CA2527362A1

CA2527362A1 - (meth)acrylic ester for alkylenylene glycol and the use thereof

(meth)acrylic ester for alkylenylene glycol and the use thereof Download PDF

Info

Publication number: CA2527362A1
Authority: CA; Canada
Prior art keywords: weight; reaction mixture; equal; ester; meth
Prior art date: 2003-06-06
Legal status : Abandoned

Application number

CA002527362A

Other languages

English (en)

French (fr)

Inventor

Ulrich Riegel

Thomas Daniel

Matthias Weismantel

Mark Elliott

Rudiger Funk

Reinhold Schwalm

Current Assignee

BASF SE

Original Assignee

Individual

Priority date

2003-06-06

Filing date

2004-06-04

Publication date

2004-12-16

2003-06-06 Priority claimed from PCT/EP2003/005953 external-priority patent/WO2003104300A1/de

2003-12-11 Priority claimed from DE2003158369 external-priority patent/DE10358369A1/de

2004-06-04 Application filed by Individual filed Critical Individual

2004-12-16 Publication of CA2527362A1 publication Critical patent/CA2527362A1/en

Status Abandoned legal-status Critical Current

Links

LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 53
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 22
-1 acrylic ester Chemical class 0.000 title abstract description 43
239000011541 reaction mixture Substances 0.000 claims abstract description 76
150000002148 esters Chemical class 0.000 claims abstract description 61
238000004519 manufacturing process Methods 0.000 claims abstract description 23
239000000017 hydrogel Substances 0.000 claims description 81
229920000642 polymer Polymers 0.000 claims description 79
239000004971 Cross linker Substances 0.000 claims description 72
238000000034 method Methods 0.000 claims description 71
239000000203 mixture Substances 0.000 claims description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 68
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 56
230000008569 process Effects 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 45
238000005886 esterification reaction Methods 0.000 claims description 43
230000032050 esterification Effects 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 40
239000002253 acid Substances 0.000 claims description 30
239000000178 monomer Substances 0.000 claims description 30
239000003054 catalyst Substances 0.000 claims description 23
238000006116 polymerization reaction Methods 0.000 claims description 23
238000001035 drying Methods 0.000 claims description 18
239000012530 fluid Substances 0.000 claims description 18
239000003112 inhibitor Substances 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
238000004821 distillation Methods 0.000 claims description 12
229920000058 polyacrylate Polymers 0.000 claims description 10
150000002009 diols Chemical class 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
239000003999 initiator Substances 0.000 claims description 6
230000003472 neutralizing effect Effects 0.000 claims description 6
238000007873 sieving Methods 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
239000000654 additive Substances 0.000 claims description 5
230000000996 additive effect Effects 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
238000000227 grinding Methods 0.000 claims description 4
239000004568 cement Substances 0.000 claims description 3
239000005022 packaging material Substances 0.000 claims description 3
239000003973 paint Substances 0.000 claims description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
239000006185 dispersion Substances 0.000 claims description 2
239000004745 nonwoven fabric Substances 0.000 claims description 2
239000002994 raw material Substances 0.000 claims description 2
230000000379 polymerizing effect Effects 0.000 claims 2
150000002334 glycols Chemical class 0.000 abstract description 3
239000000835 fiber Substances 0.000 description 64
239000002250 absorbent Substances 0.000 description 37
230000002745 absorbent Effects 0.000 description 36
239000000499 gel Substances 0.000 description 33
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 30
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 25
239000002657 fibrous material Substances 0.000 description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
238000006386 neutralization reaction Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000010276 construction Methods 0.000 description 18
239000000463 material Substances 0.000 description 18
239000007789 gas Substances 0.000 description 17
238000004132 cross linking Methods 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000010438 heat treatment Methods 0.000 description 15
229920003043 Cellulose fiber Polymers 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
238000010521 absorption reaction Methods 0.000 description 14
230000002829 reductive effect Effects 0.000 description 14
239000000126 substance Substances 0.000 description 14
229920002994 synthetic fiber Polymers 0.000 description 14
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 13
239000002245 particle Substances 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
238000010626 work up procedure Methods 0.000 description 13
239000002585 base Substances 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 12
229920003023 plastic Polymers 0.000 description 12
239000004033 plastic Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
235000002639 sodium chloride Nutrition 0.000 description 12
239000012209 synthetic fiber Substances 0.000 description 12
229920001169 thermoplastic Polymers 0.000 description 12
238000007792 addition Methods 0.000 description 11
