JPH0386777A - Water-base peeling agent - Google Patents
Water-base peeling agentInfo
- Publication number
- JPH0386777A JPH0386777A JP22179389A JP22179389A JPH0386777A JP H0386777 A JPH0386777 A JP H0386777A JP 22179389 A JP22179389 A JP 22179389A JP 22179389 A JP22179389 A JP 22179389A JP H0386777 A JPH0386777 A JP H0386777A
- Authority
- JP
- Japan
- Prior art keywords
- base
- water
- chain alkyl
- peeling agent
- sensitive
- 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.)
- Granted
Links
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- -1 alkyl isocyanate Chemical class 0.000 claims abstract description 15
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 12
- 229920000083 poly(allylamine) Polymers 0.000 claims abstract description 10
- 239000006185 dispersion Substances 0.000 claims abstract description 9
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 8
- 238000001035 drying Methods 0.000 abstract description 6
- 239000002985 plastic film Substances 0.000 abstract description 5
- 229920006255 plastic film Polymers 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000000123 paper Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 3
- 229920000298 Cellophane Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MEMUMYCLWQPAEX-UHFFFAOYSA-N n-octadecylaziridine-1-carboxamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)N1CC1 MEMUMYCLWQPAEX-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000005026 oriented polypropylene Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- GFLXBRUGMACJLQ-UHFFFAOYSA-N 1-isocyanatohexadecane Chemical compound CCCCCCCCCCCCCCCCN=C=O GFLXBRUGMACJLQ-UHFFFAOYSA-N 0.000 description 1
- RWCDAKQLMGCVLI-UHFFFAOYSA-N 1-isocyanatoicosane Chemical compound CCCCCCCCCCCCCCCCCCCCN=C=O RWCDAKQLMGCVLI-UHFFFAOYSA-N 0.000 description 1
- XDCBSPQSPOCKEV-UHFFFAOYSA-N 1-isocyanatononadecane Chemical compound CCCCCCCCCCCCCCCCCCCN=C=O XDCBSPQSPOCKEV-UHFFFAOYSA-N 0.000 description 1
- HULTVDSPXGVYBQ-UHFFFAOYSA-N 1-isocyanatopentadecane Chemical compound CCCCCCCCCCCCCCCN=C=O HULTVDSPXGVYBQ-UHFFFAOYSA-N 0.000 description 1
- CSMJMAQKBKGDQX-UHFFFAOYSA-N 1-isocyanatotetradecane Chemical compound CCCCCCCCCCCCCCN=C=O CSMJMAQKBKGDQX-UHFFFAOYSA-N 0.000 description 1
- BAZBBHGFCBVAQU-UHFFFAOYSA-N 1-isocyanatotridecane Chemical compound CCCCCCCCCCCCCN=C=O BAZBBHGFCBVAQU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- KPPONQWQFTVQMM-UHFFFAOYSA-N 3-ethenylpyrrolidine-2,5-dione Chemical compound C=CC1CC(=O)NC1=O KPPONQWQFTVQMM-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 229920006378 biaxially oriented polypropylene Polymers 0.000 description 1
- 239000011127 biaxially oriented polypropylene Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- MGPYDQFQAJEDIG-UHFFFAOYSA-N ethene;urea Chemical group C=C.NC(N)=O MGPYDQFQAJEDIG-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 239000011092 plastic-coated paper Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Adhesive Tapes (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、主として紙やプラスチックフィルムを基材と
する感圧粘着テープまたはシートに用いられる水性の剥
Ｍ剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an aqueous M stripping agent used for pressure-sensitive adhesive tapes or sheets mainly based on paper or plastic film.
−ａに、感圧粘着テープ、シートなどにおいてはその粘
着面の保護のため、粘着剤塗布面に剥離紙を貼着するか
、ロール状に巻いてその粘着剤塗布面を基材の背面に貼
着することが行われている。-a. For pressure-sensitive adhesive tapes, sheets, etc., in order to protect the adhesive surface, either attach release paper to the adhesive-coated side, or roll it up and place the adhesive-coated side on the back of the base material. Pasting is done.
