JP4357263B2 - 安息香酸デシルエステルの異性体混合物、その製法およびその使用 - Google Patents
安息香酸デシルエステルの異性体混合物、その製法およびその使用 Download PDFInfo
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- JP4357263B2 JP4357263B2 JP2003363384A JP2003363384A JP4357263B2 JP 4357263 B2 JP4357263 B2 JP 4357263B2 JP 2003363384 A JP2003363384 A JP 2003363384A JP 2003363384 A JP2003363384 A JP 2003363384A JP 4357263 B2 JP4357263 B2 JP 4357263B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- benzoic acid
- propyl
- methyl
- isopropyl
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 238000000034 method Methods 0.000 title claims abstract description 21
- CUSUFTNOPPMGBK-UHFFFAOYSA-N decyl benzoate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1 CUSUFTNOPPMGBK-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 230000008569 process Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 44
- -1 2-isopropyl-4-methylhexyl Chemical group 0.000 claims abstract description 31
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 23
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 10
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims abstract description 8
- OKGUXCUCCABSEP-UHFFFAOYSA-N 2-propylheptyl benzoate Chemical compound CCCCCC(CCC)COC(=O)C1=CC=CC=C1 OKGUXCUCCABSEP-UHFFFAOYSA-N 0.000 claims abstract description 7
- IUYAOMJLXVZNBR-UHFFFAOYSA-N (5-methyl-2-propylhexyl) benzoate Chemical compound CC(C)CCC(CCC)COC(=O)C1=CC=CC=C1 IUYAOMJLXVZNBR-UHFFFAOYSA-N 0.000 claims abstract description 6
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims abstract description 5
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims abstract description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 40
- 239000004014 plasticizer Substances 0.000 claims description 30
- 229920001944 Plastisol Polymers 0.000 claims description 28
- 239000004999 plastisol Substances 0.000 claims description 28
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 15
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- VZXWJVFQXZUFQS-UHFFFAOYSA-N 4-methyl-2-propylhexan-1-ol Chemical compound CCCC(CO)CC(C)CC VZXWJVFQXZUFQS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 7
- 235000011037 adipic acid Nutrition 0.000 claims description 7
- VHGVOODVCUKVCL-UHFFFAOYSA-N 4-methyl-2-propan-2-ylhexan-1-ol Chemical compound CCC(C)CC(CO)C(C)C VHGVOODVCUKVCL-UHFFFAOYSA-N 0.000 claims description 6
- SFIQHFBITUEIBP-UHFFFAOYSA-N 5-methyl-2-propan-2-ylhexan-1-ol Chemical compound CC(C)CCC(CO)C(C)C SFIQHFBITUEIBP-UHFFFAOYSA-N 0.000 claims description 6
- QEVWDMOIPOLQBL-UHFFFAOYSA-N 5-methyl-2-propylhexan-1-ol Chemical compound CCCC(CO)CCC(C)C QEVWDMOIPOLQBL-UHFFFAOYSA-N 0.000 claims description 6
- RCYYVUCLMJUKTJ-UHFFFAOYSA-N (4-methyl-2-propan-2-ylhexyl) benzoate Chemical compound CCC(C)CC(C(C)C)COC(=O)C1=CC=CC=C1 RCYYVUCLMJUKTJ-UHFFFAOYSA-N 0.000 claims description 5
- YVFQBNKESOCYDE-UHFFFAOYSA-N (5-methyl-2-propan-2-ylhexyl) benzoate Chemical compound CC(C)CCC(C(C)C)COC(=O)C1=CC=CC=C1 YVFQBNKESOCYDE-UHFFFAOYSA-N 0.000 claims description 5
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical class CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 5
