JP5671193B1 - 硬質ポリウレタンフォーム製造用ポリオール混合物 - Google Patents
硬質ポリウレタンフォーム製造用ポリオール混合物 Download PDFInfo
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- JP5671193B1 JP5671193B1 JP2014550968A JP2014550968A JP5671193B1 JP 5671193 B1 JP5671193 B1 JP 5671193B1 JP 2014550968 A JP2014550968 A JP 2014550968A JP 2014550968 A JP2014550968 A JP 2014550968A JP 5671193 B1 JP5671193 B1 JP 5671193B1
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- 229920005903 polyol mixture Polymers 0.000 title claims abstract description 101
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 54
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 title claims description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 79
- 239000003054 catalyst Substances 0.000 claims abstract description 66
- 229920005862 polyol Polymers 0.000 claims abstract description 51
- 150000003077 polyols Chemical class 0.000 claims abstract description 51
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000007524 organic acids Chemical class 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
- NLOLSXYRJFEOTA-UPHRSURJSA-N (z)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C/C(F)(F)F NLOLSXYRJFEOTA-UPHRSURJSA-N 0.000 claims abstract description 20
- 239000006260 foam Substances 0.000 claims abstract description 20
- 239000001384 succinic acid Substances 0.000 claims abstract description 18
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims abstract description 16
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003381 stabilizer Substances 0.000 claims abstract description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 22
- 239000005056 polyisocyanate Substances 0.000 claims description 22
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 claims description 19
- 239000004604 Blowing Agent Substances 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 13
- 235000005985 organic acids Nutrition 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 abstract description 19
- 239000004566 building material Substances 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 8
- 239000011810 insulating material Substances 0.000 abstract description 7
- 238000009833 condensation Methods 0.000 abstract description 6
- 230000005494 condensation Effects 0.000 abstract description 5
- 230000009257 reactivity Effects 0.000 description 31
