JPS63175056A - Plasticizer for vinyl chloride based resin - Google Patents
Plasticizer for vinyl chloride based resinInfo
- Publication number
- JPS63175056A JPS63175056A JP412087A JP412087A JPS63175056A JP S63175056 A JPS63175056 A JP S63175056A JP 412087 A JP412087 A JP 412087A JP 412087 A JP412087 A JP 412087A JP S63175056 A JPS63175056 A JP S63175056A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl chloride
- plasticizer
- glyceryl
- chloride resin
- general formula
- 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
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 229920005989 resin Polymers 0.000 title claims abstract description 49
- 239000011347 resin Substances 0.000 title claims abstract description 49
- 239000004014 plasticizer Substances 0.000 title claims abstract description 43
- -1 triglyceride compound Chemical class 0.000 claims abstract description 24
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims abstract description 14
- 125000005313 fatty acid group Chemical group 0.000 claims abstract 3
- 239000011342 resin composition Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 5
- 230000003000 nontoxic effect Effects 0.000 abstract description 5
- MAYCICSNZYXLHB-UHFFFAOYSA-N tricaproin Chemical compound CCCCCC(=O)OCC(OC(=O)CCCCC)COC(=O)CCCCC MAYCICSNZYXLHB-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 abstract 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 13
- 150000004665 fatty acids Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- GOJCZVPJCKEBQV-UHFFFAOYSA-N Butyl phthalyl butylglycolate Chemical compound CCCCOC(=O)COC(=O)C1=CC=CC=C1C(=O)OCCCC GOJCZVPJCKEBQV-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
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- DJDSLBVSSOQSLW-UHFFFAOYSA-N mono(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O DJDSLBVSSOQSLW-UHFFFAOYSA-N 0.000 description 3
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 3
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 description 3
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 description 2
- LVAGMBHLXLZJKZ-UHFFFAOYSA-N 2-o-decyl 1-o-octyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC LVAGMBHLXLZJKZ-UHFFFAOYSA-N 0.000 description 2
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N diheptyl phthalate Chemical compound CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- YAFOVCNAQTZDQB-UHFFFAOYSA-N octyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC)OC1=CC=CC=C1 YAFOVCNAQTZDQB-UHFFFAOYSA-N 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- REAAUFDFYPKMIR-UHFFFAOYSA-N 2,3-bis(2-methylpropanoyloxy)propyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCC(OC(=O)C(C)C)COC(=O)C(C)C REAAUFDFYPKMIR-UHFFFAOYSA-N 0.000 description 1
- PZJLFHDNXGAZHU-UHFFFAOYSA-N 2,3-di(pentanoyloxy)propyl pentanoate Chemical compound CCCCC(=O)OCC(OC(=O)CCCC)COC(=O)CCCC PZJLFHDNXGAZHU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 108010049003 Fibrinogen Proteins 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 231100000111 LD50 Toxicity 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CGSLYBDCEGBZCG-UHFFFAOYSA-N Octicizer Chemical compound C=1C=CC=CC=1OP(=O)(OCC(CC)CCCC)OC1=CC=CC=C1 CGSLYBDCEGBZCG-UHFFFAOYSA-N 0.000 description 1
- MRWSBLWWDRNONW-UHFFFAOYSA-N P(=O)(OCCCC)(OC1(C(C=CC=C1)C)C)OC1(C(C=CC=C1)C)C Chemical compound P(=O)(OCCCC)(OC1(C(C=CC=C1)C)C)OC1(C(C=CC=C1)C)C MRWSBLWWDRNONW-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000004671 saturated fatty acids Chemical group 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 125000005590 trimellitic acid group Chemical class 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N1/00—Preservation of bodies of humans or animals, or parts thereof
- A01N1/02—Preservation of living parts
- A01N1/0205—Chemical aspects
- A01N1/021—Preservation or perfusion media, liquids, solids or gases used in the preservation of cells, tissue, organs or bodily fluids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N1/00—Preservation of bodies of humans or animals, or parts thereof
- A01N1/02—Preservation of living parts
- A01N1/0205—Chemical aspects
- A01N1/021—Preservation or perfusion media, liquids, solids or gases used in the preservation of cells, tissue, organs or bodily fluids
- A01N1/0226—Physiologically active agents, i.e. substances affecting physiological processes of cells and tissue to be preserved, e.g. anti-oxidants or nutrients
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biophysics (AREA)
- Physiology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、塩化ビニル系樹脂用可塑剤に関するものであ
る。詳しく述べると本発明は、無毒性でかつ塩化ビニル
系樹脂に対し良好な相溶性と可塑化効率を有する塩化ビ
ニル系樹脂用可塑剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a plasticizer for vinyl chloride resins. Specifically, the present invention relates to a plasticizer for vinyl chloride resins that is non-toxic and has good compatibility and plasticization efficiency with vinyl chloride resins.
（従来の技術）
現在、食品容器などにおいて、その成形性、柔軟性、透
明性、耐熱性および低価格性の良好さゆえに、軟質塩化
ビニル樹脂製のものが広く使用されている。ところで毒
性が問題となる場合、軟質塩化ビニル樹脂は、通常可塑
剤としてジー ２−エチルへキシルフタレート（ＤＯＰ
＞を用いている。(Prior Art) Currently, containers made of soft vinyl chloride resin are widely used for food containers and the like because of their good moldability, flexibility, transparency, heat resistance, and low cost. By the way, when toxicity is a problem, soft vinyl chloride resin is usually treated with di-2-ethylhexyl phthalate (DOP) as a plasticizer.
> is used.
