JPH0341486B2 - - Google Patents
Info
- Publication number
- JPH0341486B2 JPH0341486B2 JP8057582A JP8057582A JPH0341486B2 JP H0341486 B2 JPH0341486 B2 JP H0341486B2 JP 8057582 A JP8057582 A JP 8057582A JP 8057582 A JP8057582 A JP 8057582A JP H0341486 B2 JPH0341486 B2 JP H0341486B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrylate
- resin dispersion
- dispersion
- aqueous
- aqueous resin
- 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
Links
- 239000011347 resin Substances 0.000 claims description 27
- 229920005989 resin Polymers 0.000 claims description 27
- 239000006185 dispersion Substances 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 7
- 239000003125 aqueous solvent Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 239000004831 Hot glue Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- KZUIKPMQAIEBOE-UHFFFAOYSA-N 2-(ethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCNCCOC(=O)C(C)=C KZUIKPMQAIEBOE-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-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
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-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
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- PZDUWXKXFAIFOR-UHFFFAOYSA-N hexadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C=C PZDUWXKXFAIFOR-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 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
- 239000000203 mixture Substances 0.000 description 1
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- -1 pentaacrylate Chemical compound 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は電子写真液体現像剤、塗料、インキ、
ホツトメルト接着剤等に有用な非水系樹脂分散液
及びその製造方法に関する。
電子写真液体現像剤、塗料、インキ、接着剤等
に用いられる非水系樹脂分散液及びその製造方法
についてはこれまで種々提案がなされている。例
えば米国特許第4087393号明細書には脂肪族炭化
水素よりなる非水溶媒中で(a)一般式
（ＲはＨ又は−CH3、ｎは８〜20の整数）
で示されるモノマー（重合後、非水溶媒に溶媒和
するモノマー）をグリシジルアクリレート、グリ
シジルメタクリレート等のグリシジル基を有する
モノマーと共重合せしめる工程、(b)得られた共重
合体をアクリル酸、メタクリル酸、イタコン酸、
マレイン酸等のカルボキシル基を有するモノマー
でエステル化する工程、及び(c)得られたエステル
化共重合体にスチレン、メチルメタクリレート、
酢酸ビニル等のビニルモノマー（重合後、非水溶
媒に不溶となるモノマー）をグラフト化する工程
を連続的に行なうことにより非水系樹脂分散液を
製造する方法が開示されている。
しかしこの方法はグリシジル基によるカルボキ
シル基のエステル化率が、長時間かけても10〜20
％と低いため、グラフト化効率が悪い上、分散液
については(1)樹脂の粒径が大きく、しかも不均一
であるため、分散安定姓が悪く、沈降したり、経
時によりゲル化を起こす、(2)顔料に対する分散安
定性が悪いため、塗料用として用いた場合は経時
により顔料の凝集が生じるし、また柔軟性及び耐
水性のある塗膜を形成することができない等の欠
点を有している。
本発明の第一の目的は反応性の良いオレフイン
系共重合体を使用することにより、グラフト化効
率を高めた非水系樹脂分散液の製造方法を提供す
ることである。
本発明の第二の目的は、上記のようにして得ら
れた分散安定性を向上した非水系樹脂分散液を提
供することである。
本発明の第三の目的は顔料に対する分散性を向
上することにより、顔料の凝集を防止すると共に
柔軟性及び耐水性のある塗膜を形成できる非水系
樹脂分散液を提供することである。
本発明の第四の目的はホツトメルト可能で、従
つてホツトメルト接着剤として特に有用な樹脂を
含む非水系樹脂分散液を提供することである。
本発明の非水系樹脂分散液の製造方法は次の通
りである。
本発明による非水系樹脂分散液の製造方法は脂
肪族炭化水素を主体とする非水溶媒中、重合開始
剤の存在下で一般式
（但しＸはハロゲン、ｘ、ｙは繰返し単位、ｍは
１〜20の整数）
で示されるオレフイン系共重合体に一般式
（但しＹはＨ又はCH3基、ｎは６〜20の整数）で
示される長鎖アクリル系モノマーをグラフト化さ
せることを特徴とするものである。
一般式のオレフイン系共重合体は脂肪族炭化
水素に不溶で、得られる樹脂の定着性及びホツト
メルト性に寄与する成分である。このようなオレ
フイン系共重合体の具体例としては下記のものが
挙げられる。
The present invention relates to electrophotographic liquid developers, paints, inks,
This invention relates to a nonaqueous resin dispersion useful for hot melt adhesives and the like, and a method for producing the same. Various proposals have been made regarding non-aqueous resin dispersions used in electrophotographic liquid developers, paints, inks, adhesives, etc., and methods for producing the same. For example, US Pat. No. 4,087,393 discloses that (a) the general formula (R is H or -CH 3 , n is an integer of 8 to 20) A monomer represented by (a monomer that is solvated in a non-aqueous solvent after polymerization) is copolymerized with a monomer having a glycidyl group such as glycidyl acrylate or glycidyl methacrylate. (b) The obtained copolymer is mixed with acrylic acid, methacrylic acid, itaconic acid,
A step of esterifying with a monomer having a carboxyl group such as maleic acid, and (c) adding styrene, methyl methacrylate to the obtained esterified copolymer,
A method for producing a non-aqueous resin dispersion by continuously performing a step of grafting a vinyl monomer such as vinyl acetate (a monomer that becomes insoluble in a non-aqueous solvent after polymerization) is disclosed. However, with this method, the esterification rate of carboxyl groups by glycidyl groups is only 10 to 20, even over a long period of time.
