CN105664786A - Anionic tallol gemini surfactant and preparation method thereof - Google Patents
Anionic tallol gemini surfactant and preparation method thereof Download PDFInfo
- Publication number
- CN105664786A CN105664786A CN201610000744.2A CN201610000744A CN105664786A CN 105664786 A CN105664786 A CN 105664786A CN 201610000744 A CN201610000744 A CN 201610000744A CN 105664786 A CN105664786 A CN 105664786A
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- CN
- China
- Prior art keywords
- yatall
- anionic
- active agent
- surface active
- tallol
- 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.)
- Granted
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 54
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 239000003784 tall oil Substances 0.000 title abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000001291 vacuum drying Methods 0.000 claims abstract description 8
- 238000005576 amination reaction Methods 0.000 claims description 42
- 239000012043 crude product Substances 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 16
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 14
- 238000000746 purification Methods 0.000 claims description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- -1 ketone diamines Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 150000004985 diamines Chemical class 0.000 abstract 2
- POLIXZIAIMAECK-UHFFFAOYSA-N 4-[2-(2,6-dioxomorpholin-4-yl)ethyl]morpholine-2,6-dione Chemical compound C1C(=O)OC(=O)CN1CCN1CC(=O)OC(=O)C1 POLIXZIAIMAECK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006065 biodegradation reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 231100000956 nontoxicity Toxicity 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003265 pulping liquor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
The invention relates to an anionic tallol gemini surfactant and a preparation method thereof. The method comprises the following steps: mixing and reacting tallol with a diamine substance to prepare a crude aminated tallol product; washing the crude aminated tallol product to remove the unreacted diamine substance, and carrying out vacuum drying to obtain aminated tallol; dissolving ethylenediamine tetraacetic acid dianhydride and the prepared aminated tallol in a solvent methanol, and stirring and reacting to obtain a crude anionic tallol gemini surfactant; and neutralizing and reacting the crude anionic tallol gemini surfactant with an aqueous solution of NaOH to generate a sodium salt in order to obtain the anionic tallol gemini surfactant. The novel anionic tallol gemini surfactant is synthesized in the invention, and has the advantages of high surface activity, environmental protection, non-toxicity, easy biodegradation and good application prospect.
Description
Technical field
The present invention relates to a kind of tensio-active agent, it is specifically related to a kind of anionic Yatall MA Gemini surface active agent and its preparation method.
Background technology
In recent years, along with the demand of social production and the enhancing of people's environmental consciousness, the high-performance of tensio-active agent and greenization development are the focuses always paid close attention to both at home and abroad. Yatall MA is the transliteration of TallOil, Yatall MA is also known as liquid rosin, it is obtain from dark solution remaining during alkali method (being mainly sulphate process) wood pulp processed, Yatall MA type tensio-active agent not only has good surfactivity, and it is natural plant grease, there is readily biodegradable, to human temperature and, the characteristic of environmentally safe, therefore the synthesis and property research of Yatall MA tensio-active agent receives in recent years and pays close attention to widely.
Summary of the invention
It is an object of the invention to provide a kind of anionic Yatall MA Gemini surface active agent and its preparation method, adopt the Yatall MA extracted in spent pulping liquor to be raw material, synthesize Gemini surface active agent nontoxic, readily biodegradable.
The technical solution adopted in the present invention is:
The preparation method of anionic Yatall MA Gemini surface active agent, it is characterised in that:
Comprise the following steps:
Step one: the preparation of amination Yatall MA crude product:
Be 1:(1 ~ 5 by mol ratio) Yatall MA and the mixing of two amine substances, react at 140 ~ 180 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Be 1:(2 ~ 6 by mol ratio) ethylenediamine tetraacetic acid (EDTA) two acid anhydride and obtained amination Yatall MA be dissolved in solvent methanol, stirring reaction 5 ~ 10h at 40 ~ 80 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
In step one, two amine substances are selected from quadrol, different fluorine that ketone diamines, urea, phenylenediamine.