ジー ２−エチルフタレートは可塑剤の中で比較的安全
であるとされているが、一般にフタル酸エステル系の可
塑剤は移行性が大きい。また、ジー２−エチルへキシル
フタレートの代謝産物であるモノ−２−エチルへキシル
フタレート（ＭＥＨＰ）に変異原性が認められている（
ヤギら、テラトロジー １４２５９ （１９７６） ［
Ｙａｇｉ ｅｔ ａｔ、、 Ｔｅｒａｔｏｌｏｇｙ旦２
５９ （１９７６）コ）ためにジー２−エチルへキシル
フタレートに代わる物質が切望されていた。Although di-2-ethyl phthalate is considered to be relatively safe among plasticizers, phthalate ester plasticizers generally have a high migration property. Additionally, mono-2-ethylhexyl phthalate (MEHP), a metabolite of di-2-ethylhexyl phthalate, has been found to be mutagenic (
Yagi et al., Teratology 14259 (1976) [
Yagi et at,, Teratology Dan 2
59 (1976), there was a strong need for a substance to replace di-2-ethylhexyl phthalate.
また、ジー ２−エチルへキシルフタレート以外に、Ｊ
１在無毒性であるとして知られる可塑剤としては、ブチ
ルフタリル・ブチルグリコレート（ＢＰＢＧ） 、オク
チルジフェニルホスフェート、エポキシ化植物油（ＥＳ
ＢＯ） 、クエン酸エステル、ニトリルゴムなどが挙げ
られるが、これらはいずれも相溶性、可塑化効率、着色
性、耐水性などの面で問題があった。In addition to di-2-ethylhexyl phthalate, J
Plasticizers known to be non-toxic include butylphthalyl butyl glycolate (BPBG), octyldiphenyl phosphate, and epoxidized vegetable oil (ES).
BO), citric acid ester, nitrile rubber, etc., but all of these have problems in terms of compatibility, plasticization efficiency, colorability, water resistance, etc.
（発明が解決しようとする問題点）
従って、本発明は、新規な塩化ビニル系樹脂用可塑剤を
提供することを目的とする。本発明はまた、無毒性でか
つ塩化ビニル系樹脂に対して良好な相溶性および可塑化
効率を有する塩化ビニル系樹脂用可塑剤を提供すること
を目的とする。(Problems to be Solved by the Invention) Therefore, an object of the present invention is to provide a novel plasticizer for vinyl chloride resins. Another object of the present invention is to provide a plasticizer for vinyl chloride resins that is non-toxic and has good compatibility and plasticization efficiency with vinyl chloride resins.
（問題点を解決するための手段）
上記諸目的は、一般式（Ｉ）
ＣＨ２ＯＲ’
ＣＨＯＲ２（Ｉ ）
ＣＨ２０Ｒ３
（式中、Ｒ１、Ｒ２およびＲ３はそれぞれ炭素数２〜１
２の脂肪酸残基でおる。）
表わされるトリグリセリド化合物よりなる塩化ビニル系
樹脂用可塑剤により達成される。(Means for Solving the Problems) The above objects are achieved by formula (I) CH2OR' CHOR2(I) CH20R3 (wherein R1, R2 and R3 each have 2 to 1 carbon atoms)
2 fatty acid residues. ) This can be achieved using a plasticizer for vinyl chloride resins consisting of the triglyceride compound shown below.
本発明はまた、塩化ビニル系樹脂組成物に配合されるも
のでおる塩化ビニル系樹脂用可塑剤を示すものである。The present invention also provides a plasticizer for vinyl chloride resin that is blended into a vinyl chloride resin composition.
本発明はさらに、一般式（Ｉ）においてＲ１、Ｒ２およ
びＲ３がそれぞれ炭素数６〜１０の脂肪酸残基である塩
化ビニル系樹脂用可塑剤を示すものである。本発明はさ
らに、一般式（Ｉ）にいてＲ１、Ｒ２およびＲ３の少な
くとも一つが分岐構造をとる塩化ビニル系樹脂用可塑剤
を示すものである。本発明はさらに、トリグリセリド化
合物がグリセリル トリー ２−エチルヘキナノエート
である塩化ビニル系樹脂用可塑剤を示すものである。本
発明はまた塩化ビニル系樹脂１００重量部に対し、５〜
６０重量部配合されるものである塩化ビニル系樹脂用可
塑剤を示すもので必る。The present invention further provides a plasticizer for vinyl chloride resins in which R1, R2 and R3 in the general formula (I) are each a fatty acid residue having 6 to 10 carbon atoms. The present invention further provides a plasticizer for vinyl chloride resins in which at least one of R1, R2 and R3 in general formula (I) has a branched structure. The present invention further provides a plasticizer for vinyl chloride-based resins, wherein the triglyceride compound is glyceryl tri-2-ethylhexynanoate. The present invention also provides 5 to 5 parts by weight of vinyl chloride resin.
This indicates a plasticizer for vinyl chloride resins, which is blended in an amount of 60 parts by weight.
（作用）
本発明の塩化ビニル系樹脂用可塑剤は、一般式％式％
（式中、Ｒ１、Ｒ２およびＲ３はそれぞれ炭素数２〜１
２、好ましくは６〜１０の脂肪酸残塁である。）
で表わされるトリグリセリド化合物でおる。(Function) The plasticizer for vinyl chloride resin of the present invention has the general formula % (wherein R1, R2 and R3 each have 2 to 1 carbon atoms.
