JP6441220B2 - ハロゲン化オレフィン発泡剤を含有するポリウレタンポリオールブレンドの安定性の向上 - Google Patents
ハロゲン化オレフィン発泡剤を含有するポリウレタンポリオールブレンドの安定性の向上 Download PDFInfo
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- JP6441220B2 JP6441220B2 JP2015533165A JP2015533165A JP6441220B2 JP 6441220 B2 JP6441220 B2 JP 6441220B2 JP 2015533165 A JP2015533165 A JP 2015533165A JP 2015533165 A JP2015533165 A JP 2015533165A JP 6441220 B2 JP6441220 B2 JP 6441220B2
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- polyol premix
- antioxidant
- premix composition
- substituted
- polyol
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 189
- 229920005862 polyol Polymers 0.000 title claims description 133
- 150000003077 polyols Chemical class 0.000 title claims description 133
- 239000004604 Blowing Agent Substances 0.000 title claims description 49
- 229920002635 polyurethane Polymers 0.000 title claims description 25
- 239000004814 polyurethane Substances 0.000 title claims description 25
- 150000001336 alkenes Chemical class 0.000 title description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 10
- 239000003054 catalyst Substances 0.000 claims description 120
- 239000003963 antioxidant agent Substances 0.000 claims description 101
- 230000003078 antioxidant effect Effects 0.000 claims description 79
- 239000006260 foam Substances 0.000 claims description 79
- 150000001412 amines Chemical class 0.000 claims description 60
- 229910052751 metal Inorganic materials 0.000 claims description 32
- 239000002184 metal Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 239000004094 surface-active agent Substances 0.000 claims description 28
- -1 alkyl Motoma Chemical compound 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 23
- 229920001187 thermosetting polymer Polymers 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000011495 polyisocyanurate Substances 0.000 claims description 18
- 229920000582 polyisocyanurate Polymers 0.000 claims description 18
- 229920001296 polysiloxane Polymers 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 150000007942 carboxylates Chemical class 0.000 claims description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- 239000003063 flame retardant Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052718 tin Inorganic materials 0.000 claims description 9
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims description 8
- WQGWDDDVZFFDIG-UHFFFAOYSA-N trihydroxybenzene Natural products OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 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 claims description 7
- 229910052797 bismuth Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229960004337 hydroquinone Drugs 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 6
