JP4116884B2 - ポリイソプレン製品及びその製造プロセス - Google Patents
ポリイソプレン製品及びその製造プロセス Download PDFInfo
- Publication number
- JP4116884B2 JP4116884B2 JP2002587502A JP2002587502A JP4116884B2 JP 4116884 B2 JP4116884 B2 JP 4116884B2 JP 2002587502 A JP2002587502 A JP 2002587502A JP 2002587502 A JP2002587502 A JP 2002587502A JP 4116884 B2 JP4116884 B2 JP 4116884B2
- Authority
- JP
- Japan
- Prior art keywords
- polyisoprene
- phr
- elastomer product
- thiazole
- latex composition
- 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 - Lifetime
Links
- 229920001195 polyisoprene Polymers 0.000 title claims abstract description 88
- 238000004519 manufacturing process Methods 0.000 title description 25
- 239000000203 mixture Substances 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 54
- -1 guanidine compound Chemical class 0.000 claims abstract description 46
- 239000003381 stabilizer Substances 0.000 claims abstract description 25
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012990 dithiocarbamate Substances 0.000 claims abstract description 20
- 102000011632 Caseins Human genes 0.000 claims abstract description 19
- 108010076119 Caseins Proteins 0.000 claims abstract description 19
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 claims abstract description 17
- GIUBHMDTOCBOPA-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;zinc Chemical compound [Zn].C1=CC=C2SC(S)=NC2=C1 GIUBHMDTOCBOPA-UHFFFAOYSA-N 0.000 claims abstract description 17
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 claims abstract description 17
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 16
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 16
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 12
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940080237 sodium caseinate Drugs 0.000 claims abstract description 5
- 229920000126 latex Polymers 0.000 claims description 73
- 239000004816 latex Substances 0.000 claims description 73
- 229920001971 elastomer Polymers 0.000 claims description 35
- 239000000806 elastomer Substances 0.000 claims description 32
- 239000005018 casein Substances 0.000 claims description 14
- 235000021240 caseins Nutrition 0.000 claims description 14
- 239000000523 sample Substances 0.000 claims description 10
- 150000002357 guanidines Chemical class 0.000 claims description 6
- 102000014171 Milk Proteins Human genes 0.000 claims description 4
- 108010011756 Milk Proteins Proteins 0.000 claims description 4
- 235000021239 milk protein Nutrition 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229920003051 synthetic elastomer Polymers 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 9
- 229920006173 natural rubber latex Polymers 0.000 abstract description 7
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 39
- 239000000701 coagulant Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 10
- 230000008901 benefit Effects 0.000 description 8
- 238000007598 dipping method Methods 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 238000002386 leaching Methods 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 229920001084 poly(chloroprene) Polymers 0.000 description 3
