JP2589502B2 - Dye or pigment dispersion method - Google Patents
Dye or pigment dispersion methodInfo
- Publication number
- JP2589502B2 JP2589502B2 JP62208689A JP20868987A JP2589502B2 JP 2589502 B2 JP2589502 B2 JP 2589502B2 JP 62208689 A JP62208689 A JP 62208689A JP 20868987 A JP20868987 A JP 20868987A JP 2589502 B2 JP2589502 B2 JP 2589502B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- surfactant
- ethylene oxide
- group
- dye
- 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 - Fee Related
Links
- 239000000049 pigment Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000006185 dispersion Substances 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000002612 dispersion medium Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 33
- 239000004094 surface-active agent Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- -1 pentadecenyl Chemical group 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000003518 caustics Substances 0.000 description 7
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 230000019635 sulfation Effects 0.000 description 7
- 238000005670 sulfation reaction Methods 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- WVRJUMZHKISIJD-UHFFFAOYSA-N tetraazanium;disulfate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O WVRJUMZHKISIJD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- XDESGXRLUIHEJT-UHFFFAOYSA-N 2,3,4-tribenzylphenol Chemical compound C=1C=CC=CC=1CC1=C(CC=2C=CC=CC=2)C(O)=CC=C1CC1=CC=CC=C1 XDESGXRLUIHEJT-UHFFFAOYSA-N 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- IQGWPPQNIZBTBM-UHFFFAOYSA-N 2-aminoethanol;sulfuric acid Chemical compound NCCO.OS(O)(=O)=O IQGWPPQNIZBTBM-UHFFFAOYSA-N 0.000 description 1
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 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
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Description
【発明の詳細な説明】 従来、界面活性剤は、乳化、分散、洗浄、湿潤、起泡
等の幅広い性能を有しており、それらの諸性能を利用し
て、繊維をはじめとし、紙、ゴミ、プラスチック、金
属、塗料、顔料、土木建築等あらゆる分野に利用されて
いる。特に最近は界面活性剤を使用した末端商品の高性
能化への動きが活発化してきており、それに伴って、界
面活性剤が有する副次的な欠点も指摘されている。DETAILED DESCRIPTION OF THE INVENTION Conventionally, surfactants have a wide range of performances such as emulsification, dispersion, washing, wetting, foaming, and the like. It is used in all fields such as garbage, plastic, metal, paint, pigment, civil engineering and construction. In particular, recently, the trend toward higher performance of terminal products using surfactants has been activated, and with this, secondary disadvantages of surfactants have been pointed out.
例えば、塗料、印刷インキ、接着剤、粘着剤などはそ
の製品の製造時、あるいは製品の安定化、さらには作業
性などの点で欠かすことができないものである。それら
の製品が、塗布、印刷あるいは接着、粘着等の作業で使
用された場合は、界面活性剤は不要であり、むしろ存在
している界面活性剤によって、塗膜、印刷面、接着皮膜
等の耐水性、耐油性等の性能を悪化させる場合が多い。For example, paints, printing inks, adhesives, pressure-sensitive adhesives, and the like are indispensable at the time of manufacturing the product, stabilizing the product, and further, in terms of workability. When these products are used for coating, printing or bonding, sticking, etc., surfactants are unnecessary, and rather, depending on the surfactants present, coatings, printed surfaces, adhesive films, etc. In many cases, performances such as water resistance and oil resistance are deteriorated.
これらの対策として界面活性剤の配合量の削減、界面
活性剤の高分子化等の方向で検討されているが、製品の
安定性、作業性等の点で未だ充分に解決されるまでに至
っていない。As a countermeasure, reductions in the amount of surfactants to be used and polymerization of surfactants are being studied.However, these problems have not yet been sufficiently solved in terms of product stability and workability. Not in.
一方、新しいタイプの界面活性剤の提供として、重合
性、反応性あるいは分解性の界面活性剤の特許が数多く
みられる。On the other hand, there have been many patents for polymerizable, reactive or degradable surfactants for providing new types of surfactants.