この剥離紙の表面や基材の背面には、使用時における剥
離性を良くするために剥離剤が塗布される。A release agent is applied to the surface of the release paper and the back surface of the base material in order to improve releasability during use.
［従来の技術］
従来、剥離剤としてはポリビニルアルコール−オクタデ
シルイソシアネート付加物（特公昭２つ一７３３３号公
報）、ポリエチレンイミン−オクタデシルイソシアネー
ト付加物（特公昭４０−１７６６１号公報）などの溶剤
型のものが知られていた。これらの剥離剤は品質面では
優れた性質を持つものの、塗工時に大量の有機溶剤を使
用するため、作業環境の悪化、公害などの問題から溶剤
の回収行程を必要とし、さらに、近年の有機溶剤の価格
の上昇もあり、水性の剥離剤への要求が高まっている。[Prior Art] Conventionally, solvent-based stripping agents such as polyvinyl alcohol-octadecyl isocyanate adduct (Japanese Patent Publication No. 17333/1983) and polyethyleneimine-octadecyl isocyanate adduct (Japanese Patent Publication No. 17661/1989) have been used as release agents. Things were known. Although these stripping agents have excellent properties in terms of quality, they use large amounts of organic solvents during coating, so they require a solvent recovery process due to problems such as deterioration of the working environment and pollution. Due in part to the rising cost of solvents, demand for water-based strippers is increasing.
水性の剥離剤としては、酸性基を有するモノマーと、そ
の他のモノマーからなる共重合体のエマルジョンとオク
タデシルエチレン尿素のエマルジョンとの混合物〈特公
昭５２−６３８５号公報）などが知られていた。しかし
、このようなエマルジョン混合物型の水性剥離剤では、
塗工後乾燥時に共重合体とオクタデシルエチレン尿素の
反応を行わせるために、高温で処理する必要があり、高
温に耐える基材にしか使用できないという問題があった
。As an aqueous release agent, a mixture of an emulsion of a copolymer consisting of a monomer having an acidic group and another monomer, and an emulsion of octadecyl ethylene urea (Japanese Patent Publication No. 6385/1985) has been known. However, with such emulsion mixture type water-based removers,
In order to cause the copolymer to react with octadecylethylene urea during drying after coating, it is necessary to treat the copolymer at a high temperature, which poses the problem that it can only be used on substrates that can withstand high temperatures.
［発明が解決しようとする問題点］
水で稀釈して使用でき、より広範な基材に使用できる剥
離剤について検討を重ねた結果、ポリアミンに長鎖アル
キル基をグラフトしたポリマーを、後乳化することによ
り、問題を解決し得ることを見いだし本発明を完成する
に至った。[Problems to be solved by the invention] As a result of repeated studies on a release agent that can be diluted with water and used on a wider variety of base materials, we have developed a method for post-emulsifying a polymer in which a long-chain alkyl group is grafted onto a polyamine. By doing so, they discovered that the problem could be solved and completed the present invention.
