CN1635014A - Low molecular polyamide modified hot melt adhesive and method for preparation - Google Patents
Low molecular polyamide modified hot melt adhesive and method for preparation Download PDFInfo
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- CN1635014A CN1635014A CN 200410066137 CN200410066137A CN1635014A CN 1635014 A CN1635014 A CN 1635014A CN 200410066137 CN200410066137 CN 200410066137 CN 200410066137 A CN200410066137 A CN 200410066137A CN 1635014 A CN1635014 A CN 1635014A
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- hot melt
- melt adhesive
- low
- grafting
- molecular polyamide
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 41
- 229920002647 polyamide Polymers 0.000 title claims abstract description 41
- 239000004831 Hot glue Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000004132 cross linking Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 150000002009 diols Chemical group 0.000 claims 2
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 229920002521 macromolecule Polymers 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 3
- 150000004985 diamines Chemical class 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 12
- -1 aliphatic diamines Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910017108 Fe—Fe Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 238000012660 binary copolymerization Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012704 multi-component copolymerization Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Landscapes
- Polyamides (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a low molecule polyamide modified hot melt adhesive and its preparation method. The preparation method comprises proportionally charging the low molecule polyamide and grafting agent into a reaction still with vacuum and condenser system, stirring, increasing the temperature, and grafting to obtain a prepolymer, then vacuumizing, lowering the temperature, and proportionally charging the crosslinking agent, increasing the temperature to react for hours and obtain the low molecule polyamide modified hot melt adhesive. The invention has advantages of no pollution, no solvent recovery and product purification, and simple process. The raw material employs homemade 010 resin or 011 resin which has low-cost and plentiful sources. The softening point and viscosity of the low molecule polyamide modified hot melt adhesive can be regulated by changing technological conditions, and the flexibility can be improved by replacing the diamine with diatomic alcohol or polyatomic alcohol to reduce the chances of forming hydrogen bond in macromolecule.
Description
Technical Field
The invention relates to polyesteramide with hot melt adhesive property, in particular to a low molecular polyamide modified hot melt adhesive and a preparation method thereof.
Background
Polyamide hotmelt adhesives which generally have a relatively high softening point and a relatively good flow are usually obtained by binary or multicomponent copolymerization of aromatic diacids and aromatic or aliphatic diamines. Such as JP59-125483 and U.S. Pat. No. 3, 5089588, both use polyamides with phenyl as the main structure. In the above patent, the polymer molecule contains many rigid benzene ring structures, so that the flexibility of the product is reduced. In addition, solvent polymerization is generally adopted in the methods, so that the problems of product purification, solvent recovery and the like are brought in the production, and certain environmental pollution is caused.
Chinese patent 94116955.3 overcomes the disadvantages of the above patents and introduces a synthesis of polyamide hot melt adhesive, which is characterized in that random polyamide is used as basic raw material, polymerized with long-chain aliphatic dibasic acid, and partially crosslinked with aliphatic diamine to obtain hot melt polyamide. The method adopts bulk polymerization, solves the problem of environmental pollution in production, and improves the flexibility of the product. However, the method adopts long-chain aliphatic diacid, which is easy to migrate and recrystallize during the storage process of the product, and the orientation crystallization tendency of even-number long-chain aliphatic diacid is more serious, so that the flexibility of the product is reduced. In addition, a large number of hydrogen bonds are generated between amide bonds of macromolecules, which are factors for reducing the flexibility of products, and the formula is as follows:
in addition, the polyamide hot melt adhesive introduced in chinese patent 01106037.9 is prepared by polymerizing polyamide a as a basic raw material with aliphatic dibasic acid B to form C, and then performing a crosslinking reaction with aliphatic diamine E, and is characterized in that: adding a chemical toughening agent D for toughening reaction before the reaction of C and E. The toughening agent is polyether or rubber with active group. This not only complicates the process, but also increases the cost.
