EP0365599A4 - Polyisocyanate prepolymers prepared from rigid polyaromatic precursor materials, and polyurethanes prepared therefrom - Google Patents

Polyisocyanate prepolymers prepared from rigid polyaromatic precursor materials, and polyurethanes prepared therefrom

Info

Publication number
EP0365599A4
EP0365599A4 EP19880906734 EP88906734A EP0365599A4 EP 0365599 A4 EP0365599 A4 EP 0365599A4 EP 19880906734 EP19880906734 EP 19880906734 EP 88906734 A EP88906734 A EP 88906734A EP 0365599 A4 EP0365599 A4 EP 0365599A4
Authority
EP
European Patent Office
Prior art keywords
polyisocyanate
active hydrogen
polyaromatic
rigid
containing compound
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
EP19880906734
Other languages
English (en)
Other versions
EP0365599A1 (fr
Inventor
Oomman P. Thomas
Earl E. Burt, Iii
Richard D. Peffley
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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 Dow Chemical Co filed Critical Dow Chemical Co
Publication of EP0365599A1 publication Critical patent/EP0365599A1/fr
Publication of EP0365599A4 publication Critical patent/EP0365599A4/en
Ceased legal-status Critical Current

Links

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
    • C08G18/28—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
    • 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
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8191—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with acetylenic compounds having 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
    • 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
    • C08G18/80—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
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • 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
    • C08G18/80—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
    • C08G18/8038—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3225
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8054—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38
    • C08G18/8058—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38 with compounds of C08G18/3819
    • 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
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen

Definitions

  • polymers having widely varying properties can be prepared.
  • polymers having widely varying properties can be prepared.
  • rigid polyurethanes are prepared.
  • a prepolymer composition of this invention to prepare a polyurethane or polyurea provides substantially improved physical properties, particularly load-bearing and/or tensile properties in flexible polyurethane foam.
  • rigid precursor compounds examples include adducts of bisphenol with from 2 to 10 moles of pyropylene oxide and/or ethylene oxide, adducts of 3,5,3',5'-tetraraethylbiphenol with from 2 to 10 moles of propylene oxide and/or ethylene oxide and adducts of 3,5,3',5'-tetrahalobiphenol with from 2 to 10 moles of propylene oxide and/or ethylene oxide.
  • the rigid precursor compound can be reacted with a polyisocyanate to form an isocyanate-terminated prepolymer containing an internal rigid moiety.
  • This is advantageously accomplished by combining a stoichiometric excess of the polyisocyanate with the rigid precursor compound.
  • Advantageously from 1 to 50, preferrably from 5 to 40, more preferably from 5 to 25 parts by weight of the rigid precursor compound are combined with 100 parts by weight of the polyisocyanate and caused to react until all of the active hydrogen- containing groups in the rigid precursor compound have reacted.
  • the resulting prepolymer product is a solution or colloidal dispersion of the prepolymer in the polyisocyanate.
  • it is preferred to use a substantially difunctional polyisocyanate, although higher functionality polyisocyanates may also be used.
  • Crosslinkers which are commonly employed in preparing flexible polyurethane foams include, for example, low equivalent weight alkanolamines such as ethanolamine, diethanolamine, triethanolamine, propanolamine, dipropanolamine, tripropanolamine, methyldiethanol amine and methyl dripopanol amine. Also useful are the alkylene glycols and low equivalent weight hydroxyl-terminated polyols such as glycerine and trimethylol propane. Such crosslinkers are generally used in minor amounts, preferably from 0.2 to 10, more preferably from 0.5 to 5 parts per 100 parts of relatively high equivalent weight active hydrogen- containing compounds.
  • a TDI prepolymer was prepared by adding to 100 parts TDI 10 parts of a rigid monomer having the structure
  • the resulting foam Sample No. 1 a contained 3.27 weight percent of the rigid monomer and had properties as indicated in Table 2 following.
  • Example 1 by reacting 100 parts by weight TDI with 10 parts of rigid monomers represented by the structures:
  • the prepolymer was used to prepare a polyurethane foam according to the procedure described in Example 1.
  • the foam had properties as indicated in Table 4 following.
  • a foam was prepared using unmodified TDI as the polyisocyante (Comparative Sample C). Its properties are indicated in Table 4. Substantial improvement in load bearing and tensile strength are seen with this invention.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
EP19880906734 1987-07-14 1988-07-07 Polyisocyanate prepolymers prepared from rigid polyaromatic precursor materials, and polyurethanes prepared therefrom Ceased EP0365599A4 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7304687A 1987-07-14 1987-07-14
US73046 1987-07-14

