WO2001042345A1 - Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer - Google Patents

Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer Download PDF

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Publication number
WO2001042345A1
WO2001042345A1 PCT/US2000/033348 US0033348W WO0142345A1 WO 2001042345 A1 WO2001042345 A1 WO 2001042345A1 US 0033348 W US0033348 W US 0033348W WO 0142345 A1 WO0142345 A1 WO 0142345A1
Authority
WO
WIPO (PCT)
Prior art keywords
molded
polymer
polyurea polymer
fatty
acid ester
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/US2000/033348
Other languages
English (en)
French (fr)
Inventor
Allan James
Kenneth B. Arnold
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
Dow Global Technologies LLC
Original Assignee
Dow Chemical Co
Dow Global Technologies 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 Dow Chemical Co, Dow Global Technologies LLC filed Critical Dow Chemical Co
Priority to AT00984079T priority Critical patent/ATE277968T1/de
Priority to DE60014435T priority patent/DE60014435T2/de
Priority to JP2001543636A priority patent/JP2003516447A/ja
Priority to EP00984079A priority patent/EP1242525B1/en
Priority to BRPI0016485-2A priority patent/BR0016485B1/pt
Priority to CA2393667A priority patent/CA2393667C/en
Priority to AU20757/01A priority patent/AU2075701A/en
Priority to MXPA02005767A priority patent/MXPA02005767A/es
Publication of WO2001042345A1 publication Critical patent/WO2001042345A1/en
Anticipated expiration legal-status Critical
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
    • C08G18/08—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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C08G18/324—Polyamines aromatic containing only one aromatic ring
    • 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
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • 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
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end 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
    • C08G18/28—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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
    • C08G18/28—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
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • 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
    • C08G2120/00—Compositions for reaction injection moulding processes

