CN107325272A - A kind of semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule and preparation method thereof - Google Patents
A kind of semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule and preparation method thereof Download PDFInfo
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- CN107325272A CN107325272A CN201710558898.8A CN201710558898A CN107325272A CN 107325272 A CN107325272 A CN 107325272A CN 201710558898 A CN201710558898 A CN 201710558898A CN 107325272 A CN107325272 A CN 107325272A
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- melt adhesive
- type polyester
- polyester hot
- acid
- dihydric alcohol
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
- C08G63/6954—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon derived from polxycarboxylic acids and polyhydroxy compounds
- C08G63/6956—Dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a kind of semiaromatic type polyester hot-melt adhesive of block containing silicone macromolecule, it is characterised in that：The semiaromatic type polyester hot-melt adhesive of the described block containing silicone macromolecule combines preparation by following binary acid and glycol monomer：Contain the aromatic acid that at least one carbon number is 6 12 in binary acid；Containing at least one organosilicon dihydric alcohol in dihydric alcohol, at least one carbon number is 28 aliphatic dihydroxy alcohol；Wherein, the molecular weight of the organosilicon dihydric alcohol of characteristic is between 500 5000, and consumption accounts for 2 30mol% of dihydric alcohol total amount.The introducing semiaromatic type polyester hot-melt adhesive of silicone macromolecule block is reduced its glass transition temperature by the present invention, low temperature flexibility and bonding stability is improved, while improving the bond properties to resistance to viscous fabric.
Description
Technical field
The invention belongs to macromolecule polyester PUR field, and in particular to a kind of semiaromatic of block containing silicone macromolecule
Type polyester hot-melt adhesive and preparation method thereof.
Background technology
PUR is a kind of one pack system, anhydrous, solvent-free, is the adhesive of solid under normal temperature.It makees in the molten state
For the surface of adherend, and cooling when rapid curing and form splicing.As a kind of environment-friendly adhesive, in weaving
In product manufacture, it is widely used in the bonding between garment lining and fabric for a long time.This not only reduces cost, carries significantly
High workload efficiency, and make clothes endurable, tall and straight, mellow and full.
Polyester is the high molecular polymer being made up of binary acid and dihydric alcohol through polycondensation reaction.Due to polyester, particularly
The semiaromatic type polyester prepared by aromatic acid and aliphatic dihydroxy alcohol is easily crystallized, and has high intensity and durability again
Can, it is particularly suitable for use as high performance PUR.Semiaromatic type polyester hot-melt adhesive have melt fluidity it is good, solidification speed
The characteristics of degree is fast, adhesive strength is high, water resistance is excellent, and it is moderate.Therefore, semiaromatic type polyester hot-melt adhesive polyester is mesh
One of preceding the most frequently used clothes PUR.
However, most of semiaromatic type polyester hot-melt adhesive has the problem of glass transition temperature is poor compared with high and low temperature pliability.
The easy embrittlement of low temperature lower glue layer is embodied in, easy degumming cracking limits its application.The semiaromatic type polyester hot-melt adhesive of the present invention,
Because the presence of silicone macromolecule fragment in its molecular machinery reduces the glass transition temperature of PUR, make it at low temperature still
The flexibility kept, keeps the integrality and cohesive of bonding layer.On the other hand, due to the low-surface-energy of organosilicon, improve
The bond properties of polyester hot-melt adhesive viscous fabric difficult to silicon processing etc..
The content of the invention
Goal of the invention：In order to solve the deficiencies in the prior art, the invention provides a kind of block containing silicone macromolecule
Semiaromatic type polyester hot-melt adhesive and preparation method thereof.
