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Patent · US9493599B2 · B2 · US

Modified polymer

(11) Publication number
US9493599B2
(21) Application number
14/443,371
(22) Filing date
2013-11-15
(30) Priority date
2012-11-16
(43) Publication date
2016-11-15
(45) Date of grant
2016-11-15
(51) IPC
C08F 236/10; B60C 1/00; C08C 19/22; C08F 8/30
(52) CPC
  • C08F Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds: 236/10, 8/30
  • B60C Vehicle tyres; tyre inflation; tyre changing; connecting valves to inflatable elastic bodies in general; devices or arrangements related to tyres: 1/00
  • C08C Treatment or chemical modification of rubbers: 19/22
  • C08K Use of inorganic or non-macromolecular organic substances as compounding ingredients: 5/32
(73) Assignee
Yokohama Rubber Co Ltd
(72) Inventors
Ryota Takahashi; Takahiro Okamatsu
(54) Title
Modified polymer
(57) Abstract

The present technology provides a modified polymer which is modified with two or more types of nitrones that include a nitrone having at least one carboxy group and a nitrone having no carboxy group.

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Claims (15)

  1. A modified polymer that is modified with two or more types of nitrones including (A) a nitrone having at least one carboxy group and (B) a nitrone having no carboxy group.
  2. The modified polymer according to claim 1, wherein the nitrone (B) is a nitrone having at least one aromatic hydrocarbon group.
  3. The modified polymer according to claim 1, wherein the nitrone (A) is a nitrone represented by formula (a) below: wherein, m and n each independently represent integers of 0 to 5, and a sum of m and n is 1 or greater.
  4. The modified polymer according to claim 1, wherein the nitrone (B) is a nitrone represented by formula (b) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.
  5. The modified polymer according to claim 1, wherein the modified polymer contains a five-membered ring structure represented by formula (I) below: wherein, m and n each independently represent integers of 0 to 5, and a sum of m and n is 1 or greater.
  6. The modified polymer according to claim 1, wherein the modified polymer contains a five-membered ring structure represented by formula (II) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.
  7. The modified polymer according to claim 1, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.
  8. The modified polymer according to claim 2, wherein the nitrone (A) is a nitrone represented by formula (a) below: wherein, m and n each independently represent integers of 0 to 5, and a sum of m and n is 1 or greater.
  9. The modified polymer according to claim 3, wherein the nitrone (B) is a nitrone represented by formula (b) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.
  10. The modified polymer according to claim 5, wherein the modified polymer contains a five-membered ring structure represented by formula (II) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.
  11. The modified polymer according to claim 2, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.
  12. The modified polymer according to claim 3, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.
  13. The modified polymer according to claim 4, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.
  14. The modified polymer according to claim 8, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.
  15. The modified polymer according to claim 9, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.

Description

The present technology relates to modified polymers.

Modified polymers that are modified by various nitrones have been known conventionally as polymers contained in rubber compositions for use in tires and the like (see, e.g., Japanese Examined Patent Application Publication No. S47-25712A, and Japanese Unexamined Patent Application Publication Nos. S48-16996A and 2007-70439A).

The present inventors have found that, even though cases where a modified polymer that is modified with a nitrone having a carboxy group enhances the value of tan δ (60° C.), and even though cases where a modified polymer that is modified with a nitrone having no carboxy group (e.g. diphenylnitrone) enhances the value of tan δ (0° C.), compared to a case where an unmodified polymer is used, tensile properties such as tensile strength (T B) and/or elongation at break (E B) are significantly lowered in both the cases.

Note that tan δ (0° C.) and tan δ (60° C.), which are loss tangents (loss factors), are known as an indicator of wet grip performance and an indicator of rolling resistance, respectively.

The present technology provides a modified polymer which enhances the tensile properties and loss tangent of a vulcanized product when the modified polymer is used in the vulcanized product.

The present inventors have found that a vulcanized product formed with a modified polymer that is modified with two or more types of specific nitrones can achieve excellent values of tan δ (0° C.) and tan δ (60° C.) while suppressing the lowering of tensile properties, and thus completed the present technology.

