CN103890047B - 包含颗粒的聚醚醇 - Google Patents
包含颗粒的聚醚醇 Download PDFInfo
- Publication number
- CN103890047B CN103890047B CN201280051824.0A CN201280051824A CN103890047B CN 103890047 B CN103890047 B CN 103890047B CN 201280051824 A CN201280051824 A CN 201280051824A CN 103890047 B CN103890047 B CN 103890047B
- Authority
- CN
- China
- Prior art keywords
- aethoxy sklerol
- granule
- compound
- chain
- weight
- 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.)
- Expired - Fee Related
Links
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000008187 granular material Substances 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- -1 polysiloxane chain Polymers 0.000 claims abstract description 41
- 229920000570 polyether Polymers 0.000 claims abstract description 22
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 34
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 20
- 239000004814 polyurethane Substances 0.000 claims description 16
- 229920002635 polyurethane Polymers 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229920001228 polyisocyanate Polymers 0.000 claims description 13
- 239000005056 polyisocyanate Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 description 86
- 150000003077 polyols Chemical class 0.000 description 86
- 150000005846 sugar alcohols Polymers 0.000 description 34
- 239000000203 mixture Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 22
- 229920005830 Polyurethane Foam Polymers 0.000 description 19
- 239000011496 polyurethane foam Substances 0.000 description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 16
- 239000006260 foam Substances 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 150000002513 isocyanates Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000004088 foaming agent Substances 0.000 description 11
- 239000001294 propane Substances 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 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 7
- 239000000654 additive Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 239000003974 emollient agent Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004970 Chain extender Substances 0.000 description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000010923 batch production Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 4
- 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 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 229940073561 hexamethyldisiloxane Drugs 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- KUNHMPRZRLYIFK-UHFFFAOYSA-N 1-(2-isocyanato-3-methylbutan-2-yl)-2-methylbenzene Chemical class O=C=NC(C)(C(C)C)C1=CC=CC=C1C KUNHMPRZRLYIFK-UHFFFAOYSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 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 2
- 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 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 1
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 description 1
