JP2010540698A - エラストマーのためのプレポリマーおよびポリマー - Google Patents
エラストマーのためのプレポリマーおよびポリマー Download PDFInfo
- Publication number
- JP2010540698A JP2010540698A JP2010525908A JP2010525908A JP2010540698A JP 2010540698 A JP2010540698 A JP 2010540698A JP 2010525908 A JP2010525908 A JP 2010525908A JP 2010525908 A JP2010525908 A JP 2010525908A JP 2010540698 A JP2010540698 A JP 2010540698A
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- JP
- Japan
- Prior art keywords
- polyol
- polybutadiene
- weight percent
- prepolymer
- isocyanate
- 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.)
- Pending
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- 239000000806 elastomer Substances 0.000 title claims abstract description 51
- 229920000642 polymer Polymers 0.000 title claims abstract description 26
- 229920005862 polyol Polymers 0.000 claims abstract description 185
- 150000003077 polyols Chemical class 0.000 claims abstract description 184
- 239000000203 mixture Substances 0.000 claims abstract description 74
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 51
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 46
- 239000012948 isocyanate Substances 0.000 claims abstract description 33
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 239000004970 Chain extender Substances 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 19
- 239000000194 fatty acid Substances 0.000 claims description 19
- 229930195729 fatty acid Natural products 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 239000004971 Cross linker Substances 0.000 claims description 12
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- 125000000524 functional group Chemical group 0.000 claims description 6
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 14
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- 239000000463 material Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
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- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical class CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000000828 canola oil Substances 0.000 description 4
- 235000019519 canola oil Nutrition 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 235000019485 Safflower oil Nutrition 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920013701 VORANOL™ Polymers 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical group OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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Images
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- 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
