DE10225943A1 - Verfahren zur Herstellung von Estern von Polyalkoholen - Google Patents

Info

Publication number

DE10225943A1

DE10225943A1 DE10225943A DE10225943A DE10225943A1 DE 10225943 A1 DE10225943 A1 DE 10225943A1 DE 10225943 A DE10225943 A DE 10225943A DE 10225943 A DE10225943 A DE 10225943A DE 10225943 A1 DE10225943 A1 DE 10225943A1

Authority

DE

Germany

Prior art keywords

reaction mixture

acid

polyalcohol

weight

independently

Prior art date

2002-06-11

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.)

Withdrawn

Links

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• 150000005846 sugar alcohols Polymers 0.000 title claims abstract description 73
• 238000000034 method Methods 0.000 title claims abstract description 72
• 230000008569 process Effects 0.000 title claims abstract description 23
• 150000002148 esters Chemical class 0.000 title claims description 49
• 238000002360 preparation method Methods 0.000 title claims description 7
• 239000011541 reaction mixture Substances 0.000 claims abstract description 81
• 230000032050 esterification Effects 0.000 claims abstract description 53
• 238000005886 esterification reaction Methods 0.000 claims abstract description 53
• 239000002253 acid Substances 0.000 claims abstract description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 83
• 239000000203 mixture Substances 0.000 claims description 79
• 229920000642 polymer Polymers 0.000 claims description 76
• 239000000017 hydrogel Substances 0.000 claims description 74
• -1 glycerol ethoxylated glycerol Chemical class 0.000 claims description 51
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 48
• 238000006243 chemical reaction Methods 0.000 claims description 39
• 239000002904 solvent Substances 0.000 claims description 38
• 239000000178 monomer Substances 0.000 claims description 33
• 238000004519 manufacturing process Methods 0.000 claims description 31
• 239000004971 Cross linker Substances 0.000 claims description 30
• 238000006116 polymerization reaction Methods 0.000 claims description 28
• 239000000126 substance Substances 0.000 claims description 28
• 150000001875 compounds Chemical class 0.000 claims description 25
• 238000004132 cross linking Methods 0.000 claims description 24
• 239000003054 catalyst Substances 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 229920005862 polyol Polymers 0.000 claims description 20
• 150000003077 polyols Chemical class 0.000 claims description 19
• 238000006386 neutralization reaction Methods 0.000 claims description 18
• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 17
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 16
• 239000003112 inhibitor Substances 0.000 claims description 16
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 16
• 239000007789 gas Substances 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 238000004821 distillation Methods 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 229920000058 polyacrylate Polymers 0.000 claims description 10
• 238000001035 drying Methods 0.000 claims description 8
• PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 7
• 239000000654 additive Substances 0.000 claims description 7
• 235000011187 glycerol Nutrition 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 6
• 230000006870 function Effects 0.000 claims description 6
• 150000002314 glycerols Chemical class 0.000 claims description 6
• 230000003472 neutralizing effect Effects 0.000 claims description 6
• 239000007858 starting material Substances 0.000 claims description 6
• 229920005628 alkoxylated polyol Polymers 0.000 claims description 5
• 230000015572 biosynthetic process Effects 0.000 claims description 5
• 239000011261 inert gas Substances 0.000 claims description 5
• WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 4
• TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
• 230000000996 additive effect Effects 0.000 claims description 4
• 239000002994 raw material Substances 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 239000004568 cement Substances 0.000 claims description 3
• 238000000227 grinding Methods 0.000 claims description 3
• 239000003999 initiator Substances 0.000 claims description 3
• 239000005022 packaging material Substances 0.000 claims description 3
• 239000003973 paint Substances 0.000 claims description 3
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• 239000006185 dispersion Substances 0.000 claims description 2
• 239000004745 nonwoven fabric Substances 0.000 claims description 2
• 238000007873 sieving Methods 0.000 claims 2
• 230000000379 polymerizing effect Effects 0.000 claims 1
• 150000007513 acids Chemical class 0.000 abstract description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 73
• 239000000835 fiber Substances 0.000 description 52
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 48
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 46
• 239000002250 absorbent Substances 0.000 description 40
• 239000000047 product Substances 0.000 description 40
• 230000002745 absorbent Effects 0.000 description 39
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 38
• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 38
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 31
• 239000007788 liquid Substances 0.000 description 31
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 30
• 239000003795 chemical substances by application Substances 0.000 description 27
• 239000002657 fibrous material Substances 0.000 description 24
• 239000000499 gel Substances 0.000 description 24
• NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 23
• 229920003043 Cellulose fiber Polymers 0.000 description 22
• 150000003254 radicals Chemical class 0.000 description 22
• 238000010521 absorption reaction Methods 0.000 description 21
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 238000010438 heat treatment Methods 0.000 description 18
• 238000005292 vacuum distillation Methods 0.000 description 18
• GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 15
• 229910052757 nitrogen Inorganic materials 0.000 description 15
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 229910052740 iodine Inorganic materials 0.000 description 14
• 239000011630 iodine Substances 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• 125000002947 alkylene group Chemical group 0.000 description 13
• 239000000243 solution Substances 0.000 description 13
• 229920002994 synthetic fiber Polymers 0.000 description 13