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Natural products OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims description 4
- GGNQRNBDZQJCCN-UHFFFAOYSA-N hydroxyhydroquinone Natural products OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- 150000004986 phenylenediamines Chemical group 0.000 claims description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 3
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 claims description 2
- NDWWLJQHOLSEHX-UHFFFAOYSA-L calcium;octanoate Chemical compound [Ca+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NDWWLJQHOLSEHX-UHFFFAOYSA-L 0.000 claims description 2
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- AKTIAGQCYPCKFX-FDGPNNRMSA-L magnesium;(z)-4-oxopent-2-en-2-olate Chemical compound [Mg+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AKTIAGQCYPCKFX-FDGPNNRMSA-L 0.000 claims description 2
- GMDNUWQNDQDBNQ-UHFFFAOYSA-L magnesium;diformate Chemical compound [Mg+2].[O-]C=O.[O-]C=O GMDNUWQNDQDBNQ-UHFFFAOYSA-L 0.000 claims description 2
- HPBJPFJVNDHMEG-UHFFFAOYSA-L magnesium;octanoate Chemical compound [Mg+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HPBJPFJVNDHMEG-UHFFFAOYSA-L 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 2
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims 6
- 150000008109 benzenetriols Chemical class 0.000 claims 3
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims 2
- 150000008110 hydroxyquinols Chemical class 0.000 claims 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 2
- 150000003232 pyrogallols Chemical class 0.000 claims 2
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims 1
- 235000006708 antioxidants Nutrition 0.000 description 73
- 238000006243 chemical reaction Methods 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 238000005187 foaming Methods 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 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 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000000087 stabilizing effect Effects 0.000 description 9
- 230000032683 aging Effects 0.000 description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
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- 229910052731 fluorine Inorganic materials 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 7
- 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 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
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- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
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- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- NUPBXTZOBYEVIR-UHFFFAOYSA-N 1,1,2,3,3,4,4-heptafluorobut-1-ene Chemical class FC(F)C(F)(F)C(F)=C(F)F NUPBXTZOBYEVIR-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
