WO2007104623A1 - Composition made from a diisocyanate and a monoamine and process for preparing it - Google Patents

Composition made from a diisocyanate and a monoamine and process for preparing it Download PDF

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Publication number
WO2007104623A1
WO2007104623A1 PCT/EP2007/051335 EP2007051335W WO2007104623A1 WO 2007104623 A1 WO2007104623 A1 WO 2007104623A1 EP 2007051335 W EP2007051335 W EP 2007051335W WO 2007104623 A1 WO2007104623 A1 WO 2007104623A1
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WO
WIPO (PCT)
Prior art keywords
weight
composition according
polyisocyanate
water
polyol
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2007/051335
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English (en)
French (fr)
Inventor
Gerhard Jozef Bleys
Hans Godelieve Guido Verbeke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman International LLC
Original Assignee
Huntsman International LLC
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 Huntsman International LLC filed Critical Huntsman International LLC
Priority to CA002640381A priority Critical patent/CA2640381A1/en
Priority to DE602007001876T priority patent/DE602007001876D1/de
Priority to JP2008558751A priority patent/JP2009529597A/ja
Priority to AT07704514T priority patent/ATE438671T1/de
Priority to US12/282,540 priority patent/US8143364B2/en
Priority to CN2007800088754A priority patent/CN101400713B/zh
Priority to BRPI0708263-0A priority patent/BRPI0708263A2/pt
Priority to EP07704514A priority patent/EP1996634B1/en
Priority to AU2007224541A priority patent/AU2007224541B2/en
Publication of WO2007104623A1 publication Critical patent/WO2007104623A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • 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
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
    • 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
    • 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
    • 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
    • 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
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Definitions

