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CN109206591B - Water-based blocked polyisocyanate crosslinking agent and preparation method thereof - Google Patents

Water-based blocked polyisocyanate crosslinking agent and preparation method thereof Download PDF

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CN109206591B
CN109206591B CN201710535295.6A CN201710535295A CN109206591B CN 109206591 B CN109206591 B CN 109206591B CN 201710535295 A CN201710535295 A CN 201710535295A CN 109206591 B CN109206591 B CN 109206591B
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blocked polyisocyanate
polyisocyanate crosslinking
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CN109206591A (en
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韦军
孙祥
吕剑伟
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Yancheng Shengkang New Material Technology Co ltd
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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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8041—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3271
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • 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
    • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
    • C08G18/724—Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates
    • 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
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • 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
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates

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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 invention discloses a water-based blocked polyisocyanate crosslinking agent with high deblocking temperature and a preparation method thereof. The isocyanate tripolymer and hydroxyethyl ethylenediamine are reacted under the ice bath condition to prepare a branched polymer skeleton, then aromatic diisocyanate and the polymer skeleton are reacted to obtain a prepolymer blocked by an isocyanate group, finally trimethyl hydroxyethyl ethylenediamine is used for blocking the residual active isocyanate group, and organic acid is used for neutralizing to obtain a water-based blocked polyisocyanate crosslinking agent with high deblocking temperature.