- -1 imidazole compound Chemical class 0.000 description 30
- 238000005187 foaming Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 238000003860 storage Methods 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 229920005906 polyester polyol Polymers 0.000 description 12
- 150000003512 tertiary amines Chemical class 0.000 description 12
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- 239000003153 chemical reaction reagent Substances 0.000 description 11
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- JRENXZBKMHPULY-UPHRSURJSA-N (z)-2-chloro-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C(/Cl)C(F)(F)F JRENXZBKMHPULY-UPHRSURJSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000009413 insulation Methods 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 150000007519 polyprotic acids Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- SVNWKKJQEFIURY-UHFFFAOYSA-N 2-methyl-1-(2-methylpropyl)imidazole Chemical compound CC(C)CN1C=CN=C1C SVNWKKJQEFIURY-UHFFFAOYSA-N 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000010419 fine particle Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 229920000265 Polyparaphenylene Polymers 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 3
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- WHLZPGRDRYCVRQ-UHFFFAOYSA-N 1-butyl-2-methylimidazole Chemical compound CCCCN1C=CN=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
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- 239000000600 sorbitol Substances 0.000 description 2
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Classifications
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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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
〔1〕 硬質ポリウレタンフォームを製造するためのポリオール混合物であって、
(A)水酸基価が100mgKOH/g以上550mgKOH/g以下であるポリオール成分、
(B)トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)及びシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)からなる群より選ばれた1種以上のヒドロハロオレフィン系発泡剤を含む発泡剤、
(C)式(I):
で表されるイミダゾール系触媒(C1)を含む触媒、
(D)コハク酸及びグルタル酸からなる群より選ばれた1種以上を含む有機酸、ならびに
(E)整泡剤
を含有してなるポリオール混合物。
〔2〕 前記〔1〕記載のポリオール混合物とポリイソシアネート成分とを混合し、発泡及び硬化反応させる工程を有する、硬質ポリウレタンフォームの製造法。
本発明のポリオール混合物は、
(A)水酸基価が100mgKOH/g以上550mgKOH/g以下であるポリオール成分、
