CA2353607C - Compose de pellicule de latex ayant une meilleure resistance a la dechirure - Google Patents

Compose de pellicule de latex ayant une meilleure resistance a la dechirure Download PDF

Info

Publication number: CA2353607C
Authority: CA; Canada
Prior art keywords: antioxidant; latex; compound; mercaptotoluimidazole; zinc
Prior art date: 2001-07-23
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

CA 2353607

Other languages

English (en)

Other versions

CA2353607A1 (fr

Inventor

Robert Thomas Dzikowicz

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.)

Vanderbilt Chemicals LLC

Original Assignee

RT Vanderbilt Co Inc

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.)

2001-07-23

Filing date

2001-07-23

Publication date

2010-09-14

2001-07-23 Application filed by RT Vanderbilt Co Inc filed Critical RT Vanderbilt Co Inc

2001-07-23 Priority to CA 2353607 priority Critical patent/CA2353607C/fr

2003-01-23 Publication of CA2353607A1 publication Critical patent/CA2353607A1/fr

2010-09-14 Application granted granted Critical

2010-09-14 Publication of CA2353607C publication Critical patent/CA2353607C/fr

2021-07-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920000126 latex Polymers 0.000 title claims abstract description 38
239000004816 latex Substances 0.000 title claims abstract description 38
150000001875 compounds Chemical class 0.000 title claims abstract description 29
239000003963 antioxidant agent Substances 0.000 claims abstract description 65
230000003078 antioxidant effect Effects 0.000 claims abstract description 60
UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 claims abstract description 27
229920000642 polymer Polymers 0.000 claims abstract description 11
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims abstract description 8
230000000087 stabilizing effect Effects 0.000 claims abstract description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 5
239000000047 product Substances 0.000 claims description 18
239000002530 phenolic antioxidant Substances 0.000 claims description 14
244000043261 Hevea brasiliensis Species 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
229920003052 natural elastomer Polymers 0.000 claims description 12
229920001194 natural rubber Polymers 0.000 claims description 12
-1 ethylene propylene diene Chemical class 0.000 claims description 10
150000001412 amines Chemical group 0.000 claims description 9
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Polymers C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
239000002174 Styrene-butadiene Substances 0.000 claims description 3
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
229920002681 hypalon Polymers 0.000 claims description 3
229920001084 poly(chloroprene) Polymers 0.000 claims description 3
239000011115 styrene butadiene Substances 0.000 claims description 3
229920003048 styrene butadiene rubber Polymers 0.000 claims description 3
150000003751 zinc Chemical class 0.000 claims description 3
239000012190 activator Substances 0.000 abstract description 8
239000004971 Cross linker Substances 0.000 abstract description 7
239000011701 zinc Substances 0.000 abstract description 5
229910052725 zinc Inorganic materials 0.000 abstract description 5
230000003679 aging effect Effects 0.000 abstract description 3
LLZHXQRNOOAOFF-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione;zinc Chemical compound [Zn].C1=CC=C2NC(S)=NC2=C1 LLZHXQRNOOAOFF-UHFFFAOYSA-N 0.000 abstract description 2
230000002708 enhancing effect Effects 0.000 abstract 1
235000006708 antioxidants Nutrition 0.000 description 57
238000012360 testing method Methods 0.000 description 33
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
230000032683 aging Effects 0.000 description 12
230000000694 effects Effects 0.000 description 11
239000011787 zinc oxide Substances 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
239000012990 dithiocarbamate Substances 0.000 description 10
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 8
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 8
QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 8
235000019333 sodium laurylsulphate Nutrition 0.000 description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
150000002989 phenols Chemical class 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
229920003051 synthetic elastomer Polymers 0.000 description 7
239000005061 synthetic rubber Substances 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 5
229920001971 elastomer Polymers 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000005060 rubber Substances 0.000 description 5
239000003381 stabilizer Substances 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
229920005601 base polymer Polymers 0.000 description 4
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
229960002447 thiram Drugs 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
150000004659 dithiocarbamates Chemical class 0.000 description 2
229920006173 natural rubber latex Polymers 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
238000004088 simulation Methods 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
235000021355 Stearic acid Nutrition 0.000 description 1
239000000654 additive Substances 0.000 description 1
229940071162 caseinate Drugs 0.000 description 1
238000012668 chain scission Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000003292 glue Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
239000003607 modifier Substances 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
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
230000000063 preceeding effect Effects 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
238000004073 vulcanization Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000012991 xanthate Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
229940105296 zinc peroxide Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
- 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
- C08J5/18—Manufacture of films or sheets
- 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
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
- 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
- C08J2321/00—Characterised by the use of unspecified rubbers
- C08J2321/02—Latex

