CN103184030A - Novel polyamide adhesive - Google Patents
Novel polyamide adhesive Download PDFInfo
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- CN103184030A CN103184030A CN2011104493945A CN201110449394A CN103184030A CN 103184030 A CN103184030 A CN 103184030A CN 2011104493945 A CN2011104493945 A CN 2011104493945A CN 201110449394 A CN201110449394 A CN 201110449394A CN 103184030 A CN103184030 A CN 103184030A
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Abstract
The invention relates to a polyamide hot melt adhesive and a preparation method thereof. The polyamide hot melt adhesive comprises: (1) a C5-C18 aliphatic dicarboxylic acid copolymerization unit; and (2) a diamine copolymerization unit, which is composed of, based on its total mole number: (a) 20-70 mole% of a C24-C48 dipolyamine copolymerization unit; (b) 0-30 mole% of a C2-C10 aliphatic diamine copolymerization unit; (c) 0-50 mole% of a C4-C8 heterocyclic diamine copolymerization unit; and (d) 5-50 mole% of a poly C1-4 alkylidene ether diamine copolymerization unit. The number average molecular weight Mn of the polyamide hot melt adhesive ranges from 2000 to 30000. The polyamide hot melt adhesive has a moderate softening point, extremely low water absorption and low temperature impact resistance, thus being suitable to serve as a hot melt adhesive.
Description
Technical field
The present invention relates to a kind of tackiness agent, particularly a kind of polymeric amide tackiness agent.
Background technology
Polymeric amide is a family macromolecule fluidized polymer that contains amide group on the molecular backbone chain, and they both can be made into various plastics, but wire drawing becomes fiber again, can also make film, coating, tackiness agent etc.
Polymeric amide as tackiness agent mainly contains two classes, and what molecular weight was higher is copolyamide, and this class polyamide hot has excellent water-fastness and dry cleaning resistance energy, is widely used in the bonding of fiber, and is very big at the textile industry consumption.Another kind of polymeric amide is to be formed by dimeracid and diamine polycondensation, has advantages such as melting range is narrow, quick solidifying, adhesiveproperties excellence, is widely used in fields such as shoemaking, automobile, electronics, material contracting with heat at present.
Had much for the polymeric amide Study on making adhesives both at home and abroad, especially to the improvement of dimer acid type polyamide, by adopting blend or copolymerization mode, shortcomings such as its fragility, the easy moisture absorption have been improved.In the US4670552 patent, with polymeric amide and polyesteramide blend, obtained a kind of flexible hot melt adhesive of high and low temperature that has, materials such as polyethylene, polyester, polymeric amide and PVC have been had good bonding; US5989385 obtains a kind of hot melt adhesive with blend such as dimeric acid type polyamide hot melt adhesive and Gum Rosin, terpine resin, EVA, is applied in the bookbinding aspect, can carry out bookbinding under relatively low temperature.In recent years, the domestic attention that has also caused the insider for the research of dimer acid type polyamide.CN101372610 compares traditional dimer acid type polyamide by introducing oligopolymer modifications such as polyethylene oxide diamine or propylene oxide diamines, and its toughness is greatly improved, below low temperature resistant the reaching-40 ℃; CN101633829 has improved the stopping property of polymeric amide tackiness agent by introducing active paracril, makes it to have obtained in heat-shrinkable T bush to use widely.
Dimeric acid type polyamide hot melt adhesive is owing to excellent performance, and Application Areas especially at the polyamide hot of sector applications such as Electronic Packaging field and cable, requires harsh especially to water-intake rate and heat resistance in continuous expansion.But because domestic dimeric acid type polyamide hot melt adhesive still has higher water-intake rate and fragility, and fail extensively to be promoted in these high-end applications fields.
Therefore, press in this area and obtain a kind of novel polymeric amide, have extremely low water-intake rate and excellent resistance to low temperature, especially low-temperature impact-resistant performance, compare existing dimer acid type polyamide and be significantly improved.The present invention is directed to the deficiencies in the prior art, by growing copolymerization such as carbochain di-carboxylic acid and two polyamine, aliphatic diamine, heterocyclic amine and polytetramethylene ether diamine, polyamide hot of the present invention adopts one-step polymerization method, and product performance are stable, are convenient to industrialization production.