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- IFTGEZOPUAJVMG-UHFFFAOYSA-N 1,1-dibromobut-1-ene Chemical compound CCC=C(Br)Br IFTGEZOPUAJVMG-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- WMKGMCCZGTXXQU-UHFFFAOYSA-N 2,3-benzodioxine-1,4-dione Chemical compound C1=CC=C2C(=O)OOC(=O)C2=C1 WMKGMCCZGTXXQU-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- RRNPGLHPJFTKMV-UHFFFAOYSA-N C(C)OP(OCC)=O.CC Chemical compound C(C)OP(OCC)=O.CC RRNPGLHPJFTKMV-UHFFFAOYSA-N 0.000 description 1
- PRRAWXUEDSBETE-UHFFFAOYSA-N C(CCCCCCCCC)(C(=O)O)C(=O)O.C(CCCCCCCCC)(C(=O)O)C(=O)O Chemical compound C(CCCCCCCCC)(C(=O)O)C(=O)O.C(CCCCCCCCC)(C(=O)O)C(=O)O PRRAWXUEDSBETE-UHFFFAOYSA-N 0.000 description 1
- OZSHHFOXFULRCT-UHFFFAOYSA-N CC(C)[Cs]C(C)CC(C)(CN)C(C)(C)O Chemical compound CC(C)[Cs]C(C)CC(C)(CN)C(C)(C)O OZSHHFOXFULRCT-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- VPIAKHNXCOTPAY-UHFFFAOYSA-N Heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CVXHBROPWMVEQO-UHFFFAOYSA-N Peroxyoctanoic acid Chemical compound CCCCCCCC(=O)OO CVXHBROPWMVEQO-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- KTVZZJJSXSGJSX-UHFFFAOYSA-N carbonic acid;2-propan-2-ylperoxypropane Chemical compound OC(O)=O.CC(C)OOC(C)C KTVZZJJSXSGJSX-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000011438 discrete method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229940089256 fungistat Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000011796 hollow space material Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- KHJNXCATZZIGAX-UHFFFAOYSA-N tert-butyl 2-ethyl-2-methylheptaneperoxoate Chemical compound CCCCCC(C)(CC)C(=O)OOC(C)(C)C KHJNXCATZZIGAX-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000005436 troposphere Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
-
- 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
- C08G18/4829—Polyethers containing at least three hydroxy 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
-
- 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
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
-
- 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- 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
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/128—Copolymers graft
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
- C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
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)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
Abstract
本发明涉及一种包含颗粒的聚醚醇,其可通过烯属不饱和单体在聚醚醇中原位聚合来制备,并且其特征在于所述聚合在至少一种含有聚硅氧烷链的化合物(A)的存在下进行,所述聚硅氧烷链键合有至少一种含有至少一个活性氢原子的聚醚链和含有至少一个烯属双键的聚醚链。
Description
本发明涉及包含颗粒的聚醚醇、其制备及其用途,尤其是用于制备聚氨酯的用途,优选用于制备硬质聚氨酯泡沫的用途。
包含颗粒的多元醇是长期已知的并广泛用于制备聚氨酯。一种通常使用的包含颗粒的多元醇的变型是接枝多元醇。所述接枝多元醇通常通过烯属不饱和单体在多元醇(称为载体多元醇)中原位聚合来制备。所述聚合通常在常常称作大分子单体的确保颗粒在多元醇中稳定分散的化合物的存在下进行。
如上所述,接枝多元醇用于制备聚氨酯。在此,一个重要的方面是制备硬质聚氨酯泡沫。
接枝多元醇是长期已知的并广泛记载于文献中。其通常通过如下方式制备:多异氰酸酯与含有至少两个对异氰酸酯基团呈活性的氢原子的化合物反应,所述化合物尤其是多官能醇。硬质聚氨酯泡沫优选用于制冷装置中的绝热或用于建筑构件。
改善硬质聚氨酯泡沫的性能是一个持续的目标。具体而言,应改善热导率和脱模时间,并且始终应确保用于硬质聚氨酯泡沫的形成组分的加工性,尤其是与发泡剂的相容性。
现已发现,使用通过烯属不饱和单体——尤其是苯乙烯和丙烯腈——原位聚合制备的含有聚合物颗粒的聚醚醇可改善硬质聚氨酯泡沫从模具中移出的性能。这类多元醇在工业上通常也称为接枝多元醇。
