IP Library Granted Patent US 11,248,079
Granted Patent B2
US 11,248,079 · App. 16/089,323 · Granted Feb 15, 2022

Photocurable resin, mixture, and photocurable resin composition

Inventors: Tsubasa Ito (Hiratsuka, JP); Takeaki Saiki (Hiratsuka, JP); Kazunori Ishikawa (Hiratsuka, JP)
C08F290/067C08F2/48C08G18/672C08G18/69
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Quick Facts
Patent No.
US 11,248,079
App. No.
16/089,323
Granted
Feb 15, 2022
Kind
B2
Abstract

A photocurable resin of the present technology contains: a main backbone chain having repeating units represented by Formulas (Ia) and (Ib), and a (meth)acryloyl group and a non-photoreactive group at terminals; the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom; a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group; a content of the repeating unit represented by Formula (Ia) being greater than 15 mol % of an amount of the main backbone chain; and contents of the (meth)acryloyl group and the non-photoreactive group each being 5 mol % or greater of an amount of the ends.

Claims (78)

1. A photocurable resin comprising:

a main backbone chain having repeating units represented by Formulas (Ia) and (Ib), and a (meth)acryloyl group and a non-photoreactive group at terminals;

the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom;

a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group;

a content of the repeating unit represented by Formula (Ia) being greater than 15 mol % of an amount of the repeating units constituting the main backbone chain;

a content of the (meth)acryloyl group being 5 mol % or greater of an amount of the terminals; and

a content of the non-photoreactive group being 5 mol % or greater of the amount of the terminals:

wherein, a double line of a dashed line and a solid line represents a single bond or a double bond.

2. The photocurable resin according to claim 1 , wherein the non-photoreactive group is a saturated hydrocarbon group which optionally has an ether bond.

3. The photocurable resin according to claim 1 , wherein the non-photoreactive group is formed from at least one type of hydroxy compound selected from the group consisting of

a monofunctional alcohol,

a saturated hydrocarbon compound having one hydroxy group and a heteroatom, and

an aromatic hydrocarbon compound having one hydroxy group and optionally having a heteroatom; and

a boiling point of the hydroxy compound is 100° C. or higher, where the heteroatom does not form a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group at an end of the saturated hydrocarbon compound or the aromatic hydrocarbon compound.

4. The photocurable resin according to claim 1 , wherein the content of the repeating unit represented by Formula (Ia) is 35 mol % or less of the amount of the repeating units constituting the main backbone chain.

5. A mixture comprising:

the photocurable resin described in claim 1 ; and

a photocurable resin B comprising: a main backbone chain having repeating units represented by Formulas (IIa) and (IIb), and a (meth)acryloyl group and a non-photoreactive group at terminals;

the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom;

a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group;

a content of the repeating unit represented by Formula (IIa) being 15 mol % or less of an amount of the repeating units constituting the main backbone chain;

a content of the (meth)acryloyl group being 5 mol % or greater of an amount of the terminals; and

a content of the non-photoreactive group being 5 mol % or greater of the amount of the terminals:

wherein, a double line of a dashed line and a solid line represents a single bond or a double bond.

6. A photocurable resin composition comprising: the photocurable resin described in claim 1 , a monofunctional (meth)acrylate, a photopolymerization initiator, and a plasticizer.

7. The photocurable resin composition according to claim 6 , further comprising a photocurable resin B;

the photocurable resin B comprising: a main backbone chain having repeating units represented by Formulas (IIa) and (IIb), and a (meth)acryloyl group and a non-photoreactive group at terminals;

the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom;

a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group;

a content of the repeating unit represented by Formula (IIa) being 15 mol % or less of an amount of the repeating units constituting the main backbone chain;

a content of the (meth)acryloyl group being 5 mol % or greater of an amount of the terminals; and

a content of the non-photoreactive group being 5 mol % or greater of the amount of the terminals:

wherein, a double line of a dashed line and a solid line represents a single bond or a double bond.

8. The photocurable resin according to claim 2 , wherein the non-photoreactive group is formed from at least one type of hydroxy compound selected from the group consisting of

a monofunctional alcohol,

a saturated hydrocarbon compound having one hydroxy group and a heteroatom, and

an aromatic hydrocarbon compound having one hydroxy group and optionally having a heteroatom; and

a boiling point of the hydroxy compound is 100° C. or higher, where the heteroatom does not form a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group at an end of the saturated hydrocarbon compound or the aromatic hydrocarbon compound.

9. The photocurable resin according to claim 2 , wherein the content of the repeating unit represented by Formula (Ia) is 35 mol % or less of the amount of the repeating units constituting the main backbone chain.

10. The photocurable resin according to claim 3 , wherein the content of the repeating unit represented by Formula (Ia) is 35 mol % or less of the amount of the repeating units constituting the main backbone chain.