Citations (3)

  • US3792031A
  • US20070004869A1
  • JP2007070439A
Record as JSON
{
  "publication_number": "US9493599B2",
  "country": "US",
  "kind": "B2",
  "title": "Modified polymer",
  "abstract": "The present technology provides a modified polymer which is modified with two or more types of nitrones that include a nitrone having at least one carboxy group and a nitrone having no carboxy group.",
  "claims": [
    "1. A modified polymer that is modified with two or more types of nitrones including (A) a nitrone having at least one carboxy group and (B) a nitrone having no carboxy group.",
    "2. The modified polymer according to claim 1, wherein the nitrone (B) is a nitrone having at least one aromatic hydrocarbon group.",
    "3. The modified polymer according to claim 1, wherein the nitrone (A) is a nitrone represented by formula (a) below: wherein, m and n each independently represent integers of 0 to 5, and a sum of m and n is 1 or greater.",
    "4. The modified polymer according to claim 1, wherein the nitrone (B) is a nitrone represented by formula (b) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.",
    "5. The modified polymer according to claim 1, wherein the modified polymer contains a five-membered ring structure represented by formula (I) below: wherein, m and n each independently represent integers of 0 to 5, and a sum of m and n is 1 or greater.",
    "6. The modified polymer according to claim 1, wherein the modified polymer contains a five-membered ring structure represented by formula (II) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.",
    "7. The modified polymer according to claim 1, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.",
    "8. The modified polymer according to claim 2, wherein the nitrone (A) is a nitrone represented by formula (a) below: wherein, m and n each independently represent integers of 0 to 5, and a sum of m and n is 1 or greater.",
    "9. The modified polymer according to claim 3, wherein the nitrone (B) is a nitrone represented by formula (b) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.",
    "10. The modified polymer according to claim 5, wherein the modified polymer contains a five-membered ring structure represented by formula (II) below: wherein, X and Y each independently represent aliphatic or aromatic hydrocarbon groups optionally having a substituent other than a carboxy group, and at least one of X or Y represents an aromatic hydrocarbon group optionally having a substituent other than a carboxy group.",
    "11. The modified polymer according to claim 2, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.",
    "12. The modified polymer according to claim 3, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.",
    "13. The modified polymer according to claim 4, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.",
    "14. The modified polymer according to claim 8, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100.",
    "15. The modified polymer according to claim 9, wherein a molar ratio (A/B) of the nitrone (A) to the nitrone (B) is from 1/1 to 1/100."
  ],
  "description_excerpt": "The present technology relates to modified polymers.\n\nModified polymers that are modified by various nitrones have been known conventionally as polymers contained in rubber compositions for use in tires and the like (see, e.g., Japanese Examined Patent Application Publication No. S47-25712A, and Japanese Unexamined Patent Application Publication Nos. S48-16996A and 2007-70439A).\n\nThe present inventors have found that, even though cases where a modified polymer that is modified with a nitrone having a carboxy group enhances the value of tan δ (60° C.), and even though cases where a modified polymer that is modified with a nitrone having no carboxy group (e.g. diphenylnitrone) enhances the value of tan δ (0° C.), compared to a case where an unmodified polymer is used, tensile properties such as tensile strength (T B) and/or elongation at break (E B) are significantly lowered in both the cases.\n\nNote that tan δ (0° C.) and tan δ (60° C.), which are loss tangents (loss factors), are known as an indicator of wet grip performance and an indicator of rolling resistance, respectively.\n\nThe present technology provides a modified polymer which enhances the tensile properties and loss tangent of a vulcanized product when the modified polymer is used in the vulcanized product.\n\nThe present inventors have found that a vulcanized product formed with a modified polymer that is modified with two or more types of specific nitrones can achieve excellent values of tan δ (0° C.) and tan δ (60° C.) while suppressing the lowering of tensile properties, and thus completed the present technology.",
  "cpc": [
    "C08F 236/10",
    "B60C 1/00",
    "C08C 19/22",
    "C08F 8/30",
    "C08K 5/32"
  ],
  "ipc": [
    "C08F 236/10",
    "B60C 1/00",
    "C08C 19/22",
    "C08F 8/30"
  ],
  "assignees": [
    "Yokohama Rubber Co Ltd"
  ],
  "inventors": [
    "Ryota Takahashi",
    "Takahiro Okamatsu"
  ],
  "filing_date": "2013-11-15",
  "publication_date": "2016-11-15",
  "grant_date": "2016-11-15",
  "priority_date": "2012-11-16",
  "application_number": "US-201314443371-A",
  "family_id": "50731273",
  "cited_by_count": 7,
  "citations": [
    "US3792031A",
    "US20070004869A1",
    "JP2007070439A"
  ]
}

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