JPH0515762A - Dispersant composition - Google Patents
Dispersant compositionInfo
- Publication number
- JPH0515762A JPH0515762A JP3202479A JP20247991A JPH0515762A JP H0515762 A JPH0515762 A JP H0515762A JP 3202479 A JP3202479 A JP 3202479A JP 20247991 A JP20247991 A JP 20247991A JP H0515762 A JPH0515762 A JP H0515762A
- Authority
- JP
- Japan
- Prior art keywords
- dispersant
- unsaturated
- acid
- sulfonic acid
- carbon atoms
- 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.)
- Pending
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- -1 sulfonate compound Chemical class 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000001336 alkenes Chemical class 0.000 claims abstract description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 239000004793 Polystyrene Substances 0.000 abstract description 5
- 229920002223 polystyrene Polymers 0.000 abstract description 5
- 239000002245 particle Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 239000007859 condensation product Substances 0.000 abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 2
- 230000003252 repetitive effect Effects 0.000 abstract 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000004568 cement Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- URGSMJLDEFDWNX-UHFFFAOYSA-N 1-butylnaphthalene Chemical compound C1=CC=C2C(CCCC)=CC=CC2=C1 URGSMJLDEFDWNX-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910017840 NH 3 Inorganic materials 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000011398 Portland cement Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 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
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 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
- 239000002994 raw material Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は分散剤組成物に関するも
のであり、詳しくはセメント用分散剤、染料分散剤、顔
料分散剤、乳化重合用分散剤、スケール分散剤等の水系
分散に有効な組成物に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dispersant composition, and more particularly, it is effective for aqueous dispersion of a dispersant for cement, a dye dispersant, a pigment dispersant, an emulsion polymerization dispersant, a scale dispersant and the like. It relates to a composition.
【0002】[0002]
【従来技術】固体粒子を水に分散させる技術は各種の産
業分野で要求されている。通常粒子の分散性を向上させ
る目的で分散剤が使用されている。2. Description of the Related Art A technique for dispersing solid particles in water is required in various industrial fields. Usually, a dispersant is used for the purpose of improving the dispersibility of particles.
【0003】例えば、コンクリートにおいてはセメント
粒子の水への分散を向上させるために分散剤が使用され
ている。同様に、染料や顔料の分散や乳化重合系の分散
安定化、水処理におけるスケールの防止にも分散剤が使
用されており、各分野で有用な働きを示している。For example, in concrete, a dispersant is used to improve the dispersion of cement particles in water. Similarly, dispersants are used for dispersion of dyes and pigments, dispersion stabilization of emulsion polymerization systems, and prevention of scale in water treatment, and they have useful functions in various fields.
【0004】従来、これらの分散剤としてはポリ(メ
タ)アクリル酸塩やこれらの共重合体の塩、無水マレイ
ン酸に代表される不飽和ジカルボン酸の共重合体の塩、
あるいはナフタレンスルホン酸塩の縮合物、ポリスチレ
ンスルホン酸塩、リグニンスルホン酸塩、脂肪族ジエン
の(共)重合体のスルホン酸塩、アルキレンオキシド鎖
を有するビニルモノマーの共重合体等が使用されてい
る。Conventionally, as these dispersants, salts of poly (meth) acrylic acid salts and copolymers thereof, salts of copolymers of unsaturated dicarboxylic acids represented by maleic anhydride,
Alternatively, a naphthalene sulfonate condensate, a polystyrene sulfonate, a lignin sulfonate, a sulfonate of a (co) polymer of an aliphatic diene, a copolymer of a vinyl monomer having an alkylene oxide chain, or the like is used. ..
【0005】又、特開平1−115445号には分散剤
組成物として、ナフタレンとスチレン・マレイン酸共重
合体のスルホン化物をホルマリン縮合したものが有効で
あることが記載されている。Further, Japanese Patent Laid-Open No. 1-115445 discloses that a dispersant composition which is obtained by formalin-condensing a sulfonated product of naphthalene and a styrene-maleic acid copolymer is effective.
