CN108384022A - A kind of preparation improving uncured rubber asphalt high temperature resistance hyperbranched resin - Google Patents

A kind of preparation improving uncured rubber asphalt high temperature resistance hyperbranched resin Download PDF

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CN108384022A
CN108384022A CN201810222771.3A CN201810222771A CN108384022A CN 108384022 A CN108384022 A CN 108384022A CN 201810222771 A CN201810222771 A CN 201810222771A CN 108384022 A CN108384022 A CN 108384022A
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generation
preparation
uncured rubber
rubber asphalt
resin
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CN108384022B (en
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寿崇琦
张耀文
王德卫
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Inner Mongolia ante Weidun Waterproof Technology Co.,Ltd.
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University of Jinan
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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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules
    • 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules
    • C08G83/006—After treatment of hyperbranched macromolecules
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D195/00—Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/18—Fireproof paints including high temperature resistant paints
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

The present invention relates to uncured rubber asphalt waterproof coating field, more specifically to a kind of preparation for the hyperbranched resin improving uncured rubber asphalt waterproof coating high temperature resistance.A kind of isocyanate terminated dissaving polymer has been synthesized first, then by the way that amino is introduced into the hyperbranched resin end with amino-modified silicone, to synthesize a kind of amine-terminated hyperbrancedization resin.The amine-terminated hyperbrancedization resin is applied into uncured rubber asphalt waterproof coating field, uncured rubber asphalt waterproof coating high temperature resistance can be improved well, synthesis technology is easy, easily industrializes, is a kind of uncured rubber asphalt waterproof coating modifying agent of function admirable.

