CN111303378A - TMXDI-based polyurethane anti-sagging resin and preparation method thereof - Google Patents
TMXDI-based polyurethane anti-sagging resin and preparation method thereof Download PDFInfo
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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- 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
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- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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Abstract
The invention relates to an anti-Sagging (SCA) resin based on TMXDI (tetramethylxylylene diisocyanate) polyurethane resin as a matrix. The method is characterized in that: (1) adding three raw materials of a solvent A, dimethylolpropionic acid and a hydroxyl polymer into a reaction kettle, heating to 60 ℃, preserving heat, and completely dissolving dimethylolpropionic acid solid particles in the reaction kettle; (2) adding DBTL (dibutyltin dilaurate), slowly dropwise adding TMXDI, controlling the temperature to be 65-70 ℃, reacting to prepare a prepolymer, (3) adding a certain amount of benzylamine, TMXDI and a solvent B into a reaction kettle, and stirring for 1 hour to react to obtain the SCA anti-sagging resin. The SCA resin synthesized by the invention has the advantages that the matrix resin is polyurethane resin, the content of isocyanate (NCO) groups is controllable, the content of effective components of polyurea crystals is controllable, and the anti-sagging performance is good.
Description
Technical Field
The invention belongs to the technical field of preparation of high polymer materials, and relates to TMXDI (tetramethylenediamine) -based polyurethane anti-sagging resin and a preparation method thereof, in particular to an auxiliary resin for preventing sagging defects of baking paint.
Background
When the high molecular coating is used in construction, the high molecular coating has lower viscosity, and is beneficial to the flowing of a high molecular film and easy construction, so that the high molecular film is fully leveled. However, the reduction in viscosity means that sagging tends to occur on a vertical plane, and it is desired to provide a coating material having a high viscosity and reduced fluidity to avoid the sagging. The requirement is that the coating has a balance point between leveling and sagging, so that the coating can recover to a high viscosity action state under the action of high shear force after construction to prevent the sagging phenomenon even if the coating has certain leveling property under the action of high shear force during construction.
The addition of the SCA anti-sagging resin is one of the methods for improving the anti-sagging performance of the coating. SCA is short for Sag control agent, and means sagging control aid. The principle is the formation of polyurea compounds, i.e. SCA crystals, in the resin. The SCA resin consists of two parts of matrix resin solution and SCA crystal. The molecular structure of the SCA crystal is easy to form hydrogen bonds, and when no external force or small external force is generated, the coating has high viscosity under the action of a large number of hydrogen bonds, so that the coating is not easy to sag. When certain shearing force exists, the hydrogen bond is broken, and the adhesive shows very low viscosity, is easy to flow and is easy to construct.
TMXDI is an abbreviation for (tetramethylxylylene diisocyanate). Due to the effect of steric hindrance, the viscosity of the corresponding polymer prepared by TMXDI is much lower than that of the polymer prepared by other isocyanate, and the viscosity stability is also good. The shielding effect of the methyl groups prevents the isocyanate from condensing to allophanates, biurets or isocyanurates. The absence of side reactions and the low reactivity of the tertiary isocyanate with the carboxyl groups of the hydrophilic compound allows the synthesis of prepolymers that react with polyols at higher temperatures without crosslinking and without side reactions.
The Nippon paint (China) Ltd uses an acrylic resin to synthesize a sag resistant resin in patent application No. 201710798093.0. The acrylate copolymer is of a homogeneous structure, and the performance difference of the acrylate copolymer is greatly determined by the difference of the structure. Acrylic resins have a single glass transition temperature and are inferior in abrasion resistance to polyurethane resins. The anti-sagging resin was synthesized by Kyosu Karen building materials Co.Ltd using MDI (diphenylmethane diisocyanate) and TDI (toluene diisocyanate) in patent application No. 201610663733.2. MDI and TDI are aromatic isocyanate and have defects in yellowing resistance and weather resistance. The SCA resin invented by Allnex company is polyurea crystal formed by reacting HDI with benzylamine in matrix resin, and the matrix resin and the effective component of SCA have no chemical bond connection, but are physically mixed.
According to the SCA resin, aliphatic TMXDI is used as an isocyanate part, a prepolymer synthesized with a hydroxyl polymer is lower in viscosity and is aliphatic isocyanate, the advantages of being not easy to age and resistant to yellowing are achieved, meanwhile, the prepolymer contains partial isocyanate groups, the prepolymer can continuously react with benzylamine to form polyurea groups, and the polyurea groups participate in SCA crystals, and therefore compatibility of matrix resin and the SCA crystals is better. Except the interaction of urea bonds, TMXDI molecules and benzylamine molecules contain benzene rings, and the benzene rings and the urea bonds have large pi bond interaction, so that the TMXDI SCA crystal has stronger sagging prevention performance.
In view of this, the TMXDI synthesized sag resistant resin has good sag resistance and practical performance, and has a good commercial prospect.
Disclosure of Invention
The invention adopts aliphatic TMXDI as an isocyanate part, and synthesizes a prepolymer with hydroxyl polymer and dimethylolpropane as raw materials, and then benzylamine and TMXDI are added to react to form polyurea, polyurea molecules are aggregated to form SCA crystals under the action of hydrogen bonds, and the anti-sagging resin which takes polyurethane resin as matrix resin and polyurea crystals as effective components is formed.
The viscosity of the polyurethane prepolymer synthesized by TMXDI is lower than that of a prepolymer synthesized by using other isocyanate, the polyurethane prepolymer is aliphatic isocyanate and has the advantages of difficult aging and yellowing resistance, and meanwhile, the prepolymer contains partial unreacted isocyanate groups and can continuously react with benzylamine to form polyurea groups to participate in SCA crystals, so that the compatibility of matrix resin and the SCA crystals is better. Except the interaction of urea bonds, TMXDI molecules and benzylamine molecules contain benzene rings, and the large pi bond between the benzene rings and the urea bonds has stronger sagging prevention performance.
