JP2014522446A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014522446A5 JP2014522446A5 JP2014515904A JP2014515904A JP2014522446A5 JP 2014522446 A5 JP2014522446 A5 JP 2014522446A5 JP 2014515904 A JP2014515904 A JP 2014515904A JP 2014515904 A JP2014515904 A JP 2014515904A JP 2014522446 A5 JP2014522446 A5 JP 2014522446A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mixture
- oil
- glycol
- fatty acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 28
- 239000000203 mixture Substances 0.000 claims 24
- 150000002148 esters Chemical class 0.000 claims 10
- 239000006227 byproduct Substances 0.000 claims 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims 9
- 239000000194 fatty acid Substances 0.000 claims 9
- 229930195729 fatty acid Natural products 0.000 claims 9
- 239000000463 material Substances 0.000 claims 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 230000002209 hydrophobic effect Effects 0.000 claims 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 6
- 239000004970 Chain extender Substances 0.000 claims 5
- 150000008064 anhydrides Chemical class 0.000 claims 5
- 150000004665 fatty acids Chemical class 0.000 claims 5
- -1 tetraol Chemical class 0.000 claims 5
- 239000004971 Cross linker Substances 0.000 claims 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 238000004821 distillation Methods 0.000 claims 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 235000011187 glycerol Nutrition 0.000 claims 3
- 150000002902 organometallic compounds Chemical class 0.000 claims 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 3
- 229920005862 polyol Polymers 0.000 claims 3
- 150000003077 polyols Chemical class 0.000 claims 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical group OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 2
- 239000008157 edible vegetable oil Substances 0.000 claims 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000011261 inert gas Substances 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003921 oil Substances 0.000 claims 2
- 235000019198 oils Nutrition 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 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 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- PBWHJRFXUPLZDS-UHFFFAOYSA-N (1-Ethylpropyl)benzene Chemical compound CCC(CC)C1=CC=CC=C1 PBWHJRFXUPLZDS-UHFFFAOYSA-N 0.000 claims 1
- JIRHAGAOHOYLNO-UHFFFAOYSA-N (3-cyclopentyloxy-4-methoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC1CCCC1 JIRHAGAOHOYLNO-UHFFFAOYSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-N 2,3-dimethylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-N 0.000 claims 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims 1
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 239000010775 animal oil Substances 0.000 claims 1
- 239000006286 aqueous extract Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 239000003139 biocide Substances 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 239000004359 castor oil Substances 0.000 claims 1
- 235000019438 castor oil Nutrition 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 239000003240 coconut oil Substances 0.000 claims 1
- 235000019864 coconut oil Nutrition 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 claims 1
- 239000012975 dibutyltin dilaurate Substances 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 claims 1