因此,WO2004/035650描述了一种使用接枝多元醇制备硬质聚氨酯泡沫的方法。此处所述的接枝多元醇使用2-8官能的聚醚醇与苯乙烯和丙烯腈(优选地以2:1的重量比)来制备,并且与其他多元醇混合而用于制备硬质聚氨酯泡沫,所述其他多元醇例如基于糖的多元醇和基于芳族胺的多元醇,例如甲苯二胺。此处所述的硬质泡沫表现出良好的固化性和脱模性以及良好的流动性能。然而,缺点是,所述接枝多元醇与多元醇和发泡剂的混溶性并不令人满意,以及多元醇组分——尤其是在使用烃时——的储存稳定性差。
WO2005/097863描述了一种使用接枝多元醇制备硬质聚氨酯泡沫的方法,所述接枝多元醇使用链中含有高比例的环氧乙烷的聚醚醇来制备。据记载,这能够改善与配方中的多元醇的相容性。
EP1108514描述了一种制备硬质泡沫板的方法,其中使用接枝多元醇。所述接枝多元醇使用含有聚醚醇的多元醇混合物来制备,所述聚醚醇的环氧乙烷含量为至少40重量%。据记载,这些泡沫表现出降低的收缩率。
JP2000169541描述了具有改进的机械强度和低收缩率的硬质聚氨酯泡沫。所述硬质聚氨酯泡沫使用接枝多元醇来制备,所述接枝多元醇仅用丙烯腈作为单体制备。
JP11060651也描述了一种使用接枝多元醇制备硬质聚氨酯泡沫的方法,所述接枝多元醇使用环氧乙烷含量为至少40重量%的聚醚醇来制备。
但是,在接枝多元醇中如此大量使用环氧乙烷也存在缺点。因此,通常用作发泡剂的烃在这类多元醇中的溶解度较差。此外,这类多元醇具有增强的本体活性。这降低了借助催化剂控制聚氨酯形成的可能性。
尤其在使用通过蔗糖引发的多元醇时,出现严重的接枝多元醇混溶性的问题。
本发明的目的是提供表现出高多元醇组分相容性并且使用低粘度多元醇组分的聚氨酯,尤其是硬质聚氨酯泡沫。所得的硬质泡沫应当表现出短脱模时间、低热导率以及良好的机械性能。
令人吃惊的是,该目的能够通过以下方式实现:一种特定的含有颗粒的聚醚醇(在下文中也称为接枝多元醇)及其用于制备聚氨酯的用途,尤其是用于制备硬质聚氨酯泡沫的用途。
因此,本发明提供可通过烯属不饱和单体在聚醚醇中原位聚合来制备的包含颗粒的聚醚醇,其中所述聚合在至少一种含有聚硅氧烷链的化合物(A)的存在下进行,所述聚硅氧烷链键合有至少一种含有至少一个反应性氢原子的聚醚链和含有至少一个烯属双键的聚醚链。
本发明还提供一种通过烯属不饱和单体在聚醚醇中原位聚合来制备包含颗粒的聚醚醇的方法,其中所述聚合在至少一种含有聚硅氧烷链的化合物(A)的存在下进行,所述聚硅氧烷链键合有至少一种含有至少一个 活性氢原子的聚醚链和至少一种含有至少一个烯属双键的聚醚链。
本发明还提供一种制备聚氨酯、尤其是制备硬质聚氨酯泡沫的方法,所述方法通过如下物质的反应进行
a)多异氰酸酯与
b)含有至少两个对异氰酸酯基团呈活性的氢原子的化合物,
其中组分b)包含至少一种本发明的包含颗粒的聚醚醇b1)。
所述包含颗粒的聚醚醇b1)优选地包含具有通式(I)的化合物(A)
其中
其中,A、B和C无规则排列,并且选择x、y和z以使聚硅氧烷链的分子量与总分子量的重量比为0.25至0.65,
Me为甲基基团,
R为含有1至10个碳原子的烷基基团,
M为含有2至10个碳原子的亚烷基或亚芳基基团或芳代脂族 基团(araliphaticgroup),其可经由醚键、酯键、氨基甲酸酯键、碳酸酯键或缩醛键键合至聚醚链,
m、n 为整数,对其进行选择以使单元A和C的分子量Mn在500至2000的范围内并且n:m在25:75至75:25的范围内,
其中,所述聚硅氧烷链
具有在3000至7000范围内的分子量Mn。
优选地,所述聚硅氧烷链具有2000至4500的分子量Mn。
包含颗粒的聚醚醇优选地包含具有通式(II)的化合物(A),
其中,变量Me和m、n、x、y和z具有与式(I)中相同的含义。
优选地,化合物(A)在分子中具有0.7至1个基团C,尤其是0.85至0.95个基团C。
一般而言,化合物(A)具有在8000至30000范围内的分子量Mn。
具体而言,化合物(A)具有10000至20000的分子量Mn。
在一个优选的实施方案中,在每两个单元A和/或C之间平均具有7至20个单元B。
优选地选择m和n以使单元A和C的分子量Mn平均在700至2000的范围内。
接枝多元醇b1)优选地具有至少35重量%的聚合颗粒的含量,所述聚合颗粒的含量也称为固体含量,基于所述接枝多元醇的重量计。所述固体含量通常应不超过65重量%,否则多元醇的粘度上升过大,因而会在加工中出现问题。
本发明接枝多元醇b1)的羟值优选地为40至260mg KOH/g,尤其是40至150mg KOH/g。
化合物(A)的制备可例如按以下步骤进行:在第一步中,在三氟甲磺酸的存在下,借助六甲基二硅氧烷(HMDS)、八甲基二硅氧烷(OMTS)和多甲基氢硅氧烷(PMHS)的平衡反应而制备聚硅氧烷骨架。此处发生OMTS的开环和PMHS的解聚。HMDS与形成的低聚物反应并且在此情况下产生端基。在第二步中,烯丙基醇借助环氧乙烷和/或环氧丙烷烷氧基化,以制备烯丙基聚醚醇。在第三步中,发生烯丙基聚醚醇的烯丙基基团的铂催化的氢化硅烷化,以形成聚醚硅氧烷。此处,Si-C键通过烯丙基聚醚醇的烯丙基基团的双键插入聚硅氧烷的Si-H键而形成。通常,使用1.5当量的烯丙基聚醚醇。在第四步中,聚醚硅氧烷例如与二甲基间异丙基苄基异氰酸酯(TMI)或类似化合物反应。此处,具有可聚合的双键的基团例如二甲基间异丙烯基苄基基团插入聚合物以形成氨基甲酸酯基团。合成步骤可在80℃下进行。此处优选使用亚化学计量量的TMI,以使平均每分子聚醚硅氧烷少于一个OH基团与TMI反应。化学计量比例的选择使变量x、y、z、n和m以目标方式设置。
本发明的接枝多元醇b1)通常通过在至少一种化合物(A)的存在下烯属不饱和单体在聚醚醇(下文中也称为载体多元醇)中原位聚合而制备。化合物(A)在下文中也称为大分子单体。
优选地使用的烯属不饱和单体为苯乙烯和/或丙烯腈。
化合物(A)的分子的疏水性组分(聚硅氧烷链)的分子量与总分子量的比例h为0.25至0.65。
对于载体多元醇,优选使用官能度为2至4、尤其是3至4的多元醇。所述载体多元醇通常通过环氧烷烃加成至H官能起始物质来制备,所述环氧烷烃尤其是环氧丙烷或包含基于聚醚醇b1i)的重量计至多20重量%环氧乙烷的环氧丙烷与环氧乙烷的混合物。所述起始物质通常为具有合适的官能度的醇或胺。优选地使用的起始物质为乙二醇、丙二醇、丙三醇、三羟甲基丙烷、乙二胺和甲苯二胺(TDA)。在本发明的一个特别优选的实施方案中,使用TDA、优选邻位异构体作为起始物质。
载体多元醇优选具有大于100mg KOH/g的羟值,特别优选在100至300mg KOH/g范围内、尤其是100至260mg KOH/g的羟值。
载体多元醇通过常规和已知的聚醚醇的制备方法来制备,所述方法在下文中更详细地描述。
载体多元醇优选单独使用,但还可以彼此任意混合的混合物形式使用。
在优选使用TDA的情况下,优选使用环氧乙烷和环氧丙烷的混合物作为环氧烷烃,优选首先加成环氧乙烷然后加成环氧丙烷,并且环氧乙烷的加成反应优选在不存在催化剂下进行。
在自由基聚合期间,化合物A并入共聚物链中。结果是形成具有聚醚嵌段和聚丙烯腈-苯乙烯嵌段的嵌段共聚物,所述嵌段共聚物充当连续相和分散相界面间的相增容剂并且抑制接枝多元醇颗粒的聚集。化合物A的比例通常为1至20重量%、特别优选1至15重量%,基于用于制备接枝多元醇的单体的总重量计。