Description

A kind of preparation improving uncured rubber asphalt high temperature resistance hyperbranched resin
Technical field
The present invention relates to uncured rubber asphalt waterproof coating technical fields, more particularly to a kind of for improving uncured rubber Glue asphalt waterproofing paint high temperature resistance hyperbranched resin, further relates to preparation method.
Background technology
Uncured rubber asphalt waterproof coating is a kind of polymer modified asphalt water-repellent paint of high solids content.With long-term Do not cure, self-healing ability is strong, it is difficult to remove, the features such as low temperature bonding performance is good.It can solve to prevent caused by base's stress variation The problems such as water layer is broken.At the same time as bottom attachment coating with waterproof roll with the use of composition complex waterproof layer, this waterproof Layer can solve that the insoluble string water problems of waterproof roll institute is used alone.
The main component of traditional uncured rubber asphalt waterproof coating is by pitch, rubber, softening agent, tackifier, steady Determine agent, filler etc. to be made.For the ease of construction, traditional uncured rubber asphalt waterproof coating can generally be designed to have under high temperature The problems such as larger trickling property, this is easy for leading to product poor heat resistance, and high temperature is easily slided, trickled.
Patent of the present invention is intended to introduce the hyperbranched resin containing a large amount of Amino End Group siloxanes so that uncured rubber asphalt Water-repellent paint is chemically crosslinked with hyperbranched resin, improves its high temperature resistance.
Dissaving polymer has 3 D stereo reticular structure, and active site is more, and viscosity is small, good with matrix amalgamation, tool Have broad application prospects, is all shown in fields such as photoelectric material, coating, adhesive, nanosecond science and technology, drug carriers at present Huge application value.
Invention content
In order to solve uncured rubber asphalt waterproof coating poor heat resistance, the problems such as high temperature is easily slided, trickled, the present invention carries A kind of amine-terminated hyperbrancedization resin for improving uncured rubber asphalt waterproof coating heat resistance is supplied.
The present invention also provides the preparation methods of the amine-terminated hyperbrancedization resin.
The present invention is achieved by the following measures：
A kind of application of amine-terminated hyperbrancedization resin in improving uncured rubber asphalt waterproof coating heat resistance, the end Amino hyperbranched resin is obtained through the following steps：
2,2-dihydromethyl propionic acids of 3 ~ 4.5 times of polyalcohol and polyalcohol molal quantity are added under nitrogen protection after mixing Heat is to 140 ~ 170 DEG C, 1.5 ~ 2h of synthesis under normal pressure；Then be added isocyanates and triethanolamine be heated to 60 under nitrogen protection ~ 70 DEG C, react 4h；Then it adds Amino End Group silicone oil and 3h is stirred at room temperature.
The polyalcohol is trihydroxylic alcohol or tetrahydroxylic alcohol.
The trihydroxylic alcohol is one or more of trimethylolpropane, glycerine, butantriol, triethanolamine.
The tetrahydroxylic alcohol is pentaerythrite.
The isocyanates is 2,4-toluene-2,4-diisocyanates, 4,4-methyl diphenylene diisocyanates, different Fo Er One or more of ketone diisocyanate.
The isocyanate terminated hyperbranched resin of the difference algebraically, the wherein first generation, the second generation, the third generation, forth generation are polynary Alcohol is 1 with isocyanates molar ratio:6~8、1:18~24、1:42~56、1:90~120.
The isocyanate terminated hyperbranched resin of the difference algebraically, the wherein first generation, the second generation, the third generation, forth generation are polynary Alcohol is 1 with triethanolamine molar ratio:0、1:6~8、1:18~24、1:42~56.
The isocyanate terminated hyperbranched resin of the difference algebraically, the wherein first generation, the second generation, the third generation, forth generation are polynary Alcohol is 1 with isocyanate terminated molar ratio:6~8、1:12~16、1:24~32、1:48~64.
The isocyanate terminated hyperbranched resin of the difference algebraically may but be not limited only to such as following formula institute by taking the second generation as an example Show：
The weight average molecular weight of the Amino End Group silicone oil is 300 ~ 1000, and the amino containing 0.1 ~ 2w%.
The Amino End Group silicone oil is 1 with isocyanate terminated molar ratio:1.
The Amino End Group silicone oil is one kind in DOW CORNING CM-226, DOW CORNING OFX-8040A, DOW CORNING OFX-8803 Or it is two or more.
Compared with the existing technology, what prepared by method of the present invention is used to improve uncured rubber asphalt high temperature resistance Amine-terminated hyperbrancedization resin, has the following advantages：
First by polyalcohol and 2,2-dihydromethyl propionic acid reactions prepare terminal hydroxy group centronucleus, then introduce isocyanates and hydroxyl Base reacts, while introducing triethanolamine and increasing branch, forms the dissaving polymer of polyisocyanates, is the access of amido silicon oil Provide a large amount of active group.
The introducing of siloxanes simultaneously is also beneficial to improve the heat resistance and compliance of resin；In amine-terminated hyperbrancedization resin A large amount of amino can be crosslinked with groups such as ester groups in pitch, formed reticular structure and improved uncured rubber asphalt waterproof coating High temperature resistance.
Beneficial effects of the present invention：
Resin prepared by the present invention uses dissaving structure, and preparation method is simple, and raw material is easy to get, and a large amount of activity is contained in end Functional group can reduce inventory, reduce cost；There is larger carry to the high temperature resistance of uncured rubber asphalt waterproof coating simultaneously Height, it is uniform with uncured rubber asphalt waterproof coating blending and stirring, do not increase additional technological process, be conducive to control at This.
Specific implementation mode
More to be stated in detail to specific implementation method of the present invention below, it is therefore intended that illustrate the present invention design and Feature, it is not intended to limit the scope of the present invention.Any equivalent change or modification in accordance with the spirit of the invention, It should be covered by the protection scope of the present invention.
Implementation one
（1）Weigh 13.60g（0.1mol）Pentaerythrite, 53.65g（0.4mol）2,2-dihydromethyl propionic acids, first by season penta Tetrol and 2,2-dihydromethyl propionic acids are added in the four-hole boiling flask with magnetic stirring apparatus, add appropriate N, N-dimethyl methyl Amide makes it dissolve, and adds 0.80g p-methyl benzenesulfonic acids, is warming up to 140 DEG C, synthesis under normal pressure 1.5h；65 DEG C are cooled to, then 139.20g is added（0.8mol）2,4-toluene-2,4-diisocyanates react under dibutyltindilaurate catalyzed and nitrogen protection 4h；Near room temperature, is slowly added to 240.00g amido silicon oils, reaction 3h both amine-terminated hyperbrancedization resin.