- 239000004088 foaming agent Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 claims 1
- 239000000944 linseed oil Substances 0.000 claims 1
- 235000021388 linseed oil Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims 1
- 239000011785 micronutrient Substances 0.000 claims 1
- 235000013369 micronutrients Nutrition 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- 239000006259 organic additive Substances 0.000 claims 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004014 plasticizer Substances 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000003549 soybean oil Substances 0.000 claims 1
- 235000012424 soybean oil Nutrition 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 150000005846 sugar alcohols Chemical class 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000003784 tall oil Substances 0.000 claims 1
- 239000003760 tallow Substances 0.000 claims 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 1
- 239000008158 vegetable oil Substances 0.000 claims 1
- 239000001993 wax Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161496268P | 2011-06-13 | 2011-06-13 | |
| US61/496,268 | 2011-06-13 | ||
| US201161496868P | 2011-06-14 | 2011-06-14 | |
| US61/496,868 | 2011-06-14 | ||
| PCT/US2012/041951 WO2012173938A1 (en) | 2011-06-13 | 2012-06-11 | Aliphatic polyester polyols from cyclohexane oxidation byproduct streams as precursors for polyurethane and polyisocyanurate polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014522446A JP2014522446A (ja) | 2014-09-04 |
| JP2014522446A5 true JP2014522446A5 (enExample) | 2015-07-16 |
Family
ID=46321495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014515904A Pending JP2014522446A (ja) | 2011-06-13 | 2012-06-11 | ポリウレタンおよびポリイソシアヌレートポリマーのための前駆体としてのシクロヘキサン酸化副生成物ストリーム由来の脂肪族ポリエステルポリオール |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9056940B2 (enExample) |
| EP (1) | EP2718340B1 (enExample) |
| JP (1) | JP2014522446A (enExample) |
| KR (1) | KR20140039288A (enExample) |
| CN (1) | CN103732644B (enExample) |
| ES (1) | ES2643842T3 (enExample) |
| PL (1) | PL2718340T3 (enExample) |
| WO (1) | WO2012173938A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103732644B (zh) | 2011-06-13 | 2016-03-23 | 因温斯特技术公司 | 作为用于聚氨酯和聚异氰脲酸酯聚合物的前体的来自环己烷氧化副产物流的脂族聚酯多元醇 |
| KR20150013300A (ko) * | 2012-05-18 | 2015-02-04 | 바스프 에스이 | 분진 억제 응집체 |
| US20150274922A1 (en) * | 2012-09-21 | 2015-10-01 | Invista North America S.A.R.L. | Materials comprising nvr polyols |
| CA2891679C (en) | 2012-11-16 | 2021-10-26 | Basf Se | An encapsulated particle |
| CN103160236B (zh) * | 2013-04-17 | 2014-04-16 | 衡水前进油脂有限责任公司 | 一种利用植物油脂肪酸制备双组份彩钢板胶 |
| US9156745B2 (en) * | 2013-05-07 | 2015-10-13 | Koch Agronomic Services, Llc | Fertilizer granules having polymeric coating with organic carbonate |
| PL3004267T3 (pl) * | 2013-06-07 | 2020-02-28 | Swimc Llc | Uretanowa kompozycja powlekająca do podłoża metalowego |
| PL229712B1 (pl) * | 2014-04-01 | 2018-08-31 | Korzeniowski Waclaw Chemenergia | Sposób wytwarzania żywic poliestrowych |
| CN106660891A (zh) | 2014-04-28 | 2017-05-10 | 巴斯夫欧洲公司 | 形成包封肥料的方法 |
| WO2015189045A1 (en) * | 2014-06-11 | 2015-12-17 | Basf Se | Polyurethane compound for producing an integrated insulation component |
| CN104141231B (zh) * | 2014-08-02 | 2016-08-24 | 甄曰菊 | 一种织物涂层浆料及其制备方法 |
