CN106397776A - Double amino type block polyether amino silicone oil and preparation method thereof - Google Patents
Double amino type block polyether amino silicone oil and preparation method thereof Download PDFInfo
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- CN106397776A CN106397776A CN201610768421.8A CN201610768421A CN106397776A CN 106397776 A CN106397776 A CN 106397776A CN 201610768421 A CN201610768421 A CN 201610768421A CN 106397776 A CN106397776 A CN 106397776A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Silicon Polymers (AREA)
Abstract
The invention belongs to the field of textile post-finishing auxiliaries and particularly relates to double amino type block polyether amino silicone oil and a preparation method thereof. The double amino type block polyether amino silicone oil is characterized in that the structural formula of a compound is shown as follows (structural formula 1), wherein EO is -CH2CH2O-, PO is -CH(CH3)CH2O-, n is 50-500, a is 10-40, b is 0-6, m is 2-40, and R is -CH2CH2- and -CH(CH3)CH2-, -CH2CH2CH2-or -CH2CH2CH2Ch2-. The double amino type block polyether amino silicone oil prepared by the invention can be compared with ordinary amino silicone oil in mouth feeling, has less influence on the whiteness of a fabric, simultaneously has excellent acid and alkali resistance, shear resistance and salt resistance, can completely replace the ordinary amino silicone oil and has an optimal application prospect.
Description
Technical field
The invention belongs to spinning post-finishing auxiliary agent field, particularly to a kind of pair of amino-type block polyether amino silicone oil and its
Preparation method.
Background technology
Stability of emulsion is poor due to existing for common amido silicon oil, the easy yellowing of the fabric after process, moisture absorbing and sweat releasing property difference
Shortcoming, is progressively substituted by various types of block polyether modified amino silicon oils.Due to the introducing of hydrophilic polyether segment, emulsion
Good stability.And, polyether segment is embedded in the structure of the main chain film property on polysiloxanes on fabric fibre to be affected relatively
Little it is easy to play its soft, smooth, fluffy performance.This is that block polyether amino silicone oil is had with respect to common amido silicon oil
Some advantages.
However, the amido functional group in block polyether amino silicone oil is only distributed in the two ends of polysiloxanes segment, by structure
Impact, ammonia value can not arbitrarily change.Polysiloxanes segment is longer, and ammonia value is just little.And ammonia value will be improved, poly- silica can only be reduced
The molecular weight of alkane segment.This contradiction limits the raising further of block polyether amino silicone oil feel.
Content of the invention
The invention provides a kind of soft, smooth, bulkiness is all good, good emulsion stability and there is certain yellowing resistance
Double amino-type block polyether amino silicone oil.
Present invention also offers the preparation method of described pair of amino-type block polyether amino silicone oil.
The technical solution adopted for the present invention to solve the technical problems is：
A kind of pair of amino-type block polyether amino silicone oil, the structural formula of this compound is following (structural formula 1)：
Wherein, EO is-CH2CH2O-, PO are-CH (CH3)CH2O-, n be 50～500, a be 10～40, b be 0～6, m be 2
～40, R are-CH2CH2-、-CH(CH3)CH2-、-CH2CH2CH2- or-CH2CH2CH2CH2-.
Preferably, n is 100～300, a is 2～6 for 10～40, b.
The preparation method of a kind of pair of amino-type block polyether amino silicone oil, the method comprises the following steps：
A, the synthesis of amino double-seal head
Add diamine in the reactor of inert gas shielding, under agitation, be slowly added to epoxy double-seal head, 2h
Interior addition finishes, and 6-10h is stirred at room temperature, and then heats to 60-80 DEG C, continues insulation 6-10h；Vacuum distillation extracts unnecessary two out
First amine, prepared amino double-seal head (structural formula 2),
B, α, the synthesis of ω-bis- amido silicon oils
By amino double-seal head, organosiloxane ring body (DMC) mix homogeneously, add base catalyst, be warming up to 80 DEG C～
110 DEG C, react 12～18h；Then heat to 140～150 DEG C of reaction 1h～2h with decomposition catalyst, vacuum distillation removes low boiling
Thing, that is, be obtained α, ω-bis- amido silicon oils；
C, α, the block polymerization of ω-bis- amido silicon oils and end epoxidized polyether
By end epoxidized polyether (structural formula 3), α, ω-bis- amido silicon oils and organic solvent mix homogeneously, at 60 DEG C～80 DEG C
Reaction 15～20h, is neutralized to pH=6～7 with organic acid, that is, double amino-type block polyether amino silicone oil are obtained,
Double amino-type block polyether amino silicone oil feels of present invention preparation can be matched in excellence or beauty with common amido silicon oil, to fabric
Whiteness impact is less, has excellent resistance to acids and bases, endurance of cutting and salt tolerance simultaneously, can replace common amino silicone completely
Oil, has splendid application prospect.