【0006】[0006]
【発明が解決しようとする問題点】しかし、従来の分散
剤は相応の効果を有するものの、実用性の観点からは、
使用量が多かったり、分散性が不足していたり、不充分
であった。However, although the conventional dispersants have a corresponding effect, from the viewpoint of practicality,
The amount used was large, the dispersibility was insufficient, and it was insufficient.
【0007】[0007]
【問題を解決するための手段】この発明はこのような従
来の問題点に着目してなされたものである。すなわち、
本発明は、ナフタレンスルホン酸および/またはアルキ
ルナフタレンスルホン酸と下記の(I)式で示されるく
り返し単位からなるポリマーのスルホン化物のうちから
選択される1または2以上の化合物とのアルデヒド縮合
物、又はその塩を必須成分として含有することを特徴と
する分散剤組成物に関する。The present invention has been made by paying attention to such conventional problems. That is,
The present invention relates to an aldehyde condensate of naphthalene sulfonic acid and / or alkyl naphthalene sulfonic acid and one or more compounds selected from the sulfonated products of polymers consisting of repeating units represented by the following formula (I): Alternatively, it relates to a dispersant composition containing a salt thereof as an essential component.
【0008】[0008]
【化2】 [Chemical 2]
【0009】ただし、Rは水素又は炭素数1〜4のアル
キル基、 Aは(1)炭素数2〜18のオレフィン (2)炭素数2〜18の不飽和モノカルボン酸 (3)不飽和カルボン酸エステル (4)アルキレンオキシド付加エチレン性不飽和モノマ
ー (5)炭素数2〜18の不飽和スルホン酸 (6)炭素数2〜18の不飽和アルコール の中から選ばれる1種以上のモノマー m,nは整数であり、m/n=10/0〜1/9であ
る。However, R is hydrogen or an alkyl group having 1 to 4 carbon atoms, A is (1) an olefin having 2 to 18 carbon atoms, (2) an unsaturated monocarboxylic acid having 2 to 18 carbon atoms, and (3) an unsaturated carboxylic acid. Acid ester (4) alkylene oxide addition ethylenically unsaturated monomer (5) unsaturated sulfonic acid having 2 to 18 carbon atoms (6) unsaturated alcohol having 2 to 18 carbon atoms m, n is an integer, and m / n = 10/0 to 1/9.
【0010】(アルキル)ナフタレンとしてはナフタレ
ン、メチルナフタレン、ブチルナフタレン等が使用され
る。アルキル基としては炭素数1〜5のものが好まし
い。As the (alkyl) naphthalene, naphthalene, methylnaphthalene, butylnaphthalene and the like are used. The alkyl group preferably has 1 to 5 carbon atoms.
【0011】式(I)で示されるくり返し単位からなる
ポリマー(以下本ポリマーという)としては、具体的に
はポリスチレン、およびスチレンや炭素1〜4のアルキ
ル基を有するアルキルスチレンと他のビニルモノマーの
共重合物が挙げられる。Specific examples of the polymer having repeating units represented by the formula (I) (hereinafter referred to as the present polymer) include polystyrene, styrene and alkylstyrene having an alkyl group having 1 to 4 carbon atoms, and other vinyl monomers. Examples thereof include copolymers.