| JP6597039B2 (ja) * | 2015-08-11 | 2019-10-30 | 三菱ケミカル株式会社 | 接着剤、接着剤混合物及び木質ボード |
| US10563005B2 (en) | 2016-01-21 | 2020-02-18 | Invista North America S.A.R.L. | Aromatic polyester polyol compositions |
| CN111065501A (zh) * | 2017-08-23 | 2020-04-24 | 巴斯夫欧洲公司 | 在己内酰胺和己内酰胺低聚物存在下生产木质纤维素材料的方法 |
| CN107814909A (zh) * | 2017-11-13 | 2018-03-20 | 蒋艳玲 | 树脂板复合材料的制备方法 |
| WO2019117650A1 (ko) * | 2017-12-14 | 2019-06-20 | 주식회사 엘지화학 | 용출 제어형 비료 |
| KR102510340B1 (ko) | 2017-12-14 | 2023-03-15 | 주식회사 엘지화학 | 용출 제어형 비료 |
| CN108484313A (zh) * | 2018-02-06 | 2018-09-04 | 金华市众鑫农业科技有限公司 | 茶花专用缓释肥的制备方法 |
| JP7696837B2 (ja) * | 2019-06-05 | 2025-06-23 | オーエムエス インベストメンツ，インコーポレイテッド | 放出制御型肥料組成物 |
| CN111138659B (zh) * | 2020-01-14 | 2021-04-23 | 四川大学 | 一种非异氰酸酯路线制备三嵌段非离子型含氟短链表面活性剂的方法 |
| EP3851471A1 (en) | 2020-01-16 | 2021-07-21 | Purinowa spolka z o.o. | Method for obtaining high flame retardancy polyester polyols |
| CN111303373B (zh) * | 2020-02-25 | 2022-07-12 | 万华化学集团股份有限公司 | 一种低色度脲基甲酸酯组合物及其制备方法和应用 |
| US10919816B1 (en) | 2020-06-09 | 2021-02-16 | Surface Chemists Of Florida, Inc. | Epoxide moisture barrier coatings containing thermoplastic resins |
| US11193041B1 (en) * | 2020-06-09 | 2021-12-07 | Surface Chemists Of Florida, Inc. | Polyurethane moisture barrier coatings containing thermoplastic resins |
| US11180618B1 (en) * | 2020-08-05 | 2021-11-23 | Timeplast, Llc | Process of transforming a plastic extrusion system into a dynamic depolymerization reactor |
| CN111793380A (zh) * | 2020-08-25 | 2020-10-20 | 江苏冠军科技集团股份有限公司 | 一种含不参与光化学反应溶剂的涂料稀释剂及其制备方法和应用 |
| CN113512172B (zh) * | 2021-06-02 | 2022-02-22 | 茂施农业科技有限公司 | 一种聚氨酯控释肥包膜用的癸二酸副产脂肪酸聚酯多元醇 |
| CN114921162B (zh) * | 2021-07-20 | 2023-08-01 | 上海澳昌实业有限公司 | 一种水性透明耐磨阻燃罩面漆及其制备方法 |
| CN113817086B (zh) * | 2021-09-29 | 2022-11-11 | 韦尔通(厦门)科技股份有限公司 | 一种生物基光固化树脂组合物及其制备方法和应用 |
| CN118184933A (zh) | 2024-03-28 | 2024-06-14 | 茂施农业科技有限公司 | 一种含基于可再生原料的呋喃二甲酸的聚氨酯控释肥包膜材料及其应用和产品 |
| CN118374258B (zh) * | 2024-06-26 | 2024-10-29 | 上海京球新材料科技有限公司 | 一种胶粘剂及其制备方法 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3365490A (en) | 1966-08-05 | 1968-01-23 | Du Pont | Process for the production of dicarboxylic acids |
| PL93248B1 (enExample) * | 1975-05-02 | 1977-05-30 | ||
| US4166056A (en) * | 1978-04-13 | 1979-08-28 | Witco Chemical Corporation | Polyester plasticizer for vinyl resins derived from adipic acid process waste |
| US4233408A (en) * | 1979-05-07 | 1980-11-11 | Witco Chemical Corporation | Polyurethane foams from polyester precursor derived from adipic acid process waste |
| US4752637A (en) | 1984-08-15 | 1988-06-21 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US4609513A (en) | 1984-08-15 | 1986-09-02 | Jim Walter Research Corp. | Binder composition for manufacture of fiberboard |
| US5435821A (en) | 1985-12-12 | 1995-07-25 | Exxon Research & Engineering Co. | Controlled release vegetation enhancement agents coated with sulfonated polymers, method of production and prcesses of use |
| US4804403A (en) * | 1986-08-18 | 1989-02-14 | Melamine Chemicals, Inc. | Attrition-resistant, controlled release fertilizers |
| US4833182A (en) | 1986-09-29 | 1989-05-23 | Jim Walter Research Corp. | Isocyanate-polyester polyol binder for manufacture of cellulosic composites |
| US4898776A (en) | 1986-09-29 | 1990-02-06 | Jim Walter Reasearch Corp. | Isocyanate/surfactant-modified polyol binder for manufacture of lignocellulosic composites |
