CN105906790B - A kind of PEPA for synthesizing damp solidifying polyurethane PUR - Google Patents
A kind of PEPA for synthesizing damp solidifying polyurethane PUR Download PDFInfo
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- CN105906790B CN105906790B CN201610295428.2A CN201610295428A CN105906790B CN 105906790 B CN105906790 B CN 105906790B CN 201610295428 A CN201610295428 A CN 201610295428A CN 105906790 B CN105906790 B CN 105906790B
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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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to a kind of PEPA with special construction, more particularly to a kind of PEPA for being used to synthesize damp solidifying polyurethane PUR.It is prepared by tri- kinds of monomers of A, B, C by esterification, wherein A is at least one long linear binary acid, and the long linear binary acid refers to the Straight chain diatomic acid containing more than 8 carbon atoms in carbochain；B is at least one long linear dihydric alcohol, and the long linear dihydric alcohol refers to the straight dihydric alcohol containing more than 5 carbon atoms in carbochain；C is at least one long-chain branch dihydric alcohol, and the long-chain branch dihydric alcohol refers to the dihydric alcohol with linear normal carbon chain and at least one long branched chain structure, and the long branched chain structure refers to the carbochain for including more than 2 methylene.Polyester synthesized by the present invention, there is high molecular weight and low normal temperature viscosity.Using polyester of the present invention, on the premise of isocyanate content is not increased, the extremely low polyurethane hot melt of generation melting viscosity can be reacted with isocyanates.
Description
Technical field
It is more particularly to a kind of to gather for synthesizing moisture-curable the present invention relates to a kind of PEPA with special construction
The PEPA of urethane PUR.
Background technology
Moisture-curable polyurethane hot-melt glue is a kind of High performance hot melt adhesive product largely used at present.Such polyurethane
The main component of PUR is the polyester diol by 1000~5000g/mol of molecular weight（Abbreviation polyester）, with isocyanation esterification
The isocyanate-terminated polyurethane prepolymer of compound reaction generation.The prepolymer has thermal fluidity, and quilt is coated on after heating
The surface of viscous thing, crosslinking curing is carried out by the moisture in air, forms bonding.
Because such adhesive has the characteristic of heating coating, therefore it is one important finger of such adhesive to heat viscosity
Mark.It is to improve the melt adhesive temperature of melten gel equipment to reduce the usual way of polyurethane-hot melt viscosity, such as molten from common 100 ~ 130 DEG C
Glue, 150 ~ 180 DEG C of melten gels are brought up to, can so reduce the melting viscosity of colloid.The problem of this method is brought be：Due to glue
The reactive isocyanate groups in internal portion are under the high temperature conditions（More than 130 DEG C）It is chemically crosslinked, causes the ripple of melten gel viscosity
Dynamic even rapid increase, while high melt adhesive temperature makes colloid easily cause adherend when being coated in the adherend surface of thermal sensitivity
Heated modification.
Also it can obtain relatively low hot melt by improving the isocyanate content inside damp solidifying polyurethane PUR and stick
Degree.The problem of this method is brought be：High isocyanate content makes the time lengthening of moisture-curable after colloid coating, Er Qiegu
More bubbles are produced during change.Also can be by using the polyester of low molecule amount（Hydroxyl value such as polyester is more than 160mg/KOH, average mark
Son amount is less than 700g/mol）Raw material synthesize damp solidifying polyurethane PUR, to obtain relatively low colloid viscosity.But by
Excessive isocyanates is consumed in, hydroxyl value height low using molecular weight of polyesters, building-up process, causes damp solidifying polyurethane to heat
The hardness of glue is greatly increased, and free isocyanate increases, and bubble is produced during moisture-curable and is significantly increased, this is also to connect
Receive.
Use higher molecular weight（As hydroxyl value is less than 30mg/KOH, mean molecule quantity is more than 3500g/mol）Polyester synthesis
Damp solidifying polyurethane PUR, suitable isocyanate content can be obtained（If NCO% is 2 to 5）With good moisture-curable
Effect, but polyester viscosity itself is very big, causes the damp solidifying polyurethane hot melt gumminess of synthesis also corresponding very big, coats tired
It is difficult.Therefore, in order to synthesize the preferable damp solidifying polyurethane PUR of melting viscosity, the macromolecule with compared with low-viscosity is developed
Weight polyester raw material, it is the direction to solve the above problems.
