WO2014123434A1 - Mélange de prépolymère isocyanate à un constituant pour la production du produit polyuréthane dans un procédé en une étape - Google Patents

Mélange de prépolymère isocyanate à un constituant pour la production du produit polyuréthane dans un procédé en une étape Download PDF

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Publication number
WO2014123434A1
WO2014123434A1 PCT/PL2013/050002 PL2013050002W WO2014123434A1 WO 2014123434 A1 WO2014123434 A1 WO 2014123434A1 PL 2013050002 W PL2013050002 W PL 2013050002W WO 2014123434 A1 WO2014123434 A1 WO 2014123434A1
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WO
WIPO (PCT)
Prior art keywords
mixture
copolymer
component
butanol
mixtures
Prior art date
Application number
PCT/PL2013/050002
Other languages
English (en)
Inventor
Przemysław DWORNICKI
Tomasz Pawlus
Marufur Rahim
Original Assignee
"Selena Labs" Społka Z Ograniczona Odpowiedzialnoscia
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by "Selena Labs" Społka Z Ograniczona Odpowiedzialnoscia filed Critical "Selena Labs" Społka Z Ograniczona Odpowiedzialnoscia
Priority to PCT/PL2013/050002 priority Critical patent/WO2014123434A1/fr
Publication of WO2014123434A1 publication Critical patent/WO2014123434A1/fr