例えば、アニオン性の界面活性剤として、特公昭46−
12472号、特開昭54−14431号、特公昭46−34894号、特
公昭56−29657号、特開昭51−30285号、特公昭49−4629
1号、特開昭56−127697号等があり、非イオン性界面活
性剤として、特開昭56−28208号、特開昭50−98484号等
がある。For example, as anionic surfactants,
No. 12472, JP-A-54-14431, JP-B-46-34894, JP-B-56-29657, JP-A-51-30285, JP-B-49-4629
No. 1, JP-A-56-127697 and the like, and as nonionic surfactants, JP-A-56-28208, JP-A-50-98484 and the like.
本発明は、一般式、 〔ただし、上記式中Ｒは炭素数８〜30のアルキル基、ア
ルケニル基、もしくはアルキルアリール基、アラルキル
アリール基、Ａは炭素数２〜４のアルキレン基、もしく
は置換アルキレン基、ｎは０〜100の整数であり、ｍは
１〜200の整数であり、Ｍはアルカリ金属原子、NH4、ア
ルカノールアミン残基である。〕 で表わされる化合物を分散剤として使用し、染料又は顔
料を液体分散媒中に分散することを特徴とする染料又は
顔料の分散方法を提供する。The present invention has the general formula: Wherein R is an alkyl group having 8 to 30 carbon atoms, an alkenyl group, or an alkylaryl group, an aralkylaryl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, and n is 0 to 100. M is an integer of 1 to 200, and M is an alkali metal atom, NH 4 or an alkanolamine residue. ] The compound represented by the formula is used as a dispersant, and a dye or a pigment is dispersed in a liquid dispersion medium.
前記一般式中、Ｒは炭素数８〜30のアルキル基、アル
ケニル基、アルキルアリール基、もしくはアラルキルア
リール基であり、アルキル基としては、例えば、オクチ
ル、ノニル、デシル、ウンデシル、ドデシル、トリデシ
ル、テトラデシル、ペンタデシル、ヘキサデシル、ヘプ
タデシル、オクタデシル、ノナデシル、エイコシル等が
挙げられる。In the general formula, R is an alkyl group having 8 to 30 carbon atoms, an alkenyl group, an alkylaryl group, or an aralkylaryl group. Examples of the alkyl group include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, and tetradecyl. Pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl and the like.
アルケニル基としては、例えば、アクテニル、ノネニ
ル、デセニル、ウンデセニル、ドデセニル、トリデセニ
ル、テトラデセニル、ペンタデセニル、ヘキサデセニ
ル、ヘプタデセニル、オクタデセニル等が挙げられる。Examples of the alkenyl group include actenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl and the like.
アルキルアリール基としては、モノブチルフェノー
ル、ジブチルフェノール、sec−ブチルフェノール、ジs
ec−ブチルフェノール、tert−ブチルフェノール、オク
チルフェノール、ノニルフェノール、ジノニルフェノー
ル、ドデシルフェノール、ジデシルフェノール等が挙げ
られる。Examples of the alkylaryl group include monobutylphenol, dibutylphenol, sec-butylphenol, and di-butylphenol.
Examples include ec-butylphenol, tert-butylphenol, octylphenol, nonylphenol, dinonylphenol, dodecylphenol, didecylphenol and the like.
アラルキルフェノールとしては、スチレン化フェノー
ル、ベンジルフェノール、クミルフェノール等のモノ、
ジ、トリの単独あるいは、これらの混合物等が挙げら
れ、これらのアルキル基等の混合物であってもよい。Examples of aralkyl phenols include styrenated phenols, benzyl phenols, cumyl phenols, and the like.
Di or tri may be used alone or a mixture thereof, and a mixture of these alkyl groups or the like may be used.
また、Ａは炭素数２〜４のアルキレン基または置換ア
ルキレン基であり、例えば、エチレン、プロピレン、ブ
チレン、イソブチレン等であり、それらの単独またはブ
ロックあるいはランダムの混合物であっても良い。A is an alkylene group having 2 to 4 carbon atoms or a substituted alkylene group, for example, ethylene, propylene, butylene, isobutylene, etc., which may be used alone, in a block or in a random mixture.
ｎは０〜100の整数、ｍは１〜200の整数であり、より
好ましくはｎは０または１〜50、ｍは２〜100の範囲で
ある。n is an integer of 0 to 100, m is an integer of 1 to 200, more preferably n is 0 or 1 to 50, and m is in the range of 2 to 100.