(B)トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(以降、「TCTFP」ともいう)(B1)及びシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(以降、「CHFB」ともいう)(B2)からなる群より選ばれた1種以上のヒドロハロオレフィン系発泡剤を含む発泡剤、
(C)式(I):
で表されるイミダゾール系触媒(C1)を含む触媒、
(D)コハク酸及びグルタル酸からなる群より選ばれた1種以上を含む有機酸、ならびに
(E)整泡剤
を含有するものである。
本発明における(A)ポリオール成分は、水酸基価(単位:[mgKOH/g])が100以上550以下である。前記水酸基価は、硬質ポリウレタンフォームに強度を付与する観点から、100以上であり、好ましくは150以上、より好ましくは200以上であり、同様の観点から、550以下であり、好ましくは500以下、より好ましくは480以下である。ここで、(A)成分の水酸基価とは、(A)成分を構成するポリオールが1種類の場合はそのものの水酸基価を意味する。(A)成分を構成するポリオールが2種類以上の場合は加重平均した水酸基価を意味し、加重平均水酸基価が前記範囲内となるのであれば前記水酸基価を有さないポリオールが含まれていてもよい。なお、本明細書において、水酸基価はJIS K1557に基づいて求めたときの値である。
本発明における(B)発泡剤としては、地球環境保護の観点からオゾン破壊係数が実質的にゼロであり、地球温暖化係数が20以下のヒドロハロオレフィンが挙げられ、取扱い容易性とポリウレタンフォームの発泡特性の観点から、TCTFP又はCHFBを用いる。これらは、それぞれ単独で又は2種を組み合わせて用いることができる。なお、本明細書において、TCTFPとCHFBをまとめて、「本発明に係わるヒドロハロオレフィン系発泡剤」と記載することがある。本発明に係わるヒドロハロオレフィン系発泡剤としては、断熱性、入手容易性及び経済性の観点から、より好ましくはTCTFPである。
本発明における(C)触媒としては、ポリオール混合物の反応性及び外観に対する経日劣化の抑制(保存安定性の向上)の観点から、式(I):
で表されるイミダゾール系触媒(C1)を用いる。
本発明における(D)有機酸としては、初期の反応性を向上させ、反応性及び外観に対する経日劣化の抑制(保存安定性の向上)の観点から、コハク酸又はグルタル酸を用い、反応性向上の有効性の観点からコハク酸が好ましい。これらは、それぞれ単独で用いてもよく、2種を併用してもよい。
本発明における(E)整泡剤としては本発明分野で公知のものが挙げられ、例えば、ポリオキシアルキレン−ポリジメチルシロキサン共重合体、ポリジアルキルシロキサン、ポリオキシアルキレンポリオール変性ジメチルポリシロキサン等のシリコーン系整泡剤、脂肪酸塩、硫酸エステル塩、リン酸エステル塩、スルホン酸塩等の陰イオン界面活性剤等が挙げられ、これらは、それぞれ単独で又は2種以上を組み合わせて用いることができる。これらのなかでは、強い整泡力及び寸法安定性の観点から、シリコーン系整泡剤が好ましく、ポリオキシアルキレン−ポリジメチルシロキサン共重合体がより好ましい。
ポリオール混合物には、(A)成分〜(E)成分以外に、必要により他の助剤が含まれていても構わない。他の助剤としては、一般に硬質ポリウレタンフォームの製造の際に使用されている助剤、例えば、架橋剤、難燃剤、顔料、充填剤等が挙げられる。これらの助剤は、本発明の目的を阻害しない範囲内で用いることができ、その含有量も公知技術に従って適宜調整することができる。
本発明の硬質ポリウレタンフォームの製造法は、前記ポリオール混合物とポリイソシアネート成分とを混合し、発泡及び硬化反応させる工程を有するものである。
(A)水酸基価が100mgKOH/g以上550mgKOH/g以下であるポリオール成分、
(B)トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)及びシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)からなる群より選ばれた1種以上のヒドロハロオレフィン系発泡剤を含む発泡剤、
(C)式(I):
で表されるイミダゾール系触媒(C1)を含む触媒、
(D)コハク酸及びグルタル酸からなる群より選ばれた1種以上を含む有機酸、ならびに
(E)整泡剤
を含有してなるポリオール混合物。
<3> (A)ポリオール成分が、好ましくはポリエステルポリオール、ポリエーテルポリオール、ポリマーポリオール、フェノール樹脂系ポリオール、及びマンニッヒポリオールからなる群より選ばれる1種又は2種以上のポリオールを含む、前記<1>又は<2>記載のポリオール混合物。
<4> ポリエステルポリオールが、好ましくはフタル酸系ポリエステルポリオールである、前記<3>記載のポリオール混合物。
<5> ポリオール混合物100質量部中の(A)成分の量は、50質量部以上が好ましく、55質量部以上がより好ましく、60質量部以上が更に好ましく、また、90質量部以下が好ましく、85質量部以下がより好ましい、前記<1>〜<4>いずれか記載のポリオール混合物。
<6> (B)発泡剤としては、TCTFPが好ましい、前記<1>〜<5>いずれか記載のポリオール混合物。
<7> (B)発泡剤が、好ましくはさらに水を含む、前記<1>〜<6>いずれか記載のポリオール混合物。