2, preferably 6 to 10 fatty acid residues. ) is a triglyceride compound represented by
一般式（Ｉ＞で表わされるトリグリセリド化合物のよう
な中鎖長脂肪酸のグリセリンエステルは、従来化粧品な
どの乳化剤として用いられてきた安全性の高い化合物で
おり、このような中鎖長脂肪酸のグリセリンエステル単
体での毒性は、グリセリン トリカプリラードを例にと
れば、マウス静脈中投与時のＬＤ５ｏ、（５０％致死量
）が３７００ｍ’ｊ／に’ｊ＜アクタ フィジオロジ力
スカンディナビ力 ４０． ３３８（１９５７）
［Ａｃｔａ Ｐｈｙｓｉｏｌ、 ５ｃａｎｄ。Glycerin esters of medium-chain fatty acids, such as triglyceride compounds represented by the general formula (I>), are highly safe compounds that have been used as emulsifiers in cosmetics. Taking glycerin tricaprylad as an example, the LD5o (50% lethal dose) when administered intravenously to mice is 3700 m'j/'j < Acta Physiology 40. 338 (1957)
[Acta Physiol, 5cand.
４０、 ３３８ （１９５７） ］ ）であるのに対し
ジー ２−°エチルへキシルフタレートでは１０６０ｍ
Ｆｊ／Ｋｇであり（ナショナル テクニカル インフォ
メーション サービス ピービー、 ２５０． １０
２ ［Ｎａｔｉｏｎａｌ Ｔｅｃｈｎｉｃａｌ Ｉｎｆ
ｏｒｍａｔｉｏｎ ５ｅｒｖｉｃｅ ＰＢ ２５０．
１０２］ ） 、またラットを用いた生殖試験ではＴ
Ｄ、。40, 338 (1957)]), whereas for G2-°ethylhexyl phthalate it is 1060 m.
Fj/Kg (National Technical Information Service P.B., 250.10
2 [National Technical Inf.
ormation 5service PB 250.
[102]), and in reproductive studies using rats, T
D.
（最低毒性投与１）がグリセリル トリカプリラードの
場合、経口投与で２５０ｇ／Ｋｇ（医薬品研究 ３．
１８０ （１９７２） ）であるのに対し、ジー２−エ
チルへキシルフタレートでは７１４０ｍ３／に’Ｊであ
ると報告されている（トキシコロジカル アプリケーシ
ョン オブ ）７−マコピー７２６゜２５３ （１９
７３） ［丁ｏｘｉｃｏ１． Ａｐｐｌ、 Ｐ
ｈａｍ、 ２６． ２５３（１９７３） ］ ）
。以上の事から明らかなように、一般式（Ｉ）で表わさ
れるトリグリセリド化合物は、従来可塑剤として用いら
れているジー ２−エチルへキシルフタレートの比べて
毒性の低い安全な物質であるが、驚くべきことにこの一
般式（１）で表わされるトリグリセリド化合物は、塩化
ビニル系樹脂との相溶性に優れ、またこの可塑化効率も
十分であることが見出されたものである。If (least toxic dose 1) is glyceryl tricaprylad, oral administration is 250g/Kg (Pharmaceutical Research 3.
180 (1972)), whereas di-2-ethylhexyl phthalate is reported to be 7140 m3/'J (Toxicological Applications) 7-macopy 726°253 (19
73) [Choxico1. Appl, P.
ham, 26. 253 (1973) )
. As is clear from the above, the triglyceride compound represented by the general formula (I) is a safer substance with lower toxicity than di-2-ethylhexyl phthalate, which is conventionally used as a plasticizer. It has been found that the triglyceride compound represented by the general formula (1) has excellent compatibility with vinyl chloride resins and has sufficient plasticization efficiency.
以下、本発明を実施態様に基づきより詳細に説明する。Hereinafter, the present invention will be explained in more detail based on embodiments.
本発明の塩化ビニル系樹脂用可塑剤は、一般式％式％
（式中、Ｒ１、Ｒ２およびＲ３はそれぞれ炭素数２〜１
２、好ましくは６〜１０の脂肪酸残基である。）
で表わされるトリグリセリド化合物であるが、脂肪酸残
基Ｒ１、Ｒ２およびＲ３の炭素数を２〜１２とするのは
、炭素数が２〜］２の範囲を外れると、トリグリセリド
化合物と塩化ビニル樹脂との相溶性がなくなってしまう
からである。ざらに、脂肪酸残基Ｒ１、Ｒ２およびＲ３
の炭素数が６〜１０のものであると、塩化ビニル樹脂に
対する可塑化効率がより向上するために好ましい。また
一般式（Ｉ）で表わされるトリグリセリド化合物におい
て、脂肪酸残基Ｒ１、Ｒ２およびＲ３の少なくとも一つ
が分岐構造をとるほうが塩化ビニル系樹脂との相溶性の
面からより好ましい。また一般式（Ｉ＞で表わされるト
リグリセリド化合物において、脂肪酸残基Ｒ１、Ｒ２お
よびＲ３は必ずしも同一のものである必要はなく鎖長の
異なるものの組合せであってもよい。さらに脂肪酸残基
Ｒ１゜Ｒ２およびＲ３は飽和脂肪酸残基でも不飽和脂肪
酸残塁であってもよい。一般式（Ｉ＞で表わされるトリ
グリセリド化合物として具体的には、例えばグリセリル
トリアセテート（トリアセチン）、グリセリル トリ
プロピオネート（トリプロピオニン）、クリセリル ト
リブチレート（トリブチリン）、グリセリル トリイソ
ブチレート（トリイソブチリン）、グリセリル トリバ
レレート（トリバレリン）、グリセリル トリカプロエ
ート、グリセリル １−リカプリラード、グリセリルト
リ− ２−エチルへキナノエート、グリセリルトリカプ
レート、グリセリル トリラウレート（トリラウリン）
などが挙げられるが、好ましくはグリセリル トリカプ
ロエート、グリセリルトリカプリラード、グリセリル
トリー ２−エチルへキナノエートおよびグリセリル
トリカプレートでおり、最も好ましくはグリセリル ト
リー２−エチルヘキサノエートである。The plasticizer for vinyl chloride resins of the present invention has the general formula % (where R1, R2 and R3 each have 2 to 1 carbon atoms).