Definitions

  • a molded polymer contains too much water when it is exposed to heat, it can exhibit surface defects commonly known in the art as blistering Blistering generally occurs when moisture absorbed into the molded polymer interacts with the polymer to produce gas and the gas accumulates to form a gas pocket.
  • blister resistance is measured by soaking a test panel for two days in water and then exposing the panel to elevated temperatures. The temperature at which the panel fails is identified as the panel's temperature-capable point.
  • a polyurea-polymer formulation of the invention includes a fatty-acid ester Any fatty-acid ester suitable for providing a molded polyurea polymer prepared from a formulation of the invention with blister resistance or improved blister resistance can be used in a formulation of the invention
  • Suitable fatty-acid esters include both natural fatty-acid esters and synthetic fatty-acid esters Examples of natural fatty-acid esters include the following oils canola, castor, coconut, cotton seed, flax seed, hemp seed, jojoba, olive, palm, peanut, pumpkin seed, safflower, sesame, soybean, and sunflower
  • the molded formulation is substantially free of blisters
  • the temperature is no greater than 425 °F (218 °C) , preferably no greater than 415 °F (213°C), and more preferably no greater than 405°F (207°C)
  • a molded polyurea polymer can be exposed to such a temperature for time periods geneially used for production conditions such as time periods suitable lor postcu ⁇ ng a molded polyurea polymer or time periods suitable for subjecting an automobile having a molded polyurea polymer to, for example, an e-coat process
  • a molded polyurea polymer can be exposed to such a temperature for at least 20 minutes, preferably at least 25 minutes, and more preferably at least 30 minutes
  • the exposure is not longer than 60 minutes, preferably no longer than 50 minutes. and more preferably no longer than 45 minutes
  • a fatty-acid ester is added to a polyurea-polymer formulation in an amount of at least 0 5 weight percent, preferably at least 1 5 weight percent, and more preferably at least 2 weight percent.
  • a fatty- acid ester should not be added in such a large amount that the formulation becomes prohibitively expensive, becomes substantially difficult to process, or cannot be used lor its intended purpose
  • a fatty-acid ester is generally added in an amount no greater than 5 0 weight percent, preferably no greater than 4 weight percent, and more preferably no greatei than 3 weight percent
  • the weight percent of fatty-acid ester is based on the weight of the reaction mixture that contains the isocyanate-reactive material, which is conventionally known as the B-side reactant.
  • any active hydrogen-containing compound can be used with this invention.
  • examples of such materials include those selected from the following classes of composition, alone or in mixture: (a) alkylene oxide adducts of polyhydroxyalkanes; (b) alkylene oxide adducts of nonreducing sugars and sugar derivatives; (c) alkylene oxide adducts of phosphorus and polyphosphorus acids; and (d) alkylene oxide adducts of polyphenols.
  • Polyols of these types are referred to herein as "'base polyols.
  • an alkylene oxide adduct of polyhydroxyalkanes is an ethylene oxide adduct of trihydroxyalkanes.
  • Other useful adducts include ethylene diamine, glycerin, ammonia, 1,2,3,4- tetrahydroxy butane, fructose, and sucrose.
  • a polyurea-polymer formulation of the invention can also include a filler Any filler generally known to one of skill in the art as useful for polyurea polymers can be used Suitable tilleis include mica, clays, glass fibers, glass beads, glass rmcrospheres, and wollastonite
  • a polyurea-polymer formulation can also include a reinforcing substrate Any reinforcing substrate generally known to one of skill in the art as useful lor polyui ea polymers can be used Foi example the polymers of the invention can be prepared with reinforcing mats
  • a polyurea-polymer formulation of the invention preferably includes a polyexpoxide
  • a polyexpoxide suitable for use with the invention includes diglycidyl ethers of compounds contaimng an average of more than two, preferably not greater than 2 aromatic, cycloaliphatic, or aliphatic hydroxyl groups per molecule
  • Suitable polyepoxides also include a diglycidyl ether of dihydric bisphenol
  • a polyurea-polymer formulation can include up to 20 weight-percent polyepoxide based on the total weight of the formulation
  • the desirable isocyanate index may vary depending on other components added to a formulation of the invention
  • the isocyanate index is desirably in a range of between 1 00 and 1 40, preferably in a range of between 1 05 and 1 10, and more preferably 1 05
  • a polyurea-polymer formulation according to the invention was prepared by admixing a polyol blend with an equivalent weight of 280 ("B" side) and an MDI prepolymer (XUS 17054; The Dow Chemical Company; Freeport, Texas) having 19% mica filler (Himod 270 with SMAL surface treatment; Olgay Norton, North Carolina) and having an equivalent weight of 254 ("A" Side).
  • the formulation had an isocyanate index of 1.05.
  • a fatty-acid ester (jojoba oil) (available among others from Desert King Corp., Chula Vista, CA, or Desert Whale Joboba Co., Inc., Arlington, AZ); a catalyst (dimethyl tin dilaurate) (UL28; available from Air Products; Allentown, Pennsylvania); and a silicone surfactant (B8418; available from Goldschmitdt Chemical Corporation; Hopewell, Virginia).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)
  • Body Structure For Vehicles (AREA)
  • Vehicle Interior And Exterior Ornaments, Soundproofing, And Insulation (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Casting Or Compression Moulding Of Plastics Or The Like (AREA)
  • Injection Moulding Of Plastics Or The Like (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Peptides Or Proteins (AREA)
  • Farming Of Fish And Shellfish (AREA)
PCT/US2000/033348 1999-12-10 2000-12-08 Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer Ceased WO2001042345A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AT00984079T ATE277968T1 (de) 1999-12-10 2000-12-08 Gussblasenfreier polyharnstoff und verfahren zu seiner herstellung
DE60014435T DE60014435T2 (de) 1999-12-10 2000-12-08 Gussblasenfreier polyharnstoff und verfahren zu seiner herstellung
JP2001543636A JP2003516447A (ja) 1999-12-10 2000-12-08 耐ふくれポリウレアポリマー成形体および耐ふくれポリウレアポリマー成形体の製造方法
EP00984079A EP1242525B1 (en) 1999-12-10 2000-12-08 Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer
BRPI0016485-2A BR0016485B1 (pt) 1999-12-10 2000-12-08 mÉtodo para melhorar a resistÊncia À bolha de um polÍmero de poliurÉia e parte moldada de carroceria de automàvel.
CA2393667A CA2393667C (en) 1999-12-10 2000-12-08 Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer
AU20757/01A AU2075701A (en) 1999-12-10 2000-12-08 Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer
MXPA02005767A MXPA02005767A (es) 1999-12-10 2000-12-08 Polimero de poliurea moldeado, resistente al avejigamiento, y metodo para formar un polimero de poliurea moldeado, resistente al avejigamiento.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17029499P 1999-12-10 1999-12-10
US60/170,294 1999-12-10

Publications (1)

Publication Number Publication Date
WO2001042345A1 true WO2001042345A1 (en) 2001-06-14

Family

ID=22619321

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/033348 Ceased WO2001042345A1 (en) 1999-12-10 2000-12-08 Blister-resistant molded polyurea polymer and method of making a blister-resistant molded polyurea polymer

Country Status (13)