Technical scheme：A kind of semiaromatic type polyester hot-melt adhesive of block containing silicone macromolecule, described is big containing organosilicon
The semiaromatic type polyester hot-melt adhesive of molecule blocks combines preparation by following binary acid and glycol monomer：Containing extremely in binary acid
The aromatic acid that a kind of few carbon number is 6-12；It is at least one containing at least one organosilicon dihydric alcohol in dihydric alcohol
Carbon number is 2-8 aliphatic dihydroxy alcohol；Wherein, the molecular weight of the organosilicon dihydric alcohol of characteristic is between 500-5000,
Consumption accounts for the 2-30mol% of dihydric alcohol total amount.
It is used as optimization：In order that esterification is smoothed out, the organic diol more excessive than stoichiometric amount is added, it is organic
The molar ratio example of binary acid and organic diol is 1：1-2, preferably 1:1.1-1.5.
It is used as optimization：Described organosilicon dihydric alcohol macromolecular is to contain double hydroxy-end capped multi-polysiloxanes.
It is used as optimization：The molecular weight of the organosilicon dihydric alcohol of described characteristic is between 500-2000, and consumption accounts for binary
The 2-15mol% of alcohol total amount.
It is used as optimization：Described carbon number is that 2-8 organic diol is：Ethylene glycol, propane diols, butanediol, penta 2
One or several kinds in alcohol, hexylene glycol, zinn glutaric alcohol, diglycol, triethylene-glycol, 1,6 cyclohexanedimethanols.
It is used as optimization：It is described to be for 8-12 aromatic acid plus carbon number：Terephthalic acid (TPA), isophthalic diformazan
One or several kinds in acid, 2- methyl-terephthalic acid (TPA), 2,5- dimethylformamide dimethyls acid, NDA.
It is used as optimization：Described catalyst is environmentally friendly alkyl titanate：Including butyl titanate, metatitanic acid orthocarbonate, titanium
Sour tetra-ethyl ester, the monooctyl ester of metatitanic acid four；Consumption is the 0.02-0.2%, preferably 0.03-0.08% of polyester product.
It is used as optimization：Described antioxidant is 1010 and 168 according to 1:1 ratio is added, and consumption is the 0.05- of product
0.5%, preferably 0.08-0.2%.
A kind of preparation method of the semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule described in basis, including such as
Lower step：
(1) by a certain amount of organosilicon dihydric alcohol macromonomer, organic diol, the carbon atom that carbon number is 2-8
Number is added in a reaction bulb with condensation fractionator and agitator for 8-12 organic dibasic acid and catalyst；
(2) being slowly warmed up under a nitrogen in 210-235 DEG C of progress esterification, course of reaction has water to distillate.Control evaporates
Go out temperature at 100-105 DEG C, untill the water distillated basically reaches theoretical amount；
(3) and then antioxidant and catalyst are added, 240-260 DEG C is slowly ramped to, while slowly applying the vacuum to 80Pa
Hereinafter, polycondensation reaction 1-2 hours is carried out, untill the melt index of reaction product reaches requirement, is while hot poured into product cold
Drawn in water and expect into bar, be then cut into particle.
Beneficial effect：The introducing semiaromatic type polyester hot-melt adhesive of silicone macromolecule block is reduced its glass by the present invention
Glass temperature, improves low temperature flexibility and bonding stability, while improving the bond properties to resistance to viscous fabric.
Embodiment
The technical scheme in the embodiment of the present invention will be clearly and completely described below, so that the technology of this area
Personnel can be better understood from advantages and features of the invention, so as to make apparent boundary to protection scope of the present invention
It is fixed.Embodiment described in the invention is only a part of embodiment of the invention, rather than whole embodiments, based in the present invention
Embodiment, the every other implementation that those of ordinary skill in the art are obtained on the premise of creative work is not made
Example, belongs to the scope of protection of the invention.
Embodiment
As summary, the present invention provides a kind of semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule, described
The semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule combines preparation by following binary acid and glycol monomer：Binary
Contain the aromatic acid that at least one carbon number is 6-12 in acid；Contain at least one organosilicon binary in dihydric alcohol
Alcohol, at least one carbon number is 2-8 aliphatic dihydroxy alcohol；Wherein, the molecular weight of the organosilicon dihydric alcohol of characteristic exists
Between 500-5000, consumption accounts for the 2-30mol% of dihydric alcohol total amount.