- GEUVOKOZLUZEDG-UHFFFAOYSA-N (4-methyl-2-propylhexyl) benzoate Chemical compound CCC(C)CC(CCC)COC(=O)C1=CC=CC=C1 GEUVOKOZLUZEDG-UHFFFAOYSA-N 0.000 claims description 2
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical class C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 claims description 2
- TUOSWEIWIXJUAU-UHFFFAOYSA-N bis(7-methyloctyl) cyclohexane-1,1-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1(C(=O)OCCCCCCC(C)C)CCCCC1 TUOSWEIWIXJUAU-UHFFFAOYSA-N 0.000 claims description 2
- MSDBCXHVDKLCCF-UHFFFAOYSA-N 2,6-dimethyloctan-3-ol Chemical compound CCC(C)CCC(O)C(C)C MSDBCXHVDKLCCF-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 abstract description 9
- 238000005886 esterification reaction Methods 0.000 abstract description 9
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 abstract description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 20
- 238000005984 hydrogenation reaction Methods 0.000 description 18
- 239000004800 polyvinyl chloride Substances 0.000 description 18
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 17
- 229920000915 polyvinyl chloride Polymers 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000005259 measurement Methods 0.000 description 15
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 14
- 238000007037 hydroformylation reaction Methods 0.000 description 12
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 12
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 10
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 238000005882 aldol condensation reaction Methods 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 6
- 239000004440 Isodecyl alcohol Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- MMFCJPPRCYDLLZ-CMDGGOBGSA-N (2E)-dec-2-enal Chemical compound CCCCCCC\C=C\C=O MMFCJPPRCYDLLZ-CMDGGOBGSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- MMFCJPPRCYDLLZ-UHFFFAOYSA-N dec-2-enal Natural products CCCCCCCC=CC=O MMFCJPPRCYDLLZ-UHFFFAOYSA-N 0.000 description 5
- 125000005498 phthalate group Chemical class 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- HNDYULRADYGBDU-UHFFFAOYSA-N 8-methylnonyl benzoate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1 HNDYULRADYGBDU-UHFFFAOYSA-N 0.000 description 4
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- SZLIWAKTUJFFNX-UHFFFAOYSA-N dihydrocitronellol benzoate Natural products CC(C)CCCC(C)CCOC(=O)C1=CC=CC=C1 SZLIWAKTUJFFNX-UHFFFAOYSA-N 0.000 description 4
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000003349 gelling agent Substances 0.000 description 4
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 2
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- RKELNIPLHQEBJO-UHFFFAOYSA-N bis(5-methylhexyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC(C)C RKELNIPLHQEBJO-UHFFFAOYSA-N 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 150000003754 zirconium Chemical class 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 description 1
- RHVHKONOVNRWEJ-UHFFFAOYSA-N 2-(8-methylnonyl)benzoic acid Chemical compound CC(C)CCCCCCCC1=CC=CC=C1C(O)=O RHVHKONOVNRWEJ-UHFFFAOYSA-N 0.000 description 1