2, preferably 6 to 10 fatty acid residues. ), but the reason why fatty acid residues R1, R2, and R3 have 2 to 12 carbon atoms is because if the carbon number is outside the range of 2 to 2, the triglyceride compound and vinyl chloride resin This is because the compatibility of the two will be lost. In general, fatty acid residues R1, R2 and R3
It is preferable that the number of carbon atoms is 6 to 10 because the plasticizing efficiency for vinyl chloride resin is further improved. Further, in the triglyceride compound represented by the general formula (I), it is more preferable that at least one of the fatty acid residues R1, R2 and R3 has a branched structure from the viewpoint of compatibility with the vinyl chloride resin. Furthermore, in the triglyceride compound represented by the general formula (I>), fatty acid residues R1, R2, and R3 are not necessarily the same, and may be a combination of different chain lengths.Furthermore, fatty acid residues R1゜R2 and R3 may be a saturated fatty acid residue or an unsaturated fatty acid residue.Specifically, triglyceride compounds represented by the general formula (I>) include, for example, glyceryl triacetate (triacetin), glyceryl tripropionate (tripropionine), and chryceryl tripropionate (tripropionine). Tributyrate (tributyrin), glyceryl triisobutyrate (triisobutyrin), glyceryl trivalerate (trivalerin), glyceryl tricaproate, glyceryl 1-licaprylad, glyceryl tri-2-ethyl hequinanoate, glyceryl tricaprate, glyceryl trilaurate (trilaurin)
etc., but preferred are glyceryl tricaproate, glyceryl tricaprylate, and glyceryl tricaproate.
Tri-2-ethyl hequinanoate and glyceryl
Trikaplate, most preferably glyceryl tri-2-ethylhexanoate.
本発明に係る上記のごとき塩化ビニル系樹脂用可塑剤に
より可塑化され得る塩化ビニル系樹脂としては、塩化ビ
ニルの単独重合体の他にポリ塩化ビニリデン、塩化ビニ
ルを４０重遣％以上、好ましくは６５重層％以上、最も
好ましくは７５重層％以上含有する他の共重合し得る単
量体との共重合体等があり、その平均重合度は４００〜
３．０００、好ましくは６００〜．２，７００．最も好
ましくは８００〜１，７００である。塩化ビニルに対す
る共単滑体としては、塩化ビニリデン、エチレン、プロ
ピレン、酢酸ビニル、臭化ビニル、弗化ごニル、スチレ
ン、ビニルトルエン、ビニルピリジン、アクリル醒、ア
ルキルアクリレート（例えばメチルアクリレート、エチ
ルアクリレート、イソプロピルアクリレート、ｎ−ブチ
ルアクリレート、２−エチルへキシルアクリレート等）
、メタクリル酸、アルキルメタクリレート（例えば、メ
チルメタクリレート、エチルメタクリレート、２−エチ
ルへ主シルメタクリレート等）、アクリロニトリル、メ
タクリレートリル等がある。また、塩化ビニル樹脂には
、スチレン−アクリロニトリル共重合体、スチレンーメ
タクリロニトリル共重合体を配合することができる。The vinyl chloride resin that can be plasticized with the vinyl chloride resin plasticizer described above according to the present invention includes polyvinylidene chloride and vinyl chloride in an amount of 40% by weight or more, preferably in addition to a homopolymer of vinyl chloride. There are copolymers with other copolymerizable monomers containing 65% or more, most preferably 75% or more, and the average degree of polymerization is 400-400%.
3.000, preferably 600~. 2,700. Most preferably it is 800-1,700. Co-monomers for vinyl chloride include vinylidene chloride, ethylene, propylene, vinyl acetate, vinyl bromide, vinyl fluoride, styrene, vinyltoluene, vinylpyridine, acrylic acid, alkyl acrylates (e.g. methyl acrylate, ethyl acrylate, isopropyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, etc.)
, methacrylic acid, alkyl methacrylates (eg, methyl methacrylate, ethyl methacrylate, 2-ethyl methacrylate, etc.), acrylonitrile, methacrylatetril, and the like. Moreover, a styrene-acrylonitrile copolymer and a styrene-methacrylonitrile copolymer can be blended with the vinyl chloride resin.