【0012】他のビニルモノマーとしては、エチレン、
プロピレン、イソブチレン、ブタジエン、イソプレン等
の炭素数2〜18のオレフィン類、アクリル酸、メタク
リル酸等の炭素数2〜18の不飽和モノカルボン酸類、
アクリル酸エチル、メタクリル酸メチル、マレイン酸モ
ノブチルエステル、イタコン酸ジエチルエステル等の不
飽和カルボン酸エステル類、エチレンオキシド、プロピ
レンオキシド、ブチレンオキシド、α−オレフィンエポ
キシド等が付加されたアリルアルコール、アクリル酸、
マレイン酸、アクリルアミド等のアルキレンオキシド付
加ビニルモノマー類、エチレンスルホン酸、アリルスル
ホン酸等の炭素数2〜18の不飽和スルホン酸類、アリ
ルアルコール等の炭素数2〜18の不飽和アルコール類
が挙げられ、この中の1種以上のモノマーが共重合に供
される。Other vinyl monomers include ethylene,
C2-C18 olefins such as propylene, isobutylene, butadiene and isoprene; C2-C18 unsaturated monocarboxylic acids such as acrylic acid and methacrylic acid;
Ethyl acrylate, methyl methacrylate, maleic acid monobutyl ester, unsaturated carboxylic acid esters such as itaconic acid diethyl ester, ethylene oxide, propylene oxide, butylene oxide, α-olefin epoxide and the like allyl alcohol, acrylic acid,
Examples include alkylene oxide-added vinyl monomers such as maleic acid and acrylamide, unsaturated sulfonic acids having 2 to 18 carbon atoms such as ethylene sulfonic acid and allyl sulfonic acid, and unsaturated alcohols having 2 to 18 carbon atoms such as allyl alcohol. , One or more of these monomers are subjected to copolymerization.
【0013】本ポリマーにおけるスチレン骨格を有する
ビニルモノマーと他のビニルモノマーの組成比は10/
0〜1/9(モル比)であり、分子量は重量平均分子量
で1000〜50万、好ましくは2000〜10万であ
る。The composition ratio of the vinyl monomer having a styrene skeleton to the other vinyl monomer in the present polymer is 10 /
It is 0 to 1/9 (molar ratio), and the molecular weight is 1,000 to 500,000, preferably 2,000 to 100,000 in terms of weight average molecular weight.
【0014】スルホン化剤としては、硫酸、発煙硫酸、
無水硫酸、クロル硫酸を用いるが、本ポリマーのスルホ
ン化物は、本ポリマーをスルホン化剤にてスルホン化し
てもよいし、重合原料として、スチレンスルホン酸等の
予め、スルホン化されたモノマーを使用して、重合して
もよい。As the sulfonating agent, sulfuric acid, fuming sulfuric acid,
Sulfuric anhydride and chlorosulfuric acid are used, but the sulfonated product of this polymer may be sulfonated with a sulfonating agent, or a sulfonated monomer such as styrene sulfonic acid may be used as a polymerization raw material. And polymerize.
【0015】縮合反応に用いるアルデヒドとしては、ホ
ルムアルデヒド、アセトアルデヒド、ブチルアルデヒド
等が挙げられるが、ホルムアルデヒドが一般的である。Examples of the aldehyde used in the condensation reaction include formaldehyde, acetaldehyde, butyraldehyde, and formaldehyde is common.
【0016】中和塩としては、Na,K等のアルカリ金
属塩、Ca,Mg等のアルカリ土類金属塩、NH3 ,ア
ミン等が挙げられる。Examples of the neutralizing salt include alkali metal salts such as Na and K, alkaline earth metal salts such as Ca and Mg, NH 3 and amine.
【0017】本発明の組成物において、(アルキル)ナ
フタレンと本ポリマーの組成比は9/1〜1/9(重量
比)が好適である。In the composition of the present invention, the composition ratio of (alkyl) naphthalene to the present polymer is preferably 9/1 to 1/9 (weight ratio).
【0018】[0018]
【発明の効果】この分散剤組成物は重合と縮合の両反応
によって、今までにない新規な構造を形成せしめたもの
で、セメント用分散剤、染料分散剤、顔料分散剤、乳化
重合用分散剤、スケール分散剤等の水系分散剤として、
極く少量で、優れた効果を発揮することができる。This dispersant composition has a novel structure which has never been seen by both polymerization and condensation reactions. It is a dispersant for cement, a dye dispersant, a pigment dispersant, and an emulsion polymerization dispersion. As an aqueous dispersant such as an agent, a scale dispersant,
A very small amount can exert an excellent effect.