- 229920000136 polysorbate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- JYYMLZLAIOASOM-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-piperidin-4-ylmethanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1C(=O)C1CCNCC1 JYYMLZLAIOASOM-UHFFFAOYSA-N 0.000 description 2
- FUPAJKKAHDLPAZ-UHFFFAOYSA-N 1,2,3-triphenylguanidine Chemical compound C=1C=CC=CC=1NC(=NC=1C=CC=CC=1)NC1=CC=CC=C1 FUPAJKKAHDLPAZ-UHFFFAOYSA-N 0.000 description 2
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 2
- JSCFNQDWXBNVBP-UHFFFAOYSA-N 1,2-diphenylguanidine;phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.C=1C=CC=CC=1N=C(N)NC1=CC=CC=C1 JSCFNQDWXBNVBP-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 2
- QNTARNCGFNQQRP-UHFFFAOYSA-N 5-carbamothioylsulfanylpentyl carbamodithioate Chemical compound NC(=S)SCCCCCSC(N)=S QNTARNCGFNQQRP-UHFFFAOYSA-N 0.000 description 2
- ZWJGJRRESWKSGB-UHFFFAOYSA-N CC(O)=O.C=1C=CC=CC=1N(C(=N)N)C1=CC=CC=C1 Chemical compound CC(O)=O.C=1C=CC=CC=1N(C(=N)N)C1=CC=CC=C1 ZWJGJRRESWKSGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920002633 Kraton (polymer) Polymers 0.000 description 2
- HXKCUQDTMDYZJD-UHFFFAOYSA-N Methyl selenac Chemical compound CN(C)C(=S)S[Se](SC(=S)N(C)C)(SC(=S)N(C)C)SC(=S)N(C)C HXKCUQDTMDYZJD-UHFFFAOYSA-N 0.000 description 2
- 241000220010 Rhode Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000013566 allergen Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- USBHFGNOYVOTON-UHFFFAOYSA-K bis(dimethylcarbamothioylsulfanyl)bismuthanyl n,n-dimethylcarbamodithioate Chemical compound [Bi+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S USBHFGNOYVOTON-UHFFFAOYSA-K 0.000 description 2
- WRBHGAMSUYCQFW-UHFFFAOYSA-L bis(piperidine-1-carbothioylsulfanyl)lead Chemical compound [Pb+2].[S-]C(=S)N1CCCCC1.[S-]C(=S)N1CCCCC1 WRBHGAMSUYCQFW-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- NJRMCWUECNRJLQ-UHFFFAOYSA-L calcium;n,n-dimethylcarbamodithioate Chemical compound [Ca+2].CN(C)C([S-])=S.CN(C)C([S-])=S NJRMCWUECNRJLQ-UHFFFAOYSA-L 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- OBBCYCYCTJQCCK-UHFFFAOYSA-L copper;n,n-diethylcarbamodithioate Chemical compound [Cu+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S OBBCYCYCTJQCCK-UHFFFAOYSA-L 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- RLULIUSIDLLCSW-UHFFFAOYSA-N diethylcarbamothioylsulfanylselanyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)S[Se]SC(=S)N(CC)CC RLULIUSIDLLCSW-UHFFFAOYSA-N 0.000 description 2
- 150000004659 dithiocarbamates Chemical class 0.000 description 2
- 229950004394 ditiocarb Drugs 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QGTHALAWFUFVCU-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;lead(2+) Chemical compound [Pb+2].CN(C)C([S-])=S.CN(C)C([S-])=S QGTHALAWFUFVCU-UHFFFAOYSA-L 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 2
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 2
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 2
- KMNUDJAXRXUZQS-UHFFFAOYSA-L zinc;n-ethyl-n-phenylcarbamodithioate Chemical compound [Zn+2].CCN(C([S-])=S)C1=CC=CC=C1.CCN(C([S-])=S)C1=CC=CC=C1 KMNUDJAXRXUZQS-UHFFFAOYSA-L 0.000 description 2
- NCSQKSMOKBZEDF-UHFFFAOYSA-L zinc;n-methyl-n-phenylcarbamodithioate Chemical compound [Zn+2].[S-]C(=S)N(C)C1=CC=CC=C1.[S-]C(=S)N(C)C1=CC=CC=C1 NCSQKSMOKBZEDF-UHFFFAOYSA-L 0.000 description 2