Publications (2)

Publication Number Publication Date
EP0365599A1 EP0365599A1 (fr) 1990-05-02
EP0365599A4 true EP0365599A4 (en) 1990-09-12

Family

ID=22111386

Family Applications (2)

Application Number Title Priority Date Filing Date
EP19880906734 Ceased EP0365599A4 (en) 1987-07-14 1988-07-07 Polyisocyanate prepolymers prepared from rigid polyaromatic precursor materials, and polyurethanes prepared therefrom
EP88111235A Withdrawn EP0299462A3 (fr) 1987-07-14 1988-07-13 Prépolymères de polyisocyanate préparés à partir de matériaux-précurseurs rigides polyaromatiques et polyuréthanes préparés à partir de ceux-ci

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP88111235A Withdrawn EP0299462A3 (fr) 1987-07-14 1988-07-13 Prépolymères de polyisocyanate préparés à partir de matériaux-précurseurs rigides polyaromatiques et polyuréthanes préparés à partir de ceux-ci

Country Status (6)

Country Link
EP (2) EP0365599A4 (fr)
JP (1) JPH02502384A (fr)
KR (1) KR890701657A (fr)
AU (1) AU606737B2 (fr)
BR (1) BR8807617A (fr)
WO (1) WO1989000588A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX163878B (es) * 1988-11-16 1992-06-29 Mobay Corp Procedimiento para la preparacion de prepolimeros de isocianato,liquidos,estables en almacenamiento
JP6138523B2 (ja) * 2013-03-07 2017-05-31 東洋ゴム工業株式会社 液晶ポリウレタンエラストマー及びその製造方法
JP6407580B2 (ja) * 2014-06-20 2018-10-17 旭化成株式会社 エポキシ樹脂及びその組成物、並びに化合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3078257A (en) * 1957-07-06 1963-02-19 Bayer Ag Polyurethane bristles and process for their manufacture
US3330781A (en) * 1962-05-07 1967-07-11 Mobay Chemical Corp Polyurethane plastics prepared from alkylene oxide adducts of compositions comprising a major portion of trihydroxydiphenyl
US4071484A (en) * 1973-10-23 1978-01-31 Kohkoku Chemical Industry Co., Ltd. Process for preparing flexible flame retarding polyurethane foams
GB2100276A (en) * 1981-06-11 1982-12-22 Goldschmidt Ag Th Curable adhesive

Family Cites Families (26)