<8> (A)成分100質量部に対する水の量は、0.3質量部以上が好ましく、0.5質量部以上がより好ましく、また、3質量部以下が好ましく、2.5質量部以下がより好ましく、2.2質量部以下が更に好ましい、前記<7>記載のポリオール混合物。
<9> (B)成分におけるTCTFPとCHFBとの合計含有量は、85質量%以上が好ましく、92質量%以上がより好ましく、また、100質量%以下が好ましく、98質量%以下がより好ましく、96質量%以下が更に好ましい、前記<1>〜<8>いずれか記載のポリオール混合物。
<10> (B)成分におけるTCTFPの含有量は、85質量%以上が好ましく、92質量%以上がより好ましく、また、100質量%以下が好ましく、98質量%以下がより好ましく、96質量%以下が更に好ましい、前記<1>〜<8>いずれか記載のポリオール混合物。
<11> (B)成分の量は、(A)成分100質量部に対して、7質量部以上が好ましく、10質量部以上がより好ましく、15質量部以上が更に好ましく、また、45質量部以下が好ましく、40質量部以下がより好ましく、35質量部以下が更に好ましい、前記<1>〜<10>いずれか記載のポリオール混合物。
<12> 式(I)で表されるイミダゾール系触媒(C1)が、1,2−ジメチルイミダゾール、1−n−ブチル−2−メチルイミダゾール、及び1−イソブチル−2−メチルイミダゾールからなる群より選ばれる1種又は2種以上であることが好ましく、1−イソブチル−2−メチルイミダゾールであることがより好ましい、前記<1>〜<11>いずれか記載のポリオール混合物。
<13> (C)触媒が、好ましくは、さらに第3級アミン触媒、その誘導体、及びそれらの塩からなる群より選ばれる1種又は2種以上を含む、前記<1>〜<12>いずれか記載のポリオール混合物。
<14> (C)成分における式(I)で表されるイミダゾール系触媒(C1)の含有量は、50質量%以上が好ましく、60質量%以上がより好ましく、70質量%以上が更に好ましく、また、100質量%以下が好ましい、前記<1>〜<13>いずれか記載のポリオール混合物。
<15> 式(I)で表されるイミダゾール系触媒(C1)の量は、(A)成分100質量部に対して、1.2質量部以上が好ましく、1.5質量部以上がより好ましく、1.8質量部以上が更に好ましく、また、5.5質量部以下が好ましく、5.0質量部以下がより好ましく、4.5質量部以下が更に好ましく、3.5質量部以下がより更に好ましい、前記<1>〜<14>いずれか記載のポリオール混合物。
<16> TCTFP(B1)とCHFB(B2)の合計含有量と式(I)で表されるイミダゾール系触媒(C1)の含有量との質量比[(B1+B2)/C1]は、5以上が好ましく、6以上がより好ましく、6.5以上が更に好ましく、6.7以上が更に好ましく、7.5以上が更に好ましく、8.0以上が更に好ましく、また、22以下が好ましく、20以下がより好ましく、18以下が更に好ましく、17.5以下が更に好ましく、13以下が更に好ましい、前記<1>〜<15>いずれか記載のポリオール混合物。
<17> (C)成分の量は、(A)成分100質量部に対して、1.2質量部以上が好ましく、1.5質量部以上がより好ましく、1.8質量部以上が更に好ましく、また、15質量部以下が好ましく、10質量部以下がより好ましく、8質量部以下が更に好ましい、前記<1>〜<16>いずれか記載のポリオール混合物。
<18> (D)有機酸としては、コハク酸が好ましい、前記<1>〜<17>いずれか記載のポリオール混合物。
<19> (D)成分におけるコハク酸及びグルタル酸の合計含有量は、50質量%以上が好ましく、60質量%以上がより好ましく、70質量%以上が更に好ましく、100質量%以下が好ましい、前記<1>〜<18>いずれか記載のポリオール混合物。
<20> TCTFP(B1)とCHFB(B2)との合計含有量と、コハク酸とグルタル酸を含めた(D)有機酸の合計含有量との質量比[(B1+B2)/D]は、10以上が好ましく、13以上がより好ましく、14以上が更に好ましく、14.5以上が更に好ましく、また、40以下が好ましく、35以下がより好ましく、32以下が更に好ましく、31以下が更に好ましい、前記<1>〜<19>いずれか記載のポリオール混合物。
<21> (D)成分の量は、(A)成分100質量部に対して、0.3質量部以上が好ましく、0.5質量部以上がより好ましく、また、3質量部以下が好ましく、2質量部以下がより好ましい、前記<1>〜<20>いずれか記載のポリオール混合物。
<22> (E)整泡剤としては、ポリオキシアルキレン−ポリジメチルシロキサン共重合体、ポリジアルキルシロキサン、ポリオキシアルキレンポリオール変性ジメチルポリシロキサン等のシリコーン系整泡剤、及び、脂肪酸塩、硫酸エステル塩、リン酸エステル塩、スルホン酸塩等の陰イオン界面活性剤からなる群より選ばれる1種又は2種以上が好ましく、シリコーン系整泡剤がより好ましく、ポリオキシアルキレン−ポリジメチルシロキサン共重合体がさらに好ましい、前記<1>〜<21>いずれか記載のポリオール混合物。
<23> (E)成分の量は、(A)成分100質量部に対して、0.2質量部以上が好ましく、0.5質量部以上がより好ましく、1.0質量部以上が更に好ましく、また、4.0質量部以下が好ましく、3.5質量部以下がより好ましく、3.0質量部以下が更に好ましく、2.0質量部以下がより更に好ましい、前記<1>〜<22>いずれか記載のポリオール混合物。
