圧接着剤の使用は、一般に知られている。例えば、水性感圧接着剤は、ラベル、メモ帳、テープ、デカール、包帯、装飾用および保護用シート、ならびに多種多様な他の製品と共に使用することができる。当技術分野で使用されているように、「感圧接着剤」という用語は、乾燥時に室温で積極的かつ永久的に粘着性である1つ以上のポリマー組成物を含む材料を指す。さらに、用語「水性」は、感圧接着剤が水性キャリアを用いて製造されることを示す。典型的な水性感圧接着剤は、指または手で加える以上の圧力を必要とせずに、単なる接触で様々な異なる表面にしっかりと接着するであろう。
本開示を、例示的な実施例および比較例によって、これよりさらに詳細に説明する。しかしながら、本開示の範囲は、当然ながら、これらの例示の実施例に限定されない。
一般に、本開示による乳化混合物は以下のように調製される。コンデンサー、メカニカルスターラー、温度制御された熱電対ならびに開始剤およびモノマー用の入口を備えた4リットルの5つ口反応器に、675gの脱イオン(「DI」)水を供給し、穏やかなN2流の下で88℃に加熱する。別の容器中で、275gのDI水、10gのドデシルベンゼンスルホン酸ナトリウム界面活性剤、例えばSolvay S.A.,Brussels,BelgiumからのRHODACAL(商標)DS−4(「DS−4」)、11.9gの脂肪アルコールエーテルサルフェート界面活性剤、例えばBASF SE,Ludwigshafen,GermanyからのDISPONIL(商標)FES77界面活性剤(「FES−77」)、2.5gのNa2CO3、および2−エチルヘキシルアクリレート(「2−EHA」)、ブチルアクリレート(「BA」)、エチルアクリレート(「EA」)、メチルメタクリレート(「MMA」)、およびアクリル酸(「AA」)を含むモノマー混合物1,672gを混合することによって、モノマーエマルジョン(「ME」)を調製する。
全ての試料は、別途記載のない限り、実験室のドローダウンのために湿潤性を改善するために、全エマルジョンに基づいて、Cytec,Woodland Park,New Jerseyから入手した0.5%(湿潤/湿潤)AEROSOL(商標)GPG湿潤剤(「GPG」)などの湿潤剤が軽く配合される。次に、The Dow Chemical Company,Midland,MichiganからのACRYSOL(商標)RM−2020(「RM−2020」)などの増粘剤を使用して粘度を約600cps(Brookfield、RVDV、30rpm、63#)に調整して、最終pHを、アンモニアを用いて、7.0〜7.5に調整する。
ポリエチレン(「PE」)フィルムは積層前にコロナ処理によって前処理される。配合した接着剤を、乾燥重量基準で18g/m2の量で剥離ライナーに塗布し、80℃で6分間乾燥させる。接着剤層がPEフィルムのコロナ処理面と接触するように、PEフィルムを感圧接着剤被覆剥離ライナーと積層させて、接着剤積層体を得る。
性能試験は、接着ラミネートを制御された環境(22〜24℃、相対湿度50〜60%)の試験室で、少なくとも一晩コンディショニングした後に行う。
なお、本発明には、以下の態様が含まれることを付記する。
〔態様1〕
水性接着剤組成物であって、
水性媒体中に分散した少なくとも1つのインターポリマーを含み、前記インターポリマーが、少なくとも1つの不飽和モノマーと、少なくとも1つの共役酸、少なくとも1つの共役酸のモノエステル、およびこれらの混合物からなる群から選択される少なくとも1つの化合物とを含む、水性接着剤組成物。
〔態様2〕
前記少なくとも1つの共役酸が、少なくとも3つの共役二重結合を含む脂肪族カルボン酸を含む、態様1に記載の水性接着剤組成物。
〔態様3〕
前記少なくとも1つの共役酸が、桐油に由来する、態様1に記載の水性接着剤組成物。
〔態様4〕
前記少なくとも1つの不飽和モノマーが、2−エチルヘキシルアクリレート、エチルアクリレート、ブチルアクリレート、メチル(メタ)アクリレート、(メタ)アクリル酸、およびこれらの2つ以上の混合物からなる群から選択される、態様1に記載の水性接着剤組成物。
〔態様5〕
前記少なくとも1つの共役酸が前記インターポリマーの、0.01〜5重量パーセントを構成する、態様1に記載の水性接着剤組成物。
〔態様6〕
水性接着剤組成物を調製する方法であって、
少なくとも1つの不飽和モノマーと、少なくとも1つの界面活性剤とを、水性媒体中に分散させて、乳化混合物を形成することと、
前記乳化混合物に少なくとも1つの開始剤を導入し、これによって、前記少なくとも1つの不飽和モノマーを重合させることと、
少なくとも1つの共役酸、少なくとも1つの共役酸のモノエステル、およびこれらの混合物からなる群から選択される少なくとも1つの化合物を、少なくとも1つの不飽和モノマーの重合中に、前記乳化混合物に導入し、これによって、前記少なくとも1つの不飽和モノマーと、前記少なくとも1つのエステルとを含むインターポリマーを形成することと、を含む、方法。