このような塩化ビニル系樹脂に対して、上記一般式（Ｉ
）で表わされるトリグリセリド化合物は十分な相溶性と
可塑化効率を有するゆえ、可塑剤として単独で用いられ
ることができ、この場合、配合量としては、塩化ビニル
系樹脂１００重量部に対し、５〜６０重量部、より好ま
しくは１０〜５０重Ｊ部でおる。このように本発明に係
る一般式（Ｉ＞で表わされるトリグリセリド化合物のみ
で可塑化された塩化ビニル系樹脂組成物は、極めて浸れ
た安全性を有する。無毒性を必要とする場合、塩化ビニ
ル系樹脂１００重遭部に対し、上記一般式（１）で表わ
されるトリグリセリド化合物５〜６０重量部、安定剤兼
補助可塑剤としてのエポキシ化大豆油、エポキシ化アマ
ニ油等のエポキシ化植物油類３〜１０重量部および安定
剤としてのカルシウム、亜鉛等とステアリン酸、ラウリ
ン酸、リシノール酸、ナフテン酸等との金属石鹸０００
５〜３ｆ履部を配合してなる組成を有することが望まし
い。 本発明の塩化ビニル系樹脂用可塑剤は、上記した
ように塩化ビニル系樹脂に対し単独で可塑剤として作用
し得るものであるが、もちろんその他の可塑剤と組合せ
て使用することも可能である。For such vinyl chloride resin, the above general formula (I
The triglyceride compound represented by ) has sufficient compatibility and plasticizing efficiency, so it can be used alone as a plasticizer. The amount is 60 parts by weight, more preferably 10 to 50 parts by weight. As described above, the vinyl chloride resin composition plasticized only with the triglyceride compound represented by the general formula (I>) according to the present invention has extremely high safety. 5 to 60 parts by weight of a triglyceride compound represented by the general formula (1) above, and 3 to 60 parts by weight of epoxidized vegetable oils such as epoxidized soybean oil and epoxidized linseed oil as a stabilizer and auxiliary plasticizer per 100 parts of the resin. Metal soap containing 10 parts by weight and calcium, zinc, etc. as a stabilizer and stearic acid, lauric acid, ricinoleic acid, naphthenic acid, etc. 000
It is desirable to have a composition containing a 5 to 3 f shoe part. The plasticizer for vinyl chloride resins of the present invention can act alone as a plasticizer for vinyl chloride resins as described above, but of course it can also be used in combination with other plasticizers. .
本発明の塩化ビニル系樹脂用可塑剤と併用できる他の可
塑剤としては、一般に塩化ビニル樹脂用として使用でき
るものであればいずれでもよく、そのいくつかを列挙す
ればジブチルフタレート（ＤＢＰ） 、ジブチルフタレ
ート（ＤＨＰ）、ジー２−エチルへキシルフタレート（
ＤＯＰ）。As other plasticizers that can be used in combination with the plasticizer for vinyl chloride resins of the present invention, any plasticizer that can be generally used for vinyl chloride resins may be used, and some of them include dibutyl phthalate (DBP), dibutyl Phthalate (DHP), di-2-ethylhexyl phthalate (
DOP).
シーｎ−オクチルフタレート（ＤｎＯＰ）、ジイソオク
チルフタレート（ＤＩＯＰ）、ジヘプチルフタレート、
ジデシルフタレート（ＤＤＰ）、ジイソデシルフタレー
ト（Ｄ■ＤＰ＞、オクチルデシルフタレート、ブチルベ
ンジルフタレート（ＢＢＰ）等のフタル酸エステル類、
トリブチルトリメリテート、トリオクチルトリメリテー
ト等のトリメリット酸エステル類、ジオクチルアジペー
ト（ＤＯＡ＞、ジオクチルアゼレート（ＤＯＺ）。Sea n-octyl phthalate (DnOP), diisooctyl phthalate (DIOP), diheptyl phthalate,
Phthalate esters such as didecyl phthalate (DDP), diisodecyl phthalate (D■DP>, octyldecyl phthalate, butylbenzyl phthalate (BBP),
Trimellitic acid esters such as tributyl trimellitate and trioctyl trimellitate, dioctyl adipate (DOA>), dioctyl azelate (DOZ).
ジオクチルセバケート（ＤＯ３＞等の脂肪族多塩基酸エ
ステル類、トリクレジルホスフェート（ＴＣＰ）、トリ
キシレニルホスフェート（ＴＸＰ）。Aliphatic polybasic acid esters such as dioctyl sebacate (DO3>), tricresyl phosphate (TCP), and tricylenyl phosphate (TXP).
モノオクチルジフェニルホスフェート（Ｓａｎｔｉｃｉ
ｚｅｒ１４１）、モノブチルジキシレニルホスフェート
（Ｂ−２−Ｘ＞、 トリオクチルホスフェート（丁Ｏ
Ｆ）類のリン酸エステル類、トリブチルアセチルシトレ
ート、トリオクチルアセチルシトレート、トリブチルシ
トレート等のクエン酸エステル類、ブチルフタリルブチ
ルグリコレート（ＢＰＢＧ）等がある。Monooctyl diphenyl phosphate (Santici
zer141), monobutyl dixylenyl phosphate (B-2-X>, trioctyl phosphate (D-O
F) type phosphate esters, citric acid esters such as tributylacetyl citrate, trioctyl acetyl citrate, and tributyl citrate, butylphthalylbutyl glycolate (BPBG), and the like.
本発明の塩化ビニル系樹脂用可塑剤を配合してなる塩化
ビニル系樹脂組成物の成形方法としては、従来の塩化ビ
ニル系樹脂組成物に関して用いられている方法、例えば
カレンダー成形、押出し成形、プラスチゾル成形等のい
ずれの方法によっても成形可能であり、また接着法とし
ても高周波融着、熱融着等が可能でおる。The vinyl chloride resin composition containing the vinyl chloride resin plasticizer of the present invention may be molded by any of the methods used for conventional vinyl chloride resin compositions, such as calendar molding, extrusion molding, and plastisol molding. It can be formed by any method such as molding, and can be bonded by high frequency fusion, heat fusion, etc.
（実施例）
以下、本発明を実施例に基づきさらに具体的に説明する
。(Examples) Hereinafter, the present invention will be explained in more detail based on Examples.