- C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
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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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/1816—Catalysts containing secondary or tertiary amines or salts thereof having carbocyclic 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
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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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- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
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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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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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Description
R1R2N(CH2)2X
(式中:
R1およびR2は、同じもしくは異なるものであり、それぞれ、メチルなどの、C1〜C6アルキル基、および/または−CH2CH2OHもしくはCH2CH(CH3)OHなどの、アルカノール基であり;Xは、O(CH2)2Y、OH、またはNR3(CH2)2Yであり、ここで、R3は、メチルなどの、C1〜C6アルキル基、または−CH2CH2OHもしくはCH2CH(CH3)OHなどの、アルカノール基であり;Yは、OHまたはNR4R5であり、ここで、R4およびR5は、同じもしくは異なるものであり、それぞれ、メチルなどの、C1〜C6アルキル基、および/または−CH2CH2OHもしくは−CH2CH(CH3)OHなどの、アルカノール基である)に相当する化合物が挙げられ、ただし、この化合物は少なくとも1つのエーテルおよび/またはヒドロキシル基を含有する。
ビス−(2−ジメチルアミノエチル)エーテル;
N,N−ジメチルエタノールアミン;
N−エチルモルホリン;
N−メチルモルホリン;
N,N,N’−トリメチル−N’−ヒドロキシエチル−ビスアミノエチルエーテル;
N−(3−ジメチルアミノプロピル)−N,N−ジイソプロパノールアミン;
N,N−ビス(3−ジメチルアミノプロピル)−N−イソプロパノールアミン;
2−(2−ジメチルアミノエトキシ)エタノール;
N,N,N’−トリメチルアミノエチル−エタノールアミン;および
2,2’−ジモルホリノジエチルエーテル、ならびにそれらの混合物
が挙げられる。
(a)ジフルオロメタン(HFC32);1,1,1,2,2−ペンタフルオロエタン(HFC125);1,1,1−トリフルオロエタン(HFC143a);1,1,2,2−テトラフルオロエタン(HFC134);1,1,1,2−テトラフルオロエタン(HFC134a);1,1−ジフルオロエタン(HFC152a);1,1,1,2,3,3,3−ヘプタフルオロプロパン(HFC227ea);1,1,1,3,3−ペンタフルオプロパン(HFC245fa);1,1,1,3,3−ペンタフルオブタン(HFC365mfc)および1,1,1,2,2,3,4,5,5,5−デカフルオロペンタン(HFC4310mee)を含むが、それらに限定されないハイドロフルオロカーボン;
(b)ペンタン異性体およびブタン異性体を含むが、それらに限定されない炭化水素;
(c)C4F9OCH3(HFE−7100)、C4F9OC2H5(HFE−7200)、CF3CF2OCH3(HFE−245cb2)、CF3CH2CHF2(HFE−245fa)、CF3CH2OCF3(HFE−236fa)、C3F7OCH3(HFE−7000)、2−トリフルオロメチル−3−エトキシドデコフルオロヘキサン(HFE 7500)、1,1,1,2,3−ヘキサフルオロ−4−(1,1,2,3,3,3−ヘキサフルオロプロポキシ)−ペンタン(HFE−7600)、1,1,1,2,2,3,5,5,5−デカフルオロ−3−メトキシ−4−(トリフルオロメチル)ペンタン(HFE−7300)、エチルノナフルオロイソブチルエーテル/エチルノナフルオロブチルエーテル(HFE 8200)、CHF2OCHF2、CHF2−OCH2F、CH2F−OCH2F、CH2F−O−CH3、シクロ−CF2CH2CF2−O、シクロ−CF2CF2CH2−O、CHF2−CF2CHF2、CF3CF2−OCH2F、CHF2−O−CHFCF3、CHF2−OCF2CHF2、CH2F−O−CF2CHF2、CF3−O−CF2CH3、CHF2CHF−O−CHF2、CF3−O−CHFCH2F、CF3CHF−O−CH2F、CF3−O−CH2CHF2、CHF2−O−CH2CF3、CH2FCF2−O−CH2F、CHF2−O−CF2CH3、CHF2CF2−O−CH3(HFE254pc)、CH2F−O−CHFCH2F、CHF2−CHF−O−CH2F、CF3−O−CHFCH3、CF3CHF−O−CH3、CHF2−O−CH2CHF2、CF3−O−CH2CH2F、CF3CH2−O−CH2F、CF2HCF2CF2−O−CH3、CF3CHFCF2−O−CH3、CHF2CF2CF2−O−CH3、CHF2CF2CH2−OCHF2、CF3CF2CH2−O−CH3、CHF2CF2−O−CH2CH3、(CF3)2CF−O−CH3、(CF3)2CH−O−CHF2、および(CF3)2CH−O−CH3、ならびにそれらの混合物などのハイドロフルオロエーテル(HFE);ならびに