［問題点を解決するための手段］
本発明はポリビニルアミンまたはポリアリルアミンとア
ルキルイソシアネートを反応させることによって得られ
る長鎖アルキルグラフトポリマーを後乳化することによ
って得られる水分散体を用いることを特徴とする水性剥
離剤に間、するものである。[Means for Solving the Problems] The present invention is characterized in that it uses an aqueous dispersion obtained by post-emulsifying a long-chain alkyl graft polymer obtained by reacting polyvinylamine or polyallylamine with an alkyl isocyanate. Use a water-based remover to remove the skin.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
従来報告されている水性の剥離剤は、エチレン尿素基、
Ｎ−メチロール基、カルボン酸の金属塩、などの官能基
を持った長鎖アルキルと、これと反応し得る官能基を持
ち被膜形成能を持つ重合体をそれぞれエマルジョン化し
た後に混合するというものであった。これらのものは、
エマルジョン状態で安定に存在させるために、反応性を
抑える必要があるにもかかわらず、塗工後難時間の乾燥
行程で反応を完結しなくてはならないと言う矛盾した要
求に答えるため、どうしても高温で反応させる必要があ
った。Previously reported water-based release agents have ethylene urea groups,
A long-chain alkyl having a functional group such as an N-methylol group or a metal salt of carboxylic acid is emulsified with a polymer having a functional group capable of reacting with the long-chain alkyl and capable of forming a film, and then mixed together. there were. These things are
Although it is necessary to suppress reactivity in order to stably exist in an emulsion state, high temperatures are unavoidable in order to meet the contradictory demands of completing the reaction in a drying process that takes a long time after coating. It was necessary to react.
これに対して、本発明のポリビニルアミンまたはポリア
リルアミンの長鎖アルキルグラフトポリマーを後乳化す
ることによって得られる水性の剥離剤では、保存安定性
が良く、塗工後の乾燥行程で反応を行う必要がないため
高温処理が不用となり、高温処理に耐えられない基材を
使用している感圧粘着テープ、シートにも使用が可能で
ある。On the other hand, the aqueous release agent obtained by post-emulsifying the long-chain alkyl graft polymer of polyvinylamine or polyallylamine of the present invention has good storage stability and requires no reaction during the drying process after coating. This eliminates the need for high-temperature treatment, and it can also be used for pressure-sensitive adhesive tapes and sheets that use base materials that cannot withstand high-temperature treatment.
本発明において用いられる長鎖アルキルグラフトポリマ
ーは、ポリビニルアミンまたはポリアリルアミンと、炭
素数が８以上のアルキル鎖を有するアルキルイソシアネ
ートを反応させることによって製造することができる。The long-chain alkyl graft polymer used in the present invention can be produced by reacting polyvinylamine or polyallylamine with an alkyl isocyanate having an alkyl chain having 8 or more carbon atoms.
本発明で用いられるポリビニルアミン、アリルアミンま
たはその変性物としては、無変性のポリビニルアミン、
ポリアリルアミンの他、コモノマーとして、エチレン、
プロピレンなどのオレフィン、アクリルアミド、メタク
リルアミド、Ｎ、Ｎ−ジメチルアクリルアミドなどのア
クリルアミド類、アクリル酸、メタクリル酸、クロトン
酸、マレイン酸、フマル酸、イタコン酸などの不飽和カ
ルボン酸及びそのエステルや無水物、ビニルスルホン酸
などのスルホン酸モノマー、ジメチルアミノエチルメタ
クリレート、ビニルイミダゾール、ビニルピリジン、ビ
ニルスクシンイミドなどのカチオン変性モノマー、アリ
ルアセテート、ビニルアルコール、アリルアルコールな
どのうちの一種から数種のモノマーを含むポリビニルア
ミン、ポリアリルアミンの共重合変性物があげられる。Polyvinylamine, allylamine or modified products thereof used in the present invention include unmodified polyvinylamine,
In addition to polyallylamine, ethylene,
Olefins such as propylene, acrylamides such as acrylamide, methacrylamide, and N,N-dimethylacrylamide, unsaturated carboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, and itaconic acid, and their esters and anhydrides. , sulfonic acid monomers such as vinyl sulfonic acid, cationically modified monomers such as dimethylaminoethyl methacrylate, vinyl imidazole, vinyl pyridine, vinyl succinimide, allyl acetate, vinyl alcohol, allyl alcohol, etc. Examples include copolymerized modified products of amine and polyallylamine.
また、このようなポリビニルアミン、アリルアミンまた
はそれらの変性物に、さらに変性を腫したものでも良い
。Further, polyvinylamine, allylamine, or modified products thereof may be further modified.
