JPS6116484B2 - - Google Patents
Info
- Publication number
- JPS6116484B2 JPS6116484B2 JP52049082A JP4908277A JPS6116484B2 JP S6116484 B2 JPS6116484 B2 JP S6116484B2 JP 52049082 A JP52049082 A JP 52049082A JP 4908277 A JP4908277 A JP 4908277A JP S6116484 B2 JPS6116484 B2 JP S6116484B2
- Authority
- JP
- Japan
- Prior art keywords
- antifoaming
- antifoaming agent
- industry
- present
- product
- 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
- 239000002518 antifoaming agent Substances 0.000 claims description 16
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000003254 anti-foaming effect Effects 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 230000001804 emulsifying effect Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- -1 glycol monoalkyl ether Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 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
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Degasification And Air Bubble Elimination (AREA)
Description
本発明は各種工業で発生する有害な起泡に対
し、低濃度ですぐれた破泡および抑泡効果を有す
る消泡剤に関する。
消泡剤は合成ゴム工業、合成樹脂工業、製紙工
業、醗酵工業、染料工業、染色工業塗料工業など
に利用されており、一般に鉱物油、パラフイン、
シリコンーン油、金属石けん、脂肪酸、非イオン
界面活性剤あるいはこれらの配合物が知られてい
る。従来の消泡剤はその用途により消泡効果のす
ぐれたものもあるが、反面種々の欠点も有してい
る。とくに問題となる点は、消泡剤自身が水に対
し不溶または溶けにくい性質をもつていることで
ある。そのため、あらかじめ水に分散させて使用
することが多いが、ただ単に分散させている場合
には製品中に混入して種々のトラブルのもととな
る。
これを避けるために、溶剤や乳化剤を使用して
消泡剤を乳化状態で使用する方法もあるが、多く
の場合消泡効果が減少してしまう。この欠点を改
良したものとしては、ポリオキシエチレンポリオ
キシプロピレングリコールのエステル化物を使用
する方法(特公昭45―7973)があるが、乳化性、
消泡性ともにまだ満足できるものではない。
本発明者らは、このような従来の欠点を除去
し、水系で安定なエマルジヨンを形成する自己乳
化型の消泡剤を得るべく検討を重ねた結果、この
目的にかなつた新規な消泡剤を得ることに成功し
た。すなわち本発明は、高級アルコールにプロピ
レンオキシド(以下POと略す)とエチレンオキ
シド(以下EOと略す)とを付加反応させたの
ち、末端水酸基を高級脂肪酸でエステル化させた
両末端に大きな疎水基をもつ化合物(1)を含有する
消泡剤である。
RO(C3H6O)n(C2H4O)oX ……(1)
(ただし、Rは炭素数8〜22のアルキル基また
はアルケニル基;Xは水素またはCOR′,R′は炭
素数7〜21のアルキル基またはアルケニル基;m
は10〜50;nは2〜15であり、エステル化率が50
モル%以上である。)
(1)式の化合物は、通常高級アルコールにPOと
EOとをブロツク付加重合させて得たポリオキシ
アルキレングリコールモノアルキルエーテルを、
高級脂肪酸や高級脂肪酸クロリドを用いて直接エ
ステル化するか、あるいは高級脂肪酸の低級アル
コールエステルを用いてエステル交換反応するこ
とにより合成が可能であり、合成法の違いにより
性能が左右されることはない。
前記一般式(1)で示される化合物において、Rは
炭素数8〜22のアルキル基またはアルケルニル
基、R′は炭素数7〜21のアルキル基またはアル
ケルニル基であるが、この範囲外は好ましくな
い。たとえば炭素数の少ない場合には、界面吸着
力が弱くなつて充分な消泡効果が得られず、炭素
数が多い場合には自己乳化性が悪くなる。
mが10〜50,nが2〜15、さらに脂肪酸による
エステル化率が50モル%以上に限定されるのは、
消泡剤と乳化性が親水基と親油基とのバランスの
影響を受け易く、とくに本発明の自己乳化性を有
する消泡剤は親水基と親油基とが適当にバランス
していることが必要なためである。たとえばmが
50を越えると親油性が大きくなりすぎ、またnが
15を越えると親水性が大きくなりすぎ、いずれの
場合も消泡剤と乳化性が低下する。エステル化率
も50モル%未満では乳化性が悪くなる。
本発明の消泡剤はそのまま使用しても、水に乳
化させて使用しても、さらにケロシン、スピンド
ル油等を混合して水に乳化させて使用しても一向
にさしつかえない。また、広い範囲の水系の用途
に使用可能であり、とくに製紙工業、塗料工業、
染色工業、醗酵工業等の破壊しにくい泡に対して
有効である。
さらに本発明品はすぐれた乳化性を有している
ので、低発泡性乳化剤として使用することも可能
である。
つぎに(1)式化合物の製造例を示す。
製造例 1
115gのオレイルアルコールと、触媒として4
gの苛性力カリとを2オートクレーブにとり、
窒素ガスでシールしたのち、1043gのPOを100〜
150℃、1.0〜7.0Kg/cm2で付加反応する。ついで
113gのEOを同一条件で付加反応したのち充分熟
成する。リン酸で触媒を中和し、真空脱水を行つ
たのち、析出した結晶を別してC18H35O
(C3H6O)42(C2H4O)6H1227gを得た。
