CA2134462C - Greffage de monomeres sur des polyolefines en presence de peroxydes organiques - Google Patents

Greffage de monomeres sur des polyolefines en presence de peroxydes organiques Download PDF

Info

Publication number: CA2134462C
Authority: CA; Canada
Prior art keywords: polyolefin; organic peroxide; grafting; carrier polymer; ethylene
Prior art date: 1993-04-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002134462A

Other languages

English (en)

Other versions

CA2134462A1 (fr

Inventor

Peter Yates Kelly

David John Mitchell

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1993-04-27

Filing date

1994-04-22

Publication date

2005-11-15

1993-04-27 Priority claimed from GB939308669A external-priority patent/GB9308669D0/en

1994-04-22 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1994-10-28 Publication of CA2134462A1 publication Critical patent/CA2134462A1/fr

2005-11-15 Application granted granted Critical

2005-11-15 Publication of CA2134462C publication Critical patent/CA2134462C/fr

2014-04-22 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920000098 polyolefin Polymers 0.000 title claims abstract description 88
150000001451 organic peroxides Chemical class 0.000 title claims abstract description 66
239000000178 monomer Substances 0.000 title claims abstract description 41
229920000642 polymer Polymers 0.000 claims abstract description 94
238000000034 method Methods 0.000 claims abstract description 39
238000002844 melting Methods 0.000 claims abstract description 18
230000008018 melting Effects 0.000 claims abstract description 18
229920001112 grafted polyolefin Polymers 0.000 claims abstract description 15
238000004132 cross linking Methods 0.000 claims abstract description 14
238000012668 chain scission Methods 0.000 claims abstract description 12
230000000694 effects Effects 0.000 claims abstract description 3
239000005977 Ethylene Substances 0.000 claims description 24
229920001577 copolymer Polymers 0.000 claims description 20
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 19
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 10
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
239000004711 α-olefin Substances 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 7
-1 vinyl halides Chemical class 0.000 claims description 7
150000001735 carboxylic acids Chemical class 0.000 claims description 6
229920001155 polypropylene Polymers 0.000 claims description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
229920002554 vinyl polymer Polymers 0.000 claims description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
229920001519 homopolymer Polymers 0.000 claims description 4
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
229920000554 ionomer Polymers 0.000 claims description 3
229920005606 polypropylene copolymer Polymers 0.000 claims description 3
150000004756 silanes Chemical class 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical class C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 2
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 2
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
239000004743 Polypropylene Substances 0.000 claims description 2
239000004793 Polystyrene Substances 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
229920001400 block copolymer Polymers 0.000 claims description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
150000001993 dienes Chemical class 0.000 claims description 2
IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical class CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 claims description 2
MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical class [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 claims description 2
FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical class CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical class CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims description 2
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
229920002223 polystyrene Polymers 0.000 claims description 2
VRVKOZSIJXBAJG-ODZAUARKSA-M sodium;(z)-but-2-enedioate;hydron Chemical class [Na+].OC(=O)\C=C/C([O-])=O VRVKOZSIJXBAJG-ODZAUARKSA-M 0.000 claims description 2
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
229920001567 vinyl ester resin Polymers 0.000 claims description 2
KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical class O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 claims 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
150000001805 chlorine compounds Chemical class 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
239000011976 maleic acid Substances 0.000 claims 1
JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical class O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 claims 1
239000000499 gel Substances 0.000 abstract description 26
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
239000000155 melt Substances 0.000 description 18
150000008064 anhydrides Chemical class 0.000 description 13
229940117958 vinyl acetate Drugs 0.000 description 9
DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 7
239000000356 contaminant Substances 0.000 description 6
229920001038 ethylene copolymer Polymers 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
238000001125 extrusion Methods 0.000 description 4
238000002156 mixing Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 3
239000002245 particle Substances 0.000 description 3
229920000573 polyethylene Polymers 0.000 description 3
239000000654 additive Substances 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000008188 pellet Substances 0.000 description 2
ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920003345 Elvax® Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
229920003298 Nucrel® Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920003182 Surlyn® Polymers 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
XRERONKQLIQWGW-UHFFFAOYSA-N but-1-ene;styrene Chemical compound CCC=C.C=CC1=CC=CC=C1 XRERONKQLIQWGW-UHFFFAOYSA-N 0.000 description 1
FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
VYBFJKPXWYJWMF-UHFFFAOYSA-N hexane octane Chemical compound CCCCCC.CCCCCC.CCCCCCCC.CCCCCCCC VYBFJKPXWYJWMF-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229920006132 styrene block copolymer Polymers 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 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