(d)C1〜C5アルコール、C1〜C4アルデヒド、C1〜C4ケトン、C1〜C4エーテルおよびジエーテルならびに二酸化炭素発生材料
を含むがそれらに限定されない、他の発泡剤と組み合わせて使用することができる。
表2は、組成物が調製された直後の例示組成物のそれぞれについてのクリーム時間、ゲル化時間、および不粘着時間(「TFT」)を示す。
表3は、組成物を3日間熟成した後の組成物のそれぞれについてのクリーム時間、ゲル化時間、および不粘着時間(「TFT」)を示す。
表4は、組成物を7日間熟成した後の組成物のそれぞれについてのクリーム時間、ゲル化時間、および不粘着時間(「TFT」)を示す。
酸化防止剤の安定化効果はまた目視により観察された。触媒および発泡剤を含む対照を調製し、バイアルに入れた。第2バイアルを、酢酸を添加して第1バイアルと同様に調製した。第3バイアルを、1,2−ベンゼンジオールを添加して第1バイアルと同様に調製した。
図2は、図1に示される溶液についての経時反応性を示す。対照が酸化防止剤安定化溶液よりも経時的に著しく分解したことが明らかである。50℃での熟成は、触媒の分解を増加させた。
Claims (40)
- ハロゲン化ハイドロオレフィンを含む発泡剤、ポリオール、アミン触媒を含む触媒組成物、および酸化防止剤を含む、熱硬化性フォームブレンド製造用ポリオールプレミックス組成物であって、
前記酸化防止剤が、少なくとも1つの一次酸化防止剤または少なくとも1つの一次酸化防止剤および少なくとも1つの二次酸化防止剤を含み、
前記少なくとも1つの一次酸化防止剤が、置換または非置換のベンゼンジオールおよび置換または非置換のベンゼントリオールから選択される、
前記組成物。 - 前記少なくとも1つの一次酸化防止剤が、置換または非置換の1,2−ベンゼンジオール、置換または非置換の1,3−ベンゼンジオール、および置換または非置換の1,4−ベンゼンジオールから選択される、請求項1に記載のポリオールプレミックス組成物。
- 前記少なくとも1つの一次酸化防止剤が、置換または非置換の1,2,3−ベンゼントリオール、置換または非置換の1,2,4−ベンゼントリオール、および置換または非置換の1,3,5−ベンゼントリオールから選択される、請求項1に記載のポリオールプレミックス組成物。
- 前記酸化防止剤が、前記ポリオールプレミックスの総重量を基準として0.01重量%〜20重量%の酸化防止剤の範囲の量で存在する、請求項1〜3のいずれかに記載のポリオールプレミックス組成物。
- 前記少なくとも1つの二次酸化防止剤が、フェニレンジアミン、ホスファイト、スルフィド、サルファイト、およびメルカプチドから選択される、請求項1〜4のいずれかに記載のポリオールプレミックス組成物。
- 前記アミン触媒が酸素含有アミン触媒である、請求項1〜5のいずれかに記載のポリオールプレミックス組成物。
- 前記酸素含有アミン触媒が、アルカノールアミン、エーテルアミン、またはモルホリン基含有触媒である、請求項6に記載のポリオールプレミックス組成物。
- 前記酸素含有アミン触媒が、化学構造:
R1R2N(CH2)2X
(式中:
R1およびR2は、同じもしくは異なるものであり、それぞれC1〜C6アルキル基またはアルカノール基であり、
Xは、O(CH2)2Y、OH、またはNR3(CH2)2Yであり、ここで、R3は、C1〜C6アルキル基またはアルカノール基であり、
Yは、OHまたはNR4R5であり、ここで、R4およびR5は、同じもしくは異なるものであり、それぞれC1〜C6アルキル基またはアルカノール基である)を有する化合物であり、ただし、前記化合物がエーテルおよび/または少なくとも1つのヒドロキシル基を含有する、請求項6に記載のポリオールプレミックス組成物。 - 前記アミン触媒が非酸素含有アミン触媒である、請求項1〜5のいずれかに記載のポリオールプレミックス組成物。
- 前記触媒組成物が非アミン触媒をさらに含む、請求項1〜5のいずれかに記載のポリオールプレミックス組成物。
- 前記非アミン触媒が、スズ(Sn)もしくは鉛(Pb)またはそれらの混合物の有機金属塩を含む、請求項10に記載のポリオールプレミックス組成物。
- 前記発泡剤が、1つ以上のハイドロフルオロカーボン(HFC)、ハイドロフルオロエーテル(HFE)、炭化水素、アルコール、アルデヒド、ケトン、エーテル/ジエーテル、もしくはCO2発生材料、またはそれらの組み合わせをさらに含む、請求項1〜11のいずれかに記載のポリオールプレミックス組成物。
- 前記発泡剤が、ハイドロフルオロオレフィン(HFO)、ハイドロクロロフルオロオレフィン(HCFO)、およびそれらの混合物からなる群から選択されるハロゲン化ハイドロオレフィン、ならびに任意選択的に1つ以上のハイドロフルオロカーボン(HFC)、ハイドロフルオロエーテル(HFE)、炭化水素、アルコール、アルデヒド、ケトン、エーテル/ジエーテル、エステル、または二酸化炭素発生材料を含む、請求項1〜11のいずれかに記載のポリオールプレミックス組成物。
- 前記炭化水素が、ノルマルペンタン、イソペンタン、シクロペンタン、ネオペンタン、およびブタンからなる群から選択される、請求項12または13に記載のポリオールプレミックス組成物。
- 界面活性剤をさらに含む、請求項1〜14のいずれかに記載のポリオールプレミックス組成物。
- 前記界面活性剤が、ポリシロキサンポリオキシアルキレンブロックコポリマーシリコーン界面活性剤を含む、請求項15に記載のポリオールプレミックス組成物。
- 前記プレミックス組成物が、前記ポリオールプレミックス組成物の総重量を基準として0.3〜5重量パーセントの金属カルボキシレ−ト、アセチルアセトネート、およびアルコレートから選択される1種以上の金属化合物を含む、請求項1〜16のいずれかに記載のポリオールプレミックス組成物。
- 金属塩、金属アルコレートおよび金属アミジネートから選択される金属化合物をさらに含む、請求項1〜16のいずれかに記載のポリオールプレミックス組成物。
- 前記金属化合物が、Zn、Co、Ca、Mg、Bi、K、およびSnからなる群から選択される金属のカルボキシレート、アルコレート、および/またはアミジネートを含む、請求項18に記載のポリオールプレミックス組成物。