缓和剂,也称为链转移剂,通常用于制备接枝多元醇。所述缓和剂的用途和功能描述于例如US4689354中。所述缓和剂影响增长中的自由基的链转移,从而降低形成的共聚物的分子量,结果是降低聚合物分子之间的交联,这可影响接枝多元醇的粘度和分散稳定性以及过滤性。缓和剂的比例通常为0.5至25重量%,基于用于制备接枝多元醇的单体的总重量计。通常用于制备接枝多元醇的缓和剂为醇,例如1-丁醇、2-丁醇、异丙醇、乙醇、甲醇、环己烷、甲苯;硫醇,例如乙硫醇、1-庚硫醇、2-辛硫 醇、1-十二硫醇、苯硫酚、巯基乙酸2-乙基己基酯、巯基乙酸甲酯、环己基硫醇;以及烯醇醚化合物、吗啉和α-(苯甲酰基氧基)苯乙烯。
自由基聚合通常使用过氧化物或偶氮化合物引发,例如过氧化二苯甲酰、过氧化月桂酰、过氧基-2-乙基己酸叔戊酯、过氧化二叔丁基、过氧化碳酸二异丙酯、过氧基-2-乙基己酸叔丁酯、过氧化新戊酸叔丁酯(t-butyl perpivalate)、过氧化新癸酸叔丁酯(t-butyl perneodecanoate)、过氧化苯甲酸叔丁酯(t-butyl perbenzoate)、过氧化丁烯酸叔丁酯(t-butylpercrotonate)、过氧化异丁酸叔丁酯(t-butyl perisobutyrate)、过氧基-1-甲基丙酸叔丁酯、过氧基-2-乙基戊酸叔丁酯、过氧基辛酸叔丁酯和过氧化邻苯二甲酸二叔丁酯(di-t-butyl perphthalate)、2,2’-偶氮双(2,4-二甲基戊腈)、2,2’-偶氮双异丁腈(AIBN)、2,2’-偶氮双异丁酸二甲酯、2,2’-偶氮双(2-甲基丁腈)(AMBN)、1,1’-偶氮双(1-环己腈)。引发剂的比例通常为0.1至6重量%,基于用于制备接枝多元醇的单体的总重量计。
由于单体的反应速率和引发剂的半衰期(half-life),用于制备接枝多元醇的自由基聚合通常在70至150℃的温度和最高达20巴的压力下进行。制备接枝多元醇的优选的反应条件为80至140℃的温度和大气压力至15巴的压力。
接枝多元醇b1)优选具有0.1μm至8μm、优选0.2μm至4μm的聚合物粒径,最大粒径为0.2至3μm、优选0.2至2μm。
在接枝多元醇b1)的进一步优选的实施方案中,粒径分布呈双峰,即粒径分布曲线具有两个最大值。这类接枝多元醇可例如通过将具有单峰粒径分布和不同粒径的接枝多元醇以合适的比例混合来制备,还可通过在该反应的初始进料中使用已包含烯属不饱和单体的聚合物的多元醇作为载体多元醇来制备。在该实施方案中,粒径也在上文所述的范围内。
接枝多元醇b1)可用连续法和分批法制备。通过这两种方法合成接枝多元醇是已知的并且描述于许多实例中。例如,通过半分批法合成接枝多元醇描述于例如EP439755中。例如,如EP510533中所描述的,一种特定形式的半分批法为半分批种子法(semi-batchseed process),其中接枝多元醇另外还用作该反应初始进料中的种子。通过连续法合成接枝多元醇同样是已知的并且尤其描述于WO00/59971中。
如上所述,本发明的接枝多元醇优选用于制备聚氨酯,尤其是用于制 备硬质聚氨酯泡沫。
所述聚氨酯通过常规和已知的方法通过多元醇b)与异氰酸酯a)反应制备,所述多元醇b)包含至少一种本发明的接枝多元醇(在下文中称为多元醇b1))。
接枝多元醇b1)原则上可作为唯一的含有至少两个对异氰酸酯基团呈活性的氢原子的化合物b)使用。然而,优选所述化合物b1)与其他含有至少两个对异氰酸酯基团呈活性的氢原子的化合物混合使用。
为此,可优选使用常规和已知的含有至少两个对异氰酸酯基团呈活性的氢原子的化合物。优选使用聚醚醇和/或聚酯醇与接枝多元醇b1)结合。
与接枝多元醇b1)一起使用的聚酯醇通常通过将多官能醇与多官能羧酸缩合制备,所述多官能醇(优选二醇)含有2至12的碳原子、优选2至6个碳原子;所述多官能羧酸含有2至12个碳原子,例如琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二羧酸(decanedicarboxylic acid)、马来酸、富马酸,并且优选邻苯二甲酸、间苯二甲酸、对苯二甲酸和同分异构的萘二羧酸。
与接枝多元醇b1)一起使用的聚醚醇通常具有2至8、尤其是3至8的官能度。
具体而言,使用通过已知方法制备的聚醚醇,例如通过环氧烷烃在催化剂、优选碱金属氢氧化物的存在下的阴离子聚合制备的聚醚醇。
对于环氧烷烃,通常使用环氧乙烷和/或环氧丙烷、优选纯的1,2-环氧丙烷。
对于起始分子,尤其是使用分子中含有至少3个、优选4至8个羟基基团或至少两个伯氨基基团的化合物。
对于分子中含有至少3个、优选4至8个羟基基团的起始分子,优选使用三羟甲基丙烷;丙三醇;季戊四醇;糖化合物,例如葡萄糖、山梨糖醇、甘露糖醇和蔗糖;多元酚;酚醛树脂,例如酚和甲醛的低聚缩合产物以及酚、甲醛、二烷醇胺和三聚氰胺的曼尼希(Mannich)缩合产物。
对于分子中含有至少两个伯氨基基团的起始分子,优选使用芳族二胺和/或多胺,例如亚苯基二胺、2,3-甲苯二胺、2,4-甲苯二胺、3,4-甲苯二胺和2,6-甲苯二胺(TDA)且尤其是其2,3-异构体和3,4-异构体,和4,4’-二氨基二苯基甲烷、2,4’-二氨基二苯基甲烷和2,2’-二氨基二苯基甲烷; 以及脂族二胺和多胺,例如乙二胺。
聚醚醇的官能度优选为3至8,且羟值优选为100mg KOH/g至1200mg KOH/g、尤其是240mg KOH/g至570mg KOH/g。
在本发明方法的一个优选的实施方案中,使用接枝多元醇b1)、蔗糖起始的聚醚醇b2)的混合物作为含有至少两个对异氰酸酯基团呈活性的氢原子的化合物。特别优选地另外使用由三官能醇或芳族胺起始的聚醚醇b3)。
聚醚醇b2)优选具有在375至525mg KOH/g范围内的羟值和5至7.5的官能度。蔗糖通常以与水和/或其他在室温下呈液态的双官能和三官能醇如乙二醇、丙二醇和/或丙三醇的混合物与环氧烷烃、优选环氧丙烷和/或环氧乙烷反应。该反应可借助碱金属或碱土金属氢氧化物或胺催化。
聚醚醇b3)优选具有在100至250mg KOH/g范围内的羟值和3至4的官能度。对于三官能醇,优选使用丙三醇或三羟甲基丙烷。对于芳族胺,优选使用TDA,特别优选使用其2,3-异构体和3,4-异构体。
在本发明的该实施方案中,组分b)包含10至25重量%的组分b1),25至65重量%的蔗糖起始的聚醚醇b2)和10-40重量%的由芳族胺起始的聚醚醇b3)或由三元醇起始的聚醚醇b3)。
关于用于本发明方法的其他起始材料,提供以下细节:
对于有机多异氰酸酯a),优选芳族多官能的异氰酸酯。
具体实例为:甲苯2,4-二异氰酸酯和甲苯2,6-二异氰酸酯(TDI)及相应的异构体混合物;二苯基甲烷4,4’-二异氰酸酯、二苯基甲烷2,4’-二异氰酸酯和二苯基甲烷2,2’-二异氰酸酯(MDI)和相应的异构体混合物;二苯基甲烷4,4’-二异氰酸酯和二苯基甲烷2,4’-二异氰酸酯的混合物;多苯基多亚甲基多异氰酸酯;二苯基甲基4,4’-二异氰酸酯、二苯基甲基2,4’-二异氰酸酯和二苯基甲基2,2’-二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(粗MDI);以及粗MDI和甲苯二异氰酸酯的混合物。有机二异氰酸酯和多异氰酸酯可单独地或以混合物的形式使用。