%, the grafting efficiency is poor, and as for the dispersion, (1) the particle size of the resin is large and non-uniform, so the dispersion stability is poor, causing sedimentation and gelation over time; (2) Due to the poor dispersion stability of pigments, when used as paints, pigments tend to aggregate over time, and there are disadvantages such as the inability to form a flexible and water-resistant coating. ing. The first object of the present invention is to provide a method for producing a non-aqueous resin dispersion with improved grafting efficiency by using a highly reactive olefin copolymer. A second object of the present invention is to provide a non-aqueous resin dispersion with improved dispersion stability obtained as described above. A third object of the present invention is to provide a non-aqueous resin dispersion that can prevent pigment agglomeration and form a flexible and water-resistant coating film by improving the dispersibility of pigments. A fourth object of the present invention is to provide a nonaqueous resin dispersion containing a resin that is hot meltable and thus particularly useful as a hot melt adhesive. The method for producing the non-aqueous resin dispersion of the present invention is as follows. The method for producing a non-aqueous resin dispersion according to the present invention is to produce a non-aqueous resin dispersion using the general formula (However, X is a halogen, x and y are repeating units, and m is an integer from 1 to 20.) (However, Y is H or a CH 3 group, and n is an integer of 6 to 20.) It is characterized by grafting a long chain acrylic monomer. The olefin copolymer of the general formula is a component that is insoluble in aliphatic hydrocarbons and contributes to the fixing properties and hot melt properties of the resulting resin. Specific examples of such olefin copolymers include the following.
【表】【table】
【表】
次に一般式の長鎖アクリル系モノマーは重合
後、脂肪族炭化水素と溶媒和し、得られる樹脂の
分散性及び定着性に寄与する成分である。このよ
うな長鎖アクリル系モノマーの具体例としてはヘ
キシルメタクリレート、ラウリルメタクリレー
ト、ラウリルアクリレート、ノニルアクリレー
ト、デシルメタクリレート、ドデシルメタクリレ
ート、ドデシルアクリレート、セチルメタクリレ
ート、セチルアクリレート、ステアリルアクリレ
ート、ステアリルメタクリレート等が挙げられ
る。
なお本発明では顔料への吸着及び顔料の分散
性、保存性を高めるために、他の重合性不飽和モ
ノマーを併用することができる。この種のモノマ
ーの具体例としてはメチルメタクリレート、メチ
ルアクリレート、エチルアクリレート、エチルメ
タクリレート、ブチルメタクリレート、ブチルア
クリレート、プロピルアクリレート、プロピルメ
タクリレート、ペンタアクリレート、２−エチル
ヘキシルメタクリレート、２−エチルアミノエチ
ルメタクリレート、２−エチルアミノエチルメタ
クリレート、スチレン、ビニルトルエン、酢酸ビ
ニル、メタクリル酸、アクリル酸、イタコン酸、
ビニルピロリドン、ビニルピリジン等が挙げられ
る。
また非水溶媒として用いられる脂肪族炭化水素
としてはｎ−ヘキサン、イソオクタン、イソドデ
カン、ｎ−ノナン等があり、市販品ではエツソ社
製アイソパーＧ、Ｈ、Ｌ、Ｍやシエル石油製シエ
ルゾール71がある。その他、ハロゲン化脂肪族炭
化水素、芳香族炭化水素等の他の非水溶媒を併用
することができる。
重合開始剤としては過酸化ベンゾイル、過酸化
ラウロイル、ジ−ｔ−ブチルパーオキサイド等の
有機過酸化物や、アゾイソブチロニトリルのよう
なアゾ化合物等の通常のものが使用できる。
以上のような材料を用いて本発明方法を実施す
るには通常は脂肪族炭化水素を主体とする非水溶
媒中、重合開始剤の存在下に一般式のオレフイ
ン系共重合体と一般式の長鎖アクリル系モノマ
ーと必要あれば他の重合性不飽和モノマーと60〜
130℃でグラフト共重合反応させればよい。或い
は別法として非水溶媒の不存在下に前記温度でグ
ラフト共重合反応させ、得られた樹脂を非水溶媒
中に分散させてもよい。ここで長鎖アクリル系モ
ノマー及び他の重合性不飽和モノマーの使用量は
夫々オレフイン系共重合体１重量部に対し0.3〜
10重量部、0.01〜２重量部が適当である。
こうして得られる非水系樹脂分散液中の樹脂は
微細且つ均一で、しかも非水溶媒中で一部溶媒和
し、一部不溶解なので、分散安定性が良く、また
定着性、ホツトメルト性、顔料に対する分散性も
優れているので、本発明の分散液は特に電子写真
現像剤、ホツトメルト接着剤用として有用であ
る。
以下に本発明の実施例を示す。
実施例 １