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Publication number Priority date Publication date Assignee Title
US3925296A (en) * 1971-10-26 1975-12-09 Hooker Chemicals Plastics Corp Foundry aggregate binders
US3795636A (en) * 1972-01-12 1974-03-05 Quaker Oats Co Process for the preparation of polyurethane foams and microcellular elastomers with integral skins and polyol extender system for the preparation thereof
SU523643A3 (ru) * 1973-03-09 1976-07-30 Байер Аг, (Фирма) Способ получени полиуретанмочевины в высокодисперсном виде
JPS5216596A (en) * 1975-07-31 1977-02-07 Kao Corp Process for preparing amphoteric polyurethane emulsions
DE2811148A1 (de) * 1978-03-15 1979-09-20 Bayer Ag Verfahren zur herstellung von waessrigen polyurethan-dispersionen und -loesungen
US4238580A (en) * 1978-05-19 1980-12-09 General Electric Company Process of forming urethane-coupled polymers of quinone-coupled polyphenylene oxides
DE2843790A1 (de) * 1978-10-06 1980-04-17 Bayer Ag Verfahren zur herstellung von waessrigen dispersionen oder loesungen von polyurethan-polyharnstoffen, die nach diesem verfahren erhaeltlichen dispersionen oder loesungen, sowie ihre verwendung
JPS5645965A (en) * 1979-09-25 1981-04-25 Asahi Denka Kogyo Kk Heat-curing composition for coat
JPS5674144A (en) * 1979-11-21 1981-06-19 Takeda Chem Ind Ltd Preparation of polyurethane emulsion
JPS56112976A (en) * 1980-02-08 1981-09-05 Takara Kenzai Seisakusho:Goushi Flexible floor coating material comprising room temp. curable antistaining polyurethane resin
US4366193A (en) * 1981-04-10 1982-12-28 Ashland Oil, Inc. Catechol-based vapor permeation curable coating compositions
JPS591521A (ja) * 1982-06-25 1984-01-06 Sanyo Chem Ind Ltd プライマ−組成物
JPS5980426A (ja) * 1982-10-29 1984-05-09 Asahi Glass Co Ltd ポリウレタン系エラストマ−の製造方法
JPS59179573A (ja) * 1983-03-30 1984-10-12 Nippon Urethane Service:Kk 熱硬化性接着剤用樹脂組成物
JPS59215310A (ja) * 1983-05-23 1984-12-05 Sanyo Chem Ind Ltd 湿気硬化型ウレタン組成物の製造法
DE3401166A1 (de) * 1984-01-14 1985-07-18 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von urethanmodifizierten polyisocyanat-zubereitungen und ihre verwendung bei der herstellung von polyurethankunststoffen
US4522979A (en) * 1984-02-17 1985-06-11 Mobay Chemical Corporation Molding compositions having an enhanced resistance to gasoline
JPS60173010A (ja) * 1984-02-17 1985-09-06 Toyo Tire & Rubber Co Ltd 耐熱、耐摩擦、耐摩耗性ポリウレタン樹脂組成物
US4569951A (en) * 1985-01-18 1986-02-11 The Dow Chemical Company Polymers prepared by reaction of a polyisocyanate with a secondary amine terminated adduct of a primary amine compound and a polyepoxide
US4645816A (en) * 1985-06-28 1987-02-24 Union Carbide Corporation Novel vulcanizable silane-terminated polyurethane polymers
JPH0686113B2 (ja) * 1985-11-27 1994-11-02 凸版印刷株式会社 レーザ製版装置
US4745137A (en) * 1986-06-25 1988-05-17 The Dow Chemical Company Polyurethanes prepared from solutions or dispersions of polymers of rigid polyaromatic monomers in polyols
US4745135A (en) * 1986-06-25 1988-05-17 The Dow Chemical Company Polyurethanes prepared from liquid crystal-containing polyols
US4701475A (en) * 1986-06-25 1987-10-20 The Dow Chemical Company Polyurethanes reinforced with rigid rod micro fillers
US4745136A (en) * 1986-06-25 1988-05-17 The Dow Chemical Company Polyurethanes prepared from dispersions or solutions of cholesterol or cholestanol-containing polymers in a polyol
SE460958B (sv) * 1986-10-02 1989-12-11 Kh Gol Sp Proizvodstvennogkhar Verktyg foer skaerning av yttergaengor

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3078257A (en) * 1957-07-06 1963-02-19 Bayer Ag Polyurethane bristles and process for their manufacture
US3330781A (en) * 1962-05-07 1967-07-11 Mobay Chemical Corp Polyurethane plastics prepared from alkylene oxide adducts of compositions comprising a major portion of trihydroxydiphenyl
US4071484A (en) * 1973-10-23 1978-01-31 Kohkoku Chemical Industry Co., Ltd. Process for preparing flexible flame retarding polyurethane foams
GB2100276A (en) * 1981-06-11 1982-12-22 Goldschmidt Ag Th Curable adhesive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO8900588A1 *

Also Published As

Publication number Publication date
WO1989000588A1 (fr) 1989-01-26
EP0299462A2 (fr) 1989-01-18
AU606737B2 (en) 1991-02-14
AU2139088A (en) 1989-02-13
EP0299462A3 (fr) 1989-01-25
EP0365599A1 (fr) 1990-05-02
JPH02502384A (ja) 1990-08-02
BR8807617A (pt) 1990-06-12
KR890701657A (ko) 1989-12-21

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