CN106543408A - The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane - Google Patents

The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane Download PDF

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Publication number
CN106543408A
CN106543408A CN201611139190.0A CN201611139190A CN106543408A CN 106543408 A CN106543408 A CN 106543408A CN 201611139190 A CN201611139190 A CN 201611139190A CN 106543408 A CN106543408 A CN 106543408A
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methyl hydride
glued membrane
dicyclohexyl methyl
aqueous polyurethane
type aqueous
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CN201611139190.0A
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王耀斌
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Shaanxi Gaoxin Industry Co Ltd
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Shaanxi Gaoxin Industry Co Ltd
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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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • 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
    • C08G18/65—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
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/65—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
    • 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
    • C08G18/65—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
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/65—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
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
    • 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
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane of the present invention, is related to polyurethane industrial field, and in particular to the preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane, comprises the following steps：In equipped with agitator, reflux condensing tube, the 500mL four-hole boiling flasks of thermocouple, add dicyclohexyl methyl hydride diisocyanate, polyethers or PEPA and catalyst dibutyltindilaurylmercaptide cinnamic acid, and about 1 h is reacted under 80 degree, determine NCO content, when mass fraction 9.43% is reached, prepolymerization reaction terminates；Prepolymer is cooled to into 70 degree, addition is dissolved in dihydromethyl propionic acid, Isosorbide-5-Nitrae butanediol and the acetone of N methyl pyrrolidones, carries out chain extending reaction, when NCO mass fractions reach 2.30%, chain extending reaction terminates, and the present invention is simple to operate, convenient to process, and can guarantee that product quality, enhance product performance, cost-effective, reducing energy consumption.

Description

The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane
Technical field
The present invention relates to polyurethane industrial field, and in particular to dicyclohexyl methyl hydride diisocyanate type water-borne polyurethane bond The preparation method of film.
Background technology
Dicyclohexyl methyl hydride diisocyanate does not contain phenyl ring due to molecular structure, therefore the product not easy oxidation discoloration of production, It is usually used in preparing casting elastomer and other has the coating of favorable elasticity, optical transparence and light stability.The poly- ammonia of aqueouss Ester (WPU) coating is due to nonflammable, nontoxic, advantages of environment protection, receiving much concern in recent years.By dicyclohexyl methyl hydride two Isocyanates are used to prepare WPU coating, its product in addition to above-mentioned advantage, also excellent mechanical property, chemical stability And weatherability.But rarely have the report with regard to dicyclohexyl methyl hydride diisocyanate type WPU glued membrane.
The content of the invention
Present invention aim at provide a kind of simple to operate, it is convenient to process, and product quality is can guarantee that, improve product Can, cost-effective, the preparation method of the dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane of reducing energy consumption.
The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane of the present invention, comprises the following steps：
The first step, in equipped with agitator, reflux condensing tube, the 500mL four-hole boiling flasks of thermocouple, adds dicyclohexyl methyl hydride two Isocyanates, polyethers or PEPA and catalyst dibutyltindilaurylmercaptide cinnamic acid, and about 1 h is reacted under 80 degree, determine NCO Content, when mass fraction 9.43% is reached, prepolymerization reaction terminates；
Prepolymer is cooled to 70 degree by second step, and addition is dissolved in dihydromethyl propionic acid, the Isosorbide-5-Nitrae-fourth two of N-Methyl pyrrolidone Alcohol and acetone, carry out chain extending reaction, and when NCO mass fractions reach 2.30%, chain extending reaction terminates, and above-mentioned reactant is lowered the temperature To 40 degree, room temperature is down to 0.5h in adding triethylamine, adds ethylenediamine, finally in 10000 r/ after deionized water emulsifying Emulsion is placed in horizontal glass plate and spontaneously dries 24 h, 70 degree of 4 h of oven drying, obtains bicyclo- by high-speed stirred under the conditions of min Hexyl methane diisocyanate type aqueous polyurethane glued membrane.
Preferably, in second step, dihydromethyl propionic acid is fed intake for substep with BDO and acetone feeding mode, that is, expand Dihydromethyl propionic acid is initially charged in chain process, BDO and acetone is added after its reaction completely.
Preferably, in second step, dihydromethyl propionic acid is fed intake for a step with BDO and acetone feeding mode, that is, expand Dihydromethyl propionic acid and BDO and the mixture of acetone are directly added in chain process, chain extending reaction is simultaneously participated in.
The present invention is simple to operate, convenient to process, and can guarantee that product quality, enhances product performance, cost-effective, reduces energy Consumption.
Specific embodiment
Embodiment one：
The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane of the present invention, comprises the following steps：
The first step, in equipped with agitator, reflux condensing tube, the 500mL four-hole boiling flasks of thermocouple, adds dicyclohexyl methyl hydride two Isocyanates, polyethers or PEPA and catalyst dibutyltindilaurylmercaptide cinnamic acid, and about 1 h is reacted under 80 degree, determine NCO Content, when mass fraction 9.43% is reached, prepolymerization reaction terminates；
Prepolymer is cooled to 70 degree by second step, and addition is dissolved in dihydromethyl propionic acid, the Isosorbide-5-Nitrae-fourth two of N-Methyl pyrrolidone Alcohol and acetone, carry out chain extending reaction, and when NCO mass fractions reach 2.30%, chain extending reaction terminates, and above-mentioned reactant is lowered the temperature To 40 degree, room temperature is down to 0.5h in adding triethylamine, adds ethylenediamine, finally in 10000 r/ after deionized water emulsifying Emulsion is placed in horizontal glass plate and spontaneously dries 24 h, 70 degree of 4 h of oven drying, obtains bicyclo- by high-speed stirred under the conditions of min Hexyl methane diisocyanate type aqueous polyurethane glued membrane.
Embodiment two：
The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane of the present invention, comprises the following steps：
The first step, in equipped with agitator, reflux condensing tube, the 500mL four-hole boiling flasks of thermocouple, adds dicyclohexyl methyl hydride two Isocyanates, polyethers or PEPA and catalyst dibutyltindilaurylmercaptide cinnamic acid, and about 1 h is reacted under 80 degree, determine NCO Content, when mass fraction 9.43% is reached, prepolymerization reaction terminates；
Prepolymer is cooled to 70 degree by second step, and addition is dissolved in dihydromethyl propionic acid, the Isosorbide-5-Nitrae-fourth two of N-Methyl pyrrolidone Alcohol and acetone, carry out chain extending reaction, and when NCO mass fractions reach 2.30%, chain extending reaction terminates, and above-mentioned reactant is lowered the temperature To 40 degree, room temperature is down to 0.5h in adding triethylamine, adds ethylenediamine, finally in 10000 r/ after deionized water emulsifying Emulsion is placed in horizontal glass plate and spontaneously dries 24 h, 70 degree of 4 h of oven drying, obtains bicyclo- by high-speed stirred under the conditions of min Hexyl methane diisocyanate type aqueous polyurethane glued membrane.
In second step, dihydromethyl propionic acid is fed intake for substep with BDO and acetone feeding mode, i.e., in chain extension process Dihydromethyl propionic acid is initially charged, and BDO and acetone is added after its reaction completely.
Embodiment three：
The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane of the present invention, comprises the following steps：
The first step, in equipped with agitator, reflux condensing tube, the 500mL four-hole boiling flasks of thermocouple, adds dicyclohexyl methyl hydride two Isocyanates, polyethers or PEPA and catalyst dibutyltindilaurylmercaptide cinnamic acid, and about 1 h is reacted under 80 degree, determine NCO Content, when mass fraction 9.43% is reached, prepolymerization reaction terminates；
Prepolymer is cooled to 70 degree by second step, and addition is dissolved in dihydromethyl propionic acid, the Isosorbide-5-Nitrae-fourth two of N-Methyl pyrrolidone Alcohol and acetone, carry out chain extending reaction, and when NCO mass fractions reach 2.30%, chain extending reaction terminates, and above-mentioned reactant is lowered the temperature To 40 degree, room temperature is down to 0.5h in adding triethylamine, adds ethylenediamine, finally in 10000 r/ after deionized water emulsifying Emulsion is placed in horizontal glass plate and spontaneously dries 24 h, 70 degree of 4 h of oven drying, obtains bicyclo- by high-speed stirred under the conditions of min Hexyl methane diisocyanate type aqueous polyurethane glued membrane.
In second step, dihydromethyl propionic acid is fed intake for a step with BDO and acetone feeding mode, i.e., in chain extension process Dihydromethyl propionic acid and BDO and the mixture of acetone are directly added into, chain extending reaction is simultaneously participated in.
The present invention is simple to operate, convenient to process, and can guarantee that product quality, enhances product performance, cost-effective, reduces energy Consumption.