１容の四つ口フラスコにイソオクタン200ｇ
を採り、オイルバス上で90℃に加熱した後、この
中にNo.A2のオレフイン系共重合体50ｇ、ステア
リルメタクリレート50ｇ及びベンゾイルパーオキ
サイド５ｇを加え、前記温度で５時間加熱し、重
合率96％で液粘度68cp（20℃）、樹脂粒径0.3〜
0.8μの乳白色非水系樹脂分散液を得た。
実施例 ２
実施例１で用いたフラスコにアイソパーG200
ｇを採り、オイルバス上で90℃に加熱した後、こ
の中にNo.A4のオレフイン系共重合体30ｇを加え、
溶解した。更にこの中にメタクリル酸３ｇ、ノニ
ルメタクリレート60ｇ及びイソブチロニトリル３
ｇの混合液を２時間に亘つて滴下、グラフト共重
合させ、重合率96％で液粘度58cp（20℃）、樹脂
粒径0.2〜0.4μの乳白色非水系樹脂分散液を得た。
実施例 ３
実施例１で用いたフラスコにNo.B4のオレフイ
ン系共重合体50ｇを採り、100℃に加熱溶融させ
た。この中にセチルメタクリレート50ｇ、フマル
酸１ｇ及びベンゾイルパーオキサイド３ｇを加
え、前記温度で３時間グラフト共重合させ、重合
率93％で樹脂を得た。次にこの樹脂をアイソパー
G100ｇ中に分散して液粘度120cp（20℃）、樹脂粒
径１〜3μの乳白色非水系樹脂分散液を得た。
以上のようにして得られた実施例１〜３の分散
液を50℃で30日間保存し、粒子の沈降を調べた
が、いずれも沈降は認められなかつた。
実施例 ４〜12
表−１に示した材料及び製造方法で非水系樹脂
分散液を製造した。その結果は表−２の通りであ
る。[Table] Next, the long-chain acrylic monomer of the general formula is a component that solvates with aliphatic hydrocarbons after polymerization and contributes to the dispersibility and fixing properties of the resulting resin. Specific examples of such long-chain acrylic monomers include hexyl methacrylate, lauryl methacrylate, lauryl acrylate, nonyl acrylate, decyl methacrylate, dodecyl methacrylate, dodecyl acrylate, cetyl methacrylate, cetyl acrylate, stearyl acrylate, stearyl methacrylate, and the like. In the present invention, other polymerizable unsaturated monomers can be used in combination to improve adsorption to the pigment, dispersibility, and storage stability of the pigment. Specific examples of monomers of this type include methyl methacrylate, methyl acrylate, ethyl acrylate, ethyl methacrylate, butyl methacrylate, butyl acrylate, propyl acrylate, propyl methacrylate, pentaacrylate, 2-ethylhexyl methacrylate, 2-ethylaminoethyl methacrylate, 2- Ethylaminoethyl methacrylate, styrene, vinyltoluene, vinyl acetate, methacrylic acid, acrylic acid, itaconic acid,
Examples include vinylpyrrolidone and vinylpyridine. In addition, aliphatic hydrocarbons used as non-aqueous solvents include n-hexane, isooctane, isododecane, n-nonane, etc. Commercially available products include Isopar G, H, L, M manufactured by Etsuso and Ciel Sol 71 manufactured by Ciel Oil. . In addition, other non-aqueous solvents such as halogenated aliphatic hydrocarbons and aromatic hydrocarbons can be used in combination. As the polymerization initiator, conventional ones such as organic peroxides such as benzoyl peroxide, lauroyl peroxide, and di-t-butyl peroxide, and azo compounds such as azoisobutyronitrile can be used. To carry out the method of the present invention using the above-mentioned materials, the olefinic copolymer of the general formula and the general formula of 60~ with long chain acrylic monomer and other polymerizable unsaturated monomers if necessary
The graft copolymerization reaction may be carried out at 130°C. Alternatively, the graft copolymerization reaction may be carried out at the above temperature in the absence of a non-aqueous solvent, and the resulting resin may be dispersed in the non-aqueous solvent. Here, the amount of long-chain acrylic monomer and other polymerizable unsaturated monomer used is 0.3 to 1 part by weight of the olefin copolymer, respectively.
