JP2004509205A5 - - Google Patents
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- Publication number
- JP2004509205A5 JP2004509205A5 JP2002526981A JP2002526981A JP2004509205A5 JP 2004509205 A5 JP2004509205 A5 JP 2004509205A5 JP 2002526981 A JP2002526981 A JP 2002526981A JP 2002526981 A JP2002526981 A JP 2002526981A JP 2004509205 A5 JP2004509205 A5 JP 2004509205A5
- Authority
- JP
- Japan
- Prior art keywords
- biodegradable polymer
- group
- phenol
- halo
- alkoxy
- 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.)
- Granted
Links
- 229920002988 biodegradable polymer Polymers 0.000 description 52
- 239000004621 biodegradable polymer Substances 0.000 description 52
- 239000000203 mixture Substances 0.000 description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 30
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 125000001475 halogen functional group Chemical group 0.000 description 27
- 125000001424 substituent group Chemical group 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 125000002947 alkylene group Chemical group 0.000 description 18
- 125000002993 cycloalkylene group Chemical group 0.000 description 18
- 125000005702 oxyalkylene group Chemical group 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229920001634 Copolyester Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000005011 phenolic resin Substances 0.000 description 7
- 150000003505 terpenes Chemical class 0.000 description 7
- 235000007586 terpenes Nutrition 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid group Chemical group C(CC(=O)O)(=O)O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 229940043375 1,5-pentanediol Drugs 0.000 description 3
- GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-UHFFFAOYSA-N 0.000 description 3
- -1 5-t-butylphenylthio Chemical group 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- 229920003232 aliphatic polyester Polymers 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000003605 opacifier Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 2
- CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 description 2
- QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical group OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical group O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012748 slip agent Substances 0.000 description 2
- HGYMQZVPTMKXGI-UHFFFAOYSA-N 1-(2-hydroxynaphthalen-1-yl)sulfanylnaphthalen-2-ol Chemical compound C1=CC=C2C(SC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 HGYMQZVPTMKXGI-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/662,965 US6767972B1 (en) | 2000-09-15 | 2000-09-15 | Methods for slowing the degradation rate of biodegradable polymers and biodegradable polymer compositions and compositions thereof |
| US09/662,965 | 2000-09-15 | ||
| PCT/US2001/020065 WO2002022737A2 (en) | 2000-09-15 | 2001-06-22 | Methods for slowing the degradation rate of biodegradable polymer and biodegradable polymer compositions and compositions thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004509205A JP2004509205A (ja) | 2004-03-25 |
| JP2004509205A5 true JP2004509205A5 (enExample) | 2008-04-10 |
| JP5053500B2 JP5053500B2 (ja) | 2012-10-17 |
Family
ID=24659955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002526981A Expired - Fee Related JP5053500B2 (ja) | 2000-09-15 | 2001-06-22 | 生分解性ポリマー及び生分解性ポリマー組成物の分解速度の減速方法並びにそれらの組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6767972B1 (enExample) |
| EP (1) | EP1317506B1 (enExample) |
| JP (1) | JP5053500B2 (enExample) |
| AT (1) | ATE312876T1 (enExample) |
| DE (1) | DE60115922T2 (enExample) |
| WO (1) | WO2002022737A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4987260B2 (ja) * | 2005-07-12 | 2012-07-25 | 株式会社クレハ | ポリグリコール酸樹脂成形物 |
| BRPI0600685A (pt) * | 2006-02-24 | 2007-11-20 | Phb Ind Sa | blenda polimérica ambientalmente degradável e seu processo de obtenção |
| US8507234B2 (en) * | 2006-06-16 | 2013-08-13 | Polymer Ventures, Inc. | Composition and methods for improving the production of fermentation operations |
| WO2007149327A2 (en) * | 2006-06-16 | 2007-12-27 | Polymer Ventures, Inc. | Composition and methods for improving the production of fermentation operations |
| US20080146444A1 (en) * | 2006-12-19 | 2008-06-19 | Polymer Ventures, Inc. | Method and compositions for improving plant growth |
| US7803360B2 (en) * | 2007-04-30 | 2010-09-28 | Biobait, Inc. | Water-degradable fishing lure |