• 239000012209 synthetic fiber Substances 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• 239000002245 particle Substances 0.000 description 12
• 229920001169 thermoplastic Polymers 0.000 description 12
• 150000001298 alcohols Chemical class 0.000 description 11
• 229920000728 polyester Polymers 0.000 description 11
• 239000002585 base Substances 0.000 description 10
• 235000002639 sodium chloride Nutrition 0.000 description 10
• 239000004416 thermosoftening plastic Substances 0.000 description 10
• 229940113165 trimethylolpropane Drugs 0.000 description 10
• 238000005406 washing Methods 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 229920002678 cellulose Polymers 0.000 description 9
• 239000001913 cellulose Substances 0.000 description 9
• 229920003023 plastic Polymers 0.000 description 9
• 239000004033 plastic Substances 0.000 description 9
• 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 8
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
• 229920005372 Plexiglas® Polymers 0.000 description 8
• 125000001931 aliphatic group Chemical group 0.000 description 8
• 150000001735 carboxylic acids Chemical class 0.000 description 8
• LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• 150000002500 ions Chemical class 0.000 description 8
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
• 206010021639 Incontinence Diseases 0.000 description 7
• 239000004743 Polypropylene Substances 0.000 description 7
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
• 238000010533 azeotropic distillation Methods 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 239000010408 film Substances 0.000 description 7
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
• 229920001223 polyethylene glycol Polymers 0.000 description 7
• 229920001155 polypropylene Polymers 0.000 description 7
• 239000011148 porous material Substances 0.000 description 7
• QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
• 239000004698 Polyethylene Substances 0.000 description 6
• 239000002202 Polyethylene glycol Substances 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 125000004386 diacrylate group Chemical group 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 229940117969 neopentyl glycol Drugs 0.000 description 6
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 6
• 229920000573 polyethylene Polymers 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 150000003839 salts Chemical class 0.000 description 6
• 239000003381 stabilizer Substances 0.000 description 6
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• 239000004793 Polystyrene Substances 0.000 description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
• 244000269722 Thea sinensis Species 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 210000001124 body fluid Anatomy 0.000 description 5
• 239000010839 body fluid Substances 0.000 description 5
• 238000000576 coating method Methods 0.000 description 5
• 238000010276 construction Methods 0.000 description 5
• 238000007334 copolymerization reaction Methods 0.000 description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
• 239000011976 maleic acid Substances 0.000 description 5
• 239000011159 matrix material Substances 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 239000005020 polyethylene terephthalate Substances 0.000 description 5
• 229920002223 polystyrene Polymers 0.000 description 5
• 229960004063 propylene glycol Drugs 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 5
• 229920002554 vinyl polymer Polymers 0.000 description 5
• DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
• YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
• 229940035437 1,3-propanediol Drugs 0.000 description 4
• RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
• PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 4
• BXJGUBZTZWCMEX-UHFFFAOYSA-N 2,3-dimethylbenzene-1,4-diol Chemical compound CC1=C(C)C(O)=CC=C1O BXJGUBZTZWCMEX-UHFFFAOYSA-N 0.000 description 4
• ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 4
• PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 4
• HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
• 229920000297 Rayon Polymers 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
• 239000007983 Tris buffer Substances 0.000 description 4
• 230000002378 acidificating effect Effects 0.000 description 4
• 238000007792 addition Methods 0.000 description 4
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
• 229920005601 base polymer Polymers 0.000 description 4
• IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
• PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 238000009833 condensation Methods 0.000 description 4
• 230000005494 condensation Effects 0.000 description 4
• 229920001577 copolymer Polymers 0.000 description 4
• 239000003431 cross linking reagent Substances 0.000 description 4
• 238000009826 distribution Methods 0.000 description 4
• CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 4
• 235000012055 fruits and vegetables Nutrition 0.000 description 4
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
• JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 4
• 230000014759 maintenance of location Effects 0.000 description 4
• 235000013372 meat Nutrition 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
• 229920000098 polyolefin Polymers 0.000 description 4
• 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
• 239000002964 rayon Substances 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• NGSFWBMYFKHRBD-UHFFFAOYSA-M sodium lactate Chemical compound [Na+].CC(O)C([O-])=O NGSFWBMYFKHRBD-UHFFFAOYSA-M 0.000 description 4
• 230000006641 stabilisation Effects 0.000 description 4
• 238000011105 stabilization Methods 0.000 description 4
• 239000008107 starch Substances 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 238000003860 storage Methods 0.000 description 4
• KEQHJBNSCLWCAE-UHFFFAOYSA-N thymoquinone Chemical compound CC(C)C1=CC(=O)C(C)=CC1=O KEQHJBNSCLWCAE-UHFFFAOYSA-N 0.000 description 4
• CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
• 238000012546 transfer Methods 0.000 description 4
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
• JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
• 241000251468 Actinopterygii Species 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 229920001131 Pulp (paper) Polymers 0.000 description 3
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