The content of the invention
In order to overcome above-mentioned technical shortcoming and deficiency, it is an object of the invention to provide a kind of HMW, eutectic
Melt the PEPA for being used to synthesize damp solidifying polyurethane PUR of viscosity.
The PEPA of the present invention for being used to synthesize damp solidifying polyurethane PUR, is led to by tri- kinds of monomers of A, B, C
Over-churning reaction is prepared, and wherein A is at least one long linear binary acid, and the long linear binary acid refers to contain 8 in carbochain
The Straight chain diatomic acid of individual above carbon atom；B is at least one long linear dihydric alcohol, and the long linear dihydric alcohol refers to contain in carbochain
The straight dihydric alcohol of more than 5 carbon atoms；C is at least one long-chain branch dihydric alcohol；The long-chain branch dihydric alcohol refers to have linearly
The dihydric alcohol of normal carbon chain and at least one long branched chain structure, the long branched chain structure refer to the carbochain for including more than 2 methylene；
The acid-alcohol ratio of tri- kinds of monomers of A, B, C is less than 1.3.
Preferably, the acid-alcohol ratio of tri- kinds of monomers of A, B, C is 1.08 ~ 1.20.During esterification, using appropriate hydroxyl
The molar ratio of substratess matter and carboxyl material（Abbreviation acid-alcohol ratio）, and system hydroxyl value is constantly determined during the course of the reaction, to obtain
The polyester product of similar mass, to obtain the polyester product with higher molecular weight, acid-alcohol ratio should be less than 1.3, preferably 1.08 ~
Between 1.20.
Preferably, at least one long linear binary acid is 1,8- suberic acids, and 1,9- azelaic acid, 1,10- SA,
At least one of 1,11- heneicosanedioic acid 1,12 dodecanedioic acids.
As further preferred, at least one long linear binary acid is 1,10- SAs, 1,11- heneicosanedioic acid
The mixed dibasic acid of 1,12 dodecanedioic acid.
Preferably, at least one long linear dihydric alcohol is 1,5-PD, and 1,6- hexylene glycol, 1,7- heptandiol,
At least one of 1,8- ethohexadiol, 1,9- nonanediol, 1,10- certain herbaceous plants with big flowers glycol.
As further preferred, at least one long linear dihydric alcohol is 1,5-PD.
Preferably, at least one long-chain branch dihydric alcohol is 2,4- diethyl -1,5-PD, 2- diethyl -1,
At least one of 3- hexylene glycols, 2- butyl -2- ethyl glycols.
As further preferred, at least one long-chain branch dihydric alcohol is 2- butyl -2- ethyl glycols.
The advantage of the invention is that:Using long linear binary acid, this kind of long linear binary acid is due to two end carboxyl intervals
Carbon atom number is more, and the polyester ester group density obtained after being reacted with alcohols is low, therefore has relatively low viscosity；It is preferred that using mixed
Long linear binary acid is closed, because mixing long linear binary acid has higher irregular degree and relatively low carboxyl density, can be synthesized
The relatively low polyester of ester output base density, so as to obtain relatively low viscosity.Using long linear dihydric alcohol, due to two terminal hydroxy group interval carbon
Atom number is more, and the polyester ester group density obtained after being reacted with acids is low, therefore has relatively low viscosity；It is preferred that use 1,5-
Pentanediol, because 1,5-PD has the carbon-chain structure of uneven number carbon atom, the polyester of more low-crystallinity can be synthesized, so as to
To the polyester of more low-viscosity.Using long-chain branch dihydric alcohol, this kind of long-chain branch dihydric alcohol can be dropped due to the space steric effect of side chain
Mutual winding between oligoester strand, so as to obtain compared with low-viscosity.Polyester synthesized by the present invention, there is high molecular weight
With low normal temperature viscosity.Using polyester of the present invention, on the premise of isocyanate content is not increased, can and isocyanic acid
The extremely low polyurethane hot melt of ester reaction generation melting viscosity.
