Polymer, method of producing the same, resist composition including the polymer, and pattern formation method using the resist composition
US-2026093178-A1 · Apr 2, 2026 · US
US9982082B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9982082-B2 |
| Application number | US-201715435641-A |
| Country | US |
| Kind code | B2 |
| Filing date | Feb 17, 2017 |
| Priority date | Jul 3, 2014 |
| Publication date | May 29, 2018 |
| Grant date | May 29, 2018 |
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Embodiments of the present technology include a formaldehyde-free binder composition. The composition may include melamine. The composition may also include a reducing sugar. In addition, the binder composition may include a non-carbohydrate aldehyde or ketone. Embodiments may also include a method of making a formaldehyde-free binder composition. The method may include dissolving melamine in an aqueous solution of a reducing sugar. The concentration of the reducing sugar may be 30 wt. % to 70 wt. % of the aqueous solution, which may be at a temperature of 50° C. to 100° C. The method may also include adding a non-carbohydrate aldehyde or ketone to the dissolved melamine in the aqueous solution to form a binder solution. The temperature of the aqueous solution of the dissolved melamine may be 50° C. to 100° C. during the addition of the non-carbohydrate aldehyde or ketone. The method may further include reducing the temperature of the binder solution.
Opening claim text (preview).
What is claimed is: 1. A fiber-reinforced composite comprising: a plurality of fibers; and a binder made from a formaldehyde-free binder composition comprising: melamine, a reducing sugar, a non-carbohydrate aldehyde or ketone, and a curing catalyst, wherein: the non-carbohydrate aldehyde or ketone: is selected from the group consisting of glyoxal, acetaldehyde, butyraldehyde, glutaric dialdehyde, acetone, methyl ethyl ketone, and pentanedione, or comprises a compound having the formula: where R 1 and R 2 are independently selected from hydrogen, an alkyl group, an aromatic group, an alcohol group, an aldehyde group, a ketone group, a carboxylic acid group, and an alkoxy group, and the binder composition forms (i) a reaction product of only the melamine and the non-carbohydrate aldehyde or ketone that reacts with (ii) the reducing sugar to make a crosslinked polymeric cured binder. 2. The fiber-reinforced composite of claim 1 , wherein the plurality of fibers comprises glass fibers. 3. The fiber-reinforced composite of claim 1 , wherein the binder further comprises a melamine salt formed by a reaction of the melamine with the curing catalyst in the formaldehyde-free binder composition, wherein the curing catalyst is selected from a sulfate salt, a phosphate salt, a borate salt, or combinations thereof. 4. The fiber-reinforced composite of claim 3 , wherein the curing catalyst is chosen from ammonium sulfate, diammonium phosphate, ammonium borate, or combinations thereof. 5. The fiber-reinforced composite of claim 1 , wherein the formaldehyde-free binder composition has a mole ratio of the melamine to the reducing sugar of 1:3 to 1:12. 6. The fiber-reinforced composite of claim 1 , wherein the formaldehyde-free binder composition has a range of mole ratios of melamine:non-carbohydrate aldehyde or ketone:reducing sugar of 1:0.5:6 to 1:0.5:12. 7. The fiber-reinforced composite of claim 1 , wherein the reducing sugar comprises dextrose. 8. The fiber-reinforced composite of claim 1 , wherein the non-carbohydrate aldehyde or ketone is selected from the group consisting of acetaldehyde, butyraldehyde, alkoxylated acetaldehyde, glutaric dialdehyde, acetone, methyl ethyl ketone, and pentanedione. 9. The fiber-reinforced composite of claim 1 , wherein the non-carbohydrate aldehyde or ketone comprises glyoxal. 10. The fiber-reinforced composite of claim 9 , wherein a mole ratio of the melamine to the glyoxal is 2:1 to 1:3. 11. A method of making a fiber-reinforced composite, the method comprising: providing a plurality of fibers; contacting the plurality of fibers with a formaldehyde-free binder composition to make a fiber-binder amalgam, wherein the formaldehyde-free binder composition comprises: melamine, a reducing sugar, a non-carbohydrate aldehyde or ketone selected from the group consisting of glyoxal, acetaldehyde, butyraldehyde, glutaric dialdehyde, acetone, methyl ethyl ketone, and pentanedione, or comprises a compound having the formula: where R 1 and R 2 are independently selected from hydrogen, an alkyl group, an aromatic group, an alcohol group, an aldehyde group, a ketone group, a carboxylic acid group, and an alkoxy group, and a curing catalyst; and heating the fiber-binder amalgam to a temperature of 100° C. to 250° C. to form the fiber-reinforced composite, wherein: the binder composition forms (i) a reaction product of only the melamine and the non-carbohydrate aldehyde or ketone that reacts with (ii) the reducing sugar to make a crosslinked polymeric cured binder. 12. The method of claim 11 , wherein the plurality of fibers comprises glass fibers. 13. The method of claim 11 , wherein the formaldehyde-free binder composition has a mole ratio of the melamine to the reducing sugar of 1:3 to 1:12. 14. The method of claim 11 , wherein the formaldehyde-free binder composition has a range of mole ratios of melamine:non-carbohydrate aldehyde or ketone:reducing sugar of 1:0.5:6 to 1:0.5:12. 15. The method of claim 11 , wherein the curing catalyst is chosen from ammonium sulfate, diammonium phosphate, ammonium borate, or combinations thereof. 16. The method of claim 11 , wherein the reducing sugar comprises dextrose. 17. The method of claim 11 , wherein the non-carbohydrate aldehyde or ketone is selected from the group consisting of acetaldehyde, butyraldehyde, alkoxylated acetaldehyde, glutaric dialdehyde, acetone, methyl ethyl ketone, and pentanedione. 18. The method of claim 11 , wherein the non-carbohydrate aldehyde or ketone comprises glyoxal. 19. The method of claim 18 , wherein a mole ratio of the melamine to the glyoxal is 2:1 to 1:3. 20. The method of claim 11 , wherein the fiber-binder amalgam is heated to a temperature of 150° C. to 200° C. to form the fiber-reinforced composite.
characterised by the bonding agents used · CPC title
Melamines · CPC title
containing oxygen in the ring · CPC title
to obtain coated fabrics · CPC title
Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen (aminophenols C08G8/16) · CPC title
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