さらに、本発明の染料顔料分散剤は工業的に容易に製
造できるものであり、例えば次のようにして製造するこ
とができる。すなわち、ノニルフェノールまたはラウリ
ルアルコールを原料とし、要すればアルキレンオキサイ
ドを付加し、アリルグリシジルエーテルを触媒存在下の
もとで加熱反応し、得られた反応組成物に、さらに、ア
ルキレンオキサイドを常法にて付加させる。次に硫酸、
スルファミン酸等の硫酸化剤にて硫酸化を行い、必要に
より塩基性物質で中和することにより得ることができ
る。Furthermore, the dye / pigment dispersant of the present invention can be easily produced industrially, and can be produced, for example, as follows. That is, nonylphenol or lauryl alcohol is used as a raw material, alkylene oxide is added if necessary, and allyl glycidyl ether is heated and reacted in the presence of a catalyst, and the resulting reaction composition is further treated with alkylene oxide in a conventional manner. To add. Then sulfuric acid,
It can be obtained by performing sulfation with a sulfating agent such as sulfamic acid and, if necessary, neutralizing with a basic substance.
以下、本発明を実施例により、具体的に説明するが、
本発明はこれらに限定されるものではない。（％，部と
あるは重量基準を示す。） 製造例１ 撹拌機、温度計、還流管を備えた反応容器にノニルフ
ェノール220g（1.0モル）、触媒としてトリエチルアミ
ン1.5gを仕込み、つぎにアリルグルシジルエーテル114g
（1.0モル）を滴下し100℃にて５時間撹拌した。Hereinafter, the present invention will be described specifically with reference to Examples.
The present invention is not limited to these. Production Example 1 220 g (1.0 mol) of nonylphenol and 1.5 g of triethylamine as a catalyst were charged into a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, and then allyl glucidyl was prepared. 114 g of ether
(1.0 mol) was added dropwise and stirred at 100 ° C. for 5 hours.
次に、得られた反応組成物をオートクレーブに移し、
苛性カリウムを触媒として、圧力1.5kg/cm2、温度130℃
の条件にてエチレンオキサイドを反応組成物に対して、
10モル、30モル、100モル付加して組成物を得た。次
に、撹拌機、温度計を備えた反応容器に上記反応組成物
のエチレンオキサイド10モル付加体387g（0.5モル）、
スルファミン酸58.2g（0.6モル）を仕込み、120℃に昇
温し、３時間撹拌反応し、硫酸化を行った。未反応スル
ファミン酸をロ別除去して得られた組成物を、本発明界
面活性剤〔Ａ〕とした。同様の操作にて得られたエチレ
ンオキサイド30モル付加体の硫酸エステルアンモニウム
塩を、本発明界面活性剤〔Ｂ〕、エチレンオキサイド10
0モル付加体の硫酸エステルアンモニムウ塩を、本発明
界面活性剤〔Ｃ〕とした。Next, the obtained reaction composition was transferred to an autoclave,
Pressure 1.5kg / cm 2 , temperature 130 ° C using caustic potassium as catalyst
Under the conditions of ethylene oxide to the reaction composition,
The composition was obtained by adding 10, 30 and 100 moles. Next, 387 g (0.5 mol) of a 10 mol ethylene oxide adduct of the above reaction composition was placed in a reaction vessel equipped with a stirrer and a thermometer.
58.2 g (0.6 mol) of sulfamic acid was charged, the temperature was raised to 120 ° C., and the mixture was stirred and reacted for 3 hours to perform sulfation. The composition obtained by removing unreacted sulfamic acid by filtration was used as the surfactant [A] of the present invention. The sulfated ammonium salt of a 30 mol ethylene oxide adduct obtained by the same operation was used as the surfactant [B] of the present invention, ethylene oxide 10
The 0 mol adduct sulfate ammonium salt was used as the surfactant [C] of the present invention.