Description

Water-based blocked polyisocyanate crosslinking agent and preparation method thereof
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to a water-based closed polyisocyanate crosslinking agent and a preparation method thereof.
Background
Petersen reported blocking of isocyanate (NCO) group for the first time as early as 1949, and then Wicks (Blocked isocynate [ J ]. progress in organic coatings,1975,3:73-99) reviewed the blocking of isocyanate and its use in detail. Compared with a non-blocked polyisocyanate crosslinking agent, the blocked polyisocyanate crosslinking agent solves the problems of high reactivity of isocyanate groups, high sensitivity to moisture, short service life after being mixed with resin and the like. Nowadays, with increasingly sound laws and regulations on reducing the VOC content of a coating, the development of water-based coatings has become a mainstream trend, but compared with solvent-based coatings, water-based coatings have the problems of poor water resistance, solvent resistance and high temperature resistance, so that a water-based blocked polyisocyanate crosslinking agent has become a focus of attention in order to improve the physical and mechanical properties of the coating.
Generally, the preparation method of the water-based blocked polyisocyanate crosslinking agent is to introduce ionic or nonionic hydrophilic groups into the main chain or branched chain structure of a macromolecule, such as Lv mussel and the like (preparation of the blocked water-based polyisocyanate curing agent and performance research [ J ] coating industry, 2007,37(12):17-19) to react isophorone diisocyanate (IPDI) tripolymer with nonionic hydrophilic chain extender glycol monomethyl ether to obtain isocyanate-terminated prepolymer, and then to prepare the blocked water-based polyisocyanate curing agent by using methyl ethyl ketone oxime as a blocking agent, so that the water resistance, solvent resistance and mechanical properties of a cured water-based polyurethane coating film are obviously improved; wang et al synthesized prepolymers from IPDI and Triethanolamine (TEOA), and then obtained cationic blocked polyisocyanate crosslinkers with Butanol (BAO) and 3, 5-Dimethylpyrazole (DMP) as blocking agents, which better satisfied the curing properties of the resin when DMP was used as a blocking agent. However, there are few reports on the related studies of improving the hydrophilicity of the whole cross-linking agent molecule by the hydrophilicity of the terminal group.
Disclosure of Invention
The invention starts from the design of molecular structure, firstly utilizes the reaction activity difference of isocyanate tripolymer and different active hydrogen to prepare branched polymer skeleton, then uses high-activity aromatic diisocyanate to react with the polymer skeleton to obtain isocyanate group-terminated prepolymer, simultaneously introduces aromatic ring structure into the cross-linking agent structure, is favorable for improving the mechanical property of the later-stage cured coating, finally adds hydrophilic sealing agent, uses organic acid to neutralize, utilizes the high hydrophilicity of the end group to realize the water dispersibility of the cross-linking agent, prepares a water-based closed polyisocyanate cross-linking agent, and has higher application and research values in the aspects of cathode electrophoretic coating, baking varnish and the like.
The chemical structural formula of the water-based blocked polyisocyanate crosslinking agent is shown as follows:
Figure GDA0003050845910000021
in the formula:
Figure GDA0003050845910000022
Figure GDA0003050845910000023
R1＝HCOO、CH3COO、HCOOCOO。
the preparation method of the water-based blocked polyisocyanate crosslinking agent comprises the following steps: all are expressed in parts by mass
Under the protection of nitrogen and the action of mechanical stirring, 18.0-21.0 parts of organic solvent and 9.7-13.3 parts of isocyanate trimer are added into a four-mouth flask, 1.8-3.2 parts of organic solvent and 1.0-1.1 parts of hydroxyethyl ethylene diamine are dropwise added into a system within 0.1-0.5 h under the condition of ice bath, the reaction is carried out for 0.5-1.0 h until the NCO content reaches a theoretical value, then 2.0-4.0 parts of organic solvent and 3.5-5.0 parts of diisocyanate are added, the temperature is increased to 40-50 ℃, the reaction is carried out for 1.0-1.5 h under the condition of heat preservation, the NCO content reaches the theoretical value, then 7.7-8.0 parts of trimethyl hydroxyethyl ethylene diamine are added within 0.2-0.5 h, the reaction is carried out for 2.0-3.0 h under the condition of heat preservation, finally the reaction is carried out to the room temperature, 4.4-9.0 parts of organic acid is added, and the stirring is carried out for 0.2-0.5 h, so as to obtain the water-based crosslinking type polyisocyanate.
The organic solvent in the preparation method is selected from butanone, cyclohexanone or 1, 4-dioxane; the isocyanate trimer is selected from hexamethylene diisocyanate trimer or isophorone diisocyanate trimer; the diisocyanate is selected from toluene diisocyanate or diphenylmethane diisocyanate; the organic acid is selected from formic acid, glacial acetic acid or oxalic acid.
The preparation reaction equation of the water-based blocked polyisocyanate crosslinking agent can be expressed as follows:
Figure GDA0003050845910000031
in the formula:
Figure GDA0003050845910000041
Figure GDA0003050845910000042
R1＝HCOO、CH3COO、HCOOCOO。
the preparation method of the water-based closed polyisocyanate crosslinking agent comprises the steps of reacting isocyanate tripolymer with two amino groups in hydroxyethyl ethylenediamine under an ice bath condition, then reacting with the rest hydroxyl groups by utilizing the high reaction activity of aromatic diisocyanate to form an NCO-terminated prepolymer, then adding a hydrophilic closing agent trimethyl hydroxyethyl ethylenediamine, and neutralizing by organic acid to obtain the water-based closed polyisocyanate crosslinking agent, and the water-based closed polyisocyanate crosslinking agent has wide application prospects in the aspects of cathode electrophoretic coating, baking varnish and the like.
Drawings
FIG. 1 shows an infrared spectrum of an aqueous blocked polyisocyanate crosslinking agent.
FIG. 2 shows an IR spectrum of a water-based blocked polyisocyanate crosslinking agent after deblocking at 180 ℃.
Detailed Description
The invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the description of the embodiments is only for illustrating the present invention and should not be taken as limiting the invention as detailed in the claims.
Example 1
Under the protection of nitrogen and the action of mechanical stirring, 21.0 parts of cyclohexanone and 12.9 parts of isophorone diisocyanate trimer are added into a four-neck flask, 2.0 parts of cyclohexanone and 1.1 parts of hydroxyethyl ethylenediamine are added into the system dropwise within 0.2h under the condition of ice bath, the heat preservation reaction is carried out for 0.5h, then 3.0 parts of cyclohexanone and 3.5 parts of toluene diisocyanate are added, the temperature is raised to 50 ℃, the heat preservation reaction is continued for 1.0h, 7.7 parts of trimethyl hydroxyethyl ethylenediamine is added into the system after 0.3h, the heat preservation reaction is carried out for 3.0h, finally the temperature is cooled to the room temperature, 5.7 parts of glacial acetic acid are added, and the stirring is carried out for 0.2h, so as to obtain the water-based blocked polyisocyanate crosslinking agent. Storage at normal temperatureThe storage time is more than 6 months, the solid content is 50 percent, and the isocyanate content is 6.80 percent; FT-IR (KBr, cm)-1)：3320(N-H)，2930(-CH3,-CH2-), 1710(C ═ O), 1540(C-N), 1070 (C-O-C); FIG. 1 is an infrared spectrum of an aqueous blocked polyisocyanate crosslinking agent obtained; FIG. 2 shows an IR spectrum of a water-based blocked polyisocyanate crosslinking agent after deblocking at 180 ℃.
Example 2
Under the protection of nitrogen and the action of mechanical stirring, 19.0 parts of 1, 4-dioxane and 10.1 parts of hexamethylene diisocyanate trimer are added into a four-neck flask, 2.0 parts of 1, 4-dioxane and 1.1 parts of hydroxyethyl ethylene diamine are dropwise added into the system within 0.3h under the condition of ice bath, the system is kept warm and reacts for 1.0h, then 3.0 parts of 1, 4-dioxane and 5.0 parts of diphenylmethane diisocyanate are added, the temperature is raised to 50 ℃, after the system is kept warm and reacts for 1.0h, 8.0 parts of trimethyl hydroxyethyl ethylene diamine is added into the system within 0.5h, the system is kept warm and reacts for 3.0h, finally the system is cooled to the room temperature, 9.0 parts of oxalic acid is added, and the system is stirred for 0.3h, so that the water-based closed polyisocyanate crosslinking agent is obtained. The storage time at normal temperature exceeds 6 months, the solid content is 50 percent, and the isocyanate content is 6.96 percent.