- C08G18/36—Hydroxylated esters of higher fatty acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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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)
- Oil, Petroleum & Natural Gas (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
本発明は、ポリオール、プレポリマー、特に、イソシアナートおよびポリオールのプレポリマー、好ましくは、ポリオール、プレポリマーまたはこれらの組合せから製造されるエラストマーを製造するのに有用なプレポリマーに関する。
エラストマーは、通常、張力の下で伸び、大きな引張り強さを有し、そして、加えられた応力が除かれると、元の寸法に素早く戻る。このようなエラストマーは、オープンキャスティング法、射出成形、および表面のスプレーコーティングを含めて、様々な用途に用いることができる。
再生可能資源から誘導される少なくとも1種のポリオールをポリブタジエンポリオールと組み合わせて調製されるプレポリマーが、エラストマーの製造に使用されるとき、良好な物理的性質および耐薬品性を有するエラストマーを生成することが、見出された。
a)化学量論的に過剰の1種以上のジ−またはポリイソシアナートと、第1ポリオール組成物との反応生成物を含む、5〜25重量パーセントのイソシアナート(NCO)含量を有するイソシアナート末端プレポリマー(ここで、第1ポリオール組成物は、10〜90重量パーセントの少なくとも1種の天然オイル系ポリオール;10〜90重量パーセントの少なくとも1種のポリブタジエンポリオールを、必要に応じて、さらなるポリオールの存在下で含む);
b)第2ポリオール組成物(ここで、ポリブタジエンポリオールまたは天然オイルポリオールではないどのポリオールも、1.8〜2.5の公称官能基数(nominal functionality)および500〜10,000の平均分子量を有するポリオールまたはポリオールブレンドである);
を、
c)必要に応じて、鎖延長剤および/または架橋剤の存在下で;および
d)必要に応じて、触媒、およびエラストマーの製造においてそれら自体が知られている他の添加剤の存在下で;
混合したものを含むエラストマーである。
a)化学量論的に過剰の1種以上のジ−またはポリイソシアナートと、第1ポリオール組成物との反応生成物を含む、5から25重量パーセントのイソシアナート(NCO)含量を有するイソシアナート末端プレポリマー(ここで、第1ポリオール組成物は、10〜90重量パーセントの少なくとも1種の天然オイル系ポリオール;10〜90重量パーセントの少なくとも1種のポリブタジエンポリオールを、必要に応じて、さらなるポリオールの存在下で含む);
b)第2ポリオール組成物(ここで、ポリブタジエンポリオールまたは天然オイルポリオールではないどのポリオールも、1.8〜2.5の公称官能基数および500〜10,000の平均分子量を有するポリオールまたはポリオールブレンドである);
を、
c)必要に応じて、鎖延長剤および/または架橋剤の存在下で;および
d)必要に応じて、触媒、およびエラストマーの製造においてそれら自体が知られている他の添加剤の存在下で;
混合する工程を含む、エラストマーを製造するためのプロセスである。
本発明は、ポリブタジエン系またはポリエーテル系のエラストマーに基づく系に比べて同等のまたは向上した耐薬品性を示す、複数成分コーティング系の調製および利用に関する。向上した性質は、このようなコーティング系を、腐食性環境における使用に適したものにする。
Kは、Krasol LBH2000の商用名を有するポリブタジエンポリオール(ジオール)に対して用いられる呼称であり、約1.9の報告された官能基数(reported functionality)および平均2000のMW(範囲 1800〜2500)、40〜65mgKOH/gのOH価、5000〜20000mPa.sの粘度(25℃)を有する。KrasolはSartomer Europeの商標である。
DETAは、Albemarleから入手されるジエチルトルエンジアミン(DETDA)であり、2官能性芳香族アミン鎖延長剤である。
T-5000は、The Hanson Group, LLCから入手可能な、5000のMWのポリエーテルアミンである。T-5000の報告されている別称は、α,α’,α”−1,2,3−プロパントリイルトリス(ω−(2−アミノメチルエトキシ)−ポリ−オキシ(メチル−1,2−エタンジイル))である。
Polylink 4200は、第2級芳香族ジアミンであり、The Hanson Group, LLCから入手可能で、310の分子量および362の見掛けのヒドロキシル価を有する。
D-2000は、The Hanson Group, LLCから入手可能な、2,000の分子量を有するポリエーテルアミンである。T2000の報告されている別称は、α−(2−アミノメチルエチル)−ω−(2−アミノメチルエトキシ)−ポリ(オキシ(メチル−1,2−エタンジイル))である。
ISO-1は、モノメリックMDIのISONATE*50-OPであり、The Dow Chemical Companyから入手可能で、約50/50の2,4’/4,4’異性体比を有する。
Vは、The Dow Chemical Companyから入手可能な、MWが1000で、全てPOジオールのVORANOL* V220-110の呼称である。
*ISONATEおよびVORANOLは、The Dow Chemical Companyの商標である。
Sは、天然オイル系ポリオール(NOBP)の呼称である。このポリオール(MWが2000のジオール)は、メチルヒドロキシメチルステアラート(HMS)の重合に基づく。このポリオールは、UnoxolTMの商用名でThe Dow Chemical Companyから市販されている、混合1,3および1,4−シクロヘキサンジメタノール(36.2g)と、メチル9−ヒドロキシメチルステアラート(165.0g;純度>90%)との反応によって製造される。反応物は、短経路コンデンサー、受けフラスコ(receiving flask)、窒素入口、窒素出口(ミネラルオイルバブラーに向かう)、および磁気撹拌子を装備した500mlの3つ口丸底フラスコに投入する。混合物を、熱電対コントローラによって加減される油浴中で120℃に加熱し、混合の間、窒素雰囲気下に保つ。120℃で、内容物を、3回、脱気し、窒素により戻し充填し、次いで、触媒(ジブチルスズオキシド)を、投入重量に対して、1000ppmで添加する。温度は、190℃に達するまで、30分当たり10℃で上昇させる。