製造例２ 撹拌機、温度計、還流管を備えた反応容器にラウリル
アルコール186g（1.0モル）、触媒として三弗化ホウ素
エーテル錯体0.6gを仕込み、次にアリルグルシジルエー
テル228g（2.0モル）を滴下し、80℃にて５時間撹拌し
た後に120℃に加温し、減圧にて過剰のアリルグリシジ
ルエーテルを除去した。次に、得られた反応組成物をオ
ートクレーブに移し、苛性カリウムを触媒として、圧力
1.5kg/cm2、温度130℃の条件にてエチレンオキサイドを
反応組成物に対して、５モル、20モル、50モル付加して
得られた組成物を製造例１に準じて硫酸化を行い、得ら
れたエチレンオキサイド５モル付加体の硫酸エステルア
ンモニウム塩を、本発明界面活性剤〔Ｄ〕、エチレンオ
キサイド20モル付加体の硫酸エステルアンモニウム塩
を、本発明界面活性剤〔Ｅ〕、エチレンオキサイド50モ
ル付加体の硫酸エステルアンモニウム塩を、本発明界面
活性剤〔Ｆ〕とした。Production Example 2 A reaction vessel equipped with a stirrer, a thermometer and a reflux tube was charged with 186 g (1.0 mol) of lauryl alcohol, 0.6 g of a boron trifluoride ether complex as a catalyst, and then 228 g (2.0 mol) of allyl glucidyl ether. After dropwise addition and stirring at 80 ° C. for 5 hours, the mixture was heated to 120 ° C., and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and pressure was adjusted using caustic potassium as a catalyst.
A composition obtained by adding 5 mol, 20 mol, and 50 mol of ethylene oxide to the reaction composition under the conditions of 1.5 kg / cm 2 and a temperature of 130 ° C. was subjected to sulfation according to Production Example 1. The resulting ammonium sulfate sulfate of a 5 mol ethylene oxide adduct was treated with the surfactant [D] of the present invention, the ammonium sulfate sulfate of a 20 mol adduct of ethylene oxide was treated with the surfactant [E] of the present invention, ethylene oxide The 50 mol adduct ammonium sulfate salt was used as the surfactant [F] of the present invention.
製造例３ 撹拌機、温度計、還流管を備えた反応容器にジスチレ
ン化フェノールエチレンオキサイド10モル・プロピレン
オキサイド２モルブロック付加体856g（1.0モル）、触
媒として三弗化ホウ素エーテル錯体2gを仕込み、次にア
リルグリシジルエーテル228g（2.0モル）を滴下し、80
℃にて５時間撹拌した後に120℃に加温し、減圧にて過
剰のアリルグリシジルエーテルを除去した。次に、得ら
れた反応組成物をオートクレーブに移し、苛性カリウム
を触媒として、圧力1.5kg/cm2、温度130℃の条件にてエ
チレンオキサイドを反応組成物に対して15モル、40モル
付加して得られた組成物を製造例１に準じて硫酸化を行
い、得られたエチレンオキサイド15モル付加体の硫酸エ
ステルアンモニウム塩を、本発明界面活性剤〔Ｇ〕、エ
チレンオキサイド40モル付加体の硫酸エステルアンモニ
ウム塩を、本発明界面活性剤〔Ｈ〕とした。Production Example 3 A reaction vessel equipped with a stirrer, a thermometer, and a reflux tube was charged with 856 g (1.0 mol) of a distyrenated phenolethylene oxide 10 mol / propylene oxide 2 mol block adduct and a boron trifluoride ether complex 2 g as a catalyst. Next, 228 g (2.0 mol) of allyl glycidyl ether was added dropwise,
After stirring at 5 ° C for 5 hours, the mixture was heated to 120 ° C and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and using caustic potassium as a catalyst, 15 mol and 40 mol of ethylene oxide were added to the reaction composition under the conditions of a pressure of 1.5 kg / cm 2 and a temperature of 130 ° C. The resulting composition was sulfated according to Production Example 1, and the resulting sulfate ammonium salt of the ethylene oxide 15 mol adduct was converted to the surfactant [G] of the present invention and 40 mol of the ethylene oxide adduct. The ammonium sulfate salt was used as the surfactant [H] of the present invention.