本発明において用いられるアルキルイソシアネートは、
炭素数が８以上のアルキル基を有する１価のイソシアネ
ートで、特に剥離性の点や入手し易さの点から炭素数が
１２〜３０のアルキル基を有するものが望ましい、その
例としては、ドデシルイソシアネート、トリデシルイソ
シアネート、テトラデシルイソシアネート、ペンタデシ
ルイソシアネート、ヘキサデシルイソシアネート、オク
タデシルイソシアネート、ノナデシルイソシアネート、
エイコシルイソシアネートなどの長鎖アルキルイソシア
ネートがあげられる。The alkyl isocyanate used in the present invention is
A monovalent isocyanate having an alkyl group having 8 or more carbon atoms, especially one having an alkyl group having 12 to 30 carbon atoms is preferable from the viewpoint of releasability and availability. Examples include dodecyl. Isocyanate, tridecyl isocyanate, tetradecyl isocyanate, pentadecyl isocyanate, hexadecyl isocyanate, octadecyl isocyanate, nonadecyl isocyanate,
Examples include long chain alkyl isocyanates such as eicosyl isocyanate.
ポリビニルアミンまたはポリアリルアミンと、イソシア
ネートの反応は主としてトルエン、キシレンなどの芳香
族系の有機溶媒または酢酸エチル等のエステル系の有機
溶媒、シクロヘキサン、ヘキサン等の脂肪族、脂環族の
炭化水素系有機溶媒中などで行われ、有機溶媒の溶液と
して長鎖アルキルグラフトポリマーを得ることができる
。必要であれば、この溶液をイソプロパツールなどの親
水性溶媒と混合し、ポリマーを析出させた後、濾過、乾
燥することにより長鎖アルキルグラフトポリマーを粉体
として得ることもできる。The reaction between polyvinylamine or polyallylamine and isocyanate is mainly carried out using aromatic organic solvents such as toluene and xylene, ester organic solvents such as ethyl acetate, and aliphatic and alicyclic hydrocarbon organic solvents such as cyclohexane and hexane. The long-chain alkyl graft polymer can be obtained as a solution in an organic solvent. If necessary, the long-chain alkyl graft polymer can be obtained as a powder by mixing this solution with a hydrophilic solvent such as isopropanol to precipitate the polymer, followed by filtration and drying.
本発明の水性剥離剤は、上記の長鎖アルキルグラフトポ
リマーを一般的な方法で乳化することにより得ることが
できる。具体的には、長鎖アルキルグラフトポリマーの
有機溶剤溶液を界面活性剤の水溶液中に攪拌混合し乳化
した後、必要に応じて有機溶剤を除去することにより得
ることができる。また、有機溶剤を使用せず、長鎖アル
キルグラフトポリマーと界面活性剤を水の存在下で加圧
ニーダ−、コロイドミル等をを使用して乳化分散するこ
ともできる。The aqueous release agent of the present invention can be obtained by emulsifying the above-mentioned long-chain alkyl graft polymer by a conventional method. Specifically, it can be obtained by stirring and mixing an organic solvent solution of a long-chain alkyl graft polymer into an aqueous surfactant solution to emulsify it, and then removing the organic solvent as necessary. It is also possible to emulsify and disperse the long-chain alkyl graft polymer and surfactant in the presence of water using a pressure kneader, colloid mill, etc. without using an organic solvent.
本発明の後乳化において用いられる界面活性剤の種類に
は特に制限はないが、乳化に際して０／Ｗ型のエマルジ
ョンを作り得る比較的親水性の高いものが好適である。The type of surfactant used in the post-emulsification of the present invention is not particularly limited, but a relatively highly hydrophilic surfactant that can form an 0/W type emulsion during emulsification is preferred.