Disclosure of Invention
Aiming at the defects and shortcomings in the prior art, the invention aims to improve the flexibility of the product, adjust the softening point and viscosity, improve the high-temperature oxidation resistance, reduce the cost of raw materials, simplify the production process and solve the environmental pollution.
The invention aims to provide an anti-oxidation flame-retardant low-molecular-weight polyamide modified hot melt adhesive with good toughness and high softening point and a preparation method thereof on the basis of Chinese patent 94116955.3 and Chinese patent 01106037.9.
The low molecular polyamide modified hot melt adhesive is characterized by having the following repeating unit structure:
wherein: r1As dimer acid, R2Is- (CH)2)-2-12，R3Is- (CH)2)-6-13，R4Is- (CH) having a molecular weight of 60-20002) -or- (C)2H4O)nCH2-。
The method for preparing the low molecular polyamide modified hot melt adhesive is to modify low molecular polyamide through two steps of grafting and crosslinking, and comprises the following specific steps: firstly, adding low-molecular polyamide and a grafting agent into a reaction kettle with a vacuum and condensation system in proportion, heating while stirring for grafting reaction to obtain a prepolymer, vacuumizing, cooling, adding a crosslinking agent in proportion, heating for reaction for several hours, and performing crosslinking reaction to obtain the low-molecular polyamide modified hot melt adhesive. The low molecular polyamide suitable for the invention is domestic 010 resin or 011 resin; the grafting agent is aliphatic saturated dibasic acid or unsaturated dibasic acid, and the number of carbon atoms is 6-13; the cross-linking agent is single alcohol or mixed alcohol, and the molecular weight of the cross-linking agent is 60-2000; wherein it can be dihydric alcohol or polyhydric alcohol or polymeric dihydric alcohol; the raw material ratio is as follows: the low molecular polyamide, the grafting agent and the crosslinking agent are 1: 0.4-2.2: 0.2-2.0 (mol), and the synthesis conditions are as follows: the vacuum degree is 0.05-0.1 MPa; the reaction temperature is 150-300 ℃; the reaction time is 1-11 h.
The first step is as follows:
the second step is that:
the third step: and (4) carrying out proper adjustment according to the requirements of different users to obtain products suitable for application in different fields.
The condensation product of 010 resin dimerized oleic acid and aliphatic diamine has active hydrogen on the amide group N atom in the molecule catalyzed by catalyst to react with grafting agent to branch the molecule at certain temperature to produce reactive pre-polymer capable of further condensing with crosslinking agent to increase molecular weight and form, and has greatly raised toughness and thus raised softening point and viscosity.
The substance prepared by the method is detected, and the performance results are as follows:
| item | Range of |
| Viscosity mPa.S/190 deg.C | 1000～10000 |
| Softening point of | 100～170 |
| Volume resistance omega cm | ≥1×1012 |
| Breakdown voltage KV/mm | ≥8.0 |
| Shear strength kg/cm2 Fe-Fe | ≥3.0 |
| Density of | 1.28±0.05 |
| Flame-retardant UL-94 | V-0 |
| Toughness (20 ℃, 5 ℃, 9 sample pieces) | Are not bent and broken |
The invention adopts two-step bulk polymerization, has no pollution in production, avoids solvent recovery and product purification, and has simple process. The raw materials adopt domestic 010 resin or 011 resin, which has low cost and rich sources. The softening point and viscosity can be adjusted by changing the process conditions. The dihydric alcohol or the polyhydric alcohol replaces diamine in the formula, so that the probability of forming hydrogen bonds in macromolecules can be reduced, and the flexibility of the product is improved.