Preferably, in step a, described diamine is ethylenediamine, 1,2- propane diamine, 1,3- propane diamine, Isosorbide-5-Nitrae-fourth two
One or more of amine.
Preferably, in step a, diamine is 5 with the mol ratio of epoxy double-seal head:1～10:1.
Preferably, in step b, described base catalyst is (CH3)4NOH alkali glue or (n-C4H9)4POH alkali glue, alkalescence
Catalyst amount (effective content of catalyst) is the 0.05%～0.1% of reactant gross mass.
Preferably, in step b, the mass ratio of amino double-seal head and organosiloxane ring body (DMC) is 1:10～100.
Preferably mass ratio is 1:20～50.
Preferably, the organic solvent described in step c is isopropanol, ethylene glycol monobutyl ether, ethylene glycol ether, second two
The combination of one or more of alcohol list ether, glycol monoethyl ether and diethylene glycol monomethyl ether.The consumption of organic solvent is general
For reaction system gross mass 5%～65%.
Preferably, the organic acid described in step c is acetic acid or lauric acid.
The present invention compared with prior art has advantages below：
1) present invention employs epoxy double-seal head and organic diamine and prepare amino double-seal head, then with organosiloxane ring body
(DMC) ring-opening polymerisation generates the technology path of Amino End Group silicone oil；With first directly prepare epoxy silicon oil with epoxy double-seal head, then with two
The method that Amino End Group silicone oil is prepared in first amine reaction is compared, and reactive group retention rate height in two ends is it is ensured that lower step is embedding with polyether group
The high reaction activity of Duan Juhe；
2) double amino-type block polyether amino silicone oil of present invention preparation, the connection of polysiloxanes segment two ends for diamine
Group, ammonia value is original twice, and polarity, reactivity and the adsorptivity of product are greatly improved, and consumption is less, feel more preferably,
Efficiently solve the contradiction between common block polyether amino silicone oil hydrophilic and feel；Its feel not defeated in common amido silicon oil,
And there is more preferable stability of emulsion and yellowing resistance.
Specific embodiment
Below by specific embodiment, technical scheme is described in further detail.It should be appreciated that this
Bright enforcement is not limited to the following examples, and any pro forma flexible and/or change that the present invention is made all will fall
Enter the scope of the present invention.
In the present invention, if not refering in particular to, all of part, percentage ratio are unit of weight, the equipment being adopted and raw material etc.
All it is commercially available or commonly used in the art.Method in following embodiments, if no special instructions, is the normal of this area
Rule method.
Embodiment 1：
In the reactor of nitrogen protection, disposable addition 1,3- propane diamine 45g, under agitation, is slowly added to 36g
Epoxy double-seal head, adds in 2h and finishes, 6h is stirred at room temperature, then heats to 80 DEG C, continues insulation 8h；It is unnecessary that vacuum distillation is extracted out
Diamine, that is, be obtained amino double-seal head；The amino double-seal head that upper step is obtained, 700g organosiloxane ring body (DMC) mix
Uniformly, add 0.7g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 100 DEG C, reacts 15h；Then heat to 140～
In the range of 150 DEG C, with decomposition catalyst, vacuum distillation removes low-boiling-point substance to reaction 2h, that is, α, ω-bis- amido silicon oils are obtained；By 92g
End epoxidized polyether (molecular weight 920), 560g isopropanol adds reaction system, reacts 20h at 80 DEG C, is neutralized to pH=with organic acid
7, that is, double amino-type block polyether amino silicone oil are obtained.
Embodiment 2：
In the reactor of nitrogen protection, disposable addition Putriscine 53g, under agitation, is slowly added to 36g
Epoxy double-seal head, adds in 2h and finishes, 6h is stirred at room temperature, then heats to 80 DEG C, continues insulation 8h；It is unnecessary that vacuum distillation is extracted out
Diamine, that is, be obtained amino double-seal head；The amino double-seal head that upper step is obtained, 955g organosiloxane ring body (DMC) mix
Uniformly, add 0.9g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 80 DEG C DEG C, reacts 18h；Then heat to 150 DEG C
Reaction 1h removes low-boiling-point substance with decomposition catalyst, vacuum distillation, that is, α, ω-bis- amido silicon oils are obtained；By 185g end epoxidized polyether
(molecular weight 1850), 500g isopropanol and 300 ethylene glycol monobutyl ethers add reaction system, react 20h at 60 DEG C, with organic acid
With to pH=6.5, that is, double amino-type block polyether amino silicone oil are obtained.