Embodiment
The synthesis of PEPA
Embodiment 1
Added into reactors equipped with thermometer, agitator and condensing unit of the 1000mL with vacuum dewatering plant
The Corfree M1 mixed acid 500g of Invista companies（Main component is 1,10- SAs, 1,11- heneicosanedioic acid 1,12-
The mixture of dodecanedioic acid, the g/mol of mean molecule quantity 220）, 1,5-PD 200g, 2- butyl -2- ethyl glycols
120g, acid-alcohol ratio 1.18, heating start simultaneously at stirring；When being warming up to 190 DEG C, start to distillate moisture, be continuously heating to interior
Temperature reaches 220 DEG C, when water to be distillated is close to theoretical amount, and measure hydroxyl value starts decompression and steams reaction generation when being less than 15mg/KOH
Oligomer and unnecessary alcohol, when distillate reduce or it is slack-off when, decompression carry out high vacuum reaction, system pressure be maintained at 80Pa with
Under, after 3 hours reaction time, hydroxyl value is constantly measured by sampling, when hydroxyl value reaches 24mg/KOH polycondensation reaction terminate.Protected in nitrogen
Under shield, release Vacuum discharge and obtain PEPA P1.The molecular weight of polyesters about 4700g/mol is determined, 25 DEG C of viscosity is
6500cP。
Embodiment 2
Added into reactors equipped with thermometer, agitator and condensing unit of the 1000mL with vacuum dewatering plant
The Corfree M1 mixed acid 500g of Invista companies（Main component is 1,10- SAs, 1,11- heneicosanedioic acid 1,12-
The mixture of dodecanedioic acid, the g/mol of mean molecule quantity 220）, 1,5-PD 120g, 2- butyl -2- ethyl glycols
230g, acid-alcohol ratio 1.14, heating start simultaneously at stirring；When being warming up to 190 DEG C, start to distillate moisture, be continuously heating to interior
Temperature reaches 220 DEG C, when water to be distillated is close to theoretical amount, and measure hydroxyl value starts decompression and steams reaction generation when being less than 15mg/KOH
Oligomer and unnecessary alcohol, when distillate reduce or it is slack-off when, decompression carry out high vacuum reaction, system pressure be maintained at 80Pa with
Under, after 3 hours reaction time, hydroxyl value is constantly measured by sampling, when hydroxyl value reaches 24mg/KOH polycondensation reaction terminate.Protected in nitrogen
Under shield, release Vacuum discharge and obtain PEPA P2.The molecular weight of polyesters about 4700g/mol, 25 DEG C of viscosity is 5000cP.
Embodiment 3
1 is added into reactors equipped with thermometer, agitator and condensing unit of the 1000mL with vacuum dewatering plant,
11- heneicosanedioic acids 500g, 1,6- hexylene glycol 200g, 2,4- diethyl -1,5-PD 150g, acid-alcohol ratio 1.14, heating is together
When start to stir；When being warming up to 190 DEG C, start to distillate moisture, be continuously heating to interior temperature and reach 220 DEG C, water to be distillated connects
During nearly theoretical amount, measure hydroxyl value starts decompression when being less than 15mg/KOH and steams oligomer and the unnecessary alcohol that reaction generates, when distillating
When thing reduces or be slack-off, decompression carries out high vacuum reaction, and system pressure is maintained at below 80Pa, after 3 hours reaction time, constantly
Be measured by sampling hydroxyl value, when hydroxyl value reaches 24mg/KOH polycondensation reaction terminate.Under nitrogen protection, Vacuum discharge is released to be gathered
Ester polyol P3.The molecular weight of polyesters about 4700g/mol is determined, 25 DEG C of viscosity is 7000cP.
Embodiment 4
1 is added into reactors equipped with thermometer, agitator and condensing unit of the 1000mL with vacuum dewatering plant,
11- heneicosanedioic acids and 1,12 dodecanedioic acid mixed acid（1：1）500g, 1,5-PD 60g, 1,6- hexylene glycol 60g,
2- diethyl -1,3- hexylene glycol 230g, acid-alcohol ratio 1.18, heating start simultaneously at stirring；When being warming up to 190 DEG C, start to distillate
Moisture, it is continuously heating to interior temperature and reaches 220 DEG C, when water to be distillated is close to theoretical amount, measure hydroxyl value is opened when being less than 15mg/KOH
Begin to depressurize the oligomer for steaming reaction generation and unnecessary alcohol, when distillate reduces or be slack-off, decompression progress high vacuum reaction, be
System pressure is maintained at below 80Pa, and after 3 hours reaction time, hydroxyl value is constantly measured by sampling, is contracted when hydroxyl value reaches 24mg/KOH
Poly- reaction terminates.Under nitrogen protection, release Vacuum discharge and obtain PEPA P4.The molecular weight of polyesters about 4700g/mol,