Summary of the invention
The object of the invention is to provide a kind of polyamide hot.This polyamide hot has moderate softening temperature, extremely low water-intake rate and low-temperature impact-resistant performance.Can be used as hot melt adhesive, polarity and non-polar material are had good bonding force; Also can be used as sealing material, electronic product is reached the effect of seal protection.
Polyamide hot of the present invention comprises following copolymerization units:
(1) C5～C18 aliphatic dicarboxylic acid copolymerization units; With
(2) diamine copolymerization units is made of following component:
(a) 20～70 moles of %C24～C48 dimerization amine copolymer unit;
(b) 0～30 mole of %C2～C10 aliphatic series diamine copolymerization units;
(c) 0～50 mole of %C4-C8 heterocycle diamine copolymerization units; With
(d) 5～50 moles of poly-C of %
1-4Alkylene ether diamines unit, above-mentioned molecular fraction is benchmark with the total mole number of diamine copolymerization units; The number-average molecular weight Mn scope of described polyamide hot is 2000～30000.
Polyamide hot of the present invention has extremely low water-intake rate and excellent resistance to low temperature, especially low-temperature impact-resistant performance, compares existing dimer acid type polyamide and is significantly improved.
Embodiment
One preferred embodiment in, polyamide hot of the present invention comprises following copolymerization units:
(1) C8～C16 aliphatic dicarboxylic acid copolymerization units; With
(2) diamine copolymerization units is made of following component:
(a) 25～65 moles of %C28～C40 dimerization amine copolymer unit;
(b) 5～25 moles of %C4～C8 aliphatic series diamine copolymerization units;
(c) 10～45 moles of %C4-C6 heterocycle diamine copolymerization units; With
(d) 10～45 moles of poly-C of %
2-4Alkylene ether diamines unit, above-mentioned molecular fraction is benchmark with the total mole number of diamine copolymerization units; The number-average molecular weight Mn scope of described polyamide hot is preferably 5000～20000, is more preferably 5000～15000.
In polyamide hot of the present invention, the mol ratio of aliphatic dicarboxylic acid copolymerization units and diamine copolymerization units is (0.95～1.1) generally close to stoichiometry: 1, be preferably (0.98～1.05): and 1, more preferably 1: 1.
Aliphatic dicarboxylic acid copolymerization units among the present invention is derived from C5～C18 aliphatic dicarboxylic acid, be preferably the long-chain fat family di-carboxylic acid of C10～C16, for example comprise suberic acid, sebacic acid, dodecanedioic acid, undecane dicarboxylic acid, tetradecane diprotic acid, Thapsic acid, octadecane diacid or its mixture, preferably include sebacic acid, dodecanedioic acid, tetradecane diprotic acid or its mixture.
One preferred embodiment in, in polyamide hot of the present invention, also can contain a spot of aromatic binary carboxylic acid copolymerization units, 20 moles of % that its content is no more than aliphatic dicarboxylic acid copolymerization units total mole number are advisable, and 10 moles of % that preferably are no more than aliphatic dicarboxylic acid copolymerization units total mole number are advisable.Above-mentioned aromatic binary carboxylic acid copolymerization units is derived from the C6-10 aromatic binary carboxylic acid, for example terephthalic acid, m-phthalic acid or its mixture.
One preferred embodiment in, the C24 described in the present invention～C48 dimerization amine copolymer unit is derived from C24～C48 two polyamine, and two polyamine are obtained by dimeracid nitrilation, hydrogenation.Existing corresponding product-feed on the market, amine value 200～210mgKOH/g.
One preferred embodiment in, C2 described in the present invention～C10 aliphatic series diamine copolymerization units is derived from C2～C10 aliphatic series diamine, for example comprise quadrol, propylene diamine, butanediamine, pentamethylene diamine, hexanediamine, octamethylenediamine, decamethylene diamine or its mixture more than two kinds, preferably include butanediamine, pentamethylene diamine, hexanediamine or its mixture more than two kinds.