通常还使用改性的多官能的异氰酸酯,即由有机二异氰酸酯和/或多异氰酸酯的化学反应获得的产物。可提及的实例为含有异氰脲酸酯基团和/或氨基甲酸酯基团的二异氰酸酯和/或多异氰酸酯。改性的多异氰酸酯可任选地彼此混合或与未改性的有机多异氰酸酯混合,所述未改性的有机多 异氰酸酯例如二苯基甲烷2,4’-二异氰酸酯、二苯基甲烷4,4’-二异氰酸酯、粗MDI、甲苯2,4-二苯基甲烷和/或甲苯2,6-二异氰酸酯。
此外,还可使用多官能异氰酸酯与多元醇的反应产物及其与其他二异氰酸酯和多异氰酸酯的混合物。
现已发现,特别有用的是,NCO含量为29至33重量%且25℃下的粘度在150至1000mPa·s范围内的粗MDI作为有机多异氰酸酯。
可替换多元醇b2)和b3)或与多元醇b2)和b3)结合使用的其他多元醇如上所述。
含有至少两个对异氰酸酯呈活性的氢原子的化合物b)还包含可任选地伴随使用的扩链剂和交联剂。聚氨酯泡沫可使用或不使用扩链剂和/或交联剂而制备。加入双官能的扩链剂、三官能和更高官能的交联剂或任选地加入其混合物对于改进机械性能可能是有利的。对于扩链剂和/或交联剂,优选使用烷醇胺,尤其是分子量小于400、优选为60至300的二醇和/或三醇。
扩链剂、交联剂或其混合物有利地以1至20重量%、优选2至5重量%的量使用,基于含有至少两个对异氰酸酯基团呈活性的氢原子的组分b)计。
反应通常在催化剂、发泡剂和常规的助剂和/或添加剂的存在下进行。
具体而言,所用的催化剂为强烈加速异氰酸酯基团与对异氰酸酯基团呈活性的基团的反应的化合物。这类催化剂为强碱性胺,例如脂族仲胺、咪唑、脒和烷醇胺;或有机金属化合物,尤其是有机锡化合物。
当还将异氰脲酸酯基团并入硬质聚氨酯泡沫时,为此需要特定的催化剂。通常使用金属羧酸盐、尤其是乙酸钾及其溶液作为异氰脲酸酯催化剂。
根据需要,催化剂可单独使用或以彼此任意混合的混合物使用。
对于发泡剂,优选使用与异氰酸酯基团反应而释放二氧化碳的水。还可将物理发泡剂与水结合使用或替代水使用。所述物理发泡剂为对起始组分呈惰性并且通常在室温下呈液态且在氨基甲酸酯反应的条件下汽化的化合物。这些化合物的沸点优选低于50℃。物理发泡剂还包括在室温下呈气态并且在压力下引入至起始组分或溶解于起始组分的化合物,例如二氧化碳、低沸点烷烃和氟代烷烃。
所述化合物通常选自含有至少4个碳原子的烷烃和/或环烷烃、二烷 基醚、酯、酮、缩醛、含有1至8个碳原子的氟代烷烃以及在烷基链中含有1至3个碳原子的四烷基硅烷,尤其是四甲基硅烷。
可提及的实例为丙烷;正丁烷;异丁烷和环丁烷;正戊烷;异戊烷和环戊烷;环己烷;二甲醚;甲乙醚;甲基丁醚;甲酸甲酯;丙酮以及可在对流层中降解且因而不会破坏臭氧层的氟代烷烃,例如三氟甲烷、二氟甲烷、1,1,1,3,3-五氟丁烷、1,1,1,3,3-五氟丙烷、1,1,1,2-四氟乙烷、二氟乙烷和1,1,1,2,3,3,3-七氟丙烷;以及全氟烷烃,例如C3F8、C4F10、C5F12、C6F14和C7F17。上述物理发泡剂可单独使用或彼此的任意组合使用。
在本发明方法的一个优选的实施方案中,使用水与脂族烃的结合物作为发泡剂。优选的烃为正戊烷、异戊烷和环戊烷。
如果需要,本发明的方法可在阻燃剂以及常规助剂和/或添加剂的存在下进行。
对于阻燃剂,可使用有机磷酸酯和/或膦酸酯。优选使用对异氰酸酯基团没有活性的化合物。含氯磷酸酯还为优选的化合物之一。
这类阻燃剂的典型代表为磷酸三乙酯、磷酸二苯基甲苯酯、磷酸三(氯丙基)酯和乙烷膦酸二乙酯。
此外,还可使用含溴阻燃剂。对于含溴阻燃剂,优选使用含有对异氰酸酯基团呈活性的基团的化合物。这类化合物为四溴邻苯二甲酸与脂族二醇的酯和二溴丁烯二醇的烷氧基化产物。还可使用衍生自含有OH基团的溴化新戊基类化合物的化合物。
对于助剂和/或添加剂,使用对于此目的本身已知的材料,例如表面活性物质、泡沫稳定剂、孔调节剂、填料、颜料、染料、阻燃剂、水解抑制剂、抗静电剂、真菌抑制剂和细菌抑制剂。
关于用于实施本发明方法的起始原料、发泡剂、催化剂和助剂和/或添加剂的其他细节可见于例如Kunststoffhandbuch,第7卷,“Polyurethane,”Carl-Hanser-Verlag.Munich,第1版,1966,第2版,1983和第3版,1993中。
为了制备所述硬质聚氨酯泡沫,多异氰酸酯a)和含有至少两个对异氰酸酯基团呈活性的氢原子的化合物b)以如此的量反应以使异氰酸酯指数在100至220、优选115至195的范围内。所述硬质聚氨酯泡沫可借助已知的混合设备分批或连续制备。
多异氰脲酸酯泡沫的制备还可以更高的指数、优选最高达350的指数进行。
本发明的硬质PUR泡沫通常通过双组分法来制备。在该方法中,将含有至少两个对异氰酸酯基团呈活性的化合物b)与阻燃剂、催化剂c)、发泡剂d)及其他助剂和/或添加剂混合以形成多元醇组分,然后该多元醇组分与多异氰酸酯或多异氰酸酯与任选的发泡剂的混合物(也称为异氰酸酯组分)反应。
起始组分通常在15至35℃、优选20至30℃的温度下混合。可借助高压或低压计量仪器将反应混合物引入封闭的支撑工具中。例如,夹层元件就是通过该技术分批制造的。
还可将反应混合物自由倾倒或喷至表面上或倾倒或喷在中空空间内。屋顶或复杂的容器可通过该方法原位制备。还可将反应混合物同时在一处或在多处引入封闭的模具中,所述模具甚至具有复杂的几何结构。反应混合物的注入位置可位于模具的多个位置处。模具可以在空间方向上在反应混合物注入时间点有不同的排列。该方法例如为制备制冷设备的常规方法。同样可将反应混合物注入开放的模具,所述模具在完成填充操作之后关闭。该方法例如是制备制冷设备的门的常规方法。
为了制备夹层元件或绝热元件将异氰酸酯组分与多元醇组分在双传送带设备上连续混合也是本发明方法的一个优选实施方案。在该技术中,通常通过其他计量泵将催化剂和发泡剂计量加入多元醇组分中。此处,可将所用的组分分成最高达8个的单独组分。可以简单的方式在双组分法的基础上将发泡配方转化为多组分体系的加工。
通过本发明的方法制备的硬质聚氨酯泡沫可基于相稳定多元醇组分以非常短的脱模时间而制备,这使得显著缩短循环时间成为可能。尽管存在接枝多元醇,大量的物理发泡剂可溶于多元醇组分中,从而使该组分中的泡沫密度可达到小于30g/l。关于压缩强度、热导率和泡沫表面的品质/缩孔的形成方面的泡沫性能是优异的。
接枝多元醇的制备
以下实施例中所用的接枝多元醇以连续法和非连续法制备。通过这两种方法合成接枝多元醇是已知的并且描述于一系列实施例中。例如,通过 半分批法合成接枝多元醇描述于EP439755中。如EP510533中所描述的,一种特定形式的半分批法为半分批种子法,其中接枝多元醇另外还用作初始反应进料中的种子。具有双峰粒径分布的接枝多元醇的合成描述于WO03/078496。通过连续法合成接枝多元醇同样是已知的并且描述于例如WO00/59971中。
本发明借助如下实施例说明。
实施例
a)接枝多元醇的制备
为制备接枝多元醇,将载体多元醇、引发剂、缓和剂和10重量%的量的大分子单体投入装有搅拌器的反应器中,并将该混合物加热至100℃。随后连续地计量加入单体和90%的大分子单体。
在115℃下经过165分钟的反应时间之后,在10毫巴和125℃下在2小时的期间内蒸出未反应的单体。
缓和剂:1%的十二硫醇(基于单体的量计)
引发剂:0.45%的Wako V601