具体的な例とし、ては、ポリオキシエチレンノニルフェ
ニルエーテル、ポリオキシエチレンステアリルエーテル
などのノニオン系界面活性剤、ラウリル硫酸ナトリウム
、ポリオキシエチレンノニルフェニルエーテル硫酸ナト
リウムなどのアニオン系界面活性剤、またはステアリル
アミンアセテート、ステアリルトリメチルアンモニウム
クロライドなどのカチオン系界面活性剤などが使用でき
る。Specific examples include nonionic surfactants such as polyoxyethylene nonylphenyl ether and polyoxyethylene stearyl ether; anionic surfactants such as sodium lauryl sulfate and sodium polyoxyethylene nonylphenyl ether sulfate; Cationic surfactants such as stearylamine acetate and stearyltrimethylammonium chloride can be used.
界面活性剤の量は、長鎖アルキルグラフトポリマーに対
し、３〜３０重量％が好ましい、これより少ないと安定
なエマルジョンができにくく、多いと剥離性能に悪影響
をおよぼす。The amount of surfactant is preferably 3 to 30% by weight based on the long-chain alkyl graft polymer; if it is less than this, it is difficult to form a stable emulsion, and if it is more than this, it will adversely affect the peeling performance.
本発明の水性Ｈ離削は、一般の塗布機器で塗布できる。The aqueous H-abrasive of the present invention can be applied using general coating equipment.
具体的な例としてはロールコータ−、グラビアコーター
リップコーターなどが挙げられる。Specific examples include roll coaters, gravure coaters, lip coaters, and the like.
また、本発明の剥離剤を塗布できる基材としてはポリエ
チレン、ポリプロピレン、ポリエステル、セロファンな
どのプラスチックフィルムや、上質紙、クラフト紙、ク
レープ紙、グラシン紙などの他、含浸紙、プラスチック
コート紙などの目止めをほどこした紙、布などが挙げら
れる。In addition, substrates to which the release agent of the present invention can be applied include plastic films such as polyethylene, polypropylene, polyester, and cellophane, as well as high-quality paper, kraft paper, crepe paper, glassine paper, as well as impregnated paper and plastic coated paper. Examples include paper and cloth that have been sealed.
本発明の水性剥離剤をポリエステル、セロファン、ポリ
プロピレンなとのプラスチックフィルムに塗布するに当
たっては、塗布液中に必要に応じて親水性の有機溶剤を
添加してもよい、特に、低分子量のアルコール類が好適
で、具体的には、メタノール、エタノール、イソプロパ
ツール、ｎ−プロパツールなどが使用できる。また、市
販の湿′ｉＲ剤、濡れ性向上剤、具体的な例としては、
サーフィノール４６５（自信化学工業（！１）Ｂｙｋ−
１８１（ビックゲミー・ジャパンｆｔ、）、Ｎｏｐｃｐ
ｗｅｔ ５Ｎ−２０Ｔ（サンノブコ＠Ｊ＞なども使用
できる。When applying the aqueous release agent of the present invention to a plastic film such as polyester, cellophane, or polypropylene, a hydrophilic organic solvent may be added to the coating solution as necessary, especially a low molecular weight alcohol. is preferable, and specifically, methanol, ethanol, isopropanol, n-propatool, etc. can be used. In addition, commercially available moisture iR agents and wettability improvers, specific examples include:
Surfynol 465 (Shinji Kagaku Kogyo (!1) Byk-
181 (Big Game Japan ft,), Nopcp
Wet 5N-20T (San Nobuko@J> etc. can also be used.
［実 施 例］
以下の実施例で、本発明について具体的に説明するが、
これにより限定されることはない。[Example] The present invention will be specifically explained in the following example.
This is not a limitation.