【0019】[0019]
【実施例】次に実施例を挙げて、この発明を詳細に説明
するが、本発明はこれらの実施例に限定されるものでは
ない。EXAMPLES The present invention will now be described in detail with reference to examples, but the present invention is not limited to these examples.
【0020】(1)組成物1の製造 2リットルの4ツ口フラスコに攪拌棒、温度計、コンデ
ンサーをセットし、濃硫酸245g(2.5モル)を仕
込んだ。続いてポリスチレン(Mw5000)を104
g(1モル)仕込み、100℃で1時間反応した。その
後ナフタレンを128g(1モル)仕込み、150℃で
1時間反応した。次いで、90℃まで冷却し水140g
とホルムアルデヒドの37%水溶液81g(1モル)を
加え、100℃で5時間縮合反応を行った。縮合反応終
了後80℃に冷却し、水600gとNaOH80g(2
モル)とCa(OH)2 37g(0.5モル)を加え、
中和した後、ロ過によって、無機塩を除去し、目的物を
得た。(1) Preparation of Composition 1 A stirring bar, a thermometer, and a condenser were set in a 2-liter four-necked flask, and 245 g (2.5 mol) of concentrated sulfuric acid was charged. Then, add polystyrene (Mw5000) 104
g (1 mol) was charged, and the mixture was reacted at 100 ° C. for 1 hour. After that, 128 g (1 mol) of naphthalene was charged and reacted at 150 ° C. for 1 hour. Then cool to 90 ° C and 140g
And 81 g (1 mol) of a 37% aqueous solution of formaldehyde were added, and a condensation reaction was carried out at 100 ° C. for 5 hours. After completion of the condensation reaction, the mixture was cooled to 80 ° C., 600 g of water and 80 g of NaOH (2
Mol) and 37 g (0.5 mol) of Ca (OH) 2 are added,
After neutralization, the inorganic salt was removed by filtration to obtain the desired product.
【0021】(2)組成物2〜6の製造 組成物1と同様にして表1に示す組成物を得た。ただ
し、ポリスチレンに変えて(B)項に示すポリマーを使
用した。ポリマーとナフタレンの仕込みモル比は(C)
項に示す。またホルムアルデヒドの仕込み量は、ナフタ
レンと同モルとした。(2) Production of Compositions 2 to 6 In the same manner as Composition 1, the compositions shown in Table 1 were obtained. However, the polymer shown in the item (B) was used instead of polystyrene. The charge molar ratio of polymer and naphthalene is (C)
It shows in the section. The amount of formaldehyde charged was the same as that of naphthalene.
【0022】(3)比較例1〜3 比較例1は組成物のポリスチレンをスチレン・マレイン
酸共重合物に変えて製造した。表1に示す。比較例2,
3はナフタレンスルホン酸ホルマリン縮合物Na塩とポ
リスチレンスルホン酸Naを用いた。(3) Comparative Examples 1 to 3 Comparative Example 1 was produced by changing the polystyrene of the composition to a styrene / maleic acid copolymer. It shows in Table 1. Comparative Example 2,
No. 3 used a naphthalene sulfonic acid formalin condensate Na salt and polystyrene sulfonic acid Na.
【0023】[0023]
【表1】 [Table 1]
【0024】(4)コンクリートの調整と評価 セメント(日本セメント(株)製、普通ポルトランドセ
メント)457kg/m3 、細骨材(淀川産 川砂 比
重2.58)619kg/m3 、粗骨材(鞍馬産 砕石
比重2.67)1170kg/m3 、水160kg/
m3 および本発明品あるいは比較品を0.5重量%(セ
メントに対する固型分換算)を強制ミキサーにより攪拌
混合して、コンクリートを調整した。このコンクリート
の空気量、スランプ量および硬化後の圧縮強度を測定し
た。結果を表2に示す。(4) Preparation and evaluation of concrete Cement (manufactured by Nippon Cement Co., Ltd., ordinary Portland cement) 457 kg / m 3 , fine aggregate (Yodogawa produced river sand specific gravity 2.58) 619 kg / m 3 , coarse aggregate ( Kurama crushed stone, specific gravity 2.67) 1170 kg / m 3 , water 160 kg /
0.5 wt% of m 3 and the product of the present invention or the comparative product (calculated as solid content relative to cement) were mixed by stirring with a forced mixer to prepare concrete. The air content, slump content, and compressive strength after curing of this concrete were measured. The results are shown in Table 2.