- 前記金属化合物が、C1〜C21カルボン酸またはアルコールのカルボキシレート、アルコレート、および/またはアミジネートを含む、請求項18に記載のポリオールプレミックス組成物。
- 前記金属化合物が、C1〜C21直鎖もしくは分岐の脂肪族モノカルボン酸またはモノアルコールのカルボキシレート、アルコレート、および/またはアミジネートを含む、請求項18に記載のポリオールプレミックス組成物。
- 前記金属化合物が、ギ酸マグネシウム、オクタン酸亜鉛、オクタン酸カルシウム、オクタン酸コバルト、オクタン酸マグネシウム、オクタン酸ビスマス、オクタン酸カリウム、およびオクタン酸第一スズ、マグネシウムアセチルアセトネート、亜鉛アセチルアセトネート、カルシウムアセチルアセトネート、コバルトアセチルアセトネート、ビスマスアセチルアセトネート、カリウムアセチルアセトネート、およびスズアセチルアセトネート、ならびにそれらの混合物からなる群から選択される、請求項18に記載のポリオールプレミックス組成物。
- 少なくとも1つの難燃剤もしくは鎮火剤をさらに含む、請求項1〜22のいずれかに記載のポリオールプレミックス組成物。
- (a)ポリイソシアネートと;(b)ハロゲン化ハイドロオレフィンを含む発泡剤、ポリオール、アミン触媒を含む触媒組成物、および酸化防止剤を含むポリオールプレミックス組成物とを組み合わせる工程を含む熱硬化性フォームブレンドの製造方法であって、
前記酸化防止剤が、少なくとも1つの一次酸化防止剤または少なくとも1つの一次酸化防止剤および少なくとも1つの二次酸化防止剤を含み、
前記少なくとも1つの一次酸化防止剤が、置換または非置換のベンゼンジオールおよび置換または非置換のベンゼントリオールから選択される、
前記方法。 - 前記アミン触媒が酸素含有アミン触媒である、請求項24に記載の方法。
- 前記酸素含有アミン触媒が、化学構造:
R1R2N(CH2)2X
(式中:
R1およびR2は、同じもしくは異なるものであり、それぞれC1〜C6アルキル基またはアルカノール基であり、
Xは、O(CH2)2Y、OH、またはNR3(CH2)2Yであり、ここで、R3は、C1〜C6アルキル基またはアルカノール基であり、
Yは、OHまたはNR4R5であり、ここで、R4およびR5は、同じもしくは異なるものであり、それぞれC1〜C6アルキル基またはアルカノール基である)を有する化合物であり、ただし、前記化合物がエーテルおよび/または少なくとも1つのヒドロキシル基を含有する、請求項25に記載の方法。 - 前記アミン触媒が非酸素含有アミン触媒である、請求項24に記載の方法。
- 前記触媒組成物がさらに非アミン触媒を含む、請求項24に記載の方法。
- 前記非アミン触媒組成物が、スズ(Sn)もしくは鉛(Pb)またはそれらの混合物の有機金属塩を含む、請求項28に記載の方法。
- 前記発泡剤が、ハイドロフルオロオレフィン(HFO)、ハイドロクロロフルオロオレフィン(HCFO)、およびそれらの混合物からなる群から選択されるハロゲン化ハイドロオレフィン、ならびに、任意選択的に、1つ以上のハイドロフルオロカーボン(HFC)、ハイドロフルオロエーテル(HFE)、炭化水素、アルコール、アルデヒド、ケトン、エーテル/ジエーテル、エステル、もしくはCO2発生材料、またはそれらの組み合わせを含む、請求項24〜29のいずれかに記載の方法。
- 前記炭化水素が、ノルマルペンタン、イソペンタン、シクロペンタン、ネオペンタン、およびブタンからなる群から選択される、請求項30に記載の方法。
- 前記プレミックス組成物が界面活性剤をさらに含む、請求項24〜31のいずれかに記載の方法。
- 前記界面活性剤が、ポリシロキサンポリオキシアルキレンブロックコポリマーシリコーン界面活性剤を含む、請求項32に記載の方法。
- 前記少なくとも1つの一次酸化防止剤が、置換または非置換の1,2−ベンゼンジオール、置換または非置換の1,3−ベンゼンジオール、および置換または非置換の1,4−ベンゼンジオールから選択される、請求項24〜33のいずれかに記載の方法。
- 前記少なくとも1つの一次酸化防止剤が、置換または非置換の1,2,3−ベンゼントリオール、置換または非置換の1,2,4−ベンゼントリオール、および置換または非置換の1,3,5−ベンゼントリオールから選択される、請求項24〜33のいずれかに記載の方法。
- 前記酸化防止剤が、前記ポリオールプレミックスの総重量を基準として1重量%〜10重量%の酸化防止剤の範囲の量で存在する、請求項24〜35のいずれかに記載の方法。
- 前記少なくとも1つの二次酸化防止剤が、フェニレンジアミン、ホスファイト、スルフィド、サルファイト、およびメルカプチドから選択される、請求項24〜36のいずれかに記載の方法。
- 前記プレミックス組成物が金属塩、金属アルコレートおよび金属アミジネートから選択される金属化合物をさらに含む、請求項24〜37のいずれかに記載の方法。
- 前記プレミックス組成物が、難燃剤または鎮火剤をさらに含む、請求項24〜38のいずれかに記載の方法。
- 一様な気泡構造を有するポリウレタンまたはポリイソシアヌレートフォームを提供するための混合物であって、(a)ポリイソシアネートと;(b)ハロゲン化ハイドロオレフィンを含む発泡剤、ポリオール、アミン触媒を含む触媒組成物、および酸化防止剤を含むポリオールプレミックス組成物とを含み、
前記酸化防止剤が、少なくとも1つの一次酸化防止剤または少なくとも1つの一次酸化防止剤および少なくとも1つの二次酸化防止剤を含み、
前記少なくとも1つの一次酸化防止剤が、置換または非置換のベンゼンジオールおよび置換または非置換のベンゼントリオールから選択される、
前記混合物。
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US201261704626P | 2012-09-24 | 2012-09-24 | |
US61/704,626 | 2012-09-24 | ||
PCT/US2013/060510 WO2014047230A1 (en) | 2012-09-24 | 2013-09-19 | Improved stability of polyurethane polyol blends containing halogenated olefin blowing agent |
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