Country Link
US (2) US20020107321A1 (enExample)
EP (1) EP1242525B1 (enExample)
JP (1) JP2003516447A (enExample)
KR (1) KR100729943B1 (enExample)
CN (1) CN1238410C (enExample)
AT (1) ATE277968T1 (enExample)
AU (1) AU2075701A (enExample)
BR (1) BR0016485B1 (enExample)
CA (1) CA2393667C (enExample)
DE (1) DE60014435T2 (enExample)
ES (1) ES2228642T3 (enExample)
MX (1) MXPA02005767A (enExample)
WO (1) WO2001042345A1 (enExample)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1260548A1 (en) * 2001-05-24 2002-11-27 Asahi Glass Company Ltd. Plasticizer and urethane curable composition
KR101325017B1 (ko) 2013-01-25 2013-11-04 강남화성 (주) 고경도 속경성 폴리우레아 수지 조성물

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2474115C (en) 2004-06-15 2012-06-19 Construction Research & Technology Gmbh Volatile organic compound (voc) compliant sealing material
US10208227B2 (en) * 2013-01-30 2019-02-19 Lanxess Solutions Us Inc. Low free MDI prepolymers for rotational casting
CN103204747A (zh) * 2013-03-18 2013-07-17 江苏瑞丰科技实业有限公司 一种土壤改良营养型复合凝胶材料

Citations (3)

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US5525681A (en) * 1992-11-20 1996-06-11 The Dow Chemical Company Polyurea polymers having improved high temperature stability and method of making same
WO1996022182A1 (en) * 1995-01-19 1996-07-25 The Dow Chemical Company Internal mould release composition
US5713995A (en) * 1995-02-22 1998-02-03 Yissum Research Development Company Lubricous coating compositions containing jojoba oil

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GB1575205A (en) * 1976-03-29 1980-09-17 Ici Ltd Process for the production of polyurethane foam mouldings
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US4374209A (en) * 1980-10-01 1983-02-15 Interchem International S.A. Polymer-modified polyols useful in polyurethane manufacture
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NZ230314A (en) * 1988-09-09 1991-02-26 Ici Plc Polyisocyanate composition obtained from the reaction product of uretonimine and/or carbodiimide-modified polyisocyanate with a carboxylic acid
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KR950009757B1 (ko) * 1991-05-14 1995-08-28 미쓰이도오아쓰 가가쿠 가부시키가이샤 탄성 중합체와 그 제조방법
JP3017578B2 (ja) * 1991-10-28 2000-03-13 松下電工株式会社 成形材料の製造方法
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US5688590A (en) * 1995-08-21 1997-11-18 Bayer Corporation High heat resistant molded parts produced by structural reaction injection molding
DE19611690C2 (de) * 1996-03-25 2000-07-13 Bernd Neumann Beschichtungsmittel zum Aufbringen eines Schutzüberzugs bzw. einer Imprägnierung sowohl auf glatte als auch auf poröse und saugende Untergründe, Verfahren zu ihrer Herstellung und ihre Verwendung
JP3382819B2 (ja) * 1997-06-09 2003-03-04 丸尾カルシウム株式会社 水性エマルジョン樹脂塗料組成物
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Publication number Priority date Publication date Assignee Title
US5525681A (en) * 1992-11-20 1996-06-11 The Dow Chemical Company Polyurea polymers having improved high temperature stability and method of making same
WO1996022182A1 (en) * 1995-01-19 1996-07-25 The Dow Chemical Company Internal mould release composition
US5713995A (en) * 1995-02-22 1998-02-03 Yissum Research Development Company Lubricous coating compositions containing jojoba oil

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1260548A1 (en) * 2001-05-24 2002-11-27 Asahi Glass Company Ltd. Plasticizer and urethane curable composition
KR101325017B1 (ko) 2013-01-25 2013-11-04 강남화성 (주) 고경도 속경성 폴리우레아 수지 조성물

Also Published As

Publication number Publication date
US20020107321A1 (en) 2002-08-08
ES2228642T3 (es) 2005-04-16
BR0016485A (pt) 2002-09-03
CA2393667C (en) 2010-01-26
ATE277968T1 (de) 2004-10-15
US20050096403A1 (en) 2005-05-05
CN1414992A (zh) 2003-04-30
KR20020091055A (ko) 2002-12-05
CA2393667A1 (en) 2001-06-14
EP1242525A1 (en) 2002-09-25
DE60014435D1 (de) 2004-11-04
KR100729943B1 (ko) 2007-06-20
EP1242525B1 (en) 2004-09-29
BR0016485B1 (pt) 2010-08-24
DE60014435T2 (de) 2006-03-02
MXPA02005767A (es) 2004-08-12
CN1238410C (zh) 2006-01-25
AU2075701A (en) 2001-06-18
JP2003516447A (ja) 2003-05-13

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