CN104059783A - Preparation method of surfactant for detergents and detergent composition - Google Patents
Preparation method of surfactant for detergents and detergent composition Download PDFInfo
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Abstract
The invention discloses a preparation method of a surfactant for detergents and a detergent composition comprising the surfactant. The detergent composition is strong in dirt-removing power, low-foam and easy to rinse. The invention further discloses a special detergent composition for clean clothes; the detergent composition comprises the surfactant, alcohol alkoxylate, fatty alcohol-polyoxyethylene ether, a water-soluble growth substance, an anti-redeposition agent, a chelating agent and water; oil stains, sweat stains and other pollutants can be well removed when the detergent composition is used for washing the clean clothes, fibers cannot be damaged, overhigh dust content of the washed clean clothes cannot be caused, and the cleanness performance requirement is met.
Description
Technical field
The present invention relates to the preparation method of tensio-active agent, and the detergent composition that comprises this tensio-active agent.
Background technology
In the clean room in the fields such as electronics, pharmacy, food, space flight, operator often uses cleanness clothing to carry out operation, and in operation process, it is contaminated that cleanness clothing is easy to, and main pollutent has greasy dirt, dust and sweat stain.The main material of cleanness clothing is generally the polyester fabric that contains conductive filament, material is different from normal laundry, and different grades clean room use cleanness clothing have different clean performance requriementss, this just requires will adopt special washing composition and professional washing procedure for the washing of cleanness clothing.
At present also there are some to clean special washing composition for cleanness clothing or polyester piece good, for example Chinese patent CN102643722A discloses a kind of washing composition and preparation method thereof, wherein washing composition comprises octadecyl alkyl dimethyl ammonium chloride, fatty alcohol-polyoxyethylene ether, auxiliary agent and water, the detergent washing effect of this formula is not good enough, and is difficult for rinsing after washing; For another example Chinese patent CN101130717 discloses a kind of terylene and blending dyeing thing detergent thereof, and detergent component comprises Viscotrol C ethylene oxide condensate, isomery 13 carbon fatty alcohol Soxylat A 25-7s, Na
2siO
3, poly carboxylic acid derivative, PVP and Citrate trianion, adopt conventional surfactants and highly basic additive compound, can improve the detersive power to grease by hydrolytic action on the one hand, thereby the consumption that can reduce on the other hand tensio-active agent plays the effect that reduces foam, but the use of highly basic easily causes the damage of clothes fiber in washing process, cause cleanness clothing powder amount large.
Summary of the invention
The present invention, for solving problems of the prior art, provides a kind of detergent composition, and this detergent composition soil removability is strong, the easy rinsing of low bubble.The present invention also provides a kind of cleanness clothing special purpose detergent composition, for cleanness clothing well wipe oil, sweat stain and other pollutents of when washing, and can not cause damage to fiber, and can not cause the cleanness clothing powder amount after washing excessive, meet clean performance requriements.
The present invention solves the problems of the technologies described above by the following technical solutions:
First the present invention provides a kind of preparation method of detergent use tensio-active agent, comprises the following steps:
(1) alkyl glycidyl ether and fatty alcohol, under heating, basic catalyst existence condition, carry out ring-opening reaction;
(2) the ring-opening reaction product of step (1) and oxyethane carry out polyaddition reaction under heating, pressurization and basic catalyst existence condition;
(3) the polyaddition reaction product of step (2) and epoxy chloropropane carry out ring-opening reaction under heating condition;
(4) the ring-opening reaction product of step (3) reacts under heating condition with polyethylene polyamine, makes detergent use tensio-active agent.
In described step (1), alkyl glycidyl ether is 12～18 alkyl glycidyl ethers.
In described step (1), fatty alcohol is 12～18 alcohol.
The mole dosage of fatty alcohol is alkyl glycidyl ether in described step (1) 100～200%.
Described step (1) basic catalyst is sodium hydroxide, and Heating temperature is 70～80 DEG C, and under this condition, the reaction times is 1～2h.
The mole dosage of oxyethane is alkyl glycidyl ether in described step (2) 500～700%.