25 DEG C of viscosity is 7800cP.
Comparative example 1
Oneself is added into reactors equipped with thermometer, agitator and condensing unit of the 1000mL with vacuum dewatering plant
Diacid 300g, diethylene glycol 246g, acid-alcohol ratio 1.13, heating start simultaneously at stirring；When being warming up to 190 DEG C, start to distillate water
Point, it is continuously heating to interior temperature and reaches 220 DEG C, when water to be distillated is close to theoretical amount, measure hydroxyl value starts when being less than 15mg/KOH
Decompression steams the oligomer of reaction generation and unnecessary alcohol, and when distillate reduces or be slack-off, decompression carries out high vacuum reaction, system
Pressure is maintained at below 80Pa, and after 3 hours reaction time, hydroxyl value is constantly measured by sampling, the polycondensation when hydroxyl value reaches 24mg/KOH
Reaction terminates.Under nitrogen protection, release Vacuum discharge and obtain PEPA P5.Determine the molecular weight of polyesters about 4700g/
Mol, 25 DEG C of viscosity is 15000cP.
Comparative example 2
Oneself is added into reactors equipped with thermometer, agitator and condensing unit of the 1000mL with vacuum dewatering plant
Diacid 300g, 2- methyl isophthalic acid, ammediol 210g, acid-alcohol ratio 1.13, heating start simultaneously at stirring；When being warming up to 190 DEG C, open
Beginning distillates moisture, is continuously heating to interior temperature and reaches 220 DEG C, when water to be distillated is close to theoretical amount, measure hydroxyl value is less than 15mg/
Start decompression during KOH and steam the oligomer of reaction generation and unnecessary alcohol, when distillate reduces or be slack-off, decompression carries out high vacuum
Reaction, system pressure is maintained at below 80Pa, after 3 hours reaction time, hydroxyl value is constantly measured by sampling, when hydroxyl value reaches 24mg/
Polycondensation reaction terminates during KOH.Under nitrogen protection, release Vacuum discharge and obtain PEPA P6.Determine the molecular weight of polyesters
About 4700g/mol, 25 DEG C of viscosity is 20000cP.
The synthesis of polyurethane hot melt
Embodiment 5
200g PEPA P1 are put into 500mL reactor, 4, the 4- diphenyl methanes two for then adding 30g are different
Cyanate（4,4-MDI）, 80 DEG C of insulation reactions 2.5 hours；Then 0.5g catalyst dibutyltins dilaurylate is put into continue instead
After answering 1 hour, gained performed polymer is polyurethane hot melt.It is 2.71% to titrate its nco value, and 120 DEG C of viscositys are 1800cP.
Embodiment 6
200g PEPA P2 are put into 500mL reactor, 4, the 4- diphenyl methanes two for then adding 30g are different
Cyanate（4,4-MDI）, 80 DEG C of insulation reactions 2.5 hours；Then 0.5g catalyst dibutyltins dilaurylate is put into continue instead
After answering 1 hour, gained performed polymer is polyurethane hot melt.It is 2.68% to titrate its nco value, and 120 DEG C of viscositys are 1600cP.
Embodiment 7
200g PEPA P3 are put into 500mL reactor, 4, the 4- diphenyl methanes two for then adding 30g are different
Cyanate（4,4-MDI）, 80 DEG C of insulation reactions 2.5 hours；Then 0.5g catalyst dibutyltins dilaurylate is put into continue instead
After answering 1 hour, gained performed polymer is polyurethane hot melt.It is 2.69% to titrate its nco value, and 120 DEG C of viscositys are 1900cP.
Embodiment 8
200g PEPA P4 are put into 500mL reactor, 4, the 4- diphenyl methanes two for then adding 30g are different
Cyanate（4,4-MDI）, 80 DEG C of insulation reactions 2.5 hours；Then 0.5g catalyst dibutyltins dilaurylate is put into continue instead
After answering 1 hour, gained performed polymer is polyurethane hot melt.It is 2.70% to titrate its nco value, and 120 DEG C of viscositys are 2000cP.
Comparative example 3
200g PEPA P5 are put into 500mL reactor, 4, the 4- diphenyl methanes two for then adding 30g are different
Cyanate（4,4-MDI）, 80 DEG C of insulation reactions 2.5 hours；Then 0.5g catalyst dibutyltins dilaurylate is put into continue instead
After answering 1 hour, gained performed polymer is polyurethane hot melt.It is 2.65% to titrate its nco value, and 120 DEG C of viscositys are 10000cP.