〔態様7〕
前記少なくとも1つの共役酸が、桐油に由来することができる、態様6に記載の方法。
〔態様8〕
前記複数の不飽和モノマーの少なくとも50%が前記水性媒体に導入された後に、前記少なくとも1つの共役酸が、前記乳化混合物に導入される、態様6に記載の方法。
〔態様9〕
前記少なくとも1つの不飽和モノマーの少なくとも90%が前記水性媒体に導入された後に、前記少なくとも1つの共役酸が、前記乳化混合物に導入される、態様6に記載の方法。
〔態様10〕
態様6に従って調製された前記接着剤組成物を含む水性感圧接着剤。
Claims (9)
- 水性接着剤組成物であって、
水性媒体中に分散した少なくとも1つのインターポリマー
を含み、
前記インターポリマーが、少なくとも1つの不飽和モノマーと、前記インターポリマーの重量に基づき0.05〜2重量パーセントの、α−エレオステアリン酸を含む桐油脂肪酸混合物とを含む、前記水性接着剤組成物。 - 前記少なくとも1つの不飽和モノマーが、2−エチルヘキシルアクリレート、エチルアクリレート、ブチルアクリレート、メチル(メタ)アクリレート、(メタ)アクリル酸、およびこれらの2つ以上の混合物からなる群から選択される、請求項1に記載の水性接着剤組成物。
- 前記少なくとも1つの不飽和モノマーが、2−エチルヘキシルアクリレート、エチルアクリレート、ブチルアクリレート、メチル(メタ)アクリレート、および(メタ)アクリル酸である、または
前記少なくとも1つの不飽和モノマーが、2−エチルヘキシルアクリレート、エチルアクリレート、メチル(メタ)アクリレート、および(メタ)アクリル酸である、請求項1に記載の水性接着剤組成物。 - 前記インターポリマーは、前記インターポリマーの重量に基づき0.5〜1重量パーセントの前記桐油脂肪酸混合物を含む、請求項1〜3のいずれかに記載の水性接着剤組成物。
- 水性接着剤組成物を調製する方法であって、
少なくとも1つの不飽和モノマーと、少なくとも1つの界面活性剤とを、水性媒体中に分散させて、乳化混合物を形成することと、
前記乳化混合物に少なくとも1つの開始剤を導入し、これによって、少なくとも1つの不飽和モノマーを重合させることと、
α−エレオステアリン酸を含む桐油脂肪酸混合物を、前記少なくとも1つの不飽和モノマーの重合中に、前記乳化混合物に導入し、これによって、前記少なくとも1つの不飽和モノマーと、前記インターポリマーの重量に基づき0.05〜2重量パーセントの前記桐油脂肪酸混合物とを含むインターポリマーを形成することと
を含む、前記方法。 - 前記少なくとも1つの不飽和モノマーの少なくとも50%が前記水性媒体に導入された後に、前記桐油脂肪酸混合物が、前記乳化混合物に導入される、請求項5に記載の方法。
- 前記少なくとも1つの不飽和モノマーの少なくとも90%が前記水性媒体に導入された後に、前記桐油脂肪酸混合物が、前記乳化混合物に導入される、請求項5に記載の方法。
- 前記少なくとも1つの不飽和モノマーが、2−エチルヘキシルアクリレート、エチルアクリレート、ブチルアクリレート、メチル(メタ)アクリレート、および(メタ)アクリル酸である、または
前記少なくとも1つの不飽和モノマーが、2−エチルヘキシルアクリレート、エチルアクリレート、メチル(メタ)アクリレート、および(メタ)アクリル酸である、請求項5〜7のいずれかに記載の方法。 - 前記インターポリマーは、前記インターポリマーの重量に基づき0.5〜1重量パーセントの前記桐油脂肪酸混合物を含む、請求項5〜8のいずれかに記載の方法。
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WO2018027888A1 (en) | 2018-02-15 |
US20210284874A1 (en) | 2021-09-16 |
RU2019105600A (ru) | 2020-08-27 |
BR112019002605B1 (pt) | 2022-04-19 |
JP2019528344A (ja) | 2019-10-10 |
RU2019105600A3 (ja) | 2020-08-27 |
TWI759314B (zh) | 2022-04-01 |
AR109200A1 (es) | 2018-11-07 |
MX2019001541A (es) | 2019-07-04 |
EP3497176A4 (en) | 2020-01-22 |
US11926770B2 (en) | 2024-03-12 |
EP3497176A1 (en) | 2019-06-19 |
CN109689823B (zh) | 2021-06-25 |
RU2748660C2 (ru) | 2021-05-28 |
CN109689823A (zh) | 2019-04-26 |
TW201809196A (zh) | 2018-03-16 |
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