其他起始材料和接枝多元醇的性质示于表1中。
表1:接枝多元醇
表2:大分子单体
a | b | c | d | e | f | g | h | |
8 | 4400 | 7 | 980 | 8.6 | 81∶19 | 0.9 | 13000 | 0.34 |
20 | 5050 | 8.3 | 1700 | 8.4 | 60∶40 | 0.9 | 19000 | 0.27 |
27 | 5050 | 8.3 | 250 | 8.4 | 60∶40 | 0.9 | 16000 | 0.32 |
42 | 5050 | 10.6 | 980 | 6.5 | 60∶40 | 0.9 | 11000 | 0.46 |
如下定义涉及通式(I)
a-聚硅氧烷链(聚合物骨架)的分子量
b-支链之间的Si原子的平均数量
c-侧链的分子量
d-分子中支链的平均数量
e-侧链中环氧乙烷与环氧丙烷的比例
f-转化为末端C=C键的OH基团的平均个数
g-大分子单体(聚醚硅氧烷)的总分子量
h-两亲性(amphiphilicity),即分子的疏水性组分与总分子量的比例
硬质泡沫的制备(机械发泡)
将各种多元醇、稳定剂、催化剂与水和发泡剂以表3中所示的比例混合。将100重量份的多元醇组分与各自如表1中所示的量的二苯基甲烷二异氰酸酯与NCO含量为31.5重量%且粘度为200 mPas(25℃)的多亚苯基多亚甲基多异氰酸酯的混合物在HD 30高压发泡机(Elastogran GmbH)中混合。将该反应混合物注入尺寸为200 cm x 20 cm x 5cm或40 cm x 70 cm x 9 cm的模具中并使所述反应混合物在其中发泡。所得的泡沫的性能和特征数据示于表3中。
热导率根据DIN 52616测定。为制备试验样品,将所述聚氨酯反应混合物注入尺寸为200 x 20 x 5 cm3的模具中(10%过填充(overfilling)),几小时之后从中间切下尺寸为20 x 20 x 2 cm3的试验样品。
压缩强度根据DIN 53421/DIN EN ISO 604测定。
流动性为无量纲参数,并且为芯泡沫密度与自由发泡泡沫密度的比值。
表3泡沫
多元醇1:由邻TDA、环氧乙烷和环氧丙烷得到的聚醚醇,羟值为390mg KOH/g,25℃下粘度为17000mPa·s;
多元醇2:由蔗糖、丙三醇和环氧丙烷得到的聚醚醇,羟值为440mgKOH/g,25℃下粘度为2000mPa·s;
多元醇3:由邻TDA、环氧乙烷和环氧丙烷得到的聚醚醇,羟值为160mg KOH/g,25℃下粘度为800mPa·s;
接枝多元醇C1:基于多元醇3、10%大分子单体(山梨糖醇与环氧乙烷/环氧丙烷和TMI的反应产物,分子量为18000g/mol)、苯乙烯:丙烯腈为1:3的接枝多元醇,固体含量为45%,粒径为1微米;
接枝多元醇C2:基于多元醇3、15%大分子单体8、苯乙烯:丙烯腈为1:3的接枝多元醇,固体含量为35%,粒径为60微米;
接枝多元醇1:基于多元醇3、15%大分子单体20、苯乙烯:丙烯腈 为1:3的接枝多元醇,固体含量为35%,粒径为5微米;
接枝多元醇2:基于多元醇3、12%大分子单体27、苯乙烯:丙烯腈为1:3的接枝多元醇,固体含量为40%,粒径为0.8微米;
接枝多元醇3:基于多元醇3、12%大分子单体42、苯乙烯:丙烯腈为1:1的接枝多元醇,固体含量为40%,粒径为1.5微米;
稳定剂为Tegostab B8462(有机硅酮稳定剂)。
Claims (13)
1.一种包含颗粒的聚醚醇,其可通过烯属不饱和单体在聚醚醇中原位聚合来制备,其中所述聚合在至少一种含有聚硅氧烷链的化合物(A)的存在下进行,所述聚硅氧烷链键合有至少一种含有至少一个活性氢原子的聚醚链和至少一种含有至少一个烯属双键的聚醚链,
其中化合物(A)具有通式(I)
其中
其中,A、B和C无规则排列并且选择x、y和z以使聚硅氧烷链与总分子量的重量比为0.25至0.65,
Me为甲基基团,
R为含有1至10个碳原子的烷基基团,
M为含有2至10个碳原子的亚烷基或亚芳基基团或芳代脂族基团,其可经由醚键、酯键、氨基甲酸酯键、碳酸酯键或缩醛键键合至聚醚链,
m、n为整数,对其进行选择以使单元A和C的分子量Mn在500至2000的范围内并且n:m在20:80至80:20的范围内,
其中所述聚硅氧烷链
具有在3000至7000范围内的分子量Mn。
2.权利要求1的包含颗粒的聚醚醇,其中化合物(A)具有通式(II)
其中,变量Me和m、n、x、y和z具有与式(I)中相同的含义。
3.权利要求1的包含颗粒的聚醚醇,其中,化合物(A)在分子中具有0.7至1个基团C。
4.权利要求1的包含颗粒的聚醚醇,其中,化合物(A)具有8000至30 000的分子量Mn。
5.权利要求1的包含颗粒的聚醚醇,其中,化合物(A)中在每2个单元A和/或C之间平均具有7至20个单元B。
6.权利要求1的包含颗粒的聚醚醇,所述聚醚醇具有35重量%至65重量%的颗粒含量,基于所述包含颗粒的聚醚醇的重量计。
7.权利要求1的包含颗粒的聚醚醇,所述聚醚醇具有40至260mg KOH/g的羟值。
8.权利要求1的包含颗粒的聚醚醇,其中使用苯乙烯和/或丙烯腈作为烯属不饱和单体。
9.一种制备包含颗粒的聚醚醇的方法,其通过烯属不饱和单体在聚醚醇中原位聚合进行,其中所述聚合在至少一种含有聚硅氧烷链的化合物(A)的存在下进行,所述聚硅氧烷链键合有至少一种含有至少一个活性氢原子的聚醚链和至少一种含有至少一个烯属双键的聚醚链,并且其中化合物(A)具有通式(I)
其中
其中,A、B和C无规则排列并且选择x、y和z以使聚硅氧烷链与总分子量的重量比为0.25至0.65,
Me为甲基基团,
R为含有1至10个碳原子的烷基基团,
M为含有2至10个碳原子的亚烷基或亚芳基基团或芳代脂族基团,其可经由醚键、酯键、氨基甲酸酯键、碳酸酯键或缩醛键键合至聚醚链,
m、n为整数,对其进行选择以使单元A和C的分子量Mn在500至2000的范围内并且n:m在20:80至80:20的范围内,
其中所述聚硅氧烷链
具有在3000至7000范围内的分子量Mn。
10.一种制备聚氨酯的方法,所述方法通过如下物质的反应进行
a)多异氰酸酯与
b)含有至少两个对异氰酸酯基团呈反应性的氢原子的化合物,
其中组分b)包含至少一种权利要求1至8任一项的包含颗粒的聚醚醇b1)。
11.权利要求10的方法,其中包含颗粒的聚醚醇b1)以2至30重量%的量存在,基于组分b)的重量计。
12.一种可通过权利要求10的方法获得的聚氨酯。
13.权利要求1至8任一项所定义的包含颗粒的聚醚醇用于制备聚氨酯的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11178520.0 | 2011-08-23 | ||
EP11178520 | 2011-08-23 | ||
PCT/EP2012/066166 WO2013026815A1 (de) | 2011-08-23 | 2012-08-20 | Partikel enthaltende polyetheralkohole |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103890047A CN103890047A (zh) | 2014-06-25 |