| PL151999B1 (pl) * | 1987-04-17 | 1990-10-31 | Sposób wytwarzania poliestroli | |
| PL162632B1 (pl) * | 1990-02-20 | 1993-12-31 | Politechnika Lodzka | Sposób wytwarzania oligoestroli PL |
| JP3082231B2 (ja) * | 1990-09-26 | 2000-08-28 | 大日本インキ化学工業株式会社 | 可塑剤及びそれを含むハロゲン含有樹脂組成物 |
| US5538531A (en) | 1991-06-24 | 1996-07-23 | Hudson; Alice P. | Controlled release fertilizers and methods of production |
| EP0606553A2 (en) * | 1993-01-11 | 1994-07-20 | Conoco Inc. | An ester base oil for lubricant compounds and process of making an ester base oil from an organic reaction by-product |
| US5374292A (en) | 1993-02-08 | 1994-12-20 | Pursell Industries | Machine system and process for producing attrition resistant slow release fertilizers |
| JPH0762180A (ja) * | 1993-08-20 | 1995-03-07 | Dainippon Ink & Chem Inc | 可塑剤及びそれを含むハロゲン含有樹脂組成物 |
| US5599374A (en) | 1994-09-23 | 1997-02-04 | Rlc Technologies, L.L.C. | Process for producing improved sulfur-coated urea slow release fertilizers |
| US5803946A (en) | 1996-06-20 | 1998-09-08 | Planet Polymer Technologies, Inc. | Controlled release plant nutrients |
| US5851261A (en) * | 1996-12-30 | 1998-12-22 | Bayer Corporation | Process for the production of polyurea encapsulated fertilizer particles and the encapsulated fertilizer particles produced by this process |
| US6338746B1 (en) | 1999-07-23 | 2002-01-15 | Rlc Technologies, L.L.C. | Polymer-sulfur-polymer coated fertilizers |
| US6663686B1 (en) | 2000-06-27 | 2003-12-16 | Agrium, Inc. | Controlled release fertilizer and method for production thereof |
| EP1172387A1 (en) | 2000-07-14 | 2002-01-16 | Huntsman International Llc | Process for preparing an elastomer |
| US6682751B1 (en) | 2001-09-12 | 2004-01-27 | Rlc Technologies, L.L.C. | Controlled-release pesticidal composition and method of making |
| US20040016276A1 (en) | 2002-07-26 | 2004-01-29 | Wynnyk Nick P. | Controlled release fertilizer having improved mechanical handling durability and method for production thereof |
| US20040020254A1 (en) | 2002-08-02 | 2004-02-05 | Agrium | Controlled release fertilizer and method for production thereof |
| US6703529B1 (en) | 2002-09-12 | 2004-03-09 | E. I. Du Pont De Nemours And Company | Process for oxidation of cyclohexane |
| US6995206B2 (en) | 2003-07-28 | 2006-02-07 | Hewlett-Packard Development Company, L.P. | Methods of preparing latex particulates with reactive functional groups |
| ATE487696T1 (de) | 2004-02-17 | 2010-11-15 | Chevron Phillips Chemical Co | Schwefelhaltige zusammensetzungen und verfahren zu deren herstellung |
| US7682656B2 (en) | 2004-06-14 | 2010-03-23 | Agruim Inc. | Process and apparatus for producing a coated product |
| US20060115586A1 (en) | 2004-11-30 | 2006-06-01 | Baozhong Xing | Process and apparatus for coating a controlled release product in a rotating drum |
| US7267707B2 (en) | 2005-03-30 | 2007-09-11 | Florikan E.S.A. Corp. | Polyurethane encapsulated fertilizer |
| JP2009504546A (ja) | 2005-08-09 | 2009-02-05 | アグリウム・インコーポレイテッド | コーティング添加剤としてエポキシ化脂肪酸トリグリセリドを用いる肥効調節型肥料 |
| US7818906B2 (en) | 2006-03-24 | 2010-10-26 | CCS digital—fabric GmbH | Lightbox |
| US20070231369A1 (en) | 2006-03-31 | 2007-10-04 | Rlc Technologies, L.L.C. | Ruminant feed composition and method of making |