合成例１
撹拌機と冷却器と滴下ロートを備えた反応器中で、ポリ
ビニルアミン１０重量部トルエン１３５重量部中に分散
し、４８重量部のオクタデシルイソシアネートを加え、
さらに３時間還流しｆＳ後、トノ５エンを留出させ不揮
発分を４０ｗｔ％まで濃縮す乞ことにより、ポリビニル
アミン−オクタデシルイソシアネート付加物のトルエン
溶液を得た。Synthesis Example 1 In a reactor equipped with a stirrer, a condenser, and a dropping funnel, 10 parts by weight of polyvinylamine were dispersed in 135 parts by weight of toluene, and 48 parts by weight of octadecyl isocyanate were added.
After further refluxing for 3 hours, tono5ene was distilled off and the nonvolatile content was concentrated to 40 wt%, thereby obtaining a toluene solution of polyvinylamine-octadecyl isocyanate adduct.
カチオン系界面活性剤（ステアリルトリメチルアンモニ
ウムクロライド）８重量部を水１４２重量部に溶かし、
上記のトルエン溶液１ｏｏ重量部を加え７０℃で３０分
間ホモジナイザーで撹拌し、ポリビニルアミン−オクタ
デシルイソシアネート付加物の水分散体を得た。Dissolve 8 parts by weight of a cationic surfactant (stearyltrimethylammonium chloride) in 142 parts by weight of water,
10 weight parts of the above toluene solution was added and stirred at 70°C for 30 minutes with a homogenizer to obtain an aqueous dispersion of polyvinylamine-octadecyl isocyanate adduct.
合成例２
ポリアリルアミン１０重量部と、オクタデシルイソシア
ネート３５重量部を用い合成例１と同様な方法で、ポリ
アリルアミン−オクタデシルイソシアネート付加物のト
ルエン溶液を得た。 ノニオン系界面活性剤（ポリオキ
シエチレンノニルフェニルエーテルＨＬＢ１７．５）１
０重量部を用い、合成例１と同様にしてポリアリルアミ
ン−オクタデシルイソシアネート付加物の水分散体を得
た。Synthesis Example 2 A toluene solution of polyallylamine-octadecyl isocyanate adduct was obtained in the same manner as in Synthesis Example 1 using 10 parts by weight of polyallylamine and 35 parts by weight of octadecyl isocyanate. Nonionic surfactant (polyoxyethylene nonylphenyl ether HLB17.5) 1
Using 0 parts by weight, an aqueous dispersion of polyallylamine-octadecyl isocyanate adduct was obtained in the same manner as in Synthesis Example 1.
実施例１
合成例１の水分散体を水で希釈し、有効成分０６％の塗
布液を調整し、下記の方法で性能試験を行った。結果を
表−１に示す。Example 1 The aqueous dispersion of Synthesis Example 1 was diluted with water to prepare a coating liquid containing 06% of the active ingredient, and a performance test was conducted using the method described below. The results are shown in Table-1.
実施例２
合成例２の水分散体を、１０％のｎ−プロパツールで稀
釈し、有効成分０．６％の塗布液を調整し、下記の方法
で性能試験を行った。結果を表−１に示す。Example 2 The aqueous dispersion of Synthesis Example 2 was diluted with 10% n-propertool to prepare a coating liquid containing 0.6% of the active ingredient, and a performance test was conducted using the method described below. The results are shown in Table-1.
比較例１
市販のトルエン溶剤系のポリエチレンイミン−オクタデ
シルイソイアネート付加物を、トルエンで固形分０．６
％に希釈したものを塗布液とし、下記の方法で性能試験
を行った。結果・を表１に示ず。Comparative Example 1 A commercially available toluene solvent-based polyethyleneimine-octadecyl isocyanate adduct was mixed with toluene to reduce the solid content to 0.6.
% was used as a coating liquid, and a performance test was conducted using the following method. The results are not shown in Table 1.
比較例２
ポリアリルアミンを、１０％のｎ−プロピルアルコール
で固形分０．６％に希釈したものを塗布液とし、下記の
方法で性能試験を行った。Comparative Example 2 Polyallylamine was diluted with 10% n-propyl alcohol to a solid content of 0.6% and used as a coating liquid, and a performance test was conducted in the following manner.