Embodiment 3：
In the reactor of nitrogen protection, disposable addition 1,3- propane diamine 50g, under agitation, is slowly added to 36g
Epoxy double-seal head, adds in 2h and finishes, 6h is stirred at room temperature, then heats to 80 DEG C, continues insulation 8h；It is unnecessary that vacuum distillation is extracted out
Diamine, that is, be obtained amino double-seal head；The amino double-seal head that upper step is obtained, 1160g organosiloxane ring body (DMC) mix
Uniformly, add 1g (CH3)4NOH (is added) in the form of alkali glue, is warming up to 110 DEG C, reacts 16h；Then heat to 140～150
With decomposition catalyst, vacuum distillation removes low-boiling-point substance, that is, α, ω-bis- amido silicon oils are obtained for DEG C reaction 1h；By 92g end epoxidized polyether
(molecular weight 920), 1500g isopropanol adds reaction system, reacts 15h at 60 DEG C, is neutralized to pH=6～7 with organic acid, that is, makes
Obtain double amino-type block polyether amino silicone oil.
Embodiment 4：
In the reactor of nitrogen protection, disposable addition Putriscine 55g, under agitation, is slowly added to 36g
Epoxy double-seal head, adds in 2h and finishes, 6h is stirred at room temperature, then heats to 80 DEG C, continues insulation 8h；It is unnecessary that vacuum distillation is extracted out
Diamine, that is, be obtained amino double-seal head；The amino double-seal head that upper step is obtained, 1355g organosiloxane ring body (DMC) mix
Uniformly, add 1.4g (n-C4H9)4POH (is added) in the form of alkali glue, is warming up to 100 DEG C, reacts 12h；Then heat to 150
With decomposition catalyst, vacuum distillation removes low-boiling-point substance, that is, α, ω-bis- amido silicon oils are obtained for DEG C reaction 1.5h；By 185g end ring oxygen
Polyethers (molecular weight 1850), 1200g isopropanol and 550g ethylene glycol monobutyl ether add reaction system, react 18h at 70 DEG C, with having
Machine acid is neutralized to pH=6, that is, double amino-type block polyether amino silicone oil are obtained.
The preparation of finishing agent：
The said goods are stirred with a small amount of nonionic emulsifier, is then slowly added into while stirring containing glacial acetic acid
Water, opens the emulsion of dilute one-tenth 10wt.%, finally adjusts pH to 6 about with glacial acetic acid.
The technique for applying of finishing agent：
Process fabric：Ployester/Cotton Twill Fabric,
Handling process：Consumption 30g/L,
One immersing and rolling (pick-up：70%) → drying and shaping (150 DEG C × 60S) → cooling moisture regain → performance evaluation；
Performance test with compare：
Feel：Touch rating method using many staff, according to the loft after fabric treating, pliability, resilience and smooth degree
Evaluated etc. composite factor, be divided into 1～5 grade, the bigger feel of numerical value is better；Whiteness：Measured by whiteness instrument, with former cloth
Difference is less, illustrates that yellowing resistance is better；Test result is shown in Table 1.Stability test：Main test resistance to acids and bases, endurance of cutting,
Salt tolerance.Test result is shown in Table 2.
Table 1 use limits table
| Sample sequence number | Former cloth | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Common amido silicon oil |
| Feel | 1 | 4 | 4.5 | 4.5 | 4 | 4.5 |
| Whiteness | 90.2 | 84.5 | 86.4 | 87.3 | 88.1 | 79.8 |
Table 2 stability evaluation table
Can be seen that the double amino-type block polyether amino silicone oil feels according to present invention preparation can from above test data
Match in excellence or beauty with common amido silicon oil, the whiteness of fabric is affected less, there is excellent resistance to acids and bases, endurance of cutting and salt tolerant simultaneously
Property, common amido silicon oil can be replaced completely, there is splendid application prospect.
Claims (9)
1. a kind of pair of amino-type block polyether amino silicone oil it is characterised in that：The structural formula of this compound is following (structural formula 1)：
Wherein, EO is-CH2CH2O-, PO are-CH (CH3)CH2O-, n be 50～500, a be 10～40, b be 0～6, m be 2～40,
R is-CH2CH2-、-CH(CH3)CH2-、-CH2CH2CH2- or-CH2CH2CH2CH2-.
2. according to claim 1 pair of amino-type block polyether amino silicone oil it is characterised in that：N for 100～300, a is
10～40, b are 2～6.