The tensio-active agent that preparation method such as described anionic Yatall MA Gemini surface active agent obtains.
The present invention has the following advantages:
The present invention has synthesized a kind of novel anionic Yatall MA Gemini surface active agent, has higher surfactivity and environment friendly, and nontoxic, readily biodegradable, has a good application prospect.
Accompanying drawing explanation
Fig. 1 is reaction scheme of the present invention (for quadrol).
Embodiment
Below in conjunction with embodiment, the present invention will be described in detail.
The preparation method of the anionic Yatall MA Gemini surface active agent that the present invention relates to, comprises the following steps:
Step one: the preparation of amination Yatall MA crude product:
Be 1:(1 ~ 5 by mol ratio) Yatall MA and the mixing of two amine substances, react at 140 ~ 180 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Be 1:(2 ~ 6 by mol ratio) ethylenediamine tetraacetic acid (EDTA) two acid anhydride and obtained amination Yatall MA be dissolved in solvent methanol, stirring reaction 5 ~ 10h at 40 ~ 80 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
In step one, two amine substances are selected from quadrol, different fluorine you ketone diamines, urea, phenylenediamine etc.
Embodiment 1:
Step one: the preparation of amination Yatall MA crude product:
By Yatall MA and the mixing of two amine substances that mol ratio is 1:1, react at 180 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Being that ethylenediamine tetraacetic acid (EDTA) two acid anhydride of 1:2 and obtained amination Yatall MA are dissolved in solvent methanol by mol ratio, stirring reaction 5h at 80 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
In step one, two amine substances are quadrol.
Embodiment 2:
Step one: the preparation of amination Yatall MA crude product:
By Yatall MA and the mixing of two amine substances that mol ratio is 1:2, react at 170 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Being that ethylenediamine tetraacetic acid (EDTA) two acid anhydride of 1:3 and obtained amination Yatall MA are dissolved in solvent methanol by mol ratio, stirring reaction 6h at 70 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
In step one, two amine substances are different fluorine that ketone diamines.
Embodiment 3:
Step one: the preparation of amination Yatall MA crude product:
By Yatall MA and the mixing of two amine substances that mol ratio is 1:4, react at 160 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Being that ethylenediamine tetraacetic acid (EDTA) two acid anhydride of 1:5 and obtained amination Yatall MA are dissolved in solvent methanol by mol ratio, stirring reaction 8h at 60 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
In step one, two amine substances are urea.
Embodiment 4:
Step one: the preparation of amination Yatall MA crude product:
By Yatall MA and the mixing of two amine substances that mol ratio is 1:5, react at 140 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Being that ethylenediamine tetraacetic acid (EDTA) two acid anhydride of 1:6 and obtained amination Yatall MA are dissolved in solvent methanol by mol ratio, stirring reaction 10h at 40 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
In step one, two amine substances are phenylenediamine.
The Yatall MA Gemini surface active agent of the present invention, had both had the high reactivity feature of Gemini surface active agent, also have nontoxic, can the characteristic of biological degradation. The surface tension of micelle-forming concentration and correspondence is 0.34mmol/L and 33.7mN/m.
The content of the present invention is not limited to cited by embodiment, and the conversion of any equivalence that technical solution of the present invention is taked by those of ordinary skill in the art by reading specification sheets of the present invention, the claim being the present invention is contained.