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
Materials Engineering (AREA)
Manufacture Of Macromolecular Shaped Articles (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA 2353607 2001-07-23 2001-07-23 Compose de pellicule de latex ayant une meilleure resistance a la dechirure Expired - Fee Related CA2353607C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2353607 CA2353607C (fr)	2001-07-23	2001-07-23	Compose de pellicule de latex ayant une meilleure resistance a la dechirure

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2353607 CA2353607C (fr)	2001-07-23	2001-07-23	Compose de pellicule de latex ayant une meilleure resistance a la dechirure

Publications (2)

Publication Number	Publication Date
CA2353607A1 CA2353607A1 (fr)	2003-01-23
CA2353607C true CA2353607C (fr)	2010-09-14

Family

ID=4169535

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2353607 Expired - Fee Related CA2353607C (fr)	2001-07-23	2001-07-23	Compose de pellicule de latex ayant une meilleure resistance a la dechirure

Country Status (1)

Country	Link
CA (1)	CA2353607C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7048977B2 (en)	2001-07-18	2006-05-23	R.T. Vanderbilt Company, Inc.	Latex film compound with improved tear resistance
CN115820164A (zh) *	2022-11-08	2023-03-21	张家港爱科思汽车配件有限公司	一种汽车用抗震胶黏剂

2001
- 2001-07-23 CA CA 2353607 patent/CA2353607C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2353607A1 (fr)	2003-01-23

Legal Events

Date	Code	Title	Description
2006-04-11	EEER	Examination request
2018-09-03	MKLA	Lapsed	Effective date: 20180723

Publication	Publication Date	Title
EP3575345B1 (fr)	2022-05-11	Procédé de production de caoutchouc acrylique
US5684082A (en)	1997-11-04	Use of maleated styrene-ethylene-butylene-styrene triblock polymer for improved adhesion
EP3533807B1 (fr)	2023-03-15	Procédé de fabrication de caoutchouc acrylique
US6653380B2 (en)	2003-11-25	Latex film compound with improved tear resistance
US7048977B2 (en)	2006-05-23	Latex film compound with improved tear resistance
US5217807A (en)	1993-06-08	Metal acrylates as rubber-to-metal adhesion promoters
JPWO2017221881A1 (ja)	2019-04-11	難燃ゴム組成物、その加硫物及び成形品
US4119588A (en)	1978-10-10	Reversion resistant rubber compositions with thio carbamyl sulfenamides
US7005467B2 (en)	2006-02-28	Ethylene propylene copolymer composition and process for producing vulcanizates therefor
US2367827A (en)	1945-01-23	Accelerator for vulcanization of rubber
US2453689A (en)	1948-11-16	Vulcanizing synthetic rubber with dixanthic sulfides
US2945834A (en)	1960-07-19	Vulcanizable rubber composition and process for vulcanizing same
US2415029A (en)	1947-01-28	Sulfenamides
US2130242A (en)	1938-09-13	Vulcanization of rubber
US2518576A (en)	1950-08-15	Vulcanization of isobutylene rubber
US2284578A (en)	1942-05-26	Vulcanizable rubber compositions
MX2007012657A (es)	2008-01-11	Composicion y metodo para curar compuestos de latex.
WO1990008170A1 (fr)	1990-07-26	Acrylates metalliques utilises en tant que promoteurs d'adhesion caoutchouc-sur-metal
US2375042A (en)	1945-05-01	Stabilized butadiene-1,3 polymers
US3533979A (en)	1970-10-13	Thermally curable elastomer compositions and additive therefor
US4866138A (en)	1989-09-12	Vulcanization accelerators
JPS6114239A (ja)	1986-01-22	硬化ゴム配合物ならびにその製造法
WO2010084506A2 (fr)	2010-07-29	Nouveaux accélérateurs sulfénamides pour le remplacement de l'accélérateur sulfénamide classique dcbs (dicyclohexylbenzothiazolesulfénamide) dans un composé de calandrage de câblé métallique (enrobage de câble)
JPH0616871A (ja)	1994-01-25	キュア可能な組成物及びキュアエラストマーを得るためのその使用
US2264758A (en)	1941-12-02	Vulcanization of rubber