  • the present invention is related to a novel composition made from a diisocyanate and a monoamine and to a process for making such composition.
  • US 2005/049358 discloses the preparation of reaction products of a polyisocyanate and a polyether amine for use as water dispersible compositions. These compositions are subsequently added to water.
  • WO 95/23819 proposes the use of certain polyols and mono functional additives like monoamines in making water-blown flexible foams to provide a positive effect on cell opening, amongst others.
  • novel composition has been found and a process for preparing it.
  • the novel composition has valuable properties which make it very useful as rheology modifying agent and in particular as cell opener in processes wherein cell opening is desired, especially in making polyurethane foams.
  • the present invention is concerned with a composition comprising a mixture of compounds of the formula:
  • Ri is a monoalkoxy polyoxyalkylene monovalent radical having an average molecular weight of 500-5000;
  • R2 is a hydrocarbon divalent radical having an average molecular weight of 28-500; n is at least 1 and the average of n is more than 1 ; and wherein the mixture is present in the composition in an amount of at least 80 and preferably at least 90 mol %.
  • composition prepared according to the process of the present invention revealed that it may contain a small amount of other material resulting from side reactions. This amount is less than 20 mol % and preferably less than 10 mol %.
  • the present invention is related to the use of such a composition as rheology modifying agent and preferably as cell opening agent.
  • the present invention is related to a process for making a polyurethane foam which process comprises reacting a polyisocyanate and an isocyanate -reactive compound and using a blowing agent and a composition according to the present invention and to foams made by this process.
  • average nominal hydroxyl functionality (or in short “functionality) is used herein to indicate the number average functionality (number of hydroxyl goups per molecule) of a polyol or a polyol composition on the assumption that this is the number average functionality (number of active hydrogen atoms per molecule) of the initiator(s) used in their preparation although in practice it will often be somewhat less because of some terminal unsaturation and other side reactions during production.
  • the ingredients used for making the composition according to the present invention may be combined and mixed in any order at ambient conditions.
  • the monoamine and the water are premixed.
  • the reaction is allowed to proceed under ambient conditions. Since the reaction is exothermic in general no further heating is required. 10-500 minutes after the combining of the 3 ingredients the reaction will be complete in general and the composition according to the invention is allowed to cool.
  • the composition obtained is usually a dispersion which is useful as cell opener in making cellular products, in particular polyurethane foams.
  • the use of a small amount of an ionic inorganic salt and in particular of a metal halide and more in particular of LiCl in the process to make the composition according to the present invention gives a composition according to the invention with reduced turbidity.
  • the ionic inorganic salt is preferably added via the water.
  • the amount used preferably is 5-100 % by weight calculated on the amount of water used.
  • the hydrocarbon compound containing 2 isocyanate groups may be selected from aliphatic, cycloaliphatic, araliphatic and aromatic ones such as hexamethylene, isophorone, dicyclohexylmethane, naphthalene, tetramethylxylene, phenylene, cyclohexane, toluene and diphenylmethane.
  • the diisocyanate is an aromatic diisocyanate and most preferably diphenylmethane diisocyanate (MDI).
  • the monoamine is a monoalkoxy polyoxyalkylene monoamine having an average molecular weight 500-5000 without the amine group.
  • the monoalkoxy group preferably has 1-20 and more preferably 1-6 and most preferably 1 carbon atom.
  • the polyoxyalkylene group may consist of one or more types of oxyalkylene groups, like oxyethylene, oxypropylene and/or oxybutylene.
  • the polyoxyalkylene radical is a polyoxyethylene polyoxypropylene radical, especially those having an oxyethylene content of 60-90 % by weight.
  • Such monoamines are commercially available; examples are Jeffamine M2005, ex Huntsman, which is a monoamine comprising a high amount of oxypropylene groups, and JeffamineTM MlOOO and M2070, ex Huntsman, which are monoamines comprising a high amount of oxyethylene groups.
  • the composition can be used as a cell opening agent. It was further found that when the composition according to the present invention was centrifuged, the precipitate and the supernatant both showed cell opening properties as well.
  • the precipitate as well as the supernatant are compositions according to the present invention. Such centrifuging process may conveniently be conducted at ambient conditions at a centrifuge speed of 1000 to 10.000 rounds per minute for 10 to 1000 minutes. The supernatant and precipitate are subsequently separated by simply decanting the supernatant.
  • polyisocyanates are reacted with isocyanate -reactive ingredients like polyols and polyamines using blowing agents, like hydrocarbons, e.g. pentane and cyclopentane; chlorofluorohydrocarbons; inert gasses, e.g. N 2 , CO2 or air; and/or water and using a composition according to the present invention and optionally using additives known in the art like chain extenders, cross-linkers, surfactants, catalysts, plasticizers, flame retardants, internal mould release agents, colorants and antimicrobial agents.
  • blowing agents like hydrocarbons, e.g. pentane and cyclopentane; chlorofluorohydrocarbons; inert gasses, e.g. N 2 , CO2 or air; and/or water
  • additives known in the art like chain extenders, cross-linkers, surfactants, catalysts, plasticizers, flame retardants, internal mould release agents, colorants and antimicrobial agents.
  • the process may be conducted according to the one shot process or the prepolymer process.
  • part or all of the polyols and polyamines may be pre -reacted with the polyisocyanate so as to obtain an isocyanate terminated prepolymer which subsequently is used to make the foam by reaction of this prepolymer with water which then acts as isocyanate -reactive compound and as - chemical - blowing agent at the same time (water reacts with isocyanate groups to give urea groups and CO2 which is responsible for the blowing).
  • the process is a process for preparing a flexible polyurethane foam and more in particular a hydrophilic flexible polyurethane foam which is made by reacting a polyisocyanate and a polyether polyol comprising at least 40 % by weight of oxyethylene groups calculated on the weight of the polyol and using water as blowing agent in an amount of 0.5-50 parts by weight (pbw) per 100 parts by weight of polyisocyanate and polyol used to make the foam.
  • pbw parts by weight
  • the polyisocyanate, the polyol and the water may be combined and allowed to react in the presence of the cell opener; alternatively the polyisocyanate and the polyol may be prereacted into a so-called prepolymer and subsequently this prepolymer may be reacted with the water in the presence of the cell opener.
  • the cell opener may be added in any way. Preferably it is added to the polyisocyanate or to the water before it is used.
  • the amount of cell opener needed in general is rather small; it may vary between 0.0001-2 and preferably between 0.0001-1 % by weight calculated on the amount of polyisocyanate and polyol used to make the foam.
  • the process is selected from 1) a process for making a hydrophylic polyurethane foam wherein an isocyanate -terminated prepolymer, 4.5-14.5 parts by weight of water (per 100 parts by weight of prepolymer) and 0.0001-1 parts by weight of a composition according to the invention (per 100 parts by weight of prepolymer) are used, wherein the prepolymer has an NCO-value of 3-15 % by weight and has been made by reacting diphenylmethane diisocyanate comprising at least 40 % by weight of 4,4 '-diphenylmethane diisocyanate and an amine-free polyoxy ethylene polyoxypropylene polyol having a nominal hydroxyl functionality of 2-4 and having an oxyethylene content of 40-90 % by weight calculated on the weight of the polyol and an average molecular weight of 3000-6000 (surprisingly it was found that foams obtained according to this process had good properties and open cell structure and could be made without using any catalyst) and 2) a
  • the present invention is related to a mixture comprising a polyisocyanate and a composition according to the present invention; preferably the mixture comprises 0.0001-25 and more preferably 0.0002-6 pbw of composition according to the present invention per 100 pbw of polyisocyanate.
  • the polyisocyanate preferably is an aromatic one; more preferably one comprising MDI as described hereinbefore.
  • the resulting product was a dispersion; the dispersed phase consisted of small particles which were visible by means of an optical microscope.
  • the product was further characterized via C-NMR (using dimethylsulphoxide as solvent and a magnetic field frequency of 400 MHz).
  • the ratio of the integrals of the peaks of the urea groups formed by the amine, to those formed by the water and to a side- reaction impurity was about 215 : 100 : 9.
  • Example 2 The product obtained in example 1 was subjected to centrifugation (Heraeus Sepatech Megofuge 1.0) for 3 hours at 4300 rounds per minute (r.p.m.). The supernatant and the pellet obtained after decanting the supernatant were subjected to the same NMR characterization as example 1; the ratio of the peak integrals of the urea groups formed by the amine to those formed by the water was 13 : 1 for the supernatant and 0.22 : 1 for the precipitate.
  • centrifugation Heraeus Sepatech Megofuge 1.0
  • the supernatant and the pellet obtained after decanting the supernatant were subjected to the same NMR characterization as example 1; the ratio of the peak integrals of the urea groups formed by the amine to those formed by the water was 13 : 1 for the supernatant and 0.22 : 1 for the precipitate.
  • Examples 1 and 2 were repeated with 8412.9 g of Jeffamine M2070, 66.65 g of water and 1520.4 g of Suprasec 1306.
  • the ratio of the integral of the peaks was 100 : 101 : 7 (dispersion); 5.3 : 1 (supernatant) and 0.22 : 1 (pellet).
  • the dispersion contained at least 96.5 mol % of the formula compound wherein Ri and R2 had the same meaning as in example 1 and n is about 3 on average and at most 3.5 mol % of other compounds resulting from side reactions.
  • Example 3 was repeated with an MDI comprising 50 % by weight of 2,4'-MDI, Jeffamine M2070, water and LiCl in an amount of 40 % by weight calculated on the amount of water (the LiCl was dissolved in the water). A clear liquid was obtained.
  • Example 5
  • Example 1 was repeated with Suprasec 1306, Jeffamine M2005 and water.
  • the product was a gel.
  • LiCl was used as in example 4 a stable dispersion was obtained.
  • Suprasec 1002 100 pbw of Suprasec 1002, an isocyanate - terminated prepolymer ex Huntsman, was thoroughly mixed with 5 pbw of water using a conventional bench mixer. The foaming composition was allowed to rise freely.
  • the resulting foam had extremely closed cells; it was not possible to crush the foam in a usual way.
  • Example 1 was repeated using a molar ratio of Suprasec 1306 to dried Jeffamine M2070 of 1 : 2 and no water. A clear liquid was obtained.
  • Example 6 was repeated with 5 %w of the product of example 7 in the water (calculated on the water).
  • the foam had extremely closed cells and could not be crushed in a usual way.
  • Example 6 was repeated but with 5 %w of the product of example 1 in the water (calculated on the water). The foam had open cells and the foam did not shrink.
  • Example 6 was repeated but with 2.5 %w of the product of example 1 in the water (calculated on the water). The foam had open cells and the foam did not shrink. A similar result was obtained when the supernatant and the precipitate of example 2 were used.
  • Example 11 comparative
  • Example 6 was repeated with 5 %w of Jeffamine M 2070 in the water (calculated on the water).
  • the foam obtained was closed and not crushable in a usual way.
  • Example 11 was repeated with 5 %w of Jeffamine M 2070 (calculated on the polyisocyanate). The foam obtained was closed and uncrushable in a usual way.
  • Suprasec 1002 mixed with the product of example 1 wherein the amount of product of example 1 is 0.0025, 0.025 and 0.25 pbw respectively (on 100 pbw of Suprasec 1002) with a standard lab mixer at room temperature gives a stable (at least 24h at room temperature) mixture.
  • a polyisocyanate consisting of 50 % by weight of Suprasec 2020 and 50 % by weight of
  • the foam obtained had a core density of 61 kg/m 3 and had open cells. When the cell opener was not used the foams had more closed cells and could not be easily crushed.
  • Daltocel F555 is a polyether polyol having an oxyethylene content of about 75 % by weight, ex Huntsman.
  • Jeffcat ZR50 is an amine catalyst, ex Huntsman.
  • Daltocel 526 is a polyoxyethylene polyol, ex Huntsman.
  • Suprasec 2020 is a uretonimine modified MDI ex Huntsman (Suprasec, Daltocel and