3. a kind of preparation method of the double amino-type block polyether amino silicone oil described in claim 1 is it is characterised in that the method
Comprise the following steps：
A, the synthesis of amino double-seal head
Add diamine in the reactor of inert gas shielding, under agitation, be slowly added to epoxy double-seal head, add in 2h
Enter to finish, 6-10h is stirred at room temperature, then heat to 60-80 DEG C, continue insulation 6-10h；Vacuum distillation extracts unnecessary binary out
Amine, prepared amino double-seal head (structural formula 2),
B, α, the synthesis of ω-bis- amido silicon oils
By amino double-seal head, organosiloxane ring body (DMC) mix homogeneously, add base catalyst, be warming up to 80 DEG C～110
DEG C, react 12～18h；Then heat to 140～150 DEG C of reaction 1h～2h with decomposition catalyst, vacuum distillation removes low-boiling-point substance,
α, ω-bis- amido silicon oils are obtained；
C, α, the block polymerization of ω-bis- amido silicon oils and end epoxidized polyether
By end epoxidized polyether (structural formula 3), α, ω-bis- amido silicon oils and organic solvent mix homogeneously, react at 60 DEG C～80 DEG C
15～20h, is neutralized to pH=6～7 with organic acid, that is, double amino-type block polyether amino silicone oil are obtained,
4. preparation method according to claim 3 it is characterised in that：In step a, described diamine is ethylenediamine, 1,
One or more of 2- propane diamine, 1,3- propane diamine, 1,4- butanediamine.
5. preparation method according to claim 3 it is characterised in that：In step a, diamine and epoxy double-seal head mole
Than for 5:1～10:1.
6. preparation method according to claim 3 it is characterised in that：In step b, described base catalyst is (CH3)4NOH alkali glue or (n-C4H9)4POH alkali glue, base catalyst consumption (effective content of catalyst) is reactant gross mass
0.05%～0.1%.
7. preparation method according to claim 3 it is characterised in that：In step b, amino double-seal head and organosiloxane ring
The mass ratio of body (DMC) is 1:10～100.
8. preparation method according to claim 3 it is characterised in that：Organic solvent described in step c is isopropanol, second
One of glycol monobutyl ether, ethylene glycol ether, ethylene glycol monoethyl ether, glycol monoethyl ether and diethylene glycol monomethyl ether or several
The combination planted.
9. preparation method according to claim 3 it is characterised in that：Organic acid described in step c is acetic acid or the moon
Cinnamic acid.
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Cited By (6)
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| CN107227622A (en) * | 2017-06-15 | 2017-10-03 | 兴化市大地蓝绢纺有限公司 | The preparation method of the super soft finishing agent of organic block silk |
| CN109403048A (en) * | 2018-10-29 | 2019-03-01 | 浙江科峰新材料有限公司 | A kind of cotton hydrophilic block polyethers amido silicon oil and preparation method thereof |
| CN109535428A (en) * | 2018-12-04 | 2019-03-29 | 江西蓝星星火有机硅有限公司 | A kind of poly- ammonium modified polyether silicone oil and its preparation method and application |
| CN111410751A (en) * | 2019-01-08 | 2020-07-14 | 上海氟达化学有限公司 | Preparation method of amphoteric organic silicon polymer emulsion |
| CN114702680A (en) * | 2022-01-11 | 2022-07-05 | 浙江科峰新材料有限公司 | Ultrahigh-stability block silicone oil and preparation method thereof |
| CN115181274A (en) * | 2022-06-29 | 2022-10-14 | 浙江科峰有机硅股份有限公司 | Super-soft and smooth block polyether amino silicone oil and preparation method thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107227622A (en) * | 2017-06-15 | 2017-10-03 | 兴化市大地蓝绢纺有限公司 | The preparation method of the super soft finishing agent of organic block silk |
| CN109403048A (en) * | 2018-10-29 | 2019-03-01 | 浙江科峰新材料有限公司 | A kind of cotton hydrophilic block polyethers amido silicon oil and preparation method thereof |
| CN109535428A (en) * | 2018-12-04 | 2019-03-29 | 江西蓝星星火有机硅有限公司 | A kind of poly- ammonium modified polyether silicone oil and its preparation method and application |
| CN111410751A (en) * | 2019-01-08 | 2020-07-14 | 上海氟达化学有限公司 | Preparation method of amphoteric organic silicon polymer emulsion |
| CN114702680A (en) * | 2022-01-11 | 2022-07-05 | 浙江科峰新材料有限公司 | Ultrahigh-stability block silicone oil and preparation method thereof |
| CN115181274A (en) * | 2022-06-29 | 2022-10-14 | 浙江科峰有机硅股份有限公司 | Super-soft and smooth block polyether amino silicone oil and preparation method thereof |
| CN115181274B (en) * | 2022-06-29 | 2023-11-10 | 浙江科峰有机硅股份有限公司 | Super-soft sliding block polyether amino silicone oil and preparation method thereof |
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Application publication date: 20170215 |