CN106589387A - Synthetic method of polyurethane modified polysiloxane flax finishing softener - Google Patents
Synthetic method of polyurethane modified polysiloxane flax finishing softener Download PDFInfo
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- CN106589387A CN106589387A CN201611265847.8A CN201611265847A CN106589387A CN 106589387 A CN106589387 A CN 106589387A CN 201611265847 A CN201611265847 A CN 201611265847A CN 106589387 A CN106589387 A CN 106589387A
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- Prior art keywords
- polyurethane
- reaction
- conversion ratio
- toluene
- hydrogen siloxane
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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
- C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- 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
-
- 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
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Silicon Polymers (AREA)
Abstract
The invention discloses a synthetic method of a polyurethane modified polysiloxane flax finishing softener, and belongs to the technical field of synthesis of flax finishing softeners. The synthetic method comprises the following steps: adding 16.06g of polymethyl hydrogen siloxane, 20.67-23.28g of methylbenzene, a polymerization inhibitor namely phenothiazine of which the mass is 0.05-0.1% of that of vinyl-terminated polyurethane (VPU), and a chloroplatinic acid-isopropanol catalyst solution of which the mass is 30-60ppm of the total mass of a grafting modified monomer into a 150ml four-neck flask provided with a reflux condensing tube and a dropping funnel at first; and then introducing nitrogen for 5min, performing heating and stirring to ensure that polymethyl hydrogen siloxane is dissolved in methylbenzene, then raising the temperature to 80 DEG C, dropwise adding a mixed solution containing 10.5g of methylbenzene and 4.17-5.14g of vinyl-terminated polyurethane by using a constant-pressure dropping funnel, controlling the time for dropwise adding to be 1.5-2h, heating a reaction system to 100-120 DEG C, performing stirring continuously, keeping constant-temperature reaction for 10-20h, and stopping the reaction. When the yield of a reactant reaches 93% or above, the silicon hydrogen addition reaction is basically finished, thereby obtaining polyurethane modified polysiloxane.
Description
Technical field
The present invention relates to a kind of polyurethane-modified polysiloxanes flax arranges the synthetic method of softening agent, belong to flax arrangement
Softening agent synthesis technical field.
Background technology
Polysiloxanes has relatively low surface tension, with the premium properties that film forming is easily sprawled in fabric face, makes arrangement
Fabric afterwards possesses the arrangement style and feel of uniqueness, the characteristics of polyurethanyl group has coating, flexibility good so that its
Fabric sofetening arrangement, coating, thickening, antifouling, medical and resin modified aspect obtain extensively application.With reference to polyurethane and poly- silica
The advantage of alkane, can give sodolin excellent finishing effect, meanwhile, the active polyurethane group on polysiloxane chain can be with
The reactivity of polysiloxane chain and flax fiber is given, is strengthened long-acting arrangement of the organosilicon flexible finishing agent to sodolin and is imitated
Really.Directly addition reaction of hydrogen is carried out using the polymethyl hydrogen siloxane silicon of macromolecular and certain chain length, prepared polyurethane-modified poly-
The research of siloxanes at home and abroad has not been reported with its application.At present, polysiloxanes is modified both at home and abroad, be mostly using from
Small molecule silane or siloxanes set out, after active group is introduced, then the modified polyorganosiloxane needed for equilibrating is obtained, but this
The many Jing of kind of method some steps just obtain target product, the yield of impact final product, and final product be likely to it is set
There is any discrepancy for the structure of meter.And directly the polymethyl hydrogen siloxane of macromolecular is modified, it is possible to reduce unnecessary pair in course of reaction
The appearance of product, and the yield of target product is higher, this synthetic route is typically seldom adopted, particularly by containing polyurethane
Functional group is introduced on polysiloxane chain, and so as to obtain the synthetic method of polyurethane-modified organosilicon product, the country yet there are no disclosure
Report.The present invention starts with from the selection of new monomer and synthetic method, and research prepares the relatively effective approach of above-mentioned modified silicon oil.
The content of the invention
It is an object of the invention to provide a kind of synthetic method of polyurethane-modified polysiloxanes.