比較例３
ブランクとして、剥離剤を全く塗布していないＯＰＰ、
ＰＥＴフィルム、紙について、下記の試験を行った。Comparative Example 3 As a blank, OPP without any release agent applied,
The following tests were conducted on PET film and paper.
［剥離性能試験法］
上記の塗布液を二軸延伸ポリプロピレン（以後０ＰＰ）
、ポリエチレンテレフタレート（以後ＰＥＴ）フィル
ムのコロナ放電処理面および上質紙に塗布した。このと
きの塗布量は、０．０４ｇ／−に相当する。１００℃で
２分間乾燥した後、塗布面にゴム系粘着テープ（積木化
学製 オリエンチー１）を自重２ｋＪｒのローラで圧着
し、テープの大きさに切断したものを試験片とした。[Peeling performance test method] The above coating solution was applied to biaxially oriented polypropylene (hereinafter referred to as 0PP).
, applied to the corona discharge treated surface of polyethylene terephthalate (hereinafter referred to as PET) film and to high-quality paper. The coating amount at this time corresponds to 0.04 g/-. After drying at 100° C. for 2 minutes, a rubber-based adhesive tape (Orientee 1 manufactured by Block Chemical Co., Ltd.) was pressed onto the coated surface using a roller with a weight of 2 kJr, and the tape was cut into the size of the tape to obtain a test piece.
剥離性能は、上記試験片を６０℃、８５％ＲＨで４日間
保存したものについて、剥離抵抗と、残存粘着力を測定
することにより評価した。剥離抵抗は、剥離速度３００
ｍ／ｎｉｎの９０”剥離時の抵抗として、残存粘着力は
、試料片ののテープを、ステンレスのテストパネルに貼
直し、剥離速度３００＋ｍ／ｌ１ｉｎの１８０°剥離時
の抵抗として測定した。Peeling performance was evaluated by measuring the peeling resistance and residual adhesive strength of the test pieces stored at 60° C. and 85% RH for 4 days. Peeling resistance is peeling speed 300
The residual adhesive strength was measured as the resistance when peeled at 90" m/nin, and the residual adhesive strength was measured by reapplying the tape of the sample piece to a stainless steel test panel, and the resistance when peeled at 180 degrees at a peeling speed of 300+m/l 1 inch.
［稀釈安定性試験］
上記の各水分散体をそれぞれ水で有効成分１重量％に稀
釈し、試験管に入れて２４時間静置後の様子を下記の基
準に基づいて評価した。[Dilution Stability Test] Each of the above aqueous dispersions was diluted with water to 1% by weight of the active ingredient, placed in a test tube and left to stand for 24 hours, and the appearance was evaluated based on the following criteria.
○ ： 全体が均一で、全く変化なし
× ： ２Ｎ分離している
［筆記性試験］
ＯＰＰフィルムの剥離剤塗布面に水性ペンで線を描き下
記の基準に基づいて評価した。○: Overall uniform, no change at all ×: 2N separation [Writability test] Lines were drawn with a water-based pen on the release agent coated surface of the OPP film, and evaluation was made based on the following criteria.
○ ： 筆記できる
× ： はしいて筆記できない
［発明の効果］
本発明の水性剥離剤は、水性でありながら広く一般に用
いられている溶剤系の剥離剤と同等の性能を有し、塗工
性、透明性に優れ、紙やポリエステル、セロファン、Ｏ
ＰＰなとのプラスチックフィルムなどの広範な基材の感
圧粘着テープまたはシートの背面処理等に用いることが
できる。また、溶剤型長鎖アルキル系剥離剤の長所であ
る適度な剥離性を持ち、重ね粘性、筆記性も良好である
。○: Can be written on ×: Cannot be written on [Effects of the Invention] Although the aqueous stripping agent of the present invention is water-based, it has the same performance as a commonly used solvent-based stripping agent, and has excellent coating properties. , excellent transparency, paper, polyester, cellophane, O
It can be used for back surface treatment of pressure-sensitive adhesive tapes or sheets of a wide range of base materials such as PP and plastic films. In addition, it has appropriate release properties, which are the advantages of solvent-type long-chain alkyl release agents, and has good lamination viscosity and writing properties.