CN103890047B true CN103890047B (zh) | 2016-10-19 |
Family
ID=46704660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201280051824.0A Expired - Fee Related CN103890047B (zh) | 2011-08-23 | 2012-08-20 | 包含颗粒的聚醚醇 |
Country Status (11)
Country | Link |
---|---|
EP (1) | EP2748233B1 (zh) |
JP (1) | JP6118321B2 (zh) |
KR (1) | KR101953416B1 (zh) |
CN (1) | CN103890047B (zh) |
AU (1) | AU2012298519B2 (zh) |
BR (1) | BR112014004187A2 (zh) |
HU (1) | HUE040688T2 (zh) |
MX (1) | MX360809B (zh) |
PL (1) | PL2748233T3 (zh) |
RU (1) | RU2615772C2 (zh) |
WO (1) | WO2013026815A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL2748232T3 (pl) * | 2011-08-23 | 2016-03-31 | Basf Se | Polieteroalkohole zawierające cząstki |
DE102013211349A1 (de) * | 2013-06-18 | 2014-12-18 | Evonik Industries Ag | Isocyanat-Siloxanpolyether-Zusammensetzung |
CN113831538B (zh) * | 2021-11-16 | 2023-08-11 | 南京美思德新材料有限公司 | 有机硅共聚物、其的制备方法、硬质泡沫稳定剂和硬质聚氨酯泡沫 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4723026A (en) * | 1984-04-24 | 1988-02-02 | Bp Chemicals Limited | Preparation of polymer polyols |
CN101389694A (zh) * | 2006-02-24 | 2009-03-18 | 路博润高级材料公司 | 可聚合的硅氧烷共聚醇大分子单体和由其制成的聚合物 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4689354A (en) | 1982-04-01 | 1987-08-25 | Basf Corporation | Process for the preparation of white graft polymer dispersions and flame-retardant polyurethane foams |
US4797501A (en) * | 1986-12-31 | 1989-01-10 | Union Carbide Corporation | Silicone-based stabilizers useful in the preparation of improved polyurethane foams |
ES2069664T3 (es) | 1990-01-29 | 1995-05-16 | Basf Corp | Un proceso para preparar polioles de injerto y los polioles preparados por el mismo. |
EP0510533A3 (en) | 1991-04-22 | 1993-05-26 | The Dow Chemical Company | Process for preparing polymer polyols, and polymer polyol so made |
DK0687279T3 (da) * | 1993-03-05 | 1999-02-01 | Shell Int Research | Polymerpolyoler |
US5447997A (en) * | 1994-03-11 | 1995-09-05 | General Electric Company | Silicone polyether carboxylic acids |
JP3837854B2 (ja) | 1997-08-08 | 2006-10-25 | 旭硝子株式会社 | ポリマー分散ポリオールの製造方法 |
JP2000169541A (ja) | 1998-12-04 | 2000-06-20 | Sanyo Chem Ind Ltd | ポリウレタンフォームの製造方法 |
JP4238481B2 (ja) | 1999-03-04 | 2009-03-18 | 旭硝子株式会社 | 断熱板体の製造方法およびポリオール組成物 |
US6172164B1 (en) | 1999-04-01 | 2001-01-09 | Basf Corporation | Process for making graft polyols using t-amyl peroxy free radical initiator |
ATE335030T1 (de) | 2002-03-15 | 2006-08-15 | Basf Ag | Graftpolyole mit bimodaler teilchengrössenverteilung und verfahren zur herstellung solcher graftpolyole sowie deren verwendung zur herstellung von polyurethanen |
ATE552285T1 (de) | 2002-10-15 | 2012-04-15 | Basf Se | Verfahren zur herstellung von polyurethan- hartschaumstoffen mit graftpolyolen |
DE102004017294A1 (de) * | 2004-04-05 | 2005-10-20 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Schaumstoffen |
RU2456306C1 (ru) * | 2005-12-16 | 2012-07-20 | ПиПиДжи ИНДАСТРИЗ ОГАЙО, ИНК. | Полиуретаны, изделия и покрытия, изготовленные из них, и способы их производства |