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000004416 thermosoftening plastic Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229920002678 cellulose Polymers 0.000 description 9
239000001913 cellulose Substances 0.000 description 9
235000010980 cellulose Nutrition 0.000 description 9
239000010408 film Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
229910052760 oxygen Inorganic materials 0.000 description 9
238000012856 packing Methods 0.000 description 9
229920000728 polyester Polymers 0.000 description 9
239000003381 stabilizer Substances 0.000 description 9
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 8
229920005372 Plexiglas® Polymers 0.000 description 8
239000004698 Polyethylene Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
238000001914 filtration Methods 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
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
229920000573 polyethylene Polymers 0.000 description 8
229920001223 polyethylene glycol Polymers 0.000 description 8
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 8
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
206010021639 Incontinence Diseases 0.000 description 7
239000002202 Polyethylene glycol Substances 0.000 description 7
229940048053 acrylate Drugs 0.000 description 7
125000004386 diacrylate group Chemical group 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
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 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
239000004743 Polypropylene Substances 0.000 description 6
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000012644 addition polymerization Methods 0.000 description 6
239000000853 adhesive Substances 0.000 description 6
230000001070 adhesive effect Effects 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
238000010533 azeotropic distillation Methods 0.000 description 6
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 6
229920001155 polypropylene Polymers 0.000 description 6
239000011148 porous material Substances 0.000 description 6
238000007127 saponification reaction Methods 0.000 description 6
QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001298 alcohols Chemical class 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
229920001577 copolymer Polymers 0.000 description 5
238000007334 copolymerization reaction Methods 0.000 description 5
239000012632 extractable Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
235000013372 meat Nutrition 0.000 description 5
239000005020 polyethylene terephthalate Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000010526 radical polymerization reaction Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000005507 spraying Methods 0.000 description 5
239000011732 tocopherol Substances 0.000 description 5
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
PGSWEKYNAOWQDF-UHFFFAOYSA-N 3-methylcatechol Chemical compound CC1=CC=CC(O)=C1O PGSWEKYNAOWQDF-UHFFFAOYSA-N 0.000 description 4
ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-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
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-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
229920002472 Starch Polymers 0.000 description 4
239000003708 ampul Substances 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
238000013461 design Methods 0.000 description 4
238000009826 distribution Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 4
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-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
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
229920000098 polyolefin Polymers 0.000 description 4
229920001451 polypropylene glycol Polymers 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002964 rayon Substances 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
KEQHJBNSCLWCAE-UHFFFAOYSA-N thymoquinone Chemical compound CC(C)C1=CC(=O)C(C)=CC1=O KEQHJBNSCLWCAE-UHFFFAOYSA-N 0.000 description 4
229960001295 tocopherol Drugs 0.000 description 4
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-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 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
241000196324 Embryophyta 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
239000004952 Polyamide Substances 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 3
238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
230000008859 change Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
235000012055 fruits and vegetables Nutrition 0.000 description 3
229920000578 graft copolymer Polymers 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
230000002209 hydrophobic effect Effects 0.000 description 3
230000000977 initiatory effect Effects 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
125000005499 phosphonyl group Chemical group 0.000 description 3
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
229920001515 polyalkylene glycol Polymers 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
229920000139 polyethylene terephthalate Polymers 0.000 description 3
238000003860 storage Methods 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000002699 waste material Substances 0.000 description 3
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
KDLIPGJLQQTGKY-UHFFFAOYSA-N 1-n,4-n-bis(2-methylpropyl)benzene-1,4-diamine Chemical compound CC(C)CNC1=CC=C(NCC(C)C)C=C1 KDLIPGJLQQTGKY-UHFFFAOYSA-N 0.000 description 2
PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 description 2
VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 2
OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 2
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