JP6164424B2 - 水溶性高分子顔料分散剤及び水溶性高分子顔料分散剤を含有する水系組成物 - Google Patents
水溶性高分子顔料分散剤及び水溶性高分子顔料分散剤を含有する水系組成物 Download PDFInfo
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- JP6164424B2 JP6164424B2 JP2014011025A JP2014011025A JP6164424B2 JP 6164424 B2 JP6164424 B2 JP 6164424B2 JP 2014011025 A JP2014011025 A JP 2014011025A JP 2014011025 A JP2014011025 A JP 2014011025A JP 6164424 B2 JP6164424 B2 JP 6164424B2
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- water
- soluble polymer
- pigment dispersant
- polymer pigment
- pigment
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
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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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- 239000001257 hydrogen Substances 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- UBHHTPOLMACCDD-UHFFFAOYSA-N n,n-dimethyl-4-phenylbut-3-en-1-amine Chemical compound CN(C)CCC=CC1=CC=CC=C1 UBHHTPOLMACCDD-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
Description
撹拌装置、温度計、還流冷却管、および窒素導入管を備えた反応容器に、スチレン18部(単量体の総重量和の17.7重量%、以下同様)、メタクリル酸メチル18部(17.7重量%)、メタクリル酸24.1部(メタクリル酸ナトリウムに換算すると29.8重量%)、スチレンスルホン酸ナトリウム11.1部(10.9重量%)、ポリオキシエチレンノニルプロペニルフェニルエーテル硫酸アンモニウム(アニオン性乳化剤:商品名「アクアロンHS−1025」,第一工業製薬(株)製、固形分25%)24.1部(23.8重量%)、過硫酸アンモニウム0.4部、α−メチルスチレンダイマー0.6部及び水338部を混合・加熱し、80℃で5時間反応を行い共重合体の水溶液を得た。その後冷却し、60℃でメタクリル酸の100%を中和する水酸化ナトリウムを加えて1時間攪拌して、重量平均分子量10000、25℃における粘度が100mPa・s、色調が1ガードナーの共重合体の20重量%水溶液(水溶性高分子顔料分散剤1)を得た。得られた水溶性高分子顔料分散剤1の分析は次の方法によって実施した。結果を表1に示す。
重量平均分子量は、得られた水溶性高分子顔料分散剤をゲルパーミエーションクロマトグラフィー(東ソー(株)製、商品名「HLC−8320」、カラム:東ソー(株)製、商品名「TSK−GEL GMPWXL」および「TSK−GEL G2500PWXL」を連結)により測定し、ポリエチレンオキシド換算により求めた。
JIS K 7117−2に準拠し、B型粘度計を用いて25℃において測定した。
JIS K 0071−2に準拠しガードナー単位で測定した。
製造例1で得た水溶性高分子顔料分散剤1を4部及びカーボン顔料(三菱化学製 三菱カーボンブラックMA−100)6部に水17.6部及びガラスビーズ19.3部を加えペイントシェーカーにて1時間、分散を行った。分散工程の後、金網を使用してガラスビーズを除き、分散剤の添加量が11.8%(対顔料 固形分換算(%))の水系組成物1を得た。水溶性高分子顔料分散剤1を8部及びカーボン顔料(三菱化学製 三菱カーボンブラックMA−100)6部に水13.6部及びガラスビーズ19.3部を加えペイントシェーカーにて1時間、分散を行った。分散工程の後、金網を使用してガラスビーズを除き、分散剤の添加量が21.1%(対顔料 固形分換算(%))の水系組成物1を得た。
得られた水系組成物1の25℃における粘度を上述した方法で測定した。粘度が低いほど、ハンドリング性が良好であることを示す。結果を表3に示す。
(平均粒子径)
得られた水系組成物1中の表面に水溶性高分子顔料分散剤が吸着した顔料粒子の平均粒子径も測定した。平均粒子径は、レーザー回折・散乱法による粒子径測定装置LASER SCATTERING PARTICLE SIZE DISTRIBUTION ANALYZER LA−910(HORIBA製)で測定した。粒子径が小さいほど、分散性良好なことを示す。結果を表3に示す。
(塗膜の耐水性)
得られた水系組成物1を使用した塗料塗膜の耐水性についても試験した。耐水性は得られた水系組成物1をスチレンアクリル共重合体エマルジョンに混合し、No.6のバーコーターにてガラス板に塗工、30分常温にて乾燥後、105℃にて30分乾燥させたものを40℃の水に浸漬し24時間後の白化度を目視にて観察し、とても良いから、とても悪いの順に○、○−、△、△−、×、××、と判定した。結果を表3に示す。
ディスコートN−14(第一工業製薬製特殊ポリカルボン酸塩)を2.68部及びカーボン顔料(三菱化学製 三菱カーボンブラックMA−100)6部に水18.9部及びガラスビーズ19.3部を加えペイントシェーカーにて1時間、分散を行った。分散工程の後、金網を使用してガラスビーズを除き、分散剤の添加量が11.8%(対顔料 固形分換算(%))の水系組成物25を得た。ディスコートN−14を5.35部及びカーボン顔料(三菱化学製 三菱カーボンブラックMA−100)6部に水16.3部及びガラスビーズ19.3部を加えペイントシェーカーにて1時間、分散を行った。分散工程の後、金網を使用してガラスビーズを除き、分散剤の添加量が21.1%(対顔料 固形分換算(%))の水系組成物25を得た。この水系組成物25の粘度、粒子径、耐水性を実施例1と同様に測定した。結果を表3に示す。
Claims (7)
- スチレン(A)、炭素数1〜10のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体(B)、一般式(1)で表わされる単量体(C)、一般式(2)で表わされる単量体(D)、及び一般式(3)で表わされる単量体(E)を必須構成成分とする共重合体を含有することを特徴とする水溶性高分子顔料分散剤。
- 上記単量体(C)がアルカリ金属塩である請求項1記載の水溶性高分子顔料分散剤。
- 上記共重合体におけるスチレン(A)と、炭素数1〜10のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体(B)の合計含有量が20〜65重量%である請求項1又は2記載の水溶性高分子顔料分散剤。
- 上記共重合体の20重量%水溶液における25℃での粘度が75〜2000mPa・sである請求項1〜3のいずれかに記載の水溶性高分子顔料分散剤。
- 上記共重合体の20重量%水溶液における色調が1ガードナー以下である請求項1〜4のいずれかに記載の水溶性高分子顔料分散剤。
- 上記共重合体の重量平均分子量が7500〜20000である請求項1〜5のいずれかに記載の水溶性高分子顔料分散剤。
- 水性溶媒中に、請求項1〜6のいずれかに記載の水溶性高分子顔料分散剤と色素を含有する水系組成物。
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