In order that esterification is smoothed out, add the organic diol more excessive than stoichiometric amount, organic dibasic acid and
Organic diol molar ratio example is 1：1-2, preferably 1:1.1-1.5.
Described organosilicon dihydric alcohol macromolecular is to contain double hydroxy-end capped multi-polysiloxanes.
The molecular weight of the organosilicon dihydric alcohol of described characteristic is between 500-2000, and consumption accounts for the 2- of dihydric alcohol total amount
15mol%.
Described carbon number is that the organic diol of 2-8 is：Ethylene glycol, propane diols, butanediol, pentanediol, oneself two
One or several kinds in alcohol, zinn glutaric alcohol, diglycol, triethylene-glycol, 1,6 cyclohexanedimethanols.
Described is that 8-12 aromatic acids are plus carbon number：Terephthalic acid (TPA), M-phthalic acid, 2- methyl-
One or several kinds in terephthalic acid (TPA), 2,5- dimethylformamide dimethyls acid, NDA.
Described catalyst is environmentally friendly metatitanic acid alkyl：Including butyl titanate, metatitanic acid orthocarbonate, tetraethyl titanate, titanium
Sour four monooctyl esters；Consumption is the 0.02-0.2%, preferably 0.03-0.08% of polyester product.
Described antioxidant is 1010 and 168 according to 1:1 ratio is added, and consumption is the 0.05-0.5% of product, preferably
For 0.08-0.2%.
Example 1：Polyester hot-melt adhesive A
By 163g (0.98mol) terephthalic acid (TPA), 70g (0.42mol) M-phthalic acid, 152g (1.69mol) butanediol,
113g (0.75mol) triethylene-glycol, 90g (molecular weight 1500,0.06mol) organosilicon dihydric alcohol macromoleculars and 0.1g metatitanic acids
Four butyl esters are added in a reaction bulb with condensation fractionator and agitator.210-235 DEG C is slowly warmed up under a nitrogen
Carry out thering is water to distillate in esterification, course of reaction.Recovered (distilled) temperature is controlled at 100-105 DEG C, until the water distillated reaches substantially
Untill theoretical amount.Then antioxidant 0.4g and 0.12g butyl titanate is added, 240-260 DEG C is slowly ramped to, while slowly
Below 80Pa is applied the vacuum to, polycondensation reaction 1-2 hours is carried out, untill the melt index of reaction product reaches requirement, takes advantage of
Heat, which pours into product to draw in cold water, expects into bar, obtains the semiaromatic type polyester hot-melt adhesive A of the block containing silicone macromolecule.Through DSC
Determine, PUR A fusing point is 118 DEG C.Show that PUR A films 100 microns thick have still been kept at 0 DEG C using test
Flexibility, and the bond properties that fabric has had is handled silicon.
Example 2：Polyester hot-melt adhesive B
By 270g (1.62mol) terephthalic acid (TPA), 30g (0.18mol) M-phthalic acid, 91g (1.01mol) butanediol,
143g (1.21mol) hexylene glycol, 88g (molecular weight 500,0.18mol) organosilicon dihydric alcohol macromoleculars and 0.1g butyl titanates
It is added in a reaction bulb with condensation fractionator and agitator.210-235 DEG C of progress ester is slowly warmed up under a nitrogen
Changing in reaction, course of reaction has water to distillate.Recovered (distilled) temperature is controlled at 100-105 DEG C, until the water distillated basically reaches theory
Untill amount.Then 0.5g antioxidant and 0.1g butyl titanates are added, 240-260 DEG C is slowly ramped to, while slowly applying true
It is empty to carry out polycondensation reaction 1-2 hours to below 80Pa, while hot will production untill the melt index of reaction product reaches requirement
Thing, which pours into draw in cold water, expects into bar, obtains the semiaromatic type polyester hot-melt adhesive B of the block containing silicone macromolecule.Determined through DSC, heat
Melten gel B fusing point is 127 DEG C.Show using test, PUR B films 100 microns thick, the flexibility still kept at 0 DEG C,
And the bond properties that fabric has had is handled silicon.