The preparation process of the SCA sag resistant resin of the present invention, as described below,
(1) adding three raw materials of acetone, dimethylolpropionic acid and hydroxyl polymer into a reaction kettle, heating to 60 ℃, and preserving heat for 1h to completely dissolve dimethylolpropionic acid solid particles in the reaction kettle;
(2) then adding DBTL, slowly TMXDI in 1 hour through a dropping funnel, and controlling the temperature at 65-70 ℃;
(3) after the dripping is finished, controlling the temperature to react at 60 ℃, sampling every 2 hours, and measuring the NCO value;
(4) and (3) after the NCO value reaches a target value, cooling to below 25 ℃, adding a sagging control agent consisting of benzylamine and TMXDI into the prepolymer, then adding an organic solvent, and stirring for 1h to obtain the SCA sagging resistant resin.
The following examples and the like are provided to further clarify the features of the present invention. However, the present invention is not limited to these examples.
Drawings
FIG. 1 is a scanning electron micrograph of the SCA crystals of example 1E.
Fig. 2 is a rheological plot of the different crystal contents of example 1.
Detailed Description
Example 1: synthesis of SCA resins of different crystal contents
SCA resins with different crystal contents were prepared according to the following procedure with the material ratios in the following table.
Table one: examples 1A-E Material ratios
The preparation method comprises the following steps:
(1) firstly, DESMOPHEN 670 is put into a 60 ℃ oven to be preheated to be liquid, and then three raw materials of acetone, dimethylolpropionic acid and DESMOPHEN 670 are added into a four-neck flask provided with a stirrer, a thermometer and a reflux condenser tube. Starting stirring, condensing water, heating to 60 ℃, and preserving heat for 1 hour to completely dissolve dimethylolpropionic acid solid;
(2) then adding DBTL, slowly TMXDI in 1 hour through a dropping funnel, observing the heat release condition, controlling the temperature at 65-70 ℃, controlling the feeding speed according to the temperature change condition, and recording the temperature rise condition. After the dropwise addition is finished, the dropping funnel is washed by acetone, the temperature is controlled to be kept at 60 ℃, samples are taken every 2 hours, and the NCO value is measured;
(3) and after the NCO value is qualified, adding benzylamine and a second part of TMXDI into the prepolymer, then adding dimethylbenzene, and fully stirring for 1 h.
The sample of example 1E was characterized using scanning electron microscopy, and as can be seen from the scanning electron micrograph of FIG. 1, the polyurea molecules formed elongated acicular crystals. All samples from example 1 were tested using an antopa rheometer and as can be seen from the data in fig. 2, the samples were lower in viscosity at high shear and increased in viscosity when changed to low shear, indicating thixotropy of the samples prepared and increased thixotropy with increasing crystal content.
Claims (4)
1. The anti-sagging TMXDI-based polyurethane resin is characterized in that TMXDI is used as an isocyanate component to synthesize a polyurethane prepolymer, the NCO group content of the prepolymer is controllable, the viscosity of the prepolymer is lower than that of the prepolymer synthesized by other types of isocyanates, and the subsequent reaction is facilitated.
2. The TMXDI-based polyurethane anti-sagging resin and the preparation method thereof as claimed in claim 1, wherein the hydroxyl polymer is one or more of polyester diol, polyether diol, polycarbonate diol, polyester polyol, polyether polyol; for example, PPG2000, PEG1000, DESMOPHEN 670, DESMOPHEN C1200, DESMOPHEN 2202, and the like.
3. The TMXDI-based polyurethane anti-sagging resin and the preparation method thereof as claimed in claim 1, wherein the TMXDI-based polyurethane anti-sagging resin is prepared from the following raw materials in parts by weight: 8-20% of solvent A, 0.005-0.01% of DBTL, 4.5-5.0% of dimethylolpropionic acid, 12-34% of hydroxyl polymer, 11.0-25% of TMXDI, 0.5-8.0% of benzylamine, 0.5-6.5% of TMXDI and 8-20% of solvent B.
4. The TMXDI-based polyurethane anti-sagging resin and the preparation method thereof as set forth in claim 3, wherein the solvent A is one or more of acetone, N-methyl pyrrolidone, methyl isoamyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, N-ethyl pyrrolidone and butanone; the solvent B is one or more of naphtha, heptane, normal butanol, butyl acetate, dimethylbenzene and ethylene glycol monobutyl ether.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286954A (en) * | 2022-09-02 | 2022-11-04 | 长兴化学工业(中国)有限公司 | Sag control agents and coating compositions containing the same |
| CN116239713A (en) * | 2023-03-03 | 2023-06-09 | 天津大学 | Sagging-resistant resin and preparation method and application thereof |
| CN116444700A (en) * | 2023-03-03 | 2023-07-18 | 天津大学 | Sagging-resistant resin, preparation method and application thereof in preparing high-temperature baking paint coating |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115286954A (en) * | 2022-09-02 | 2022-11-04 | 长兴化学工业(中国)有限公司 | Sag control agents and coating compositions containing the same |
| CN115286954B (en) * | 2022-09-02 | 2023-05-09 | 长兴化学工业(中国)有限公司 | Sagging control agent and coating composition containing same |
| CN116239713A (en) * | 2023-03-03 | 2023-06-09 | 天津大学 | Sagging-resistant resin and preparation method and application thereof |
| CN116444700A (en) * | 2023-03-03 | 2023-07-18 | 天津大学 | Sagging-resistant resin, preparation method and application thereof in preparing high-temperature baking paint coating |
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