<24> さらに、架橋剤、難燃剤、顔料、及び充填剤からなる群より選ばれる1種又は2種以上を含有してなる、前記<1>〜<23>いずれか記載のポリオール混合物。
<25> 難燃剤の量は、(A)成分100質量部に対して、好ましくは10質量部以上30質量部以下である、前記<24>記載のポリオール混合物。
<26> (A)成分〜(E)成分、及び必要に応じてその他の成分を混合することにより得られる、前記<1>〜<25>いずれか記載のポリオール混合物。
<27> 硬質ポリウレタンフォーム製造のための、前記<1>〜<26>いずれか記載のポリオール混合物の使用。
<28> 前記<1>〜<26>いずれか記載のポリオール混合物とポリイソシアネート成分とを混合し、発泡及び硬化反応させる工程を有する、硬質ポリウレタンフォームの製造法。
<29> ポリイソシアネート成分としては、ポリメチレンポリフェニレンポリイソシアネート、トリレンジイソシアネート、ジフェニルメタンジイソシアネート、キシリレンジイソシアネート、ナフチレンジイソシアネート等の芳香族ポリイソシアネート;ウレタン結合、カルボジイミド結合、ウレトイミン結合、アロファネート結合、ウレア結合、ビューレット結合、イソシアヌレート結合等の1種以上を含有する前記ポリイソシアネート変性物からなる群より選ばれる1種又は2種以上が好ましく、ポリメチレンポリフェニレンポリイソシアネートがより好ましい、前記<28>記載の製造法。
<30> イソシアネートインデックスが好ましくは90以上、より好ましくは100以上、更に好ましくは105以上であり、好ましくは400以下、より好ましくは300以下、更に好ましくは250以下である、前記<28>又は<29>記載の製造法。
<31> 前記<28>〜<30>いずれか記載の製造法により得られる、硬質ポリウレタンフォーム。
<32> 前記<31>記載の硬質ポリウレタンフォームの、建材、電気冷蔵庫、冷蔵/冷凍倉庫、浴槽、配管等の断熱材への使用。
<33> 前記<31>記載の硬質ポリウレタンフォームの、戸建住宅、マンションや産業用配管等の結露防止材への使用。
ポリオール成分として、表1〜4に示す組成比のポリオール合計量100質量部と、難燃剤〔トリス(2−クロロイソプロピル)ホスフェート、大八化学工業社製「TMCPP」〕20質量部と、整泡剤〔シリコーン系整泡剤、旧日本ユニカー社製「L−5340」〕1.5質量部とを室温にてラボミキサーで混合し15℃に冷却した。一方、予め表1〜4に示す組成比の触媒、有機酸、水を混合溶解し、触媒含有混合物を調製した。なお、ここでいう「室温」とは、18〜25℃のことである。
<ポリオール>
・テロール693:リサイクルPET系ポリエステルポリオール〔水酸基価:250mgKOH/g、水酸基数:2、OXID社製「テロール693」〕
・455AR:トリレンジアミン系ポリエーテルポリオール〔水酸基価:450mgKOH/g、水酸基数:4、旭硝子社製「エクセノール455AR」〕
・AE−300:エチレンジアミン系ポリエーテルポリオール〔水酸基価:768mgKOH/g、水酸基数:4、三井化学ポリウレタン社製「アクトコールAE−300」〕
・RDK−133:フタル酸系ポリエステルポリオール〔水酸基価:315mgKOH/g、水酸基数:2、川崎化成工業社製「マキシモールRDK−133」〕
・S−1703:蔗糖系ポリエーテルポリオール〔水酸基価:380mgKOH/g、水酸基数:6、住化バイエルウレタン社製「スミフェン1703」〕
<整泡剤>
・L−5340:シリコーン系整泡剤〔旧日本ユニカー社製「L−5340」〕
<難燃剤>
・TCPP:〔トリス(2−クロロイソプロピル)ホスフェート、大八化学工業社製「TMCPP」〕
<発泡剤>
・ソルスティスLBA:トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン〔ハネウエル社製「ソルスティスLBA」;以下、単に「LBA」ともいう〕
<触媒>
・KL−120:1−イソブチル−2−メチルイミダゾール〔花王社製「カオーライザーNo.120」〕
・1,2−DMI:1,2−ジメチルイミダゾール、試薬〔東京化成工業社製〕
・KL−P200:ポリ3級アミノグリコール〔花王社製「カオーライザーP200」〕
・KL−1:N,N,N’,N’−テトラメチル−1,6−ヘキサンジアミン〔花王社製「カオーライザーNo.1」〕
・KL−3:N,N,N’,N”,N”−ペンタメチルジエチレントリアミン〔花王社製「カオーライザーNo.3」〕
<有機酸>
・コハク酸:試薬〔キシダ化学社製〕
・グルタル酸:試薬〔東京化成工業社製〕
・蟻酸:試薬〔シグマアルドリッチジャパン社製〕
・酢酸:試薬〔キシダ化学社製〕
・2−EH酸:2−エチルヘキサン酸、試薬〔和光純薬工業社製〕
・シュウ酸:試薬〔片山化学工業社製〕
・マロン酸:試薬〔シグマアルドリッチジャパン社製〕
・アジピン酸:試薬〔旭化成ケミカルズ社製〕
・マレイン酸:試薬〔和光純薬工業社製〕
・イソカプロン酸:試薬〔東京化成工業社製〕