10 parts by weight, 0.01 to 2 parts by weight is suitable. The resin in the non-aqueous resin dispersion obtained in this way is fine and uniform, and is partially solvated and partially insoluble in the non-aqueous solvent, so it has good dispersion stability, and also has good fixing properties, hot melt properties, and pigment resistance. Since the dispersibility is also excellent, the dispersion of the present invention is particularly useful for electrophotographic developers and hot melt adhesives. Examples of the present invention are shown below. Example 1 200 g of isooctane in a 1-volume four-necked flask
After heating to 90°C on an oil bath, 50 g of No. A2 olefin copolymer, 50 g of stearyl methacrylate, and 5 g of benzoyl peroxide were added thereto, and the mixture was heated at the above temperature for 5 hours until the polymerization rate was 96. %, liquid viscosity 68cp (20℃), resin particle size 0.3~
A milky white non-aqueous resin dispersion of 0.8μ was obtained. Example 2 Isopar G200 was added to the flask used in Example 1.
After heating it to 90℃ on an oil bath, add 30g of No.A4 olefin copolymer to it.
Dissolved. Furthermore, 3 g of methacrylic acid, 60 g of nonyl methacrylate, and 3 g of isobutyronitrile are contained in this.
g was added dropwise over 2 hours to carry out graft copolymerization to obtain a milky white non-aqueous resin dispersion having a polymerization rate of 96%, a liquid viscosity of 58 cp (at 20 DEG C.), and a resin particle size of 0.2 to 0.4 .mu.m. Example 3 50 g of No. B4 olefin copolymer was placed in the flask used in Example 1, and heated and melted at 100°C. 50 g of cetyl methacrylate, 1 g of fumaric acid and 3 g of benzoyl peroxide were added to this, and graft copolymerization was carried out at the above temperature for 3 hours to obtain a resin with a polymerization rate of 93%. Next, apply this resin to isopar.
A milky white non-aqueous resin dispersion having a liquid viscosity of 120 cp (20° C.) and a resin particle size of 1 to 3 μm was obtained by dispersing it in 100 g of G. The dispersions of Examples 1 to 3 obtained as described above were stored at 50° C. for 30 days and the sedimentation of particles was examined, but no sedimentation was observed in any of them. Examples 4 to 12 Non-aqueous resin dispersions were manufactured using the materials and manufacturing methods shown in Table-1. The results are shown in Table-2.
【表】【table】
【表】【table】
【表】【table】
Claims (1)
合開始剤の存在下で一般式 （但しＸはハロゲン、ｘ、ｙは繰返し単位、ｍは
１〜２の整数） で示されるオレフイン系共重合体に一般式 （但しＹはＨ又はCH3基、ｎは６〜20の整数） で示される長鎖アクリル系モノマーをグラフト化
させることを特徴とする非水系樹脂分散液の製造
方法。[Scope of Claims] 1. In a nonaqueous solvent mainly composed of aliphatic hydrocarbons, in the presence of a polymerization initiator, the general formula (However, X is a halogen, x and y are repeating units, and m is an integer of 1 to 2.) (However, Y is H or CH 3 group, and n is an integer of 6 to 20.) A method for producing a non-aqueous resin dispersion characterized by grafting a long-chain acrylic monomer represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8057582A JPS58196220A (en) | 1982-05-12 | 1982-05-12 | Nonaqueous type resin dispersion and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8057582A JPS58196220A (en) | 1982-05-12 | 1982-05-12 | Nonaqueous type resin dispersion and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58196220A JPS58196220A (en) | 1983-11-15 |
| JPH0341486B2 true JPH0341486B2 (en) | 1991-06-24 |
Family
ID=13722132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8057582A Granted JPS58196220A (en) | 1982-05-12 | 1982-05-12 | Nonaqueous type resin dispersion and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58196220A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1245847B (en) * | 1990-11-13 | 1994-10-25 | Himont Inc | FUNCTIONALIZED POLYMERS OF ALPHA OLEFINS. |
| DK1195594T3 (en) | 2000-10-02 | 2010-05-10 | Mallinckrodt Baker B V | Use of an improved mounting medium for slides |
-
1982
- 1982-05-12 JP JP8057582A patent/JPS58196220A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58196220A (en) | 1983-11-15 |
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