Described step (2) neutral and alkali catalyzer is sodium hydroxide, and Heating temperature is 130～180 DEG C, and moulding pressure is 0.15～0.6MPa, and under this condition, the reaction times is 3～5h.
Heating temperature is 50 DEG C in described step (3), and the reaction times is 2～3h, and the mole dosage of described epoxy chloropropane is alkyl glycidyl ether 100～300%.
In described step (4), polyethylene polyamine is two or more mixture mixing with arbitrary proportion of diethylenetriamine, triethylene tetramine and tetraethylene pentamine.
Heating temperature is 70 DEG C in described step (4), and under this condition, the reaction times is 30～50h, and the quality consumption of described polyethylene polyamine is alkyl glycidyl ether 50～300%.
The detergent use tensio-active agent that the present invention also provides aforesaid method to obtain.
The invention still further relates to the detergent composition that comprises above-mentioned detergent use tensio-active agent.
When isomery polyoxyethylenated alcohol is added to detergent use tensio-active agent of the present invention, can further improve low bubble effect.That is to say, the invention provides the detergent composition that contains above-mentioned detergent use tensio-active agent and isomery polyoxyethylenated alcohol.
Represent isomery polyoxyethylenated alcohol by formula I:
RO(CH
2CH
2O)
nH (Ⅰ)
Wherein, R represents the branched alkyl group that contains 10～13 carbon atoms, n=8～10.
Preferably the example model of isomery polyoxyethylenated alcohol is isomery ten alcohol ethers 1008, isomery ten alcohol ethers 1009, isomerous tridecanol ether 1308, isomerous tridecanol ether 1309, isomerous tridecanol ether 1310.
When HLB value is greater than to 10 fatty alcohol-polyoxyethylene ether and adds detergent use tensio-active agent of the present invention, can further improve clean effect.That is to say, the invention provides and contain the detergent composition that above-mentioned detergent use tensio-active agent and HLB value are greater than 10 fatty alcohol-polyoxyethylene ether.
The example that HLB value is greater than 10 fatty alcohol-polyoxyethylene ether is fatty alcohol-polyoxyethylene ether AEO-7, fatty alcohol-polyoxyethylene ether AEO-9.
In detergent composition of the present invention, the amount of above-mentioned detergent use tensio-active agent can, according to using and filling a prescription and suitably determine, be generally 0.01～10% (quality), is preferably 0.1～5% (quality).The amount of isomery polyoxyethylenated alcohol is generally 1～10%.The amount of fatty alcohol-polyoxyethylene ether is generally 10～40%.
Do not affecting under the condition of washing effect, in detergent composition, can also add and use other tensio-active agents.The example of other tensio-active agents comprises the nonionogenic tenside such as alkylphenol polyoxyethylene, coco alkyl diethanol amide, sorbitan fatty acid ester; Zwitterionics such as cocamidopropyl betaine, cocounut oil both sexes disodium beclomethasone; Cats product such as octadecyl trimethyl ammonium chloride, cetyl trimethylammonium bromide.
Except above-mentioned tensio-active agent, do not affecting under the condition of washing effect, can also add the multiple auxiliary agent of general use.The example comprises the anti redeposition agent such as sodium carboxymethyl-cellulose, polyvinylpyrrolidone, sodium polyacrylate; Sequestrant such as sodium nitrilo triacetate, tetrasodium ethylenediamine tetraacetate, Trisodium Citrate; Hydrotropic agent such as dipropylene glycol dme, propylene glycol positive propyl ether; White dyes such as VBU, VBS, CBS-X.
The invention provides a kind of cleanness clothing special purpose detergent composition, comprising above-mentioned detergent use tensio-active agent 0.1～2%, isomery polyoxyethylenated alcohol 3～10%, fatty alcohol-polyoxyethylene ether 20～35%, hydrotropic agent 3～5%, anti redeposition agent 0.1～2%, sequestrant 0.05～1%, surplus is water.
Preferred described isomery polyoxyethylenated alcohol is one or more of isomery ten alcohol ethers 1008, isomery ten alcohol ethers 1009, isomerous tridecanol ether 1308, isomerous tridecanol ether 1309, isomerous tridecanol ether 1310.