Claims (3)

1. a kind of preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane, it is characterised in that include with Lower step：
The first step, in equipped with agitator, reflux condensing tube, the 500mL four-hole boiling flasks of thermocouple, adds dicyclohexyl methyl hydride two Isocyanates, polyethers or PEPA and catalyst dibutyltindilaurylmercaptide cinnamic acid, and about 1 h is reacted under 80 degree, determine NCO Content, when mass fraction 9.43% is reached, prepolymerization reaction terminates；
Prepolymer is cooled to 70 degree by second step, and addition is dissolved in dihydromethyl propionic acid, the Isosorbide-5-Nitrae-fourth two of N-Methyl pyrrolidone Alcohol and acetone, carry out chain extending reaction, and when NCO mass fractions reach 2.30%, chain extending reaction terminates, and above-mentioned reactant is lowered the temperature To 40 degree, room temperature is down to 0.5h in adding triethylamine, adds ethylenediamine, finally in 10000 r/ after deionized water emulsifying Emulsion is placed in horizontal glass plate and spontaneously dries 24 h, 70 degree of 4 h of oven drying, obtains bicyclo- by high-speed stirred under the conditions of min Hexyl methane diisocyanate type aqueous polyurethane glued membrane.
2. the preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane as claimed in claim 1, its feature It is that in second step, dihydromethyl propionic acid is fed intake for substep with BDO and acetone feeding mode, i.e., in chain extension process first Dihydromethyl propionic acid is added, and BDO and acetone is added after its reaction completely.
3. the preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane as claimed in claim 1, its feature Be that dihydromethyl propionic acid is fed intake for a step with BDO and acetone feeding mode in second step, i.e., it is straight in chain extension process Connect and add dihydromethyl propionic acid and BDO and the mixture of acetone, simultaneously participate in chain extending reaction.
CN201611139190.0A 2016-12-12 2016-12-12 The preparation method of dicyclohexyl methyl hydride diisocyanate type aqueous polyurethane glued membrane Pending CN106543408A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114395320A (en) * 2021-12-31 2022-04-26 唐山东方雨虹防水技术有限责任公司 Chemical anti-sagging exposed single-component polyurethane waterproof coating and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114395320A (en) * 2021-12-31 2022-04-26 唐山东方雨虹防水技术有限责任公司 Chemical anti-sagging exposed single-component polyurethane waterproof coating and preparation method thereof
CN114395320B (en) * 2021-12-31 2023-02-17 唐山东方雨虹防水技术有限责任公司 Chemical anti-sagging exposed single-component polyurethane waterproof coating and preparation method thereof

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