Claims (1)
キルイソシアネートを反応させることによって得られる
長鎖アルキルグラフトポリマーを後乳化することによっ
て得られる水分散体を用いることを特徴とする水性剥離
剤。(1) An aqueous release agent characterized by using an aqueous dispersion obtained by post-emulsifying a long-chain alkyl graft polymer obtained by reacting polyvinylamine or polyallylamine with an alkyl isocyanate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1221793A JP2733107B2 (en) | 1989-08-30 | 1989-08-30 | Aqueous release agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1221793A JP2733107B2 (en) | 1989-08-30 | 1989-08-30 | Aqueous release agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0386777A true JPH0386777A (en) | 1991-04-11 |
| JP2733107B2 JP2733107B2 (en) | 1998-03-30 |
Family
ID=16772288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1221793A Expired - Fee Related JP2733107B2 (en) | 1989-08-30 | 1989-08-30 | Aqueous release agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2733107B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5990238A (en) * | 1997-09-19 | 1999-11-23 | 3M Innovative Properties Company | Release coating for adhesive articles and method |
| US6255393B1 (en) | 1998-10-22 | 2001-07-03 | Nippon Shokubai Co., Ltd. | Aqueous polymer dispersion, production process therefor, and aqueous release agent |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5113836A (en) * | 1974-07-25 | 1976-02-03 | Sekisui Chemical Co Ltd | |
| JPS5123491A (en) * | 1974-08-05 | 1976-02-25 | Saiden Kagaku Kk | |
| JPS527883A (en) * | 1975-07-10 | 1977-01-21 | Nitto Electric Ind Co Ltd | Agents with peeling property |
| JPS52151328A (en) * | 1976-06-11 | 1977-12-15 | Nitto Electric Ind Co Ltd | Release agents for pressure-sensitive adhesive tapes |
| JPS5742103A (en) * | 1980-08-26 | 1982-03-09 | Sansui Electric Co | X-y driving device |
| JPS5852396A (en) * | 1981-09-21 | 1983-03-28 | Mitsubishi Chem Ind Ltd | Water-soluble releaser |
-
1989
- 1989-08-30 JP JP1221793A patent/JP2733107B2/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5113836A (en) * | 1974-07-25 | 1976-02-03 | Sekisui Chemical Co Ltd | |
| JPS5123491A (en) * | 1974-08-05 | 1976-02-25 | Saiden Kagaku Kk | |
| JPS527883A (en) * | 1975-07-10 | 1977-01-21 | Nitto Electric Ind Co Ltd | Agents with peeling property |
| JPS52151328A (en) * | 1976-06-11 | 1977-12-15 | Nitto Electric Ind Co Ltd | Release agents for pressure-sensitive adhesive tapes |
| JPS5742103A (en) * | 1980-08-26 | 1982-03-09 | Sansui Electric Co | X-y driving device |
| JPS5852396A (en) * | 1981-09-21 | 1983-03-28 | Mitsubishi Chem Ind Ltd | Water-soluble releaser |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5990238A (en) * | 1997-09-19 | 1999-11-23 | 3M Innovative Properties Company | Release coating for adhesive articles and method |
| US6255393B1 (en) | 1998-10-22 | 2001-07-03 | Nippon Shokubai Co., Ltd. | Aqueous polymer dispersion, production process therefor, and aqueous release agent |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2733107B2 (en) | 1998-03-30 |
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