つぎに四ツ口フラスコにこの化合物を移し、オ
レイン酸122gと触媒としてのパラトルエンスル
ホン酸4gとを加え、窒素気流下100〜150℃でエ
ステル化反応を行う。反応終了後、触媒をカセイ
カリで中和し、脱水後析出した結晶を別して
C18H35O(C3H6O)42(C2H4O)6COC17H33(エス
テル化率98%)を1295g得た。
製造例 2
四ツ口フラスコに製造例1のPOとEOとの付加
物C18H35O(C3H6O)42(C2H4O)6H1227gとヤシ
油脂肪酸メチルエステル95gと触媒としてナトリ
ウムメチラート5gとをとり、窒素気流下80〜
120℃でエステル交換反応を行つたのちリン酸で
触媒を中和し、脱水後析出した結晶を別して
C18H35O(C3H6O)42(C2H4O)6COR′(R′はヤシ
アルキル基;エステル化率97%)を1280g得た。
つぎに本発明を実施例により説明する。
実施例 1
消泡剤として本発明品および従来品を用いて、
表1の配合でA,B2種の組成のエマルジヨンを
調製した。エマルジヨンは24時間放置し、その状
態を観察した。結果を表2に示すが、本発明品の
乳化安定性は良好である。
The present invention relates to an antifoaming agent that has excellent foam-breaking and foam-suppressing effects at low concentrations against harmful foaming that occurs in various industries. Antifoaming agents are used in the synthetic rubber industry, synthetic resin industry, paper industry, fermentation industry, dye industry, dyeing industry, paint industry, etc., and are generally used in mineral oil, paraffin,
Silicone oils, metallic soaps, fatty acids, nonionic surfactants or combinations thereof are known. Although some conventional antifoaming agents have excellent antifoaming effects depending on their use, they also have various drawbacks. A particular problem is that the antifoaming agent itself is insoluble or poorly soluble in water. Therefore, they are often used after being dispersed in water, but if they are simply dispersed, they may get mixed into the product, causing various problems. In order to avoid this, there is a method of using an antifoaming agent in an emulsified state using a solvent or an emulsifier, but in many cases, the antifoaming effect is reduced. As a method to improve this drawback, there is a method using an esterified product of polyoxyethylene polyoxypropylene glycol (Japanese Patent Publication No. 45-7973), but it has poor emulsifying properties,
Both antifoaming properties are still unsatisfactory. The present inventors have conducted repeated studies to eliminate such conventional drawbacks and to obtain a self-emulsifying antifoaming agent that forms a stable emulsion in an aqueous system, and as a result, have developed a novel antifoaming agent that meets this purpose. succeeded in obtaining. In other words, the present invention involves an addition reaction of propylene oxide (hereinafter abbreviated as PO) and ethylene oxide (hereinafter abbreviated as EO) to a higher alcohol, and then esterifies the terminal hydroxyl group with a higher fatty acid, resulting in a compound having large hydrophobic groups at both ends. This is an antifoaming agent containing compound (1). RO(C 3 H 6 O) n ( C 2 H 4 O) o Alkyl group or alkenyl group having 7 to 21 carbon atoms; m
is 10 to 50; n is 2 to 15, and the esterification rate is 50
It is mol% or more. ) The compound of formula (1) is usually prepared by adding PO to a higher alcohol.