【0025】[0025]
【表2】 [Table 2]
【0026】本発明例は比較例に比べ、スランプが大き
く分散性に優れている。The example of the present invention has a large slump and is excellent in dispersibility as compared with the comparative example.
【0027】(5)無機顔料スラリーの調整と評価 酸化チタン(石原産業(株)製、R−820)70g、
水30gおよび本発明品あるいは比較品0.5重量%
(酸化チタンに対する固型分換算)を容器に採り、25
℃で1分間攪拌混合した後、B型粘度計にて粘度を測定
した。結果を表3に示す。(5) Preparation and Evaluation of Inorganic Pigment Slurry 70 g of titanium oxide (R-820 manufactured by Ishihara Sangyo Co., Ltd.),
30 g of water and 0.5% by weight of the product of the present invention or comparative product
(Titanium oxide solid content conversion) is put in a container and
After stirring and mixing at 0 ° C. for 1 minute, the viscosity was measured with a B-type viscometer. The results are shown in Table 3.
【0028】[0028]
【表3】 [Table 3]
【0029】本発明例は比較例に比べ粘度が低く、分散
性に優れている。The inventive examples have lower viscosities and superior dispersibility than the comparative examples.
フロントページの続き (72)発明者 杉山 浩 京都府長岡京市友岡1丁目17−6Front page continuation (72) Inventor Hiroshi Sugiyama 1-17-6 Tomooka, Nagaokakyo, Kyoto Prefecture
Claims (1)
キルナフタレンスルホン酸と下記の(I)式で示される
くり返し単位からなるポリマーのスルホン化物のうちか
ら選択される1または2以上の化合物とのアルデヒド縮
合物、又はその塩を必須成分として含有することを特徴
とする分散剤組成物。 【化1】 ただし、Rは水素又は炭素数1〜4のアルキル基、 Aは(1)炭素数2〜18のオレフィン (2)炭素数2〜18の不飽和モノカルボン酸 (3)不飽和カルボン酸エステル (4)アルキレンオキシド付加エチレン性不飽和モノマ
ー (5)炭素数2〜18の不飽和スルホン酸 (6)炭素数2〜18の不飽和アルコール の中から選ばれる1種以上のモノマー m,nは整数であり、m/n=10/0〜1/9であ
る。Claims: 1. A sulfonated polymer of naphthalene sulfonic acid and / or alkyl naphthalene sulfonic acid and a polymer of repeating units represented by the following formula (I). A dispersant composition comprising an aldehyde condensate with a compound or a salt thereof as an essential component. [Chemical 1] However, R is hydrogen or a C1-C4 alkyl group, A is (1) C2-C18 olefin (2) C2-C18 unsaturated monocarboxylic acid (3) unsaturated carboxylic acid ester ( 4) Alkylene oxide-added ethylenically unsaturated monomer (5) Unsaturated sulfonic acid having 2 to 18 carbon atoms (6) One or more monomers m and n selected from unsaturated alcohols having 2 to 18 carbon atoms are integers. And m / n = 10/0 to 1/9.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3202479A JPH0515762A (en) | 1991-07-16 | 1991-07-16 | Dispersant composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3202479A JPH0515762A (en) | 1991-07-16 | 1991-07-16 | Dispersant composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0515762A true JPH0515762A (en) | 1993-01-26 |
Family
ID=16458197
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3202479A Pending JPH0515762A (en) | 1991-07-16 | 1991-07-16 | Dispersant composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0515762A (en) |
-
1991
- 1991-07-16 JP JP3202479A patent/JPH0515762A/en active Pending
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