One preferred embodiment in, C5-C8 heterocycle diamine copolymerization units described in the present invention is derived from C5-C8 heterocycle diamine, for example comprise piperazine, aminoethyl piperazine, cyclohexanediamine, pyridine diamines, different Fu Er ketone diamines or more than one mixtures wherein, preference is as comprising piperazine, cyclohexanediamine, different Fu Er ketone diamines or more than one mixtures wherein.
One preferred embodiment in, poly-C described in the present invention
1-4Autohemagglutination C derives in alkylene ether diamines unit
1-4The alkylene ether diamines, for example comprise polyoxymethylene diamines, polyethylene oxide diamines, Polypropylene oxide diamine, polytetramethylene ether diamine or their mixture, preferably include polyethylene oxide diamines, Polypropylene oxide diamine, polytetramethylene ether diamine or their mixture, polytetramethylene ether diamine most preferably, be that molecular backbone chain is based on the diamine of polytetramethylene ether diol, molecular structure is as follows
Wherein n represents the chain hop count of tetramethylene polymerized unit, and scope is 5～30, and preferred n value is 13～23.
Above-mentioned polytetramethylene ether diamine molecular weight is 500～3000, preferred molecular weight range 1000～2000, and Huntsman company has corresponding product-feed, and the trade mark is THF-100, THF-140 and THF-170, preferred THF-100.
Polymeric amide tackiness agent among the present invention is obtained by multiple monomer copolymerizations such as above-mentioned di-carboxylic acid and two polyamine, aliphatic diamine, heterocyclic amine and polytetramethylene ether diamines.Because the introducing of two polyamine descends the water-absorbent of polymeric amide greatly; Simultaneously, introduce the polytetramethylene ether diamines, even the polyamide product force of cohesion height, the resistance to low temperature excellence that obtain at low temperatures, also have excellent shock resistance.
The contriver is further finding that also compare existing dimeric acid type polyamide hot melt adhesive, this polyamide product is good to the wetting property of non-polar material, so it is to also very high such as nonpolar difficult cohesive material bonding strengths such as PP, PE in the application test.
The method that obtains high molecular polymeric amide tackiness agent of the present invention is: the ratio of total acid and total amine fed intake near 1: 1 as far as possible; The method that obtains lower molecular weight polymeric amide tackiness agent of the present invention is: a kind of excessive relatively with in above-mentioned acid or the amine, perhaps adopt the molecular weight end-capping reagent.Molecular weight end-capping reagent commonly used has unit acid or unit amine.Unit acid is Glacial acetic acid for example, propionic acid, butyric acid, stearic acid, oleic acid etc.Unit amine comprises propylamine, butylamine etc.
Select acid catalysis for use in the synthesis technique of polymeric amide tackiness agent of the present invention, for example phosphoric acid, phosphorous acid or this mixing acid of two kinds; Catalyst levels is 0.01～0.05wt% of monomer total mass, is preferably 0.015～0.025wt%.
Can add oxidation inhibitor, anti ultraviolet agent, nucleator, impact modifier, lubricant etc. on a small quantity in the synthesis technique of polymeric amide tackiness agent of the present invention.Unit carboxylic acid or unit amine, as molecular weight regulator, content is 0～3 mole of % of total amine or total acid;
Above-mentioned oxidation inhibitor for example comprises antioxidant 1010,168,1076,1098, antioxidant 264, triphenyl phosphite etc., and its content is 0～2wt% of monomer total mass, is preferably 0.2～1wt%.。
Other auxiliary agents, as thermo-stabilizer commonly used in this area, anti ultraviolet agent, nucleator, impact modifier, lubricants etc. also can be used in the system of the present invention.Its consumption is as the criterion with the performance that does not influence polymeric amide tackiness agent of the present invention.