11. The mixture according to claim 5 , wherein the non-photoreactive group is a saturated hydrocarbon group which optionally has an ether bond photocurable resin.

12. The mixture according to claim 5 , wherein the non-photoreactive group is formed from at least one type of hydroxy compound selected from the group consisting of

a monofunctional alcohol,

a saturated hydrocarbon compound having one hydroxy group and a heteroatom, and

an aromatic hydrocarbon compound having one hydroxy group and optionally having a heteroatom; and

a boiling point of the hydroxy compound is 100° C. or higher, where the heteroatom does not form a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group at an end of the saturated hydrocarbon compound or the aromatic hydrocarbon compound.

13. The mixture according to claim 5 , wherein the content of the repeating unit represented by Formula (Ia) is 35 mol % or less of the amount of the repeating units constituting the main backbone chain.

14. The photocurable resin composition according to claim 6 , wherein the non-photoreactive group is a saturated hydrocarbon group which optionally has an ether bond photocurable resin.

15. The photocurable resin composition according to claim 6 , wherein the non-photoreactive group is formed from at least one type of hydroxy compound selected from the group consisting of

a monofunctional alcohol,

a saturated hydrocarbon compound having one hydroxy group and a heteroatom, and

an aromatic hydrocarbon compound having one hydroxy group and optionally having a heteroatom; and

a boiling point of the hydroxy compound is 100° C. or higher, where the heteroatom does not form a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group at an end of the saturated hydrocarbon compound or the aromatic hydrocarbon compound.

16. The photocurable resin composition according to claim 6 , wherein the content of the repeating unit represented by Formula (Ia) is 35 mol % or less of the amount of the repeating units constituting the main backbone chain.

17. The photocurable resin composition according to claim 14 , further comprising a photocurable resin B;

the photocurable resin B comprising: a main backbone chain having repeating units represented by Formulas (IIa) and (IIb), and a (meth)acryloyl group and a non-photoreactive group at terminals;

the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom;

a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group;

a content of the repeating unit represented by Formula (IIa) being 15 mol % or less of an amount of the repeating units constituting the main backbone chain;

a content of the (meth)acryloyl group being 5 mol % or greater of an amount of the terminals; and

a content of the non-photoreactive group being 5 mol % or greater of the amount of the terminals:

wherein, a double line of a dashed line and a solid line represents a single bond or a double bond.

18. The photocurable resin composition according to claim 15 , further comprising a photocurable resin B;

the photocurable resin B comprising: a main backbone chain having repeating units represented by Formulas (IIa) and (IIb), and a (meth)acryloyl group and a non-photoreactive group at terminals;

the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom;

a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group;

a content of the repeating unit represented by Formula (IIa) being 15 mol % or less of an amount of the repeating units constituting the main backbone chain;

a content of the (meth)acryloyl group being 5 mol % or greater of an amount of the terminals; and

a content of the non-photoreactive group being 5 mol % or greater of the amount of the terminals:

wherein, a double line of a dashed line and a solid line represents a single bond or a double bond.

19. The photocurable resin composition according to claim 16 , further comprising a photocurable resin B;

the photocurable resin B comprising: a main backbone chain having repeating units represented by Formulas (IIa) and (IIb), and a (meth)acryloyl group and a non-photoreactive group at terminals;

the non-photoreactive group being at least one type selected from the group consisting of saturated hydrocarbon groups and aromatic hydrocarbon groups which optionally have a heteroatom;

a hydroxy group, an amino group, —CH═NH, a carboxy group, or a mercapto group being not bonded to an end of the non-photoreactive group;

a content of the repeating unit represented by Formula (IIa) being 15 mol % or less of an amount of the repeating units constituting the main backbone chain;

a content of the (meth)acryloyl group being 5 mol % or greater of an amount of the terminals; and

a content of the non-photoreactive group being 5 mol % or greater of the amount of the terminals:

wherein, a double line of a dashed line and a solid line represents a single bond or a double bond.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2024
From: SIKA JAPAN LTD.
To: SIKA TECHNOLOGY AG
Reel/Frame 066641/0001 →
MERGER Recorded Feb 5, 2024
From: SIKA HAMATITE CO., LTD.
To: SIKA JAPAN LTD.
Reel/Frame 066493/0072 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 23, 2021
From: THE YOKOHAMA RUBBER CO., LTD.
To: SIKA HAMATITE CO., LTD.
Reel/Frame 058196/0760 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 27, 2018
From: ITO, TSUBASA; SAIKI, TAKEAKI; ISHIKAWA, KAZUNORI
To: THE YOKOHAMA RUBBER CO., LTD.
Reel/Frame 047000/0050 →
Priority Claims (1)
JP JP2016-070984 · Mar 31, 2016 · national
Continuity (1)
Related Publication 20200299446A1 · Sep 24, 2020