製造例４ 撹拌機、温度計、還流管を備えた反応容器にオレイル
アルコールエチレンオキサイド30モル付加体1588g（1.0
モル）、触媒として三弗化ホウ素エーテル錯体3gを仕込
み、次にアリルグリシジルエーテル228g（2.0モル）を
滴下し、80℃にて５時間撹拌した後に120℃に加温し、
減圧にて過剰のアリルグリシジルエーテルを除去した。
次に得られた反応組成物をオートクレーブに移し、苛性
カリウム触媒として、圧力1.5kg/cm2、温度130℃の条件
にてエチレンオキサイド40モル、プロピレンオキサイド
10モルを反応組成物に対してランダムに付加して得られ
た組成物を、製造例１に準じてスルファミン酸を用いて
硫酸化を行い、得られた硫酸化物にスルファミン酸と当
量の苛性ソーダを加え、脱アンモニアを行い、得られた
硫酸エステルナトリウム塩を、本発明界面活性剤〔Ｉ〕
とした。Production Example 4 A reaction vessel equipped with a stirrer, a thermometer, and a reflux tube was charged with 1588 g of an oleyl alcohol ethylene oxide 30 mol adduct (1.0 g).
Mol), 3 g of boron trifluoride etherate complex was charged as a catalyst, and 228 g (2.0 mol) of allyl glycidyl ether was added dropwise. After stirring at 80 ° C. for 5 hours, the mixture was heated to 120 ° C.
Excess allyl glycidyl ether was removed under reduced pressure.
Next, the obtained reaction composition was transferred to an autoclave, and as a caustic potassium catalyst, at a pressure of 1.5 kg / cm 2 and a temperature of 130 ° C., 40 mol of ethylene oxide and propylene oxide were used.
A composition obtained by randomly adding 10 moles to the reaction composition is subjected to sulfation using sulfamic acid according to Production Example 1, and the obtained sulfated product is added with sulfamic acid and an equivalent amount of caustic soda. In addition, deammonification was performed, and the obtained sulfate sodium salt was used as the surfactant [I] of the present invention.
And
製造例５ 撹拌機、温度計、還流管を備えた反応容器にステアリ
ルアルコールプロピレンオキサイド２モル付加体385g
（1.0モル）、触媒として三弗化ホウ素エーテル錯体1.5
gを仕込み、次にアリルグリシジルエーテル228g（2.0モ
ル）を滴下し、80℃にて５時間撹拌した後に120℃に加
温し、減圧にて過剰のアリルグリシジルエーテルを除去
した。次に得られた反応組成物をオートクレーブに移
し、苛性カリウム触媒として、圧力1.5kg/cm2、温度130
℃の条件にてエチレンオキサイドを２モル、５モル付加
して得られた組成物を製造例１に準じて、スルファミン
酸を用いて硫酸化を行い、得られた硫酸化物にスルファ
ミン酸と当量のモノエタノールアミンを加え、脱アンモ
ニアを行い、得られたエチレンオキサイド２モル付加体
の硫酸エステルモノエタノールアミン塩を、本発明界面
活性剤〔Ｊ〕、エチレンオキサイド５モル付加体の硫酸
エステルモノエタノールアミン塩を、本発明界面活性剤
〔Ｋ〕とした。Production Example 5 385 g of a 2 mol stearyl alcohol propylene oxide adduct was placed in a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube.
(1.0 mol), boron trifluoride ether complex 1.5 as catalyst
Then, 228 g (2.0 mol) of allyl glycidyl ether was added dropwise, and the mixture was stirred at 80 ° C. for 5 hours, heated to 120 ° C., and the excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and as a caustic potassium catalyst, the pressure was 1.5 kg / cm 2 , and the temperature was 130 ° C.
The composition obtained by adding 2 mol and 5 mol of ethylene oxide under the condition of ° C. was subjected to sulfation using sulfamic acid in accordance with Production Example 1, and the obtained sulfate was equivalent to sulfamic acid in an equivalent amount. Monoethanolamine was added and deammonification was performed. The resulting sulfate monoethanolamine salt of the ethylene oxide 2 mol adduct was converted to the surfactant [J] of the present invention, and the sulfate monoesteramine of the ethylene oxide 5 mol adduct. The salt was designated as the surfactant [K] of the present invention.