実施例１
第１表に示すような組成を有する塩化ビニル系樹脂組成
物を、１５０℃で５分間ロール混練した後、１６０°Ｃ
１４００ＫＩ／ｃｍで６分間加圧してプレス成形を行な
い厚さ０．４調のシートを作成した。得られたシートの
物性を測定した結果を第２表に示す。なお１００％モジ
ュラスおよび引張強度の測定はＪＩＳ Ｋ７１１３に
準じて行なった。Example 1 A vinyl chloride resin composition having the composition shown in Table 1 was roll-kneaded at 150°C for 5 minutes, and then kneaded at 160°C.
Press molding was performed by applying pressure at 1400 KI/cm for 6 minutes to create a sheet with a thickness of 0.4 tone. Table 2 shows the results of measuring the physical properties of the obtained sheet. Note that 100% modulus and tensile strength were measured according to JIS K7113.
またこのシートを、１２１°Ｃで６０分間の高圧蒸気処
理にかけたところシートの変形は認められなかった。Further, when this sheet was subjected to high-pressure steam treatment at 121°C for 60 minutes, no deformation of the sheet was observed.
比較例１
第１表に示すような組成を有する塩化ビニル系樹脂組成
物で、実施例１と同様にして厚さ０．４跡のシートを作
成し、得られたシートの物性を測定して実施例１のもの
と比較した。結果を第２表に示す。Comparative Example 1 A sheet with a thickness of 0.4 mm was prepared in the same manner as in Example 1 using a vinyl chloride resin composition having the composition shown in Table 1, and the physical properties of the obtained sheet were measured. A comparison was made with that of Example 1. The results are shown in Table 2.
弱 へ い Ｈ模
第２表
塩化ビニル系樹脂組成物の物性
実施例１ 比較例１
１００％モジュラス １１２ １００１００（
／ｃｄ）
引張強度 ２０４ ２０６（Ｋｇｆ／
Ｃ／ｉ）
これらの結果から明らかなように本発明の塩化ビニル系
樹脂用可塑剤の１つであるグリセリルトリ− ２−エチ
ルヘキサノエートは、２−エチル゛ヘキシルフタレート
と同様に塩化ビニル樹脂に対し優れた相溶性と可塑化効
率を示し、また得られる樹脂組成物の物性を低下させる
こともなかった。Weak To H model Table 2 Physical properties of vinyl chloride resin composition Example 1 Comparative example 1 100% modulus 112 100100 (
/cd) Tensile strength 204 206 (Kgf/
C/i) As is clear from these results, glyceryl tri-2-ethylhexanoate, which is one of the plasticizers for vinyl chloride resins of the present invention, is effective for vinyl chloride resins like 2-ethylhexyl phthalate. It showed excellent compatibility and plasticization efficiency with respect to the resin composition, and the physical properties of the resulting resin composition were not deteriorated.
実施例２
メタノールにグリセリル トリー ２−エチルヘキサノ
エートに２００００ ｐＩ）ｍを溶解した溶液を、ヒト
乏血小板血漿に１／１００１Ｊｉとなるように添加し、
この乏血小板血漿２ＩＩｉｌをヒト多血小板血漿１ｍｌ
に加え３７°Ｃで９０分間インキュベートした。この後
、血小板を洗浄しくレグランドら、ヨーロピアン ジャ
ーナル オブ バイオケミストリー１４２゜４６５ （
１９８４） ［ＬｅＯｒａｎｄ ｅｔ ａｌ、、 Ｅ
ｕｒ、 Ｊ、 １３ｉｏｃｈｅｍ、 １４２． ４６５
（１９８４） ］ ） 、タイロード「丁ｙｒｏｄｅ
ｌ／ＢＳＡ液（０，２ｍＭ ＣａＣΩ２’、 ’１ｍ
）Ｉ ＭＱ（、Ｑ２ 、５ｍＭ ＨＥＰＥＳ 、
３．５Ｊｉ１ｇ／ｌｒｄ！ＢＳＡを含むタイロード液、
ｐＨ，７，３５＞に再浮遊し、０゜２ｍｓ／彪フィブリ
ノーゲン存在下５０μＭ ＡＤＰおよび１０μＱ／ｄ
コラーゲンに対する最大凝集能を測定した。結果を第３
表に示す。Example 2 A solution of 20,000 pI)m dissolved in glyceryl tri-2-ethylhexanoate in methanol was added to human platelet-poor plasma at a concentration of 1/1001 Ji,
This platelet-poor plasma 2IIIil was mixed with 1ml of human platelet-rich plasma.
and incubated for 90 minutes at 37°C. After this, the platelets were washed and washed by Legland et al., European Journal of Biochemistry 142°465 (
1984) [LeOrand et al., E.
ur, J, 13iochem, 142. 465
(1984) ), Tyrod
l/BSA solution (0.2mM CaCΩ2', '1m
)IMQ(,Q2,5mM HEPES,
3.5Ji1g/lrd! Tyrode's solution containing BSA,
Resuspend at pH 7,35>, 0°2 ms/biao in the presence of fibrinogen with 50 μM ADP and 10 μQ/d.
The maximum aggregation capacity for collagen was measured. 3rd result
Shown in the table.
比較例２
メタノールにジー ２−エチルへキシルフタレート２０
０００９Ｄｍを溶解した溶液に関して、実施例２と同様
にして５０μＭ ＡＤＰおよび１０μｇ／ｍｆｆ１コ
ラーゲンに対する最大凝集能を測定した。Comparative Example 2 Di-2-ethylhexyl phthalate 20 in methanol
Regarding the solution in which 0009Dm was dissolved, the maximum aggregation ability for 50 μM ADP and 10 μg/mff1 collagen was measured in the same manner as in Example 2.