（2）A certain amount of uncured rubber asphalt waterproof coating is taken to be added in crucible, heating melting, then mass fraction is taken to account for The amine-terminated hyperbrancedization resin that the first step of uncured rubber asphalt waterproof coating 5% obtains is added in crucible, then in temperature It stirs evenly, is applied to later on the long generous respectively aluminium sheet of 100mm*50mm*2mm under conditions of being 150 DEG C, it is cooling For 24 hours, then with processing 2h ± 15min in the baking oven at horizontal plane angle at 45 °, the temperature that record sliding occurs at first, trickles, drips Degree.
Implementation two
（1）Weigh 13.60g（0.1mol）Pentaerythrite, 53.65g（0.4mol）2,2-dihydromethyl propionic acids, first by season penta Tetrol and 2,2-dihydromethyl propionic acids are added in the four-hole boiling flask with magnetic stirring apparatus, add appropriate N, N-dimethyl methyl Amide makes it dissolve, and adds 0.80g p-methyl benzenesulfonic acids, is warming up to 140 DEG C, synthesis under normal pressure 1.5h；65 DEG C are cooled to, then 139.20g is added（0.8mol）2,4-toluene-2,4-diisocyanates react under dibutyltindilaurate catalyzed and nitrogen protection 4h；Add 119.20g（0.8mol）Triethanolamine, react 4h, add 278.40g（1.6mol）2,4-diisocyanates Toluene ester reacts 4h；Near room temperature, is slowly added to 480.00g amido silicon oils, reaction 3h both amine-terminated hyperbrancedization resin.
（2）A certain amount of uncured rubber asphalt waterproof coating is taken to be added in crucible, heating melting, then mass fraction is taken to account for The amine-terminated hyperbrancedization resin that the first step of uncured rubber asphalt waterproof coating 5% obtains is added in crucible, then in temperature It stirs evenly, is applied to later on the long generous respectively aluminium sheet of 100mm*50mm*2mm under conditions of being 150 DEG C, it is cooling For 24 hours, then with processing 2h ± 15min in the baking oven at horizontal plane angle at 45 °, the temperature that record sliding occurs at first, trickles, drips Degree.
Implementation three
（1）Weigh 13.60g（0.1mol）Pentaerythrite, 53.65g（0.4mol）2,2-dihydromethyl propionic acids, first by season penta Tetrol and 2,2-dihydromethyl propionic acids are added in the four-hole boiling flask with magnetic stirring apparatus, add appropriate N, N-dimethyl methyl Amide makes it dissolve, and adds 0.80g p-methyl benzenesulfonic acids, is warming up to 140 DEG C, synthesis under normal pressure 1.5h；65 DEG C are cooled to, then 139.20g is added（0.8mol）2,4-toluene-2,4-diisocyanates react under dibutyltindilaurate catalyzed and nitrogen protection 4h；Add 119.20g（0.8mol）Triethanolamine, react 4h, add 278.40g（1.6mol）2,4-diisocyanates Toluene ester reacts 4h；Near room temperature, is slowly added to 480.00g amido silicon oils, reaction 3h both amine-terminated hyperbrancedization resin.
（2）A certain amount of uncured rubber asphalt waterproof coating is taken to be added in crucible, heating melting, then mass fraction is taken to account for The amine-terminated hyperbrancedization resin that the first step of uncured rubber asphalt waterproof coating 10% obtains is added in crucible, then in temperature Degree stirs evenly under conditions of being 150 DEG C, is applied to later on the long generous respectively aluminium sheet of 100mm*50mm*2mm, cold But for 24 hours, then with processing 2h ± 15min in the baking oven at horizontal plane angle at 45 °, the temperature that record sliding occurs at first, trickles, drips Degree.
Implementation four
（1）Weigh 13.60g（0.1mol）Pentaerythrite, 53.65g（0.4mol）2,2-dihydromethyl propionic acids, first by season penta Tetrol and 2,2-dihydromethyl propionic acids are added in the four-hole boiling flask with magnetic stirring apparatus, add appropriate N, N-dimethyl methyl Amide makes it dissolve, and adds 0.80g p-methyl benzenesulfonic acids, is warming up to 140 DEG C, synthesis under normal pressure 1.5h；65 DEG C are cooled to, then 139.20g is added（0.8mol）2,4-toluene-2,4-diisocyanates react under dibutyltindilaurate catalyzed and nitrogen protection 4h；Add 119.20g（0.8mol）Triethanolamine, react 4h, add 278.40g（1.6mol）2,4-diisocyanates Toluene ester reacts 4h；Near room temperature, is slowly added to 480.00g amido silicon oils, reaction 3h both amine-terminated hyperbrancedization resin.
（2）A certain amount of uncured rubber asphalt waterproof coating is taken to be added in crucible, heating melting, then mass fraction is taken to account for The amine-terminated hyperbrancedization resin that the first step of uncured rubber asphalt waterproof coating 15% obtains is added in crucible, then in temperature Degree stirs evenly under conditions of being 150 DEG C, is applied to later on the long generous respectively aluminium sheet of 100mm*50mm*2mm, cold But for 24 hours, then with processing 2h ± 15min in the baking oven at horizontal plane angle at 45 °, the temperature that record sliding occurs at first, trickles, drips Degree.
Comparison is implemented
A certain amount of uncured rubber asphalt waterproof coating is taken to be added in crucible, it is generous to be applied to length later for heating melting Respectively on the aluminium sheet of 100mm*50mm*2mm, it is cooling for 24 hours, then with handled in the baking oven at horizontal plane angle at 45 ° 2h ± There is sliding, trickling, the temperature dripped at first in 15min, record.
Performance test
It is exactly to be added to the hyperbranched resin obtained in implementation of the present invention below in order to illustrate the actual effect of the present invention In uncured rubber asphalt waterproof coating, high temperature resistance detection is carried out.
Test performance such as the following table 1.
1. uncured rubber asphalt waterproof coating of table trickling temperature
Hyperbranched resin Trickling temperature/DEG C
Comparison is implemented 71
Implementation one（5%） 83
Implementation two（5%） 85
Implementation three（10%） 100
Implementation four（15%） 117
As shown in Table 1, after adding the made amine-terminated hyperbrancedization resin of the present invention, the uncured rubber asphalt prepared is anti- Water paint high temperature resistance compared with hyperbranched resin is not added has apparent improvement.Wherein when addition content is 5%, the Two generation hyperbranched resins are slightly better than the first generation；With the increase of second generation hyperbranched resin addition content, uncured rubber asphalt is anti- Water paint high temperature resistance is greatly improved.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not limited by embodiment System, other any changes made without departing from the spirit and principles of the present invention, modification, combination, replacement, simplification should be Equivalence replacement mode, is included within the scope of the present invention.