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 2
- UCUALOHSSUWYRQ-UHFFFAOYSA-N 1-(2-methylphenyl)-1-phenylguanidine Chemical compound CC1=CC=CC=C1N(C(N)=N)C1=CC=CC=C1 UCUALOHSSUWYRQ-UHFFFAOYSA-N 0.000 description 1
- HXFZHDVPBWJOPB-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;copper Chemical compound [Cu].C1=CC=C2SC(=S)NC2=C1 HXFZHDVPBWJOPB-UHFFFAOYSA-N 0.000 description 1
- UXMWYAHQOASHPK-UHFFFAOYSA-N 4-sulfanyl-3h-1,3-benzothiazole-2-thione;zinc Chemical compound [Zn].SC1=CC=CC2=C1NC(=S)S2 UXMWYAHQOASHPK-UHFFFAOYSA-N 0.000 description 1
- NKYDKCVZNMNZCM-UHFFFAOYSA-N 5-chloro-3h-1,3-benzothiazole-2-thione Chemical compound ClC1=CC=C2SC(S)=NC2=C1 NKYDKCVZNMNZCM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- VEISOORMEMZVJC-UHFFFAOYSA-M C(N)([S-])=S.C(C)[Pb+]CC Chemical compound C(N)([S-])=S.C(C)[Pb+]CC VEISOORMEMZVJC-UHFFFAOYSA-M 0.000 description 1
- HRVLRJWCMHSVSA-UHFFFAOYSA-D C=NC([S-])=S.[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S Chemical compound C=NC([S-])=S.[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S.C=NC([S-])=S HRVLRJWCMHSVSA-UHFFFAOYSA-D 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000015976 Corneal dystrophy-perceptive deafness syndrome Diseases 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 101000608720 Helianthus annuus 10 kDa late embryogenesis abundant protein Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 101000952180 Morus alba Mulatexin Proteins 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LVSXFUSFHIAQJD-UHFFFAOYSA-N [amino(anilino)methylidene]-phenylazanium 2-hydroxy-2-oxoacetate Chemical compound C(C(=O)O)(=O)O.C1(=CC=CC=C1)NC(=N)NC1=CC=CC=C1 LVSXFUSFHIAQJD-UHFFFAOYSA-N 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- VAAVYQQCYYPTGJ-UHFFFAOYSA-L bis(carbamothioylsulfanyl)lead Chemical compound [Pb+2].NC([S-])=S.NC([S-])=S VAAVYQQCYYPTGJ-UHFFFAOYSA-L 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- 238000013036 cure process Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- YPQOCKOIFRNBQW-UHFFFAOYSA-N dibutylazanium;n,n-dibutylcarbamodithioate Chemical compound CCCCNCCCC.CCCCN(C(S)=S)CCCC YPQOCKOIFRNBQW-UHFFFAOYSA-N 0.000 description 1
- SZRLKIKBPASKQH-UHFFFAOYSA-M dibutyldithiocarbamate Chemical compound CCCCN(C([S-])=S)CCCC SZRLKIKBPASKQH-UHFFFAOYSA-M 0.000 description 1
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- SQEDZTDNVYVPQL-UHFFFAOYSA-N dodecylbenzene;sodium Chemical compound [Na].CCCCCCCCCCCCC1=CC=CC=C1 SQEDZTDNVYVPQL-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 229920006174 synthetic rubber latex Polymers 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
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- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/10—Reinforcing macromolecular compounds with loose or coherent fibrous material characterised by the additives used in the polymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/02—Direct processing of dispersions, e.g. latex, to articles
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/10—Latex
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2309/00—Characterised by the use of homopolymers or copolymers of conjugated diene hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L89/00—Compositions of proteins; Compositions of derivatives thereof