結果を第３表に示す。The results are shown in Table 3.
比較例３
何も添加していないメタノールに関して、実施例２と同
様にして５０μＭ ＡＤＰおよび１０μＣｌ／ｍｉコ
ラーゲンに対する最大凝集能を測定した。Comparative Example 3 Regarding methanol to which nothing was added, the maximum aggregation ability for 50 μM ADP and 10 μCl/mi collagen was measured in the same manner as in Example 2.
結果を第３表に示す。The results are shown in Table 3.
（以下余白）
二
ぺ ；八
ｔべ ＝ −
第３表に示すように、ジー ２−エチルへキシルフタレ
ートには、血小板の凝集前回復に対する抑制作用がみら
れるが、グリセリル トリー ２−エチルへキ丈ノエー
トには抑制作用がほとんど認られずより安全性の高い物
質であるといえる。(Leaving space below) As shown in Table 3, di-2-ethylhexyl phthalate has an inhibitory effect on the pre-aggregation recovery of platelets, but glyceryl tri-2-ethylhexyl phthalate Chonoate has almost no inhibitory effect and can be said to be a safer substance.
（発明の効果）
以上述べたように、本発明は、一般式（Ｉ）で表わされ
るトリグリセリド化合物よりなる塩化ビニル系樹脂用可
塑剤であって、実質的に無毒性でかつ、塩化ビニル系樹
脂に対して良好な相溶性および可塑化効率を示すもので
あり、また該可塑剤を配合されてなる塩化ビニル系樹脂
組成物は、浸れた安全性、成形性、柔軟性、透明性、耐
熱性等を示し得ることとなることから、塩化ビニル系樹
脂用の可塑剤として、特に食品などの容器に用いる塩化
ビニル系樹脂用の可塑剤として好適に使用され得るもの
である。さらに本発明の塩化ビニル系樹脂用可塑剤にお
いて、一般式（Ｉ）で表わされるトリグリセリド化合物
が炭素数６〜１０の脂肪酸残基を有するもの、より好ま
しくは一般式（１）においてＲ／Ｉ 、 Ｒ２およびＲ
３の少なくとも一つが分岐構造をとるもの、さらに好ま
しくはグリセリル トリー ２−エチルへキナノエート
である場合には、より優れ３た相溶性および可塑化効率
を示しかつ安全性もさらに高いものとなるために、一層
優れた性能を有する塩化ビニル系樹脂組成物を提供でき
るものとなる。(Effects of the Invention) As described above, the present invention provides a plasticizer for vinyl chloride resin, which is made of a triglyceride compound represented by the general formula (I), which is substantially non-toxic and It shows good compatibility and plasticization efficiency with plasticizers, and vinyl chloride resin compositions containing this plasticizer have excellent properties such as immersion safety, moldability, flexibility, transparency, and heat resistance. Therefore, it can be suitably used as a plasticizer for vinyl chloride resins, particularly for vinyl chloride resins used in food containers. Furthermore, in the plasticizer for vinyl chloride resin of the present invention, the triglyceride compound represented by the general formula (I) has a fatty acid residue having 6 to 10 carbon atoms, more preferably R/I in the general formula (1), R2 and R
When at least one of 3 has a branched structure, more preferably glyceryl tri-2-ethyl hequinanoate, 3 exhibits better compatibility and plasticization efficiency, and also has higher safety. This makes it possible to provide a vinyl chloride resin composition with even better performance.
Claims (6)
２〜１２の脂肪酸残基である。） で表わされるトリグリセリド化合物よりなる塩化ビニル
系樹脂用可塑剤。(1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1, R^2, and R^3 are each fatty acid residues having 2 to 12 carbon atoms. ) A plasticizer for vinyl chloride resins consisting of a triglyceride compound represented by:
特許請求の範囲第１項に記載の塩化ビニル系樹脂用可塑
剤。(2) The plasticizer for vinyl chloride resin according to claim 1, which is blended into a vinyl chloride resin composition.
＾３がそれぞれ炭素数６〜１０の脂肪酸残基である特許
請求の範囲第１項に記載の塩化ビニル系樹脂用可塑剤。(3) In general formula (I), R^1, R^2 and R
The plasticizer for vinyl chloride resins according to claim 1, wherein each ^3 is a fatty acid residue having 6 to 10 carbon atoms.
Ｒ＾３の少なくとも一つが分岐構造をとる特許請求の範
囲第１項に記載の塩化ビニル系樹脂用可塑剤。(4) The plasticizer for vinyl chloride resins according to claim 1, wherein in the general formula (I), at least one of R^1, R^2, and R^3 has a branched structure.
エチルヘキサノエートである特許請求の範囲第３項に記
載の塩化ビニル系樹脂用可塑剤。(5) The triglyceride compound is glyceryl tri-2-
The plasticizer for vinyl chloride resins according to claim 3, which is ethylhexanoate.