製造例６ 撹拌機、温度計、還流管を備えた反応容器にジsec−
ブチルフェノールブチレンオキサイド３モル付加体278g
（1.0モル）、触媒として三弗化ホウ素エーテル錯体1g
を仕込み、次にアリルグリシジルエーテル228g（2.0モ
ル）を滴下し、80℃にて５時間撹拌した後に120℃に加
温し、減圧にて過剰のアリルグリシジルエーテルを除去
した。次に得られた反応組成物をオートクレーブに移
し、苛性カリウム触媒として、圧力1.5kg/cm2、温度130
℃の条件にて、プロピレンオキサイド２モル、エチレン
オキサイド15モルを反応組成物に対して付加し、得られ
た組成物を製造例１に準じて硫酸化を行い、得られた硫
酸エステルアンモニウム塩を、本発明界面活性剤〔Ｌ〕
とした。Production Example 6 In a reaction vessel equipped with a stirrer, thermometer and reflux tube,
278 g of 3 mol butylphenol butylene oxide adduct
(1.0 mol), 1 g of boron trifluoride etherate complex as catalyst
Then, 228 g (2.0 mol) of allyl glycidyl ether was added dropwise, and the mixture was stirred at 80 ° C. for 5 hours, then heated to 120 ° C., and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, and as a caustic potassium catalyst, the pressure was 1.5 kg / cm 2 , and the temperature was 130 ° C.
Under the condition of 2 ° C., 2 mol of propylene oxide and 15 mol of ethylene oxide were added to the reaction composition, and the resulting composition was subjected to sulfation according to Production Example 1. The surfactant of the present invention [L]
And
製造例７ 撹拌機、温度計、還流管を備えた反応容器にトリベン
ジルフェノールエチレンオキサイド20モル付加体1244g
（1.0モル）、触媒として三弗化ホウ素エーテル錯体4g
を仕込み、次にアリルグリシジルエーテル228g（2.0モ
ル）を滴下し、80℃にて５時間撹拌した後に120℃に加
温し、減圧にて過剰のアリルグリシジルエーテルを除去
した。次に得られた反応組成物をオートクレーブに移
し、苛性カリウムを触媒として、圧力1.5kg/cm2、温度1
30℃の条件にて、プロピレンオキサイドを反応組成物に
対して５モル付加し、得られた組成物を、製造例１に準
じて硫酸化を行い、得られた硫酸エステルアンモニウム
塩を、本発明界面活性剤〔Ｍ〕とした。Production Example 7 In a reaction vessel equipped with a stirrer, a thermometer, and a reflux tube, 1244 g of a 20-mol adduct of tribenzylphenol ethylene oxide was added.
(1.0 mol), 4 g of boron trifluoride etherate complex as catalyst
Then, 228 g (2.0 mol) of allyl glycidyl ether was added dropwise, and the mixture was stirred at 80 ° C. for 5 hours, then heated to 120 ° C., and excess allyl glycidyl ether was removed under reduced pressure. Next, the obtained reaction composition was transferred to an autoclave, using caustic potassium as a catalyst, at a pressure of 1.5 kg / cm 2 and a temperature of 1
At 30 ° C., 5 mol of propylene oxide was added to the reaction composition, and the resulting composition was subjected to sulfation in accordance with Production Example 1. The surfactant [M] was used.
実施例１ 製造例１ないし７で得られた本発明の界面活性剤
〔Ａ〕〜〔Ｍ〕について、その水溶液の表面張力を測定
した。なお、比較品として従来の界面活性剤の表面張力
も併せて示した。（表面張力はトラウベ法にて測定し
た。）その結果を第１表に示した。Example 1 The surface tensions of the aqueous solutions of the surfactants [A] to [M] of the present invention obtained in Production Examples 1 to 7 were measured. The surface tension of a conventional surfactant is also shown as a comparative product. (The surface tension was measured by the Traube method.) The results are shown in Table 1.
実施例２ 第２表に示す本発明の界面活性剤について、カーボン
ブラックの分散性能およびトルエンの乳化性能を測定し
た。なお、比較品として従来の界面活性剤の性能も同様
に測定した。その結果を第２表に示した。Example 2 For the surfactants of the present invention shown in Table 2, the dispersion performance of carbon black and the emulsification performance of toluene were measured. In addition, the performance of the conventional surfactant was similarly measured as a comparative product. The results are shown in Table 2.