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Classifications

    • 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
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • 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
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • 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
    • C08G18/7657—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
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/141—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/142—Compounds containing oxygen but no halogen atom
    • 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
    • C08G2101/00—Manufacture of cellular products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/12—Organic compounds only containing carbon, hydrogen and oxygen atoms, e.g. ketone or alcohol
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2207/00—Foams characterised by their intended use
    • C08J2207/04—Aerosol, e.g. polyurethane foam spray
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • One component isocyanate prepolymer mixture for production in one step process of the polyurethane product isocyanate prepolymer mixture for production in one step process of the polyurethane product
  • Polyurethane prepolymers are used in a wide variety of industrial uses. Many of the systems are prepared from isocyanate systems which contain volatile isocyanate monomers, such as diphenylmethane diisocyanate (MDI) . Such uses include foams, adhesives, underbody coatings, automobile dampening systems, elastomeric parts and articles. There is a concern in industrial environments that exposure to volatile isocyanate monomers may be harmful to the workers' health. Therefore, there is a need to reduce the concentration of volatile isocyanate monomers in polyurethane precursors and prepolymers used in a variety of industrial applications.
  • volatile isocyanate monomers such as diphenylmethane diisocyanate (MDI)
  • MDI diphenylmethane diisocyanate
  • One solution known in the art is to strip the volatile isocyanate monomers from prepolymer systems using a distillation technique, such as a wipe-film evaporator. See, Anderson et al . , U.S. Patent 5,441, 808 at col. 6, lines 29-34. This solution adds an extra unit operation and therefore adds capital costs and operating costs to the production of such prepolymers.
  • Another solution known in the art involves preparing prepolymers in a two-step process wherein in the first step polyhydric alcohols are reacted with an asymmetric isocyanate having isocyanate groups of differing reactivity. The polyols preferentially react with the more reactive isocyanate group.
  • Component A was prepared by mixing at room temperature for 20 min adding the following ingredients: castor oil, ethylene glycol, dimorholino diethyl ether (DMDEE) , TCPP and silicone surfactant (Tegostab B8870) .
  • Component B was prepared separately by mixing at room temperature for 35min; a crude MDI (Supresec 5025) with 2-ethyl hexanol and after mixing these two components the NCO end-capped TDI Prepolymer is added and mixed. Then Component A and B were added into a can closed with a valve and the blowing agents were injected into the can. After that the can was shaken for 2-3 minutes.
  • the mentioned above method is a two step method of production of a low MDI OCF foam.
  • the first subject of the presented invention is one component isocyanate prepolymer mixture for production of the polyurethane product in one step process, said mixture having a content of free monomeric diphenylmethane diisocynate (MDI) of not more than 3%, preferably less than 2%, more preferably less than 1% of the total weight comprising
  • MDI free monomeric diphenylmethane diisocynate
  • the monofunctional alcohol has a low molar weight with Mw less than 130g/mol, preferably is a tertiary alcohol, more preferably is tert butanol, 2-metyl 2- butanol, n-butanol, isobutanol or their mixtures therein.
  • the propellant is a gas chosen from a group comprising dimethylether , isobutane and propane or their mixtures with the amount of gas or their mixtures from 20% to 50%, preferably from 22% to 40%, more preferably from 24% to 30%.
  • the catalyst amount is from 0,1% to 2%, preferably from 0,2% to 1,5%, more preferably from 0,3% to 1%.
  • a stabilizer with chemical composition of modified organosilicone copolymer is chosen from the group comprising silicone glycol copolymer (for instance Dabco DC198 or DC193 from Air Products), nonhydrolysable silicone glycol copolymer (for instance DC5000from Air Products , XXXXX (for instance Niax L-619 from Momentive) , siloxane polyalkyleneoxide copolymer (for instance Niax L-6164 from Momentive) , methylsiloxane polyalkyleneoxide copolymer (for instance Niax L-5348 from Momentive), polyetherpolysiloxane copolymer ( for instance Tegostab B8870 from Evonik) , poliether polydimethylsiloxane copolymer ( for instance Tegostab B8526 from Evonik), polyetersiloxane ( for instance Tegostab B8951 from Evonik) , polyether modified polysiloxane copolymer (for instance
  • the invention relates to a composition of one component foam (OCF) with low content of monomeric diisocyanate (2, 2 '-methyl diphenol isocyanate, 2, 4 '-methyl diphenol isocyanate and 4,4'- methyl diphenol isocyanate) .
  • This invention makes use of commercially available isocyanates, polyols, stabilizers which are common in OCF production.
  • One difference is that there is no need for using additional prepolymers in this invention compared to the state of art.
  • This process is based on a one step process.
  • the monomeric isocyanates are trapped by the addition of mono functional alcohol which is tertiary in nature.
  • the most preferred monofunctional alcohol is tert butanol or 2-methyl-2-butanol .
  • tertiary alcohol preferably tert butanol
  • Relative reaction rate of the tertiary alcohols is around 0,0125 and the reactivity of primary alcohols is 2,5 and the secondary is 0,75
  • the low reactivity of alcohol is better due to safety issues during one step production process.
  • a polyol blend was prepared by addition of a polyeter polyol which is commercially available as Rokopol G1000 (Rokita) , addition of polyester polyol which is commercially available as Alfaster T401 (Alfa Systems), addition of flame retardant TCPP, addition of chloroparafine 45, addition of propylene glycol, addition of monoalcohol - tertbutanol which is commercially available as Tebol 99 (LyondellBasell) , addition of stabilizer 1 and stabilizer 2 which can be chosen from the list of: Dabco DC198 (AirProducts) , Dabco DC193 (AirProducts ) , Dabco DC5000 (AirProducts), Niax L-6190 (Momentive) , Niax L-6164 (Momentive) , Niax L-5348 (Momentive) , Tegostab B8870 (Evonik) , Tegostab B8526 (Evonik), Tego
  • polyol blend was mixed in a closed hermetic vessel protected from moisture and mixed at room temperature for 10 min .
  • Polyol blend and technical diphenyl diisocyanate which has a NCO content around 31% by weight and is commercially available as Desmodure 44V20L (Bayer), Lupranat M20 (Basf) or Desmodure 44V70L (Bayer) were added to a disposable pressurized container.
  • Dimethylether and isobutane were introduced to the pressurized container which was subsequently shaken until fully mixing polyol blend with isocyanates.
  • the monomeric content was below 1% by weight, based on the composition as a whole.
  • the most important issue in the OCF foams is the viscosity of prepolymer in the pressurized container. It is known that monomeric MDI are good solvents for NCO prepolymers but in the disclosed invention the amount is less than 1%. That is why viscosity is higher in the foams containing low monomer content. To lower the viscosity of the foam prepolymer inside the pressurized vessel, it is important to add a higher amount of gases, especially dimethylether DME . In the present invention more than 25% of gases by weight are used. Dimethylether was used in the proportion 1:1 or more with the isobutane or with a mixture of isobuane and propane.
  • the yield of the foam is lower due to the low content of free monomers containing NCO groups and limited production of CO2 which was compensated by the addition of blowing agents.
  • the content of gases of 25% and more by weight is also beneficial for the yield of the final foam.
  • a critical factor is low NCO:OH ratio of 1 to 2,5 preferably 1,2 to 2,3, more preferably 1,4 to 2,2. It is extremely important to have a low NCO:OH ratio to obtain a monomeric content below 3%, preferably below 2%, more preferably below 1%.
  • Table 2 Maximum temperature after some period of time m the mixture prepared by mixing ingredients with isocyanate (Lupranat M20) with NCO: OH ratio 1. Polyol was mixed with MDI in the proportion of NC0:0H ratio 1 at a room temperature for 15 seconds. Then, a cup with mixed ingredients was introduced immediately into an insulated container with thermal probe placed approximately 2 cm from the bottom of the cup. Time and temperature were recorded during reaction. Results of maximum temperature and time are shown in the table 2.

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

Abstract

La présente invention concerne un mélange de prépolymère isocyanate à un constituant destiné à produire le produit polyuréthane dans un procédé en une étape, ledit mélange ayant une teneur en monomère libre diisocyanate de diphénylméthane (MDI) inférieure à 3 %, de préférence inférieure à 2 %, de préférence encore inférieure à 1 % du poids total comprenant un alcool monofonctionnel, un constituant isocyanate ou un mélange d'agent propulseur à base de constituant isocyanate, un catalyseur, un agent stabilisant, un ou plusieurs polyols, caractérisé en ce que l'alcool monofonctionnel a une masse molaire faible, Mw étant inférieure à 130 g/mol, est de préférence un alcool tertiaire, de préférence encore le tert-butanol, le 2-métyl 2-butanol, le n-butanol, l'isobutanol ou leurs mélanges et un procédé pour le préparer.
PCT/PL2013/050002 2013-02-06 2013-02-06 Mélange de prépolymère isocyanate à un constituant pour la production du produit polyuréthane dans un procédé en une étape WO2014123434A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/PL2013/050002 WO2014123434A1 (fr) 2013-02-06 2013-02-06 Mélange de prépolymère isocyanate à un constituant pour la production du produit polyuréthane dans un procédé en une étape