- UADWUILHKRXHMM-UHFFFAOYSA-N 2-ethylhexyl benzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1 UADWUILHKRXHMM-UHFFFAOYSA-N 0.000 description 1
- 229940106004 2-ethylhexyl benzoate Drugs 0.000 description 1
- OFQDRHPWHDWIOS-UHFFFAOYSA-N 2-methylbutanal 3-methylbutanal Chemical compound CCC(C)C=O.CC(C)CC=O OFQDRHPWHDWIOS-UHFFFAOYSA-N 0.000 description 1
- LNKHFECVVLVFFE-UHFFFAOYSA-N 2-nonoxycarbonylbenzoic acid Chemical class CCCCCCCCCOC(=O)C1=CC=CC=C1C(O)=O LNKHFECVVLVFFE-UHFFFAOYSA-N 0.000 description 1
- OIUGWVWLEGLAGH-UHFFFAOYSA-N 6-nonoxy-6-oxohexanoic acid Chemical class CCCCCCCCCOC(=O)CCCCC(O)=O OIUGWVWLEGLAGH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004439 Isononyl alcohol Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical group 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 150000008360 acrylonitriles Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UADWUILHKRXHMM-ZDUSSCGKSA-N benzoflex 181 Natural products CCCC[C@H](CC)COC(=O)C1=CC=CC=C1 UADWUILHKRXHMM-ZDUSSCGKSA-N 0.000 description 1
- MADOQDQYIBNUGE-UHFFFAOYSA-N benzoic acid;2-(2-hydroxypropoxy)propan-1-ol Chemical compound CC(O)COC(C)CO.OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 MADOQDQYIBNUGE-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- WWNGFHNQODFIEX-UHFFFAOYSA-N buta-1,3-diene;methyl 2-methylprop-2-enoate;styrene Chemical compound C=CC=C.COC(=O)C(C)=C.C=CC1=CC=CC=C1 WWNGFHNQODFIEX-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 238000013016 damping Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- KYZHGEFMXZOSJN-UHFFFAOYSA-N isobutyl benzoate Chemical class CC(C)COC(=O)C1=CC=CC=C1 KYZHGEFMXZOSJN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- QKNZNUNCDJZTCH-UHFFFAOYSA-N pentyl benzoate Chemical class CCCCCOC(=O)C1=CC=CC=C1 QKNZNUNCDJZTCH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 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
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
安息香酸−2−プロピルヘプチルエステル 50〜99%、有利に70〜99%、特に有利に85〜99%および
安息香酸−2−イソプロピル−4−メチル−ヘキシルエステルおよび/または安息香酸−2−イソプロピル−5−メチルヘキシルエステル、安息香酸−2−プロピル−4−メチルヘキシルエステル、安息香酸−2−プロピル−5−メチルヘキシルエステル 1〜50%、有利に1〜30%、特に有利に1〜15%
を含有する安息香酸デシルエステルの異性体混合物である。
a)C4−オレフィンまたはC4−オレフィン混合物をヒドロホルミル化して、相応するC5−アルデヒドにする工程、
b)a)で製造されたアルデヒドをアルドール縮合してデセナールにする工程、
c)工程b)で製造されたデセナールを水素化し、デカノールにする工程、
により行うことができる。
安息香酸−2−プロピルヘプチルエステル50〜99%および
安息香酸−2−イソプロピル−4−メチル−ヘキシルエステルおよび/または安息香酸−2−イソプロピル−5−メチルヘキシルエステル、安息香酸−2−プロピル−4−メチルヘキシルエステル、安息香酸−2−プロピル−5−メチルヘキシルエステル1〜50質量%を含有する安息香酸デシルエステルの異性体混合物を製造する方法にも関し、この方法は2−プロピルヘプタノール、2−イソプロピル−4−メチルヘキサノールおよび/または2−イソプロピル−5−メチルヘキサノール、2−プロピル−4−メチルヘキサノール、2−プロピル−5−メチルヘキサノールを安息香酸でエステル化することを特徴とする。
炭素原子4〜10個を有する同一または異なるアルキル基、特にn−ブチル基、n−ヘキシル基、n−オクチル基、イソノニル基および2−エチルヘキシル基をエステル基の酸素原子に結合して有するポリアクリレート、ポリメタクリレート、ポリメチルメタクリレート、メチルアクリレート−ブチルアクリレート−コポリマー、メチルメタクリレート−ブチルメタクリレート−コポリマー、エチレン−酢酸ビニル−コポリマー、塩素化ポリエチレン、ニトリルゴム、アクリロニトリル−ブタジエン−スチレン−コポリマー、エチレン−プロピレン−コポリマー、エチレン−プロピレン−ジエン−コポリマー、スチレン−アクリロニトリル−コポリマー、アクリロニトリル−ブタジエン−ゴム、スチレン−ブタジエン−エラストマー、メチルメタクリレート−スチレン−ブタジエン−コポリマーおよび/またはニトロセルロース。
2−プロピルヘプタノールおよび2−プロピル−4−メチル−ヘキサノールを文献公知の製法により製造する(1−ブテンのヒドロホルミル化、引き続き得られたアルデヒドのアルドール化およびデセナールの水素化)。2−プロピルヘプタノールの添加により、2−プロピルヘプタノール90質量%および2−プロピル−4−メチル−ヘキサノール10質量%の割合に調節する。