Example 3：Polyester hot-melt adhesive C
By 249g (1.5mol) terephthalic acid (TPA), 98g (1.10mol) butanediol, 89g (0.84mol) diglycol,
120g (molecular weight 1000,0.12mol) organosilicon dihydric alcohol macromoleculars and 0.1g butyl titanates are added to one with condensation
In the reaction bulb of fractionator and agitator.Being slowly warmed up under a nitrogen in 210-235 DEG C of progress esterification, course of reaction has
Water is distillated.Recovered (distilled) temperature is controlled at 100-105 DEG C, untill the water distillated basically reaches theoretical amount.Then 0.5g is added
Antioxidant and 0.1g butyl titanates, are slowly ramped to 240-260 DEG C, while slowly applying the vacuum to below 80Pa, are contracted
Poly- reaction 1-2 hours, product untill the melt index of reaction product reaches requirement, poured into draw in cold water and expected into while hot
Bar, obtains the semiaromatic type polyester hot-melt adhesive C of the block containing silicone macromolecule.Determined through DSC, PUR C fusing point is 111
℃.Show using test, PUR C films 100 microns thick, the flexibility still kept at 0 DEG C, and to silicon processing fabric tool
The bond properties having had.
Claims (9)
1. a kind of semiaromatic type polyester hot-melt adhesive of block containing silicone macromolecule, it is characterised in that：Described is big containing organosilicon
The semiaromatic type polyester hot-melt adhesive of molecule blocks combines preparation by following binary acid and glycol monomer：Containing extremely in binary acid
The aromatic acid that a kind of few carbon number is 6-12；It is at least one containing at least one organosilicon dihydric alcohol in dihydric alcohol
Carbon number is 2-8 aliphatic dihydroxy alcohol；Wherein, the molecular weight of the organosilicon dihydric alcohol of characteristic is between 500-5000,
Consumption accounts for the 2-30mol% of dihydric alcohol total amount.
2. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：For
Esterification is smoothed out, the organic diol more excessive than stoichiometric amount, organic dibasic acid and organic diol is added
Molar ratio example be 1：1-2, preferably 1:1.1-1.5.
3. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：Institute
The organosilicon dihydric alcohol macromolecular stated is containing double hydroxy-end capped multi-polysiloxanes.
4. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：Institute
The molecular weight of the organosilicon dihydric alcohol for the characteristic stated is between 500-2000, and consumption accounts for the 2-15mol% of dihydric alcohol total amount.
5. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：Institute
The carbon number stated is that the organic diol of 2-8 is：Ethylene glycol, propane diols, butanediol, pentanediol, hexylene glycol, pungent penta 2
One or several kinds in alcohol, diglycol, triethylene-glycol, 1,6 cyclohexanedimethanols.
6. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：Institute
The carbon number stated is that 8-12 aromatic acid is：Terephthalic acid (TPA), M-phthalic acid, 2- methyl-terephthalic acid (TPA), 2,
One or several kinds in 5- dimethylformamide dimethyls acid, 2,6- naphthalenedicarboxylic acids.
7. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：Institute
The catalyst stated is environmentally friendly alkyl titanate:Including butyl titanate, metatitanic acid orthocarbonate, tetraethyl titanate, the monooctyl ester of metatitanic acid four；
Consumption is the 0.02-0.2%, preferably 0.03-0.08% of polyester product.
8. the semiaromatic type polyester hot-melt adhesive of the block according to claim 1 containing silicone macromolecule, it is characterised in that：Institute
The antioxidant stated is 1010 and 168 according to 1:1 ratio is added, and consumption is the 0.05-0.5%, preferably 0.08- of product
0.2%.