板を、W.R.Schmeal、Polymeric Engineering and Science、119、13、1173頁に記載の修正手順を用いて準備する。ドローダウンバーを用いるのでなく、プレポリマーおよびポリオール成分は、スタティックミキサーを通して混合し、プラスチックで覆った2ロールプレスを通す。準備した後、板は平らに置き、15から20分間、静置し、その後、プラスチックの覆いを取り除く。得られた板は、周囲条件(ambient condition)で一晩、さらに硬化させ、その後、任意の機械的試験を実施する。
Claims (11)
- 化学量論的に過剰の1種以上のジ−またはポリイソシアナートと、第1ポリオール組成物との反応生成物を含む、5〜25重量パーセントのイソシアナート(NCO)含量を有するイソシアナート末端プレポリマーであって、第1ポリオール組成物が、10〜90重量パーセントの少なくとも1種の天然オイル系ポリオール;10〜90重量パーセントの少なくとも1種のポリブタジエンポリオールを、必要に応じてさらなるポリオールの存在下で含む、プレポリマー。
- ポリブタジエンが1.8〜2.1の官能基数および500〜10,000の平均分子量を有する、請求項1に記載のプレポリマー。
- ポリブタジエンが1,000〜5,000の分子量を有する、請求項1または2に記載のプレポリマー。
- ポリブタジエンが、第1ポリオール組成物の20〜75重量パーセントを占める、請求項3に記載のプレポリマー。
- ポリブタジエンが、第1ポリオール組成物の35〜66重量パーセントを占める、請求項4に記載のプレポリマー。
- 天然オイル系ポリオールが、少なくとも1種の開始剤と、少なくとも1種の脂肪酸または少なくとも1種の脂肪酸誘導体との反応生成物である、少なくとも1種のポリエステルポリオールまたは脂肪酸由来ポリオールである、請求項1〜5のいずれか一項に記載のプレポリマー。
- 開始剤が平均で1.7〜4個の反応性基を有する、請求項6に記載のプレポリマー。
- 天然オイル系ポリオールが500〜5,000の平均分子量を有する、請求項7に記載のプレポリマー。
- 天然オイル系ポリオールが、第1ポリオール組成物の35〜66重量パーセントを占める、請求項6に記載のプレポリマー。
- a)化学量論的に過剰の1種以上のジ−またはポリイソシアナートと、第1ポリオール組成物との反応生成物を含む、5〜25重量パーセントのイソシアナート(NCO)含量を有するイソシアナート末端プレポリマー(ここで、第1ポリオール組成物は、10〜90重量パーセントの少なくとも1種の天然オイル系ポリオール;10〜90重量パーセントの少なくとも1種のポリブタジエンポリオールを、必要に応じて、さらなるポリオールの存在下で含む);
b)第2ポリオール組成物(ここで、ポリブタジエンポリオール、または天然オイルポリオール(これはポリブタジエンではない)ではないどのポリオールも、1.8〜2.5の公称官能基数および500〜10,000の平均分子量を有するポリオールまたはポリオールブレンドである);
を、
c)必要に応じて、鎖延長剤および/または架橋剤の存在下で;および
d)必要に応じて、触媒、およびエラストマーの製造においてそれら自体が知られている他の添加剤の存在下で
混合したものを含むエラストマー。 - a)化学量論的に過剰の1種以上のジ−またはポリイソシアナートと、第1ポリオール組成物との反応生成物を含む、5〜25重量パーセントのイソシアナート(NCO)含量を有するイソシアナート末端プレポリマー(ここで、第1ポリオール組成物は、10〜90重量パーセントの少なくとも1種の天然オイル系ポリオール;10〜90重量パーセントの少なくともポリブタジエンポリオールを、必要に応じて、さらなるポリオールの存在下で含む);
b)第2ポリオール組成物(ここで、ポリブタジエンポリオール、または天然オイルポリオール(これはポリブタジエンではない)ではないどのポリオールも、1.8〜2.5の公称官能基数および500〜10,000の平均分子量を有するポリオールまたはポリオールブレンドである);
を、
c)必要に応じて、鎖延長剤および/または架橋剤の存在下で;および
d)必要に応じて、触媒、およびエラストマーの製造においてそれら自体が知られている他の添加剤の存在下で
混合する工程を含む、エラストマーを製造するためのプロセス。
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Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BRPI0815869A2 (pt) * | 2007-09-21 | 2019-02-26 | Dow Global Technologies Inc | elastômero e processo para apreparação de polímeros não celulares baseados em isocianato |
US20130005900A1 (en) * | 2010-03-12 | 2013-01-03 | Dow Global Technologies Llc | Gels and soft elastomers made with natural oil based polyols |
US20130018147A1 (en) * | 2010-03-31 | 2013-01-17 | Dow Global Technologies Llc | Polyurethane/polyurea spray elastomers |
US9522396B2 (en) | 2010-12-29 | 2016-12-20 | S.D. Sight Diagnostics Ltd. | Apparatus and method for automatic detection of pathogens |