The HLB value of preferred described fatty alcohol-polyoxyethylene ether is greater than 10, is preferably one or more of fatty alcohol-polyoxyethylene ether AEO-7, fatty alcohol-polyoxyethylene ether AEO-9.
Preferred described hydrotropic agent is dipropylene glycol dme.
Preferred described anti redeposition agent is one or both of polyvinylpyrrolidone, sodium polyacrylate.
Preferred described sequestrant is one or more of sodium nitrilo triacetate, tetrasodium ethylenediamine tetraacetate, Trisodium Citrate.
It is strong that detergent composition of the present invention has soil removability, the advantage of the easy rinsing of low bubble, cleanness clothing special purpose detergent composition of the present invention not only has advantages of the easy rinsing of the strong and low bubble of soil removability, and to cleanness clothing fabric not damaged, float rear without remaining, can not cause cleanness clothing powder amount large, there is higher clean performance.
Embodiment
More specifically the present invention is set forth by the following examples, but the invention is not restricted to these embodiment, below " % " all refers to quality percentage composition if no special instructions.
Table 1 testing method/standard
| Test event | Test method/standard |
| Foaming power | GB/T 13173-2008 |
| Detersive power | GB/T 13174-2008 |
| Cleanness clothing is sent out dirt rate | GB/T 24249-2009 |
Testing method or testing standard that table 1 adopts for embodiment of the present invention test event.
Preparation Example 1:
Get 24.2g (0.1mol) lauryl diglycidyl ether, 18.6g (0.1mol) lauryl alcohol adds in reactor successively at ambient temperature, then add 0.01gNaOH catalyzer, with after nitrogen replacement air, heat under 70 DEG C of conditions and react 3h.Temperature rises to 85 DEG C, under constant temperature, vacuumizes 20min, is then warming up to 130 DEG C, passes into continuously 22g (0.5mol) oxyethane, controls reactor pressure 0.15MPa, and oxyethane is reinforced complete, and insulation is to Pressure Drop to initial pressure.Temperature of reaction is down to 50 DEG C, drips 18.5g (0.2mol) epoxy chloropropane and carry out ring-opening reaction in 30min, constant temperature stirs after 3h, and excessive epoxy chloropropane is removed in underpressure distillation; Be warming up to 200 DEG C, add 12.1g polyethylene polyamine (diethylenetriamine and triethylene tetramine mix with mass ratio 1:1), reaction 4h, obtains the present embodiment detergent use tensio-active agent (A-1).
Preparation Example 2:
Get 32.6g (0.1mol) octadecyl glycidyl ether, 27g (0.1mol) stearyl alcohol adds in reactor successively at ambient temperature, then add 0.01gNaOH catalyzer, with after nitrogen replacement air, heat under 80 DEG C of conditions and react 2h.Then temperature rises to 90 DEG C, under constant temperature, vacuumizes 20min, is then warming up to 180 DEG C, passes into continuously 30.8g (0.7mol) oxyethane, controls reactor pressure 0.3MPa, and oxyethane is reinforced complete, and insulation is to Pressure Drop to initial pressure.Temperature of reaction is down to 60 DEG C, drips 27.75g (0.3mol) epoxy chloropropane and carry out ring-opening reaction in 30min, constant temperature stirs after 2h, and excessive epoxy chloropropane is removed in underpressure distillation; Be warming up to 200 DEG C, add 29.3g polyethylene polyamine (triethylene tetramine and tetraethylene pentamine are mixed with mass ratio 2:1), reaction 6h, obtains the present embodiment detergent use tensio-active agent (A-2).
Preparation Example 3:
Get 27g (0.1mol) tetradecyl glycidyl ether, 48.4g (0.2mol) hexadecanol adds in reactor successively at ambient temperature, then add 0.01gNaOH catalyzer, with after nitrogen replacement air, be heated to react 2h under 80 DEG C of conditions.Then temperature rises to 90 DEG C, under constant temperature, vacuumizes 20min, and temperature is risen to 150 DEG C, passes into continuously 26.4g (0.6mol) oxyethane, controls reactor pressure 0.6MPa, and oxyethane is reinforced complete, and insulation is to Pressure Drop to initial pressure.Temperature of reaction is down to 60 DEG C, drips 18.3g (0.2mol) epoxy chloropropane and carry out ring-opening reaction in 30min, constant temperature stirs after 2h, and excessive epoxy chloropropane is removed in underpressure distillation; Be warming up to 200 DEG C, add 54g polyethylene polyamine (diethylenetriamine, triethylene tetramine and tetraethylene pentamine are mixed with mass ratio 1:1:1), reaction 5h, obtains the present embodiment detergent use tensio-active agent (A-3).