重量部配合されるものである特許請求の範囲第１項〜第
５項のいずれかに記載の塩化ビニル系樹脂用可塑剤。(6) 5 to 60 parts by weight of vinyl chloride resin
The plasticizer for vinyl chloride resins according to any one of claims 1 to 5, which is blended in parts by weight.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP412087A JPS63175056A (en) | 1987-01-13 | 1987-01-13 | Plasticizer for vinyl chloride based resin |
| DE3855956T DE3855956T2 (en) | 1987-01-13 | 1988-01-11 | Use of a triglyceride compound as a hemolysis inhibitor |
| AU11032/88A AU610120B2 (en) | 1987-01-13 | 1988-01-11 | Hemolysis depressent and blood preserving composition |
| EP88900798A EP0340305B1 (en) | 1987-01-13 | 1988-01-11 | Hemolysis inhibitor and plasticizer |
| EP92203200A EP0537863B1 (en) | 1987-01-13 | 1988-01-11 | Use of a triglyceride compound as a hemolysis depressant |
| PCT/JP1988/000020 WO1988005302A1 (en) | 1987-01-13 | 1988-01-11 | Hemolysis inhibitor and plasticizer |
| DE8888900798T DE3880480T2 (en) | 1987-01-13 | 1988-01-11 | HEMOLYSIS INHIBITOR AND PLASTIFICATION AGENT. |
| US07/391,502 US5079002A (en) | 1987-01-13 | 1988-01-11 | Hemolysis depressant and plasticizer |
| ES8800079A ES2010239A6 (en) | 1987-01-13 | 1988-01-13 | Hemolysis inhibitor and plasticizer. |
| US07/769,378 US5248531A (en) | 1987-01-13 | 1991-10-01 | Hemolysis depressant and plasticizer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP412087A JPS63175056A (en) | 1987-01-13 | 1987-01-13 | Plasticizer for vinyl chloride based resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63175056A true JPS63175056A (en) | 1988-07-19 |
Family
ID=11575925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP412087A Pending JPS63175056A (en) | 1987-01-13 | 1987-01-13 | Plasticizer for vinyl chloride based resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63175056A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003507553A (en) * | 1999-08-19 | 2003-02-25 | ダニスコ エイ／エス | Composition |
| JP2008504318A (en) * | 2004-06-29 | 2008-02-14 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | Solid moldings containing active substances for external use against animal parasites |
| JP2013534259A (en) * | 2010-07-28 | 2013-09-02 | ダウ グローバル テクノロジーズ エルエルシー | Cross-reference of applications related to plasticizers prepared from microbial extract oils and polar polymer compositions containing the plasticizers This application claims the benefit of US Patent Application No. 61 / 368,407 (filed July 28, 2010) (The aforementioned patent application is incorporated herein by reference in its entirety). |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5728145A (en) * | 1980-07-25 | 1982-02-15 | Nippon Chem Ind Co Ltd:The | Stabilizer for halogen-containing resin |
| JPS5832647A (en) * | 1981-08-21 | 1983-02-25 | Riken Vitamin Co Ltd | Thermoplastic resin composition |
| JPS5853937A (en) * | 1981-09-25 | 1983-03-30 | Chisso Corp | Vinyl chloride resin composition |
| JPS58167638A (en) * | 1982-03-26 | 1983-10-03 | Riken Vitamin Co Ltd | Thermoplastic resin composition |
| JPS5974148A (en) * | 1983-09-05 | 1984-04-26 | Japan Crown Cork Co Ltd | Non-rigid resin composition |
| JPS59108053A (en) * | 1982-12-10 | 1984-06-22 | Kanegafuchi Chem Ind Co Ltd | Crosslinked vinyl chloride resin composition |
| JPS59168012A (en) * | 1983-03-15 | 1984-09-21 | Mitsui Toatsu Chem Inc | Stretched film for food packaging |
-
1987
- 1987-01-13 JP JP412087A patent/JPS63175056A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5728145A (en) * | 1980-07-25 | 1982-02-15 | Nippon Chem Ind Co Ltd:The | Stabilizer for halogen-containing resin |
| JPS5832647A (en) * | 1981-08-21 | 1983-02-25 | Riken Vitamin Co Ltd | Thermoplastic resin composition |
| JPS5853937A (en) * | 1981-09-25 | 1983-03-30 | Chisso Corp | Vinyl chloride resin composition |
| JPS58167638A (en) * | 1982-03-26 | 1983-10-03 | Riken Vitamin Co Ltd | Thermoplastic resin composition |
| JPS59108053A (en) * | 1982-12-10 | 1984-06-22 | Kanegafuchi Chem Ind Co Ltd | Crosslinked vinyl chloride resin composition |
| JPS59168012A (en) * | 1983-03-15 | 1984-09-21 | Mitsui Toatsu Chem Inc | Stretched film for food packaging |
| JPS5974148A (en) * | 1983-09-05 | 1984-04-26 | Japan Crown Cork Co Ltd | Non-rigid resin composition |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003507553A (en) * | 1999-08-19 | 2003-02-25 | ダニスコ エイ／エス | Composition |
| JP4791667B2 (en) * | 1999-08-19 | 2011-10-12 | ダニスコ エイ／エス | Composition |
| JP2008504318A (en) * | 2004-06-29 | 2008-02-14 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | Solid moldings containing active substances for external use against animal parasites |
| JP2013063980A (en) * | 2004-06-29 | 2013-04-11 | Bayer Animal Health Gmbh | Active substance-containing solid molded body for external use against parasite in animal |
| JP2013534259A (en) * | 2010-07-28 | 2013-09-02 | ダウ グローバル テクノロジーズ エルエルシー | Cross-reference of applications related to plasticizers prepared from microbial extract oils and polar polymer compositions containing the plasticizers This application claims the benefit of US Patent Application No. 61 / 368,407 (filed July 28, 2010) (The aforementioned patent application is incorporated herein by reference in its entirety). |
| US9228155B2 (en) | 2010-07-28 | 2016-01-05 | Dow Global Technologies Llc | Plasticizers made from oil extracted from microorganisms and polar polymeric compositions comprising the same |
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