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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)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/EP2007/051335 2006-03-14 2007-02-12 Composition made from a diisocyanate and a monoamine and process for preparing it Ceased WO2007104623A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CA002640381A CA2640381A1 (en) 2006-03-14 2007-02-12 Composition made from a diisocyanate and a monoamine and process for preparing it
DE602007001876T DE602007001876D1 (de) 2006-03-14 2007-02-12 Zusammensetzung aus einem diisocyanat und einem monoamin und herstellungsverfahren dafür
JP2008558751A JP2009529597A (ja) 2006-03-14 2007-02-12 ジイソシアネートとモノアミンから製造される組成物およびその製造方法
AT07704514T ATE438671T1 (de) 2006-03-14 2007-02-12 Zusammensetzung aus einem diisocyanat und einem monoamin und herstellungsverfahren dafür
US12/282,540 US8143364B2 (en) 2006-03-14 2007-02-12 Composition made from a diisocyanate and a monoamine and process for preparing it
CN2007800088754A CN101400713B (zh) 2006-03-14 2007-02-12 由二异氰酸酯和单胺制成的组合物及其制备方法
BRPI0708263-0A BRPI0708263A2 (pt) 2006-03-14 2007-02-12 composição, processos para a preparação de uma composição e para a produção de uma espuma de poliuretano, espuma, mistura, e, uso de uma composição
EP07704514A EP1996634B1 (en) 2006-03-14 2007-02-12 Composition made from a diisocyanate and a monoamine and process for preparing it
AU2007224541A AU2007224541B2 (en) 2006-03-14 2007-02-12 Composition made from a diisocyanate and a monoamine and process for preparing it