Preparation Example 4:
Get 24.2g (0.1mol) lauryl diglycidyl ether, 27g (0.1mol) stearyl alcohol adds in reactor successively at ambient temperature, then add 0.01gNaOH catalyzer, with after nitrogen replacement air, heat under 80 DEG C of conditions and react 2h.Then temperature is risen to 90 DEG C, under constant temperature, vacuumize 20min, be warming up to 180 DEG C, pass into continuously 30.8g (0.7mol) oxyethane, control reactor pressure 0.4MPa, oxyethane is reinforced complete, and insulation is to Pressure Drop to initial pressure.System temperature is down to 60 DEG C, drips 27.75g (0.3mol) epoxy chloropropane and carry out ring-opening reaction in 30min, constant temperature stirs after 2h, and excessive epoxy chloropropane is removed in underpressure distillation; Be warming up to 200 DEG C, add 72.6g polyethylene polyamine (diethylenetriamine and tetraethylene pentamine are mixed with mass ratio 3:1), reaction 5h, obtains the present embodiment detergent use tensio-active agent (A-4).
In employing standard GB/T 13173-2008 surfactant detergent test method, the measuring method of washing composition foaming power is measured the foaming power of Preparation Example tensio-active agent of the present invention and comparative example tensio-active agent, test condition is 20 DEG C, 0.1% aqueous solution, and measurement result is as shown in table 2.
Wherein comparative example tensio-active agent is respectively Sodium dodecylbenzene sulfonate (LAS), fatty alcohol-polyoxyethylene ether (paregal O), the low alveolitoid emulsifying agent of commercially available Lao Ruitan (FT1379).
Table 2 foaming power test result
As clearly seen from Table 2, tensio-active agent of the present invention, compared with conventional tensio-active agent, has lower foaming power and shorter foam life.
Test example 1～8
Detergent composition shown in preparation table 3, tests its foaming power and detersive power, and test result is as table 4.
The preparation of table 3 detergent composition
* be 100% for adding to total amount.
Table 4 foaming power and detergency test result
Can know and find out from table 4, washing composition of the present invention and certain commercially available washing composition comparison, have the following advantages: low bubble (foam height is lower), froth breaking fast (foam life is shorter), (when detergent use surfactant content of the present invention is 0.01%, comprehensive detersive power is suitable with commercially available washing composition for strong detergency, when content >=0.1%, comprehensive detersive power is all far longer than commercially available washing composition), can be found out by embodiment 3 and 6, isomery polyoxyethylenated alcohol has further improved the low bubble effect of detergent composition of the present invention, by embodiment 4, 5 can find out that HLB value is greater than the detersive power of 10 the favourable raising of fatty alcohol-polyoxyethylene ether detergent composition of the present invention.
Test example 9
Press the cleanness clothing special purpose detergent composition of table 5 component and component concentration test preparation embodiment 9.
Table 5 cleanness clothing formulation of detergent composition
| Component | Content/% |
| A-1 | 0.1 |
| Isomery ten alcohol ethers 1008 | 3 |
| Fatty alcohol-polyoxyethylene ether AEO-7 | 20 |
| Dipropylene glycol dme | 3 |
| Polyvinylpyrrolidone | 0.1 |
| Sodium nitrilo triacetate | 0.05 |
| Purify waste water | Add to 100% |
Test example 10
Press the cleanness clothing special purpose detergent composition of table 6 component and component concentration test preparation embodiment 10.