Comparative example 4
200g PEPA P6 are put into 500mL reactor, 4, the 4- diphenyl methanes two for then adding 30g are different
Cyanate（4,4-MDI）, 80 DEG C of insulation reactions 2.5 hours；Then 0.5g catalyst dibutyltins dilaurylate is put into continue instead
After answering 1 hour, gained performed polymer is polyurethane hot melt.It is 2.76% to titrate its nco value, and 120 DEG C of viscositys are 14000cP.
As can be seen that the polyester of the special construction of the present invention from embodiment 1-4 and comparative example 1,2, in identical hydroxyl value and
Under the conditions of molecular weight, there is relatively low viscosity；As can be seen that being closed using polyester of the present invention from embodiment 5-8 and comparative example 3,4
Into the polyurethane hot melt gone out, with lower melting viscosity at 120 DEG C, by making in isocyanate value under the same conditions
The effect that damp solidifying polyurethane PUR melting viscosity is reduced with the polyester of the present invention is apparent.
Claims (3)
- A kind of 1. PEPA for being used to synthesize damp solidifying polyurethane PUR, it is characterised in that：The PEPA It is prepared by tri- kinds of monomers of A, B, C by esterification, wherein A is 1,10- decanedioic acid, 1,11- heneicosanedioic acids, 1,12- The mixed dibasic acid of dodecanedioic acid；B is 1,5- pentanediols；C is 2,4- diethyl -1,5-PD, 2- ethyls -1,3- oneself two At least one of alcohol, 2- butyl -2- ethyl glycols；The acid-alcohol ratio of tri- kinds of monomers of A, B, C is less than 1.3.
- 2. a kind of PEPA for being used to synthesize damp solidifying polyurethane PUR according to claim 1, its feature It is：The acid-alcohol ratio of tri- kinds of monomers of A, B, C is 1.08 ~ 1.20.
- 3. a kind of PEPA for being used to synthesize damp solidifying polyurethane PUR according to claim 1 or 2, it is special Sign is：The C is 2- butyl -2- ethyl glycols.
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| CN109180915B (en) * | 2018-08-03 | 2020-10-23 | 山东一诺威聚氨酯股份有限公司 | Liquid polyester polyol for polyurethane coating and preparation method and application thereof |
| CN109735285A (en) * | 2019-01-07 | 2019-05-10 | 上海灼日新材料科技有限公司 | A kind of high-accuracy electronics PUR hot melt adhesive and preparation method thereof |
| CN110092893A (en) * | 2019-05-22 | 2019-08-06 | 无锡风鹏新材料科技有限公司 | A kind of room temperature liquid polyesters and preparation method thereof |
| CN112300745B (en) * | 2019-08-02 | 2022-07-12 | 万华化学（北京）有限公司 | Moisture-curing reaction type polyurethane hot melt adhesive and preparation method thereof |
| CN112708386A (en) * | 2020-12-24 | 2021-04-27 | 上海回天新材料有限公司 | Solvent-free single-component moisture-curing polyurethane adhesive for paper-plastic compounding and preparation method thereof |
| CN113528076A (en) * | 2020-12-31 | 2021-10-22 | 上海回天新材料有限公司 | Solvent-free single-component moisture-curing polyurethane adhesive for wearable equipment and preparation method thereof |
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| JP2627834B2 (en) * | 1991-07-26 | 1997-07-09 | 日本ポリウレタン工業株式会社 | Reactive hot melt adhesive |
| US7612151B2 (en) * | 2004-04-09 | 2009-11-03 | Dainippon Ink And Chemicals, Inc. | Moisture-curable polyurethane hot-melt adhesive |
| JP2015038162A (en) * | 2010-04-20 | 2015-02-26 | 日本ビー・ケミカル株式会社 | Polyester resin and application of the same |
| JP5787202B2 (en) * | 2013-09-06 | 2015-09-30 | Dic株式会社 | Polyester polyol, polyol agent for laminating adhesive, resin composition, curable resin composition, laminating adhesive, and solar cell backsheet |
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Denomination of invention: Polyester polyol for synthesizing moisture curing polyurethane hot melt adhesive Effective date of registration: 20211013 Granted publication date: 20171222 Pledgee: Zhejiang Tongxiang rural commercial bank Limited by Share Ltd. Shimen branch Pledgor: ZHEJIANG JOYA POLYMER TECHNOLOGY Co.,Ltd. Registration number: Y2021330001883 |
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