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06111114.2 2006-03-14
EP06111114 2006-03-14

Publications (1)

Publication Number Publication Date
WO2007104623A1 true WO2007104623A1 (en) 2007-09-20

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ID=36940234

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/051335 Ceased WO2007104623A1 (en) 2006-03-14 2007-02-12 Composition made from a diisocyanate and a monoamine and process for preparing it

Country Status (13)

Country Link
US (1) US8143364B2 (enExample)
EP (1) EP1996634B1 (enExample)
JP (1) JP2009529597A (enExample)
KR (1) KR20080112293A (enExample)
CN (1) CN101400713B (enExample)
AT (1) ATE438671T1 (enExample)
AU (1) AU2007224541B2 (enExample)
BR (1) BRPI0708263A2 (enExample)
CA (1) CA2640381A1 (enExample)
DE (1) DE602007001876D1 (enExample)
ES (1) ES2327583T3 (enExample)
RU (1) RU2441034C2 (enExample)
WO (1) WO2007104623A1 (enExample)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2072549A1 (en) 2007-12-19 2009-06-24 Huntsman International Llc Novel composition from a polyisocyanate and a polyether monoamine
US8519062B2 (en) 2008-02-14 2013-08-27 Huntsman International Llc Elastomeric materials having a high hardblock content and process for preparing them
EP3486292A4 (en) * 2016-07-15 2020-03-25 Kansai Paint Co., Ltd COATING COMPOSITION
US12091580B2 (en) 2019-02-15 2024-09-17 Kansai Paint Co., Ltd. Paint composition
US12240997B2 (en) 2019-02-15 2025-03-04 Kansai Paint Co., Ltd. Rheology control agent and paint composition
US12378423B2 (en) 2019-03-26 2025-08-05 Kansai Paint Co., Ltd. Paint composition