Polyoxyalkylene glycol monoalkyl ether obtained by block addition polymerization with EO,
Synthesis is possible by direct esterification using higher fatty acids or higher fatty acid chlorides, or transesterification using lower alcohol esters of higher fatty acids, and performance is not affected by differences in synthesis methods. . In the compound represented by the general formula (1), R is an alkyl group or alkenyl group having 8 to 22 carbon atoms, and R' is an alkyl group or alkenyl group having 7 to 21 carbon atoms, but outside this range is not preferred. . For example, when the number of carbon atoms is small, the interfacial adsorption force becomes weak and a sufficient antifoaming effect cannot be obtained, and when the number of carbon atoms is large, the self-emulsifying property becomes poor. The reason why m is limited to 10 to 50, n is limited to 2 to 15, and the esterification rate by fatty acid is limited to 50 mol% or more is as follows.
Antifoaming agents and emulsifying properties are easily affected by the balance between hydrophilic groups and lipophilic groups, and in particular, the antifoaming agent having self-emulsifying properties of the present invention must have an appropriate balance of hydrophilic groups and lipophilic groups. This is because it is necessary. For example, m
If it exceeds 50, the lipophilicity becomes too large, and n
When it exceeds 15, the hydrophilicity becomes too large, and in either case, the antifoaming agent and emulsifying properties are reduced. If the esterification rate is less than 50 mol%, the emulsifying property will be poor. The antifoaming agent of the present invention may be used as it is, emulsified in water, or mixed with kerosene, spindle oil, etc. and emulsified in water. It can also be used in a wide range of water-based applications, especially in the paper industry, paint industry,
Effective against difficult-to-destruct foam in the dyeing industry, fermentation industry, etc. Furthermore, since the product of the present invention has excellent emulsifying properties, it can also be used as a low-foaming emulsifier. Next, an example of producing the compound of formula (1) will be shown. Production example 1 115g of oleyl alcohol and 4 as a catalyst
Take 2 g of caustic potash into an autoclave,
After sealing with nitrogen gas, 1043g of PO was
Addition reaction is carried out at 150°C and 1.0-7.0Kg/ cm2 . Then
After addition reaction of 113g of EO under the same conditions, the mixture is sufficiently aged. After neutralizing the catalyst with phosphoric acid and vacuum dehydration, the precipitated crystals were separated and converted to C 18 H 35 O.
1227 g of (C 3 H 6 O) 42 (C 2 H 4 O) 6 H was obtained. Next, this compound is transferred to a four-necked flask, 122 g of oleic acid and 4 g of para-toluenesulfonic acid as a catalyst are added, and an esterification reaction is carried out at 100 to 150° C. under a nitrogen stream. After the reaction is complete, the catalyst is neutralized with caustic potash, and after dehydration, the precipitated crystals are separated.
1295g of C18H35O ( C3H6O ) 42 (C2H4O)6COC17H33 ( esterification rate 98 % ) was obtained. Production Example 2 In a four-necked flask, add 1227 g of the adduct of PO and EO from Production Example 1 C 18 H 35 O (C 3 H 6 O) 42 (C 2 H 4 O) 6 H, 95 g of coconut oil fatty acid methyl ester, and a catalyst. Take 5g of sodium methylate as
After carrying out the transesterification reaction at 120℃, the catalyst was neutralized with phosphoric acid, and after dehydration, the precipitated crystals were separated.
1280 g of C 18 H 35 O(C 3 H 6 O) 42 (C 2 H 4 O) 6 COR′ (R′ is a coconut alkyl group; esterification rate 97%) was obtained. Next, the present invention will be explained by examples. Example 1 Using the product of the present invention and the conventional product as antifoaming agents,
Emulsions having two compositions, A and B, were prepared using the formulations shown in Table 1. The emulsion was left for 24 hours and its condition was observed. The results are shown in Table 2, and the emulsion stability of the product of the present invention is good.