Claims (9)

1. a kind of preparation method for improving the hyperbranched resin of uncured rubber asphalt high temperature resistance, it is characterised in that institute It states hyperbranched resin branch terminals and contains a large amount of amino.
2. preparation method according to claim 1, it is characterised in that the Hyperbranched Polymer with Terminal Amido is by following What step obtained：
2,2-dihydromethyl propionic acids of 3 ~ 4.5 times of polyalcohol and polyalcohol molal quantity are added under nitrogen protection after mixing Heat is to 140 ~ 170 DEG C, 1.5 ~ 2h of synthesis under normal pressure；Then be added isocyanates and triethanolamine be heated to 60 under nitrogen protection ~ 70 DEG C, react 4h；Then it adds Amino End Group silicone oil and 3h is stirred at room temperature.
3. preparation method according to claim 1, it is characterised in that the polyalcohol is trimethylolpropane, the third three Alcohol, butantriol, triethanolamine, one or more of pentaerythrite.
4. preparation method according to claim 1, it is characterised in that the isocyanates is 2,4-toluene di-isocyanate (TD.I)s One or more of ester, 4,4-methyl diphenylene diisocyanates, isophorone diisocyanate.
5. preparation method according to claim 1, it is characterised in that the isocyanate terminated hyperbranched resin of the difference algebraically, Wherein the first generation, the second generation, the third generation, forth generation polyalcohol and isocyanates molar ratio are 1:6~8、1:18~24、1:42 ~56、1:90~120。
6. preparation method according to claim 1, it is characterised in that the isocyanate terminated hyperbranched resin of the difference algebraically, Wherein the first generation, the second generation, the third generation, forth generation polyalcohol and triethanolamine molar ratio are 1:0、1:6~8、1:18~24、 1:42~56。
7. preparation method according to claim 1, it is characterised in that the isocyanate terminated hyperbranched resin of the difference algebraically, Wherein the first generation, the second generation, the third generation, forth generation polyalcohol and isocyanate terminated molar ratio are 1:6~8、1:12~16、1:24~ 32、1:48~64。
8. preparation method according to claim 1, it is characterised in that the weight average molecular weight of the Amino End Group silicone oil is 300 ~ 1000, and the amino containing 0.1 ~ 2w%.
9. preparation method according to claim 1, it is characterised in that the Amino End Group silicone oil is DOW CORNING CM-226, road One or more of healthy and free from worry OFX-8040A, DOW CORNING OFX-8803.
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CN109161009B (en) * 2018-09-04 2020-12-11 济南大学 Preparation and application of hyperbranched organic silicon polymer
CN109824909A (en) * 2019-02-27 2019-05-31 济南大学 A kind of preparation and its application of organic-silicon-modified hyper-branched polyester-amide resin
CN109824909B (en) * 2019-02-27 2020-10-27 济南大学 Preparation and application of organic silicon modified hyperbranched polyester-amide resin
CN111548734A (en) * 2020-05-27 2020-08-18 潍坊石花化工建材有限公司 Normal-temperature construction type non-cured rubber asphalt waterproof coating and preparation method thereof

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