- C08L89/005—Casein
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/1386—Natural or synthetic rubber or rubber-like compound containing
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Moulding By Coating Moulds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
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Description
本件出願は、2001年3月12日に提出された出願番号60/275,087の米国仮特許出願を基礎とする。
天然または合成のゴムラテックスからエラストマー製品を生成するための製造プロセスは、硫黄基を介して架橋または加硫がポリマーユニット間で起こる硬化段階を含んでいる。天然または合成ラテックスからエラストマー製品を製造する従来のプロセスは、一般に、ラテックスの分散液またはエマルジョンを調製し、製造する物品の形状の型をラテックスに浸漬してラテックスを型上で硬化させる工程を含んでいる。引っ張り強度などのエラストマー製品の所望の性質は、製造プロセスの架橋及び硬化段階に実質的に影響を受ける。
本件発明者は、天然ゴムと同様の所望の性質(例えば、引っ張り強度)を有しているが天然ゴムラテックスプロテイン及びアレルゲンは無いエラストマー製品を製造するプロセスにおいてラテックスと共に使用可能な、硫黄架橋可能なポリイソプレンラテックスのための三成分から成る促進剤組成物(three-part accelerator composition)を発見した。他の利点は、この促進剤システムは手袋のような薄く成形されるエラストマー製品が必要とされる医療用途に適していることである。さらに、本発明の促進剤組成物及びプロセスは、溶媒ベースのプロセスシステムとは反対に、溶媒を使わない水ベースのプロセスシステムを使うことを可能とする。得られる製品は、溶媒ベースシステムを用いて製造されるものと同様の性質を有する。従って、本発明によれば、溶媒の使用を減少あるいは避けることができ、また溶剤毒性も同様に避けることができる。
本発明の促進剤組成物は、ポリイソプレンから成るエラストマー製品の製造に使用されることが知られている従来の設備及び材料と共に使用できる。一般に、このプロセスは、配合ポリイソプレンラテックス組成物の調製で始まる。合成ポリイソプレンラテックスは、促進剤組成物、安定化剤及び付加成分と組み合わされて、本発明に従ってポリイソプレンラテックス組成物を調製する。この促進剤の機能は、加硫速度を増加すること、もしくはポリイソプレンを架橋してプロセスの硬化段階中にラテックスの硬化特性を強化することである。この促進剤組成物を含んだ配合ラテックスは、浸漬及び硬化段階の前に、直ぐに用いることもできるし、また浸漬プロセスに使う前に一定期間貯蔵することもできる。
本発明の配合ポリイソプレンラテックス組成物は、以下の手順で調製することができる。
最初に、配合ポリイソプレンラテックスのpHをおよそpH10に調節する。手袋の型をオーブン中で約70℃の温度に予備加熱してから予備調製された凝固剤組成物に約55℃の温度で一定時間浸漬させた後、そこから取り出す。次に、凝固剤被覆された型を、凝固剤を乾燥させるに十分な時間、典型的には約5分、約70℃の乾燥オーブン中に置く。
実施例1
ポリイソプレン手袋の作製
ポリイソプレンラテックス(テキサス州ハウストンのシェルインターナショナルコーポレーションから入手したTSC64.40%を有するクラトン[Kraton、商標]IR PR401、ロット#000313)を水で希釈した。カゼインナトリウム塩(ロードアイランド州ピースダルのテクニカルインダストリーズインコーポレーテド(Technical Industries, Inc.)から入手した)を混合物に添加し、周囲の温度で攪拌した。連続攪拌下で、亜鉛酸化物及び硫黄分散系を混合物に添加した。促進剤化合物ZDEC(オハイオ州アクロンのアクロンディスパージョンから入手)、ZMBT、及びDPG(オハイオ州アクロンのアクロンディスパージョンから入手)を分散系に処方した後に添加した。ウィングステイ[Wingstay、商標]Lを加えた混合物をおよそ15分間攪拌した。この組成物を水で約37.0%固形分に希釈した。pHは水酸化アンモニウムを用いてpH10.7に調節した。この組成物を25℃の温度で維持し、25℃未満の温度で24時間連続攪拌下で貯蔵した。
成分 部(phr)乾燥重量
ポリイソプレン 100.00
ZDEC 0.50
ZMBT 0.50
DPG 1.00
カゼインナトリウム塩 0.75
ZnO 0.50
硫黄 1.25
ウィングスティ(商標)L 2.00
異なる促進剤処方及びプロセス条件を用いた比較データ
配合ポリイソプレンラテックス組成物を変えるとともにプロセスパラメータを変えたものをサンプルの調整に用い、その物理的性質を試験し評価した。種々の促進剤化合物及びphr(100に対する部数)割合を有する配合ラテックスを実施例1のポリイソプレンラテックス組成物の調製プロセスと同様のプロセスに従って調製し、以下の表1に記載かつリストされた対応の温度及び条件で予備硬化させて貯蔵した。
本発明は、ポリイソプレンで組成されるエラストマー製品の製造プロセスに有用である。また、本発明は、天然ゴムラテックスから作られるエラストマー製品の物理的性質に近い合成ポリイソプレン製品を生成する可能性をもたらす。また、本発明は、医療用手袋、コンドーム、プローブカバー、歯科用ダム、指サック、カテーテル等に好適に使用される。
Claims (24)
- a)ジチオカルバメート、チアゾール及びグアニジン化合物を含む促進剤組成物と安定化剤とを含有する配合ラテックス組成物を調製する工程;
b)型を前記配合ラテックス組成物に浸漬する工程;及び
c)前記配合ラテックス組成物を前記型上で硬化させてポリイソプレンエラストマー製品を形成する工程、
を有する、ポリイソプレンエラストマー製品の製造プロセス。 - 前記ポリイソプレンエラストマー製品は手袋である請求項1に記載のプロセス。
- 前記ポリイソプレンエラストマー製品はコンドームである請求項1に記載のプロセス。
- 前記ポリイソプレンエラストマー製品はプローブカバーである請求項1に記載のプロセス。
- 前記ポリイソプレンエラストマー製品はカテーテルである請求項1に記載のプロセス。
- 前記促進剤組成物は、ジエチルジチオカルバミド酸亜鉛、2−メルカプトベンゾチアゾール亜鉛、及びジフェニルグアニジンを含む請求項1に記載のプロセス。
- 前記安定化剤は、ミルクプロティン塩を含む請求項1に記載のプロセス。
- 前記安定化剤は、カゼインナトリウム塩を含む請求項1に記載のプロセス。
- 前記促進剤組成物は、ジチオカルバメート:チアゾール:グアニジンphr比が、前記配合ラテックス組成物のポリイソプレン100phrに対して、ジチオカルバメート0.50phr〜1.00phr:チアゾール0.50phr〜1.00phr:グアニジン0.50phr〜1.00phrである請求項1に記載のプロセス。