Technical scheme proposed by the present invention is：It is first in the 150mL four-hole boiling flasks equipped with reflux condensing tube and dropping funel
It is initially charged polymethyl hydrogen siloxane 16.06g；Toluene 20.67g～23.28g and quality are end thiazolinyl polyurethane（VPU）Quality
0.05%～0.1% polymerization inhibitor phenthazine, quality for the 30ppm～60ppm of graft modification monomer gross mass chloroplatinic acid-different
Propyl alcohol catalyst solution；Logical nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, then heats to 80 DEG C, uses
Constant pressure funnel is added dropwise the mixed solution containing 10.5g toluene and 4.17g ~ 5.14g ends thiazolinyl polyurethane, and control time exists
Completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 10h ~ 20h to stop to 100 DEG C ~ 120 DEG C
Reaction.Reactant yield reaches more than 93%, then hydrosilylation terminates substantially.Obtain polyurethane-modified polysiloxanes.
It is pure that toluene recited above, polymerization inhibitor phenthazine, chloroplatinic acid, isopropanol etc. are analysis.
Thiazolinyl polyurethane in end recited above, polymethyl hydrogen siloxane are technical grade.
Conversion ratio assay method recited above is that eudiometry determines hydrosilylation conversion ratio:
Conversion ratio (%)=[(Vo- V)/Vo] ×100%
In formula：V --- the gas flow that remaining Si-H is produced after reaction certain hour,
V0--- the gas flow that the Si-H of equivalent unreacted polymethyl hydrogen siloxane is produced.
The invention has the beneficial effects as follows：Polymethyl hydrogen siloxane, end thiazolinyl polyurethane first is raw material, its wide material sources,
Moderate cost, fully, product isolates and purifies easy, to obtain polyurethane-modified polysiloxanes yield height for addition reaction.Due to
, as one kind that flax softening agent is in constitutionally stable compound, their resistance to biodeteriorations are good, with animal body for the material
Without rejection phenomenon, adverse effect, environmental protection are not produced to environment.Next utilizes hydrosilylation, and reaction scheme is succinct, turns
Rate is higher.
Specific embodiment
Embodiment 1
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 20.67g and quality are end thiazolinyl polyurethane（VPU）The polymerization inhibitor phenthazine of the 0.05% of quality, quality are
The chloroplatinic acid-isopropanol of the 60ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：It is added dropwise containing 10.5g toluene and 4.17g ends thiazolinyl polyurethane with constant pressure funnel（VPU）Mixed solution,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 15h to stop to 120 DEG C
Conversion ratio is surveyed in reaction；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Obtain polyurethane-modified gathering
Siloxanes.
Embodiment 2
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 21.2g and quality are end thiazolinyl polyurethane（VPU）The polymerization inhibitor phenthazine of the 0.05% of quality, quality are
The chloroplatinic acid-isopropanol of the 50ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：It is added dropwise containing 10.5g toluene and 4.58g ends thiazolinyl polyurethane with constant pressure funnel（VPU）Mixed solution,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 15h to stop to 120 DEG C
Conversion ratio is surveyed in reaction；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Obtain polyurethane-modified gathering
Siloxanes.
Embodiment 3
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 22.6g and quality are end thiazolinyl polyurethane（VPU）The polymerization inhibitor phenthazine of the 0.05% of quality, quality are
The chloroplatinic acid-isopropanol of the 40ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：It is added dropwise containing 10.5g toluene and 4.73g ends thiazolinyl polyurethane with constant pressure funnel（VPU）Mixed solution,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 15h to stop to 120 DEG C
Conversion ratio is surveyed in reaction；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Obtain polyurethane-modified gathering
Siloxanes.
Embodiment 4
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 22.95g and quality are end thiazolinyl polyurethane（VPU）The polymerization inhibitor phenthazine of the 0.05% of quality, quality are
The chloroplatinic acid-isopropanol of the 30ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：It is added dropwise containing 10.5g toluene and 4.92g ends thiazolinyl polyurethane with constant pressure funnel（VPU）Mixed solution,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 15h to stop to 120 DEG C
Conversion ratio is surveyed in reaction；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Obtain polyurethane-modified gathering
Siloxanes.