US20130040128A1 (en) * | 2011-08-12 | 2013-02-14 | Carl E. Boddie | Highly corrosion resistant polyurea composition |
CN104169719B (zh) | 2011-12-29 | 2017-03-08 | 思迪赛特诊断有限公司 | 用于检测生物样品中病原体的方法和*** |
US9018432B2 (en) | 2012-10-25 | 2015-04-28 | Barnhardt Manufacturing Company | Processing radioactive waste for shipment and storage |
EP2961412A4 (en) | 2013-02-26 | 2016-11-09 | Triact Therapeutics Inc | CANCER THERAPY |
EP3052539B1 (en) | 2013-10-02 | 2017-08-02 | Dow Global Technologies LLC | Sprayable polyurethane based protective coating |
EP3859425B1 (en) | 2015-09-17 | 2024-04-17 | S.D. Sight Diagnostics Ltd. | Methods and apparatus for detecting an entity in a bodily sample |
JP7214729B2 (ja) | 2017-11-14 | 2023-01-30 | エス.ディー.サイト ダイアグノスティクス リミテッド | 光学測定用試料収容器 |
CN111655300B (zh) * | 2018-01-12 | 2022-09-30 | 科思创知识产权两合公司 | 制备弹性和抗撕裂聚氨酯泡沫的方法及其用途 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4923298A (ja) * | 1972-06-27 | 1974-03-01 | ||
JPS5780421A (en) * | 1980-11-10 | 1982-05-20 | Idemitsu Kosan Co Ltd | Polyurethane composition |
JPH0885717A (ja) * | 1994-09-16 | 1996-04-02 | Mitsui Toatsu Chem Inc | ウレタンエラストマーの製造方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4168258A (en) * | 1978-02-15 | 1979-09-18 | N L Industries, Inc. | Grease compatible, mineral oil extended polyurethane |
CA1290631C (en) * | 1985-05-13 | 1991-10-15 | Hirohisa Maki | Protective coating on concrete construction |
US4742112A (en) * | 1987-01-23 | 1988-05-03 | Caschem, Inc. | Ricinoleate modified hydrocarbon polyols |
DE3915426A1 (de) * | 1989-05-11 | 1990-11-15 | Bayer Ag | Verfahren zur herstellung von hochelastischen, chemikalienbestaendigen polyurethankunststoffen und -beschichtungen |
DE60100395T2 (de) * | 2000-05-10 | 2004-04-22 | Rohm And Haas Co. | Heissschmelzklebstoff |
US6797789B2 (en) * | 2001-10-19 | 2004-09-28 | Visuron Technologies, Inc. | Phenolic/polyurea coating co-polymer compositions and process |
US7056976B2 (en) * | 2002-08-06 | 2006-06-06 | Huntsman International Llc | Pultrusion systems and process |
-
2008
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- 2008-09-17 CN CN200880116654A patent/CN101861347A/zh active Pending
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4923298A (ja) * | 1972-06-27 | 1974-03-01 | ||
JPS5780421A (en) * | 1980-11-10 | 1982-05-20 | Idemitsu Kosan Co Ltd | Polyurethane composition |
JPH0885717A (ja) * | 1994-09-16 | 1996-04-02 | Mitsui Toatsu Chem Inc | ウレタンエラストマーの製造方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6160891B1 (ja) * | 2015-12-16 | 2017-07-12 | Dic株式会社 | 湿気硬化型ウレタンホットメルト樹脂組成物、及び積層体 |
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