Claims (3)
1. the preparation method of anionic Yatall MA Gemini surface active agent, it is characterised in that:
Comprise the following steps:
Step one: the preparation of amination Yatall MA crude product:
Be 1:(1 ~ 5 by mol ratio) Yatall MA and the mixing of two amine substances, react at 140 ~ 180 DEG C of temperature, obtained amination Yatall MA crude product;
Step 2: the purification of amination Yatall MA crude product:
Adopt distilled water wash to remove two amine substances of non-complete reaction in amination Yatall MA crude product, then carry out vacuum-drying, obtain amination Yatall MA;
Step 3: the preparation of anionic Yatall MA Gemini surface active agent:
Be 1:(2 ~ 6 by mol ratio) ethylenediamine tetraacetic acid (EDTA) two acid anhydride and obtained amination Yatall MA be dissolved in solvent methanol, stirring reaction 5 ~ 10h at 40 ~ 80 DEG C, obtains anionic Yatall MA Gemini surface active agent crude product;
Step 4: the purification of anionic Yatall MA Gemini surface active agent:
By obtained anionic Yatall MA Gemini surface active agent, generating sodium salt with NaOH aqueous solution neutralization reaction, pH=7, obtains anionic Yatall MA Gemini surface active agent.
2. the preparation method of anionic Yatall MA Gemini surface active agent according to claim 1, it is characterised in that:
In step one, two amine substances are selected from quadrol, different fluorine that ketone diamines, urea, phenylenediamine.
3. the tensio-active agent that the preparation method of anionic Yatall MA Gemini surface active agent as claimed in claim 1 obtains.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610000744.2A CN105664786B (en) | 2016-01-04 | 2016-01-04 | Anionic tall oil Gemini surface active agent and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610000744.2A CN105664786B (en) | 2016-01-04 | 2016-01-04 | Anionic tall oil Gemini surface active agent and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105664786A true CN105664786A (en) | 2016-06-15 |
| CN105664786B CN105664786B (en) | 2018-12-21 |
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| CN201610000744.2A Active CN105664786B (en) | 2016-01-04 | 2016-01-04 | Anionic tall oil Gemini surface active agent and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111111550A (en) * | 2019-12-27 | 2020-05-08 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
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| CN101326000A (en) * | 2005-12-06 | 2008-12-17 | 路博润有限公司 | Novel dispersant and compositions thereof |
| US20100196429A1 (en) * | 2007-07-27 | 2010-08-05 | Shiseido Company Ltd. | Oil-In-Water Emulsion Composition And Method For Producing The Same |
| CN104941509A (en) * | 2015-05-11 | 2015-09-30 | 中国海洋石油总公司 | Micro-surfacing slow cracking and rapid setting asphalt emulsifier and preparation method thereof |
-
2016
- 2016-01-04 CN CN201610000744.2A patent/CN105664786B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101326000A (en) * | 2005-12-06 | 2008-12-17 | 路博润有限公司 | Novel dispersant and compositions thereof |
| US20100196429A1 (en) * | 2007-07-27 | 2010-08-05 | Shiseido Company Ltd. | Oil-In-Water Emulsion Composition And Method For Producing The Same |
| CN104941509A (en) * | 2015-05-11 | 2015-09-30 | 中国海洋石油总公司 | Micro-surfacing slow cracking and rapid setting asphalt emulsifier and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 陈林渺等: "含芳香基的乙二胺四乙酸酰胺衍生物的合成", 《合成化学》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111111550A (en) * | 2019-12-27 | 2020-05-08 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
| CN111111550B (en) * | 2019-12-27 | 2021-11-30 | 江门市华熊新材料有限公司 | Fluorine-containing surfactant and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105664786B (en) | 2018-12-21 |
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Effective date of registration: 20191230 Address after: Room f6-517, Jiangsu life science and Technology Innovation Park, No.9, Weidi Road, Xianlin street, Qixia District, Nanjing City, Jiangsu Province Patentee after: Nanjing Shangqin New Material Technology Co.,Ltd. Address before: 710021 Shaanxi city of Xi'an province Weiyang University City Patentee before: SHAANXI University OF SCIENCE & TECHNOLOGY |
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| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Anionic Tar Oil Gemini Surfactant and Its Preparation Method Effective date of registration: 20231227 Granted publication date: 20181221 Pledgee: Bank of China Limited Nanjing Chengdong Branch Pledgor: Nanjing Shangqin New Material Technology Co.,Ltd. Registration number: Y2023980075072 |
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