Polyamide product of the present invention, can be synthetic by following technology: after comonomer such as di-carboxylic acid (as the C14 diprotic acid), two polyamine, piperazine, polytetramethylene ether diamine, phosphoric acid and antioxidant 1010 and the accurate weighing of auxiliary agent, drop in 1 liter the four-hole boiling flask.Under nitrogen and agitation condition, be warming up to 160 ℃, the component in bottle is dissolved fully; Slowly heat up then, in 1.5～2 hours, temperature in the kettle is raised to 240 ℃ by 160 ℃, measure the water yield simultaneously; When aquifer yield reaches 80% when above of theoretical value, progressively reduce pressure; Finally under high vacuum, finish entire reaction, about 2～10 hours of vacuum reaction time.Use the nitrogen pressurising then under normal pressure, while hot polymeric amide is fallen on tetrafluoro plate face, be cut into particle behind the cooling forming.
Polymeric amide of the present invention has extremely low water-intake rate and excellent low-temperature impact-resistant performance, can be used as hot melt adhesive, is convenient to apply, and all kinds of polarity and non-polar material is all had good bonding; Also can be used as packaged material, electronic devices and components are carried out packaging protection, favorable shock resistance can guarantee the anti-ability of beating of encapsulating products, and extremely low water-intake rate also can prolong the work-ing life of encapsulating products simultaneously.
Embodiment
Describe the present invention in detail with embodiment below, but these embodiment only are used for the purpose of description and interpretation, and can not be used for limiting the scope of the invention.Scope of the present invention is determined by appending claims.
In following embodiment, polymeric amide of the present invention is test performance in accordance with the following methods:
Softening temperature test: test by standard GB/T 15332-94.
Melt viscosity test: adopt Brookfield DV-E type rotational viscosimeter specimen at 232 ℃ melt viscosity.
The water-intake rate test: with reference to GB/T 1034-1998 test, 23 ℃ of room temperatures are soaked 24h.Size of sample: diameter (50 ± 1) mm, the disk of thickness (3 ± 0.2) mm.
Hardness test: with reference to GB/T 531.1 and GB/T 531.2 tests.
Shock strength: with reference to ASTMD 950-2003 (2011) test, the shock strength of-18 ℃ and 25 ℃.
Embodiment 1
With 0.5 mole of sebacic acid, 0.25 mole two polyamine (Britain standing grain major company, Priamine1074), 0.05 mole hexanediamine, 0.125 mole of piperazine, 0.075 mole of polytetramethylene ether diamine (THF-100) and 0.3g antioxidant 1010 etc. drop in the 1000ml four-hole boiling flask, are warming up to 160 ℃ under nitrogen protection; After treating that a bottle interior component is dissolved fully, beginning slowly heats up.In 1.5～2h, be warming up to 240 ℃; Measure the water yield; Wait to reach 80% when above of theoretical aquifer yield, progressively reduce pressure; Finally under high vacuum, finish entire reaction, about 5～10 hours of vacuum reaction time.Use the nitrogen pressurising then under normal pressure, stir half an hour.While hot polymeric amide is fallen on tetrafluoro plate face at last, be cut into particle behind the cooling forming.
The polyamide hot that obtains, after tested, ring and ball softening point is 168 ℃; Melt viscosity is 4000cp in the time of 232 ℃.
Embodiment 2～6
Embodiment 2～6 obtains polyamide product with reference to the prescription in the table 1 and above-mentioned synthesis technique.
Comparative Examples
With 0.87 mole dimeracid (Britain standing grain major company, P1017) and 0.05 mole of sebacic acid, 0.08 mole of stearic acid and 0.3g antioxidant 1010 drop in the 1L four-hole boiling flask, in the constant pressure funnel of packing into after 0.9 moles of ethylene diamine and the 0.1 mole of accurate weighing of hexanediamine; Logical nitrogen is heated to 130 ℃ with the dimeracid in the still etc., drips hybrid diamine gradually, generally in 30min, drip off, during dropping in the reaction flask temperature preferably remaining on below 140 ℃ always; After dripping, slowly promote temperature of reaction by 20 ℃/h heat-up rate, until being increased to 230-240 ℃, keep this temperature section 1h at least, and measure the water that distillates, reach 80% o'clock of theoretical amount, can progressively reduce pressure; Finally under high vacuum, finish entire reaction, about 2 ~ 10 hours of vacuum reaction time.Use the nitrogen pressurising then under normal pressure, add various additives, stir half an hour.While hot polymeric amide is fallen on tetrafluoro plate face at last, be cut into particle behind the cooling forming.