【表】【table】
【表】
実施例 2
本発明品、従来品およびこれらの乳化品A,B
について消泡テストを行つた。底部にボールフイ
ルター(木下式)を設置した1容メスシリンダ
ーに0.005%ロジン石けん水溶液を300ml加える。
各シリンダーを30℃に保ち、ボールフイルターを
通じて毎分3の流量で3時間通気する。消泡剤
は通気開始後泡量が300mlになつた時点で
100ppm(乳化品の場合は消泡剤純分換算)加
え、消泡性(破泡力)を測定し、さらに3時間通
気して持続性(抑泡力)を測定した。
結果を表3に示すが、本発明品は消泡性、持続
性ともすぐれている。[Table] Example 2 Products of the present invention, conventional products, and emulsified products A and B thereof
A defoaming test was conducted on Add 300 ml of 0.005% rosin soap aqueous solution to a 1 volume graduated cylinder equipped with a ball filter (Kinoshita type) at the bottom.
Each cylinder is maintained at 30°C and vented through a ball filter at a flow rate of 3 per minute for 3 hours. Antifoaming agent is added when the foam volume reaches 300ml after the start of aeration.
100 ppm (in the case of an emulsion product, calculated as a pure antifoaming agent) was added to measure the antifoaming property (foam breaking power), and after further aerating for 3 hours, the sustainability (foam suppressing power) was measured. The results are shown in Table 3, and the product of the present invention has excellent antifoaming properties and durability.
Claims (1)
はアルケニル基;Xは水素またはCOR′,R′は炭
素数7〜21のアルキル基またはアルケニル基;m
は10〜50;nは2〜15であり、エステル化率が50
モル%以上である。)[Claims] 1 Antifoaming agent containing the compound of general formula (1) RO (C 3 H 6 O) n (C 2 H 4 O) o X ... (1) (where R is the number of carbon atoms 8-22 alkyl group or alkenyl group; X is hydrogen or COR', R' is a C7-21 alkyl group or alkenyl group; m
is 10 to 50; n is 2 to 15, and the esterification rate is 50
It is mol% or more. )
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4908277A JPS53134785A (en) | 1977-04-30 | 1977-04-30 | Deforming agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4908277A JPS53134785A (en) | 1977-04-30 | 1977-04-30 | Deforming agent |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS53134785A JPS53134785A (en) | 1978-11-24 |
JPS6116484B2 true JPS6116484B2 (en) | 1986-04-30 |
Family
ID=12821163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4908277A Granted JPS53134785A (en) | 1977-04-30 | 1977-04-30 | Deforming agent |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS53134785A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0262189U (en) * | 1988-10-29 | 1990-05-09 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5914338Y2 (en) * | 1979-06-04 | 1984-04-26 | 日産自動車株式会社 | fuel tank |
DE3531212A1 (en) * | 1985-08-31 | 1987-03-05 | Henkel Kgaa | ALKYLENE OXIDE BLOCK POLYMERS TO BE USED AS A DEFOAMER |
IL95029A0 (en) * | 1989-07-12 | 1991-06-10 | Gaf Chemicals Corp | Low viscosity defoaming/antifoaming formulations |
US5045232A (en) * | 1989-07-12 | 1991-09-03 | Rhone-Poulenc Specialty Chemicals, L.P. | Low viscosity defoaming/antiforming formulations |
US6562875B1 (en) * | 2001-08-30 | 2003-05-13 | Ondeo Nalco Company | Aqueous defoamer composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4938923A (en) * | 1972-08-17 | 1974-04-11 | ||
JPS505157A (en) * | 1972-11-24 | 1975-01-20 |
-
1977
- 1977-04-30 JP JP4908277A patent/JPS53134785A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4938923A (en) * | 1972-08-17 | 1974-04-11 | ||
JPS505157A (en) * | 1972-11-24 | 1975-01-20 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0262189U (en) * | 1988-10-29 | 1990-05-09 |
Also Published As
Publication number | Publication date |
---|---|
JPS53134785A (en) | 1978-11-24 |
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