Table 6 cleanness clothing formulation of detergent composition
| Component | Content/% |
| A-2 | 1 |
| Isomery ten alcohol ethers 1009 | 5 |
| Fatty alcohol-polyoxyethylene ether AEO-9 | 25 |
| Dipropylene glycol dme | 4 |
| Sodium polyacrylate | 1 |
| Tetrasodium ethylenediamine tetraacetate | 0.2 |
| Purify waste water | Add to 100% |
Test example 11
Press the cleanness clothing special purpose detergent composition of table 7 component and component concentration test preparation embodiment 11
Table 7 cleanness clothing formulation of detergent composition
| Component | Content/% |
| A-3 | 2 |
| Isomerous tridecanol ether 1308 | 5 |
| Isomerous tridecanol ether 1309 | 5 |
| Fatty alcohol-polyoxyethylene ether AEO-7 | 30 |
| Dipropylene glycol dme | 4 |
| Sodium polyacrylate | 2 |
| Trisodium Citrate | 1 |
| Purify waste water | Add to 100% |
Test example 12
Press the cleanness clothing special purpose detergent composition of table 8 component and component concentration test preparation embodiment 12
Table 8 cleanness clothing formulation of detergent composition
| Component | Content/% |
| A-4 | 2 |
| Isomerous tridecanol ether 1310 | 5 |
| Fatty alcohol-polyoxyethylene ether AEO-9 | 5 |
| Fatty alcohol-polyoxyethylene ether AEO-7 | 30 |
| Dipropylene glycol dme | 4 |
| Sodium polyacrylate | 2 |
| Trisodium Citrate | 1 |
| Purify waste water | Add to 100% |
Simultaneous test embodiment 1
Press the cleanness clothing special purpose detergent composition of table 9 component and component concentration preparation simultaneous test embodiment 1.
Table 9 cleanness clothing formulation of detergent composition
| Component | Content/% |
| Viscotrol C ethylene oxide condensate | 15 |
| Isomerous tridecanol ether 1310 | 15 |
| Na2SiO3 | 5 |
| Sodium polyacrylate | 10 |
| Polyvinylpyrrolidone | 5 |
| Trisodium Citrate | 5 |
| Purify waste water | Add to 100% |
Foaming power and the detersive power of the detergent composition of testing experiment embodiment 9～12 cleanness clothing special purpose detergent compositions and simultaneous test embodiment 1, and the powder amount of the cleanness clothing of process cleaning, test result is as table 10.
Table 10 foaming power, detersive power and powder amount test result
Can know and find out from table 10, cleanness clothing special purpose detergent of the present invention is remarkable for the washing effect of cleanness clothing, detersive power is more than 1.5, and the easy rinsing of low bubble, after washing, can not cause cleanness clothing powder amount excessive, meet the clean performance requriements that cleanness clothing uses, and simultaneous test embodiment 1 not only detersive power is lower, and owing to having used water glass strong basicity auxiliary agent, cause the damage of clothes fiber, make cleanness clothing powder amount larger.
Claims (11)
1. a preparation method for detergent use tensio-active agent, is characterized in that, comprises the following steps:
(1), alkyl glycidyl ether and fatty alcohol carry out ring-opening reaction under heating and basic catalyst existence condition;
(2), the reaction product of step (1) and oxyethane carry out polyaddition reaction under heating, pressurization and basic catalyst existence condition;
(3), the reaction product of step (2) and epoxy chloropropane carry out ring-opening reaction under heating condition;
(4), the ring-opening reaction product of step (3) reacts under heating condition with polyethylene polyamine, makes detergent use tensio-active agent.
2. the preparation method of detergent use tensio-active agent according to claim 1, is characterized in that, in described step (1), alkyl glycidyl ether is 12～18 alkyl glycidyl ethers, and fatty alcohol is 12～18 alcohol.
3. the preparation method of detergent use tensio-active agent according to claim 1, is characterized in that, described step (1) basic catalyst is sodium hydroxide, and Heating temperature is 70～80 DEG C, and the reaction times is 1～2h; Described step (2) basic catalyst is sodium hydroxide, and Heating temperature is 130～180 DEG C, and moulding pressure is 0.15～0.6MPa; Described step (3) Heating temperature is 50 DEG C, and the reaction times is 2～3h; Described step (4) Heating temperature is 200 DEG C, and the reaction times is 4～6h.