DE102008000266A1 (de) * | 2008-02-11 | 2009-08-13 | Evonik Goldschmidt Gmbh | Die Erfindung betrifft die Verwendung von Schaumstabilisatoren, die auf Basis nachwachsender Rohstoffe hergestellt werden, zur Herstellung von Polyurethanschäumen |
PL2748232T3 (pl) * | 2011-08-23 | 2016-03-31 | Basf Se | Polieteroalkohole zawierające cząstki |
-
2012
- 2012-08-20 KR KR1020147007115A patent/KR101953416B1/ko active IP Right Grant
- 2012-08-20 RU RU2014110880A patent/RU2615772C2/ru not_active IP Right Cessation
- 2012-08-20 MX MX2014002016A patent/MX360809B/es active IP Right Grant
- 2012-08-20 EP EP12748474.9A patent/EP2748233B1/de active Active
- 2012-08-20 AU AU2012298519A patent/AU2012298519B2/en not_active Ceased
- 2012-08-20 WO PCT/EP2012/066166 patent/WO2013026815A1/de active Application Filing
- 2012-08-20 BR BR112014004187A patent/BR112014004187A2/pt active Search and Examination
- 2012-08-20 CN CN201280051824.0A patent/CN103890047B/zh not_active Expired - Fee Related
- 2012-08-20 PL PL12748474T patent/PL2748233T3/pl unknown
- 2012-08-20 HU HUE12748474A patent/HUE040688T2/hu unknown
- 2012-08-20 JP JP2014526461A patent/JP6118321B2/ja active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4723026A (en) * | 1984-04-24 | 1988-02-02 | Bp Chemicals Limited | Preparation of polymer polyols |
CN101389694A (zh) * | 2006-02-24 | 2009-03-18 | 路博润高级材料公司 | 可聚合的硅氧烷共聚醇大分子单体和由其制成的聚合物 |
Also Published As
Publication number | Publication date |
---|---|
KR20140051432A (ko) | 2014-04-30 |
BR112014004187A2 (pt) | 2017-03-21 |
MX360809B (es) | 2018-11-16 |
HUE040688T2 (hu) | 2019-03-28 |
EP2748233B1 (de) | 2018-07-25 |
AU2012298519A1 (en) | 2014-04-03 |
EP2748233A1 (de) | 2014-07-02 |
CN103890047A (zh) | 2014-06-25 |
RU2014110880A (ru) | 2015-09-27 |
PL2748233T3 (pl) | 2019-02-28 |
MX2014002016A (es) | 2014-03-27 |
WO2013026815A1 (de) | 2013-02-28 |
KR101953416B1 (ko) | 2019-02-28 |
JP6118321B2 (ja) | 2017-04-19 |
RU2615772C2 (ru) | 2017-04-11 |
JP2014527109A (ja) | 2014-10-09 |
AU2012298519B2 (en) | 2015-08-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101425240B1 (ko) | 경질 폴리우레탄 발포체의 제조 방법 | |
WO2009142143A1 (ja) | 硬質ポリウレタンフォームの製造方法 | |
WO2011136230A1 (ja) | 硬質発泡合成樹脂の製造方法 | |
AU2014318647A1 (en) | PIPA based combustion-modified polyurethane foam | |
US20060058409A1 (en) | Method for producing rigid polyurethane foams by means of graft polyhydric alcohols | |
JP2014524500A (ja) | ポリウレタンの製造方法 | |
CN103890047B (zh) | 包含颗粒的聚醚醇 | |
US9403963B2 (en) | Particle-comprising polyether alcohols | |
AU2012299689B2 (en) | Polyether alcohols containing particles | |
CN109689723B (zh) | 多元醇组合物 | |
JP2014524493A (ja) | 硬質ポリウレタン発泡体の製造方法 | |
JP5407544B2 (ja) | ポリマー分散ポリオールの製造方法 | |
JP2013227491A (ja) | ポリマーポリオールの製造方法 | |
US20130046037A1 (en) | Process for producing rigid polyurethane foams | |
US20130217795A1 (en) | Particle-comprising polyether alcohols | |
JP2013227492A (ja) | ポリマーポリオールの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20161019 Termination date: 20200820 |
|
CF01 | Termination of patent right due to non-payment of annual fee |