Claims (3)

1. A water-based blocked polyisocyanate crosslinking agent is characterized by having the following structural formula:
Figure FDA0003015098560000011
in the formula:
Figure FDA0003015098560000012
Figure FDA0003015098560000013
Figure FDA0003015098560000014
R1＝HCOO、CH3COO、HCOOCOO。
2. the process for preparing a water-based blocked polyisocyanate crosslinking agent according to claim 1, which comprises the following steps: adding 18.0-21.0 parts of organic solvent and 9.7-13.3 parts of isocyanate trimer into a four-neck flask under the protection of nitrogen and the action of mechanical stirring, dropwise adding 1.8-3.2 parts of organic solvent and 1.0-1.1 parts of hydroxyethyl ethylenediamine into the system within 0.1-0.5 h under the condition of ice bath, reacting for 0.5-1.0 h until the NCO content reaches the theoretical value, then adding 2.0-4.0 parts of organic solvent and 3.5-5.0 parts of diisocyanate, heating to 40-50 ℃, carrying out heat preservation reaction for 1.0-1.5 h to enable the NCO content to reach the theoretical value, then adding 7.7-8.0 parts of trimethyl hydroxyethyl ethylenediamine into 0.2-0.5 h, carrying out heat preservation reaction for 2.0-3.0 h, finally cooling to room temperature, adding 4.4-9.0 parts of organic acid, stirring for 0.2-0.5 h, and obtaining the water-based crosslinking agent.
3. The process for preparing water-based blocked polyisocyanate crosslinking agent according to claim 2, wherein the organic solvent is selected from butanone, cyclohexanone or 1, 4-dioxane.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4540765A (en) * 1983-05-27 1985-09-10 Bayer Aktiengesellschaft Polyurethanes containing perfluoroalkyl groups and a process for their production
CN1572811A (en) * 2003-06-23 2005-02-02 拜尔材料科学股份公司 Blocked polyisocyanates
CN1813018A (en) * 2003-06-27 2006-08-02 拜尔材料科学股份公司 Blocked polyisocyanates
CN104448234A (en) * 2014-12-08 2015-03-25 盐城工学院 Waterborne blocked hyperbranched polyisocyanate cross-linking agent and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4540765A (en) * 1983-05-27 1985-09-10 Bayer Aktiengesellschaft Polyurethanes containing perfluoroalkyl groups and a process for their production
CN1572811A (en) * 2003-06-23 2005-02-02 拜尔材料科学股份公司 Blocked polyisocyanates
CN1813018A (en) * 2003-06-27 2006-08-02 拜尔材料科学股份公司 Blocked polyisocyanates
CN104448234A (en) * 2014-12-08 2015-03-25 盐城工学院 Waterborne blocked hyperbranched polyisocyanate cross-linking agent and preparation method thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Blocked isocyanates: an efficient tool for post-polymerization modification of polymers;Stefan Bode,等;《polymer chemistry》;20141231;第5卷(第7期);第2574-2582页 *
聚氨基醇胺类染色织物耐洗色牢度提升剂的合成及应用;从建华，等;《印染助剂》;20070520;第24卷(第5期);第25-27页 *
阳离子水性封闭型聚异氰酸酯交联剂的制备与性能;孙祥，等;《涂料工业》;20160531;第46卷(第5期);第60-64页 *

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