The polymeric amide that obtains is yellow particles, and after tested, ring and ball softening point is 123 ℃, and 232 ℃ of melt viscosities are 1200cp.
Each Example formulations listed by table 1 and performance compares.
Table 1 embodiment and commercially available dimeric acid type polyamide hot melt adhesive performance are relatively
Claims (10)
1. polyamide hot, it comprises following copolymerization units:
(1) C5～C18 aliphatic dicarboxylic acid copolymerization units; With
(2) diamine copolymerization units is made of following component:
(a) 20～70 moles of %C24～C48 dimerization amine copolymer unit;
(b) 0～30 mole of %C2～C10 aliphatic series diamine copolymerization units;
(c) 0～50 mole of %C4-C8 heterocycle diamine copolymerization units; With
(d) 5～50 moles of poly-C of %
1-4Alkylene ether diamines unit, above-mentioned molecular fraction is benchmark with the total mole number of diamine copolymerization units; The number-average molecular weight Mn scope of described polyamide hot is 2000～30000.
2. polyamide hot as claimed in claim 1 is characterized in that, it comprises following copolymerization units:
(1) C8～C16 aliphatic dicarboxylic acid copolymerization units; With
(2) diamine copolymerization units is made of following component:
(a) 25～65 moles of %C28～C40 dimerization amine copolymer unit;
(b) 5～25 moles of %C4～C8 aliphatic series diamine copolymerization units;
(c) 10～45 moles of %C4-C6 heterocycle diamine copolymerization units; With
(d) 10～45 moles of poly-C of %
2-4Alkylene ether diamines unit, above-mentioned molecular fraction is benchmark with the total mole number of diamine copolymerization units; The number-average molecular weight Mn scope of described polyamide hot is preferably 5000～20000.
3. polyamide hot as claimed in claim 1 or 2 is characterized in that, the mol ratio of described aliphatic dicarboxylic acid copolymerization units and diamine copolymerization units is (0.95～1.1): 1.
4. polyamide hot as claimed in claim 1 or 2 is characterized in that, it also contains the aromatic binary carboxylic acid copolymerization units, and its content is no more than 20 moles of % of aliphatic dicarboxylic acid copolymerization units total mole number.
5. polyamide hot as claimed in claim 1 or 2 is characterized in that, forms the amine value 200～210mgKOH/g of two polyamine of described dimerization amine copolymer unit.
6. polyamide hot as claimed in claim 1 or 2 is characterized in that, described heterocycle diamine copolymerization units is derived from piperazine, aminoethyl piperazine, cyclohexanediamine, pyridine diamines, different Fu Er ketone diamines or more than one mixtures wherein.
7. polyamide hot as claimed in claim 1 is characterized in that, described poly-C
1-4Alkylene ether diamines unit is derived from polyoxymethylene diamines, polyethylene oxide diamines, Polypropylene oxide diamine, polytetramethylene ether diamine or their mixture.
8. polyamide hot as claimed in claim 7 is characterized in that, described polytetramethylene ether diamine be molecular backbone chain based on the diamine of polytetramethylene ether diol, molecular structure is as follows,
Wherein n represents the chain hop count of tetramethylene polymerized unit, and scope is 5～30, and preferred n value is 13～23.
9. polyamide hot as claimed in claim 1 is characterized in that, described C2～C10 aliphatic series diamine copolymerization units is derived from butanediamine, pentamethylene diamine, hexanediamine or its mixture more than two kinds.