Landscapes

Graft Or Block Polymers (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA002134462A 1993-04-27 1994-04-22 Greffage de monomeres sur des polyolefines en presence de peroxydes organiques Expired - Fee Related CA2134462C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB9308669.2		1993-04-27
GB939308669A GB9308669D0 (en)	1993-04-27	1993-04-27	Grafting of monomers onto polyolefins in presence of organic peroxides
PCT/CA1994/000224 WO1994025498A1 (fr)	1993-04-27	1994-04-22	Greffe de monomeres sur des polyolefines en presence de peroxydes organiques
US08/234,959 US6331595B1 (en)	1993-04-27	1994-04-28	Grafting of monomers onto polyolefins in presence of organic peroxides

Publications (2)

Publication Number	Publication Date
CA2134462A1 CA2134462A1 (fr)	1994-10-28
CA2134462C true CA2134462C (fr)	2005-11-15

Family

ID=35520880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002134462A Expired - Fee Related CA2134462C (fr)	1993-04-27	1994-04-22	Greffage de monomeres sur des polyolefines en presence de peroxydes organiques

Country Status (1)

Country	Link
CA (1)	CA2134462C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116731254A (zh) *	2023-07-10	2023-09-12	余姚中国塑料城塑料研究院有限公司	一种接枝聚烯烃组合物反应挤出制备方法

1994
- 1994-04-22 CA CA002134462A patent/CA2134462C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2134462A1 (fr)	1994-10-28

Legal Events

Date	Code	Title	Description
2001-04-23	EEER	Examination request
2010-04-22	MKLA	Lapsed

Publication	Publication Date	Title
EP0647246B1 (fr)	1999-01-20	Greffe de monomeres sur des polyolefines en presence de peroxydes organiques
CA1249383A (fr)	1989-01-24	Melanges de polyolefines et de polymeres a teneur d'agents reactifs
EP0072750B1 (fr)	1990-05-02	Composition améliorée de polyéthylène
US4737547A (en)	1988-04-12	Polyolefin blends containing reactive agents
US4612155A (en)	1986-09-16	Process for the grafting of monomers onto polyolefins
US5698617A (en)	1997-12-16	Concentrates suitable for the preparation of functionalized polyolefins and functionalization process using said concentrates
US5969050A (en)	1999-10-19	Continuous process for grafting a polyolefin, the grafted polyolefins obtained by means of this process
US6114486A (en)	2000-09-05	Rheology-modified polyolefins
US5073598A (en)	1991-12-17	Method for improving the processing characteristics of polyethylene blends
JPH08509772A (ja)	1996-10-15	グラフト改質した実質的に線状であるエチレンポリマー類と他の熱可塑性ポリマー類とのブレンド物
US5331046A (en)	1994-07-19	Polyolefinic resin composition having superior paintability
EP0266994A2 (fr)	1988-05-11	Procédé de greffage de monomères sur des polymères
EP0852603B1 (fr)	1999-11-24	Procede de production d'une polyolefine a reticulation par du silane
CA2003615A1 (fr)	1990-05-23	Production de compositions ameliorees de polypropylene au moyen d'une extrudeuse a vis sans fin jumelees non engrenees
JP5048908B2 (ja)	2012-10-17	改良された色を有する無水物でグラフトされたポリマーを調製する方法
JP3290396B2 (ja)	2002-06-10	シラン架橋ポリオレフィンの製造方法
CA1262979A (fr)	1989-11-14	Melanges polyolefiniques renfermant des agents reactifs
JPS59230205A (ja)	1984-12-24	半導電性組成物
CA2134462A1 (fr)	1994-10-28	Greffage de monomeres sur des polyolefines en presence de peroxydes organiques
JPS6187740A (ja)	1986-05-06	ポリオレフインブレンド物
CA2076249A1 (fr)	1994-02-18	Composition copolymerique reticulable par un silane
JPS6086702A (ja)	1985-05-16	半導電性組成物
JPH073082A (ja)	1995-01-06	ポリオレフィン系樹脂組成物