| CN101298512B (zh) * | 2007-04-30 | 2011-07-27 | 刘原珊 | Pva-pcl-淀粉共混材料及其制备方法 |
| WO2009137058A1 (en) | 2008-05-06 | 2009-11-12 | Metabolix, Inc. | Biodegradable polyester blends |
| JP5577764B2 (ja) * | 2009-07-06 | 2014-08-27 | 株式会社リコー | 共重合樹脂組成物、成形品、及び共重合樹脂組成物の製造方法 |
| FI126885B (fi) * | 2011-05-31 | 2017-07-14 | Stora Enso Oyj | Terpeenifenolihartsin käyttö ekstruusiopinnoituksessa |
| US9475930B2 (en) | 2012-08-17 | 2016-10-25 | Metabolix, Inc. | Biobased rubber modifiers for polymer blends |
| WO2014194220A1 (en) | 2013-05-30 | 2014-12-04 | Metabolix, Inc. | Recyclate blends |
| KR20140143045A (ko) * | 2013-06-05 | 2014-12-15 | 삼성정밀화학 주식회사 | 생분해성 폴리에스테르 수지 및 이를 포함하는 물품 |
| CN103342879B (zh) * | 2013-07-26 | 2015-06-17 | 四川川庆井下科技有限公司 | 一种可降解暂堵球 |
| US10611903B2 (en) | 2014-03-27 | 2020-04-07 | Cj Cheiljedang Corporation | Highly filled polymer systems |
| JP7257342B2 (ja) | 2018-02-08 | 2023-04-13 | テルモ株式会社 | 医療器具およびこれを用いた癒合促進デバイス |
| US11065003B2 (en) | 2018-03-19 | 2021-07-20 | Terumo Kabushiki Kaisha | Treatment method for joining biological organs |
| CN112638287A (zh) | 2018-09-27 | 2021-04-09 | 泰尔茂株式会社 | 愈合促进器具以及医疗设备 |
| WO2020067372A1 (ja) | 2018-09-27 | 2020-04-02 | テルモ株式会社 | 癒合促進デバイス |
| CN113490458A (zh) | 2019-03-28 | 2021-10-08 | 泰尔茂株式会社 | 愈合促进设备 |
| CN113646016B (zh) | 2019-03-28 | 2023-07-11 | 泰尔茂株式会社 | 医疗器械 |
| CN113573666A (zh) | 2019-03-28 | 2021-10-29 | 泰尔茂株式会社 | 愈合促进器具 |
| CN113573747B (zh) | 2019-03-28 | 2023-02-24 | 泰尔茂株式会社 | 医疗器具 |
| JPWO2023032692A1 (enExample) | 2021-09-03 | 2023-03-09 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1012045A (en) | 1961-04-20 | 1965-12-08 | Tenneco Chem | Improvements in or relating to terpene-phenol condensation products |
| JPS61145255A (ja) * | 1984-12-19 | 1986-07-02 | Hitachi Chem Co Ltd | 安定化された合成樹脂組成物 |
| ATE199383T1 (de) | 1990-11-30 | 2001-03-15 | Eastman Chem Co | Aliphatisch-aromatische copolyester |
| US5292783A (en) | 1990-11-30 | 1994-03-08 | Eastman Kodak Company | Aliphatic-aromatic copolyesters and cellulose ester/polymer blends |
| US5169889A (en) * | 1992-01-27 | 1992-12-08 | National Starch And Chemical Investment Holding Corporation | Poly hydroxybutyrate/hydroxyvalerate based hot melt adhesive |
| JP3330390B2 (ja) | 1992-06-11 | 2002-09-30 | 三井化学株式会社 | ホットメルト接着剤組成物 |
| US5312850A (en) | 1993-01-04 | 1994-05-17 | National Starch And Chemical Investment Holding Corporation | Polylactide and starch containing hot melt adhesive |
| US5252646A (en) * | 1992-10-29 | 1993-10-12 | National Starch And Chemical Investment Holding Corporation | Polylactide containing hot melt adhesive |
| JPH06212067A (ja) * | 1993-01-18 | 1994-08-02 | Toray Ind Inc | 難燃性ポリエステル樹脂組成物およびその射出成形品 |
| US5480962A (en) | 1993-07-22 | 1996-01-02 | Eastman Chemical Company | Copolyesters having repeat units derived from succinic acid |
| GB2281709B (en) * | 1993-09-14 | 1998-04-08 | Fujitsu Ltd | Biodegradable resin moulded article |
| CA2195787A1 (en) * | 1994-08-12 | 1996-02-22 | Denise R. Rutherford | Poly(.beta.-hydroxyorganoate) pressure sensitive adhesive compositions |
| US5457175A (en) * | 1995-01-11 | 1995-10-10 | Arizona Chemical Company | Low softening point terpene-phenol resins |
| US5583187A (en) * | 1995-05-03 | 1996-12-10 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives based on hydroxy-functional polyesters |
| US5750605A (en) * | 1995-08-31 | 1998-05-12 | National Starch And Chemical Investment Holding Corporation | Hot melt adhesives based on sulfonated polyesters |
| US5952405A (en) * | 1997-08-26 | 1999-09-14 | National Starch And Chemical Investment Holding Corporation | Lactide graft copolymers and hot melt adhesives prepared from same |
| JP2000007903A (ja) | 1998-06-25 | 2000-01-11 | Shimadzu Corp | ポリ乳酸系組成物及び成形品 |
| JP2001049098A (ja) * | 1999-08-10 | 2001-02-20 | Mitsui Chemicals Inc | 乳酸系樹脂組成物及び成形体 |
-
2000
- 2000-09-15 US US09/662,965 patent/US6767972B1/en not_active Expired - Fee Related
-
2001
- 2001-06-22 EP EP01946687A patent/EP1317506B1/en not_active Expired - Lifetime
- 2001-06-22 DE DE60115922T patent/DE60115922T2/de not_active Expired - Lifetime
- 2001-06-22 JP JP2002526981A patent/JP5053500B2/ja not_active Expired - Fee Related
- 2001-06-22 WO PCT/US2001/020065 patent/WO2002022737A2/en not_active Ceased
- 2001-06-22 AT AT01946687T patent/ATE312876T1/de not_active IP Right Cessation
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