- ASTM D412に従って測定される引っ張り強度が3000psiより大きく、下記工程を有するプロセスによって調製されるポリイソプレンエラストマー製品:
a)ジチオカルバメート、チアゾール及びグアニジン化合物を含む促進剤組成物と安定化剤とを含有する配合ラテックス組成物を調製する工程;
b)型を前記配合ラテックス組成物に浸漬する工程;及び
c)前記配合ラテックス組成物を前記型上で硬化させてポリイソプレンエラストマー製品を形成する工程。 - 前記製品は手袋である請求項10に記載のポリイソプレンエラストマー製品。
- 前記製品はコンドームである請求項10に記載のポリイソプレンエラストマー製品。
- 前記製品はプローブカバーである請求項10に記載のポリイソプレンエラストマー製品。
- 前記製品はカテーテルである請求項10に記載のポリイソプレンエラストマー製品。
- 前記促進剤組成物は、ジエチルジチオカルバミド酸亜鉛、2−メルカプトベンゾチアゾール亜鉛、及びジフェニルグアニジンを含む請求項10に記載のポリイソプレンエラストマー製品。
- 前記安定化剤は、ミルクプロティン塩を含む請求項10に記載のポリイソプレンエラストマー製品。
- 前記安定化剤は、カゼインナトリウム塩を含む請求項10に記載のポリイソプレンエラストマー製品。
- 前記促進剤組成物は、ジチオカルバメート:チアゾール:グアニジンphr比が、前記配合ラテックス組成物のポリイソプレン100phrに対して、ジチオカルバメート0.50phr〜1.00phr:チアゾール0.50phr〜1.00phr:グアニジン0.50phr〜1.00phrである請求項10に記載のポリイソプレンエラストマー製品。
- ジチオカルバメート化合物、チアゾール化合物、グアニジン化合物、及び安定化剤を含むポリイソプレンラテックス組成物。
- 前記ラテックス組成物は、ジエチルジチオカルバミド酸亜鉛、2−メルカプトベンゾチアゾール亜鉛、ジフェニルグアニジン、及びカゼインナトリウム塩を含む請求項19に記載のポリイソプレンラテックス組成物。
- ジチオカルバメート化合物、チアゾール化合物、及びグアニジン化合物から成り、前記ジチオカルバメート、前記チアゾール及び前記グアニジンの各々のphr乾燥重量比が、ポリイソプレン100.0部に対して0.50〜1.00の範囲であるポリイソプレンエラストマー製品を作製するためのプロセスに用いる促進剤組成物。
- ポリイソプレンにより組成され、ASTM D412に従って測定される引っ張り強度が3000psiより大きく、ジチオカルバメート化合物、チアゾール化合物及びグアニジン化合物を含むポリイソプレンラテックス組成物から調製される手袋。
- 前記ポリイソプレンラテックス組成物は、さらにカゼインナトリウム塩を有する請求項22に記載の手袋。
- 前記ポリイソプレンラテックス組成物は7日まで貯蔵される請求項22に記載の手袋。
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US27508701P | 2001-03-12 | 2001-03-12 | |
PCT/US2002/007304 WO2002090430A1 (en) | 2001-03-12 | 2002-03-12 | Polyisoprene articles and process for making the same |
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JP2004532752A JP2004532752A (ja) | 2004-10-28 |
JP4116884B2 true JP4116884B2 (ja) | 2008-07-09 |
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JP (1) | JP4116884B2 (ja) |
KR (1) | KR100855259B1 (ja) |
AU (1) | AU2002248590B2 (ja) |
CA (1) | CA2408626C (ja) |
DE (3) | DE10297860B3 (ja) |
ES (1) | ES2219191B1 (ja) |
GB (1) | GB2388372B (ja) |
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- 2002-03-12 DE DE10297860.3A patent/DE10297860B3/de not_active Expired - Lifetime
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- 2002-03-12 WO PCT/US2002/007304 patent/WO2002090430A1/en active IP Right Grant
- 2002-03-12 DE DE10296456.4T patent/DE10296456B4/de not_active Expired - Lifetime
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- 2002-03-12 NZ NZ522334A patent/NZ522334A/en not_active IP Right Cessation
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WO2002090430A1 (en) | 2002-11-14 |
US20020173563A1 (en) | 2002-11-21 |
US8273810B2 (en) | 2012-09-25 |
US20040169317A1 (en) | 2004-09-02 |
GB2388372B (en) | 2004-06-16 |
GB2388372A (en) | 2003-11-12 |
AU2002248590B2 (en) | 2006-06-08 |
US6828387B2 (en) | 2004-12-07 |
DE10296456B4 (de) | 2017-03-09 |
CA2408626C (en) | 2009-02-17 |
DE10297863B3 (de) | 2021-08-26 |
DE10296456T5 (de) | 2004-04-22 |
KR100855259B1 (ko) | 2008-08-29 |
DE10297860B3 (de) | 2016-11-03 |
GB0317582D0 (en) | 2003-08-27 |
KR20030013404A (ko) | 2003-02-14 |
JP2004532752A (ja) | 2004-10-28 |
ES2219191A1 (es) | 2004-11-16 |
CA2408626A1 (en) | 2002-11-14 |
US20090326102A1 (en) | 2009-12-31 |
US20110203596A1 (en) | 2011-08-25 |
ES2219191B1 (es) | 2007-05-01 |
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