Detailed Description
Example 1:
mixing low molecular polyamide with 010 resin with softening point of 90-130 deg.C and C6The dibasic acid of (1): mixing at a ratio of 0.6, adding into a reaction kettle with a vacuum and condensation system, heating to 250 ℃ under stirring, reacting for one hour, and vacuumizing for one hour, wherein the vacuum degree is more than or equal to 0.08 MPa. After the evacuation is stopped, the temperature is reduced to 160 ℃, ethylene glycol 0.8 time of 010 resin is added, and the temperature is gradually increased to 250 ℃ for reaction for 4 hours. The obtained product isCooling the brown viscous liquid to obtain a tough solid with a softening point of150 ℃ and a viscosity (190 ℃) of 1600 mPa.S;
the method for preparing the low-molecular-weight polyamide modified hot melt adhesive is characterized in that low-molecular-weight polyamide is modified through two steps of crosslinking and grafting, wherein the crosslinking agent is dihydric alcohol or polyhydric alcohol, and the molecular weight of the crosslinking agent is 60-2000; wherein either a single alcohol or a mixture of alcohols may be used; the grafting agent is aliphatic saturated dibasic acid or unsaturated dibasic acid, and the number of carbon atoms is 6-13; the low molecular polyamide suitable for the invention is domestic 010 resin or 011 resin. The raw material ratio is as follows: the synthesis conditions of the low molecular polyamide, the grafting agent and the crosslinking agent are 1: 0.6: 0.8 (mol): the vacuum degree is 0.05-0.1 MPa; the temperature is 150-300 ℃; the reaction time is 1-11 h.
Example 2:
010 resin was mixed with C under the operating conditions of example 16The dibasic acid of (1: 1.8) is mixed, wherein the ratio of the low molecular polyamide to the grafting agent to the crosslinking agent is 1: 1.8: 0.8 (mol);
example 3:
under the operating conditions of example 1, C is added6C for dibasic acid of13Dibasic acid, wherein the ratio of low molecular weight polyamide to grafting agent to crosslinking agent is 1: 0.6: 0.8 (mol);
example 4:
under the operating conditions of example 1, the ethylene glycol was replaced by butanediol, the low molecular polyamide, grafting agent and crosslinking agent amounting to 1: 0.6: 0.8 (mol);
example 5:
under the operating conditions of example 1, the ethylene glycol was replaced bypolyethylene glycol 2000, where the low molecular polyamide: grafting agent: crosslinking agent is 1: 0.6: 0.8 (mol);
example 6:
010 resin is mixed with ethylene glycol in a ratio of 1: 1.6 under the operating conditions of example 1, where low molecular polyamide: grafting agent: crosslinking agent is 1: 0.6: 1.6 (mol);
example 7:
under the operating conditions of example 1, ethylene glycol and propylene glycol were admixed in a mixing ratio of 1.5: 1, where low-molecular polyamide, grafting agent and crosslinking agent are 1: 0.6: 0.8 (mol);
example 8:
under the operating conditions of example 1, 30% Al (OH) are added3(ii) a Then the adjustment can be made according to different needs, such as: the method is used in the aspect of televisions.