10. polyamide hot as claimed in claim 1 is characterized in that, described C5～C18 aliphatic dicarboxylic acid copolymerization units is derived from sebacic acid, dodecanedioic acid, tetradecane diprotic acid or its mixture.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103524731A (en) * | 2013-10-16 | 2014-01-22 | 上海天洋热熔胶有限公司 | Preparation method of polyamide hot melt adhesive with low surface energy for hot drills |
| CN104673177A (en) * | 2013-11-29 | 2015-06-03 | 上海轻工业研究所有限公司 | Thermoplastic polyamide hot-melt adhesive composition |
| CN105778844A (en) * | 2014-12-19 | 2016-07-20 | 上海理日化工新材料有限公司 | Polyurea adhesive and preparation method thereof |
| CN106062113A (en) * | 2014-09-02 | 2016-10-26 | 积水化学工业株式会社 | Double-sided adhesive tape for portable electronic device |
| CN108148198A (en) * | 2017-12-22 | 2018-06-12 | 山东凯恩新材料科技有限公司 | One kind can low-pressure injection molding polyamide hot and preparation method thereof |
| CN109749695A (en) * | 2017-11-06 | 2019-05-14 | 山东凯恩新材料科技有限公司 | A kind of novel polyamide hot melt adhesive and preparation method thereof |
| CN113426310A (en) * | 2021-06-25 | 2021-09-24 | 衢州清澜新材料有限公司 | Non-woven fabric base material for high-stiffness tubular membrane and preparation method thereof |
| CN114656917A (en) * | 2020-12-23 | 2022-06-24 | 上海天洋热熔粘接材料股份有限公司 | Phenol yellowing resistant copolyamide hot melt adhesive and preparation method thereof |
| CN116410591A (en) * | 2023-04-14 | 2023-07-11 | 四川大学 | piperazine-Biuret copolyamide film with high dielectric constant and low dielectric loss and preparation method thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103524731A (en) * | 2013-10-16 | 2014-01-22 | 上海天洋热熔胶有限公司 | Preparation method of polyamide hot melt adhesive with low surface energy for hot drills |
| CN104673177A (en) * | 2013-11-29 | 2015-06-03 | 上海轻工业研究所有限公司 | Thermoplastic polyamide hot-melt adhesive composition |
| CN104673177B (en) * | 2013-11-29 | 2017-11-14 | 上海轻工业研究所有限公司 | Polyamide thermoplastic hot-melt adhesive composition |
| CN106062113A (en) * | 2014-09-02 | 2016-10-26 | 积水化学工业株式会社 | Double-sided adhesive tape for portable electronic device |
| CN105778844A (en) * | 2014-12-19 | 2016-07-20 | 上海理日化工新材料有限公司 | Polyurea adhesive and preparation method thereof |
| CN109749695A (en) * | 2017-11-06 | 2019-05-14 | 山东凯恩新材料科技有限公司 | A kind of novel polyamide hot melt adhesive and preparation method thereof |
| CN108148198A (en) * | 2017-12-22 | 2018-06-12 | 山东凯恩新材料科技有限公司 | One kind can low-pressure injection molding polyamide hot and preparation method thereof |
| CN114656917A (en) * | 2020-12-23 | 2022-06-24 | 上海天洋热熔粘接材料股份有限公司 | Phenol yellowing resistant copolyamide hot melt adhesive and preparation method thereof |
| CN113426310A (en) * | 2021-06-25 | 2021-09-24 | 衢州清澜新材料有限公司 | Non-woven fabric base material for high-stiffness tubular membrane and preparation method thereof |
| CN113426310B (en) * | 2021-06-25 | 2022-04-19 | 安徽清澜新材料科技有限公司 | Non-woven fabric base material for high-stiffness tubular membrane and preparation method thereof |
| CN116410591A (en) * | 2023-04-14 | 2023-07-11 | 四川大学 | piperazine-Biuret copolyamide film with high dielectric constant and low dielectric loss and preparation method thereof |
| CN116410591B (en) * | 2023-04-14 | 2024-04-05 | 四川大学 | piperazine-Biuret copolyamide film with high dielectric constant and low dielectric loss and preparation method thereof |
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