4. the preparation method of detergent use tensio-active agent according to claim 1, it is characterized in that, in described step (4), polyethylene polyamine is two or more mixture mixing with arbitrary proportion of diethylenetriamine, triethylene tetramine and tetraethylene pentamine.
5. the detergent use tensio-active agent that in claim 1～4, either method obtains.
6. a detergent composition, is characterized in that, comprises detergent use tensio-active agent as claimed in claim 5.
7. detergent composition according to claim 6, is characterized in that, described detergent composition also comprises isomery polyoxyethylenated alcohol, and described isomery polyoxyethylenated alcohol has the structure as shown in formula I:
RO(CH
2CH
2O)
nH (Ⅰ)
Wherein, R represents the branched alkyl group that contains 10～13 carbon atoms, n=8～10.
8. according to the detergent composition described in claim 6～7 any one, it is characterized in that, described detergent composition also comprises fatty alcohol-polyoxyethylene ether, and the HLB value of described fatty alcohol-polyoxyethylene ether is greater than 10.
9. detergent composition according to claim 8, is characterized in that, described fatty alcohol-polyoxyethylene ether is selected from one or both of AEO-7, AEO-9.
10. detergent composition according to claim 6, is characterized in that, the quality percentage composition of described detergent use tensio-active agent is 0.01～10%.
11. 1 kinds of cleanness clothing special purpose detergent compositions, it is characterized in that, comprise that detergent use tensio-active agent 0.1～2% as claimed in claim 5, isomery polyoxyethylenated alcohol 3～10%, fatty alcohol-polyoxyethylene ether 20～35%, hydrotropic agent 3～5%, anti redeposition agent 0.1～2%, sequestrant 0.05～1%, surplus are water.
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| CN111138655A (en) * | 2019-12-16 | 2020-05-12 | 上海创化材料科技有限公司 | Novel polyether ester nonionic surfactant and preparation method thereof |
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| CN114836270A (en) * | 2022-02-24 | 2022-08-02 | 青岛小鹿先生智能科技有限公司 | Machine-washing shoe washing liquid and preparation method thereof |
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| CN104818160A (en) * | 2015-04-28 | 2015-08-05 | 威莱(广州)日用品有限公司 | Kitchen degreasing agent and preparation method thereof |
| CN104830578A (en) * | 2015-04-30 | 2015-08-12 | 威莱(广州)日用品有限公司 | High-efficiency toilet cleaning agent and preparation method thereof |
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| CN111138655A (en) * | 2019-12-16 | 2020-05-12 | 上海创化材料科技有限公司 | Novel polyether ester nonionic surfactant and preparation method thereof |
| CN111138655B (en) * | 2019-12-16 | 2022-10-25 | 上海创化材料科技有限公司 | Polyether ester nonionic surfactant and preparation method thereof |
| CN114016291A (en) * | 2021-11-15 | 2022-02-08 | 广东灵捷制造化工有限公司 | Cold reactor pretreatment auxiliary agent and application thereof |
| CN114016291B (en) * | 2021-11-15 | 2023-11-17 | 广东灵捷制造化工有限公司 | Cold stack pretreatment auxiliary agent and application thereof |
| CN114836270A (en) * | 2022-02-24 | 2022-08-02 | 青岛小鹿先生智能科技有限公司 | Machine-washing shoe washing liquid and preparation method thereof |
| CN114836270B (en) * | 2022-02-24 | 2024-02-23 | 青岛小鹿先生智能科技有限公司 | Machine-washing shoe-washing liquid and preparation method thereof |
| WO2023178580A1 (en) * | 2022-03-24 | 2023-09-28 | Ecolab Usa Inc. | Laundry emulsifier with surfactant and solvent |
| CN116556084A (en) * | 2023-05-30 | 2023-08-08 | 常州保洁洗涤剂制造有限公司 | One-step energy-saving auxiliary agent for cone dyeing and preparation method thereof |
| CN116556084B (en) * | 2023-05-30 | 2023-11-10 | 常州保洁洗涤剂制造有限公司 | One-step energy-saving auxiliary agent for cone dyeing and preparation method thereof |
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