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2421906T3 (pl) * 2009-04-21 2017-08-31 Huntsman International Llc Kompozycja poliizocyjanianowa
US9926479B2 (en) * 2009-06-09 2018-03-27 Huntsman International Llc Materials comprising a matrix and process for preparing them
EP2552988B1 (en) * 2010-03-31 2015-03-11 Dow Global Technologies LLC One component polyurethane foam formulation with non-liquefied inert propellant
JP5972005B2 (ja) * 2012-03-28 2016-08-17 株式会社ネオス 水溶性消泡剤および低泡性加工油剤
EP3643731B1 (en) * 2017-06-20 2024-05-15 Archem Inc. Composition for soft polyurethane foam, soft polyurethane foam, and vehicle seat pad
MX2021010983A (es) * 2019-03-12 2021-10-13 Huntsman Petrochemical Llc Dispersantes elaborados a partir de isocianatos y aminas.
CN114349932B (zh) * 2022-01-17 2024-05-31 亚士创能科技(上海)股份有限公司 可用于颜料包覆的聚合物、聚合物包覆颜料及其制备方法和无机涂料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4261845A (en) * 1980-01-18 1981-04-14 Texaco Development Corporation Novel polyureas and their use as grease thickening agents
JPH07258374A (ja) * 1994-03-22 1995-10-09 Nippon Polyurethane Ind Co Ltd 軟質ウレタンフォームの製造方法
US20040054117A1 (en) * 2001-03-12 2004-03-18 Christian Wamprecht New polyurethanes and their use for the thickening of aqueous systems
US20050049358A1 (en) * 2003-08-27 2005-03-03 Great Eastern Resins Industrial Co., Ltd. Water dispersible polyisocyanate composition bearing urea and/or biuret and its uses

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL209758A (enExample) 1955-08-12
US2925387A (en) 1958-07-21 1960-02-16 Standard Oil Co Method of preparing ureido grease-thickener concentrate and lubricating greases containing same
GB956056A (en) * 1961-10-02 1964-04-22 Ici Ltd Improvements in or relating to the manufacture of foamed polyurethanes
GB1169737A (en) 1966-04-29 1969-11-05 Internat Synthetic Rubber Comp Thermoplastic Elastomer Block Polymers
US3401027A (en) 1967-04-10 1968-09-10 Chevron Res Light hydrocarbon liquids containing a jellifying agent comprising polyureas
GB1250401A (enExample) 1968-01-08 1971-10-20
US3741911A (en) 1970-12-21 1973-06-26 Hart Chemical Ltd Phosphate-free detergent composition
DE2418075A1 (de) 1974-04-13 1975-10-30 Bayer Ag Thermoplastische polyurethan-elastomere mit verbesserter verarbeitbarkeit
NL176864C (nl) * 1976-11-25 1985-06-17 Akzo Nv Werkwijze voor de bereiding van een thixotrope bekledingssamenstelling.
DE2738268A1 (de) 1977-08-25 1979-03-08 Basf Ag Hydrophobe polyurethanschaumstoffe zur oelabsorption
DE2902469A1 (de) * 1979-01-23 1980-07-31 Bayer Ag Suspensionen von isocyanatoharnstoffen in isocyanatpraepolymeren, ein verfahren zu ihrer herstellung, sowie ihre verwendung bei der herstellung von hochmolekularen polyurethankunststoffen
DE3021293A1 (de) 1980-06-06 1981-12-24 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von elastischen polyurethanschaumstoffen
DE3132760A1 (de) 1981-08-19 1983-03-03 Basf Ag, 6700 Ludwigshafen Verfahren zur verbesserung der fliessfaehigkeit von polyurethan-elastomeren
DE3303442A1 (de) 1983-02-02 1984-08-16 Optimol-Ölwerke GmbH, 8000 München Schmierfettzusammensetzung, ihre herstellung und verwendung
US4499254A (en) 1984-02-13 1985-02-12 Texaco Inc. Reaction injection molded elastomers containing high molecular weight organic acids
US4751253A (en) 1986-10-06 1988-06-14 Tylenda Eugene J Method of preparing dimensionally stable, flexible urethane foam and the foam produced thereby
US4791146A (en) 1986-10-06 1988-12-13 Tylenda Eugene J Method of preparing dimensionally stable, flexible urethane foam and the foam produced thereby
GB8701993D0 (en) 1987-01-29 1987-03-04 Bp Chem Int Ltd Polyurethane foams
DE3724555A1 (de) 1987-07-24 1989-02-02 Basf Ag Viskositaetsregulierende stoffe fuer einkomponentige polyurethansysteme
US5145591A (en) 1989-07-07 1992-09-08 Nippon Oil Co., Ltd. Diurea grease composition
US5364909A (en) 1992-07-23 1994-11-15 Arco Chemical Technology, L.P. Graft polymer compositions containing mono-amine functionalized polyoxyalkylene ethers
DE4236901A1 (de) * 1992-10-31 1994-05-05 Herberts Gmbh Als Rheologie-Beeinflusser geeignete Zusammensetzung, Verfahren zu deren Herstellung und deren Verwendung in Überzugsmitteln
GB9311838D0 (en) 1993-06-08 1993-07-28 Ici Plc Process for making flexible foams
GB9404127D0 (en) 1994-03-03 1994-04-20 Polyol Int Bv Process for producing a soft, flexible, hot molded poyurethane foam
JP3500700B2 (ja) 1994-05-31 2004-02-23 旭硝子株式会社 非フォーム状ポリウレタン樹脂の製造方法
US5591779A (en) 1994-11-22 1997-01-07 Imperial Chemical Industries Plc Process for making flexible foams
AU7917298A (en) 1997-07-09 1999-02-08 Huntsman Ici Chemicals Llc Compressed hydrophilic polyurethane foams
US6355721B1 (en) 1999-12-03 2002-03-12 Bayer Coporation High molecular weight liquid, non-functional polyether polyurethane plasticizers
US6218462B1 (en) 1999-12-03 2001-04-17 Bayer Corporation Liquid ultra-high molecular weight polyurethane plasticizers
AU5626801A (en) * 2000-04-12 2001-10-23 Akzo Nobel Nv Aqueous two-component cross-linkable composition
DE10126647A1 (de) 2001-06-01 2002-12-12 Basf Coatings Ag Rheologiehilfsmittel, Verfahren zu seiner Herstellung und seine Verwendung
WO2004014980A1 (en) 2002-08-02 2004-02-19 Huntsman International Llc Polyols
US20050131095A1 (en) 2002-08-02 2005-06-16 Jianming Yu Novel polyols
DE10241853B3 (de) * 2002-09-09 2004-01-22 Byk-Chemie Gmbh Polymeres Harnstoffurethan als Rheologiesteuerungsmittel und Verfahren zur Herstellung
US20070148471A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Impact resistant polyurethane and poly(ureaurethane) articles and methods of making the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4261845A (en) * 1980-01-18 1981-04-14 Texaco Development Corporation Novel polyureas and their use as grease thickening agents
JPH07258374A (ja) * 1994-03-22 1995-10-09 Nippon Polyurethane Ind Co Ltd 軟質ウレタンフォームの製造方法
US20040054117A1 (en) * 2001-03-12 2004-03-18 Christian Wamprecht New polyurethanes and their use for the thickening of aqueous systems
US20050049358A1 (en) * 2003-08-27 2005-03-03 Great Eastern Resins Industrial Co., Ltd. Water dispersible polyisocyanate composition bearing urea and/or biuret and its uses