Embodiment 5
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 23.11g and quality are end thiazolinyl polyurethane（VPU）The polymerization inhibitor phenthazine of the 0.05% of quality, quality are
The chloroplatinic acid-isopropanol of the 40ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：It is added dropwise containing 10.5g toluene and 5.14g ends thiazolinyl polyurethane with constant pressure funnel（VPU）Mixed solution,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 15h to stop to 120 DEG C
Conversion ratio is surveyed in reaction；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Obtain polyurethane-modified gathering
Siloxanes.
Embodiment 6
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 23.28g and quality are end thiazolinyl polyurethane（VPU）The polymerization inhibitor phenthazine of the 0.05% of quality, quality are
The chloroplatinic acid-isopropanol of the 50ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：It is added dropwise containing 10.5g toluene and 5.28g ends thiazolinyl polyurethane with constant pressure funnel（VPU）Mixed solution,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keeps isothermal reaction 15h to stop to 120 DEG C
Conversion ratio is surveyed in reaction；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Obtain polyurethane-modified gathering
Siloxanes.
Claims (2)
1. a kind of polyurethane-modified polysiloxanes flax arranges the synthetic method of softening agent, it is characterised in that：The method is specifically real
Applying step is：
Step 1：Polymethyl hydrogen siloxane is added in four-hole boiling flask equipped with reflux condensing tube and the 150mL of dropping funel
16.06g, toluene 20.67g～23.28g and quality are hold thiazolinyl polyurethane VPU mass 0.05%～0.1% polymerization inhibitor
Phenthazine, quality are the chloroplatinic acid-isopropanol of the 30ppm～60ppm of graft modification monomer gross mass；
Step 2：Condensed water is opened, leads to nitrogen 5min, heating stirring makes polymethyl hydrogen siloxane be dissolved in toluene, and reaction system is warming up to
80℃；
Step 3：The mixed solution containing 10.5g toluene and end thiazolinyl polyurethane 4.17g ~ 5.14g is added dropwise with constant pressure funnel,
Control time completion of dropping in 1.5 ~ 2h, heating response system continues to stir and keep isothermal reaction to 100 DEG C ~ 120 DEG C
10h ~ 20h, stops reaction and surveys conversion ratio；Detection hydrosilylation conversion ratio, reaction conversion ratio reaches more than 93%；Gathered
The modified polysiloxanes of urethane；
Conversion ratio assay method recited above is that eudiometry determines hydrosilylation conversion ratio：
Conversion ratio (%)=[(Vo- V)/Vo] ×100%
In formula：V --- the gas flow that remaining Si-H is produced after reaction certain hour, V0--- the poly- methyl hydrogen silicon of equivalent unreacted
The gas flow that the Si-H of oxygen alkane is produced.
2. a kind of polyurethane-modified polysiloxanes flax according to claim 1 arranges the synthetic method of softening agent, and it is special
Levy and be：It is pure that described toluene, polymerization inhibitor phenthazine, chloroplatinic acid, isopropanol are analysis；It is described end thiazolinyl polyurethane, poly-
Methyl hydrogen siloxane is technical grade.
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| CN201611265847.8A CN106589387A (en) | 2016-12-31 | 2016-12-31 | Synthetic method of polyurethane modified polysiloxane flax finishing softener |
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| CN201611265847.8A CN106589387A (en) | 2016-12-31 | 2016-12-31 | Synthetic method of polyurethane modified polysiloxane flax finishing softener |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108951172A (en) * | 2018-07-19 | 2018-12-07 | 上海应用技术大学 | It is a kind of to bathe the silicone softening agent and preparation method thereof used together with fluorine system waterproofing agent |
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|---|---|---|---|---|
| CN108951172A (en) * | 2018-07-19 | 2018-12-07 | 上海应用技术大学 | It is a kind of to bathe the silicone softening agent and preparation method thereof used together with fluorine system waterproofing agent |
| CN108951172B (en) * | 2018-07-19 | 2021-05-11 | 上海应用技术大学 | Organosilicon softener used in one bath with fluorine-based waterproofing agent and preparation method thereof |
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