水分離器および還流冷却器を載置し、並びに試料採取用接続管および温度計を備える4 l蒸留フラスコ中に安息香酸976g(8モル)、例1からのイソデシル−アルコール混合物1872g(12モル)およびブチルチタネート0.59g(酸の量に対して0.06%)を秤量し、窒素雰囲気下に加熱沸騰させる。エステル化の際に生じた反応水を規則的に取り出した。酸価が約3時間後に0.1mgKOH/gを下回った時に、過剰のアルコールをラッシッヒリングが充填された10cmのカラムを介して蒸留した。その後、配合物を80℃に冷却し、浸漬撹拌機、載置した滴加ロートおよびカラムを備える4 l反応フラスコ中に移し替え、クライゼンブリッジに固定した。その後、5%の水酸化ナトリウム水溶液で中和した(約10倍の水酸化ナトリウム液の過剰)。引き続き、真空(10ミリバール)下に190℃に加熱した。次いで、滴加ロートを介して脱塩水8%(使用した原料エステル量に対して)を一定の温度で滴加する。水の添加後、ヒーターを止め、真空下に冷却する。
実質的にメチル基で分枝したC10−アルコール混合物の典型的な代表はExxal10である(ExxonMobil Chemical社のイソデシルアルコール混合物)。
処方AおよびB中にはそれぞれ両方の迅速にゲル化する可塑剤のみが代表とされていて、これらのタイプの間の差異がより強調して明らかにされる。処方CおよびDはVESTINOL9(OXENO Olefinchemie GmbH社のDINP)と迅速ゲル化剤とからなる実地に関連した混合物を典型的な上塗り塗料組成物中に含有した。
例4において製造したプラスチゾルの粘度の測定はDIN53019により、ソフトウェアUS200を介して制御されるRheometer Physica DSR 4000を用いて、次のように実施した。このプラスチゾルを貯蔵容器中でもう一回スパーテルで攪拌し、測定計Z3(DIN25mm)中で操作手引き書により測定した。この測定は25℃で自動的に前記ソフトウェアを介して行われる。次の点を制御した:
・ 60秒間の間100s−1での前剪断、この際測定値は記録しなかった
・ 200s−1で開始し、順に0.1s−1まで下方向への傾斜で、5秒間の測定期間で30工程で対数列に分割する。
プラスチゾルのゲル化挙動の実験は、剪断応力により制御されて作動する商標Bohlin CVO(測定システムPP20)の振動粘度計(Oszillationsviskosimeter)中で実施した。
モード: 温度傾斜
開始温度:25℃
最終温度:180℃
加熱/冷却速度:2℃/分
測定後の温度:25℃
振動周波数:2Hz
回復時間:1s
待ち時間:15s
連続的な振動:オン
自動的な剪断応力基準値:オン
開始剪断応力:0.3Pa
設定デフォーメーション:0.002
間隙幅:0.5mm
測定方法の実施:
測定システムプレート上にスパーテルで測定すべきプラスチゾル(例4からの処方CおよびD)液滴を気泡を有さないように担持した。その際測定システムを一緒にした後にプラスチゾルが均質にいくらか測定システムから流れ出すことができるように(周囲に約6mmを越えない)留意する。引き続き、断熱にも作用する保護カバーを載置し、測定を開始する。
可塑剤の添加によりPVCのガラス転移温度は、材料が低温でもなお可撓性である程度に低下する。ガラス転移温度TGを低下させる可塑剤の能力は、可塑剤として好適な物質のガラス転移温度が低いほど大である。
Claims (10)
- 安息香酸−2−プロピルヘプチルエステル 50〜99%および
安息香酸−2−イソプロピル−4−メチル−ヘキシルエステルおよび/または安息香酸−2−イソプロピル−5−メチル−ヘキシルエステル、安息香酸−2−プロピル−4−メチルヘキシルエステル、安息香酸−2−プロピル−5−メチルヘキシルエステル 1〜50%
を含有する安息香酸デシルエステルの異性体混合物からなる可塑剤。 - 請求項1に記載の安息香酸デシルエステルの異性体混合物5〜90質量%と、さらに
アルキル基が炭素原子4〜13個を含有するフタル酸ジアルキルエステル10〜95質量%を含有する、請求項1に記載の可塑剤。 - フタル酸ジアルキルエステルがフタル酸ジイソノニルエステルである、請求項2記載の可塑剤。
- 請求項1に記載の安息香酸デシルエステルの異性体混合物5〜90質量%と、さらに
アルキル基が炭素原子4〜13個を含有するアジピン酸ジアルキルエステル10〜95質量%を含有する、請求項1に記載の可塑剤。 - アジピン酸ジアルキルエステルがアジピン酸ジイソノニルエステルである、請求項4記載の可塑剤。
- 請求項1に記載の安息香酸デシルエステルの異性体混合物5〜90質量%と、さらに
アルキル基が炭素原子4〜13個を含有するシクロヘキサンジカルボン酸アルキルエステル10〜95質量%を含有する、請求項1に記載の可塑剤。 - シクロヘキサンジカルボンアルキルエステルがシクロヘキサンジカルボン酸ジイソノニルエステルである、請求項6記載の可塑剤。
- 安息香酸−2−プロピルヘプチルエステル50〜99%および安息香酸−2−イソプロピル−4−メチル−ヘキシルエステルおよび/または安息香酸−2−イソプロピル−5−メチル−ヘキシルエステル、安息香酸−2−プロピル−4−メチルヘキシルエステル、安息香酸−2−プロピル−5−メチルヘキシルエステル1〜50%を含有する安息香酸デシルエステルの異性体混合物からなる可塑剤を製造する方法において、2−プロピルヘプタノール、2−イソプロピル−4−メチル−ヘキサノールおよび/または2−イソプロピル−5−メチル−ヘキサノール、2−プロピル−4−メチルヘキサノール、2−プロピル−5−メチルヘキサノールを安息香酸でエステル化することを特徴とする、可塑剤の製法。
- 安息香酸−2−プロピルヘプチルエステル50〜99%および安息香酸−2−イソプロピル−4−メチル−ヘキシルエステルおよび/または安息香酸−2−イソプロピル−5−メチル−ヘキシルエステル、安息香酸−2−プロピル−4−メチルヘキシルエステル、安息香酸−2−プロピル−5−メチルヘキシルエステル1〜50質量%を含有する安息香酸デシルエステルの異性体混合物からなる可塑剤を製造する方法において、安息香酸メチルエステル、安息香酸エチルエステル、安息香酸プロピルエステル、安息香酸ブチルエステルを2−プロピルヘプタノール、2−イソプロピル−4−メチル−ヘキサノールおよび/または2−イソプロピル−5−メチル−ヘキサノール、2−プロピル−4−メチルヘキサノール、2−プロピル−5−メチルヘキサノールとエステル交換することを特徴とする、可塑剤の製法。
- PVC−プラスチゾルのために使用するための、請求項1から7までのいずれか1項記載の可塑剤。
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ATE318256T1 (de) | 2006-03-15 |
EP1415978A1 (de) | 2004-05-06 |
US7205349B2 (en) | 2007-04-17 |
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