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 02 29 February 1996 (1996-02-29) *

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2072549A1 (en) 2007-12-19 2009-06-24 Huntsman International Llc Novel composition from a polyisocyanate and a polyether monoamine
WO2009080465A1 (en) * 2007-12-19 2009-07-02 Huntsman International Llc Novel composition from a polyisocyanate and a polyether monoamine
US8283421B2 (en) 2007-12-19 2012-10-09 Huntsman International Llc Composition from a polyisocyanate and a polyether monoamine
CN101903431B (zh) * 2007-12-19 2012-12-12 亨茨曼国际有限公司 多异氰酸酯和聚醚单胺的组合物
RU2484101C2 (ru) * 2007-12-19 2013-06-10 Хантсмэн Интернэшнл Ллс Новая композиция из полиизоцианата и полиэфирного моноамина
US8519062B2 (en) 2008-02-14 2013-08-27 Huntsman International Llc Elastomeric materials having a high hardblock content and process for preparing them
CN101945910B (zh) * 2008-02-14 2013-09-18 亨茨曼国际有限公司 具有高的硬嵌段含量的弹性体材料和制备它们的方法
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US11292936B2 (en) 2016-07-15 2022-04-05 Kansai Paint Co., Ltd. Coating composition
US12091580B2 (en) 2019-02-15 2024-09-17 Kansai Paint Co., Ltd. Paint composition
US12240997B2 (en) 2019-02-15 2025-03-04 Kansai Paint Co., Ltd. Rheology control agent and paint composition
US12378423B2 (en) 2019-03-26 2025-08-05 Kansai Paint Co., Ltd. Paint composition

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EP1996634A1 (en) 2008-12-03
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ATE438671T1 (de) 2009-08-15
US8143364B2 (en) 2012-03-27
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