The properties of the product obtained in the above examples are given in the following table:
| practice of Example (b) | Softening point ℃ | Viscosity (190 ℃ C.) mPa.S | Flame retardancy (UL-94) | Low temperature toughness (5 ℃, folded 200 times) | Shear strength MPa |
| 1 | 150 | 1600 | Class V-0 | Not bent and broken | 6.8 |
| 2 | 148 | 1800 | Class V-0 | Not bent and broken | 7.0 |
| 3 | 153 | 2000 | Class V-0 | Not bent and broken | 7.5 |
| 4 | 160 | 3000 | Class V-0 | Not bent and broken | 7.2 |
| 5 | 130 | 6000 | Class V-0 | Not bent and broken | 7.5 |
| 6 | 145 | 1500 | Class V-0 | Not bent and broken | 6.5 |
| 7 | 150 | 2300 | Class V-0 | Not bent and broken | 8.2 |
| 8 | 155 | 3100 | Class V-0 | Not bent and broken | 9.4 |
Claims (3)
1. The low-molecular polyamide modified hot melt adhesive is characterized by having the following repeating unit structure:
wherein: r1As dimer acid, R2Is- (CH)2)-2-12，R3Is- (CH)2)-6-13，R4Is- (CH)having a molecular weight of 60-20002) -or- (C)2H4O)nCH2-。
2. The preparation method of the low molecular polyamide modified hot melt adhesive as claimed in claim 1, wherein the low molecular polyamide is modified by two steps of grafting and crosslinking, and the preparation method comprises the following specific steps: firstly, adding low-molecular polyamide and a grafting agent into a reaction kettle with a vacuum and condensation system in proportion, heating while stirring for a grafting reaction to obtain a prepolymer, vacuumizing, cooling, adding a crosslinking agent in proportion, heating for a plurality of hours for a crosslinking reaction to obtain a low-molecular polyamide modified hot melt adhesive; wherein the low molecular polyamide suitable for the invention is domestic 010 resin or 011 resin; the grafting agent is aliphatic saturated dibasic acid or unsaturated dibasic acid, and the number of carbon atoms is 6-13; the cross-linking agent is single alcohol or mixed alcohol, and the molecular weight of the cross-linking agent is 60-2000; the raw material ratio is as follows: low molecular polyamide, grafting agent and cross-linking agent are 1: 0.4-2.2: 0.2-2.0 (mol); the synthesis conditions are as follows: the vacuum degree is 0.05-0.1 MPa; the reaction temperature is 150-300 ℃; the reaction time is 1-11 h.
3. The method for preparing low molecular polyamide modified hot melt adhesive according to claim 2, wherein the cross-linking agent is diol or polyol or polymeric diol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410066137 CN1264894C (en) | 2004-12-09 | 2004-12-09 | Low molecular polyamide modified hot melt adhesive and method for preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410066137 CN1264894C (en) | 2004-12-09 | 2004-12-09 | Low molecular polyamide modified hot melt adhesive and method for preparation |
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| Publication Number | Publication Date |
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| CN1635014A true CN1635014A (en) | 2005-07-06 |
| CN1264894C CN1264894C (en) | 2006-07-19 |
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|---|---|---|---|
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| Country | Link |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012777A (en) * | 2011-09-20 | 2013-04-03 | 上海杰事杰新材料(集团)股份有限公司 | High temperature resistant semi-aromatic polyamide, preparation method and applications thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040000290A (en) | 2002-06-24 | 2004-01-03 | 엘지전자 주식회사 | Method for managing multi-path data stream of high density optical disc |
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2004
- 2004-12-09 CN CN 200410066137 patent/CN1264894C/en active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012777A (en) * | 2011-09-20 | 2013-04-03 | 上海杰事杰新材料(集团)股份有限公司 | High temperature resistant semi-aromatic polyamide, preparation method and applications thereof |
| CN103012777B (en) * | 2011-09-20 | 2016-01-06 | 上海杰事杰新材料(集团)股份有限公司 | A kind of High-temperature-ressemi-aromatic semi-aromatic polyamide, preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| CN1264894C (en) | 2006-07-19 |
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Assignee: Changzhou Baoli Adhesive Co., Ltd. Assignor: Jiangsu Polytechnic University Contract fulfillment period: 2007.11.30 to 2013.11.30 contract change Contract record no.: 2009320000180 Denomination of invention: Low molecular polyamide modified hot melt adhesive and method for preparation Granted publication date: 20060719 License type: Exclusive license Record date: 2009.3.2 |
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Effective date of registration: 20141205 Address after: Daitou town of Liyang City Ferry Street 213311 Jiangsu city of Changzhou province 8-2 No. 7 Patentee after: Liyang Chang Technology Transfer Center Co., Ltd. Address before: 213016 Baiyun Road, Jiangsu, Changzhou Patentee before: Jiangsu Polytechnic University |