| EP2134822A2 (en) * | 2007-04-09 | 2009-12-23 | Dow Global Technologies Inc. | Capped polyester polyol lubricant composition |
| PL2178811T3 (pl) * | 2007-08-13 | 2011-07-29 | Sumitomo Chemical Co | Granulka powlekana żywicą uretanową |
| US7771505B2 (en) | 2008-07-16 | 2010-08-10 | Agrium Inc. | Controlled release fertilizer composition |
| US20120101009A1 (en) | 2008-12-18 | 2012-04-26 | Invista North America S.A.R.L. | Cyclohexane oxidation process byproduct stream derivatives and methods for using the same |
| EP2384344B1 (en) * | 2009-01-30 | 2019-10-16 | INVISTA Textiles (U.K.) Limited | Aromatic polyesterpolyols, isocyanuratemodified polyurethane foams, and methods of making them |
| CN102388008B (zh) | 2009-04-08 | 2014-09-24 | 巴斯夫欧洲公司 | 通过氢化低聚酯和聚酯而生产1,6-己二醇的方法 |
| JP2012527519A (ja) * | 2009-05-19 | 2012-11-08 | インビスタ テクノロジーズ エス エイ アール エル | ポリオール組成物、樹脂混合組成物、噴霧組成物および各々の使用方法および各々の製造方法 |
| US8303680B2 (en) * | 2009-06-24 | 2012-11-06 | Basf Se | Encapsulated particle |
| CN103732644B (zh) | 2011-06-13 | 2016-03-23 | 因温斯特技术公司 | 作为用于聚氨酯和聚异氰脲酸酯聚合物的前体的来自环己烷氧化副产物流的脂族聚酯多元醇 |
-
2012
- 2012-06-11 CN CN201280039275.5A patent/CN103732644B/zh active Active
- 2012-06-11 JP JP2014515904A patent/JP2014522446A/ja active Pending
- 2012-06-11 KR KR1020147000832A patent/KR20140039288A/ko not_active Withdrawn
- 2012-06-11 WO PCT/US2012/041951 patent/WO2012173938A1/en not_active Ceased
- 2012-06-11 PL PL12728918T patent/PL2718340T3/pl unknown
- 2012-06-11 ES ES12728918.9T patent/ES2643842T3/es active Active
- 2012-06-11 US US13/493,840 patent/US9056940B2/en active Active
- 2012-06-11 EP EP12728918.9A patent/EP2718340B1/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014522446A5 (enExample) | ||
| KR101851554B1 (ko) | 중합체 가소제 조성물 | |
| JP2018508611A5 (enExample) | ||
| TW200909463A (en) | A process for the manufacture of natural oil hydroxylates | |
| Gandini | Polymers from plant oils | |
| RU2011131653A (ru) | Гиперразветвленные сложные полиэфиры и поликарбонаты в качестве деэмульгаторов для разрушения эмульсий сырой нефти | |
| CN1780808A (zh) | 由种子油制得的醛和醇组合物 | |
| KR101292675B1 (ko) | 바이오매스 유래 불포화 폴리에스테르의 제조방법 | |
| RU2014145022A (ru) | Высокофункциональные сложные полиэфирполиолы | |
| JP2018508611A (ja) | 熱可塑性ポリエステル、及び、リグニン又はタンニンからの高リサイクル含量であるポリオール | |
| JP2010514833A (ja) | グリセロールエステル | |
| CN102108194A (zh) | 一种聚乳酸/脂肪族二酸二醇聚酯组合物 | |
| CN105939991A (zh) | 酯化合物，包含其的增塑剂组合物，该组合物的制备方法和包含该增塑剂组合物的树脂组合物 | |
| Dizman et al. | Alkyd resins produced from bio-based resources for more sustainable and environmentally friendly coating applications | |
| JP6126138B2 (ja) | ポリウレタン用途のためのポリオール類の物質組成 | |
| CN105175697A (zh) | 一种植物油基聚酯增塑剂的制备方法 | |
| CN101775125A (zh) | 一种无芳香环结构聚六氢苯酐二元醇酯增塑剂及其制备方法 | |
| WO2011021107A2 (en) | Process for the preparation of glycerides | |
| KR20180128077A (ko) | 재생 가능하게 유도된 폴리에스터 그리고 이의 제조 방법 및 사용 방법 | |
| JP2010235777A (ja) | 不飽和ポリエステル樹脂 | |
| JPH10330470A (ja) | 脂肪酸変性ポリエステルポリオール組成物 | |
| Sankhyan et al. | Valorization of waste cooking oil: Emerging strategies for bio-based product development | |
| KR101193813B1 (ko) | 섬유 유연제용 양이온 화합물의 제조 방법 | |
| Malewska et al. | Brassica carinata and Camelina sativa oils as renewable raw materials for producing viscoelastic polyurethane foams | |
| RU2471768C2 (ru) | Способ утилизации глицеринсодержащего побочного продукта производства биодизельного топлива |