9. a kind of preparation side of the semiaromatic type polyester hot-melt adhesive of block according to claim 1 containing silicone macromolecule
Method, it is characterised in that：Comprise the following steps：
(1) organic diol for being 2-8 by a certain amount of organosilicon dihydric alcohol macromonomer, carbon number, carbon number are
8-12 organic dibasic acid and catalyst is added in a reaction bulb with condensation fractionator and agitator；
(2) being slowly warmed up under a nitrogen in 210-235 DEG C of progress esterification, course of reaction has water to distillate.Control distillates temperature
Degree is at 100-105 DEG C, untill the water distillated basically reaches theoretical amount；
(3) and then antioxidant and catalyst are added, is slowly ramped to 240-260 DEG C, while below 80Pa is slowly applied the vacuum to,
Polycondensation reaction 1-2 hours is carried out, untill the melt index of reaction product reaches requirement, product is poured into cold water drawn while hot
Expect into bar, be then cut into particle.
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| CN201710558898.8A CN107325272A (en) | 2017-07-11 | 2017-07-11 | A kind of semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule and preparation method thereof |
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| CN201710558898.8A CN107325272A (en) | 2017-07-11 | 2017-07-11 | A kind of semiaromatic type polyester hot-melt adhesive of the block containing silicone macromolecule and preparation method thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108300394A (en) * | 2018-01-22 | 2018-07-20 | 储微微 | One kind is based on pet waste production polyester hot-melt adhesive and preparation method thereof |
| WO2019062428A1 (en) * | 2017-09-27 | 2019-04-04 | 南通星辰合成材料有限公司 | Polyester segmented copolymer and preparation method therefor and application thereof |
| CN113683763A (en) * | 2021-10-26 | 2021-11-23 | 江苏金发科技新材料有限公司 | Semi-aromatic polyester and preparation method and application thereof |
| CN114181654A (en) * | 2021-12-21 | 2022-03-15 | 上海东睿化学有限公司 | Biodegradable copolyester hot melt adhesive and preparation method thereof |
| CN115612080A (en) * | 2021-07-14 | 2023-01-17 | 华润化学材料科技股份有限公司 | Silicon-containing polyester and preparation method thereof |
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| CN101497775A (en) * | 2008-02-02 | 2009-08-05 | 上海轻工业研究所有限公司 | Preparation of hydrolysis resisting polyester hot-melt adhesive |
| CN105670546A (en) * | 2014-11-17 | 2016-06-15 | 上海理日化工新材料有限公司 | Polyether ester hot-melt adhesive and preparation method thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101497775A (en) * | 2008-02-02 | 2009-08-05 | 上海轻工业研究所有限公司 | Preparation of hydrolysis resisting polyester hot-melt adhesive |
| CN105670546A (en) * | 2014-11-17 | 2016-06-15 | 上海理日化工新材料有限公司 | Polyether ester hot-melt adhesive and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019062428A1 (en) * | 2017-09-27 | 2019-04-04 | 南通星辰合成材料有限公司 | Polyester segmented copolymer and preparation method therefor and application thereof |
| CN108300394A (en) * | 2018-01-22 | 2018-07-20 | 储微微 | One kind is based on pet waste production polyester hot-melt adhesive and preparation method thereof |
| CN115612080A (en) * | 2021-07-14 | 2023-01-17 | 华润化学材料科技股份有限公司 | Silicon-containing polyester and preparation method thereof |
| CN113683763A (en) * | 2021-10-26 | 2021-11-23 | 江苏金发科技新材料有限公司 | Semi-aromatic polyester and preparation method and application thereof |
| CN114181654A (en) * | 2021-12-21 | 2022-03-15 | 上海东睿化学有限公司 | Biodegradable copolyester hot melt adhesive and preparation method thereof |
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Application publication date: 20171107 |