実施例1〜16及び比較例1〜12で得られたポリオール混合物100gを110mL透明ガラス製サンプル瓶に注入し、キャップして密閉した。ポリオール混合物調製後3時間静置後(初期)と25℃で3週間静置保管後(3週間後)のポリオール混合物の状態(外観)を目視により観察し、以下の評価基準に従って評価を行った。評価基準の数値が大きいほど、ポリオール混合物の均一性に優れると判断できる。また、初期と3週間後の数値の差が小さいほど、ポリオール混合物の外観及び均一性に対する経日劣化が抑制され、保存安定性に優れる。
6:ポリオール混合物に異物が認められない
5:ポリオール混合物が薄く濁っているが、沈殿物なし
4:ポリオール混合物が白く濁っているが、沈殿物なし
3:ポリオール混合物に極少量のモヤ状の沈殿物あり
2:ポリオール混合物に沈殿物あり
1:アミン塩がポリオール混合物に溶解せず結晶状に析出している
得られたポリオール混合物と、イソシアネート成分〔NCO:31.4%、住化バイエルウレタン社製「スミジュール44V20」〕とをイソシアネートインデックスが110となるように15℃でラボミキサーで混合、攪拌し、得られた混合物の反応性を以下の方法で調べた。ポリオール混合物は調製直後の初期品と25℃で3週間静置保管した経日品を用いた。
300mL容のポリプロピレン製カップ〔テラオカ社製「デスカップ」〕内で攪拌された前記混合物40gのフリー発泡におけるCT(クリームタイム)、GT(ゲルタイム)に到達するまでの時間(秒)を測定した。GTに対するCTの比(CT/GT値)が小さいものの方が初期の泡化反応に対する反応性が高いと判断できる。
Claims (8)
- 硬質ポリウレタンフォームを製造するためのポリオール混合物であって、
(A)水酸基価が100mgKOH/g以上550mgKOH/g以下であるポリオール成分、
(B)トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)及びシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)からなる群より選ばれた1種以上のヒドロハロオレフィン系発泡剤を含む発泡剤、
(C)式(I):
で表されるイミダゾール系触媒(C1)を含む触媒、
(D)コハク酸及びグルタル酸からなる群より選ばれた1種以上を含む有機酸、ならびに
(E)整泡剤
を含有してなるポリオール混合物。 - (A)ポリオール成分100質量部に対して、(B)発泡剤が7質量部以上45質量部以下である請求項1記載のポリオール混合物。
- (A)ポリオール成分100質量部に対して、式(I)で表されるイミダゾール系触媒(C1)が1.2質量部以上5.5質量部以下である請求項1又は2記載のポリオール混合物。
- トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)とシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)の合計含有量と式(I)で表されるイミダゾール系触媒(C1)の含有量との質量比[(B1+B2)/C1]が5以上22以下である請求項1〜3いずれかに記載のポリオール混合物。
- トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)とシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)の合計含有量と式(I)で表されるイミダゾール系触媒(C1)の含有量との質量比[(B1+B2)/C1]が6.5以上18以下である請求項1〜3いずれかに記載のポリオール混合物。
- トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)とシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)の合計含有量と(D)有機酸の含有量との質量比[(B1+B2)/D]が10以上40以下である請求項1〜5いずれかに記載のポリオール混合物。
- トランス−1−クロロ−3,3,3−トリフルオロ−1−プロペン(B1)とシス−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(B2)の合計含有量と(D)有機酸の含有量との質量比[(B1+B2)/D]が14以上32以下である請求項1〜5いずれかに記載のポリオール混合物。
- 請求項1〜7いずれかに記載のポリオール混合物とポリイソシアネート成分とを混合し、発泡及び硬化反応させる工程を有する、硬質ポリウレタンフォームの製造法。
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JP2018131529A (ja) * | 2017-02-15 | 2018-08-23 | 三洋化成工業株式会社 | ポリウレタンフォームの製造方法 |
CN108727551A (zh) * | 2017-04-19 | 2018-11-02 | 科思创德国股份有限公司 | 一种硬质聚氨酯泡沫及其制备方法与应用 |
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CN114716722A (zh) * | 2021-01-04 | 2022-07-08 | 海信容声(广东)冰箱有限公司 | 冰箱及硬质聚氨酯泡沫、硬质聚氨酯泡沫的制备方法 |
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