分散性能試験方法 容器100mlの共栓付メスシリンダーに界面活性剤1g、
カーボンブラック10gを入れ、水にて溶解分散させ100ml
に調節した。Dispersion performance test method 1 g of surfactant in a 100 ml graduated cylinder with a stopper
Add 10g of carbon black, dissolve and disperse in water 100ml
Was adjusted to
次に、そのメスシリンダーを１分間に100回震盪し、
１時間25℃にて静置した。その後、液上面から30cc抜き
取りグラスフィルターにてロ過した後、105℃にて乾燥
させ、グラスフィルター上の残渣の重量より分散性を次
式により測定した。Next, shake the measuring cylinder 100 times a minute,
It was left at 25 ° C. for 1 hour. Thereafter, 30 cc was withdrawn from the upper surface of the liquid, filtered, and dried at 105 ° C., and the dispersibility was measured from the weight of the residue on the glass filter by the following formula.
乳化性能試験方法 容量20mlの目盛付き共栓試験管に0.5％界面活性剤水
溶液5mlとケロシン5mlを加え、１分間に100回震盪した
後、１時間25℃にて静置した。その後、乳化層の容積
（ml）を測定し、乳化性を次式により測定した。 Emulsification performance test method 5 ml of a 0.5% aqueous surfactant solution and 5 ml of kerosene were added to a 20-ml graduated stoppered stoppered test tube, shaken 100 times per minute, and then allowed to stand at 25 ° C for 1 hour. Thereafter, the volume (ml) of the emulsified layer was measured, and the emulsifiability was measured by the following equation.
Claims (1)
ルケニル基、もしくはアルキルアリール基、アラルキル
アリール基、Ａは炭素数２〜４のアルキレン基、もしく
は置換アルキレン基、ｎは０〜100の整数であり、ｍは
１〜200の整数であり、Ｍはアルカリ金属原子、NH4、ア
ルカノールアミン残基である。）で表わされる化合物を
分散剤として使用し、染料又は顔料を液体分散媒中に分
散することを特徴とする染料又は顔料の分散方法。(1) a general formula, Wherein R is an alkyl group having 8 to 30 carbon atoms, an alkenyl group, or an alkylaryl group, an aralkylaryl group, A is an alkylene group having 2 to 4 carbon atoms, or a substituted alkylene group, and n is 0 to 100. M is an integer of 1 to 200, and M is an alkali metal atom, NH 4 or an alkanolamine residue. A method for dispersing a dye or pigment, comprising using the compound represented by the formula (1) as a dispersant and dispersing the dye or pigment in a liquid dispersion medium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62208689A JP2589502B2 (en) | 1987-08-21 | 1987-08-21 | Dye or pigment dispersion method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62208689A JP2589502B2 (en) | 1987-08-21 | 1987-08-21 | Dye or pigment dispersion method |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61118956A Division JPS6354928A (en) | 1986-05-07 | 1986-05-22 | Novel surfactant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63199271A JPS63199271A (en) | 1988-08-17 |
| JP2589502B2 true JP2589502B2 (en) | 1997-03-12 |
Family
ID=16560443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62208689A Expired - Fee Related JP2589502B2 (en) | 1987-08-21 | 1987-08-21 | Dye or pigment dispersion method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2589502B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101611099B (en) * | 2007-02-14 | 2013-01-02 | 大日精化工业株式会社 | Dispersing agent for organic pigment and use thereof |
| JP5215785B2 (en) * | 2008-01-25 | 2013-06-19 | 大日精化工業株式会社 | Coupler, dye, method for producing the dye, colorant using the dye, and coloring method |
| JP5215782B2 (en) * | 2008-08-11 | 2013-06-19 | 大日精化工業株式会社 | Organic pigment dispersant and use thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0468013A (en) * | 1990-07-09 | 1992-03-03 | Mitsui Toatsu Chem Inc | Resin composition for injection molding and production of molding therefrom |
-
1987
- 1987-08-21 JP JP62208689A patent/JP2589502B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0468013A (en) * | 1990-07-09 | 1992-03-03 | Mitsui Toatsu Chem Inc | Resin composition for injection molding and production of molding therefrom |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63199271A (en) | 1988-08-17 |
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