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/PL2013/050002 WO2014123434A1 (fr) 2013-02-06 2013-02-06 Mélange de prépolymère isocyanate à un constituant pour la production du produit polyuréthane dans un procédé en une étape

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106317377A (zh) * 2016-08-30 2017-01-11 福州联泓交通器材有限公司 一种汽车内饰用的低voc发泡绵及其制备方法
US9738747B2 (en) 2014-01-14 2017-08-22 Selena Labs Sp. Z O.O. One component isocyanate prepolymer mixture for polyurethane product formulation in a single step process
US10730996B2 (en) 2015-09-29 2020-08-04 Dow Global Technologies Llc Toluene diisocyanate biuret based prepolymers for polyurethane foams
US11845886B2 (en) 2019-06-25 2023-12-19 H.B. Fuller Company Moisture curable polyurethane hot melt adhesive composition having low levels of diisocyanate monomer

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4623709A (en) 1984-01-14 1986-11-18 Henkel Kommanditgesellschaft Auf Aktien Adhesives based on polyurethane prepolymers having a low residual monomer content
US5441808A (en) 1990-03-30 1995-08-15 H.B. Fuller Fuller Licensing & Financing Inc. Thermally stable hot melt moisture-cure polyurethane adhesive composition
US5880167A (en) * 1994-08-22 1999-03-09 Henkel Kommanditgesellschaft Auf Aktien Polyurethane compositions with a low content of monomeric diisocyanates
WO2002090410A2 (fr) * 2001-03-20 2002-11-14 Baxenden Chemicals Limited Mousse a un composant
US6515164B1 (en) 1997-01-02 2003-02-04 Henkel Kommanditgesellschaft Auf Aktien Low monomer polyurethane prepolymer and process therefore
US6552097B1 (en) * 1993-02-10 2003-04-22 Rathor Ag Prepolymer compositions for insulating foams
DE10311607A1 (de) * 2003-03-14 2004-09-23 Basf Ag 1-Komponenten-Polyurethan-Montageschaum
EP1518874A1 (fr) * 2003-09-24 2005-03-30 Basf Aktiengesellschaft MDI polymere contenant un faible teneur en monomeres
EP2481764A1 (fr) 2011-01-27 2012-08-01 de Schrijver, Aster Composition pour mousses de polyuréthane à un seul composant dotée d'un contenu à faible teneur en MDI monomérique

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4623709A (en) 1984-01-14 1986-11-18 Henkel Kommanditgesellschaft Auf Aktien Adhesives based on polyurethane prepolymers having a low residual monomer content
US5441808A (en) 1990-03-30 1995-08-15 H.B. Fuller Fuller Licensing & Financing Inc. Thermally stable hot melt moisture-cure polyurethane adhesive composition
US6552097B1 (en) * 1993-02-10 2003-04-22 Rathor Ag Prepolymer compositions for insulating foams
US5880167A (en) * 1994-08-22 1999-03-09 Henkel Kommanditgesellschaft Auf Aktien Polyurethane compositions with a low content of monomeric diisocyanates
US6515164B1 (en) 1997-01-02 2003-02-04 Henkel Kommanditgesellschaft Auf Aktien Low monomer polyurethane prepolymer and process therefore
WO2002090410A2 (fr) * 2001-03-20 2002-11-14 Baxenden Chemicals Limited Mousse a un composant
DE10311607A1 (de) * 2003-03-14 2004-09-23 Basf Ag 1-Komponenten-Polyurethan-Montageschaum
EP1518874A1 (fr) * 2003-09-24 2005-03-30 Basf Aktiengesellschaft MDI polymere contenant un faible teneur en monomeres
EP2481764A1 (fr) 2011-01-27 2012-08-01 de Schrijver, Aster Composition pour mousses de polyuréthane à un seul composant dotée d'un contenu à faible teneur en MDI monomérique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MIHAIL IONESCU: "Chemistry and Technology of Polyols for Polyurethane", 2005, ROPRA TECHNOLOGY LTD., pages: 18

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9738747B2 (en) 2014-01-14 2017-08-22 Selena Labs Sp. Z O.O. One component isocyanate prepolymer mixture for polyurethane product formulation in a single step process
US10730996B2 (en) 2015-09-29 2020-08-04 Dow Global Technologies Llc Toluene diisocyanate biuret based prepolymers for polyurethane foams
CN106317377A (zh) * 2016-08-30 2017-01-11 福州联泓交通器材有限公司 一种汽车内饰用的低voc发泡绵及其制备方法
US11845886B2 (en) 2019-06-25 2023-12-19 H.B. Fuller Company Moisture curable polyurethane hot melt adhesive composition having low levels of diisocyanate monomer

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